See ya, 2023! 👋🏼

In most ways, 2023 was a fantastic year.

On the personal side of things, the kids are getting older (and funnier!). Dana and I were finally able to take a couple short trips – just the two of us. 🏝️

I ran two marathons this year and I’m happy to report that I’m faster (and fitter?) at 42 than I was at 25. 🎉

But, hey, you’re probably not here to read about my personal stuff. On the professional side of things, it was a mixed bag…

I stepped in as Strata’s CEO and, amongst other things, restarted my content efforts after a ~5 year hiatus. Turns out, LinkedIn and YouTube are worth the effort (as opposed to Twitter/X… maybe) — lots of growth is still available across the platforms. 🤯

Across the Results Junkies portfolio, revenues are slightly up and profits are mostly break-even. Zero exits (ie, IPOs or acquisitions) means zero liquidity but things are mostly the same for most others that I know to be in similar situations. 

Stress levels are higher for everyone this year, no doubt. Each year that passes, I become more convinced that venture-backed founders and bootstrapped entrepreneurs, particularly with brick & mortar “local” businesses, could learn a lot from each other. 

In December, I called a couple of the founders/entrepreneurs across our portfolio of companies and Strata’s clients…

A couple of observations and ideas from those calls:

  • Limiting your business to a particular geographic area is extremely risky. Whether you’re venture-backed software or a bootstrapped brick & mortar business, you have to think bigger than your backyard. 
  • Your business’ profit margin is mostly controlled by your ability to generate demand for your products and services. “But Paul,” you might say, “we can’t run a business if supplying our product or service isn’t profitable!” Maybe… but, even if you’re wildly profitably on the supply-side of your business, you’ll eventually get eaten up by a competitor that can acquire customers (and attention) better than you: distribution > product.
  • For companies with <$10M/year in revenues: your customers are people. And people follow people. Then people buy from people. To say this another way, the personal brand(s) of your founders, owners and team are more influential to your customers than your business’ brand. The number of people on your team with industry recognition is directly correlated to how many more new customers you’ll win and how many more opportunities will present themselves to you.

As we head into 2024, I’ll share a personal goal for me and a professional/business suggestion for you:

  • I’d like to do at least eight speaking events this year and double down on content this year: I have a feeling that doubling my content output could 5X-10X my reach. I’d also like to run three marathons with a sub-3:30 average time. 
  • If you’re serious about growing your business, 2024 is your year to stop being romantic about things: you’re fighting a war for the attention of the people that are not yet your customers. The sooner you accept that fact, the sooner you can act accordingly. 🚀

That’s a wrap! Happy holidays from me to you. If you’re still reading this, hit me up on X or LinkedIn! 👋🏻

Never Pick A Fight With An Elephant Head-On

Full Transcript

Ed Pizza: Just because we think it’s interesting doesn’t mean the person listening thinks it’s interesting.

Paul Singh: You can say your brand is whatever. You could say you’re hardworking. You could say you’re ambitious inaudible. But if people don’t see you do it, then that’s not your brand anymore.

Ed Pizza: From a restaurant standpoint, all we do in restaurant spaces is look at transaction.

Paul Singh: Why haven’t the Uniteds and the Deltas and the Americans of the world just recruited whoever’s running social for Wendy’s and Taco Bell?

Ed Pizza: Hey, guys. Welcome back to the Results Junkies podcast. It is a crazy time for entrepreneurs. The supply chain is causing issues for so many folks out there right now, things that we never even really assumed were a problem. And to win right now, it’s simple. As my cohost Paul Singh likes to say, you just need to outwork your competitors.

Paul Singh: Oh, I don’t think that’s true, though. I think it’s simple, but I don’t think it’s about outwork. I think it’s about picking the right thing and then really just nailing that. So I want to get away from this whole hustle porn, boil the ocean kind of thing that permeates the entrepreneurial community, because that’s just not smart.

Ed Pizza: We’re 30 seconds in, and Paul has already used hustle porn. I love it. So when you’re sitting there right now, man, and you’re thinking about the way the landscape looks, we were talking offline before we hopped on the show about your tweet on the three rules that you’re waking up every day and thinking about. And I think that when I read your tweet about it, it was one of those things where I nodded my head through all of them.
And yet I’ve known you for I don’t know how many years now, and I’ve never heard you frame it this way.

Paul Singh: Well, clearly, that’s because you haven’t been listening closely enough, because crosstalk I talk about these ideas often. So yeah, I tweet about this thing I’ve been thinking about for years, probably decades now. And I was actually surprised how many people picked up on it. I got a lot of DMs about it.

But anyway, I tweeted about this idea that I think there’s this game people play, this invisible game that defines how the world works. And to be clear, before I go further here, I have no idea, I’m probably stealing ideas from other people that I don’t remember. So I’ll just say out in front. And I also don’t have any empirical evidence to say that these are the three rules for everybody. But they’ve certainly worked for me. And for the people that I’ve shared these ideas with, over time, it seems to be working for them.

So the three rules are your brand personally and professionally isn’t what you say you do. It’s what other people believe. So that’s rule number one. And we’ll explain them here in a minute, so let me just go through the rules. Rule number two is you never pick a fight with a elephant head on. And then rule number three is if you understand and address the hopes, fears, and dreams of the people across the table, you win.

So those are the three rules of the invisible game, and I say that because I think the game, I’m doing air quotes here, the game that people talk about is this idea of hustle porn. Gosh, if you just work hard enough, if you just outwork somebody else, if you just, I don’t know, put in a little bit more effort, you’ll get there, whatever that is, a promotion, a startup, a growth, whatever.

But the invisible game is a little bit different, and I think that that’s not to say that hard work isn’t important, by the way. You can’t be lazy and be successful. But it’s just that the invisible game’s a little bit different. I think some of the most successful people I’ve watched over the last decade or two, they sort of … whether they do it on purpose or not, I just couldn’t help but notice they do it a little different.

So let’s just talk about rule number one. This whole idea of brand isn’t what people say or do. It’s what other people believe. I remember looking at … I’m not a brand guy, right? I’m an engineer by training. So I’m like … I didn’t quite understand brand. Maybe I still don’t now. But I think a lot of people would say, “Oh, this is our brand,” or, “This is my brand. I am X. I am Y.” And they somehow assume that maybe or imply that, by saying that, everybody else will now see them that way.

But the truth is you can say it, and now people will hold you to that brand or whatever. But then if you let them down or if you … What you actually do matters. I guess that’s my point with rule number one, is that you can say your brand is whatever. You could say you’re hardworking. You could say you’re ambitious inaudible. But if other people don’t see you do it, then that’s not your brand anymore.

And I think at the very least, the key idea here as I ramble is that if you understand that your brand is how people perceive you, then that should affect the way you either set your brand, like you need to lower those expectations, or you need to, in your actions, totally outdo them. This applies again as a company or as an individual or whatever.
And the second thing, never pick a fight with an elephant head on. I think that all these things apply personally and professionally. But you never really see any sort of success going against an incumbent head on. That’s just a war of attrition usually. You’re better off trying to find the chinks in the armor and coming in from the side. The old cliché is you eat the elephant one bite at a time.

And I know this sounds crazy, but there’s this other idea we have on the sheet about how we got stuck at airport and why aren’t the airlines doing some interesting stuff with … I don’t want to let that one out of the bag. But this is an example of that, where it’s like don’t pick a fight. If somebody’s your gatekeeper, you don’t get past the gatekeeper by insulting them. You’ve got to find another way.

There might be an incumbent in your industry that is much bigger than you. You are not going to do well to go head on with them. But maybe you go through the side by exploiting their unhappiest customers or exploiting some new customer acquisition channel that they don’t know how to do yet, right? So that’s what I mean by that second one.
And then last thing and arguably, I think, the most important of these three rules is this idea that if you understand the hopes, fears, and dreams of the people across the table, you win. Again, personally or professionally, we’re all dealing with people on the other side of the table, whether it’s somebody that could give you a promotion, somebody that could be one of your customers.

And the best way to just interpret this rule is just to say that everybody seems to just talk about features or hustle, like, “I’ll do X, Y, and Z. And gosh, I wish you’d give me a promotion,” or, “Our features are X, Y, and Z. That’s why you should pay us.” But look, on the other side of that table, for example, let’s say you’re in B2B sales. On the other side of that table is probably an HR rep that is the buyer, that wants to not fail.

So I’ll just use maybe our corporate wellness business as an example, right? We sell corporate wellness stuff to HR divisions around the country. And one of the things we try to remember is, even though what we provide is something that the employees that are parents … that the underlying employees of that company are the people that are going to open that box that we send, right? But the buyer is something different. The buyer who signs the check, who agrees to let Bump Health do this, they’re thinking, “Gosh, I don’t want to get fired. Is this a good bet?”
Anyway, you know the old adage is, “Nobody ever got fired for buying Microsoft.” Do you remember that?

Ed Pizza: I’m older than you, so it was, “Nobody ever got fired for buying Maytag,” but yes.

Paul Singh: Or that, right? And that’s what this is. If you really think about that statement, it’s like, yeah, these people are buying … When they think about whether to buy your solution as a corporation or not, it’s not about who has the best solution. It’s who’s least likely to let them down.

And I think that’s what this rule three is super important at, why I think rule three is even more important than the other two, is that if people just took the time to figure out how those people across the table think, what their hopes, fears, and dreams are, just speak to that. You want to be less risky if you’re selling into the corporate world. You want to be…

Anyway, I’ll stop there.

Ed Pizza: Well, when you talk about rule three, one of the things that pops into my head when you think about addressing the hopes, fears, and dreams of the people you win, it also goes back a bit to me for number two, about never pick a fight with an elephant head on.

And I remember back in the mid 2000s, we were in the restaurant space, still are. But back then, we saw that there were a lot of restaurants that really struggled with their point of sales systems, and there were just limitations that have been around for decades. And we said that we thought that there were some problems that we could solve, not to replace point of sale, but small things that we could start to do as SaaS was becoming easier to build and write code and get things out there quickly and stuff like that.

And I remember when we looked at this, about how we were wanting to try and create some things, we were trying to create a virtual wallet, almost like an Apple Pay before there was really Apple Pay. But it was really just supposed to be for restaurants. And I remember at the time thinking … I looked at … The dominant player in the space back then was a company called MICROS, MICROS-Fidelio.

Paul Singh: Mm-hmm (affirmative).

Ed Pizza: Had thousands and thousands of point of sale installs around the world and hotels and all that stuff. And I remember one interesting fact that I found when I started researching those companies was the number two company at that point, I don’t remember what their official name was back then, but it was a company called Radiant Point of Sale, and a bunch of mergers and all that stuff, so they’re part of Aloha and bunch of other stuff, which really isn’t relevant.

More in terms of the number one and number two, the number one player in the market MICROS, their research and development budget as a publicly held company was larger than the number two player’s gross revenue for the year. And so to your comment about never picking a fight with an elephant head on, we said, “Look, if we’re going to create this little product, we don’t really want to flaunt that we’re trying to take on MICROS, because if MICROS turns around and realizes that we’re trying to eat some small part of their lunch, they can crush us, because they’ve got millions and millions of dollars just sitting there waiting to research something. We need to be tactical and need to find a way to just create something that can be a recurring transaction for restaurant owners that would save them money, and they’re like, “Ah, this is cool.””

I’m not looking to replace your point of sales system. I’m looking to kill a pain point and save you five or 10 hours of paperwork a week. So why don’t you pay us 10 bucks a month for every one of your locations? And we’re just going to be this little thing over here that doesn’t interfere with your point of sales system.

Paul Singh: Yep. Yep, yep, yep. And I think that actually is an interesting example, by the way, too, right? Because I think in one of our earlier episodes, we talked about this idea that for a lot of these offline industries, the biggest opportunity I think in the next 10 years is really going to be what I call the intersection of online and offline. And what I mean by that is what you just talked about, this example of restaurants.

You know way more about this than I do, but when you look at the point of sales these days, here we are in September or October of 2021 where it’s Toast and Upserve or Breadcrumb and all these other things. And I look at these tools, and I’ve never owned or run a bar or run a restaurant or anything like that. But man, I look at these things and it’s like … it clearly to me looks like somebody outside the industry created this thing and shoved it into the restaurant.

And don’t get me wrong. I think I saw, was it Toast that went public a week or two ago and multi-billion dollar valuation? So people are going to say, “Well, Paul, even though they just shoved it in, they’re worth a lot of money.” That is absolutely true. But I’m just saying if you really took the time to understand those hopes, fears, and dreams and you took your tech skills and built it from the inside of those restaurants or the inside of those bars, I don’t know. If somebody like Toast can come in from the outside and make something worth that much money by pushing what I think looks like a very clunky thing, then, gosh, somebody from the inside could do much more.

Sorry. I’ll give you one example, by the way. I was just talking to one of my buddies who owns a bunch of bars, and I just happened to be looking over his shoulder at one of the morning reports he looks at.

Ed Pizza: Mm-hmm (affirmative).

Paul Singh: And it was interesting. As you scroll through, it gives him a high … I think that point of sale was maybe Breadcrumb or something like that. But anyway, what caught my eye as I was looking over his shoulder is it said something like, “Five employees clocked out with AutoClose.”

Ed Pizza: Yep. Yep.

Paul Singh: And I was like, “What is it?” And he said, “Well. Oh, yeah, yeah. They do it at the end of the night. They just …” I was like, “But why don’t they just clock out?” And he’s like, “Oh, well, it just auto closes them anyway.” And I was like, “But you as a manager, do you know that they … Did they stay the whole time?” He’s like, “Oh, I don’t know.”

Anyway, I just thought that was interesting. Maybe it’s not a big deal, but … Well, actually, the next thing that really interested me was he has … You know how you’re supposed to type in your server number to then-

Ed Pizza: Mm-hmm (affirmative).

Paul Singh: … I guess create a check or open a check? Well, what I thought was interesting was the majority of the sales were POS1, POS2, Handheld7. And I was like, “Well, wait a second. So why do you have IDs for people when they’re just using the generic log-in anyway?” He was like, “Well, it’s just too hard. These aren’t tech savvy people.”
I don’t know where I’m going with this, other than to say that it felt like there were a lot of extra features built into this thing, but the people inside the bar needed less than 10% of those features.

Ed Pizza: Well, I understand what you’re saying. I will clarify it. It’s not that they don’t … It’s not that they only need 10% of the features. It’s that the juice isn’t worth the squeeze.

Paul Singh: Yeah.

Ed Pizza: The time it takes to set up in a typical point of sales system is painful. So take your example of people clocking out. Well, I’ve said for years, “Why can’t a point of sales system have a report that tells me in the morning who hasn’t clocked out? Why do I have to go hunt for it? Why can’t I just get a notification that says, “Hey, here’s your four employees?””

Paul Singh: Yeah.

Ed Pizza: There’s a report, and it exists in every point of sales system. But there’s a number of steps I have to set up to have the system tell me that in some way that’s in my face.

Paul Singh: Yeah.

Ed Pizza: So that when I show up in the morning, my dashboard says, “Hey, you have five people that didn’t clock out last night,” as opposed to having to plunk through a bunch of screens or go dig up a report or things like that.

Paul Singh: Yep.

Ed Pizza: And when we think about the way that a lot of the SaaS companies that you and I know are built, if you think about the typical Google Analytics dashboard-ish sort of thing, it has all of your critical pieces right there in front of you like, “Hey, here are the numbers I need to work on today.” And for restaurant folks, it’s different. For Bump Health, it’s different. Everybody has their dashboard.

The probably is that, as you say, in this intersection of online and offline, in a lot of these typical offline sort of businesses like restaurants, the dashboards that they get are so poorly built for what these people actually need, because most of them don’t sit down with your friend who’s a restaurant guy and say, “Hey, what do you want on your dashboard? What would be 10 really cool things?” They go look at what reports are most often used in the system and just assume that must be what every restaurant owner needs.

Paul Singh: Yeah. Right.

Ed Pizza: When in reality, a lot of the smaller reports that they can’t find or don’t know how to pull are really the key information that they need.

Paul Singh: Yeah. Yeah. Yeah, yeah, yeah. Absolutely. It’s like there’s never been more technology available to brick and mortar businesses, but it’s also all glued together these days with spreadsheets, Zapier, and duct tape, to be honest.

And so I think that’s the real opportunity. To your point, I think that’s the real opportunity over the next couple years now, is how do you create maybe a deeper, smoother integration across all these different things that are available or build it from the inside out? I don’t know. Well, it’ll be interesting to see.

But I think for tech enabled people, people that have built, let’s just call it, air quotes, “online companies” or whatever, wherever you go out to eat this weekend, look at it from the inside and just see if there is an opportunity, because I really do think there is.

Well, that actually gives us an interesting segue to one of the other topics when we form a list here, is just this notion of a North Star. I think this is going to seem obvious to a lot of people, but maybe I’ll be able to make the point here. We’ll see.

The thing is I think it’s so interesting to me how many people make the common mistake of spreading themselves too thin. I think in one of the earlier podcasts we did, we answered somebody from Twitter that asked this question of, “How do you go from zero to a million in sales?”

Ed Pizza: Yeah.

Paul Singh: And it’s so interesting to me that so many entrepreneurs overthink the whole thing. So for example, when Bump Boxes was the first thing growing into Bump Health, right, we were very unemotional about this idea that we called the North Star. Transactions are all that matter. If you can’t move that average daily transaction from zero to one every day, there’s no point in thinking about what it’ll look like when it’s much bigger.

And if you couldn’t figure out how to systematically move it from an average of let’s call it one transaction a day to 10, and then from 10 a day to 100, you had to think about that and be unemotionally attached to any ideas that come up or any projects that come up.

And again, I know that people listening to this are probably like, “But Paul, that’s so obvious.” And I don’t disagree. But just you don’t have to scroll far down Twitter to see entrepreneurs saying, “Oh, what’s the new platform we should try?,” or, “What should we do?” Or they’ll complain about how many things they have to do in a given day. And it’s like, “Well, no. That should tell you you’re spreading yourself too thin.”

Anyway, this is actually a little plug, by the way. So behind the scenes for the last couple years, I’ve actually been working on this … So when I was starting to build this up, I knew that transactions were all that mattered and I built a team around me that only focused on those transactions. And then I built a culture and a company that did all that, right? And I built a little Chrome extension that only really worked for me originally, where it would just pull my Google Analytics eCommerce data.

Ed Pizza: Yeah, I saw that.

Paul Singh: Every time I opened a tab, it would just … that’s the first thing it would show me, is what today’s transactions were. And then I’ve just honestly … It’s been on my browser for years. It’s such a crappy little plugin.
And then more recently, somebody I know happened to look over my shoulder and was like, “What is that thing?” And I was like, “Oh, yeah. That’s this thing,” whatever. And he’s like, “Oh, man. I want to use it.” And it dawned on me at that point that maybe I should just open source or make a free thing or whatever.

So anyway, I’m almost at the point where it’s ready to launch into the Chrome store. I think I’m going to call it North Star. Honestly, it’s nothing special, but the idea here is that it helped me just stay focused on the transactions. So every time I opened a new tab, I wanted to know how many transactions have I had today and how does that compare to the average daily transactions over the last seven days, the last month, and the last year.

And it, for me, worked out really well because it just kept me focused. And every time I’d get off track and opened a tab, whether it was to doom scroll through social, this was my reminder that I had to get back to work.
And so anyway, I think I’m going to call it North Star. I don’t know. But, yeah. Hopefully, by the time this thing’s published or this podcast is published, hopefully it’ll be available. It’s going to be free. It’s all secure and all that stuff. And I won’t have access to your data. It’s all stored on your browser there.

But, yeah, hopefully, it’ll help other … It’s primarily designed for other eCommerce stores. But we’ll just see. I’m interested in what people say. But growing your company is not easy, but it is very simple. Just pick that one North Star and just stay laser focused on it. The world wants to distract you. The internet wants to distract you. And you have to actively fight that to stay focused.

Ed Pizza: Well, and you say it’s obvious. And you’re right. And I do still think that so many companies miss it. And in reference to the plugin where you’re talking about eCommerce specifically, that makes a hundred percent sense. But it also goes both more offline and more online. So from a restaurant standpoint, all we do in the restaurant space is look at transactions. And certainly, we’re trying to increase them, but we’re also trying to increase the size of them.

Hey, the old McDonald’s adage of, “How do I get you to order fries and a drink with your burger? Well, I package them all together.” And then on the online model, I’m a travel writer. I’m a podcaster. So we’re looking at, hey, how do we get somebody to read … to click on three or four different stories instead of one when they’re on my site? Or from a podcasting standpoint, how do we get folks to … The average dwell time for podcasts is about 48%, according to industry statistics. That means that most of the people listening to an average podcast will listen to half of it. And so if that’s our transaction here, then my North Star is how do I get you to listen to 60% of this podcast, and then 70%, and then 80%? We’re putting out the whole episode. I don’t want you to stop halfway.
And I think people … I use podcasting because we’re here recording right now. I think a lot of podcasters are focusing on, “Hey, I want to put out a great show that my friends tell me sounds good and looks great. Maybe I get some Twitter re-shares and all that stuff.” And that’s all cool and stuff. And downloads are valuable as well as a statistic. But at the end of the day, there are millions of iPhones all across the country that are downloading podcasts automatically and to various players. But are people actually listening?

And so I think defining what a transaction is for your business and what it means to succeed, I think, is critically important.

Paul Singh: Agreed. And maybe I’m going to take this in a direction it may not want to go, but I’ll just say that I think that … Just listen to what you just said there, and I’m going to put you on the spot a little bit.

Just crosstalk what you said there, it’s like, “I want people to listen to 60%,” or, “I want dwell time to be X,” “I want this,” or even sometimes other entrepreneurs say, “I want more sales. I want more stuff.”

I don’t know how to say this clearly, but what I’ll just say is those goals are a byproduct of whether or not you add value to the listener or whether or not you add value to the customer. Now, that doesn’t seem like a groundbreaking and new, novel idea. I admit that. But I think that it’s important to …

Let’s just use the podcast analogy because that’s what you used, right?

Ed Pizza: Yeah.

Paul Singh: If we want to drive dwell time up, we need to give people something worth listening to.

Ed Pizza: Absolutely. Yeah.

Paul Singh: And the Howard Sterns of the world will give you shock value, and that’s what drives their crosstalk.

Ed Pizza: … shock value from us.

Paul Singh: In our case, I’m hopeful that this particular podcast is giving people tactical things they can do to grow right away. But maybe in the absence of that, maybe we’re giving them an interesting viewpoint from two operators and two investors that might make them think about a problem they’re dealing with a slightly different way.
So all that to say, though, that if you really do want to grow whatever your metric is, if you know what your North Star is, then it’s important, I believe, to then recognize that that North Star is a proxy metric of whether or not you actually add value to the underlying customer on the other side of that.

In other words, in my world, if I don’t make a way for moms to have a safer and easier pregnancy, she will not use any of our stuff. If I don’t make her life easier and allow her to extract every dollar the insurance company owes her with seven clicks, my Bump Medical business doesn’t grow.

So anyway, I’m not saying anything groundbreaking or novel or new, but I just think that people that talk about growing whatever their metric is, they don’t talk about what’s on the other side of that coin, right?

Ed Pizza: Yeah. And I think we’ll use this podcast mentality again. Just because we think it’s interesting doesn’t mean the person listening thinks it’s interesting.

Paul Singh: Agreed.

Ed Pizza: You’ve got to be critical with yourself to say, “Hey, are people actually absorbing this? If not, I need to pivot and I need to figure out some other way to connect with my audience or connect with my customer,” as you said.

Paul Singh: Agreed.

Ed Pizza: If the mom doesn’t get the value, why is she going to continue to use the product? And I think I see so many … Not to belabor it on podcasters specifically, I just see so many that get into it and say, “I don’t understand why I can’t get past 100 downloads. I don’t understand what the issue is.”

And I think I would just say collectively the easy issue is, if you’re in any sort of a content production business and people aren’t clicking, downloading, reading, whatever, you need to take a hard look at whatever it is you’re producing, because it’s not resonating with people. And it goes back to your three rules, where your brand is what other people believe. If we believe that we’re tactical and we’re giving people great advice, but they never listen past the first five or six minutes, we’re obviously not giving them great advice or advice that they view as helpful or great for them.

We always have this long list of stuff that we say we’re going to go over each episode, and we’re already almost 30 minutes in and we’re on topic number two and half.

Paul Singh: Yeah. Yeah.

Ed Pizza: So I’m curious … I’m going to tee up two and I’m going to let you pick which one we do next. Now, do you want to talk about Delta Airlines and large companies with old, stinky moats, or do you want to talk about the Ozzy controversy?

Paul Singh: Okay. I was actually going to use what you just said there to segue into that Delta Airlines moat thing, because I thought that might be an interesting way to take that last part of the conversation a little further.

Ed Pizza: Okay.

Paul Singh: So I don’t exactly remember how this particular topic got on the list, but I remember what we talked about right before the show in terms of the idea. So to what you just said, let’s try to connect this idea, this part to that last idea.

So this idea of being interesting, being useful, adding value to the listener, adding value to the customer, and if you could do that, then the proxy metric, your North Star, will move on its own. So this particular idea was … Again, I don’t remember how this ended up on here, but I do remember what we talked about right before the show, and that was why aren’t airlines using things like social media complaints to just give a free seat on a similar route?

Ed Pizza: Oh, I love that idea that you came up with. Yeah.

Paul Singh: Yeah.

Ed Pizza: Yeah, yeah, yeah.

Paul Singh: Yeah. So I can’t remember exactly … Again, I apologize. I can’t remember how crosstalk.

Ed Pizza: No, I’ll tee it up. I’ll tee up. So it was crosstalk.

Paul Singh: Yeah. Go, go, go.

Ed Pizza: I’m a top tier Delta Diamond Elite member, and I called up because I had an issue with a ticket.

Paul Singh: Do you listen to yourself? “I’m a top tier Diamond Elite.” God, who talks like that?

Ed Pizza: I was just trying crosstalk to define for people what Diamond is, because they use all these plutonium and titanium. And so it’s like it used to always be it was silver, gold, platinum. And so everybody knew what it is. And now, it’s like, “I’m super titanium plutonium elite.” And it’s crosstalk.

Paul Singh: God, that’s a mouthful. That’s like-

Ed Pizza: Yeah.

Paul Singh: I’m over here, I’m like, “I’m 1K.”

Ed Pizza: Yeah, right. Right. Well, yeah. But it’s like if you say to somebody, “I’m a United 1K,” and they’re not a traveler, they don’t actually know what that is. They’re like, “Okay. Well, are you at the top of the pyramid or the bottom of the pyramid?” So I’m just defining for people what they already know, which is crosstalk.

Paul Singh: … United 1K is still the bottom of the pyramid. So…

Ed Pizza: Yeah. But if you’re 1K, they say sir when they screw you, so just to be clear.

Paul Singh: Oh, you go to the nice airports. I don’t even get that, but okay.

Ed Pizza: So anyway, so I called the customer service line, which should have the shortest wait times because I’m … Again, Paul loves this phrase. I’m a top tier elite. So I should be the smallest group of people that produce the most revenue for them.

And the wait time was over three hours to get someone to call me back, or I can wait on hold that whole time. And so as I framed it to Paul when it happened, it was … With these large incumbents, they have moats. And in this case, with airlines, it’s obviously hard to start an airline. You need lots of money. You need slots at airports. You need all of these things.

And so the age old question is can Delta get away with making their most valuable customers wait three hours to talk to someone on the phone? And similarly, how could another business attack this?

Paul Singh: So can they do this? Look, they did it to you and you’re still there.

Ed Pizza: All right.

Paul Singh: Right? So the answer is can they do it? Yeah. Now, but to tie this idea back to a couple of the other topics we talked, for example, not attacking an elephant head on or even this previous idea of how to add value, let’s just say you were an upstart airline. Now, I’m going to say this really carefully because I know you travel people are very particular about crosstalk.

Ed Pizza: You travel people. Thank you for crosstalk there.

Paul Singh: Yeah. But, here. Let’s just tie it together with a hypothetical example here. So if I’m an upstart airline and I want to add value and I want to build my business and I want to not attack Delta head on, they’ve got the 737s and I’ve got the 30 year-old CRJ or whatever. Well, look, if I’m sitting on a route that let’s just say was a high volume route between X and Y locations, and I sit there and watch social media, I want to see for better, for worse the people that complain and go, “@Delta, my flight is delayed. DL Flight number whatever. Come on, guys.”
So I’d watch that. And I don’t know how often that happens, but at a high volume hub, I bet it happens a lot. And I know my plane’s going no matter what. And I’d be sitting there, looking for those tweets or whatever, and I’d just offer the unbought or the open seats for free, because the plane’s going no matter and this is your chance now for getting people over.

Now, is that a great idea? I don’t know. But maybe that way of thinking inspires some ideas.

Ed Pizza: Well, I don’t think you have to be a startup to think that way either in a market like this. I think you talk about it like, “Hey, I’ve got the smaller planes and I need to find ways to compete.” But I think this was Delta’s model when they came into Seattle to compete with Alaska Airlines. It was, “Hey, let’s go eat their lunch and let’s offer status to their top tier status members.”

To your point, I love the idea, because all the airlines are on social media. Why wouldn’t you try and pick off the people that are complaining about another airline? Typically, those are customers … The customers that are taking the time to go on Twitter and engage an airline directly, not just ranting about something, they’re likely probably going to be somebody who flies more than once a year.

Paul Singh: Honestly, why hasn’t … And maybe you know this. Why haven’t the Uniteds and the Deltas and the Americans of the world just recruited whoever’s running social for Wendy’s and Taco Bell? Have you seen those crosstalk?

Ed Pizza: Yeah. They don’t.

Paul Singh: Sometimes, Wendy’s and Taco Bell will get into fun fights with each other, and they just start to bash each other. It’s just hilarious. They’re not dong it to be mean. But somebody ought to recruit those people.

Ed Pizza: Yeah. It’s just never been something in the aviation industry in the US. There’s a few airlines that have a little fun on Twitter, Southwest, Jet Blue to a lesser extent. Those guys have a little fun. But very rarely do they poke at other airlines and try to eat their lunch.

Paul Singh: And maybe we’ll talk more about this idea in the next episode. But just to plant the seed, there’s this framework that I use when I think about building new businesses. And so with Bump Health, we’re a collection of a couple different businesses, right?

And so there’s this framework that I’ll just hint at here and we can talk about it more in the one of the future episodes. But related to this idea, when I think about starting something new, the way I think about is, number one, find the incumbents in the industry that I want to get into and, of those incumbents, now filter them and only look at the ones that are greater than 10 years old, have greater than 1,000 employees, have greater than 10 or 20 million dollars of revenue.

And then here’s the important part. Imagine rebuilding that company if you had a deep understanding of today’s technology stack. Number two, imagine rebuilding that company if you had a deep understanding of today’s digitally native consumers. And number three, imagine rebuilding that company today without that legacy stakeholder baggage that tends to hold these companies back from the innovation that needs to happen.

And I think that framework has worked very well for us. I think it could work very well for others. But back to this idea, I think that those airlines have not innovated, but the people sitting on the little tube are different consumers now. And I think that there’s opportunity there. I think whoever has that first move or advantage, whichever one of those airlines ends up being the most forward thinking, this is not … Innovation is not, “How do we find an internet device on the plane that adds another hundred megabits a second to the consumer?,” or whatever. No. it’s actually, “Which airline could meet the digitally native consumer exactly where they are and build their brand that way?”

Ed Pizza: Well, and to tie it all together, and God knows I’m a bit of a cynic, but I think this is where you get into tying back to your three things, your three rules of your brand and what people perceive you to be. I think that there by and large is a perception that airline travel, at least in the US, is a commodity business. It’s meant to be traded at the lowest common denominator. People are looking for a cheap airline ticket to get to that cool place they want to go.

And so a lot of it for folks who are … for discretionary travel, it’s almost always based on time and price. When can you get me there and what’s it going to cost? Whereas when you talk about things like Bump … And to be clear to folks listening, I don’t have any vested interest in Bump. I’m not an investor. I spend a lot of time listening to Paul talk about it, so I know about it. I think when you think about that, you’re talking about how to talk to someone about one of the most personal and emotionally connected decisions they’re ever going to make in their life: child care. And you’re saying, “Hey, we’re going to be somebody that you can trust, somebody you can believe in, somebody who’s going to tackle certain things that are pain points for you that keep you from the enjoyment of being a mom.”
Obviously, an insurance company is the ultimate mom enjoyment killer. And you’re saying, “Hey, we’re going to try and get rid of those mom enjoyment killers.” And I think that’s the … You’re tackling that, and that’s your … Alongside transactions, that’s your North Star.

Paul Singh: Well, yeah. And again, this might … Maybe the episode’s getting a little long and the people that dropped off at the 50% mark are going to miss this, and we’ll talk about it more in a future episode. But here’s the deal. What you just described there, this notion that people see air travel as a commodity thing, “Get me from A to B as cheap as possible,” you’re not wrong there.

But this is a half baked thought and I’ll have it ready for the next episode, but here’s the thing. When you’re starting something new, whether it’s our company or a new airline or a new startup, whatever it is, brute force is what you use to get off the ground. You have to just brute force your way, figure out how to acquire customers. You’re probably not going to have a brand yet. You’re not going to know all these things. You just have to get started. And that’s understandable.

But here’s the part that I’m starting to recognize now personally, is that at a certain point, what happens is there’s a certain sameness, a certain sameness across everything. So for example, you’re right, airlines tend to be a commodity business. But why is it that I choose to fly United on a regular basis versus you choose to fly American or what it is you fly usually?

Now, we can joke all day my airline choice sucks, yours does too, right? But this is the Nike versus Adidas thing, right? At a certain scale, the shoes are all the same. But some people choose Nike. Other people choose Adidas. Here’s where I’m going with this. At a certain scale, it becomes about brand. And this goes back to rule number one, the invisible game, that brand’s not what you say it is, it’s how they perceive you and really how they perceive themselves alongside you.

So here’s where I’m going with this. The most important lesson I think I’m starting to recognize now, and I’ll hopefully have a better way to talk about this in the next episode, is this idea that you have to actively, proactively, consciously work towards a business and a brand that forces the consumer to choose whether they see themselves in the way you see the world, but you’ve got to not let them compare you to others.

And I know that’s easier said than done, right? So I’ll just say it one more time. You have to force your customer to choose whether they see the world the way you do and simultaneously disallow them from comparing you to others.
So when I think about … Let’s just use our business as an example. And just as an example, okay? So I don’t want to make it about us, but hopefully this maybe sparks some thoughts for the listeners and maybe for you as well, is I believe that mom’s life should be easier. And I think that I want to make you choose whether or not you agree with that.

But what a lot of other companies do, including us in the earliest days when we were trying to figure things out, we were like, “Gosh, we’re at 33.99 and the other one’s at 32.99. Do we go down one or do we …” Everybody does this, right? If you compete on price or features or all this stuff, at a certain scale, you’ll stall. And you’ll stall because you’ve positioned yourself to be compared against the other thing. You have to make a conscious change and go the other way and say … It’s not that we don’t want to serve the price conscious customer. That’s not what I’m saying at all. It’s just that we believe that it shouldn’t be hard to have a safe and healthy pregnancy. We believe it shouldn’t be hard to extract every dollar that’s owed to you by your insurance. We believe it shouldn’t be hard for you to know without a doubt whether or not you have the best and most price effective insurance, whether it’s Life or PNC or anything else.

If you believe that life shouldn’t be so hard for moms, then you can’t not choose us. And I think that’s … When I think about how brands, other brands, particularly even large airlines, should be thinking about this stuff is how do you force more of the customers to choose a certain thing? Again, I don’t know much about airlines, but I think that the company that came the closest to this, at least in my limited experience, company that came closest to this is Virgin America. I don’t know if … Again, I’m no brand expert, right? And I understand that they got acquired and different people think it was a failure and different people think it was a success, whatever, right?

But as a consumer, they were the first airline that I recall that made travel fun and cool and sexy. I don’t know if you ever flew on them.

Ed Pizza: Oh, yeah. No. Many times.

Paul Singh: They were the first airline that I recall … I’m 40, so I don’t feel like I’m old or anything like that. But they were the first airline I remember that ever made the safety video interesting. And then after that, some of the airlines started to do it. But prior to Virgin America, I don’t remember it being interesting.

Ed Pizza: Well, and there are other examples, but I think, yeah, Jet Blue, and then before there were really safety videos, Independence Air out of Dulles used to have fun videos where they played on politics and other things. Not videos, but audio played on politics and all the things that were popular at the time.

But I think you bring up a point about companies that come into the space and try and differentiate themselves. And I think … Ultimately, I think it’s why we see a lot of entrepreneur dollars go more towards the SaaS businesses of the world or things that are easily changeable as you learn about your customer and how they perceive you. You can obviously iterate a lot quicker at Bump than Delta or American or United can in buying new airplanes.

I think that’s probably a good place to tee it off and say that we’ll get back to this next week. You know I love talking airlines, so we can spend a whole episode geeking out about airlines and bore the heck out of everybody and watch our dwell time drop.

Paul Singh: I know it.

Ed Pizza: But before we do wrap, one thing I like to ask people to do as well is … We’re a few episodes in at this point. So I want to ask you guys what’s working and what’s not. Just going back to Paul’s three rules, let’s figure out how you guys perceive us. What parts of the show do you like? What parts of the show do you not like? Do you like Paul? Do you like me? Obviously, you like me.

But, no. Let’s figure out what works and what doesn’t, and let’s figure out what we can bring you guys that is valuable. We love you guys are submitting questions, and you can keep doing that at You can also hit us up on social media. Paul is @PaulSingh on Twitter, and I am @PizzaInMotion.

But at the end of the day, we want to answer your questions, but we also want to be topical and interesting. So tell us what you love about the show. Tell us what you hate about the show. And gosh, we’re going to act accordingly, right, Paul?

Paul Singh: Look, the whole point of this podcast is to give people stuff that helps them grow their careers and themselves better. So yeah, if we’re not doing that, then what in the world are we doing?

Ed Pizza: I don’t know. We’re sitting in our basement staring at each other on camera.

Paul Singh: Oh, that, I think, is adulting in 2021, which is a different episode entirely.

Ed Pizza: All right, man. Well, I’m back on airplanes again next week. Are you staying put or are you going to be out on the road?

Paul Singh: So next week, I’ll be on the road just for a day or two. I’ll be out in Sioux Falls speaking at an event, and I’ll tell you all about that after that’s all done.

But yeah, other than that, I’ll be cranking. I’m actually hoping to close an acquisition as well, so just going to hint at that and maybe just talk about that crosstalk.

Ed Pizza: Yeah. Do we talk about it when you guys close it?

Paul Singh: Can I or will I?

Ed Pizza: Will you?

Paul Singh: Oh, you know I like to talk, so absolutely I will.

Ed Pizza: All right. We’re going to hold you to it. All right, folks. Thanks for tuning in again. Until we upload again, we’ll talk to you soon.

Paul Singh: All right, everybody. Hey, thanks for the time. And for anybody still listening, Ed’s so worried about dwell time. Thank you for making it all the way to the end.

Ed Pizza: Dwell, dwell, dwell.

What Fundable Founders Have In Common

Full Transcript

Paul Singh: In a world where everybody’s trying to build relationships on Zoom, going and meeting them in person is a differentiator.

Ed Pizza: You said no to Airbnb and Uber in the same week because you thought both ideas were stupid.

Paul Singh: I don’t think it’s the founders that have changed as much as it’s that I’ve changed.

Ed Pizza: Here we are six years later sitting in our homes with headphones and t-shirts on, telling people why we think they’re right or wrong. Who really gave us the right to do that? Hey guys, welcome back to the Results Junkies podcast. As we’ve said the past few weeks, we are all about tactics and both of us have been pretty busy this week. Paul, I know you’ve got a ton going on, knee deep in another acquisition, huh?

Paul Singh: Yeah it’s been a busy week. Actually. It’s been in the works for about two weeks now. But the thing about acquisitions is, they’re more delicate. You read the news or the techcrunches of the world for better or for worse. And they make it sound like, well two companies met and magically a wire transfer happens. Not like that at all.

Ed Pizza: Oh, it’s almost like that, every one of these I’ve been involved with, it’s like it never really feels like it’s real until it’s done. And there’s all these points in the process where you’re a hundred percent sure it’s not going to close. And then you’re a hundred percent sure it is going to close.

Paul Singh: Well that’s true. And it’s also the case that it doesn’t even feel like you’re working because you’re talking a lot. Everybody thinks these sort of things are about deal terms. And maybe there’s smarter people than me that can make that happen. But when you’re dealing with culture fit first, and you’re thinking about it that way, you’re really talking a lot. It’s like speed dating. They’re like, are we getting married in three weeks or what?

Ed Pizza: The answer to that is no, you’re already married.

Paul Singh: I feel like my team probably is like, where in the world as Paul? And I’m over here thinking, God, I am so exhausted. This is a lot of talking. So anyway, been a busy week. What’s going on in your world?

Ed Pizza: Just back man, was out in Reno for the week, checking on some of our businesses. And obviously you and I have been tossing back and forth some stuff on a couple of potential investments that we’re looking at in some really interesting spaces. But before we dig too deeply into that stuff, I also want to remind folks to hit the subscribe button wherever you’re listening so you can get notified of new episodes as as soon as we drop them every week. And also you can shoot us your questions, email us Paul is on Twitter @PaulSingh and I am @pizzainmotion across all those Twitter, Facebook, Instagram ish type places. But yeah, it sort of feels like it’s getting back in investment season for us as well. I don’t know if that’s specifically related to people coming out of the pandemic and more things being appealing. But it feels like as people started traveling, we’re also talking about investments more.

Paul Singh: Yeah, I hate to admit this openly, but the truth is it’s also about my attention span. And I think I’m trying to be a little bit more conscious about carving out 10 or 20% of the week to look at deals that come through the inbox and that sort of thing. So I don’t think it’s because the deals have been bad or the bets have been bad through the pandemic. I think it’s really more just attention span for me. And I don’t know how you feel about it, but I definitely think I didn’t give enough attention to some of the folks that were fundraising over the last year. But now hopefully we’ll pick off three or four of them a week and see where it goes.

Ed Pizza: Yeah I know that I’d use the word attention span per se. I understand what you mean. I think for me, there were certain times during the pandemic where… Because I wasn’t a hundred percent sure on certain sectors, if you will. And maybe I wasn’t willing to invest the time to go deeply in some companies. And I think a great example of that is supply chain stuff and just what we’ve seen with tons of ships moored off the coast, not able to drop their product and how that’s causing ripples in so many different things. And so certainly there’ve been a couple of hardware things that wandered across my path. And I just said, look, I don’t have the time and wherewithal to figure out if you have supply chain issues coming down the pipe to write a check. And so I certainly see some of those factors have been impacting the things that I’m willing to put time into.

Paul Singh: I get it man. The unfortunate reality is we’re all… Despite all the hustle porn, hustle culture, that’s out there, we all got the same hours in the day and you got to make those choices. I think people sometimes look for some sexy answer here, but the truth is, it’s just a practical matter of things.

Ed Pizza: Yeah. And one of the things that we’re looking at right now I think, it brought up an interesting question. And as folks will see on my other podcast, one of my frequent guests comments on the fact that I frequently drop things in as a surprise. And I swear to God, I don’t do this on purpose. I meant to put this on our show notes for this week, but you and I both, we’re talking about a company in the pet space and you guys just lost Jack just a handful of months ago. Dana’s dog of a long number of years, we’ve lost a pet. And so definitely an emotional connection for me. And I really struggle, it’s almost like… There’s a question in there. I’m just not sure what the right question is.

But I sit there and I always wonder where this line is. So we’re looking at this company, I’m very interested because pets are a part of our family and they have been since we’ve had kids, so 15 plus years. But where’s that line between, I love it and I think, I have a vested interest in it as a consumer, and I’d love to see this company succeed. Versus trying to figure out if those feelings are clouding my judgment on the investability of this concept. And by the way, this goes back to one of your comments. You always say this on the tech tour, you said no to Airbnb and Uber in the same week, because you thought both ideas were stupid. And the flip side I think is true. I’m invested in this idea, so is it the wrong idea to say yes to this, versus saying no to Uber and Airbnb?

Paul Singh: Yeah. Well, here’s what I would say. First off, I like to invest in entrepreneurship, not innovation. And I’ll explain what that means. So let’s just for a moment here, look at what we’re doing with Bump, just to make an illustrative point. And then I’m going to get to that particular company that we’re looking at investing in. On the Bump side, people misunderstand what entrepreneurship versus innovation really means. The point is, if you look at how we’ve expanded into multiple business units, none of them are new. What we’re doing is, is we’re looking at incumbents that are adjacent to us that are maybe more than 10 years old, making more than a hundred million dollars a year. And then rethinking what that business would look like if they had our deep understanding of today’s tech, our deep understanding of today’s moms, digitally native moms. And without the legacy baggage of the past.

So taking it over to this company that you’re talking about, and the idea of pets and all that stuff. The reason I’m really interested in it is that I know the founder, I knew the head sales guy, invested in them in the past. Actually hired one of them in the past as well. And on top of that, the concept is not new. Before I even started to look at it, when he first emailed me about this… And hopefully he doesn’t hear this, but I stalled on replying to him for a day or two, because what I wanted to do after hours one night was just go scan the public earnings reports of the Banfields of the world. And get a sense of, what is the scale of some of these other insurance programs that are out there like this?

So that in theory gives me an idea of, okay is this big? That sort of thing. And that was confirmed. And then, as I talked to him, it was really just to talk about the differentiation that he had. It’s not interesting to… You never go after an incumbent head on, that would never be smart. But then there’s do they have a novel approach? And in this case, without giving it away, I’ll tell you offline, but they have a very novel approach that skirts some of the regulatory issues while still providing the customer the full coverage amounts and things like that. So I don’t know if that was… Maybe that was a little too rambly and We lost a couple of listeners there.

But I guess what I would just say is that, when I think about these businesses, you’re absolutely right. We should not judge our decision to invest, or not invest in things because of our personal emotions. That’s a recipe for bad decisions in investing, in careers, in life in general. Rather what you should look at is, is there a proven demand for this thing? Are they going up against existing competitors? And if the answers to those things are yes, then is there a novel approach that they’re taking? And that’s really what you’re betting on.

So in this case, I guess here’s a summary. On that particular deal, we are not risking anything in terms of, is there a market or anything of that sort. The question here really is, is this other novel approach coming in from the side interesting? That’s what the fundamental bet is. And again, I have a lot more thoughts on this. I don’t want to give the deal away here. Lord knows these people listening to this will invest in it before we close our deal.

Ed Pizza: Yeah.

Paul Singh: But yeah-

Ed Pizza: I have a lot of interest in this space too. I’ve done a lot of research, so that’s why it’s certainly, this one’s very interesting for me. And it’ll be interesting to watch, see where it goes.

Paul Singh: Yeah, maybe we’re just in a timestamp of this for later on, for posterity’s sake. But I think this could be an interesting partnership for us on the Bump side too. It turns out the overlap between people that love pets and the people that love kids is actually pretty, pretty good.

Ed Pizza: Yeah. No, I agree. I don’t want to use words that are thrown around in the insurance company very often, but I do see, wait for it, bundling opportunities here.

Paul Singh: See. That’s how you know there’s some dads on this podcast. You’ve got the dad jokes, episode three.

Ed Pizza: Oh dad jokes. The worse they are the better I am.

Paul Singh: No, the worse your dad jokes are, the more kids you got. That’s how it goes.

Ed Pizza: Oh is that the deal? So yours must be worse than mine?

Paul Singh: A hundred percent, ask my kids.

Ed Pizza: You have 50% more kids than I do.

Paul Singh: A hundred percent, yep.

Ed Pizza: Well, at least as far as we know.

Paul Singh: Percent. Yep.

Ed Pizza: Well, at least as far as we know.

Paul Singh: Oh boy, you’re going to get me in trouble.

Ed Pizza: [And me 00:11:06] too.

We’re talking about entrepreneurship, I think it’s a good segue into one of the tweets I had flagged. Daniel wrote us a couple weeks ago; it’s an interesting high level question. I’m not sure there’s a tactical answer. But I was trying to think back through our investing history, and yours is much more prolific than ours.

He asked, “What’s different about founder number 1000 you invested in, versus number one? And what’s the same?” And then he asked about the pitfalls that young entrepreneurs should avoid. I think we’re going to talk a little bit about valuation in a bit and what young investors should focus on when they’re negotiating term sheets.

What do you think has changed with founders over the arc of the time that we’ve both been investing?

Paul Singh: I don’t think it’s the founders that have changed, as much as it’s that I’ve changed. What I mean by that is, is that I think the more opportunities I’ve had to look at companies to invest in, the more I’ve had the ability to then refine my thinking. But then, as I invested in them and the more I saw what didn’t work, I was able to kind of figure out why I made the decision to invest originally. What’s happened is, over the years now I’ve gotten more and more clear on what my thesis is, and what my “go/no go,” “what’s negotiable, what’s not” thing, has evolved.

So I think the difference between founder one and founder 1000… I don’t know how to answer that. But what I do know is, is that the portfolio of founders; if you took some random subset of our founders right now and put them in a proverbial room together, I think you would see a lot of similarities. In the sense that what you would see, what I like to describe as, they will be the combination of relentlessly resourceful, incredibly self-aware; meaning that they have a bias towards action, that relentlessly resourceful thing, but they have a sense of self awareness. They can speak assertively, but they hold their opinions weakly if somebody else brings some other data to the table.

Daniel, it’s a good question, it’s a nuanced one. But I don’t think it’s the founders… Founders change over the years, technologies, everything changes, right? But the portfolios are really a reflection of how the investor thinks. Well, hopefully that was…. Probably not groundbreaking and new, but…

Ed Pizza: Well, I would say, I feel the same in an abstract view. If I were to get specific, and not to pick at things that are controversial in our space, but I would say probably one of the biggest changes I’ve seen, and this maybe isn’t directly to Daniel’s “number one versus 1000…” But if I took a cross section of founders from when we first got back into angel investing, call it back in like 2008, to today, I think they have similarities in all those things that you talk about in terms of their tenacity; the things that they go after, the principles they hold. I think one of the really big differences that I see revolves around their gender, and the color of their skin. I would say that our portfolio was heavily skewed towards white male founders. Even more specifically, white male founders from probably 15 or 20 universities. I think that’s changed quite a bit, definitely not enough, but definitely changed fairly significantly.

I’d say, in any room that you and I go into over the past handful of years, before COVID, I would say that the gender and ethnicity of the room, absent our specific investment choices, is much more diverse than it’s ever been. I’m not exactly sure how to pin that on any one thing, other than to say, us evolving as a culture. Because I don’t necessarily know that the money has really targeted itself towards female founders and minority founders, until just maybe the last two or three years. But I’ve definitely seen, I’d say just since you and I have been out on the tech tour, a huge swing in diversity of the folks that are actively out there trying to create great companies.

Paul Singh: I don’t disagree with anything you’re saying there, by the way. But you know, this topic is actually a really hot topic. You have to go far down the Twitter feed to see people talking about equity and equality, and investor dollars, and all that stuff. Before anybody jumps on the bandwagon here and totally kills me; I don’t disagree with that. We need to fix those things. But is some of that because the historical access to capital was very siloed? It was very like, you had to go to Silicon Valley; this is a cliche, but I’ll just throw it out there to paint the picture. I think part of that is because historically everything was centralized, and because it cost a lot to start a company and all that stuff, you had to be able to get to Silicon Valley and go meet those people on their turf. So obviously to be able to do that, you have to have a certain income already, or financial standing, or come from a family that could support that sort of thing. You could take the risks. You could afford to take those risks.

And now, particularly over the last 15 years, as costs have plummeted… I like to tell people that I think $500 today is the equivalent of $5,000,000 twenty years ago. Now all of a sudden, that allows more and more investors, individuals, angels to participate in deals and actually make a meaningful impact, but also it allows founders to kind of look around the corner, if you will. So in theory, where I’m going with this is, do you think that this is mostly like a… To fix this problem, I think what you have to do is train more individuals to learn how to construct an angel investing portfolio; so that solves, in theory, the capital issue at the local level everywhere else. But then on the other side, teach founders the principles of fundraising that apply at the national level. In other words, train both sides to speak the language of the other. Maybe that’s not articulated well, but…

Ed Pizza: No, and I think we’re on the same page there. I’d say if I were trying to give my prescription, I think it’s largely the same as yours. Absolutely; I think the biggest thing that’s overlooked when it comes to involving more female and minority founders in the investment picture, is making sure that they have the same base of information as the white dude who went to Wharton. So I think there’s absolutely something to be said for carrying that information to founders of any skin color or gender. Not just the fact you’ve got minority founders, but you’ve also got all of the white people that didn’t go to Wharton or Harvard, those folks as well.

So I think there’s a democratization of teaching founders how to source the right investors. Not to go with the overly simple answer, but a friend of mine who’s in the investing space, who’s taught me a lot over the years, said quite simply to me at some point in the past few years, “one of the best ways to increase the number of female founders in your portfolio is to have a female on your team, picking companies.” We all have some level of implicit bias of picking people that look like us, as much as we may try to overcome it.

So I think there’s still a large cross section of white males that control the dollars going into companies. And like you said, this is a hot topic and we’re not trying to take the world off the rails here and solve this problem. But I think it’s just that, that’s a big difference that I see in the portfolio over time.

And it sort of dovetails into something else we’ve talked about. When we talk about educating founders, you Tweeted out earlier this week… You and I haven’t talked a lot about this, but we both agree on it. I don’t remember us having tons of discussions about it, but you talked about founders who overly focus on the valuation, say, at a fundraise. And you talked about price exit as well, which I think is also an issue, but not as frequent, because obviously there’s a lot less exits than there are fundraising rounds. But there’s this thing about like, how founders should… What their “founding principles” should be to raise money?

I think absolutely; I think there’s so many founders who sell themselves short trying to negotiate the “price of their round” when there are so many other important details that they need to stake out, in terms of what their investors are going to get from them, and what they’re going to get from their investors.

Paul Singh: Yeah. I’m in this conversation with founders almost every week. Whether it’s on the investing side and even more recently, on the acquisition side here. Here is the punchy thing that I like to say, “If that’s what matters, you pick the price. I get to set the rest of the terms.” People think I’m being smartass. But the reality is, I’m just trying to make a point. There’s a lot of different levers on that piece of paper, whether it’s a term sheet or whatever. There’s a lot of other levers there and I think people need to learn about that. Depending on how you like to consume information, if you like to read it on books, Brad Feld’s book, I think it’s called Startup Deals, that’s an interesting one that can talk to you about all the different levers there.

I personally like The Archives on Venture Hacks. If you go to, and click The Archives, you can go down into the different sections and stuff like that. I like that, because it’s easier for me to read. It’s such a rookie mistake to focus on price. Whether it’s valuation, or exit, or whatever, because it’s one of 20 things that matter. It’s like, could you have a billion dollar valuation as a startup? Uh-huh (affirmative), for sure, but you’re going to lose all control.

Paul Singh: … as a startup for sure. But you’re going to lose all control.

Ed Pizza: Right.

Paul Singh: That’s the part I don’t get, by the way. That tweet was really triggered by this excitement that happened to be on Twitter that same day, about a big billion dollar valuation for a startup that had raised money. And I’m looking at this announcement and all these founders. Yeah, you could see the employees of that company excited about it. But what really sort of triggered me was all these other founders on Twitter were like, “Wow, look at this. This is so amazing.” And for those people, I just wanted to shake them a little bit and be like, “You don’t understand that what you’re celebrating here as a founder is complete loss of control of your company?” I mean, that’s it. There’s no scenario in which that’s not the case, I don’t think, unless there’s obscene growth, but that doesn’t seem to me to be the case these days anymore. Anyway.

Ed Pizza: Well, I don’t think a lot of companies think about making that choice when they’re taking on fundraising. First off I think, and I have a bias on this that’s probably different than some others, but I think that the convertible notes and safes and stuff like that are used more frequently than they should be. And part of the downside to those I see is that it largely gives folks a pass on defining a lot of those major terms. And I understand in certain cases you sort of have to punt on that stuff for further down the road. But by definition, we’re saying with something like a convertible or a safe that we’re not defining a board and we’re not defining how you can spend money and we’re not defining what sort of control you get. So you can have a mismatch of expectations between your investors and you as a founder.

But I also think back to, and I think we talked about this at some point, but we talked about we had a chance to write a check into a company called Digital Ocean very early on. The founders were actually working on another startup at the time and they ultimately made the decision not to fundraise at that point and they were going to bootstrap further down the road because they wanted a specific level of control. I think that’s not a decision enough founders think about making. Certainly sometimes you don’t have a choice. You need to bring in outside money. But I think there are some things coming down the pike that allow founders and smaller companies to get capital in ways that may not necessarily lose control over the company, if you will. But I think, at least from my standpoint, the amount of shares I’m giving away and the amount of control I’m giving away at a round is certainly much more important to me than the overall “price per share” of what I’m giving away in terms of my vision for the long-term growth of the company.

Paul Singh: I’m going to just say yes. Well, actually-

Ed Pizza: No, you’re not. See? You’re going to keep going.

Paul Singh: Yeah, I was like, “Do I bite? Or do I not?” I’m going to go ahead and bite. I don’t disagree with what you’re saying by the way. But I think… So for me, I’m not necessarily against notes versus equity rounds, that sort of thing. But I do think the common mistake that founders make, particularly with notes, is they don’t quite understand the mechanics. And again, everything you’re saying is true, but I think maybe alongside that, and maybe just as equally important though, I think founders sometimes look at these notes and they’re like, “Oh, it just seems so much easier.” And what they don’t realize is sometimes there’s terms buried in there, like discounts with multipliers and there’s interest rates that, “Yeah, you can have a 36 month term.” But maybe the way the interest rate is written is it’s compounding. And next thing you know, that $50,000 check that you thought you’re converting at a $3 million value is actually accrued more like $120,000 and it had a discount on the three. It doesn’t actually convert into…

I’m not saying that it’s always that nefarious, but the biggest mistake is people don’t understand how those various terms can kind of spiral out of control. They look so innocuous, but they can spiral out of control. You think you just sold 15% of your company when it converts someday, but that’s not actually what happens.

Ed Pizza: Well, and I think a lot of founders don’t realize that convertible notes still, in many cases, based on the way they’re written, are still dead. And that’s where I think other vehicles that are out there that are explicitly much less a “debt vehicle.” But I mean, at the end of the day, a lot of the convertible notes that I see come across my desk are still debt instruments that can be called. And it’s like, everybody at the table all agrees, “Well, we’re never going to call this. We all know the money’s never coming back, but we’re going to use a document that says that we can do that.” And it just is imbalanced in terms of everybody has the silent head shake, like, “Yeah. Yeah. Don’t worry. We’re never going to ask for this money back, but we want you to sign this document that says we can ask you for this money back.”

Paul Singh: Yeah. The thing about that clause though, because yeah, you’re right, it’s in all those clauses. The tricky part with that is that if you call it, the investor does have a brand reputation risk associated with that. So let’s just assume that the company could afford to pay it back if you called it. The intangible, but important consideration there is would public sentiment of other founders be effected? That’s why I think you don’t see it happen very often. Obviously certainly a lot of companies are burning through the cash. So even if you called it, they may not even have the capability to pay it. That certainly is a big part of it. But I think the other reason you don’t see it happen very often is that, particularly for investors that have some sort of brand, whether you’re an angel or VC, the reputational risk is usually far more expensive than the loss of the cash that you already probably wrote off when you wired.

But by the way, don’t get me wrong. I hate to lose money. I’m not saying that I love it or something like that. I’m just saying that it’s nuanced. Anyway, I could keep going with this, but let me pause there. I know we got a lot of topics we want to maybe get through. It’s like every episode we start with this grand vision. We’re like, “Oh, 11 ideas.” I think today’s sheet that that we put together, we got 15 lines on this thing of topics we’re going to go after and we’re like on number two.

Ed Pizza: Well, and we’re never going to get through all of them. So if you had that vision that we were ever going to get through all of them, that’s not the case. It’s more a matter of trying to have enough stuff out there to make sure that we’ve got good segues and stuff that we can cover. So we will never ever get to the end of the list, mark my words. I never use words like always or never and I just did.

I want to ask you a question, and it’s about one of your tweets, because I can’t tell if I disagree. So you tweet about, and I’m going to read it. You said nothing beats face-to-face meetings when building important business relationships. Nothing beats Zoom/Hangouts/video meetings when maintaining business relationships. Yeah. Okay. Give me the 25 cent version now, not the nickel version.

Paul Singh: Okay, yeah. I was going to say, look, you’re dealing with a 200 character limit here, right? So you got to speak in absolutes there. But in that moment when I was writing that, that was actually earlier today, but when I was writing that, I was just thinking as the stakes get bigger and bigger on whether it’s deals, careers, whatever, things get more competitive. The busier client that you’re dealing with or the busier boss or executive you’re dealing with, attention spans get weaker or smaller and smaller, that sort of thing. So point is, is that I think in a world where everybody’s trying to build relationships on Zoom, going and meeting them in person is a differentiator. And I think conversely, or on the other side of that coin, in a world where a lot of people travel to kind of maintain relationships, I think, I think doing Zoom well or doing video on Hangouts well can kind of replace that for you.

So it’s sort of counterintuitive. I guess my point of that tweet was when everybody’s sort of doing one thing, you got to do the other. And I just think that most people think about building relationships online and then only moving the “important” ones to the offline world. And when the majority of people in my view, or at least in my circle tend to do that, I’d like to go the other way.

Ed Pizza: Okay. Yeah. So now I’m not sure if I disagree with you or not. Well, I’m going to tell you my philosophy and you tell me if I disagree with you. And this is setting aside COVID, which has obviously made Zoom and versions of Zoom much more important in how we communicate from a relationship standpoint.

I’ve always been an in-person guy. I’ve also been somebody who frequently picks up the phone to reach out and talk to someone instead of writing an email if I’m going to discuss something that’s beyond fairly straightforward, directional sort of information. And frequently, I’ll have folks tell me, “You’re one of the only people that consistently calls me to have that discussion, as opposed to trying to have it over email.” And I can’t tell whether it’s a good thing or a bad thing, but they keep talking to me, so I’m going to go with it’s a good thing. But setting aside the pandemic, I think overall, I would be in favor of deeper relationships through face-to-face communications, and I lean towards actual face-to-face as opposed to Zoom, as opposed to more relationships that are maintained at a smaller or less deep level by having Zooms and stuff that you will, not having the traditional lunch or breakfast or phone call or whatever.

Paul Singh: I think that’s cool. I think that’s cool. I think it’s not important that we agree on this. I think it’s important that people have a philosophy.

Ed Pizza: Yeah, I agree. I agree.

Paul Singh: Because it does have to be tailored to what you’re good at. To your example there, you like that verbal communication. That’s what you do. I prefer visual. That’s why I kind of joke that I’m always video on. I’m either in person or I’m on video. I don’t even call you. I mean, I feel like I don’t even call you. I’d say we’re going to FaceTime. But I think it’s important that people have a philosophy. Actually on that note, by the way, and this is a very, again, biased thing to me, but it’s so amazing to me for people that are working in roles that requires Zoom or video on a regular basis, it’s amazing to me, 18 months after the pandemic started, how few people have actually upgraded their video setups.

Ed Pizza: Yeah.

Paul Singh: Think about like how much money people spend on… Whether we like it or not, people spend-

Paul Singh: … money people spend on, whether we it or not, people spend money to get dressed up to go to work.

Ed Pizza: Yeah.

Paul Singh: Not old school suits and ties, but a large percentage of the population spends money wearing nicer newer clothes when they used to go to the office, whether it was something casual from Banana Republic or whatever. But then they turn around and they’re working from home and, yeah, I know the joke is everybody’s in their pajamas or whatever, but you were comfortable spending probably 1,000 bucks a quarter on, I don’t know, jeans and fancy whatever. And now you can’t spend 100 bucks on a couple of cheap key lights? Come on. But then they wonder why nobody takes them seriously. They’re like, “Well, whatever.” We’re all fighting a war of attention here.

Ed Pizza: And I think that we’re just starting to come around to what’s a “standard” for a Zoom call. What are typical decorum things? There’s some obvious stuff like you’ve should have a shirt on, but there’s a lot of less obvious things that people haven’t quite realized. You’ve probably dealt with plenty of it. The dogs barking in the background, the kids, the stuff that, and we accept some of that because it was a pandemic, but there’s no really established decorum like there is in an office. There’s no pencil written set of rules for how you’re supposed to comport yourself on a Zoom call and whether you should be visible, whether you should have a good camera, and all that stuff.

Paul Singh: Yes, I agree with that. But what I want to say here also though is that, when these topics come up, they’re also touchy because, of course, what happens is, if we were to talk about this publicly in the open at a conference, somebody inevitably would pipe up in the audience and say, “But it shouldn’t be that way. It should be really about the quality of your ideas or the quality of your work,” and those sort of things. And they’re not wrong when they say that. But humans fundamentally have not changed as we evolved. We do tend to make, for better or for worse, snap decisions about, is this person trustworthy? Do they appear to check my implicit boxes that tell me that they know what they’re talking about? Again, we could debate at another time whether those are right or wrong, but they are instinctively baked into all of us.

And so, I don’t know, the thing I just find really interesting is that pre-pandemic you could clearly see people spent some portion of their budget on a monthly or annual basis to look the way they want to look. And, again, there’s always going to be somebody that’s going to comment on this podcast like, “I wear a sweatshirt.” Fine. You are cool. That’s great. But the vast majority of people still buy stuff. That’s why all these clothing stores are still in business.

Ed Pizza: Yeah.

Paul Singh: So why aren’t you actually spending this? I will tell you, on the side, in one of the upcoming episodes, I’m going to talk to you about a buddy of mine that I’ve been helping on the side. This guy’s an AV engineer for a high level celebrity that everybody has name recognition of, and this is the guy that set up my set up here at home. And I’ve been just setting him up with just a quick, I was like, “Dude, you,” I’m not going to say his name, I don’t want anybody Googling him yet, but I was like, “Man, here’s the deal. I don’t know why you did this all for me for free.” A friend of a friend referred him. I said, “Here’s my setup.” He’s such an expert. He’s like, “Oh, you’re going to need this, this, and this. Here are the Amazon links. And then once you have it set up, call me. We’re going to go do a couple sound tests.” And over the course of a week, we dialed it in all remotely.

And I’m like, “Why didn’t you charge me for this?” And he’s like, “I don’t know. Didn’t really think. I guess I should. But I think the point is, I think that there’s a space here for people like him to target professionals, people that work in the tech or other online industries, industries where they are on Zoom on a more regular basis and offer, “Hey, here’s the $200 option, if that’s all you got, and here’s how you set it up. And then here’s the $2,000 option, if that’s what you want, and here’s how we set it up.”

Ed Pizza: And when you think about how people comport themselves, I mean, you and I are comfortable, we’ve known each other a long time, there are times where you’ve taken my call and said, “Hey, I’m on my way to the store to get diapers for Dana.” That’s cool. We’ve established that relationship. It’s fine. But most people wouldn’t have a job interview while they’re standing in line at Starbucks because they know that that’s not appropriate and yet they’ll have equally important calls based around closing an important client or whatever while they’re on the way to the grocery store or they’re on the way back from picking up their kids. And those are all things we need to do, but I think we also need to understand that there are certain expectations that people form based on those behaviors that are much more visible in Zoom than they might be on a phone call.

Paul Singh: Agreed. And just to point it out, by the way, I’ll just say, just think about how we met. I mean, maybe the rhetorical question is, would we be doing this podcast five, six years after we met in person if we had not?

Ed Pizza: Right.

Paul Singh: In other words, if our relationship as friends and professionals and all that stuff, regardless of where we live or proximity and all that stuff, would we have done as many things professionally together over the last five or six years had we not spent that initial time face-to-face?

Ed Pizza: Well, yeah. I mean, that time that we spent, which we’ll have to get into in one of these shows, was to build a concept that we never actually brought to market.

Paul Singh: That’s right.

Ed Pizza: We met half a dozen time Starbucks to build a business idea that we never actually acted on. Well, I think it was because you bought an RV.

Paul Singh: That’s right.

Ed Pizza: Yeah, so it all goes back to mediocre coffee at Starbucks and a business idea that nobody in the public ever really saw besides you and I. And here we are six years later sitting in our homes with headphones and T-shirts on telling people why we think they’re right or wrong. Who really gave us the right to do that?

Paul Singh: Well, I don’t know, but I think it was an interesting topic that really wasn’t I don’t think on the list before we start already talking, but this idea of pre-pandemic people used to care about how they looked, for the most part, cared how they looked when they were in the office meeting their coworkers or their partners or clients or whatever. And then here we are 18 months into the pandemic and 99% of the people that I still talk to on Zoom professionally anyways are in dimly lit corners. And it’s like, come on, you used to spend 1,000 bucks a year or something on clothes and you can’t spend 200 bucks on cheap key lights? Come on.

Ed Pizza: Right, right. And here I sit unshaven as we finish up this podcast.

Paul Singh: But we can do that because we as peers have spent six years building that relationship.

Ed Pizza: If we actually showed the video to people they might think that we look like, or at least that I look, like a scrungy bum.

Paul Singh: Oh, fair. That’s fair. Yeah.

Ed Pizza: And we left one, two, three, four, five, six ideas on the chopping block that will hopefully get rolled over to next week’s episode when we get a little bit more time. And you said, we might try recording some short feed stuff for quick ideas that we have when we’re either happy or mad at each other about pick any random number.

Paul Singh: I think there’s some merit to that. I think we should think about that, this idea of maybe one or two more shorter sessions on the weekly calendar just so we can riff.

Ed Pizza: And this could be a good time to do it because I don’t think I’m getting on a plane for 10 days, which is a pre-pandemic record for me.

Paul Singh: I was going to say, look at you, lazy.

Ed Pizza: You should see the stack of stuff that isn’t getting done at home. All right, folks, as a reminder, you can find us on Twitter, Facebook, all that stuff. He is @PaulSingh. I am @PizzaInMotion. You can email the show, We’d love questions. We’ll answer them on a future episode, and I’m sure we’ll go way off tangent on our opinions on whatever you write to us. As a final reminder, hit that Subscribe button wherever you are listening to get notified of new episodes every time they drop. Until we upload again.

Paul Singh: That was fun, Ed. Let’s do it again and let’s do it more often.

Who Do You Trust More? Yourself Or Your Employer?

Full Transcript

Paul Singh: I just think that there is a certain amount of personal responsibility that we each have to take for our careers. And I think side hustles are the way to do that.

Ed Pizza: I think many tech companies don’t find a great way to speak to moms.

Paul Singh: Brand is really what people say about you or your company when you’re not in the room.

Ed Pizza: What’s more important than a founder, passion or knowhow? And my answer is, yes.

Hey, guys. Welcome back to the Results Junkies podcast. Paul, is it possible that we’re both home two weeks in a row, recording the first two episodes of the podcast?

Paul Singh: Well, we are, but that implies that we’ve been home the whole week.

Ed Pizza: I don’t think anybody who knows that us would believe that we’ve been home all week. And I think we’ve both been gone in between both episodes.

Paul Singh: That’s right. Yep, yep, yep. Yeah. I mean, travel’s picking back up, that’s for sure. But it is good to be home too. That’s… I don’t even know where I’m going with this, but the point is though, is that, yeah, it’s kind of rare that we’re both home for an extended period of time.

Ed Pizza: Yeah. And we’re… Episode one is in the books. We talked about playing not to lose versus playing to win, which is, obviously one of your favorite topics. We talked about how to plus up your revenue without having a bunch of cash for marketing. So, plenty of good stuff in episode one. What do you think about having one of the books now, man?

Paul Singh: It feels good. Actually, so I did a little sneak preview for my email list last week. Sent them a, for anybody that wanted it, I sent them a Dropbox link to the recording for feedback. So, lots of people actually asked for it. I might have even missed a couple, but there were, I think, something like 120 some people that were like, “Yeah, I’ll listen to it.” And then more emails came in after that and I just hadn’t responded, which is awful. But anyway, that’s the value of that email list by the way, is, if you ever want to get the sneak peek on what we’re working on, that’s where I’m going to post it.

Ed Pizza: Yeah. And so, I’m just trying to figure out what the good news or the bad news here is. [inaudible 00:02:23] the good news is, that I’m obviously subscribed to, to the mailing list and get the emails. The bad news is, I apparently didn’t read it because I didn’t know the episode was, was live, sitting in a Dropbox folder waiting for [crosstalk 00:02:34] to download it.

Paul Singh: I don’t even know why we’re friends sometimes.

Ed Pizza: Mean neither, but we did have the burn last night of me calling at the annual mailing list. So…

Paul Singh: Oh. Well, wasn’t a burn, it was fact. I definitely had not emailed the list in like 200 some days or something like that. And-

Ed Pizza: Oh, was it really that long? Oh-

Paul Singh: Yeah. I actually put it right in the opener-

Ed Pizza: … so, I was really accurate.

Paul Singh: … of the email. I said something like, “Hey, it’s been 200…” I don’t know what the days were, but I’d said in the email, I was like, “It’s been 200 days since I sent you an email, so if you don’t remember, here’s why you’re getting this.” So, anyway. No, but it feels good to have that first episode done. I think, we talked about this a little bit in the last episode, but if you’d asked me a couple years ago, whether I’d be recording a podcast, I probably would’ve said, “No.” But it’s actually been interesting to kind have a chance to kind of formulate these ideas, talk them out. And at least from the initial feedback from people that did listen to it, seemed like it was positive, so I’ll take that.

Ed Pizza: What’s the unsubscribed rate bet on the newsletter, since you put that up? That’s really the test here.

Paul Singh: Oh, I don’t… I’d have to go look. The thing is, a long time ago, I stopped looking at unsubscribes because I think my goal is to force people to unsubscribe on every push. It sounds ridiculous, by the way. But somebody, a long time ago, told me that you have to force people to either love you or hate you. And that’s the only way you’re going to get them to critically think about whatever idea you’re putting in front of them.

Ed Pizza: Yeah. I think that, that’s probably a pretty appropriate way to describe most people that know you or I, that they are equally divided. Maybe not equally divided, but there’s not a whole lot of folks that are in the middle saying, “Yeah, those guys are okay.” It’s either-

Paul Singh: mm-hmm.

Ed Pizza: … “I really love that.” Or, “Man, that was something really stupid that Ed said this week.”, which probably happens more than it should. Anyway, for folks that are tuning in for the first time, and as a reminder for folks that were around for episode number one, make sure you hit that subscribe button wherever you’re listening so you can get notified of our new episodes as soon as they drop. We’re going to feeding off the listener questions for a while here, as we get cranked up. So you can email us show at

And Paul has been lighting up the Twitter. I can’t even keep up. He is @PaulSingh, and I am @Pizzainmotion where you will find me saying the occasional travel stuff mixed in with the business stuff. And let’s jump into some topics for episode number two, man.

Paul Singh: I’m in. I’m in.

Ed Pizza: So, we’re looking down our list today. I got to say that one of the things that you tweeted out last week, which, really strikes the chord of something I’ve heard you say for years, is this whole premise of, there’s this large section of people. And it sort of dates back to my grandfather of, feeling like you’re secure when you have a great employer. And I I’ll paraphrase your tweet, but it was really like, “Who do you trust more yourself or your employer?”

Paul Singh: Yeah. I mean… So, yeah. So I tweeted something earlier this week, where I said that entrepreneurship is less risky than having a job. And I ended it by saying, “Who do you trust more, yourself or your employer?” And the thing about Twitter, as you all know, is that it’s 200 plus characters or whatever, so there’s a lot of nuance that gets lost when you’re just trying to jam into one tweet. But my point with this is, that whether… So, being an entrepreneur is not about what you do, it’s actually how you think about things. So I think for example, the classic, when you think about entrepreneur, the word entrepreneur, the classic thing that comes into people’s mind is. Startup founder, which may or may not be true.

What I’m trying to articulate though, is this idea of entrepreneurship as a way you think. And if you agree with me there, then it’s something that can be applied. This idea of, who do you trust more, yourself or your boss, can be applied to whether you’re starting something, whether you’re in a cubicle at a large company or anything in between. My whole point is, is that I think more people should be thinking entrepreneurially about their careers, about their businesses, about the companies they work for.

And then when you start to think about that really recognize that you kind of have to. Because I think everybody would agree with me that they tend to trust themselves more than the employer, and that’s okay. But then do something about it. And so whether that leads you to a side hustle or whether that leads you to invest in coaching or training for your own career, whatever it means, apply it to your life. But I think entrepreneurial thinking is something that everybody should embrace.

Ed Pizza: Yeah. And I think that in the time that you and I have been on the planet, that’s shifted pretty radically. And it’s interesting in that, I remember when my grandfather passed away, one of the possessions of his that I wanted was a clock that he’d been given by Pitney Bowes [inaudible 00:07:35]. And it had a little plaque in the back about how he had 43 years of service with Pitney Bowes. And I just felt like that was what you did. So I left college thinking, “I’m going to come out, I’m going to get a job, I’m going to work somewhere for 45 years, and then I’ll retire.”

And I had moved onto my second job, like a year after I was out of college. And I sort of bounced around in those sorts of jobs, not realizing that before I went to college, I had taken some of my money that my parents set aside for school and some money that I had saved and I put it into a restaurant I was working in. And I loved it because I came to work every day trying to create something. And I didn’t… I mean, I’m sure I’d heard the word, entrepreneur, back then, back when TV was still black and white and stuff like that. But it didn’t really strike a chord with me. I didn’t really understand it until much later. And I kept going through these corporate jobs and trying to sort of do my own thing and never really understanding that I really wanted to get back to that first thing. And-

Paul Singh: Yeah.

Ed Pizza: … you said something, and we joke about it. Paul and I were on the road together for a handful of years. He came up with this idea to have the tech tour, for folks who may not be familiar with that. And so, I would fly to meet him in places and he’d have his Airstream parked wherever we were going to meet up with founders. And as part of your stage speech in most of the cities, you would talk about how our kids were going to have, not just multiple jobs in their lifetime, but multiple jobs at the same time. And it’s sort of like we’ve pivoted from this thing of, where a side hustle used to be bad. And now it…

Ed Pizza: Of where a side hustle used to be bad. And now it’s almost like people are prioritizing their side hustles in terms of, “Well, here’s my number one side hustle. Here’s my number two side hustle. And if it’s a slow week, then I focus on my number three side hustle.”

Paul Singh: Yeah. What you’re talking about is this thing that I’ve been mentioning to people over the last couple years about how the nature of work is changing. And what I think a lot about is this idea that our parents, like you described there with your grandfather, almost all of our parents worked one job to the arc of their career. For most of us that are of working age… Now, I’m forties, I think I’m a geriatric millennial, or something like that. We’re going to have five or six jobs, or maybe more, but sequentially through the arcs of our career. But I think where our kids are headed, and where the nature of work is headed, is this idea of multiple jobs, and things like that.

That might be a controversial statement, and we’ll see what that means for people. The thing I do want to say is, is that I think that side hustles are an interesting thing. It’s almost if you don’t have a side hustle, people might worry that you’re not growing your skills.

Ed Pizza: But I think the thing is, is that when you look at that, it’s like, there’s this divide I think. There’s people that see side hustles really just as, “Well I want to work when I need money for my next thing,” which I see a lot in folks. [inaudible 00:10:27] “Get off my lawn,” but the folks that are much younger. And then there’s this generation that I think is somewhere in between. And maybe this will filter into our kids’ generation, who the side hustle is, as you said, to develop a skill.

Paul Singh: Yeah. Look, I’m a big believer that everybody should have a side hustle. The primary goal shouldn’t always be money. It could be, but it shouldn’t be. I think you should think about side hustles as a way to gain a new skill, or build a resume publicly, or maybe even make money on the side. The point is side hustle, as a term should not be overloaded, and applied to only making money. I think it is your new resume. It is the way you gather skills these days. Right? And in some cases, could be how you make some money on the side as well.

Ed Pizza: Yeah. When I think of side hustles, as it relates to me, it’s about sharpening a skill, honing a skill that I like. And again, as you say, different things for different folks, I think that there are a number of people who maybe aren’t in love with their day job. And the side hustles the thing that they love to do. Again, whether it makes them a lot of money or not. And I think the pivot for folks, and I think you reference this well, the pivot for folks there is, “Hey, if that side hustle is something that you love, I would challenge you to say, find a way to get somebody to pay you for that side hustle.” Not because you need the money, not because you want to make money, but because I don’t think there’s a better barometer of success than saying, “Here’s this thing you’re really good at, and somebody paid you for whatever that was.” I think it’s the ultimate way to codify that you’re actually good at it.

Paul Singh: Yeah. Yeah. Absolutely. Absolutely. Look, this is a double-edged sword by the way, a little bit. But I think even as an employer now, when I think about the people that I’m recruiting, and hiring, and stuff like that, it’s a double-edged sword because you worry that, gosh, if they have a side hustle, are they going to get distracted from the main job? Or what if one of those side hustles takes off? Will they leave us? And then I got to worry about hiring again. And where I land on this is, is that the side hustle to me is a sign of intellectual curiosity and ambition. And if for some reason one of those things takes off, or somebody else recruits them because of those things, that’s not necessarily a bad thing.

In fact, it keeps the pressure on me to keep their main work interesting, and give them a path to grow. But all that to say, I just think that there’s a certain amount of personal responsibility that we each have to take for our careers. And I think side hustles are the way to do that. That opportunity to have a side hustle didn’t exist for our parents. Maybe it did. “Hey, I work at Pitney Bowes, and I own an ice cream shop on the side.” I don’t know. That may have been what a side hustle could have been back then.

Ed Pizza: It could have been. It was less likely, but I do think that when I first got into the workforce, there was a very prevalent side hustle. I just don’t think we called it by that. When I first got into companies, one of the big things that companies did was they said to you, “Hey, if you find a charity that you’re passionate about, and you want to go out and raise money for them, we’re going to match whatever you raise.” Talk about textbook entrepreneurship. It’s just not how we normally think about it. But it’s like, “Hey, find something you love that you’re passionate about, go find a way to raise some money for it, and as a company, we’re going to support that interest in you. And we’re going to fan that flame.”

Paul Singh: Mm-hmm (affirmative).

Ed Pizza: And set aside the difference in say the benevolence of, “I’m raising money for charity,” to your comment about keeping it interesting for folks who are working for you now so they don’t want to take the side hustle. The principal’s the same. It’s about looking at the folks that are part of your team and saying, “How can I make tomorrow interesting for them?” And the answer might not be with whatever their “day job” is for you, but it’s making sure that they’re thinking about how they can come to work every day, and be empowered.

Paul Singh: Yeah, absolutely. Absolutely. The summary of all that, by the way, is everybody should have a side hustle. Now you can interpret it however you want. For whoever’s listening, interpret that however you want, but everybody should have one, it’s good for you in more ways than most people realize.

Ed Pizza: When we talk about this stuff, this pivots into one of the tweets that somebody sent us a couple weeks ago, Juan Pablo was asking, “What’s more important in a founder? Passion or know how?” And it’s such a short question, but it’s loaded.

Paul Singh: The thing is, I don’t like the word passion being used in any business context, because let me just use an illustrated example. There are a lot of people we probably all know that are passionate about sports, but would be poor. There are no physical…

Ed Pizza: Hockey goalies.

Paul Singh: Well, there you go. Right? Yeah, there’s a lot of people that are passionate about things that ultimately they wouldn’t themselves be good at, because there’s a certain amount of training, and genetics, and things like that are required. In the context of business, passion doesn’t really have a seat at the table. I think of this as a venn diagram, if you’re a founder, and you’re trying to start a company, or you start a side hustle, or whatever you’re going to do, in the context of business, it’s a venn diagram. It’s what you like to do, what you want to do, and what other people actually need. And in the context of business, the overlap of those three circles is really what you should be doing. And tying back to the original topic, side hustles allow you to increase those bubbles a little bit, and potentially increase the overlapping area there. But passion, I don’t think has a seat at the table in the context of business.

Ed Pizza: Yeah. And I think I read the question differently than you did. And I’m going to disagree with you on points. I think we’re pretty close on this, but for me, the question is, as Juan Pablo put it, what’s more important in a founder, passion or knowhow? And my answer is, “Yes.” And I’m thinking about this from an investor standpoint, there’s no question that skills are a huge part of it. I think about when we go back, and try to figure out why certain investments fail, a lot of times it’s because the founder just wasn’t connected to whatever the vision was. I’m going to flip that around the other way and not try to talk the negative, because I do that a lot, but I’m going to use an example of a company that we didn’t invest in.

And I don’t remember why we didn’t invest, but then I tried to invest later, and the name of the company is, “Revelar.” I’m not going to remember the name of the founder, but I remember her story, and this probably goes back 10 years ago. She created this device that women could wear while they were jogging that would track their running, and would also act as a panic button to call 911 if something happened. And this was obviously before other devices that we had, Apple Watches, and Fitbits, and stuff like that, all did this stuff for us. And the reason why the company succeeded initially, the reason why…

Ed Pizza: Reason why the company succeeded initially, the reason why she got a lot of traction in my opinion was because of her passion, it was because, as I remember it and I sure hope I don’t get this wrong, her sister was mugged while she was jogging. And so there was physical harm to someone that she loved and she really had a passion to figure out how to fix this. And she really wanted to make this better for other women. And I felt like, I think where she ended up going with that, the arc of the company as I recall, is she had the passion, and at some point she had to know how to know that she wasn’t the right person to run the company, and she went and found a new CEO. And so I think that without having both of those things intermingled there, I think you end up drifting away from the reason you got into it in the first place.

Paul Singh: I don’t disagree by the way but again, back to the-

Ed Pizza: I didn’t think you would.

Paul Singh: Yeah, back to the concentric circles though, that’s what you care about. Like, passion to me is driven mostly by emotion, and in some cases with certain entrepreneurs, a little bit of delusion. And to me, it’s really about what you care about, in that context she cared about the fact that this happened to her sister, and that drew her towards this problem space. And maybe I’m splitting hairs here, and I know we’re not disagreeing, but I do think words matter. I think that as a species, words are how we communicate.

Ed Pizza: Species?

Paul Singh: Well, even it’s how we communicate with each other. But it’s how we, even in our heads, when we talk to ourselves, the words we use. It’s the difference between when you ask your kid, how was your day? Versus, tell me your day. Both of those have the same spirit, but one of those sets you up for a one word answer, and the other sets up a conversation.

Ed Pizza: Oh, for sure. And I think both with children and founders alike ask asking the wrong question is so critical. And you learned this really early on in parenthood.

Paul Singh: Yes.

Ed Pizza: And you’ve learned it very early on in terms of interacting. And I don’t think this is just, I’ll be honest, I don’t even think this is really just an investor/founder sort of thing in terms of me seeing a founder.

I think when I look at folks that I want to partner with on things and I dig into stuff with them, it’s not too dissimilar to my kids. As you say, if I set them up for the one word answer and they give the one-word answer, I think it’s a great barometer into that passion level. And so it’s prompting for that right answer if you will. But again, that people, I think that if you ask someone who’s really passionate about whatever it is they do, and they happen to be skilled at it too. And you ask them the basic question like I asked my ten-year-old son and get the one word answer, how was your day? I think you’re going to get a great answer from the person whose skills are sharp and and they’re looking at how to 10X their business because they want to scream to everyone about what’s succeeding and what’s failing.

Paul Singh: Yeah. I mean, on the investor side of this, I would say that for me when I’m thinking about let’s say a B to C company in terms of, does this founder care enough? And fine if we want to use the word passion like, are they passionate about it? I would say, I want to know what is it about the current systems, or things that they were experiencing? Like, what is it that made them want to start this thing? Is it a repetitive problem they were dealing with? Is it something that happened to their sister? That sort of thing.

And on the B to B side though, I think it’s typically more about domain expertise. So in the context of B to C, I think I’m looking for a first-person relationship with whatever the problem space is, whether it was something that happened to their sibling, or something they deal with every day. And when it comes to a B to B company that I might be investing in, I look for domain expertise. Why is it that this person has decided to solve this problem? And then, what qualifies them to do this? Because there a certain amount of domain expertise required in the B to B space.

Ed Pizza: Yeah, for sure. And when you think about that, when you think about the connection, it’s funny because this was something that I was going to lead the show off with, and partially to needle you and partially to commiserate, though I’ve never been through it myself, but so your wife’s Facebook account was hacked recently, and I think the interesting thing here, when you talk about expertise and that personal connection, we’re both old enough to remember MySpace, and I’m sure there are people listening who maybe have heard the name, but weren’t a part of it. Look, I mean, for the majority of the life of a large chunk of millennials, Facebook was, and has been, and is the primary way they communicate with a lot of their friends.

And when I think of things like what you’re dealing with right now, in terms of trying to get her Facebook account online, and trying to figure out what happened, and all that stuff is like, there’s going to be a time at some point in the future where Facebook isn’t going to be the center of our universe. I don’t know if that’s before the next president is elected or if it’s five presidents from now, but I think you and I both know that someone’s going to come along and see the sorts of things that you’re having problems with, whatever it is. And maybe it’s not this specific problem, but they’re going to have a friction, they’re going to say, “Well, damn it. I want to go start… I need to make this better.”

Paul Singh: Well, yeah. I mean, a lot of great companies have started that way, right? They look at the public customer complaints about whatever the incumbent is and then build a company off of that. In the context of like Dana’s Facebook hack, there’s that personal aspect of like, “Wait a second, did we lose 15 years of stuff?” As an example, the announcement of our kid’s birth, we didn’t, because of whatever, people don’t send birth announcements as often, right? I guess, so it was like, what about the comments on those posts? That was the personal loss that was felt while the account was down. But then professionally one of the challenges was, well, wait a second, she’s listed as an admin on a bunch of our portfolio companies, and were the ad accounts attacked, or hurt, or anything like that?

But my tweet the other day about it was really more frustration about the fact that the overall process, like if the whole point… like Facebook, and don’t quote me on this. But for the last I read, like Facebook, when they do their public earnings reports, and stuff like that, a lot of the KPIs they talk about is related to how engaged the average user is, right?

Ed Pizza: Yeah, dwell time. Yeah, absolutely.

Paul Singh: Okay. so here’s the part that really pissed me off and what drove that tweet that I threw out there, was that on the one hand they want to use a KPI to the public market investors about how engaged their users are, on the other side of it, when those accounts are hacked, even if they’re small ones, or big ones, or whatever, the recovery process says vague things like upload your ID, we’ll be in touch in seven days. And to me that’s weird, how is it on one side of the equation? You’re publicly and privately building systems to engage people and sit on there for hours a day, or whatever it might be. But on the other side, the minute those users have any trouble, now all of a sudden it’s like, we’ll be back in seven days. Now I don’t know what the right solution is there, but that gap between how often I might be on it versus how often your support team might get back to me, that feels strange. It just feels really strange to me.

Ed Pizza: Well, and I wonder, without getting overly philosophical, if that has something to do with the vision of the founders. So if you think about some of the detailed stuff at a place like Amazon, versus Facebook, and how Zuck and Bezos have taken very different tactics on how to get to where they want to get in terms of managing the vision. And not that I’m not that I’m Zuck or Bezos by any stretch of the imagination, but I’ll talk about something that we’ve had as a principal of every company that I’ve worked in, that I’ve had decision-making power in for 20+ years. And that’s with customer interactions we have a hard and fast rule, and we break it frequently, but the rule always exists, and the rule is if a customer reaches out to us we get back to them within 60 minutes.

And I don’t care if it’s a compliment, I don’t care if it’s a complaint, but the customer took the time to reach out to us. And so we have a 60 minute rule. And like I said, we break it frequently because of life and all the other stuff. But everybody knows our standard is we’re going to respond to our customers in 60 minutes. And I’ll tell you, we actually win back so many customers whose line is, “Wow, I didn’t actually expect to hear from someone.”

Paul Singh: That’s right.

Ed Pizza: And this ties back to your comment on Facebook of like, we’ve been preconditioned with a lot of these products that we use that are quote unquote “free,” where in a lot of cases we end up being the product, that the customer service level is going to be crappy. We’re going to get in customer service what we pay to use the product-

Paul Singh: Yes.

Ed Pizza: … which is little to nothing. And I think we win…

Ed Pizza: And I think we win frequently because we exceed the customer’s expectation when something went wrong and said, “Hey, getting back in an hour. Sorry about that.” And people are surprised because they’ve been conditioned to think that they’re going to lob this complaint and it’s going to make them feel good while they’re typing it because they’re getting their frustrations out, and then they’re never going to hear anything again.

Paul Singh: Mm-hmm (affirmative). I know this isn’t on the list today, but on this note, it sort of brings up this point that I’ve been thinking about more and more the older I get, unfortunately, is this idea that brand is important in business and in your careers. And what I mean by that is, is that a brand is really what people say about you or your company when you’re not in the room. I mean, that’s the most simplistic view of it.

Ed Pizza: Yeah, absolutely.

Paul Singh: Right?

Ed Pizza: Yeah.

Paul Singh: And so when you think about, in the context of customer service, product differentiation, like all these things that people try to differentiate on, whether it’s price, product, whatever, are really temporary because there’s always going to be somebody out there that’s going to under-price you or whatever. And so when you think about like, why do we buy … this is a bad, cliche example, but why do we buy Nike versus Adidas versus whatever? It’s because it’s how it makes us feel.

In our business, for example, on the Bump side of things, we have this metric that we look at is average response time. Our customer experience team is not measured by how many minutes they might spend on the phone. That’s not even on the metrics. I mean, I don’t even think we … it’s probably in the database somewhere. We don’t look at it. We look at average response time. What is the average initial time from when a mom contacts us via email, text, or SMS … or phone to when she gets that first response and you’re right. I would love it to be instant, but the reality is sometimes there’s an all hands meeting and nobody’s going to be on the phone, or somebody might respond or email us at 11:00 PM on a Friday night. It’s possible they’re not going to hear anything until Monday. But we want those to be the exceptions, not the rule.

And I think that’s to your point though, some of these larger companies, I think, lose sight of that. I was on my standup with my leadership team this morning and one of them said something interesting of like, “God, there’s all these like big companies like MailChimp has just got acquired for $12 billion and there were these other … ” Anyway, we were just talking about like, God, those companies, there are so many … as users, like MailChimp, I’ve shifted away from MailChimp a long time ago personally, because I thought the software was clunky. But hey, it’s still worth a lot of money. That’s awesome. And it was like, God, maybe that’s terrifying and amazing at the same time.

Ed Pizza: Yeah. And Paul, when you talk about those sort of metrics with a company like Bump, with what you guys are doing, I’m biased here because I watch my wife. But the way her life is scheduled every single minute, every single gap of the day, as you mentioned with your core customer, which I think many tech companies don’t find a great way to speak to moms, they’re sitting here in this space where they have time to get something done, and when you take them off path that kinetic energy goes somewhere else. And you don’t know when they’re going to come back into your solar system. So I think understanding that that’s your core customer and that you have to engage with them quickly is so important in recognizing that it’s not just that mom needs the products that Bump Health is selling, but she needs a different type of service to be engaged in the sort of life that she’s leading on a daily basis.

Paul Singh: Well, yes. I’ll just say yes, but where this takes me, and this might be its own podcast episode at some point, but I’ll just say that where this takes me is you have to recognize that they’re … today’s consumers, whether they are managers at another company or that mom at home, whatever, they are digitally native. They’re not digitally savvy, in the sense that like digitally savvy to me is different than digitally native. Digitally savvy is like they learn tech and they’re cool either way. But digitally native is like, “Hey, it’s kind of weird when you call me. I like text.” It might be different for different demographics, but it might be like, “Hey, I only do video conferences or video FaceTime or whatever, I don’t do phone calls,” or vice versa. It’s different.

So back to where you’re going with this, I think you’re right. If the business is not adapting to the customer’s lifestyle, then there’s probably, at some point, may not be soon but at some point, an opportunity for somebody else to disrupt that. And I think it’s something to think about whether you’re on the business side or you’re sitting on the entrepreneur side. But you’ve got to communicate, the business has to communicate the way the customer wants it to, otherwise somebody else will get in there because there’s just too much friction. Customers today are, fortunately or unfortunately, fickle. So anyway.

And know we’re jumping all around here, but I’ll just say, this brings me to something else I tweeted about this week, which was, if you’re unsure what to build, right? If you’re unsure what to build, what you should do is look at a company that’s in whatever space you care about, particularly look for companies that are over 10 years old, probably over 100 employees, because that tells you that there’s enough staying power, enough revenue to have that staying power. If you find that company, what you want to do is number one, re-imagine it with a deep understanding of it. Like what would that business look like if it started today with a deep understanding of today’s technology? Number two, and to what we’re talking about here, think about what it would look like if that business started today with a deep understanding of today’s digitally native customer, which is true by the way, B2C and B2B. And number three, what would that business look like if it started today without any legacy baggage of the last 5, 10, 30 years of stakeholders and code and compliance or whatever it is? And whatever that is, could be an interesting business to build. I mean, that is the framework I use to keep adding businesses into Bump Health.

Ed Pizza: You’re literally like previewing where we’re going to go next. And that’s … this should be a full, full episode, talking about breaking all that down. And I think that’s a great place to tie us off and say, we want to dig into that super deep, I think going through some of the thread that you put out on Twitter there of the bits and pieces of what you guys are trying to build. I also think we need to get back to some of the stuff that we didn’t get to cover this week that talks about, hey, how has the role of a founder changed over time? I think it was a great question that came in and probably paraphrase the question when we try to answer it. But I think, being an entrepreneur has changed structurally in just the time that you and I have known each other in terms of how to go about things, in terms of … like using your example of how you guys are going about it with Bump. But I think that’s a great place for us to tie it off and say that we’re going to try and pick this up again next week, when both of us have probably already gotten on airplanes again and are back in the same seats.

Paul Singh: Absolutely. And here we are in episode two, had grand ambitions of covering what is this, seven, eight topics? And we covered three, and half of them were weren’t even on the list. So I don’t know if that’s like the … what it? The premonition of what the future looks like or whatever, but we’ll see what the audience says. I mean, if you got comments, good, bad, ugly, you can either flame us online, on Twitter, it’s Paul Singh or Pizza in Motion, or just email Both Ed and I are keeping an eye on that. But criticism welcome, heckling welcome, or compliments. I always love a good compliment.

Ed Pizza: Yeah. The compliments are so boring, but yeah, the best thing you can do is tweet us-

Paul Singh: Speak for yourself. Speak for yourself. I love those things.

Ed Pizza: So tweet at us, as Paul said, shoot us emails, that stuff. We love reading your name off on the air and talking about whatever it is that you think that’s important, that’s burning a hole in you being able to get over that next hurdle. Like Paul likes to say, all that hand-wavy and fluff stuff is probably on some other podcast. So we’ll have plenty of results and plenty of tactics for you guys again next week.

Playing To Win vs Playing To Not Lose

Full Transcript

Paul Singh: The biggest money to be made over the next 10 years, is at the intersection of the online and offline world.

Ed Pizza: Somebody sitting in a room programming isn’t necessarily going to have that context of having banged their shins against that specific thing, a million times.

Paul Singh: Biggest mistake I see a lot of early stage founders make, whether they’re funded or not, is they just try to boil the ocean.

Ed Pizza: When there was a huge inflection point and somebody decided that they were going to… That was when they were taking the left-hand turn, that there was some real massive company growth.

Ed Pizza: Hey guys, welcome to the first episode of The Results Junkies Podcast. Paul and I have been threatening to hit the record button for quite a while. And we finally got around to cranking out episode number one. And Paul, I’m going to steal your line right off the bat, to just remind people that the show is all about tactics.

Paul Singh: Yeah. I mean, there’s just plenty of stuff out there for hand-wavy, unproven, unused advice from unfortunately, unqualified people. Between you and I and our investing in our operating of companies and stuff like that. Yeah, we need tactics to keep doing what we do and now we’re sharing them here on the podcast to help others.

Ed Pizza: I would have lost a bet, had we made a bet that you would have used the word fluff in the intro, because along with hand-wavy, hand-wavy and fluff is right down your wheelhouse. So, I guess we’ll get the fluff a little bit later on. Huh?

Paul Singh: Well, maybe, maybe, yeah. Don’t get excited. But, I think that the older I get, I think, the more cynical I’ve become and when I see BS and… So, now I’ve spent the last couple of years weeding through it to figure out how to build my company, and weeding through it to figure out which companies to invest in and how to sort out what’s real and what’s not. But, now it’s, all the stuff you and I have learned over the last couple of years Ed, let’s just start talking about it. And somewhere out there, I’m convinced that there going to be smart people that can use this to further their careers, or their companies, or their businesses, or whatever. So, it’s going to be great.

Ed Pizza: And we did talk about it. So, in episode one, we covered some listener questions. We talked about whether it’s better to raise money, or bootstrap. I mean, this question comes up all the time from new founders. We dug into how to acquire customers to get from zero to a million bucks in revenue. Again, another question we hear all the time. And we touched on one of Paul’s third rails, playing not to lose, versus playing to win.

Paul Singh: That’s right. Yeah. I mean, I think it gets me fired up and I think you’ll hear it in the episode, but I just see so many smart people accidentally, playing not to lose. And in the episode, I talk about a couple of examples that should help you figure out when you find yourself, or somebody you know, doing that. So, you can hopefully pull them out of it and get back to playing to win.

Ed Pizza: Awesome. Well, we are going to play to win and get out of our own way and get ready to start episode number one. As a reminder, hit that subscribe button, wherever you guys are listening to get notified of new episodes, as soon as they drop. We’re going to be feeding off of your listener questions as well. So, email us, You can hit us up on Twitter as well. Paul is @PaulSingh and I am @pizzainmotion. On the other side of the music, Paul and I, Result Junkies, episode number one.

Paul Singh: Let’s just get right into it. This is the first episode of the podcast and I tweeted about it the other day. And I mean, the understatement of the day is, I was just blown away by how many responses came in. And like you said earlier, right before I hit the button to thoughtful ones, thoughtful questions. So…

Ed Pizza: Well, I think we had hit the button. I think that was take number two. But, yeah, people wrote paragraphs, which I think is awesome that they took the time to think about framing the question.

Paul Singh: Yeah, for sure. For sure. So, all right. Well, we’re going to figure out how this show is going to flow, over the course of the next couple episodes. And I think, if you’re listening to this and there’s ideas that you think might make the show more interesting, or ways we can make, or frame things better, send that over. The best email for that, is going to be And well, let’s get right into it. Ed, I know right before this, you and I cherry pick all the ideas into a doc here and there are in no order of favorites, or anything like that, but let’s get right into it. I’ll give you the courtesy of picking the first topic of the first episode.

Ed Pizza: Wow, courtesy from Mr. Singh. And I’ll say yeah, everything that came in got put into the Google doc. And I would imagine we’re going to answer all of these questions over some handful of episodes. Because, they’re all great ones and I would say, there’s at least 30% of them that you and I are going to fight about. But, for startups, I think our first question is something that we’ll likely, mostly agree on. And so, Rigerio writes in, “When starting, is it better to bootstrap, or aim to raise funds from investors?”

Paul Singh: Yeah. I mean, it’s such a simple question, but it’s very nuanced. I don’t know. I mean, the unfortunate answer is, it depends. I guess what I would just say, is that when you bootstrap first, you always have the optionality to raise money later, but the opposite is not true. The minute you raise money, you can’t easily go back to bootstrapping. Now, before anybody listening to me says, “Well, but Buffer did it, or Gumroad did it.” That is true, founders have been able to undo it, but I will just tell you, at least in the scenarios I’ve seen, it’s not cheap and it’s certainly not easy. So, all that to say, if you’re looking for a simplistic answer, just remember that there is no simplistic answer, but it’s really about optionality. Bootstrapping first, retains the option of raising money later. But, the opposite is not really true.

Ed Pizza: Yeah. And I think you nailed it. No question about, it depends. But, I think you nailed it when you said that it’s really, really hard to unwind that equation. Once you’ve rung that bell, as Paul likes to say, “You’re on that treadmill.” And I think, the other thing I’d say for anybody who’s out there looking to start a company, trying to figure out if you can do it, is much more important than trying to figure out if you can raise money against it. Because, I believe at this point that there’s an investor for every single founder and there’s probably six investors for every founder, just based on how much money there is out there right now. But, you’ve got to figure out if you can do it. And I think if there’s a bunch of money in the bank, you just don’t have the hunger and the motivation to try and figure out how the heck do I get this done? Somebody will give you money if you figure it out.

Paul Singh: That’s fair. I want to just add though. I think that, whoever the PR people are for the venture industry, I mean, clearly they’re very good at what they’ve done, because I think what’s happened here. You know, if you look at entrepreneurs on the coast, all around the world, whatever. Everybody thinks they have to raise money and I get it. You don’t have to go far on any social feed to see that everybody celebrates people that raise money and you don’t have to sell… Yeah, anyway, here’s my point. The thing about money is, it’s like rocket fuel. You can put the rocket fuel in the… Oh, God, this is such a bad analogy, but I’m going to use it anyway. But, the problem with money, is it doesn’t actually make anything better. If the rocket’s pointing in the wrong direction and you put some gas in it, it’s still not going to go where you want it to go. What does it take to get the company pointed towards customers with small but meaningful traction?

Ed Pizza: Well, and I think, you hit the nail on the head again with, if the rocket isn’t pointed the right direction, that fuel isn’t going to do any good. Where money can help in these situations, is that money is absolutely going to help you fail faster and pivot, than if you’re bootstrapping in a lot of cases. But, that money comes with consequences. And so, you’ve just got to think about whether you’re ready for those consequences, or whether you can find a way to fail quickly without the money. Is there a way to test it in a small enough group setting that you can figure it out and fail without taking money? So, that when you do take the money, the rocket’s pointed in the right direction.

Paul Singh: Yeah, that’s fair, that’s fair. But, not to belabor the point, but you hit on something, I think, that’s an important thing to at least touch on. The startup community does talk quite a bit about pivot, “Oh, just be ready to pivot. Startups, pivot fast.” I get it, there’s books written about pivoting now. But, the thing to understand about that, is that sometimes it’s easy to pivot when it’s just you, or your team, or whatever, but the thing about it is on the investor side, if you pivot, that’s also a little scary for investors too, because they invested in idea X and not to say that they don’t understand that a pivot could happen, but I think it’s just important for a founder to understand that, as much as we glorify pivoting and I agree by the way that pivoting that founders and startups should be ready to do, let’s just not forget to at least mention, especially when you have investors, with a pivot does come, some additional discussions with an investor, because God forbid you pivot into another company, or space they’ve already got a conflict in.

That does happen. I mean, you can Google it. That’s happened at very high profile firms. But also, there may be cases where you pivot into a space that, that investor does not want to be in. There’s a lot of things that happen there. And I’ve been doing this stuff for 15 years now, and I’m telling you the dark underbelly of the pivot, is that it does make investors uncomfortable. And more often than not, they’re probably going to just go ahead and write the investment off. [crosstalk 00:10:41] What you read about is, “Oh, the successful pivot.” But, that’s just success bias, or whatever they call it, right? Or, confirmation bias.

Ed Pizza: Yeah. And that’s the thing I wonder, because we’ve never tracked this. At least, on my side, I’ve never tracked it. I wonder if somebody has statistics on the success of companies after a pivot. Because, like you say, we hear about a lot of pivots that are successful and yet, I could sit here right now and I take my shoes off to count all the companies I know who sent me an email saying that they were pivoting. These are companies that we had investments in, sent an email that said they were pivoting. And then, the next email from them within 90 days was, “We’re shutting down.” So, definitely have piles of both. I don’t know that one’s necessarily, more successful than the other in our landscape.

Paul Singh: One of the other things you touched on there, I think that is important, but not mentioned publicly quite often is, when you think you might have to pivot the thing you really ought to think about is, is it better to just stop?

Ed Pizza: Yeah.

Paul Singh: And maybe give the money back? And I know that’s uncomfortable, but just hear me out for a second. A lot of people are going to hit the stop button and move on to the next podcast where… But, hear me out for a second, look, the arc of our careers is long. We’re all going to be in this industry, or somewhat we’re doing it, right? We’re all going to be of working age. There’s 40 years of our…

Paul Singh: Somewhat, right? We’re all going to be of working age, there’s like 40 years of our lives. So if you’re thinking about pivoting, I’m not saying you shouldn’t pivot. But I do think that when you look at whatever your decision framework is to make that pivot, one of the angles to consider is, is it better actually to maybe stop and unwind the business right there, return whatever money you possibly can to investors and get the goodwill that comes with that? And again, I’m not saying you shouldn’t pivot, but I think it should be one of the angles you explore before you turn that ship. Because to your point, more often than not, you get the email about the pivot and then 90 days later you get the secondary email of, “Sorry, we’re wrapping it up.”

Ed Pizza: So how many times have you gotten the check back in that situation, more than 10?

Paul Singh: Oh man, honestly, no. I would say somewhere between five and 10 companies in the last 15 years. Yeah, but I think it’s because we don’t talk about that as an option.

Ed Pizza: Right. Yeah. I think I can recall two, significantly less fewer investments than you over 10 years. I can recall two. So you’re right, it doesn’t happen very often. They run until they can’t run anymore.

Paul Singh: I mean, that’s the whole point of this podcast, right? Is that I think that there’s a number of topics across a number of concepts, whether it’s funding or careers or growth or business building, that nobody really talks about. Hey, we just hit on one in our first episode, that’s great.

All right. So Monica asked, “How do you acquire customers on a budget from zero to a million in revenue?” Look, I love this question because I think the reality is that as much as we all talk about building the next big thing, if you can’t get from zero to $1, you don’t have a business. And if you can’t go from one to a million, you’re never going to get to that other thing. So look, I don’t have a very sexy, complicated answer here on my end and I’m curious where you’re going to go with this too. But on my end, I think that at a high level, zero to a million is about brute force. But again, hear me out, it’s not about boiling the ocean either. I think that … Let’s just assume that most of the people … Let me just make an assumption that most of the people listening to this are in some sort of business where they’re going to acquire their customer online, which I realize, by the way, is not every business, but let’s just make that for now.

If your customers are online and you’re trying to go from zero to a million dollars, it is going to be pure brute force. But before you do that, I would say, you need to install three pieces of software on whatever site you use. I don’t care if it’s Shopify or WordPress or whatever. Whatever it is you use on your e-commerce or SAS or whatever site it is you need Google Analytics, you need Google Optimize and you need a tool like Lucky Orange.

And here’s what I mean by that. Google Analytics, not rocket science, but people don’t use it well, understand what UTMs mean? Google that, learn it, it’s a very simple concept. With UTMs and you’re basic understanding of it, you will have what they call attribution. You will know where people are coming from and if they purchase something really where they came from, what they did, that sort of thing. We’ll skip over Google Optimize for one minute.

Lucky Orange or a tool like it. I use Lucky Orange every day and my business is at 40 mill and growing, right? So Lucky Orange, and there’s many other tools like it but I love this one, Lucky Orange is site recordings. They have a lot of other features, but the feature I use almost daily is user session recording. So once they come into the site, which you can see on Google Analytics, then you’re actually recording the entire session. Now you can’t see where that user’s eyeballs are going or whatever, but what you can see is where they’re scrolling, where their mouse is hovering, that sort of thing.

And then that leads you to the third piece of software, which is Google Optimize, which allows you to change things on the page without having to be technical. So let’s just say, as an example, you see a lot of traffic coming from a Reddit post you did. I’m just making that up. And that traffic comes in and like an hour later, you can go into Lucky Orange and you can say, “Okay, show me all session recordings from that source during that time.” And you can just watch them.

Now that may not sound interesting, but if you watch them enough, you’ll start to see where people get hung up. And maybe it’s because the … You’ll see them hovering their mouse over some copy, that’s confusing. Or maybe you’ll see them rage clicking. They’re trying to click that checkout button, but it’s not working. That’s fresh on my mind, by the way. But now that allows you to go back and say, “Okay, before I go Re code something, let me actually use Google optimize to change that section of the page and see what the next set of traffic does there, do they still get hung up?”

So, all that to say, to go from zero to a million in revenue, it’s about brute force. It’s about setting up the tools that you need to know where people are coming from, what they’re doing on the site, and then change that experience for them on the fly.

And then beyond that, the last thing I would say is, it’s about not being romantic about how you make your money. Look, if you’re trying to go from zero to a million dollars, I’m going to guess it’s just you working on your business. Maybe it’s you plus five, but it’s still a small team. You got the same 8, 10, 12 hours a day that I do. Use Google Analytics to figure out what you think the top three channels are going to be. And if you’re going to brute force it, nothing but those channels. That’s it. And you’re probably going to want to stick with that, well past a million bucks. So let me pause there. I’m curious what you would say.

Ed Pizza: Yeah. I don’t know. I think you have some great experience right now with pieces of software, like Lucky Orange. So, I’m not going to try and stick a better pin in that. I will say that I agree wholeheartedly on Google Analytics. Short version along with the day job, I write a travel blog and I’ve been writing that travel blog for almost 15 years now. And when I started, I didn’t even have Google Analytics installed. I would get these spikes in traffic and it was like, “Wow, that’s great. I got a spike in traffic.” But I had no idea why. And so I think Google Analytics is the first taste that a lot of people are going to get of the who, the what, the why, the where, and what you do with that information after that. I mean a bunch of different paths, but but I agree wholeheartedly with Paul that Google analytics is a great way to start explaining to you what’s happening on your website.

And I think to your point, Paul, even folks who have quote unquote “brick and mortar businesses,” they’re going to acquire vast majority of their customers from a website or from social media or something of that nature. I think in the zero to a million dollar category, I think the other thing I’d say, if we zoom out, we go to that metaphorical 10,000 foot level, I think what you want to do at that point is find the people that you know the best, who are the ones that always tell you when you have something stuck in your teeth. And try to pitch them on whatever it is you’re selling and have them tell you why it sucks and why they’re not willing to sign up.

I’d also say too, for anything that’s subscription-based, I would introduce it to people that you know. Because I think if you want a classic sign of early failure or early product market fit issues, if you have a product that you know that you highly believe that your friends will use and you show it to them and they don’t sign up and give you five bucks a month, you really have a messaging issue.

Paul Singh: Yeah. Yeah. I can’t disagree. I just think that ultimately it’s about brute force. And the biggest mistake I see a lot of early stage founders make, whether they’re funded or not, is they just try to boil the ocean. We’ve glorified this idea of hustle porn, working 27 hours a day and all that and that’s not how real great companies go. I think it’s about being realistic and saying, “These are the three channels,” or “These are the three things I’m going to try.” And you may be wrong, but don’t try channels four, five and six until you sunset channels one, two and three.

Ed Pizza: No, I think that’s a good point. Even if you’re going to work 27 hours a day, you’ve got to hit two or three things and hit those things incredibly hard to get your reps in, to see if they’re the right thing for you. As opposed to, like you said, “Trying to boil the ocean.” No question at all, 100% agreement.

Paul Singh: That’s right. That’s right. By the way, I know that for sure, somewhere in the audience, somebody because … So, I tweeted about this a couple of days ago. I said like, “Attribution, that is the only way, that is the number one thing you need to understand to get from zero to a million in revenue.” Oh man, here come all the tech nerds. “Oh, Paul, that is so obvious.” That boils me or riles me up because look, if you have built a web company before, this is obvious to you. But my experience and I think, Ed, you would agree with me on this, my experience of having invested, I think now across almost 60 countries and almost every state in the United States is that, the tech bubble is actually very small, very small. The people that really need to understand what I’m saying here is the people that have never stepped foot in Silicon Valley, the people that are just starting.

So, before all these tech nerds start blowing me up on Twitter, just understand that, look, the reason we have grade schools and high schools and all these colleges around the world is not because … It’s for no other reason than the fact that knowledge that people need is not actually innately known. We all need to know some math. It is not innately known, so that’s why we set up schools. We need to know how to write. It’s not innately known so we set up schools. And same thing here.

I really think the biggest money to be made over the next 10 years is going to be, at what I call, the intersection of online and offline. The biggest money to be made over the next 10 years is at the intersection of the online and offline world. And what I mean by that is, it’s at the intersection of technology pushing its way further into the majority of industries on this planet that still have not seen massive innovation.

So, think about what Silicon Valley and SAS and B2B and consumer startups have done over the last 20 years, they’ve made a ton of money. We’ve made huge platforms. Facebook didn’t exist 15 years ago. You TIK TOK didn’t exist two years ago. Those are all, all joking aside, amazing. They’ve allowed people to connect. But let’s just be really clear,, the vast majority of money spent on the planet is still in the real world for better or for worse.

Ed Pizza: Yeah, I think a lot of the people that we met on the tech tour were folks that had figured out how to solve a problem, but didn’t have any of the tech stack side of it. And they had lots of customers and they were doing things manually, shipping, stuff like that or how they were acquiring customers. Well, heck, actually probably our first investment on the tech tour, Jetpack. His goal was to find accountants and sign them up for his time management system. And accountants, they’re not Twitter folks. These are not folks who are hanging out in sub stack Reddits and stuff like that. These are very black and white people and he had to figure out how to connect with them where they were.

Ed Pizza: … black and white people, and he had to figure out how to connect with them where they were.

Paul Singh: Well, I don’t know if David would appreciate us talking about him, but let’s talk about him, and then maybe I’ll get in trouble here. But, so David Cristello from Jetpack Workflow, we met him … I guess it must have been four years now, four years ago now. And long story short, we ended up investing almost instantly. And then I think over the years … I have to look it up, but we’re probably in there about a half a million bucks at this point.

Ed Pizza: Yeah. And four or five times.

Paul Singh: Yeah. Four or five times. Yeah. But here’s the thing. He’s a great example of this whole idea that I’m talking about. Like, no ex-Googler … Whatever your stereotype image in your head is of what a tech person looks like … Let’s just say-

Ed Pizza: I’m a Racker.

Paul Singh: Yeah. A Rackspace guy. I don’t know. Like, no tech person is going to magically leave a tech company and then go into, let’s say, accounting and figure out how to make the software to make those accounting businesses run. By the way, if you don’t believe me, just look around you. Go to whatever your favorite bar or restaurant is and look at the point of sale. It’s awful. It’s made by some dev that thought that he or she could somehow magically replace the point of sale. And yeah, maybe they’re being successful, maybe they’re making some money, but honestly, ask the staff how that really works. Like, yeah, you can make some money in the short term. Don’t get me wrong. I’m sure like the Breadcrumbs and the Toasts of the world are making a lot of money. But the reality is, the true money, the true innovation, the true success of every industry is going to come from the inside.

And back to David, that’s why I bet on him. That’s why we bet on him. And it’s because he came from the inside. He was an accountant at an accounting firm. And David, if you’re listening, I’m probably not doing you any justice here. But he was an accountant at an accounting firm. He saw a problem of his firm not being able to accurately stay organized around multiple clients and the billing requirements and the measuring, tracking time, that sort of thing. And so he chose to learn how to code. And he chose to pre-sell. I think when we met him, I think he had pre-sold like three or five accounting firms before he ever built that first version. And I don’t think he gets a lot enough credit for that. I think that a lot of other people, and hopefully they’re listening to this, like, let me just say very bluntly that I think over the next 10 years, the biggest money to be made is from the inside of whatever industry you’re in.

So like the holy grail, for example, would be just like what Jetpack did, just like what David did as an accountant, he learned the software, and as an insider in the accounting world, he knew the ins, the outs, the ugly parts, and he built the software natively for accounting firms. Like, nobody on the outside could do that. So whether you’re a bartender or, I don’t know, a lawyer or whatever, it’s more important than ever, if you really want to build something big, a business, whatever it is, to understand that the power really does belong to you. Like, I think anybody can learn to code. I don’t think everybody can learn the native inner workings of whatever industry you want to disrupt. So …

Ed Pizza: Well, we talk about it. A lot of the best companies out there are solving a problem they had, and it’s overcoming that. You talk about the devs and the ability for the devs to come over. Like, nothing against coders. I’m not a coder, but I also know how to fix problems in industries that I have deep knowledge in, and somebody sitting in a room programming isn’t necessarily going to have that context of having banged their shins against that specific thing a million times. Yeah. Actually, quick story. You remember … Have I ever told you that we built a point of sale system back like 15 years ago?

Paul Singh: That sounds like a bad idea.

Ed Pizza: It was. It was a horrible idea. But the very short version of, like, not having a great relationship between the problem solver and the dev was, I remember mapping out the system for the lead dev on the system. And I had mapped out on a window that was in the office of where all the printers needed to go. So the hot side for this restaurant needed to only get the hot side stuff, because they didn’t need to see the cold side stuff. And so like, here’s how we’re going to map everything, and here the dip switches we need and the software and all that stuff.

And we get to day zero, we’re installing the system, and everything is printing at every printer in the restaurant, including all the receipt printers in the front of the house. I’m like, “Hey, I don’t understand. Like, where are my dip switches?” And the dev’s like, “Well,” he’s like, “I just didn’t see the big deal about it just printing everywhere. Like, they can just throw out the slips they don’t need.” And it was like, “Oh my God. Do you remember the window and the development path?” And he’s like, “Well, yeah, but it just didn’t make sense to me,” because he’d never worked a restaurant.

Paul Singh: Yeah. By the way, if this idea is resonating with anybody, then I’ll just throw one other little tip out there. The key is to bring tech into those industries without ever mentioning the word tech. Because I think that that word is a little overloaded. And for us, for the people inside the industry, the people that, like us, that probably already know how to use all these tools, tech to us implicitly probably means unbounded possibility. But it’s important to understand that for people that don’t know this, tech could be scary. I mean, I remember distinctly, one of my most random memories of the Tech Tour was I was traveling, I forget, from one city to another and I pulled into a gas station. And the RV, the Airstream, had the Tech Tour logo on the side and stuff like that. And this guy, he must have been in his late forties, maybe early fifties, he walked over.

Long story short, we had this real short conversation. He asked what I was doing. I told him. And he said … And I never saw the guy again, but he said, “The thing is with you tech people, you tech people come to us.” This was in the middle of the country. I want to say it was like Western Indiana or something like that. He says, “The problem with you tech people is you come into all of our industries talking about all this opportunity you’re going to bring us, and then, surprise, surprise, we’re the ones that lose our jobs to whatever software machine you built.” And I thought that was a really interesting point I’d never thought about. Now, by the way, I’m not saying that maybe that wasn’t inevitable, by the way, whatever happened to him. But I do think that there’s a lot of … The more and more I think about that years later, it’s just an interesting thing to think about.

Ed Pizza: Look, I mean, I don’t want to bore people with a super long episode right out the bat, so I want to make sure that we’re back to Paul’s favorite word, tactical. But I don’t think we can close the show without hitting the one topic that you want to start the show with. Well, not start, but you want to make sure we have, that came in this morning from Caleb. This is like vintage Paul. What’s the difference between playing not to lose versus playing to win?

Paul Singh: Yeah. So for context there, I tweeted earlier this week about this idea. I said, I don’t know who needs to hear this, but playing not to lose is different than playing to win. And it sparked a lot of interesting replies and DMs and that sort of thing. But anyway, Caleb … Again, this will all be in the show notes. But Caleb tweeted back and he said, “Hey, high level, that makes sense. But how do you bring it down to something practical?” And he said more specifically, he said, “What’s a move you made recently that was playing to win where you could have played not to lose?”

There’s a lot of ways I can take this, but to your point, Ed, I don’t want to like drag this episode out forever. I’m going to give you something that’s top of mind for me, and I’m going to use that as a illustrative example. And so for anybody that’s in sort of DTC/e-commerce right now, maybe this will resonate with you. Here we are in September of 2021. And for those of you, again, that are in adjacent industries, what you know is that a couple months ago, back in May, Apple released iOS 14.5. And in brass tacks, basic terms, the privacy changes that rolled out with that effectively decimated a paid acquisition channel for a lot of companies. And I won’t go into the details. I don’t want to bore anybody. But the bottom line is is that you cannot target your client or your prospects as tightly as you used to be able to.

Ed Pizza: Yeah.

Paul Singh: And so, what happened? Well, you don’t have to go far on Google right now or jump into any entrepreneur’s Slack group or email list, or, I mean, Facebook groups. You don’t have to go far to see what’s happening. What’s happening is every e-commerce company right now is trying to figure out what tactics, how to change their paid ads, to like get their cost of acquisition back to what it was. That’s playing not to lose. Because this is a foundational shift and it’s only going to get worse. We already know Google’s going to do the same thing. Hell, we know that iOS 15’s coming, and we know that we lose open data.

So back to Caleb’s question, what is playing not to lose? In this example that I’m giving you, playing not to lose is somehow having this illusion that pressing your buttons in some magical way is going to take back to pre-iOS 14.5. That is delusional. Playing to win is realizing that in certain scenarios like this, tactics will not solve the problem. You have to start thinking more broadly. So I’ll give you an example again, using this same illustrative example. I think one of the most fascinating things that has been done by anyone in the space has been HubSpot. They’re a B2B software-as-a-service thing. But more importantly, if you’re listening to this, Google the HubSpot Podcast Network and go look at that, like at a high level. By the way, if somebody at HubSpot is willing to talk to me about the economics of that, please do. I’ll keep it private. I actually tweeted about this yesterday. I want to do this in the women’s health space, too.

But anyway, what they did was, in my opinion … from the outside again, I have no proof, but I think they took a bold bet. They were like, “Hey, we know the landscape’s going to change. We know that it’s going to be profound. And honestly, we know that everybody’s probably going to try to scramble to try to find the magic sequence of buttons to go back in time.” So they decided not to fight that fight. Again, I’m looking at it from the outside. Maybe I’m totally wrong. Again, if you’re at a HubSpot and I’m wrong, come talk to me. I want to learn. What did they do? They, instead of wasting their time like everybody else, trying to find this magical solution, they decided to take a bold bet. And they said, “You know what? Let’s buy the most interesting business podcasters, like business topic focused podcast, and let’s just buy them. Let’s buy the Hustle. Let’s buy the other … And let’s create our own podcast network.”

Those podcasters can no longer sell ads to anybody. And that’s great because for those podcasters, they don’t have to worry and chase down fickle advertisers every 30 days or whatever they’re going to do. But instead, what does HubSpot do? If you listen to any of their podcasts right now, they’re not even advertising HubSpot. They basically say, “Hey-

Paul Singh: … their podcast right now, they’re not even advertising HubSpot. They basically say, “Hey, welcome to this episode. We’re part of the HubSpot Media Network…” and that’s it. I love that. I love that. That’s amazing. That, by the way, is the inspiration of where I think the future’s going. But anyway, back to Caleb’s question, we’ll talk about that in another episode I think, back to his question, I think the important thing to understand is that playing not to lose is about accidentally or maybe even implicitly having this mental model in your head of, “Oh God, something’s changing. What do I got to do to keep that thing the same?” And probably in the moment it feels like the right thing to do because your lizard brain sees something change and you’re like, “God, I’ve got to make that not happen anymore. What do I do?”

But experience is about looking at that same problem and saying, “Okay, is this a short term thing? Because if it is a short term problem, then, yes, tactics can probably fix it.” But if it’s not a short term thing, then you have to fight that inner lizard brain and say to yourself, “Okay, playing not to lose here is not going to get us out of this trouble. We need to play to win. And what does that look like? Help.” DM me. Maybe we’ll do like a breakdown of somebody’s business if they ever want to do it. But hopefully that example is illustrative. But keep me honest here, Ed.

Ed Pizza: Man, I could have made a lot of money posting a lineup for people to say, “What are the chances that Paul talks about lizard brains on the first episode of the Results Junkies Podcast?” That would’ve been a sick line in Vegas. No, I think to boil it down for me, as you said, I think it comes back to when companies are trying to maintain the status quo. When change happens, to use something that you talk about, that’s a point for the best companies to run in the other direction. There’s a moment there where you can say, “We’re going to try and hop on the hamster wheel like everybody else and catch back up,” or, “We’re just going to go completely different direction. We’re going to go define a new medium.”

And sometimes there’s going to be epic failures, but my guess would be if we were able to chart the history of all the companies that you and I have come across, that there are probably a remarkable number of successes where when there was a huge inflection point and somebody decided that was when they were taking the left hand turn that there was some real massive companies built.

Paul Singh: Agreed, and just to keep it punchy I’ll just share my framework. So the inevitable question somebody’s going to have here is, “Okay, that’s one illustrative example, but what is the framework I should use?” So I’ll just give you one that’s top of mind for me. I want to double my company’s top line revenue every year. That’s it. That sounds really simple, but it is not easy to do. But it’s so clarifying, when you’re in the moment and you’re thinking about whatever problem you’re dealing with, I can apply that framework. Are we talking about something here that’s going to double my money next year or double my revenue? If no, this is not a problem. Tactics might figure it out, whatever. But on the other hand, there are certain things that when you apply that framework then become obvious where it’s like, “Man, even if I solved that problem, I’m not going to get to 2X.”

And so, for whatever it’s worth, that’s the framework that I use, I want to double my revenue. And to your point, sometimes it works, sometimes it doesn’t, but that’s not the point. The point is to be, in a world where you can’t predict the future, the goal here really ought to be to reduce the number of bad decisions you might make. And so playing to win to me is about, when you’re just starting out, it’s not about anything other than getting to 1,000 bucks of revenue or whatever in the first month. That’s something I think about a lot. And then I think it’s about setting the target at a million bucks by the end of the year. Not because you should be feeling bad if you don’t, but because the framework of thinking that you would apply then to your daily decisions of, is this going to get me to a million? It’s going to make it a lot easier to say no to a lot of things.

And now fast forward to we’re at 40 mil now and I now know that when I want to go to 80 next year, I know that that’s going to allow me to say no to a lot of things. Because I always get these pundits that are like, “Oh, Paul, you should think about this button. It should move. The pixels need to move this way.” I’m like, “You might be right, and maybe I’ll go get somebody to test that on Google Optimize.” But even if it’s successful, probably not going to make me another 40 mil. So anyway, play to win. Play to win. And I think this is true of your careers too, by the way. Your careers, whether you’re sitting at a cubicle, everybody has this idea that entrepreneurship is about starting a business. That’s not true. I think entrepreneurship is a way you think, and so playing the win is also something I think you should be using in your career.

There’s the table stakes of what you have to do that’s expected of whatever role you’re in but then there are the things that you could do that could 10X your career in as little as a quarter or a year. And that’s playing to win, picking which bigger projects to work on, that sort of thing. So anyway, I could belabor the point, but hopefully, Caleb, this is useful to you. At some point, we’ll probably do real business breakdowns, and if you ever are interested in doing that, again, Let’s figure out how to give, use some value but also maybe use that help or those results that you get to help other people that might be listening.

Ed Pizza: All right. So we set out with an ambitious goal in episode number one to cover eight topics. We got through three, which is probably a little bit less than what I thought we were going to cover. But I think the goal that we set out to achieve at the start of episode one was achieved, which was, in Paul’s words, to not be hand wavy, but just to try and get to the root of what someone was asking and also to be okay being wrong. And I think you’ve got to be out there right from day one, whatever is you’re doing, and it’s something that Paul just said, entrepreneurship isn’t necessarily about starting a business. It’s about where your head is focused and what sorts of questions you’re asking and how you can be transformational, not incremental. And so our goal is, fortunately or unfortunately, to be incrementally better in episode number two. Right, Paul.

Paul Singh: We’ve set the bar low, I suppose, so yes. That’s going to be easy to do.

Ed Pizza: We have. We can step over the bar, but I don’t know that we’re going to be transformational in episode number two. But we’re going to be better than we were in episode one.

Paul Singh: That’s right. That’s right. Yeah, so we set out to hit eight topics. We hit three. Hey, not bad for episode one. I’ll take that.

Ed Pizza: Yeah.

Paul Singh: Maybe I will not bring eight topics to the table next time. But now at least we know what we’re talking about in episode two and we won’t drop any hints here though.

Ed Pizza: Yeah, we got five, but I guarantee you, by the time we get ready to record episode two, we’re going to have at least five more that we’re like, “God, now I don’t know which ones we want to go with.” But, like Paul said a couple of times during the episode, is a great way to feed us content for the next show. But you can also just hit the tweet button. You can tweet @PaulSingh for Mr. Paul, and you can tweet @PizzaInMotion for me. And as we get rolling here, you’ll find a couple other ways to get ahold of us. We’ll roll out some other cool stuff that you guys can use to find us where we are. But the goal is, if you’re thinking about picking something up today and you want to move forward, don’t leave it till tomorrow. Right, Paul?

Paul Singh: Just get started.

Ed Pizza: Right.

Paul Singh: I mean, the idea ultimately is, I want you to be able to take something you learned here and apply it right after this. But if you take nothing away from us, whether you’re listening to episode 200 or episode one, is just do it. There’s no glory in thinking about something. Just try it out. Either kill the idea within a day or two or get enough traction to justify investing the next week or two. But that’s the thing that you’re going to take away every time you listen to one of these things.

Ed Pizza: All right, we’ll see you guys again next week.

Trailer: The Results Junkies Podcast

I suppose the world doesn’t need another podcast… but here we are. 🤷🏻‍♂️

I’ve spent the better part of the last twenty (20!) years starting, building and growing companies — from both sides of the table. Most failed, some did just ok and a few became unicorns.

The truth is that I don’t quite know what the show will become but that’s the way these things go.

I didn’t know how to start a company, so I just started.

I didn’t know how to start investing in startups, so I just started.

I didn’t know how to live in an RV (and meet most of you!), so I just started.

I didn’t know how to start a podcast, so I’m starting.

If you’re looking for more episodes: The Results Junkies Podcast

2020, man.

I guess that’s what we’re supposed to say. Amirite?

Despite the broader uncertainty, 2020 has been pretty good around our household: We spent more time together, as a family. We did more things, as a family. We’ve made great memories, as a family.

I’ve learned that my kids are even more creative (and funny) than I realized.

I’ve learned that Dana makes everything look easy. (It isn’t, of course.)

I’ve learned that my neighbors are pretty great.

I suppose the truth is that the lockdown forced me to realize just how good I have it right here at home.


I’ll turn 40 in 2021.

The thing about milestone birthdays is that they force introspection.

Am I proud of what I’ve done? Am I doing what I love to do? Am I a good person?

I suppose I have ~90 days to figure it out. Which, coincidentally, is just about the same time you have to figure out what you’ll get me for my birthday. 👀

I spent my 20’s acquiring things. I spent my 30’s acquiring experiences. And, with some luck, I hope to spend my 40’s making memories… with my family.

I’m not quite sure what that looks like just yet but, for a start, I think it means setting aside a week every quarter to do something fun with the family. Maybe it’s a staycation. Maybe it’s a bigger trip. Maybe it’s a full week. Or maybe it’s taking every other Friday off.

The point is that making memories requires active participation.


I realize I should probably say something about my professional life… but I’ll save that for another day. For now, I’ll just say that it’s going really well. And that I’m thankful to be doing work that feels like play.

More often than not, I find my thoughts wandering back to this: Eva’s turning seven next month. Henry’s almost two. Baby #3 will be here in less than sixty days.

Am I a good husband? Am I a good father? Am I doing enough?

I sure hope so. I guess we’ll see.

2020 has been a unexpectedly wonderful year for us. I can’t wait to see what 2021 brings… 👋🏻

You (probably) don’t need a MVP. You need a list.

Over the past few years, it’s become fashionable to recommend that startups build a Minimum Viable Product (MVP) in order to reduce risk and “be” a Lean Startup.

Every mentor says it. Every accelerator teaches it. Every book recommends it.

So now we’ve ended up with an incredible number of “tech” startups that think predictable sales machines can just be bolted on at any time.

But consider this: some of the most successful companies originally started as email lists before any code was ever written. See AngelList, Product Hunt and Mint as just a few examples.

What if we encouraged more startups to see themselves as media companies that might make a product in the future?

What if we encouraged more startups to see themselves as email marketing companies that happen to have a product?

Whether you’re a founder, investor or community leader, my guess is that you’re interested in creating more sustainable (and, hopefully, valuable) businesses.

If that’s true, then a startup’s ability to acquire attention is just as important — if not more important — than their ability to build a product.

There are only 2 stages to any company

I’m not sure why people — both investors and entrepreneurs — make things so complicated.

There are only two stages to any company:

  1. Will it work?
  2. How big could it be?

Once you have at least one person that you don’t know paying you at least $1 for your product, you’ve passed the first stage. Congratulations, you’re not a startup anymore — you’re a business.

The second stage is where investors and entrepreneurs should focus their conversations:

  • If there are ~1,000 potential customers, you’ve got a great business… but it’s probably not big enough for investors.
  • If there are ~10,000 potential customers, things are starting to get interesting for you and the angel community.
  • If there are >100,000 potential customers, you’re on to something that will probably excite venture capital firms.

Pro tip: if you find yourself — both investors and entrepreneurs — spending more than 50% of any given meeting talking about the product, something’s wrong. In VC, we make our money via the growth of the business — not the product itself.

Don’t let your mentors confuse you, business isn’t all that complicated: sell one thing to one person you don’t know, then repeat. Ideally, get faster at it along the way.



How to know when you’re ready to start a business

First time entrepreneurs often think that they need investors to get started. The truth is that you need customers (and that most successful companies don’t need to ever raise money).

If you can’t sell a product, pre-sell a prototype.

If you can’t pre-sell a prototype, start an email list.

If you can’t start an email list, go wherever your customers might be.

If you can’t go to wherever your customers might be, it might be time to admit that you don’t really want to start a business. 🤷🏻‍♂️