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. 🤷🏻‍♂️

You don’t need a Board of Advisors

If you sit through enough pitches, you’ll quickly notice that the majority of them will have advisors listed somewhere on their team slide. (Or worse, they’ll have so many advisors that it has to be separated out to a separate slide entirely.)

It’s 2018, y’all. You don’t need advisors. You need customers.

It's 2018, y'all. You don't need advisors. You need customers. Share on X

If you’re serious about meeting with someone about your company monthly, put them on your actual Board of Directors. Otherwise, giving equity away to someone that you’ll barely speak with on a regular basis is a bad reflection on you and, worse, a waste of your company’s equity.

Can I park my Airstream in your tech community? (I’m serious.)

We visited 94 startup communities across the US and Canada over the past few years. Ninety four. 

It all started with an email that I fired off to this list in 2015 without much thought. I hadn’t even bought the Airstream yet.

And, before I knew it, we spent the next two years driving over 100,000 miles and meeting over 50,000 people at our events across the country. People even started making short videos of our visits.

The whole thing was surreal… but fun. And interesting. And exciting. And amazing. And that’s why we’re doing it again in 2018.

The ask is pretty simple: fill out this form and let’s hop on a call to brainstorm our visit. We’ll bring a couple of other investors and entrepreneurs to your tech community. And we’ll create 3-4 days of office hours, workshops and keynotes too. And, in the process, we’ll all have fun while we work towards helping your entrepreneurial community get to the next level.

How to gauge the state of your local tech community

I sign up for a ton of email newsletters.

Part of it is because I want to try keeping up with what’s happening in all the communities we’ve visited over the past few years.

Part of it is because I want to see what other copywriters and authors are sending out to their audiences.

Part of it is because I want to feed my extreme FOMO for information.

Anyway, that’s not the point…

The funny thing about the end of every year is that every single local tech newsletter ends the calendar year with a retrospective look at their local entrepreneurial community. And they usually sort it by the number of clicks (in an attempt to “prove” what the readers cared about over the past twelve months).

Maybe it’s because they think it matters. Maybe it’s because they don’t have anything else to write about over the holidays. Maybe it’s because they’re desperately trying to boost their clicks before the end of the year.

Here’s the thing: the state of your local tech community isn’t measured by web traffic reports.

You measure the state of your local entrepreneurial community by the number of companies created. By the jobs created. By the revenue growth created. You measure the state of your local entrepreneurial community by a different measuring stick.

It’s not about people’s clicks. It’s about people’s actual work.


Sales emails: two changes that get 250% conversions

It’s super simple:

  1. Keep it short, especially the first time you email someone. No one enjoys walls of text. Ever.
  2. Always make the benefits clear within the first two sentences. This applies to the first email you send someone — and the hundredth email you send that same person. Don’t introduce yourself. Don’t waste a paragraph re-explaining that thing you talked about on the phone. Just get to the benefits. If it benefits the reader, they’ll respond.

Emailing an investor? Start with your traction. (“We have X customers and we’re growing Y% week over week.”)

Emailing a prospect? Start with the quantifiable benefits. (“We helped [XXX] get a 88% increase in leads when they used us.”)

If you find yourself sending your investors and your prospects (and even your friends) emails “bumping” something back to the top of the inbox, it’s your fault for not winning their attention. Rewrite the subject line, email and call to action instead of sending more awful emails.

That’s it. Really simple. No brainpower required.

Why Startups Die

When we first moved into the Airstream, we thought that safety and logistics would be incredibly hard to handle but that decent wifi and entertainment would be super easy.

After 100,000 miles under our belt, it seems that we had it backwards: the things we thought would be hard turned out to be easy and the things we thought would be easy turned out to be hard.

(Safety and logistics in a RV is much easier today thanks to smartphones and other travel blogs. Streaming Netflix to your Apple TV, however, via your mobile hotspot can blow through your monthly data in hours. 🤦🏻‍♂️)

I think it’s the same with startups: many start out thinking that building the product will be hard and selling the product will be easy. In hindsight, most tell me that they had it backwards.

Most startups die because of their inability to acquire customers not because they couldn’t build the product. (Most people don’t travel because of the excuses they tell themselves not because someone else was holding them back.)

Most startups die because of their inability to acquire customers not because they couldn't build the product. Share on X

I started my travels to escape life. Along the way, I found it.

The first question people ask you about anything tells you almost everything you need to know about their mindset. This applies to entrepreneurship, personal development and even living in a RV.

For example, the #1 question I get about living in an Airstream is this: “But, how do you back it up?”

Not, “where can I go with that?”

Not, “where do I learn more?”

Not, “where do I go from here?”

Here’s the point: most people focus on all the reasons they can’t do something rather than consider all the ways they could do something.

They let their fears stop them. They let their internal “invisible scripts” stop them. They let what other people think stop them.

If you’re honest with yourself, you have probably experienced this for yourself. I know I have.

If you decide to stop reading now, I’ll leave you with this: in 2018, I hope you resolve to think about the future more than you think about the past. I hope you resolve to think more about what could go right than what what could go wrong.

Last year, I wrote about my 26,141 miles of mistakes, learning and growth. This is about the next 30,000 miles of mistakes, learning and growth through 2017.

For some context: I’ve driven nearly 100,000 miles in the past two years — back and forth across North America more times than I can count. A little over half of those miles involved hauling my 2016 30′ Airstream Classic behind me. And almost all of those miles included my soon-to-be bride.

I’ve lived in 94 cities for a week at a time. I’ve slept in 44 states and two provinces. I’ve met over 50,000 people along the way. (And even invested in some of the best of them.)

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So, here are some of the most personal things I learned in 2017:

  • Lying to yourself is the worst thing you can do. When things don’t go right, most people blame other people or their own circumstances. I know I did. But those are just lies we tell ourselves to dull our own disappointment, guilt or shame. I don’t care if you lie to other people (though, I hope you don’t) but please don’t lie to yourself.
  • The rear view mirror is useless. (Warning: bad dad analogy ahead… brace yourself.) When you pull a travel trailer behind you, the first thing you notice is that the rear view mirror becomes useless. You can’t see anything behind you and it forces you to just focus on what’s ahead. That’s not a bad way to think about your life as you head into 2018.
  • Negative people are the worst — cut them out. You don’t need to confront them. You don’t need to have awkward conversations with them. You don’t even need to delete them from your phone. Just optimize for hanging around the most optimistic people you can find. You have the same 24 hours in each day as I do — spend them with happy people.
  • Make a commitment to travel more regularly. You don’t need your own Airstream or a lots of time off from work. If you can save $250 per month, you can spend a weekend each month visiting some other city within a 500 mile radius of your home. Do it. It’ll be the best investment you make in yourself.

As 2017 comes to an end, there’s one thought that continues to hit me: Two years ago, I started my travels to escape life. Along the way, I found it. 🙏🏼

So, here’s my advice to you: Make 2018 your year. Spend more time looking forward and less time looking back. It’ll be worth it, I promise.

Make 2018 your year. Spend more time looking forward and less time looking back. It'll be worth it, I promise. Share on X