Want to get inside the head of an active investor?

  • What are common mistakes that founders make when they pitch an investor?
  • Do you ever get used to saying “no” to founders?
  • Why is your beard so epic?
  • What questions should I ask investors to build trust, uncover hidden problems, overcome objections and speak to desires?
  • What’s Dave like in real life?
  • What is the most effective way to follow up with investors that are slow to decide (or have previously said no)?
Instead of keeping these conversations behind closed doors, I’m going to give each of you full access by starting an “Ask the VC” series here. What do you want to know? 
Ask a compelling question, and you just may see it answered right here, by me. And it won’t cost you one penny. Or any equity.
Go ahead and ask anything you like, I’m going to give you direct answers and ready to use, field tested tactics.

Observations on India

I’ve spent a decent amount of time in India over the past few months. Most recently, I spent a little over two weeks of August meeting with founders and investors in Mumbai, Delhi, Bangalore and Goa. A couple of observations in no particular order:

  • Indian founders don’t have clear role models… at least not within the Indian startup ecosystem. That being said, that will likely change over the next 3-5 years as the founders of companies such as SnapDeal, FlipKart, Naukri, MakeMyTrip, Inmobi, Directi (along with many other fantastic companies) continue to grow.
  • The communication style of Indian founders is quite different than other places. It seems like a cultural thing: founders (and perhaps most people) seem to think that they are establishing authority by giving longer answers to specific questions. I’d like to see founders improve their communication styles: be direct, be crisp and be passionate. By doing that, they’ll be able to better communicate with cofounders, potential team hires, press and investors (both foreign and domestic). More tips here:Your Solution Is Not My Problem. (On a side note: There’s huge opportunity for a speaking coach to make a metric shit-ton of money in India.)
  • Pound for pound, the Indian technical founder has far more raw horsepower than I’ve seen anywhere else. I suppose that’s why nearly every pitch I’ve heard from Indian founders has been heavy on the technology powering the solution. Unless you’re building a startup that *is* technology, your pitchshouldn’t contain any mention of the technology you’re using.
  • I’d like to see more Indian founders try to solve problems for the Indian market. Until now, it seems that most focused on building online products that could be sold to the West and that made sense: the Western internet user was way more likely to buy online. Internet penetration is rapidly increasing in India, that’s no surprise — Indian founders should start to focus on the Indian internet user because more of them are coming online daily, their comfort with purchasing on the web is growing and, frankly, because outsiders are less likely to understand the cultural nuances of the Indian customer.
  • No surprise: most of the Indian investor community isn’t founder friendly. They can be very slow, deal terms can be onerous and the overall experience for founders is rough. For investors, there’s a lot of opportunity in this — just be more founder friendly and I suspect your dealflow will rise considerably.
  • Investors seem to inherently distrust founders. Investors should only take referrals from trusted sources and initial check sizes should be smaller while the relationship is still new. Founders should take it upon themselves to present themselves in the most truthful way. Regardless, I think you’ll begin to see investors prosecuting founders publicly in an effort to make a statement to the market.
  • As a first generation Indian-American, I find it interesting that many founders and investors born and raised in India seem to be more pessimistic about India’s prospects than I (and, by extension, other outsiders) am. As Sasha Mirchandani has said in the past, my hope for India is that it changes from a pessimistic society to an optimistic one.

I’m certainly not the first one to say this but, even with all the challenges that exist, India has no where to go but up — the question isn’t *if* but *when* it will happen. We’ve made a handful of investments in Indian startups over the past year and we’re planning to aggressively ramp that up immediately. Watch out India, the 500 train’s coming!

The goal is to make good decisions, not to make money

Google Ventures’ Joe Kraus recently wrote about unconventional investing rules and this particular portion caught my eye:

This rule came from a three-day poker camp I went to seven years ago. One of the pros got up to the front of the room and asked the question, “What’s the goal of poker?” Of course, someone put their hand up and fell into the trap. “To make money” they said.  Wrong. “The goal is to make good decisions, not to make money,” countered the instructor. If you make good decisions — better, more consistent decisions than the other guy — then you will end up making money.

In poker, if you approach the game to make money as opposed to making good decisions, you can fall prey to things like going on ’tilt’ after a bad beat, feeling ‘lucky’, continuing to fire bluffs at an opponent who’s clearly shown you he’s willing to call you all the way down, or playing in games that you can’t afford. When you hunger only to make money *now*, then you end up making bad, mostly emotional, decisions.

It seems to me that many people tend to “armchair quarterback” other investors’ thesis. (After all, if it seems crazy, it must be crazy – right?) Unfortunately, there’s no crystal ball when you’re dealing with early stage internet startups.

Here’s the analogy I like to use: if you’re going to walk into a casino, you already know that the odds are in favor of the house. Always. So, you’ve got two choices on how to approach the games:

  1. The first option is to wander around the gaming floor while you try to “feel” a good table. In the process, you’ll likely spread a few bets around while you try to get a sense for the momentum on the table. If you win, you’ll pat yourself on the back. If you lose, you’ll likely move on to the next table. If you’re investing for fun, altruism or any other non-monetary reason, this approach is probably OK as long as you recognize what you’re doing.
  2. The second option is to have a plan before you enter the gaming floor. Pick a thesis (eg, a game and a plan: “I’m playing blackjack, hitting on any 17 or lower.”) and play the hell out of that thesis until you’ve either uncovered new information that suggests you should change the thesis or you win.

To put it more bluntly, would you rather try your luck at the roulette wheel or do you try counting cards on the blackjack table? If you’re an angel, you’ve got the option to choose either path. If you’re a VC (eg, investing other people’s money), I believe the second option is the only option.

Fund The Founder Or The Prototype, But Not The Idea

When you invest in a company, you’re choosing to back the founder, the idea or the prototype. Or some combination of those. It seems to me that the only reasonable choices are to back the founder or the prototype, but not the idea.Either back the founding team and be very clear about it (eg, like YC funding founders without ideas) or back a prototype with some sort of small but meaningful traction. Anything between those two extremes is unnecessarily adding risk to what is, by definition, already very risky.

On being an API to Venture Capital and Functional Expertise

I’ve been thinking about this idea for a while: that it’s *everyone’s* job to be an API to venture capital and functional expertise. (Though, I owe a big hat tip to Fred Destin for being the first to publicly use the “API” term to describe 500.)If you’re a startup founder, your sole job is to build a fantastic business. Rather than spend time organizing the next local startup grind or some such nonsense, spend your time and energy on making something people want (and, ideally, want to pay you for). When you do this, other founders come to you when they need advice and intros to venture capital and functional expertise.

If you’re an investor, your job is to write checks *and* add value. Here’s the paradox of investing in early stage companies today: we all know that the venture capital industry is a hits-driven business but thebest companies/founders don’t need your money. Thanks to platforms like AngelList, early stage money is becoming a commodity — investors need to be differentiated. Keep your deal terms simple, move fast and answer the phone when they call.

If you’re on the government or policy side of things, your job is to make it easy for investors and founders to work in your region. You could help investors via financial incentives (see NRF, Startups Chile, etc) but the fact is that early stage money follows founders now. It’s becoming easier for founders to raise their first round of money without having to move to Silicon Valley full time but, especially as the company grows and thinks about later stage money, founders are likely to follow the money (read: they’llmove closer to the VCs). If you want to kickstart the entrepreneurial vibe in your region, start by making it appealing for founders to locate their companies there. If you do it right, they’ll want to stay where they are for the long term.

Again, it’s our collective responsibility to be a bridge to venture capital and functional expertise — as private citizens and as a country. The United States is where the internet started and, when you think about economic development and job creation, it’s where some of the most successful internet companies have flourished over the past few decades. However, the internet landscape is changing: more people are online than ever before, technology costs have dropped to an all-time low, and early stage capital is becoming a commodity.

As the internet becomes more accessible across the planet, we’re seeing that early stage internet startups can operate from anywhere: as the web gets bigger, the world gets smaller. From an immigration standpoint, it’s incredibly important that we encourage the best startup founders around the world to start their businesses here in the US — after all, they’re less likely to move here once they’ve planted their roots elsewhere and business starts booming.

Regrets And An Apology

There are few things in life that you can do to potentially change the world and 500 Startups is one of them. Though, this kind of opportunity comes with it’s own burdens: we’re a relatively small team that bootstrapped it’s way to 350+ investments in nearly 20 countries now. On any given day, we’re collectively fielding hundreds of emails from existing portfolio companies and hopeful entrepreneurs.

“I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.”

–Maya Angelou

My time here has been so rewarding and I’d do it again if given the opportunity. But, I regret that I haven’t figured out a way to stay on top of things in both my personal and professional life: I’ve lost touch with old friends, thrown wrenches into my personal relationships and left more than a few current/future founders hanging while they wait for me to catch up on email and phone calls.

So, consider this my public apology to anyone that’s felt unimportant because of my actions (or lack thereof) — that’s not the case at all. I’m doing the best I can and, one day, I hope to make it up to all of you for being so incredibly patient with me.

On Intellectual Curiosity

I used to carpool to elementary school with a classmate that lived nearby. I remember only one thing from all those years: her dad would tell me anything I wanted to know as long as I asked a question. (Mr. Clayton, where are you these days anyways?)I went to a small private school and was generally OK with being “the nerd” around my neighborhood. I’m a terribly slow learner when it comes to traditional classroom instruction, but I’m a sponge when someone answers a question of mine — more importantly, I love learning stuff on my own. I like scratching my own itch. It’s probably not the most efficient way to learn something new, but it’s worked pretty well for me.

I’ve met a lot of people over the past few months and I’m starting to realize something: you can’t teach intellectual curiosity. You might be able to inspire or briefly encourage it, but you can’t force people to be genuinely interested in learning new things.

Winners Take Most

The top three links on the first page of most Google searches take ~60% of the overall clicks. (A quick search will show you a number of studies with more research.) I’d bet that these numbers probably hold true for internet startups as well.If you’re building an internet company today, you’re not competing against the other team trying to build the same thing — you’re actually competing with all the noise out there.

Target a niche, launch the MVP early, iterate often and find product market fit as fast as humanly possible. After that, focus on distribution — traction is defensible and, more importantly, you need to be within the top three products within your niche.

The winners take most of the market, everyone else gets the scraps.

Thoughts on the JOBS Act (or, Coming Soon: More Liquidity In The Private Markets)

The JOBS Act is a hefty bill with a number of key points but, for the purposes of early stage tech startups, there are two material items that will drive the increased liquidity of the private markets:

  1. **The JOBS Act legalizes crowdfunding. **This means that the average person will now be able to invest up to 10% of their yearly income or $10,000 (whichever is less) in exchange for an equity stake. Startups can raise up to $1M per year (or $2M per year if they release audited financials) — this is more than enough for most internet startups today. Overall, this gives early stage startups access to more potential funding sources (but will likely cause the market to become crowded with startups that might not ordinarily pass the bar for experienced angels and VCs).
  2. **The JOBS Act raises the cap on private shareholders from 500 to 2,000. **In the past, fast growing tech companies sometimes found themselves up against the 500 private shareholder limit which put them in the position of going to the public markets early instead of dealing with the  (expensive and time consuming) alternatives. This gives the founders breathing room they might need to mature the company a bit further, if they want it.

By lifting the cap on the private shareholder limit, we’ll certainly see private secondary markets (such as SecondMarket) benefit. The less obvious part is that crowdfunders and “superangel” funds (such as 500 Startups) may benefit as well.

Consider the scenario where a company has raised $100K from crowdfunders roughly six months ago and now approaches an early-stage VC. In this new round, it may make sense for some of the crowdfunders to sell their positions to the new VC (or other investors) in the new round — particularly if the crowdfunders don’t plan to make follow-on investments and/or want liquidity a little earlier. The crowdfunder gets to make some upside on their money, the new investor can take a slightly larger stake and the founder doesn’t have to dilute any more than necessary for the new round.

Now let’s suppose that a few years have passed and the company wants to raise an even larger round (for the sake of this example, let’s assume the company’s doing OK and the prospects look good). The existing investors (again, crowdfunders and some early stage VCs) may be open to selling some portion of their positions to the new investors, presumably later-stage VCs that may also have a newer fund (read: they can afford to wait longer for the company’s exit. The reason for this is a separate and longer conversation but, in the case of venture funds, there’s sometimes a risk/reward calculation that might justify selling assets sooner rather than later. Read up on IRR to learn a little more.).

Summary: the JOBS Act will increase the liquidity of the private markets. And this probably is a good thing.

Rocking Out Your AngelList Profile

  • Start with a little bit of research. AngelList makes it so easy to browse through the different tags that can be associated with your profile. If you’ve picked a tag that doesn’t have a lot of investors following it, ask yourself whether it’s better to pick a slightly broader tag instead. You should also be looking at the startups that seem to be getting the most followers/activity within those tags. Check out their profiles and identify why the startup is particularly appealing – it’ll make the next few bullet points easier for you to knock out as well.
  • You should always be updating your AngelList profile, not just when you’re fundraising. If you’re not fundraising now, you’re trying to get investors to follow your startup. If you *are* raising money, you’re trying to get investors to request an intro to you. It’s not rocket surgery, update your profile at least once a month – the more investors that are following your profile, the better off you’re going to be in the long run.
  • Pay attention to what you put above the fold. That real estate is precious, don’t fuck it up. Everything above the fold should be designed to (a) encourage the investor to click the follow/intro button or (b) scroll/click around your profile. Make no mistake though, the goal is to get them to request an intro – you’re raising money, right?
  • Pick the right product images/videos for your product. Humans are visual, spend an extra few minutes capturing the right screenshot or cropping the image to help clarify what you’re trying to show. Bonus points if you use shading or other techniques to draw the eye to the exact part of the image you want the visitor to look at. If you decide to use video, please be careful – you need to capture the visitor’s attention in <30 seconds. So uploading a three minute video is usually not a good idea.
  • Don’t tell people what you do, tell them why you’re awesome. Your readers are busy, so opening your product description with some vague statement about being the “X for Y” is lame. Explain your startup like you’d explain it to your non-startup friends. Or, better yet, as if you were explaining it to my mother. If you’ve received press mentions from recognizable places, I often recommend you lead with “As featured in the NYT, WaPo, and TechCrunch and on NBC, ABC, CBS…” and then leave one line of whitespace before you continue.
  • Speaking of whitespace, please use it. Paragraphs in your profile should not be more than 3-4 sentences. Make it super easy for the visitor to skim the profile. (And no, leaving the whitespace out isn’t going to “force” me to do anything. If your profile is hard to read, I’m probably going to move on to the next thing on my todo list.)
  • Sweat the details. I hate seeing profiles with unconfirmed team members. Seriously? These people are on your team, ask them to spend 100milliseconds to click the confirmation link that AngelList sent them – it seriously can’t get easier than that. Ask your investors and advisors to confirm their roles as well. (I’m guilty of taking a little while to confirm my investor roles with some companies but I’ll ask that you cut me some slack — our investment pace is, to put it lightly, on the aggressive side.)
  • It’s all about the faces. When I see the default avatar on AngelList, I die a little bit inside. SHOW ME YOUR FACE. Investors want to give money to real people, spend 30 seconds finding an image to upload. Once you’re done with that, make sure every other person on your profile has a face associated with their account as well.
  • Tell people how much you’re raising, but don’t share too many details. It’s important to mention the total amount of your fundraise and, optionally, how much of that is committed/closed already. However, I’d recommend that you avoid posting the actual terms of the round. IMHO, the goal of the AngelList profile isn’t to get me to make the funding decision on the spot — it’s to get me to request an intro and actually talk to you. You want to avoid the scenario where you may potentially lose interested investors because they simply don’t like your terms.

When in doubt, just remember that short and crisp is much better than the alternative. Show me enough to want to speak with you – not more, not less.