Excluding VC funds, I’ve directly invested in a few dozen startups. While the jury’s still out on my performance, I can share a few things that I’ve learned along the way:
- This isn’t easy. Though I’d never thought I’d say this: it’s given me some empathy for early-stage venture capitalists. Be prepared for ten-year-plus exit horizons and to lose every penny you put in.
- I mock VCs (a little) less. It’s easy to mock VCs for being too fashion-driven, too pedigree-oriented, and too herd-like in their behavior. But when I’m actually in their shoes evaluating seed-stage opportunities, I see myself adopting some of these very same behaviors. (Think: “it’s an AI data play, the founders dropped out of Stanford PhDs, and DCVC is leading the round? I’m in!!”)
- Access is everything. You can’t invest in a deal that you never see. This leads me to believe that you should only consider angel investing if you have access to amazing group of people who you think will do great things in the future (e.g., by having worked together at a startup seemingly destined to spawn many more).
- I can see the power law at work. While I have confidence that my returns will be quite good in the end (and marking them to market today is largely meaningless), I can already see that they will be concentrated in a few superstar investments.
I learned one of my more impactful lessons at an A16Z event a few years back. After the presentation, I went up to one of the partners and we spoke:
DK: Hey, I was looking at XYZ Co the other day thought you might be interested in taking a look at them.
A16Z partner: Yes, we know them. I recently had a few team members do a full run-down on that space — there are about a dozen companies in it — and we decided that while we like the space, they weren’t the team we wanted to bet on.
And a light bulb went off. When I find an seed-stage deal, I evaluate the founder, the story, the product, and then make a decision. When professionals find a seed-stage deal, they put a team of three MBAs on finding and evaluating every startup in the emerging space.
That’s a big difference. I never know if they’re the best team in the space. I can only know if I think they’re impressive.
This observation backed me into what I now use as my four-question framework for evaluating angel opportunities:
- Why this idea? Do people need this? Will they pay for it? How big can it be? Is this really a company or just a feature?
- Why now? Is this idea too far ahead of its time? Or, is this company too late?
- Why this company? Do they have a technological head start? Do they have uncommon expertise that is difficult or impossible to replicate?
- Why this leadership team? Why is this particular group of smart people (hint: they’re all smart) going to win? What is special about the founders that makes me believe they will beat everyone else and/or change the race as need be?
I know many such frameworks exist. I’m not making any uniqueness claim on this approach. I am saying, however, that this is my current framework when wearing my angel investor hat. And I think it’s really useful for founders to switch perspectives from time to time, so they can get a better sense for what the people on the other side of the table are thinking.
And, in the end, they’re thinking like investors. The more you can too, the better you’ll do when fundraising.
Posted in SaaS, Startups, VC
