Lessons from Village Global

Seven and a half years ago, we founded Village Global. Since then: 300+ companies backed, $500M+ AUM, and dozens of lessons learned about how venture firms work.

I just published “30,000 Hours with Village Global” – a smattering and sprawling set of reflections and questions on what’s happening in early stage VC, the art and science of venture, and the hard questions about firm moats.

If you’re a founder, GP, or LP in the ecosystem, I’d love to hear your thoughts.

Forming Conviction and Talking About It on an Investment Team

For investors, conviction—the depth of your belief in an investment opportunity—is the most important compass.

And talking about your conviction with your colleagues is something that happens on every investment team. But it’s a minefield.

When the tendencies of how each person on an investment team forms and communicates conviction are poorly understood, it can inadvertently distort investment decisions, diluting fundamental analysis with interpersonal misinterpretations.

People’s Default Tendencies and Personality Traits

Personality and cognitive styles loom large when it comes to conviction.

Some people are simply more convicted people in general. They’re decisive. They love something—or they hate something. That oyster soup is damn delicious, or it’s reprehensible and get it out of my face. That Tesla Roadster is absolutely the model we should buy – or it’s definitely not.

Hell yes, or hell no. They’re gung ho personalities, decisive temperature, brimming with natural confidence. At their best, it’s not that these conviction-by-default people are incapable of subtle thinking. It’s more that their brains tend to work down or up from either a high or low starting point.

For example, I know investors of this breed who, upon encountering a credible opportunity, tend to start with 9 or 10 out of 10 conviction after one pitch. They default to, “What could go right?” They default to enthusiasm. As they undergo diligence, their enthusiasm sometimes lessens, and their conviction gets chipped away. If the investment gets done, the opportunity went from 10 out of 10 to 7 out of 10 – still above the bar.

There’s also the inverse. There are investors who start at “no” and default to skepticism. For whatever reason, they’re more jaded by nature. More cautious. They’ve seen too many failures. As they spend time with the founder, they warm up, and conviction creeps up from 4 out of 10 to 7 out of 10—and the investment gets done.

Still other types of people are equivocal by nature and tend to default to “both sides have good points”—they see the possible merits and demerits of every investment and have a measured way of forming and expressing opinions. These more deliberate people are constitutionally incapable of loving or hating anything – they start at 5/10 for everything.

All of these types of investors—the gung-ho, the skeptics, the aggressively even keeled—can arrive at 7 out of 10 conviction (or higher)—or whatever level necessary to pull the trigger on the actual investment.

Each person ended up in the same place. So I’d argue the difference in each person’s starting “conviction default” matter didn’t matter presuming it took each person the same amount of time to arrive at the right answer.

Talking about Conviction Casually Can Change Underlying Conviction in Unhelpful Ways

Investors gauge how much their partners believe in a particular opportunity by asking, “How much conviction do you have in this opportunity versus the others we’re looking at?”

In a team context where you talk about deals before a decision’s been made, these differences in personality and style as it relates to conviction introduce impurities as you try to calibrate how a colleague is thinking about an opportunity.

If you ask someone whose default posture is skeptical to provide an update on his in-progress thinking on a given idea, he might come off to the group as lukewarm. He’s still forming his views. His on-the-one-hand, on-the-other-hand narrative might undersell his potential to garner great enthusiasm. In that fragile state, the rest of the group might pile on to reinforce the skepticism—skepticism that may have had more to do with a personality disposition than fundamental analysis. And just like that, you’ve killed the deal.

These dynamics make it vital to know the tendencies of each colleague on the team, how they tend to default, and what “high conviction” sounds like in terms of the words they use and body language they display.

Recent Appearances and Interviews

I recently sat with Auren Hoffman for an hour on his World of DaaS podcast. We covered a range of topics — from talent spotting to the future of work to what’s happening in venture capital to lessons learned from Reid. Fun convo and the YouTube embed is below.

Also, separately, on the Village Global podcast, I interviewed:

  • Thejo Kote of Airbase (who recently sold his company to Paylocity) about how to scale an enterprise software business, hiring remote, doing customer development in the early days, and more.
  • Guillermo Rauch of Vercel (one of the hottest companies in Silicon Valley) about open source, AI, crypto, and more. Guillermo is a really clear business thinker who dropped out of school in his teens to code in his native Argentina.
  • Howie Liu of Airtable on his remarkable journey building one of the most used products on the web today, and some of his unconventional founder advice.

Village Global III

I’m pleased to share that we launched Village Global III, our latest $250M seed fund, and that Reid Hoffman is joining as Chairman.

Bloomberg News covered the announcement here.

Our formal blog post over is over at the Village Global site.

It’s been a very busy past couple years for me — working intensively on Village Global, reading a ton, and traveling to some far flung places. I hope to return to do more writing on this blog soon-ish about — among other things — Village, reading, and traveling!

The Future of VC and Lessons from Village Global

I was delighted to chat with Samir Kaji on his podcast Venture Unlocked about the history and strategy of Village Global, and a range of other inside baseball VC topics like portfolio construction. We launched the firm a few years ago; it’s been an amazing journey. Here’s the Spotify link or in Apple Podcasts. And embedded below.

By the way, if you’re starting a company this summer, apply to our Accelerator for a personalized, white glove experience alongside our investment. And also: A few months ago, we announced a $125 million Fund II.

Disclaimer: This presentation does not constitute an offer to sell or the solicitation of an offer to buy any security. No representation is being made that any investor or portfolio will, or is likely to, achieve profits or losses similar to those discussed. Targets discussed have been established based on several assumptions that may vary depending on the type of investment.  There is no guarantee that the conditions on which such assumptions are based will materialize as anticipated and will be applicable to Village Global’s portfolio investments.