Investor Stories 491: What Visionary Leaders at Jackpocket, Vercel, and Microsoft Do Differently(Peter Davis, Solomon, Vaidya)

0:00Vivek Vaidya: This episode is brought to you by Ramp, the spend management platform we use here at TFR. They're offering listeners$150 just to take a demo. We've never had an offer quite like this. Claim your$150 before this offer is gone at our partner link, ramp.com slash partners slash TFR. Now on to the episode.

0:23Nick Moran: Welcome to the podcast about venture capital, where investors and founders alike can learn how VCs make decisions and reach conviction. Your host is Nick Moran, and this is The Full Ratchet.

0:39Vivek Vaidya: Welcome back to TFR. On today's special segment, we ask guests to discuss the most visionary founder that they've worked with and what makes them so special. Here's the segment called Visionary Founders.

0:56Vivek Vaidya: on today's special segment we have mark peter davis of interplay ventures mark tell us about an exceptional founder you've worked with and the specific thing they do that's unique i'm going to give pete sullivan from jackpocket a shout uh pete uh was one of i think the first entrepreneur to come through our accelerator program and we had known each other he was an entrepreneur who's a bit of a unicorn. He has a rare combination of design and sales skills, which put together is quite magical for front-end consumer plays. I believe most of Jackpocket, for the folks who have played the lottery on Jackpocket, that art Pete actually made, right?

1:34He's really, really talented. Pete went through what I would kind of categorize as one of the most iconic journeys as a founder. He went into a highly regulated space. It took him, I want to say six to eight years to break through to the point where it was starting a hockey stick, which is a long time because there's regulatory battles. You know, the lottery is a huge market. It's something like three or four times as big as the movie market. It's huge. It's massive, massive, but it's run by the states. And so the customer that you have to get approval from are state governments. And there's a whole lot of screwy incentives in that.

2:10So lobbying's involved and applications and delays. he went through a really really hard journey a couple times i think almost went personally bankrupt fought the fight of all fights i actually have a podcast episode of my own where i talk to him about his story uh for those interested we can maybe link to it but it's a little bit old at this point but still relevant for what he went through but it was one of the most it could be a movie one of the most epic journeys ultimately the end of the day of the story is he not just didn't just have the right idea and all the right capabilities but the level of tenacity and grit that Pete exudes, we're going to be hard to find other founders at the same level.

2:50Vivek Vaidya: On today's special segment, we have Glenn Solomon of Notable. Glenn, tell us about an exceptional founder you've worked with and the specific thing they do that's unique. Working with Guillermo Rauch, the founder and CEO of Vercel, has been an incredible experience. Vercel is a tremendous company with a bright future in front of it, But back in early 2023, shortly after the launch of ChatGPT, Guillermo came to the Vercel board and announced that the company was going to burn substantially more capital in 23 than previously planned because he wanted to move from being the front end cloud to being the AI cloud over the coming 12 months.

3:34Guillermo conceived of and launched some of the most important and popular AI products on the market today during that 12-month period. And the company is literally now 10x the size it was at that moment because of that decision. That took serious vision and guts and willingness to take risk and push the company and market forward. really breathtaking and incredible, credible to work with Guillermo as a result.

4:08Vivek Vaidya: Are you still managing expenses with outdated apps and spreadsheets? If so, it's time for Ramp, the leading US spend management platform covering corporate cards, travel, AP, and more, all built to save time and extend runway. We use Ramp at TFR and it's been a game changer. As our preferred partner, they're offering listeners$150 just to take a demo. No need to sign up. Head to ramp.com slash partners slash TFR to claim your$150 before the offer expires. Now back to the interview. On today's special segment, we have Vivek Vadia of Superset. Vivek, if you had to choose one visionary founder or leader that has inspired you most, who is it and what about their leadership approach resonates?

4:54Nick Moran: I have to say, I don't like leadership styles of any of the erstwhile visionary founders. Whether it's Jobs or Musk or people ostensibly considered visionary, I don't like their leadership styles.

5:07Vivek Vaidya: Interesting.

5:07Nick Moran: I think there is a way in which leaders can be very, very effective and be good human beings. Is there someone that stands out that you think has done both? He's not a founder, but I like what Satya Nadella has done for Microsoft. I really do. And I'm saying that because I was there during the Steve Ballmer years, and I saw what kind of company Microsoft was at the time. And then I see what kind of company Microsoft has become now after Satya Nadella took over. It's like, you know, calling it night and day would be doing it a disservice. What's the biggest difference? I think he just trusts people more.

5:39Nick Moran: There was this very backstabby, competitive to the nature of, well, everything being a zero-sum game kind of culture at Microsoft. Satya has just trusted people more and empowered them, given them autonomy to do the kinds of things that they think is right for the business and then elevated them and they've delivered results. So his special skill, if you will, is one where he's picked the right leaders to do the work and entrusted them to do it well.

6:10Vivek Vaidya: That will conclude this installment of Investor Stories. If you're enjoying the program and would like to see it continue, take a moment and leave a five-star review in iTunes. Okay, that will wrap things up for today. Until next time, overprepare, choose carefully, and invest confidently. Thanks for joining me.

6:44Thank you.