Investor Stories 495: Perseverance at Roofstock, Speed at Zero, Discovery at Anduril — Why These Founders Stand Out (Black, Chen, Fubini and Patel)

Nick Moran (0:00)

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Now on to the episode.

SPEAKER_2 (0:24)

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.

Nick Moran (0:40)

Welcome back to TFR. On today's special segment, we asked 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.

On today's special segment, we have Ben Black, Managing Director of Akkadian Ventures, CIO of PowerLaw Corp and Founder of Raise Global. Ben, tell us a story about an exceptional founder you've worked with and the specific thing they do that's unique.

Ben Black (1:12)

Well, my favorite founder is really a story of perseverance. Gary Beasley is a long time entrepreneur in the PropTech space. He's the CEO of a company called Roofstock. And Roofstock has had an incredibly tumultuous journey. Roofstock is a marketplace for buying and selling single family home real estate and managing it. It's like a full service marketplace that's kind of everything around single family home real estate. And that space was incredible for a while. Interest rates went up, hammered. And now there's all sorts of external pressures on it. And Gary is still working on it to this day. And he has recreated that company like three times before my eyes. Pivoted to something new to turn the card and find something new again. And I think that that kind of perseverance in Silicon Valley is so rare. Yeah. I've backed a lot of hot founders, right? And the first time things get really, really hard, they go like, well, I'm just putting a bounce off and do the next one. Besides the fact that he's just a great operator, and he has the true ability to both be an external CEO, as well as running a really good company.

He picked a really hard space and he has recreated the company again.

And I just respect him so much for that.

Nick Moran (2:37)

On today's special segment, we have John Chen of Fika. John, tell us a story about an exceptional founder you've worked with and the specific thing they do that's unique.

John Chen (2:46)

I think Jake Cronin at Zero is an incredible leader of people. But the one thing that I admire most about him is his ability to make decisions with 70% information. And this is obviously like everyone talks about this, but it's much like when you see it in action, like you know what it looks like. Because I typically tend to be a much more deliberate decision maker.

I want to check all the corner cases and I want to sleep on it and rotate it around and turn an idea around. He turns the speed of decision making into an advantage.

He takes in all the inputs, he weighs it, and he's able to actually calibrate what's at stake in a decision very quickly and also determine is this a one way door where we can't reverse it or not. And get to the bottom of, OK, well, now we're going to move in this direction. And usually it makes me uncomfortable. It's like, whoa, whoa, whoa, we haven't actually fully bottomed out on what all the scenarios C and D and E. But I think that the speed of decision making is like, he's usually, he's sometimes right and he's sometimes wrong. He's usually right. The ability to make it quickly just means that he's able to iterate much faster and learn from those lessons. And I think that's a really important trait in a leader, especially in today's world where there is so much uncertainty about what is here to stay and what's a fleeing trend.

Nick Moran (4:11)

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/partners/tfr to claim your $150 before the offer expires. Now back to the interview. On today's special segment, we have Ross Fubini and Manish Patel of XYZ Venture Capital. Ross and Manish, tell us about an exceptional founder you've worked with in the specific thing they do that's unique.