Investor Stories 411: Lessons Learned (Patil, Schilling, Abel)
Episode
6 min
Read time
2 min
Topics
Career Growth, Productivity, Investing
AI-Generated Summary
Key Takeaways
- ✓Personal Capital Discipline: Swell VC founders invested their own limited money in 2008-2010 before raising LP funds, forcing extreme discipline to focus on founder DNA over hype cycles and market trends.
- ✓Asymmetric Risk Management: Headline's Matthias Schilling emphasizes staying consistent through market cycles—biggest mistakes come from not investing in high-risk opportunities and tightening up when markets collapse instead of accelerating.
- ✓Financial Prudence Post-Crisis: G2's Godard Abel credits near-bankruptcy experience for making him more careful about over-investing, maintaining closer focus on achieving profitability and positive free cash flow before expanding aggressively.
What It Covers
Three venture investors share career-defining lessons: investing personal capital first, managing asymmetric risk through market cycles, and maintaining financial prudence after near-bankruptcy experiences.
Key Questions Answered
- •Personal Capital Discipline: Swell VC founders invested their own limited money in 2008-2010 before raising LP funds, forcing extreme discipline to focus on founder DNA over hype cycles and market trends.
- •Asymmetric Risk Management: Headline's Matthias Schilling emphasizes staying consistent through market cycles—biggest mistakes come from not investing in high-risk opportunities and tightening up when markets collapse instead of accelerating.
- •Financial Prudence Post-Crisis: G2's Godard Abel credits near-bankruptcy experience for making him more careful about over-investing, maintaining closer focus on achieving profitability and positive free cash flow before expanding aggressively.
Notable Moment
Schilling observes half his VC peers stopped investing for six months after Silicon Valley Bank crisis, while he viewed the empty market as optimal timing for contrarian deployment.
Episode Transcript
This episode of TFR is brought to you by Ramp, the spend management platform we use here at TFR. They're offering listeners a $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/partner/tfr. And this episode of TFR is brought to you by the American Arbitration Association, where smart startups and investors turn to for fast, efficient, and cost effective dispute resolution. Visit adr.org/tfr to learn more. 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. Welcome back to TFR. On today's special segment, we ask guests to tell the most important lesson that they've learned in their career. Here's the segment called lessons learned. On today's special segment, we have Rusty Ralston and Jay Patel of Swell VC. Rusty and Jay, can you tell us a story highlighting a critical lesson that has changed the way you invest? Yeah. It's kind of been our shared experience. Right? Where one of the biggest lessons that Rusty and I learned early on, and this is kind of like the launch of small fund zero, like, that I've mentioned, you know, earlier, during an introduction was like this proof of concept fund. For us, it was like, we didn't really, if we want, we didn't have money. Right? Like, Rusty and I, it was like 2,000, you know, 2,008, 2,009, 2,010. Like, we were just about making rent, making it making, you know, things work as New Yorkers. We were early in our careers, and we made the decision to put our own money on the line before we ever raised a single dollar from LPs. And I talked a little bit about that. What no one talks about is that judgment, honing judgment, crafting judgment, you know, fine tuning it, sharpening it, if you will. Anything that's forced us to be extremely, extremely disciplined. When it's your own capital and risk, you don't have much data to go off, you learn real quick. Right? The early stage investing is not about jumping on hype cycle. It's not about following trends. It's not looking over other people's shoulders. It's all about the people. You better have conviction in yourself, better conviction in your own judgment, and you better bring something real and meaningful to the table that actually helps move mountains, you know, for the the founders that you invested. And it goes back to the investment in our trust talk. It was like the first angel check that we ever wrote. Right? What stood out at the time wasn't just a tech or the market potential. It was his DNA as a founder, who he was at the core, what made him tick. Right? Why was he a founder? Why was this company his life's work? And he had the track …
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