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The Full Ratchet

Investor Stories 433. The Art of Sensing Greatness, From Analytical to Intuitive Investing, and the Case for Industry Outsiders (Hsieh, Hilaly, Maples)

7 min episode · 2 min read
·

Episode

7 min

Read time

2 min

Topics

Investing, Startups, Software Development

AI-Generated Summary

Key Takeaways

  • Industry outsider advantage: Founders without industry experience often drive exponential disruption versus incremental improvement, challenging the conventional wisdom of investing only in domain experts with lived experience.
  • Analytical to intuitive evolution: Experienced investors shift from asking whether a path to scale exists through analysis to sensing whether a business feels like an outlier that challenges worldviews.
  • Founder greatness trumps diligence: When encountering rare founder greatness, invest immediately rather than passing due to diligence concerns. Kyle Vogt's Cruise returned 94x despite team objections about unclear monetization paths.

What It Covers

Three venture investors reveal how their investment approaches evolved from analytical frameworks to intuitive pattern recognition and recognizing founder greatness over market analysis.

Key Questions Answered

  • Industry outsider advantage: Founders without industry experience often drive exponential disruption versus incremental improvement, challenging the conventional wisdom of investing only in domain experts with lived experience.
  • Analytical to intuitive evolution: Experienced investors shift from asking whether a path to scale exists through analysis to sensing whether a business feels like an outlier that challenges worldviews.
  • Founder greatness trumps diligence: When encountering rare founder greatness, invest immediately rather than passing due to diligence concerns. Kyle Vogt's Cruise returned 94x despite team objections about unclear monetization paths.

Notable Moment

Two veteran investors admit their biggest regrets came from passing on founders who emanated greatness because other diligence factors overshadowed that rare quality they initially sensed.

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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 describe the biggest change to their investment philosophy over the course of their career. Here's the special segment called rewriting the playbook. Today's special segment, we have Vince Shea of Cypress. How has your philosophy or approach to investing changed over the course of your career, and what's one belief or approach that you used to have that has since changed? It's a very common trope to say that, you know, you wanna invest in founders who have lived the problem, you have lived had the pain, have been in the industry for twenty years or subject matter experts. And I still very much believe that's that's generally true for for most investors. You wanna invest in subject matter experts who who who know the space. But I think that's a recipe for great kind of linear growth or linear success where you're incrementally making something better. In the industry you came from, you live this pain, you wanna get rid of the pain, so you do something that makes it incrementally better. If you want exponential change though, oftentimes it actually helps if you wanna disrupt something from the out it's coming from the outside. Someone who's not from that industry, not from that whatever space, that could mean they're younger, that can mean they're from a different space and they they lived and experienced somewhere else that they can then apply to that new industry or the new industry they're in. And if you really wanna disrupt something and have exponential growth versus just linear growth, I think some of this actually helps to have that outside perspective. Commonly, people talk about Elon Musk disrupting industries that he had no experience with before. Right? So I think that's one thing that, evolved my my thinking as an investor on in the few years I've been doing this. On today's special segment, we have Arif Hilali of Bain Capital Ventures. Arif, how has your philosophy or approach to investing changed over the course of your career? I think I used to be more analytical, and it's now more intuitive. So before, I I might ask, so does this make sense? Can I see a path to a huge company? What analysis …

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