In this episode of the Ignite Podcast, Brian Bell interviews Peter Livingston, founder and GP of Unpopular Ventures. Peter shares how his journey from being the first engineer at iRhythm to an angel investor was shaped by early lessons in under-compensation and startup chaos. After a frustrating experience with equity negotiations, he pursued an MBA at Stanford, which expanded his network and perspectives. A failed startup post-MBA proved more educational than his earlier success and underscored his desire to work with high-upside, early-stage companies. These formative experiences laid the groundwork for his contrarian investment philosophy.
Initially unable to raise a traditional fund, he turned to AngelList syndicates, finding significant traction with a high-volume, low-check-size approach. Today, Unpopular Ventures backs 100–150 startups a year with $25K–$50K checks, emphasizing founder quality, idea-market fit, and differentiated geography or business models—often betting early on overlooked but high-potential startups like Zepto and Yassir.
The conversation also dives into the logic behind large portfolio construction, comparing it favorably to traditional diversification and unpacking why “spray and pray” is a mischaracterization. Peter shares his view that the best early-stage investments come from founders with hints of past exceptionalism—even if not conventional success—and emphasizes the importance of understanding how many risk vectors a deal presents. He cautions against backing founders without any entrepreneurial or technical signal and advocates for a strategy that blends broad exposure with tight founder quality filters.
Chapters:
Welcome & Guest Introduction (00:01 – 01:06)
From Engineer to Investor (01:07 – 05:14)
The Value Disconnect in Engineering (05:15 – 09:49)
Stanford MBA and a Startup Failure (09:50 – 14:37)
Valuations Then vs. Now (14:38 – 17:00)
Leaving Corporate VC Behind (17:01 – 19:04)
Angel Investing (19:05 – 21:55)
The Founding of Unpopular Ventures (21:56 – 23:08)
Scaling with SPVs on AngelList (23:09 – 26:00)
High-Velocity Investing & Portfolio Construction (26:01 – 28:32)
Venture Diversification vs. Spray and Pray (28:33 – 31:00)
Fund-of-Funds Incentives & Industry Dynamics (31:01 – 37:05)
The Yassir Bet: Super App in Africa (37:06 – 44:37)
When Founders Invest Their Own Capital (44:38 – 46:44)
Managing Risk in Emerging Markets (46:45 – 50:10)
What Great Founders Look Like (50:11 – 53:00)
Red Flags and Hard Passes (53:01 – 55:33)
Build First, Pitch Later (55:34 – 59:00)
Lessons from 450+ Investments (59:01 – 01:04:20)
Final Thoughts & VC Advice (01:04:21 – 01:07:19)
Outro & Where to Find Peter (01:07:20 – 01:07:43)
Thanks to Byldd for sponsoring this episode! Byldd helps startups rapidly build and launch revenue-generating SaaS and marketplace businesses with cost-effective, scalable solutions - Get Started Here.
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I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
Dateline NBC
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