Go offline with the Player FM app!
Ignite VC: The Case for High-Velocity Investing in a Power Law World with Peter Livingston | Ep149
Manage episode 474685061 series 3515266
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.
157 episodes
Ignite VC: The Case for High-Velocity Investing in a Power Law World with Peter Livingston | Ep149
Ignite: Conversations on Startups, Venture Capital, Tech, Future, and Society
Manage episode 474685061 series 3515266
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.
157 episodes
All episodes
×Welcome to Player FM!
Player FM is scanning the web for high-quality podcasts for you to enjoy right now. It's the best podcast app and works on Android, iPhone, and the web. Signup to sync subscriptions across devices.