upside

Interview begins: 5:16
Debrief: 43:55

This week we’re revisiting CC058, a coffee chat with Peter Livingston of Unpopular Ventures. In this episode, we explored syndicate investing.

Unpopular Ventures is led by Peter Livingston, whose experience is almost entirely in startups – as both an operator and investor. He was the first engineer at iRhythm (IPO 2016) and was the founder/CEO at Lifesquare (backed by Kleiner Perkins).

He has been angel investing since 2013, made >150 investments to date, and has produced investment returns well within the top decile of VC industry performance.

Peter founded Unpopular Ventures to keep investing in startups – but with a bigger family, bigger checks, and bigger impact.

We discuss:
- Disagreeing about corporate VCs (9:11)
- Syndicate Model (13:37)
- Investors and the syndicate (16:13)
- Not following the traditional fund (26:35)
- Building trust (31:25)
- Edification (39:23)

Learn more about Unpopular Ventures: http://unpopular.vc/
Follow Peter on Twitter: https://twitter.com/unpopularvc
Follow Peter’s Syndicate: https://angel.co/unpopularvc/syndicate

Follow upside on Twitter
https://twitter.com/upsidefm

Advertise with an upside classified
https://upside.fm/classifieds

Show Notes

Interview begins: 5:16
Debrief: 43:55


This week we’re revisiting CC058, a coffee chat with Peter Livingston of Unpopular Ventures. In this episode, we explored syndicate investing.

Unpopular Ventures is led by Peter Livingston, whose experience is almost entirely in startups – as both an operator and investor. He was the first engineer at iRhythm (IPO 2016) and was the founder/CEO at Lifesquare (backed by Kleiner Perkins).

He has been angel investing since 2013, made >150 investments to date, and has produced investment returns well within the top decile of VC industry performance.

Peter founded Unpopular Ventures to keep investing in startups – but with a bigger family, bigger checks, and bigger impact.

We discuss:
  • Disagreeing about corporate VCs (9:11)
  • Syndicate Model (13:37)
  • Investors and the syndicate (16:13)
  • Not following the traditional fund (26:35)
  • Building trust (31:25)
  • Edification (39:23)


Learn more about Unpopular Ventures: http://unpopular.vc/
Follow Peter on Twitter: https://twitter.com/unpopularvc
Follow Peter’s Syndicate: https://angel.co/unpopularvc/syndicate


Follow upside on Twitter
Advertise with an upside classified

What is upside?

Named a top 27 business podcast by Fortune, upside examines startup investing outside of Silicon Valley.

Every Wednesday, we speak with an early stage founder. We interview them as if we are angel investors considering the company as an investment opportunity.

Each show has three segments:

1.) Intro: independent research of the company
2.) Interview: interview with the founder
3.) Debrief: breaking down the opportunity

Sometimes, we share Coffee Chats interviewing venture capitalists, community builders, and later-stage founders.

Subscribe and see why Business Insider called our podcast "Almost as Good as Getting an MBA."