E2: “Angel” podcast: super angel & syndicate leader Gil Penchina on 20 yrs & 200+ investments, learning the game & making your own rules, which founders to back & avoid, optimizing deal flow, minimizing failure, & enjoying the chaos




about this episode

In episode 2 of Jason’s new podcast, “Angel,” Super Angel & Syndicate Leader Gil Penchina shares secrets from his 20 years investing in 200+ startups, including LinkedIn, PayPal, & Cruise. Gil reveals why he became an angel, which founders & verticals to back (& which to run away from), deal flow strategies, tips for learning the game & making your own rules, how to support founders, & lessons he’s learned from his greatest hits … and failures. Thank you to Audible for sponsoring this podcast.


0:00 Angel is brought to you by Audible.com.

0:27 What is the Angel Podcast about?

0:44 Introduction to Gil Penchina.

2:08 How did Gil get into Angel Investing?

2:53 What is the key difference working for big companies v. startups?

4:45 Gil explains 3 patterns for identifying when to invest.

5:37 Gil’s “Michael Jordan Factor”.

7:35 What is your advice for new Angel Investors?

8:40 How to learn Angel Investing before actually investing money.

9:37 What % of net worth should you invest into startups?

11:35 Advice for originating Deal-Flow.

13:25 What do you look for in deals?

15:30 Gil explains a situation where he had to fight for deal rights.

16:10 Gil’s favorite word in Venture Capital.

18:30 How do you manage your psychology in Angel Investing?

20:20 What percentage of Gil’s portfolio will fail?

20:33 What are Zombie companies?

22:23 When should you quit?

23:06 Dealing with pivots.

25:55 Gil’s criteria for selecting companies to invest in.

27:45 Two elements of traction.

28:19 Jason couldn’t wrap his head around AirBnb & Couch Surfing.

30:09 Gil opens his house to strangers.

31:57 What do you love about Angel Investing?

32:25 Thank you Audible for sponsoring the show. Go to http://Audible.com/angelbook

34:56 Jason’s book of the week.

36:29 Gil’s current obsession.

37:58 Raising 35 million dollars in 24 seconds.

39:45 Gil talks about his biggest win.

41:08 Gil’s 750x return.

42:08 Gil’s favourite train wreck.

45:34 Concluding the episode with an important tip.

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