Angel: Gil Penchina


Super angel Gil Penchina has invested in 200+ startups throughout his career (incl. LinkedIn, PayPal). He and Jason riff about founder tenacity, how to deal with failing companies, and getting past your own biases.

0:00 Angel is brought to you by
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
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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