E10: “Angel” podcast: Matt Brezina, investor in 65+ startups (Dropbox, Cruise) & founder (Xobni, Sincerely) shares strategies for backing relentlessly resourceful founder-builders & bringing operational value in return

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In “Angel” episode 10, Jason talks with Matt Brezina, angel investor in over 65 startups, including Dropbox, Cruise & Ring, and also founder of Xobni & Sincerely. Matt shares how & why he got into investing, his critical formative time in YC, the lasting influence of Paul Graham, meeting Drew Houston (failing to hire him, but succeeding in investing in Dropbox down the road…), learning sales from his mom, mistakes letting ego interfere with business, why he loves Twitter, the future of transportation, his belief in the power of founder-builders and investing in their careers…and much more.

0:01 Angel is brought to you by Audible. Go to http://audible.com/angelbook to receive a free audiobook & 30-day trial.

2:07 Introduction to today’s guest: Matt Brezina.

2:44 When did you get into Angel Investing? Matt talks about his journey to becoming an accredited investor, and making his first investment into Dropbox.

4:21 Jason & Matt talk about the stage when Angel Investors are unable to provide value to a startup. Matt shares the story of how he met Drew Houston (CEO, Dropbox).

6:13 Matt explains how Dropbox was ahead of its time, and how incredible Drew Houston was as a technologist.  

8:34 Matt explains the sequence of events that led him to Angel Investing. Investing into public stocks at young age, developing skills from his parents, starting his own company, and now investing into tech startups.

10:57 Matt shares the story of his first employees creating large startups, and how his ego got in the way of a $500M exit.

11:28 Jason & Matt talk about Ring (smart doorbell) and Jason explains why he passed on investing.

13:43 What do you look for in entrepreneurs? Matt explains the characteristics that guide his decision to invest v. not invest in a startup.

17:34 Jason explains his frustration for founders who can’t explain what they’re building. And asks Matt if he would ever invest in a founder that hasn’t built anything, or only willing to start when they receive funding.

19:14 Jason and Matt discuss the importance of founders building something that they want for themselves. “Whether it makes money or not, you have an itch and want to see it manifested in the world.”

20;39 Matt explains the mission for his first company. What he realized while working in a corporate environment, and how it shaped him. “I wanted to build a company that I wanted to work at.”  

22:16 Do current high valuations affect your investment decision? Matt explains his thesis for investing in founders, rather than valuing the startup at an early stage.  

24:38 How do you deal with the consistent failures/bad news associated with Angel Investing? Matt talks about the importance of time allocation, focussing on the winners, and having monthly updates.

29:19 Is it important to look at the market size of an industry? Matt explains why he benefits from analyzing the market. And the magic spot for identifying a potential big company. (exe. Airbnb)

33:00 Matt shares his current passion for hub-less bike-share, and why he’s investing in this space. Also, Matt discusses the key factors that lead to mass adoption.

38:20 Thank you Audible for supporting this podcast. Go to http://audible.com/angelbook for a free audiobook & 30-day trial.

42:06 Jason hints at writing a follow-up book for Angel?

43:23 Jason & Matt explain the added benefit/competitive advantage of investing in Silicon Valley.

47:50 Jason has an idea to fix transportation in the Bay Area. Calling all founders for a request for startup.

49:45 Matt talks about his investment in Cruise (acquired by GM), explains what happens after a deal closes, and why he skipped the first round of Cruise.

52:37 Jason shares his most important rule for Angel Investing, which he learned after missing Twitter & Zynga.

53:24 Matt talks about why he loves Twitter. And how he uses it to add value to his life.

55:40 Jason & Matt both discuss the books that they’re currently reading.

1:00:04 Matt talks about his Weebly deal. And how he got advisor shares. Also, he explains the classification of light v. deep advisor shares.

1:03:44 Matt explains his process of reference checking, to decrease the risk of dealing with difficult founders.

1:05:45 Jason and Matt talk about why jerks don’t make it far in Silicon Valley. And why they’re seen more in a Corporate America environment.  

1:07:03 Matt & Jason both share an investment in 15Five. Matt explains what he loves about the company.

1:13:23 Matt talks about Teachable, another portfolio company of his. How he met the founders, and the early days of Y Combinator.

1:17:38 What if Angel Investing was a government job? Jason explains why he believes Angel Investing is a profession. And how Venture Capital has gone from people with top-tier MBA’s to now operators and journalists with connections and value-add.

1:22:55 What’s your kill-zone? Matt explains when he loves to engage with a company. And the importance of a technical co-founder.

1:24:31 Join Matt’s syndicate here: https://angel.co/brezina/syndicate. Jason & Matt briefly talk about cryptocurrency, and why they’re not investing… yet.    

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