20VC: Why Follow-On Investments Are Always A Better Investment, Why Spray and Pray Investing Is Like The Stock Market & Why Startups Need A Board From Day One with Jerry Neumann

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Jerry Neumann is one of New York’s leading angel investors with a portfolio including the likes of The Trade Desk (IPO: 2016), Datadog and Flurry (acquired by Yahoo) just to name a few. Prior to angel investing, Jerry built the first open market for the pricing and exchange of real-time consumer data in the form of Root Markets. Jerry was also the Managing Director @ Omnicom’s Venture Capital Division where he enjoyed an incredible 5 IPOs from the portfolio.

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In Today’s Episode You Will Learn:

1.) How Jerry made his way into the world of VC in the 90s and why it was difficult to lose money in venture at that time?

2.) Why does Jerry believe that the vast portfolio construction model is “wrong” and a “dead end”? In what circumstances does Jerry believe “spray and pray” investing can work? Why does Jerry believe you can only have as many companies as you can actively help? How does this lead Jerry’s thinking on his own portfolio construction?

3.) Why does Jerry believe that startups must have a board from Day 1? What are the inherent benefits of having a board so early? In the earliest of stages, how should those board meetings be run? Who are the best board members Jerry has worked with? Why were they so exceptional? How does Jerry think about building board intimacy?

4.) Why does Jerry disagree with the conventional wisdom of Silicon Valley that price does not matter because the exit will either be huge or a zero? How has Jerry seen the best firms in their thinking on market price vs indicated discount price? How has Jerry’s thinking on price sensitivity changed over the years?

5.) Why does Jerry believe that the follow-on investment is always a much better investment? How does the risk-reward ratio change from initial to follow-on investment? How does Jerry assess and prioritize future financing risk when investing in an opportunity? How does he mitigate that as much as possible?

Items Mentioned In Today’s Show:

Jerry’s Fave Book: Console Wars by Blake Harris

Jerry’s Most Recent Investment: Edmit

As always you can follow HarryThe Twenty Minute VC and Jerry on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

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