About this Episode

TWiST #161 with Fred Wilson from Union Square Ventures
East coast super VC, blogger and adviser Fred Wilson of Union Square Ventures sat down to talk to Jason in his NYC office and had heaps of valuable advice for entrepreneurs young and old alike. Fred talked about the ups and downs in his lengthy career, explained why he wants founders to get to know him early on and explained why VCs still have something to offer, even in the golden age of angel investing.

0:00-1:00 Welcome to TWiST from NYC in the Union Square Ventures‘ offices.
1:00-2:00 Thank you to iStockphoto for sponsoring the show.
2:00-6:30 Demonstration of how easy it is to purchase high-quality photos within iStockphoto.
6:30-8:00 Welcome to Fred Wilson, principal at Union Square Ventures.
8:00-8:30 Jason: The biggest mistake of my career was not listening to [Fred’s] wife when she advised me to go national with Silicon Alley Reporter.
8:30-9:30 How much of being a VC is being a therapist to the entrepreneurs?
9:30-10:30 You’ve worked with Mark Pincus, what was that like?
10:30-11:45 You invested in all four of Mark’s companies, yes?
11:45-14:00 When Mark came to you for the fourth time with Zynga, what did you say?
14:00-15:15 The same sort of situation happened with Twitter, didn’t it?
15:15-16:30 If a VC flies out to see you–the entrepreneur–you know there’s serious intent.
17:45-19:15 So speed is the big difference between web 1.0 and now?
19:15-20:15 Have you ever spoken for your companies too much on your blog?
20:15-20:45 Your blog has really made you into one of the most well-known east coast VCs around today.
20:45-22:30 How much of your success this time around has been because of the blog?
22:30-23:30 Did you enable too much transparency and lose some of your power?
23:30-24:30 If money’s not an issue, why go to a VC?
24:30-25:00 Are there funds that are now following Union Square Ventures?
25:00-26:00 Thank you to MailChimp for sponsoring the show.
26:00-29:30 Demonstration of how you can segment your lists to target your emails using MailChimp.
29:30-30:00 Fred explains why he would like to see entrepreneurs work backwards and think about who they would like to invest in them.
30:00-32:15 How do you reconcile this, the new golden era of Internet companies, with the scars you have from past fund failures?
32:15-33:00 When do founders start thinking, “I should start a new company?”
33:00-35:15 Let’s talk about entrepreneurs. What are you looking to see in the eyes of an entrepreneur?
35:15-37:00 So you’re looking for a persuasiveness that is so strong, people can’t help but follow that person?
37:00-38:15 Do you find that this new generation of founders has an entitlement issue, thinking that they’re owed success?
38:15-39:15 Does that make that person impossible to manage?
39:15-42:15 Are you on the secondary markets? What’s your take on that?
42:15-43:45 Fred: Are Mahalo shares being traded?
43:45-45:30 Are limited partners stoked about the secondary market?
45:30-46:15 Why does a venture firm put money into a single established company and not into several startups?
46:15-48:30 What does an opportunity fund mean?
48:30-49:00 Fred: In the private equity business, you buy one and you’re done. In the venture business, you make multiple investments and the risks are mitigated.
49:00-50:40 What’s your advice for a young entrepreneur who wants your money?
50:40-51:15 Fred, it’s been great to watch you rise over the years. Thank you so much.
51:15-51:45 Thank you again to our sponsors. We appreciate all of your support!

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Jason: @jason
Fred: @fredwilson
Union Square Ventures: @usv 

Special Thanks to the members of the TWiST List Producer Program!
Executive Producers

Producers

Associate Producers

  • Brad Pineau
  • Kat Ganesan
  • Nicholas Christian
  • Mau Frontier
  • Kyle Braatz
  • Serena Ehrlich
  • Nathan Hangen
  • Lauri Hahne
  • JD
  • Trudy Baidoo
  • Ian Gerstel
  • Julian Hearn
  • Alex Lotoczko
  • James Kennedy
  • Benoit Curdy
  • Asher Nevins
  • Mike Kaltschnee
  • Paul Higgins
  • William Doom
  • David Lee
  • Jake Kerber
  • Sarp Coskun
  • Giuseppe Taibi
  • Tyrone Rubin
  • Keno Vigil
  • Paul Peters
  • Jamal Waring

Supporters

  • Ryan Hoover
  • Michael Cranston
  • Josiah Thomas
  • João Fernandes
  • Petrus Theron
  • Michael Wild
  • Adrian Grant
  • Dale Emmons
  • Kieran McGrady
  • Tim de Jardine
  • Alejandro Vasquez
  • C. Dain Miller
  • Joshua Opatz
  • Milan Babuskov
  • Chris Rowe
  • Nelson Melo
  • James Dawson
  • Toddy Mladenov
  • Daniel Torres
  • Chris Macke
  • Piotr Zuralski
  • Armand Konan
  • Brian Vogel
  • Paul D
  • Jennifer Sun
  • Zach Fogelson
  • David Kolb
  • George Gecewicz