Fred Wilson from Union Square Ventures on TWiST #161 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. 8:30-9:30 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? 20:45-22:30 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. 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? 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! Support This Week in Startups and independent media by joining the TWiST Producer Program at TwistList.co! Multilingual? Translate this episode of TWiST into another language and email the transcript to translate@thisweekin.com FOLLOW ON TWITTER Jason: @jason Fred: @fredwilson Union Square Ventures: @usv Special thanks to the members of the TWiST List Producer Program! Executive Producers Louis-Eric Simard, Benjamin Gifford, Jacek Artymiak, Octavian Mihai, Will Paoletto, Geoffrey Clapp, Eien Hyett, Jeff Hoffer, Kyle Lonzo, Austin Miller, Rashaun Sourles, Robb Kunz, Greg Berry, Sean Lynch, Mary Ann Halford, Jim Joyce, Morgan Howard, Margaret Johns, Kyle M. Brown, Paul Cole, Nick Duncan, Magnus Ingvarsson, Amir Ayalon, Carlos Zaidenweber, Avery Keitt, Joshua Shipsey Producers Eli Coler, Ted Inoue, Radek Rybicki, Hunter Owens, Christian Owens, Ben Altieri, Casey Wach, Cam Collins, Ildar Khakimov, Matti Hallanoro, Rodrigo Dauster, Rodrigo Fuentes, Anthony Ortenzi, Daniel de la Cruz, Michael Hofmann, John Meneses, Mike Sunyich 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, Patrick Altman, 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, Jo√£o 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

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