Feld / Calacanis Interview on This Week In Startups

I always enjoy hanging out with Jason Calacanis. We first met in the mid-1990s when Jason was hanging out in NY doing Silicon Alley Reporter. I can’t remember who initially introduced us – it was probably Fred Wilson.

We covered a lot in the hour+ interview for This Week In Startups. Things like why I didn’t retire at age 30, what Amy’s ring tone is, Startup Communities, Boulder, what motivates me, the different between mentors and advisors, my biggest failures in the Internet bubble, the Foundry Group investment strategy, my angel investment strategy, why Fred Wilson and USV has been so successful, why the objective of a VC is a straightforward and how to define success as a VC, why the answer to “how is a VC fund doing” is “check back in a decade”, hiring for culture fit vs. competence., why entrepreneurs get to – and should – define their culture, why you can’t change people (and how my first marriage blew up), why investors are like D&D characters, examples of bad behavior of VCs and entrepreneurs, more stuff about VC and entrepreneur interactions, what the best board meetings are, a reminder that people lie, Lance Armstrong and ego, CEO coaches, the first person I ever fired, and a bunch of other stuff.


Jason – you are the Internet’s Charlie Rose. Well done.

  • http://ohheyworld.com/ Drew Meyers

    Enjoyed the discussion — particularly your thoughts at the end on the importance of a peer group for a founder. I totally get the importance of mentors, and am lucky to have a good support group in that regard, but hadn’t really thought much about the importance of a peer group of fellow founders going through the same things. Until now that is..

    • http://www.feld.com bfeld

      One of the most powerful experiences I had in my first company was when – at 24 years old and about a dozen people working for us I went to Birthing of Giants and then ended up joining the Young Entrepreneurs Organization (now EO – http://www.yeo.org). It was the first time I “found” my peer group and it changed my life as an entrepreneur.

  • Andrew

    I enjoyed the interview. You guys touched on a ton of topics… best part was Rule #1 – 12:40 mark. Took me a few years, one company, and a relationship to figure this out, but now I get it.

    • http://www.feld.com bfeld

      Awesome you figured out rule #1! Amy and I talk a lot about it an others in our new book Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur – http://startuprev.com/lifebook

  • http://www.facebook.com/dain.carver Dain Carver

    As a first time entrepreneur, I felt that there were three great takeaways from this 1) Things can always go from bad to worse; just be ready to roll with the punches 2) The preservation of a company’s culture is sometimes more important than the product/service itself and 3) The relationships that you build and maintain will define the success of your company. Are there any other lessons that I may have missed?

    • http://www.feld.com bfeld

      I think those are three great ones are a great interpretation of what I was saying.

  • http://twitter.com/andyidsinga andyidsinga

    enjoyed the interview …love your philosophy about choosing entrepreneurs obsessed with their product.

    • http://www.feld.com bfeld


      • http://ohheyworld.com/ Drew Meyers

        I know a certain someone obsessed with building the best travel product in the world.

  • http://byJess.net/ Jess Bachman

    Wow.. yeah packed interview. Jason is a true pro at this, I hope he keeps doing TWiST for a long time. He deserves more credit for the service he is providing, imho, It’s what he was born to do. Brad you always come across as so rational. Your attitude reminds me of the Slow-Food movement. #Slow-Investing?

    • http://byJess.net/ Jess Bachman

      Also… please do a post on Agile boards!

      • http://www.feld.com bfeld

        Coming soon!

  • http://blog.damonc.com/ Damon Clinkscales

    enjoyed every minute of it, Brad!

  • Jeffrey Hartmann

    Loved the interview.

    Just personally curious though what D&D class you think you fit into? I think a new class is in order, perhaps Brad the Venture Mage, wielder of Dark Startup Magick and Yoda-like Advice? Or maybe perhaps a Venture Paladin, loyal to the God of give before you get? What do you think?


    • http://www.feld.com bfeld

      Love ‘me both! I’m definitely not an Orc.




  • http://www.facebook.com/colingonsalves Colin Gonsalves

    A lot of takeaways in this interview. You and Jason really captured the feelings a first time entrepreneur goes through. Thank you both!

  • http://www.engag.io/Abdallah Abdallah Al-Hakim

    started watching this and impressed that you answered the phone call from Amy! Great intro for your new book about living with an entrepreneur (nice ringtone as well :)

  • http://twitter.com/tomleelong Tom Long

    Great interview. Just picked up the Tyler Hamilton book. You should check out the Southpark episode about Lance, “Scause for Aplause,” if you haven’t. It’s one of the more recent ones. Quality.

  • Jeremy Norton

    Great interview! I got so many information.

  • Zeitgeist Movie

    Aren’t you at CES to pimp that stupid fucking $130 cat toy????

  • Dasher

    Awesome Interview. Very candid. Thanks.

  • http://engag.io/ William Mougayar

    I finally got to listen to it. Great interview, and Jason is killing it with this format. Definitely Charlie Rose-sque.

    I liked your concept of Continuous Engagement during the BOD segment. Was like a peak preview of the book I presume? i have seen the case where the VC critiques, pulls out and does it again 6 weeks later. Not only is it detrimental, it’s also immature behavior.

    And you had fewer “bleeps” than @howardlindzon!

    • http://www.feld.com bfeld

      Yup – I’ll talk more about continuous board engagement in the Startup Boards book.

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  • http://twitter.com/jennieyko Jennie

    Great interview! I like how it flowed like a conversation. I think it was more dynamic and fluid for the viewer than a straight Q&A format. Discovered a lot of great advice not just on start up matters but on life too. ” We all die in no particular order ” gave good perspective on the challenges and changing priorities of an entrepreneur and its board. I actually went back a couple of times and marked TRT on some of the topics.. Be interesting for Youtube to create a mini bookmark tool inside the player for the publisher to create their own table of contents. Thanks again. Cheers.

    • http://www.feld.com bfeld

      Thx – I had fun doing it. I always love interviews with Jason – he brings out good stuff.

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  • Doc Sheldon

    Fantastic interview/conversation, Brad. I’ve suffered the drive-by board members before – it is SO disruptive and counter-productive!
    I love Rule #1… I admit, I struggle with that one now & then… the timing can be incredibly bad sometimes. I just try to remind myself why I do what I do.
    Off to order Startup Life now!

  • Ingrid

    My favorite line…”I booted up version 47 of myself recently”. Awesome. I am going to use it.

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