Reboot Podcast With Jerry and Brad

Jerry Colonna, Brad Feld, and I go way back in the venture capital business. We met in the mid 90s and worked very closely together during the late 90s. I still work closely with Jerry and Brad but not quite as intensively as we did back then.

We got together a couple weeks ago (virtually) and chatted for an hour about the personal struggles we all dealt with and overcame as we grew up in the business.

It’s a pretty revealing discussion. I just listened to it and cringed a few times. Jerry has this uncanny ability to get people to say things they don’t often say. He did that well on this one.

There is a lead in of about five minutes. The conversation starts after that.

#entrepreneurship#VC & Technology

Comments (Archived):

  1. awaldstein

    I will let you guys in my head during my mid morning workout today. That’s almost as personal as it gets!

  2. William Mougayar

    Yeah, lots of F.. words flying around. Maybe the same number of times you cringed. ;)”Brutal honesty, delivered kindly.” – loved that line from Brad (and experienced it). It can go a long ways.

    1. awaldstein

      If this is vulgar my friend you live in a very gentle world 😉

    2. Chris DeRose

      Brad is just a troll

  3. jason wright

    Super conversation.Flatline Partners would probably not have been a success.

    1. Jess Bachman

      Oh man…. classic.

  4. Twain Twain

    THIS by Brad Feld: “Go native… Be concrete and deal with it as human beings” and his astute observations about “investor tells” and how they “create layers (barriers) between the people involved and the problem-solving”.Also really like Fred’s “company is sick patient that’s not even in room when founders+investors have board meetings” metaphor.I think back to when I did strategic investments (board observer for UBS in my 20s) and how different the experience is as a founder. As investor, I pushed for ROI to be booked yesterday. As founder, I know that seemingly “linear, A to B” milestones that investors think should happen … may not.We all keep learning and improving.

  5. pointsnfigures

    Great discussion. I will steal some of it for a class I am participating in on boards. One thing I have noticed with people-when they have money at stake, it gets very emotional despite all our efforts to make analytical decisions. Fred says, “Well, we only had $750k invested”. It’s important to know where your break point is.I see it happen all the time. People are over invested. They get scared.When I was trading, I saw it happen every day. That’s when the bad shit happened. Some people would do anything and compromise all in order not to lose. It’s what separated the stand up guys from the ones that were shady.It’s not about taking it “like a man” when you lose. It’s about trying to do everything to solve the problem-and give the company a chance to make it; without compromising your values, the CEO’s values, or the team’s values. And know, sometimes you are going to lose.

    1. creative group

      pointsnfigures:(“When I was trading, I saw it happen every day. That’s when the bad shit happened. Some people would do anything and compromise all in order not to lose. It’s what separated the stand up guys from the ones that were shady.”)————————————-Our experience is that the market volatility during the period of 1994 to 2000 was a direct result of Day traders speculation, pump and dumping, etc. The Bull run during this time assisted us and many in establishing themselves in the market. We had great wins and horrible losses. Online trading has developed fromthe buy and hold and day trade run to the knowledge based approach most online brokers offer clients. All we can say is what a run. And various ways it continues.

  6. Thor Snilsberg

    Guys, What a conversation! Thanks for sharing openly. Knowing my own anxiety, it is always refreshing to hear other entrepreneurs and risk takers talk about theirs. The ‘slap on the back that kickstarts my positive juices’ or the board members who recognize leaders make mistakes and says ‘you can fix them in 6 months if …’ are tales that lucky entrepreneurs can share.

  7. Sebastien Latapie

    “By the third time you do something you get it right” — Great motivation to keep going after it.

  8. Richard

    This is definitely Saturday Material 🙂

  9. cavepainting

    A brilliant and honest conversation !Advocating for the sick patient is a great metaphor indeed. But people often disagree intensely because they have different standards for what sickness is and isn’t at a particular stage of the business, the diagnosis of what is making the patient sick, what the remedy should be, and how long it should take.Yes, when the company hits a big home run or a grand slam, all stakeholders’ agendas are aligned, but the reality is 80% of the portfolio has to be optimized at some point for singles, doubles or minimizing loss of capital. How these conversations and situations are managed define and reveal the very human and complicated nature of this business.

  10. creative group

    CONTRIBUTORS:OFF TOPIC:Theranos Pulls “Bait-and-Switch”In a much-hyped presentation at a medical conference on Monday, Theranos CEO Elizabeth Holmes had been expected to provide some scientific and regulatory details on her troubled blood-testing startup’s Edison machine. Instead, Holmes pitched a new technology—the “miniLab,” which Theranos says will perform blood diagnostics remotely—that has not yet been approved by the Food and Drug Administration. Holmes told attendees at the American Association for Clinical Chemistry (AACC) convention in Philadelphia that this is “the beginning of the next phase of the company, as we introduce our technologies to the world.” But, medical professionals in attendance were reportedly miffed that Holmes avoided providing further details on the Edison machine that Theranos had previously pitched as a revolutionary technology before the company ended up tossing out two years-worth of blood test results amid questions over the tests’ accuracy and Holmes received a two-year ban from operating a lab.Source:

  11. David Noël

    Thanks for the openness! Great discussion.

  12. johndodds

    Five days but only 19 comments!That’s the sort of anecdata that confirms my prejudice that most people won’t put in the work to find the real nuggets of wisdom. Especially when they can fool themselves into believing that they’re learning something useful from that post or article that everybody’s retweeting (and maybe reading).Revealing discussions are the best and this one is advertised as such. So what are you waiting for?

  13. fredwilson

    Flat line. LOL.

  14. jason wright

    AKA the Fred & Jerry Cardio Crisis Club.