What Is Your Next Career?

I was recently asked the question “What is your next career?” as part of a discussion with an LP.

I thought it was the best diligence question that I have ever been asked. Upon reflection, the LP was clearly asking me indirectly about my long term commitment to venture capital and, without asking “how much longer are you going to do this VC thing?” she was looking for how I answered the question to get an understanding for how I thought about what I was currently doing along with an indication of how much longer I’d be doing it.

My quick answer was “I don’t have one.” I then unpacked this a little, explaining that I’ve never really thought about what I did as “a career.” While I have a LinkedIn profile, I’ve never had a resume, nor do I really feel like I’ve been on a career path.

But I realized that wasn’t an answer so I continued reflecting out loud in real time. I stated that when I think about it, VCs typically end up doing three different things after they stop being VCs: (1) be a CEO of a company, (2) politics, or (3) academia.

None of these appeal to me. I’ll never be a CEO of a company again – I did this for seven years between age 21 and 28. I was a good CEO but I never enjoyed the job. I have exactly 0.000000% in ever running for a political office. And, I was kicked out of a PhD program when I was 24 and have no interest in ever being a professor or an administrator.

I’m sure there are other things VCs do after stop being VCs, but I’m quite clear that I don’t have a next career in me.

  • Book publisher?

  • It seems that you have a perfect platform to learn new and interesting things. Why change that?

  • Ha ha, brilliant => “I don’t have a next career in me.”

  • mbyrne

    I hope the LP shared what her next career was going to be, because it’s pretty clear that was what motivating the question.

    • She didn’t. And I’m not sure I agree – she had been in her role for many years and was a leader in a very successful firm. I think it was – instead – a standard diligence questions of hers for people like me who have been VCs for a while.

      • mbyrne

        Yes, I know I was completely overstating the certainty of that, but honestly (confession) I was trying increase the odds you would respond because I was very curious of what she might have said regarding of her own situation. Says something if people don’t express reciprocity in terms of personal exchanges like that. I do find that what people criticize others for, tends to be an issue they are dealing with themselves, myself included. Maybe it’s called “projection” in psychology. I get the diligence idea, but still… Anyway, thanks for the response. I appreciate it.

  • Maybe devote 20 hours a week to a not-for-profit cause that’s really important to you – get some dirt under your fingernails, rather than solely working at the advisory or executive level.

    • Amy and I are deeply involved in many philanthropic efforts and our goal is to give all of our money away while we are alive. We’ve created several non-profits – separately and together – and will continue to do that.

      But I don’t view that as a separate career.

      • Rick Mason

        Maybe you should. Lots of times making the world a better place requires more than writing a check, it requires leadership and a commitment. Everyone is busy working 8 to 5 so worthwhile projects flounder.

        When I finish being an entrepreneur I’m going to work as hard giving away the money as I did making it, maybe even harder.

        • “Leadership and commitment.” I think this is something we do with our philanthropy. We do much more than just write a check. But I don’t view it as a separate career.

      • Ben King

        Your decision to give away your money while you’re alive is something you’ve talked about before and something I really respect.
        Have you ever thought about starting a VC-style firm that was devoted to building as many profitable businesses as possible, but with an eye to taking most/all of the profit and reinvesting it into additional ventures? Something like a mashup of Pioneer Square Ventures and a traditional non-profit?
        I’m not trying to pitch you here. This is something I have been thinking about and writing about on my own blog for about a year. I’d be very interested in your perspective as somebody who’s been down the startup/VC road a time or two.

  • Rosey

    My answer: “I don’t have, nor have ever had, or sought a career. I pursue a place of mindfulness and purposefulness, moment by moment. I’ve been blessed to get a few moments right that have, for me, provided enough sustenance to continue the pursuit. Any next moment has the potential to reset my focus, but it would have to be very compelling to do so.”

  • hmmm .. the last time someone ask me that question, I was about to be fired. : )

  • Randomness is good at this stage where you may not be really seeking something specific. Two, spontaniety has its own merits and charm…. if we are prepared enough. 🙂

  • A teacher, a real-life venture investor himself, once said to me that venture is the very last career you should ever want. If everything works as it should, if you do your job right, and you have a bit of luck, you’ll never have to work again (unless you want to).

  • Marathoner But in a different way.

  • conorop

    I’m a long ways from retirement, but I always thought it would be interesting to start a school. It’s both entrepreneurial and philanthropic.

    That being said, I wouldn’t mess with a good thing.

  • You’re not thinking radically enough.

    Step completely sideways to reinvent yourself e.g. write science fiction. As a side effect such a redefinition will slow down time for you.

  • You’ve mentioned in a comment above about planing to give your wealth away while you’re alive. How do you time something like that? I suppose you do it gradually once reaching a certain age.

    • We have been giving away at least 10% of our previous years AGI for over 20 years. Sometimes it gets as high as 20%. More recently, we’ve started contributing meaningful amounts of any current non-income (e.g. asset based) gains to our foundation. We are 50 and 49 so hopefully we have plenty of years in front of us, but we are quickly reaching the point where we are giving away a meaningful % of our annual “net profit” (as individuals) – eventually getting to 100% of it. It’s not a magic formula, but it’s behavioral and intentional.

      • Thanks for answering this so openly.

        So no yatch, no airplane and no exuberant lifestyle.


  • Stanislaw Komorowski

    And the desire to extend your life and the lives of your loved ones to the extent possible? How about getting seriously involved in stem cell / dna manipulation / head transplant research etc.

  • Sounds like no career could be better than what you have, so why would you choose another career? However, reading your blog all these years, you can see that your work pace is slowing. It also seems that some of the overhead of being a VC weighs on you more now and annoys you more.

    So, while I agree that you’re unlikely to find “another career”, I do wonder if you’ll ever tire of the grind of being a VC and stop? You’ve done a good job defraying it by having a month off the grid, your quarterly time off, video conference, etc. At some point it seems like that will catch up to you and there’s no more optimization available, no?

    • Time will catch up with me eventually and I’ll be dead. So I’m not worried about the endless optimization.

      I’m curious what is causing you to think my work pace is slowing. I’m not asserting that it is – or isn’t – just curious about what is driving that impression.

      • I guess I just wonder when or if you’ll eventually optimize VC out of your life before you die. I’m sure you’ll never be fully out, but you could be out of the day to day. Maybe I’m wrong and the negatives of VC will never outweigh the positives and you’ll be in a board meeting as you die.

        My impressions come almost exclusively from reading your blog posts all these years. You’ve shared many times ways that you’ve talked about slowing your rhythm (less travel, more time off the grid, etc).

        • I definitely don’t expect to be doing VC investment the day I die, unless I die in the near term.