Stever Robbins on How to Be A Happy Entrepreneur—One Tip, Never Trust a VC

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the conversation we just had?” And I said, “Do you realize I would bill you $3,000 for the conversation we just had?” And he said, “Send me the bill,” and my coaching career was started.

As I was doing this executive coaching, I started to notice that the business issues were always the minor issues. The things that were holding companies back were first and foremost, all the stuff the executives believed about what was important, and secondly, that they didn’t know how to make things work for them so that they could be happy. And it was really clear that the things they were doing were not going to get them there.

X: How did you learn what makes people happy?

SR: I went out and read every book on psychology I could find. I tried everything—that part is very important—and I discovered 99 percent of it didn’t work. I looked at my friends who had been in therapy and discovered 99 percent of them had not gotten help. I tried everything I could get my hands on, and the main things I found useful were from social psychology—the optimism research, such as Martin Seligman’s work on learned optimism.

But people don’t actually hire me saying “Help me be happy,” and I’m not sure I would take that kind of engagement. People say “Help me grow my company.” I ask, “What does growth mean to you?” and “What would be a successful outcome?” and then I try to ensure that the happy outcome includes personal happiness as well as business success.

X: Okay, and how did that lead to the podcasting gig?

SR: I had–and still have—a podcast called Business Explained where I try to take various business concepts and make them more succinct. It never got much listenership, and I think part of that I was it was very businesslike. I thought the Get it Done Guy would be a creative outlet where I could just go wild and not have to worry about people saying “He’s so unprofessional.” And it turns out that the unprofessional me is far more interesting and popular than the professional me.

Personal productivity was one of the things I would do with my coaching clients. When I pitched Grammar Girl on my show, I gave her several possible areas, and the personal productivity was the one that I thought had more opportunities as a topic than business strategy or leadership. So the mission of the podcast is to help people be happier by getting more done more quickly and having more time to do what makes them happy and gives meaning to the rest of their lives. That’s my whole motivation. I don’t talk about happiness. It’s just that when I’m trying to decide what things to address, I keep choosing things that I know will also produce happiness.

For instance, I’m working on an episode right now about gratitude—calling people up and thanking them for nice things they’ve done. That’s something we don’t normally do. I’m presenting this as a networking exercise. But lots of research shows that the more you indulge in gratefulness, the happier you will be. That is how I run the podcast—I give you practical concrete tips designed to produce a life for you that will be not only successful but also happy. I am an engineer and an MBA and I am all about producing concrete results—not about being touchy-feely.

X: In your experience, what are some of the most common things that keep technology entrepreneurs from being happy?

SR: I’ve found that a lot of them derive way too much of their satisfaction and self-esteem from accomplishing things. That manifests in many different ways. If they succeed at accomplishing things, they can turn into arrogant jerks. If they don’t, they can take it personally and beat themselves up. They can feel highly insecure to the point that the overcompensate by projecting a confidence and slickness that makes people cringe when they meet them. Everyone except them can pick up on it.

I find that a lot of these people, especially if they are MBAs, have an extreme lack of appreciation for the people in their business. A lot of them believe that they view people as irreplaceable gems. But if you were to look at their behavior, they treat people like commodities and fail to get the best out of them. I’ve seen this over and over again.

And if you’re backed by a bunch of VCs, watch out. The VCs care about nothing except the return on their investment, so they are not going notice your blind spot, because as a class, VCs have this same blind spot. My friend who was a VC told me once “You don’t have what it takes to be a VC,” and I said, “Why?” and he said, “Because … Next Page »

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Wade Roush is a freelance science and technology journalist and the producer and host of the podcast Soonish. Follow @soonishpodcast

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6 responses to “Stever Robbins on How to Be A Happy Entrepreneur—One Tip, Never Trust a VC”

  1. Beckett Gilchrist says:


    Thanks for this fascinating interview.

    The paradigm of now is balance, evening in marketing and business. I appreciated reading Mr. Robbins take on that correlation.


  2. JJ says:

    Insightful(l). Thanks Stever! ;)

  3. Carmelo Lisciotto says:

    Interesting interview, I enjoyed reading…