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

Last Saturday I attended Podcamp Boston 3, a social media conference held at Harvard Medical School’s plush Joseph Martin Conference Center. Podcamp is hard to describe because it’s more like a Web 2.0 meetup or flash mob than like a real conference. The attendees themselves make up the agenda and lead the sessions, the audience is encouraged to drift in and out of the meeting rooms at will, and impromptu gatherings are always forming in the hallways. Most of the sessions were led by podcasters and focused on how to make better audio or video podcasts, but even that wasn’t a hard-and-fast theme—there were also sessions about politics, the arts, Web design, and marketing.

My favorite session was led by Stever Robbins, also known as the Get it Done Guy from the Quick and Dirty Tips network. If you’re not familiar with Quick and Dirty Tips, it’s a delightful online advice network founded and headlined by Mignon Fogarty (a.k.a. Grammar Girl) and owned by New York’s Holtzbrinck Publishers. Robbins, a Cambridge, MA-based executive coach and motivational speaker, produces a weekly podcast for the network called the Get It Done Guy’s Quick and Dirty Tips to Work Less and Do More; if you check it out, you’ll enjoy Robbins’ six-minute compendiums of sage, original advice on topics like delegating, coping with e-mail overload, having more productive meetings, and dealing with your boss.

Robbins’ session at Podcamp, called “Grab, Hold, and Grow a Loyal Audience,” wasn’t technical at all. Rather, Robbins walked his rapt listeners through the best ways to keep podcast listeners (and any audience, really) coming back for more. Among his suggestions: put emotion into your voice, use stories about people, ask questions that listeners can relate to their own lives, and don’t be afraid to use gossip and humor.

What fascinated most me was how Robbins did all of these things in his own presentation. And how—unlike some people in the life-coach industry—he was able to pull off this maneuver while still coming across as genuine. I admired his communications skills, and I was also interested in how he’d become a podcaster, so after his session I introduced myself and asked whether I could interview him sometime for Xconomy. “How about right now?” he answered.

That was when I learned about the boyish-looking, 40-something Robbins’ real background as an MIT computer-science grad, a Harvard MBA, and a veteran of nine Boston-area software startups, including FTP Software, Building Blocks Interactive, Zefer Corp., HEAR Music, Userware International, and Intuit, where he co-led the development of the Quicken Visa card.

These days Robbins works mainly with entrepreneurs at high-growth startups, helping them to overcome business or personal obstacles, but he’s also experiencing growing success with his Get It Done Guy podcast, which spent six weeks atop the iTunes business category and recently had its one millionth download—and which he’s now turning into a book, due out in 2009. In our interview, Robbins recounted how he made the shift from entrepreneurship to coaching and podcasting, and offered some intriguing thoughts about the factors that keep many talented, hard-working entrepreneurs from achieving happiness in spite of all their accomplishments. He also shared some opinions about the relationship between technology, productivity, and gadgets like the iPhone—and had some surprisingly harsh words for the venture capital community, whose interests, he believes, are “fundamentally misaligned” with those of most startup entrepreneurs. Here’s an edited transcript.

Xconomy: How do you describe yourself?

Stever Robbins: I am someone who helps people find happiness in the 21st-century world.

X: What keeps people from being happy in the 21st-century world?

SR: Information overload, and a fundamental confusion between progress and quality of life. We define progress as technological progress. We do not define progress as reaching our goals or being happy and having meaningful, satisfied lives. First of all, most people are unclear on the distinction. Second, we raise people with an utterly unrealistic set of expectations of how the world works. And third, we spend about a trillion dollars a year on an activity designed make people feel bad about their lives—and we call that trillion-dollar expenditure “marketing.” The whole message of any marketing campaign is that your life is not complete without our product. I’ve you’ve been bombarded with 20,000 ad impressions, you’ve been bombarded 20,000 times with the message that you’re not adequate. And we don’t bombard people at all with the message “This is what makes a satisfying life” or “You already have it within your grasp to have a satisfying life.”

X: You’re a technology guy and a business guy by background. How did you make the move from serial entrepreneurship into executive coaching?

SR: What happened was I hit middle age and I suddenly realized I didn’t feel like a success. I called up my friends and said “Do you feel like a success?” and they said “Sure–I have a big house, a big car, a beautiful wife.” I would say, “That’s really nice, but do you find your life to be fun? Do you get up excited in the morning?” And most people said, “No, most of the time I just want to kill myself.” I just noticed most people are not very happy, even when they are achieving the things they are supposed to want to achieve.

By pure coincidence one day I was talking with a friend. He was an entrepreneur, and I was an investor in his company, and I was advising him. And he said “Do you realize I would pay you $3,000 for 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 you care too much about people.” That’s a typical VC attitude. They are a bunch of people who are there to get rich, and once they are rich, they don’t care anymore.

That’s not the way to build an enduring company. If you care about sticking around and helping people, you have to spend as much time on the culture of your company as on the other stuff. In my experience, in a startup, it’s way too easy to get sucked into caring about the minutiae of the product and not spending nearly as much time on the culture and the systems.

To me, there are three prongs to a startup—systems, people, and money. Most CEOs I have seen don’t balance their time between these. They’re usually way too into building the right system and they ignore the people and the money. Or they’re too into the money and they ignore the systems and the people. What people don’t get is that money is a commodity. Every business ever started has found investment funds. Yet this is where a lot of CEOs spend most of their time.

X: You’re pretty down on venture capitalists. Isn’t there such a thing as a caring VC?

SR: As a VC you can’t be caring. Here’s the thing most entrepreneurs don’t understand. VCs have a fiduciary responsibility to their investors, not to their portfolio companies. You cannot let sentimentality get in the way of that; that is not the agreement you made with your investors. Which means that if you have two investments and one is going to produce a 10x return and the other is going to produce a 20x return, you may liquidate the successful 10x company in order to fund the 20x company. As the 10x CEO, you are going to be really unthrilled about that. But you know what? You should have read the fine print. This is why I recommend that people not take venture capital unless there is an extremely compelling reason—because the incentives of the VCs and the incentives of most companies are fundamentally misaligned.

X: Earlier you said that we confuse progress with happiness. But I see that the little cartoon guy on your business card is holding an iPhone, and I have an iPhone. And I have to say that gadgets like that make me inordinately happy. Is that wrong?

SR: Good heavens, no. However, the way you put it was perfect: gadgets make you happy. Bless you. Let me buy you a few more! But do not say the following: “Gadgets make me more productive.” People buy gadgets because they erroneously believe that they will make them more productive. Not true. Depending on how you use them, they may make you more productive. But they probably won’t.

The reason is that if you do find a gadget that makes you more productive in a particular dimension, then either you or the people around you will ramp up their expectations in that dimension, so that you are still spending the same amount of time, but you are more productive, quote unquote. You are not experiencing any added free time. That’s one of the reasons I don’t believe in any technological solution to productivity.

At the end of the day the problem is not technological, it’s social and economic. And this is an American thing; it’s not universal. We insist as a culture on translating productivity gains into shareholder profits rather than into a higher quality of life for workers. As long as we play that game, none of our productivity-saving devices will help us as individuals.

X: What about tools like David Allen’s “Getting Things Done” method—a brand that you echo in the name of your podcast, the Get It Done Guy. Isn’t that helping people be more productive?

SR: I think it’s helping people clear their minds. I adopted it several years ago and found it to be incredibly helpful. It’s a piece of the happiness puzzle, but it’s far from being the whole puzzle. I interviewed David Allen for my podcast—it hasn’t aired yet—and I think he’s a great guy. He’s very clear that the organizational piece is the means to an end, the end being happiness and a good life. But it’s possible to be very organized and very miserable.

In Western culture, we believe that doing is the point of life. In Eastern cultures, it’s about being. If you believe that doing is the point of life, no amount of David Allen will help you become happy, because there is always more to do. That is the nature of life. You wake up tomorrow and the crops need to be harvested. But if you believe that happiness is in being, then you can get there, because we are always being.

And adopting Getting Things Done is not the way to realize that. Let me go so far as to say that it’s probably easier to be happy by coming to peace with not being able to get things done than it is to attempt to be a Getting Things Done person.

X: Going back to that question of happiness—I’ve seen research suggesting that people who deceive themselves about how successful or talented or liked they are, are actually happier than people who are more realistic about their abilities. What does that say to you?

SR: That relates back to the literature on learned optimism. I am a pessimist by nature who tries very hard to stay optimistic so I will get the benefits of optimism combined with the realism of pessimism. I believe the human race is going to go extinct within my lifetime because of global climate catastrophe. And I’m having a good time between now and then. And if you really think that getting through your e-mail inbox is important, just give that some thought.

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

Trending on Xconomy

By posting a comment, you agree to our terms and conditions.

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…