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 … 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…