• Pain, Joy, and Learning in 2020

    December 31, 2020

    As I reflect on 2020, I see a real lesson in resilience.  2020 was full of pain, joy, and learning. 

  • The Secret to Being a Great CEO

    November 29, 2020

    I often ask myself if my success has been about sheer willpower.  

  • 5 Leadership Questions from a Friend

    February 29, 2020

    It’s counter-intuitive, but your title may make you manager, but your team makes you a leader.

  • CEO Spotlight

    December 25, 2019

    “Your most unhappy customers are your greatest source of learning.” — Bill Gates

  • How to Castrate a Bull

    December 11, 2019

    When developing a B2B technology company, you have two choices. You can sell to small and medium-sized businesses (aka SMBs), or you can sell to large enterprises. There is a stark difference between how you sell to one group versus the other. Large enterprises are demanding, are process-heavy, and unusually large organizations. So, solving problems

  • What’s Your (CEO) Superpower?

    December 4, 2019

    At dinner one evening, a close friend and entrepreneur asked me, “what CEO skills are you using the most now in your new role?” (image:istockphoto) ARR, LTV, GTM, churn, positioning, competition, customer satisfaction, valuation. Over the past 18 years, I have been the founder and CEO of two companies where these metrics (and more) were

  • The Power of Empathy

    November 27, 2019

    “Empathy is not just an awareness of what others are experiencing; it’s aware of, being sensitive to, and caring about how one’s own behavior affects others.” — Danny Meyers Danny Meyers is one of my favorite entrepreneurs. He is a successful New York City restauranteur and the CEO of Union Square Hospitality Group. He is behind successful restaurants

  • The weFailure

    November 20, 2019

    Twenty years ago, on 11/19/99, I sold my first startup. It was a technology company selling something called “Java Beans.” My four co-founders and I had a life-changing experience when a company called BEA Systems acquired our company for over $100M. We were excited not just for our own lives, but the way it would

  • Becoming Obama: A Memoir

    May 23, 2019

    I believe that the life story of everyone on Earth is not just a linear fairy tale with a straightforward beginning and end. Instead, it is a mosaic of mini-stories that come together to create a masterpiece like the work of Antoni Gaudi. When I opened my copy of Michelle Obama’s book Becoming, I half