Archive: Business

  • Tribe Vibes: The Secret to Avoiding Micromanagement

    November 24, 2021

    Micromanagement is a killer. All founders have trouble getting out of the weeds.

  • 1999–2019: Twenty Years of My Lessons as CEO

    December 22, 2019

    Entrepreneurship is a journey, and it seems like it will be a lifelong one for me. The ride is filled with adventure, obstacles, and destinations that surprise. In the spring of this year, I decided to return to one of my passions: writing about my learnings as a CEO. This year marks the end of

  • 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

  • How to Raise Money When You’re an Underdog

    December 1, 2019

    Trust me, sometimes, getting a NO from a VC — no matter how peculiarly it is delivered — could be the best thing that ever happens to you.

  • 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

  • Tribe Vibes: Who is In Charge of What?

    November 24, 2019

    I have noticed a pattern in the 20 years I have been an entrepreneur, advisor, and CEO. Every time there is something wrong with a company, there is a recurring problem. Either someone is not doing their job, or they didn’t know it was their job. It’s more common than you think. A problem with

  • 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

  • Why Women Rule, At Least They Should

    November 10, 2019

    In 1971, a young mother of three boarded a small boat to make a journey from her home country, Haiti. She hoped to find her husband, who had fled Haiti’s dictatorship nine years earlier. She reunited with him in a flourishing community of Haitian immigrants in The Bahamas, where he had found safety and work.

  • Modern Risks, Modern Measures: A Chat with Carey Anne Nadeau, Part II

    October 27, 2019

    The underrepresentation of women in tech is, quite frankly, abysmal. 13% of the global Fortune 500 are women, according to Tammy Moskites, Managing Director at Accenture. “That’s not just CISOs. That’s CISOs, CIOs, and senior executives such as a VP in the technology arena. It’s still a very, very small amount that equates to about

  • How Random Walks Can Make You A Better Manager

    October 20, 2019

    The next time you are in your office, wondering what you should do. Take a random walk through your company. You’ll be surprised by what you find.

  • What I Learned From My First Exit: A Chat with Ron Fisher

    October 13, 2019

    People think their next amazing business idea is going to be in their head, when you’re sitting in your room by yourself with a journal, totally detached from what you’re working on.

  • Modern Risks, Modern Measures: A Chat with Carey Anne Nadeau

    September 22, 2019

    Around the time this article is published, a whopping 7000 people will descend on Las Vegas to discuss the future of insurance. For three solid days, people from all walks of life who have joined the insurtech wave will introduce themselves, network, and fight to get heard in a sea of innovation. It’s all happening

  • How One New System Can Make You a Superhuman CEO: A Chat with Bouzha Cookman

    September 15, 2019

    About 8-years ago, I boarded a flight from JFK to make my way to an island about 30 miles south of Cape Cod, Massachusetts. It was a welcome break. I was attending a small, annual, invitation-only gathering of the northeast’s forward-thinking entrepreneurs, venture capitalists, executives, and researchers. The location and name — Nantucket Conference — were fitting. The island

  • How Ketchup Protected my Product Market Fit

    August 23, 2019

    Once, when meeting with the CEO of a new customer, I pulled out a bottle of ketchup and set it on the table. It was one of these … Once, when meeting with the CEO of a new customer, I pulled out a bottle of ketchup and set it on the table. (Image: istockphoto) It was

  • Laser Focus and Seven Nuggets of Advice for First-time Founders and CEOs

    May 1, 2019

    “Four votes for John,” said one of my four co-founders. It was 1997, and we were deciding who among us would be the titular head of our first venture. It was a simple ceremony, no cryptic puffs of smoke through an old chimney. While I was happy to have won the election — I wanted to win — I