Archive: Leadership

  • CEO Spotlight

    December 25, 2019

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

  • 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 Many Jobs Does a CEO Have?

    December 18, 2019

    Satya Nadella, CEO of Microsoft, certainly makes the list of most admired leaders right now. Under his leadership, Microsoft has gone beyond Bill Gates’ wildest expectations. The firm that launched the PC software industry surpassed $1 Trillion in market cap this year, making it one of the world’s most valuable companies. He’s led the company

  • 6 Habits that Help Me Focus on What to Do Right

    December 15, 2019

    We are what we repeatedly do. Excellence, therefore, is not an act but a habit.

  • 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

  • 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.

  • Hello Mr. President: How One Event Changed My Perspective as CEO

    November 3, 2019

    A few weeks ago, I got an email from an old friend. She was part of the marketing organization in the early days of my last company — a fantastic woman — she was looking for an update on what I was doing and agreed to write a recommendation for me as a CEO. She reminded me of a

  • 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.

  • 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

  • Should Your Startup Be Hiring Specialists or Generalists?

    August 4, 2019

    Managers love to reward hyper-specialization. But is it better to hire for general problem-solving abilities?

  • 5 Jobs to Master as CEO

    July 29, 2019

    It happens rather quickly. Your new investors sign a shareholder’s agreement, a subscription agreement, and a corporate charter. Usually, you create a new class of (preferred) shares. You receive a notification from your bank that the wires from investors have cleared. Your lawyers file the company’s new corporate charter, and a new board of directors

  • Tribe Vibes: How to Grow Empathy on Your Team

    July 7, 2019

    Human beings are tribal by nature. Our need to belong far outweighs many things in life. So, we naturally split into tribes.

  • Empathy: What One Day of Ramadan Fasting can Teach

    June 12, 2019

    “…It’s both physical and spiritual. The essence is to try and feel what the poor feel without food and try to be a better person by reflecting on our actions and thoughts. Try to be nice to each other, avoid bad/angry thoughts, etc.” — B. Drissi (personal friend) As I write this article, we are 19 days