• The Layer Cake: 3 Secret Ingredients for Leadership

    October 23, 2022

    The best teams are built on trust, conflict, and commitment in that order.

  • Why How Smart You Are Has Nothing To Do With How Successful You’ll Be As a CEO

    September 26, 2022

    The journey as CEO is a long one.   You won’t be able to rely purely on your god-given raw intelligence for the whole trip.

  • Working With John: My CEO User Manual and Why You Need One

    July 24, 2022

    I am here to help you achieve your goals. I am your servant.

  • Lateral Thinking: The Best Tool for Solving Impossible Problems

    April 16, 2022

    There is no way to escape impossible problems on the entrepreneurial journey. Often, the solution lies in Lateral Thinking, changing our perception of the problem.

  • First Principles, Part 4: Caring Counts

    February 15, 2022

    People don’t care what you know until they know that you care.

  • Tribe Vibes: The Secret to Avoiding Micromanagement

    November 24, 2021

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

  • Tribe Vibes: The Lily Pad Theory

    September 4, 2021

    Communication is at the root of all business strengths—and weaknesses.

  • First Principles, Part 3: The Secret to Being Customer Centric

    March 7, 2021

    There is no better selling weapon in the whole world than a happy customer talking to a prospect.

  • First Principles, Part 1: Seek Advice Early and Often

    February 19, 2021

    The biggest thing I learned in my time as CEO was how much I had to learn.

  • One Superpower I Use Every Day as a CEO

    February 18, 2021

    ARR, LTV, GTM, churn, positioning, competition, customer satisfaction, valuation. Over the past twenty years, I have been the founder and CEO of two companies where these metrics (and more) were important. I developed and honed my “superpowers” as a CEO to ensure each of these measures was going in the right direction. As a result,

  • Why the Best CEOs Are Curious: A Chat with Corey Thomas

    January 24, 2021

    A leader’s job is to create the environment and the context where people can actually do the most, accomplish the most, and teams can be the most impactful.

  • Leadership in Crisis: What We Can Learn from Governor Andrew Cuomo

    January 10, 2021

    We never plan for a crisis.  When we are in the midst of one, it feels like an endless mountain to climb.  

  • Cancel All Your Meetings, Except These

    December 13, 2020

    It’s not about the meetings; it’s about the right meetings.

  • Why We Sleep and My 2020 Summer Reading

    November 11, 2020

    Sleep is the single most effective thing we can do to reset our brain and body health each day.

  • Tribe Vibes: 7 Secrets to Creating Magnetic Culture

    August 30, 2020

    The culture of a company can easily make or break it. Focus on making yours magnetic. 

  • #CEO Podcast: You’re a CEO, But Don’t Think You Need Sales Skills Huh? (with Jim Hemmer)

    August 27, 2020

    Sales is an integral part of any business, but rarely associated with the CEO’s role.

  • Mental Models: 5 Books That Will Help You Think like Charlie Munger

    July 12, 2020

    As CEOs, if we train our minds to see the bigger picture, or consider all sides of the problem before making a decision, we can become better leaders. By using knowledge and insights from many disciplines, we have a chance.

  • #CEO Podcast: Culture Should be Curious-Are You Inspiring Curiosity in Your Team? (with Corey Thomas)

    July 11, 2020

    Corey Thomas isn’t in the role he thought he’d be as Chairman and CEO of Rapid7, but 7 years, a ton of successes, a failure or 3 and an impressive and enviable culture, show that sometimes our paths lead us exactly where we belong.