• 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.

  • 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.

  • 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.

  • Cancel All Your Meetings, Except These

    December 13, 2020

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

  • 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: 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. 

  • Easy is Boring: My 2020 Mantra

    March 8, 2020

    Keeping teams motivated is really hard. But, if you are only focused on what amazing thing you can personally do, you are missing the point. 

  • 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

  • Antifragile: Building A Company That Goes Beyond Resilience, Part 2

    October 6, 2019

    The body is strong, the mind is weak.

  • Antifragile: Building A Company That Goes Beyond Resilience

    September 1, 2019

    Slipping on a banana and breaking your hip is fragile. Getting hit by a truck then getting up to walk to your hair appointment is resilient. But, getting one of your arms cut off then growing a new one the next day is beyond resilient — it’s antifragile. Sh*t happens in startups. (Amen, right?) I can relate.

  • 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

  • Why CEOs Are Better Than Chimpanzees

    March 21, 2019

    As a CEO, one of your jobs — it’s maybe the most important — is to give your fellow sapiens what they need most, something to believe in.

  • It is all about DNA: How to Hire Like Your Life Depended On It.

    October 1, 2017

    Companies are a unique combination of people that make them legendary; or not.