• 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: Why All Great Leaders Find Time for Solitude (with John Belizaire)

    June 20, 2020

    In this episode, join me as I explain how (and why) you should make solitude a core-component in your leadership strategy. Learn why effective leadership depends on solitude.

  • How to be an Antiracist CEO

    June 14, 2020

    The death of George Floyd and its aftermath is a stark reminder of a virus, deadlier than COVID, that has been here for 400 years. 

  • How to be a Wartime CEO

    April 17, 2020

    Coronavirus is a new opportunity to rise as a CEO.

  • 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.

  • 8 Books I Couldn’t Put Down in 2019

    February 17, 2020

    Its like weightlifting for the brain. Last year, I decided to focus on leaders. 

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

    October 6, 2019

    The body is strong, the mind is weak.

  • 6 Ways I Embrace Impostor Syndrome

    September 29, 2019

    It starts deep in the pit of my stomach. It’s hard to describe. It’s like a cross between butterflies and sharp fluttering stomach pain. Sometimes, it manifests itself as a pain on the left side of my neck. It feels like a burning, humming sound. The buzz you might hear at a power substation full

  • What is Entrepreneurship? A Chat with Dip Patel

    September 8, 2019

      The truth is when you have the combination of these two (thinking and doing) inside you — whether you believe it or not — you are an entrepreneur. (Photo by christian koch on Unsplash) What do home climate control and missile defense systems have in common? A lot. This is what my friend Dip Patel discovered in circa

  • 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.

  • 5 (New) Learnings from a Recovering #Insurtech CEO

    June 9, 2019

    It’s been two years since I have been at the helm of a fast-growing #insurtech startup. I have since moved on to new adventures. But, I have kept up with the pulse of the industry by serving as an advisor and coach to newbie CEOs who are among a class of innovators. In my role,

  • Finding Solitude in Leadership: A 4 Step Recipe

    June 2, 2019

    “Crunch, crunch, crunch,” was the sound my gait made as I marched along a distant barren landscape. Here, there were no demanding customers, no competition putting pressure on me. There were no employees anxiously seeking consensus and no investors asking endless questions about our sales forecast. Absent were the industry publications offering views of the

  • Pain is Where the Learning Happens

    April 5, 2019

    “Resisting pain only increases its intensity.” — Chogyam Trungpa I am 47 years old and I have made a lot of mistakes in my life — both professional and personal ones. I hope I make many more. It’s true. I have hired the wrong people on my management team. I have taken too long to fire people after I realized

  • Bad Blood and My Seven 5-star Books from 2018

    March 3, 2019

    I often tell the new CEOs I advise to never fall in love with your product, keep your ego in check, and love your customers. The story of Theranos, portrayed in the book Bad Blood, is what happens when this advice is completely ignored. It is a five-star page-turner that is a window into human

  • 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.

  • A Recipe for Rightsizing Your Team When Disaster Strikes

    August 28, 2017

    The role of a CEO is fraught with tough decisions. Firing people is not easy, but it is part of the job.

  • How a Little Pepto Bismol and a Serious Talk Can Save Your Company.

    July 21, 2017

    It was the beginning of summer. I did not particularly enjoy riding the subway this time of year. It was blisteringly hot. However, it was the quickest way to get around the city. Traffic had become a year-round nightmare in New York City. “Hey John,” he said. “Are you ready for this?” “I better be,