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Being CEO

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    • 5 Leadership Questions from a Friend

      5 Leadership Questions from a Friend

      February 29, 2020

      Being CEO, Interviews, Leadership, Letters, Life Lessons

      It’s counter-intuitive, but your title may make you manager, but your team makes you a leader.

    • 5 Reasons Why CEOs Make Bad Decisions and How to Avoid Them

      5 Reasons Why CEOs Make Bad Decisions and How to Avoid Them

      February 23, 2020

      Being CEO, Bookshelf, Leadership, Management, Mental Models

      It’s time to fire my gut.As a CEO, I have a bias for action and often make decisions with my gut.

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

      1999–2019: Twenty Years of My Lessons as CEO

      December 22, 2019

      Being CEO

      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?

      How Many Jobs Does a CEO Have?

      December 18, 2019

      Being CEO

      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

      6 Habits that Help Me Focus on What to Do Right

      December 15, 2019

      Being CEO

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

    • What’s Your (CEO) Superpower?

      What’s Your (CEO) Superpower?

      December 4, 2019

      Being CEO, Letters

      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

    • Tribe Vibes: Who is In Charge of What?

      Tribe Vibes: Who is In Charge of What?

      November 24, 2019

      Being CEO, Culture, Management, Tribe Vibes

      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

      The weFailure

      November 20, 2019

      Being CEO, Culture, Letters, Management

      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

      Why Women Rule, At Least They Should

      November 10, 2019

      Being CEO, Diversity, Leadership, Women

      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

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

      November 3, 2019

      Being CEO

      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

    • How Random Walks Can Make You A Better Manager

      How Random Walks Can Make You A Better Manager

      October 20, 2019

      Being CEO, Leadership, Management

      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

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

      October 13, 2019

      Being CEO, Founding, Fundraising, Interviews

      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.

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

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

      October 6, 2019

      Antifragile, Being CEO, Culture, Leadership, Life Lessons, Management, Tribe Vibes

      The body is strong, the mind is weak.

    • 6 Ways I Embrace Impostor Syndrome

      6 Ways I Embrace Impostor Syndrome

      September 29, 2019

      Being CEO, Featured, Leadership, Life Lessons

      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

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

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

      September 15, 2019

      Being CEO, Coaching, Insurtech, Leadership

      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

    • What is Entrepreneurship? A Chat with Dip Patel

      What is Entrepreneurship? A Chat with Dip Patel

      September 8, 2019

      Being CEO, Founding, Interviews, Leadership, Life Lessons

        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

      Antifragile: Building A Company That Goes Beyond Resilience

      September 1, 2019

      Antifragile, Being CEO, Culture, Life Lessons, Management, Tribe Vibes

      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.

    • How Ketchup Protected my Product Market Fit

      How Ketchup Protected my Product Market Fit

      August 23, 2019

      Being CEO, Insurtech, Leadership, Management, Product

      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

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