Antifragile: Building A Company That Goes Beyond Resilience
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
How Ketchup Protected my Product Market Fit
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
Should Your Startup Be Hiring Specialists or Generalists?
Managers love to reward hyper-specialization. But is it better to hire for general problem-solving abilities?
5 Jobs to Master as CEO
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
9 Things CEOs Can Learn From a Trip to Disney World
The first time I went to Disney World if my memory serves me, was the summer of my freshman year in college. It was 1990, and it was part of an annual family pilgrimage to Florida to visit our extended
Empathy: What One Day of Ramadan Fasting can Teach
“…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
5 (New) Learnings from a Recovering #Insurtech CEO
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
Finding Solitude in Leadership: A 4 Step Recipe
“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
Great Books To Help Elevate Your Recruiting Game
Any successful CEO will tell you there are three keys to an A-level company: The right strategy in the right market, at the right time; An A-player team that fits with their culture; and financial discipline. Hand-picking the right people
Pain is Where the Learning Happens
“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
One Superpower I Use Everyday as a CEO
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 important. I developed and honed my “superpowers” as a CEO