Three Things I Learned In Saas, Sports, Tech & Live Events

Playing not to lose is one of the most common mistakes in starting a business (and, recently, in Euro 2020).

Three ways playing to not lose crushes our business (and career) from our own mistakes

1. Hiring. We take the safe hires. The candidates from the big names who'd "done it before" over the most talented bc they're the most impressive to banks and investors.

2. Customers. When playing not to lose, we let customers dictate terms where we all lose. Churn is expensive. Customers failing to achieve goals with our products is worse than losing the sale. "We fix $5 haircuts."

3. Careers. We give up too much upside to guarantee unneeded downside protection. Nobody gets rich on salary, but it's the most over-negotiated point. It costs us money and happens way too often. If not betting on oneself, why should anyone else?