The Root Cause of My Most Expensive Mistakes
Fear = negative expected value. Love is the ultimate competitive advantage.
Above all else, one truth emerged from my journey as a founder and CEO. My decisions driven by love created value, and those driven by fear destroyed value. Fear may have improved a local maximum, but ultimately hurt the global maximum.
Love? You mean that messy, mushy emotion that we can’t objectively measure? Yes. At first glance, love may seem antithetical to business. How do rainbows and peace signs win in a cutthroat corporate world? I challenge this framing of love. Love can be fierce and tough. And sometimes, it must be. Fear seduces us into short-term comfort and distorts everything. Love endures short-term discomfort in service of long-term flourishing.
I often confused fear with strength and responsibility. I now see how many of my well-meaning decisions negatively impacted our business. In my weakest moments, I’d default to the easy choice, not the right one. For example, I’d hire an incredible leader who’d deliver amazing outcomes in their first few years. But as our business scaled into a different stage with different needs, they’d struggle to adapt. Despite clear feedback, it was no longer working. It was time to part ways. (Side note: these were the most heartbreaking moments of my career). But my fear delayed the decision for months. What if they took it poorly and spoke ill of me? What if their loyal reports follow them out? What if they join a competitor? What if I can’t find the right person to fill their shoes? How will I find the time to manage their team in the interim?
If I really loved this person, I’d want them to be in an environment where they’re set up for success, working for someone who believes in them. If I really loved my team, I’d find the right leader for them, now. If I really loved everyone, including myself, I wouldn’t waste more precious time. In that moment, love demanded courage. Love demanded having the hard conversation now, despite the pain. Not acting sooner was cowardly. It also signaled low standards and a lack of accountability. My avoidance hurt my team and company, and cost us hundreds of thousands of dollars or more.
My pattern of toxic avoidance and attachment repeated itself in different forms.
I waited too long to step down as CEO. Despite struggling with severe burnout and depression for several years, I kept grinding as if everything was okay. I’d put on a cheerful mask in the morning and come home exhausted in the evenings. The bad kind of tired. I was terrified of losing what had become my primary source of identity and self-worth. My ego also led me to believe that the business would fail without me. During this period I made many suboptimal decisions. My team deserved a leader who could think clearly and give 100%.
I sometimes didn’t speak up for fear of displeasing others and/or looking stupid, especially in my boardroom. I struggled with impostor syndrome. What do I know? These successful people I admire and respect must know better. I now realize that while it’s important to keep an open mind, usually no one knows their business better and cares more than its founder(s). Some of our missteps might have been avoided had I more fiercely advocated for myself.
I focused almost exclusively on what could be improved and rarely praised others. I feared that celebration would make us complacent. One company-wide survey highlighted a common theme around lacking pride in our accomplishments. Nothing was ever good enough. One particular comment has stayed with me - “Jason walks around the office with a scowl on his face. He seems stressed or pissed off a lot.”
Fear shows up everywhere in business.
Fundraising. I’m scared to share my true vision ➡️ Investors fund a version of the company that I’m not all-in on
Hiring. I’m scared that I won’t ever find the right candidate ➡️ Settle for someone who doesn’t actually want to be here
Sales. I’m scared of asking for more money ➡️ Undersell our value
Product. I’m scared of shutting down a product that isn’t working ➡️ Keep wasting precious resources
Management. I’m scared of looking bad ➡️ Perpetuate a culture optimized for optics over learning and truth
Whether it’s changing customer needs, ruthless competition, constant rejection, layoffs, investor pressure - the reality of business is not for the faint of heart. There is some truth to Andy Grove’s famous line: “Only the paranoid survive”. Many espouse the killer instinct necessary to compete against those who would eat your lunch. The founders and CEOs I coach often ask “Will leading with love make me complacent? Will I lose my hustle?” This assumes a false tradeoff between love and hustle. The right question is “Is my hustle fueled by love or fear?”
Hustle, high standards, competitiveness, grit, ambition, etc. are not inherently good or bad. It’s about the fuel. Fear burns hot. Love burns long. Through this lens, every behavior has its healthy and unhealthy manifestation.
Both my fear and love shaped our culture and decisions. Dirty fuel can feel so good. In the moment, it feels comfortable and addictive. But eventually, the piper must be paid. Fear can win the quarter. Love wins the decade.