Some of the best leadership thinking comes from people who never set out to be leaders.
It comes up throughout You Mon Tsang’s appearance on Your Leadership Podcast, hosted by Mike Madison, law and leadership professor at the University of Pittsburgh, and Kathy Edersheim, founder and president of Impactrics, a global consulting practice that focuses on nonprofit governance, and the author of Connect, Engage, Thrive: The Art of Alumni Relations. The episode is part of the podcast’s third season, which explores the difference between founding and sustaining, and the pressure technology is placing on how leaders work.
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Listen to the full episode.
You Mon Tsang , founder and CEO of ChurnZero, now on his fifth startup, opens with an admission about what turned him from employee to entrepreneur:
“I was always a great employee until I was not a great employee. I did good work, but I had my own ideas, and starting a company felt like an interesting way to be a great employee — do the good work and not have a boss.”
He describes a version of himself shaped by immigrant parents and a narrow worldview, the kind that defaults to hard work because hard work was the only variable. What broke the pattern was stubbornness.
“I would resist what I would think would be a poor decision. I would do things and try to get them done without permission that I thought were right. That’s sort of what got me to be a bad employee.”
He calls his management style “lead dog” — not the musher directing from the back, but the dog pulling hardest at the front.
” That’s all I know how to be, and it breaks in certain situations. If we’re a thousand employees and I still act like a lead dog, that may not be the right way to go.”
The conversation also covers how he’s navigated AI uncertainty at ChurnZero, what success actually means for the people working with him, and why after five startups he still can’t imagine doing anything else.
