November 29, 2023

Tony Hsieh: Lessons and stories from my friend, mentor & investor.

This is a conversation I had with Tony Hsieh and also my tribute to him.

Tony Hsieh delivered happiness as his main gig but he also delivered dreams as a side hustle. Moonlighter. He was first a friend, then mentor, then client and then my investor. He continues to be one of my greatest teachers.

Tony believed in me before I learned to believe in myself. He never gave me the answers I was seeking (damn it!) but he always asked the questions I needed and craved. Usually this was during a walking meeting downtown or over his favorite digestif, the famous fernet.

One question and conversation at a time, Tony taught me how to mentor myself. He’s a constant voice in my head and grin in my heart. Yeah, that famous grin on the verge of a quirky smirk. You know the one.

The thing is, I’m not special. Tony goes big. He did this at scale with many happy-go-lucky beneficiary-mentees. Many of which have become very good friends of mine over time. He was an open-source style kind of guy. Sharing was his thing.

Tony collected friends and experiences, not things. He’s the shoe dude who could care less about shoes, it was all about the delivery.

I have countless magical memories. From the bizarre stories, the kind where you’re saying to yourself “I can’t make this shit up” to the lifelong, formative lessons. He was the most innovative, visionary, helluva good time guide I’ve ever witnessed. A guide that led me down many black diamond mountains of life and business. The difficult stuff was his jam. He was an expert and made the moguls feel like the bunny slope.

A few of my favorite lessons and quotes from Tony:

  • Most people wait too long to hire and fire. (on entrepreneurship)
  • Resourcefulness > Resources.
  • “Most entrepreneurs don’t fail due to a lack of opportunities, they fail because of too many.” (Aka. Focus.)
  • Airstream livin’ isn’t for everyone. I lasted exactly two nights. Too loud and up too late for this original trailer park gal.
  • “Most people misdiagnose what makes them happy.”
  • “If you’re going to study something, it might as well be happiness.”
  • “Why? Why? Why?” (Grin, smirk. Repeat.) — Tony’s formula for Delivering Lessons.
  • “If I lost it all, I’d just build it again.”

Our friend, Tony Hsieh. You will be missed, remembered and celebrated forever.


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