Here’s a conversation I had with Tony Hsieh and also my tribute to him on the Why Not Now? podcast: Available on Spotify and also on Apple Podcasts.  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.

Here are a few:

DMs to Hot Air Balloons:

I met Tony in 2009 via a DM when I asked him about the Zappos social media policy. I was working in the NBA for the Phoenix Suns and Zappos was the only company I could find that was really using social. Employees were empowered. I had never heard of the company, didn’t know how to pronounce it and definitely didn’t know how to pronounce Hsieh. Wink. Tony DM’d me back, “be real”. (No caps. He never used caps. Not important.) I thought, okay – a man of few words. I printed that puppy out and took it to the Suns leadership meeting. “See, this is the way to do it!”

A couple weeks later he DM’d and invited me to come to a talk he was giving in Phoenix. Within an hour of meeting him, we somehow ended up on a hot air balloon ride and he told me about his hobby of studying the science of happiness. We talked about the different types of happiness and the formula. Things I still think about daily a decade later.

That’s Tony. Somehow you end up in a hot air balloon talking about happiness – willy wonka style. A month later, I quit my job, started my first company and four years later, Tony became an investor with the caveat of moving our HQ to Vegas. Winky face.

Party Bus to Tour Bus

Yet prior to that in 2010, I went to Sxsw for the first time with Tony. Oh, I was in for it. He got a school bus, added bartenders and I’m pretty sure there was a stripper pole too. No strippers though, I don’t think? There was a text thread that shared where the bus was for each stop and when it was leaving. Very organized but again, no capital letters to be found in those texts. We had a blast to say the least. One night during the trip in the hotel lobby with Jenn and a few others, Tony got the idea that his book tour could be a book bus tour. He told Jenn she would lead the planning and I could help. Tilt head? Next thing you know he buys the old Dave Matthews touring bus, adds winky faces and we’re off on a tour around the US. I remember sending him a scope of work. He didn’t open the document. He said, “Just charge what you think is fair.” I’ll never forget that. I’ve borrowed it a few times since over the past decade.

Battleship Inbox

As many people know, Tony had a thing about his email inbox. From his crazy quick shortcut system that I’m pretty sure was from DOS days to Yesterbox to the shared evernote that auto-tracked his inbound and outbound activity. Somehow I was subscribed to that and I’m pretty sure it pounded “consistency compounds over time” into my head as I saw the ticker updating. Something we had in common was that our inboxes were always on our minds, Wille Nelson style. On a random co-working session occasion, we’d have races to ‘inbox zero’. We would set up our computers, facing-off like battleship, and “race” to see who could answer more emails in an hour. He was always faster but he always had more coming inbound than I did too. So we’d waste another hour debating about the rules and who really won while his inbox filled up once again in the background. He always answered though. And, he was always on time to meetings because he respected everyone’s time and he valued reciprocation.

Tony taught me that resourcefulness is more important than resources. You didn’t have to have a lot of money to be an innovative entrepreneur but you did need to be resourceful. Preferably like Macgyver. One time on a flight after take off, we got out our laptops to get ready for a battleship race to inbox zero and we realized that between us we had way too many devices to plug in. Naturally, without flinching, Tony pulls an oversized power strip out of his Zappos backpack. Resourcefulness > Resources.

Speaking of airports … from an airport one day in late 2011, I texted Tony for some advice because I was about to take on some investors and I wanted his feedback. By the time I landed at my destination, he and I had agreed to a completely different deal and he became the investor instead. One condition: I had to move my HQ to Vegas. We fist-bumped over Skype and the deal was done. It changed my life in many ways.

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.”

So, what do hot air balloons, worm farm visits, fernet lessons, delivering happiness bus hand-stand contests, llamas and a ton of lessons (some easy and some not) have in common?

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