“Happy at Any Cost”: Lessons from the Amazing Life and Tragedy of Tony Hsieh

Tony Hsieh was an icon in the entrepreneurial world. Someone who was able to build a very significant & successful business in the first dotcom boom and also in the Web2 world with Zappos. He literally wrote the book on customer service with “Delivering Happiness” sharing all the secrets that made Zappos the standard for building an amazing business on the foundation of customer care and happy employees. 

One of the most thoughtful, generous and kind entrepreneurs around, he helped hundreds if not thousands of fellow entrepreneurs and helped rejuvenate the Las Vegas downtown area. That’s the great tragedy as he succumbed to substance addiction from trying to deal with his own mental illness. He focused so much on helping others and making others happy but ignored himself along the way. 

So many lessons from his life and the book that I took out. Especially important to confront these as we see growing mental health issues among the populace at all age brackets and geographies. This i see as the biggest negative result from the pandemic and the poorly executed lockdowns we saw executed by incompetent or malicious government officials and health authorities. (Yes, I am still incredibly angry about this). 

It seemed to me that Tony had lost purpose in life after accomplishing so much at such a young age. When you have so much money and resources, you stop having any constraints. You can do anything you want, go anywhere you want, buy whatever you wish. All the freedom and options can be debilitating. How to channel that? It’s toward a larger purpose. Having a big vision. You always have to find a new, bigger mountain to climb. 

The biggest lesson for me was how important it is to learn to take care of yourself physically and mentally. Ie. be a little bit selfish. Therapy is awesome and I highly recommend it personally but using any substance seems to be a really bad idea which is what led to Tony’s tragic end. 

Getting good sleep is critical. And just as important: doing a lot of regular physical exercise with weights & lots of cardio via running/biking/hiking. Even better if you do a martial art on top of this. It does wonders for your mental health. 

The second biggest lesson was how critical it is to surround yourself with the right people. Tony near the end of his life was surrounded by sycophants and opportunists unwilling to stand up to him or tell him NO. The more successful you are, the higher up you go in any organization it becomes harder to understand what is really happening around you. Information gets filtered, you start getting only positive information or news. It leads to an unrealistic view of the world. You become out of touch & maybe a little bit unhinged. You have a dangerous filter bubble. 

Incentives really matter. Hard for people to tell you the truth if you surround yourself with younger up & coming people who worship you and are reliant on the money you pay them. No one can or is willing to push back or say NO to you. This is exactly what happened to Tony. 

That is why you need to have 3 different levels of people you regularly spend time with. 

Level 1: People who are much further along than you are. Mentors or elders you respect. People who you aspire to be like but have much work to catch up. And who you can get a roadmap and lessons from. You also need someone to question and challenge you. At least for me, if someone is further along I will more likely pay attention.

Level 2: People at your own level: there is something about being on the same journey. Almost like a mastermind of equals. I think of these folks like your “gym buddy”, you egg each other on, your trade ideas and knowledge. 

Level 3: People you mentor and teach. You have not mastered anything if you cannot show someone else to do it. You learn so much in the process personally as I have found. Frankly, as technology and the world changes so much, young people tend to be at the forefront, so this is a good way to stay relevant. This is also why I do lots of volunteer pro bono mentoring & speaking at various Startup programs and accelerators still. Additionally, you have an obligation to help bring others along. Sharing your knowledge and your experience to help others is a core part of the Silicon Valley ethos. Ie. Pay it Forward. 

The point is as I’ve mentioned so many times. Your community matters. You are the average of the 5 people you spend the most time with. But you need to make sure you have people and many different stages so you can get the right data environment to really know what’s happening around you. And of course at the core, you need to have a mission and work and improve yourself first. If you are comfortable being yourself and by yourself, all good things will flow from this. 

Thank you Tony for everything that you did and for this great reminder and life lesson for all of us. You won’t be forgotten. RIP.