Inside the Office
“What’s wrong with me?” That’s a question I got three weeks ago from Jason (not his real name).
He’s a CEO I coach who’s wildly successful with multiple exits, big houses, serious watches, cars that get covered for the winter, and so on. And he built every bit of it himself.
Forty minutes into our session, Jason stopped talking about his next deal, went quiet, and asked: “What’s wrong with me? Why am I not happy?”
I didn’t answer right away. I recognized the question. I’ve asked it myself, standing in the middle of everything I ever wanted.
It reminded me of Morgan Housel’s new book that I happen to be reading, The Art of Spending Money. His argument is that making money and spending money are two different skills, and almost nobody who masters the first ever learns the second. And one line from the book immediately resonated with me: “What actually matters is the gap between what you have and what you want.” This is a book about making the most of what you already have while figuring out for yourself what is worth wanting.
Jason’s pile grew for twenty-five years. His wants grew right along with it. But while his net worth kept moving up and to the right, the gap never moved an inch. Nothing is wrong with Jason. He spent his whole life building gaps. Nobody taught him to close one. I ran Shindigz for over thirty years. Money was a scoreboard, and a fair one — it funded payroll, it told me whether my decisions were right. Wanting more wasn’t a flaw. It was the job.
Then came the having. Homes. Boats. Planes. Stuff. Each one gave a smaller hit than the last, and the hit wore off faster. The first felt like a trophy. The fifth felt like a transaction. Then, eventually, like a job. Every house needs a roof. Every boat needs a haul-out. I thought I was buying assets but I was really buying maintenance plans.
Eventually I realized how the thing that built my company — never being satisfied, never accepting a plateau — is the same thing that ruined how I was spending the money. We spend decades treating “enough” like the enemy. Then the wire hits, and the wiring stays. We just keep score with square footage instead of revenue.
So what did I ultimately tell Jason?
Nothing is wrong with you. Your machinery works fine. But it’s aimed at the wrong target. Then I gave him homework. I told him to look at your last five big purchases and answer honestly: who were they for? His were all, one way or another, for an audience. The audience never shows up. Nobody admires your car the way you imagined. They’re too busy picturing themselves in it.
Then I told him what has actually held value for me after thirty years of running the experiment: the classroom. The coaching. My family. Not one of them was a purchase.
I explained all this to him, then I said, “You spent your career closing the gap between where the business was and where it could be. And sure, that made you rich. But it will never make you happy. That gap only closes from the want side.”
Jason’s working on it. So am I.
-Shep
Worth Your Time
A company raises more than a billion dollars over fourteen years, builds a product loved by millions, grows revenue to nearly half a billion... and then the ending takes a turn nobody would have written a decade ago.
Is it a story about raising too much money, too fast? A story about shifting investor appetites? Or is it about an emerging technology overtaking the current standard? Maybe some combination of all three.
This essay* by Scot Wingo and the NC Tweener Times walks through what just happened to Airtable. I won’t spoil the plot, but it’s worth a scroll.
Read it, then tell me what you think and how you interpret what it means for how entrepreneurs should be thinking about fundraising and navigating the current software landscape.
*it’s free but you may need to provide your email to access it
I came to the conclusion a few months ago that enough can be the reward when it lets you focus on more important life tasks, like relationships and having the true luxury: time.
Now when I look at what I want (and need) 20 years from now, I look for ways to build now that serves the both of us ‘me’.
“Anything You Want” by Derek Sivers helps if you are seeking that changed mindset.