We’ve made it to issue thirty of The Two But Rule, and I’m a week away from finishing the manuscript for the book. It’s time you know some things about me.
First, I'm not going to tell you how I'm a world class expert on managing my but. I don’t hold the Harold Kiester Chair of Two But Sciences at Harvard, though I have applied for the position.
No, I'm here, and I’m writing the book, because I could fill a castle library with volumes on how I failed to embrace my but. How I didn't find a way past a negative roadblock. How I spent years as a but-head, followed by more years ignoring all the buts.
A But Full Of Experience
I've been a product executive, startup founder and emerging technology scout for most of my career. I was in AI before it could tell you convincingly that it was alive. I was building mobile apps before the iPhone could handle data and phone calls at the same time. And I once tried to convince one of the founders of Google to join our internet research lab … while he was still in grad school. (He politely turned us down, and later hired a fair number of our best people.)
I worked for IBM three times and was a startup CEO a couple times. I started a multi-national consortium for joint R&D a few years back. And I’ve held the official title, “Seeker Of Awesomeness,” not once but twice. One company put it in my employment contract, and IBM put it on my business cards.
Sometimes things worked out. Sometimes my thing didn't work out, but the thing my thing was about did. Sometimes things went in the drawer of failed experiments and are there now, waiting for someone to open that drawer and try them again.
Even with decades of experience, living and working all over the world in a surprisingly wide range of fields, I still can’t tell you how I succeeded beyond my wildest dreams, how I saved the world two or three times, or how I maintain such a hard and well-formed but that it could appear in a Marvel movie. And that’s ok. You don't need Captain America-but guy. He has no idea how to get your but in shape. He doesn't realize that showing you his workout routine isn't going to do for you what it did for him.
On the other hand, experience counts for something. True story. I took an entrepreneurship class in grad school where the professor had the audacity to announce that they were a great entrepreneurship teacher, because they had never started a business. I'll give them points for moxy, but we weren’t buying it. Now, if they had started a dozen businesses of many different types over a couple decades of trial and error, and those businesses all failed so spectacularly that they had to get a job teaching, then they might have been onto something.
Saying, "I can teach you how to avoid mistakes, because I have trafficked in every kind of mistake," is a claim I can get behind. It's not the blind leading the blind. It's the person who's had a broken arm showing you how to fashion a sling for your broken arm.
The Two Buts Path
My whole life, the thing that got me involved in way-too-early projects, risky startups, and roads-less-traveled was a fascination with seemingly impossible problems. I enjoyed grappling with the nuances of the issues, the balance points, and the constraints. I have a high tolerance for sticking with a puzzle, even puzzles where it’s not obvious that there will ever be a solution. I’ve always been more fascinated with how something doesn’t work--how it doesn’t work yet--than in how to use it as directed.
This crystallized for me when working for an innovation consulting firm in Silicon Valley. A colleague there would often say, "Always but the but." That one line stayed with me, and it's led me into more trouble--and out of more jams--than any other single cognitive tool. It also helps me in times of transition.
Fresh Out Of Buts
In 2022, after almost a decade working on early blockchain technology, I called it quits. Blockchain is a slag heap of bad ideas buoyed up by a lot of hot air rising from a global cesspool of financial speculation and money laundering known as cryptocurrency. I had been hard at work shoveling, "But that didn't work, BUT it could if’s," upon, "But that also didn't work, BUT it could if’s,” for years. Suddenly I found myself fresh out of buts.
For a full account of the cryptocurrency quagmire, check out Ben McKenzie and Jacob Silverman’s new book, “Easy Money: Cryptocurrency, Casino Capitalism, and the Golden Age of Fraud.” It’s an incredibly well researched and written book. The last chapter will make you cry.
Running out of buts on blockchain, for me, was a big transition. I was reasonably successful in the field. But I knew most of it was a grift, right down to the basics of the technology. BUT I was making really good money, which I needed to support a family. But I couldn't get it out of my head that I was the beneficiary of a speculation game that made money off the backs of so-called greater fools, duped into ‘investing’ money they often couldn’t afford to lose by people who should have known better.
That’s when I came across this saying:
"Misery comes from living in a manner inconsistent with your values. Despair comes when the obvious alternatives are also inconsistent with your values. Hope comes in realizing that those aren't the only options."
I might have been able to continue finding more buts to pile on the blockchain bonfire. Instead, I stopped cold, deciding I didn't want anything more to do with an industry that had beat the land speed record going from idealistic inception to irredeemable corruption and hypocrisy.
Finding Your But Again
But … the problem was that I had occupied my mind so thoroughly with this topic for so long that I had no idea what else of value I could bring. BUT … but there was my old colleague in my head saying, "Always but the but."
Writing this series, and the book helped me find my but again. I hope it helps you find yours.
Love this. Thanks for sharing. It is great to see your journey written down along with this level of transparency. I can see a couple of paths we have crossed together along that journey. Very helpful, as a fellow tech leader, to have you articulate some of the same pitfalls and struggles I have encountered. It is encouraging to know that I am not alone.