So There I Was

The Ride Home

July 22, 2026 · #STIW

So there I was...

The Rock Store on Mulholland Dr., just outside of Malibu. I had just traded in my Ascot green BMW R850R for a graphite metallic R1100RT, the same model the CHP uses, and this was the first time I had a chance to push it. My Sunday morning breakfast adventure was with a rider far better than me, and to top it off Jeff was on a Ducati ST2. The push I needed to discover my comfort zone on a much bigger and taller motorcycle navigating the canyons of the Santa Monica Mountains.

A weathered wide-brimmed hat hanging off the handlebar of a graphite metallic 1998 BMW R1100RT parked in front of The Rock Store on Mulholland Highway, #STIW on the license plate

Jeff was the first client of the property management company I founded in the mid-nineties in Malibu and Beverly Hills. He owned an iconic house on the beach, something Tony Stark would envy and my company managed. A multi-billionaire and not the easiest guy, he had an amazing ability to find value where others did not. Real estate investment was his calling, but riding was his passion, and he had the means to do it all over the world and on the best bikes available. I was lucky to have time like this with a guy like him. These were the days before I was DocAustin, and just Malibu Steve.

I stirred some egg yolk into my hash browns as Jeff shared an idea he had been working on. Cornering the pay phone market. Now, it's 1998, so there are cell phones, but there are still about 2.1 million pay phones. 20 years later that number would drop to less than 100,000. Jeff's thesis was simple: people who could not afford cell phones still relied on pay phones, and his idea was to buy all of them, reduce their availability, and crank up the cost of a call. The math was fantastic. But I was so troubled by it.

We ended our morning with a beautiful ride up Mulholland, down Encinal, then Decker Canyon, to PCH, and back to Broad Beach where I left Jeff to begin my ride home. The thing about bikes, and the same can be said about running and swimming, is that you have a lot of time with your own thoughts. It's meditative. And Jeff's plan, which ultimately, thank God, never played out, left me deeply unsettled.

The economics of cell phones flipped Jeff's equation. The average price for a phone when he hatched his plan was over $400. A few years later you could get a Nokia 3310 for about $160. Cheaper than he would charge someone for one call per day, and you didn't need a pocket full of quarters drawing attention to you like a bell on a cat collar.

Over a quarter century later I am still thinking about the decision process of someone like Jeff, and it is at the root of my deep concern for the "empty chair." The room where decisions get made and the people affected by them do not have a seat at the table. Before he passed away, Jeff went on to make a lot more money by doing some incredibly shady things, and is universally reviled. His epitaph is not the wealth he amassed, but the cruelty of his decisions. I saw how his mind worked and how he calculated value and his unique market insights. But in terms of my own expectation for a moral compass, he had none.

I gave up riding sometime after I moved to Austin. I love this area, but it has become too crowded, with too many distracted drivers on too many cell phones (ironically), and simply too much risk for my family for me to be racing around on a motorcycle. I miss riding, if I'm being honest, but my own process for ethical decision making makes it the right choice. I look at it through the lenses of magnitude of consequences, consensus, probability, proximity, and concentration of effect. These are the same lenses that should apply to all our decisions, especially as we see the erosion of the deliberative layer within organizations.

There are fewer and fewer people responsible for decisions with greater and greater impact, and there is no better magnification of the potential for negative outcomes than in the age of AI. Your dev team of 10 has become a team of one or two orchestrators plus an LLM that moves at the speed of ideas and tells everyone all of theirs are genius. History is replete with multi-billionaire titans devising ideas that are really, really harmful, so don't let an AI tell you yours is not one of them.

What is your process for weighing the outcomes of your decisions, and who should be sitting in the empty chair at your table?

OLÉ MCS logo A DocAustin story, carrying the OLÉ mark · olemcs.com #STIW

#EthicalDecisionMaking #Leadership #AI #DecisionMaking #TheEmptyChair #Motorcycles #STIW

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