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The Sunday Confession
This morning I didn’t want to write this column.
I wanted to stay under the covers, scroll Zillow for homes I’ll never buy, and argue with my dog about why socks and Band-Aids are not a balanced diet.
But here I am anyway, banging out words on a Sunday, because this thing is my therapy.
It’s how I remind myself that what we do in adtech is not that important.
And I know—this is where people start clutching their pearls.
“Not important? But we’re saving journalism! We’re protecting democracy! We’re building the future of humanity, one cookie-less identifier at a time!”
No. You’re f-ing not.
The guys on all those panels in Cannes are sad little men trying to explain why they are still single and childless at 55.
Let’s get brutally honest: we are not gods, we are not nation-builders, and we are not defenders of the realm. We are ad people. We move pixels around screens so brands can sell sneakers, soap, and dating apps to people who will ignore them anyway.
And yes, I know this opinion makes me radioactive.
For years I was invited to all the conferences, the big-name events, the podcast merry-go-round. But every time I pitched a topic, the answer was no. Why? Because I wouldn’t play the game. I wouldn’t kiss the rings. I wouldn’t get on stage and declare that some SVP of Bidstream Alchemy was an “adtech deity” who had parted the Red Sea of data privacy.
I refused to bow to the church of Kool-Aid. And that, my friends, makes you persona non grata.
Believe in yourself? Sure. But let’s not confuse adtech with divine intervention. You’re not a prophet, you’re a techie. You built some clever queries. Maybe you optimized a workflow. Maybe you stitched together an LLM wrapper with a UI that doesn’t crash every five minutes. Good job. You didn’t cure polio. You didn’t negotiate the Camp David Accords. You’re not Aristotle. You’re a guy with a hoodie and a pitch deck.
And that’s the point: don’t be that guy.
Been There, Done That, Bought the Hoodie
Of course, I know the disease because I caught it myself.
When I made my first few million, I strutted around like I’d cracked the secret code to the universe. I was that guy—the one who equates money with moral superiority. The one who thinks net worth is self-worth.
The one who believes that wealth doesn’t just buy comfort, it buys virtue.
That belief destroyed me, and my family — and it always will.
And in adtech, it’s not just common—it’s expected.
Everyone’s chasing the next comma in their bank account.
Everyone’s “this close” to unicorn status, one acquisition away, one SPAC away, one IPO away.
It’s a treadmill that never stops. You keep running, and the carrot keeps moving.
The tragedy?
Most people don’t even realize they’re strapped into the machine.
Brian O’Kelley Gets It
Brian O’Kelley—who has been in the trenches, sold the companies, built again, and cashed the checks—calls the bluff.
“I don’t believe in billionaires. I think it’s just ridiculous,” he told Fortune.
Think about that. This is not a kid railing against inequality on Twitter. This is someone who actually lived it. After selling his company, he walked away with under $100 million. In Silicon Valley math, that’s considered pocket lint. But instead of seeing it as “not enough,” O’Kelley drew a line.
“We just figured out a number that we thought was enough money—to be able to buy a house and things like that—and then we doubled it, and we gave the rest away.”
That’s clarity. That’s sanity. That’s someone who refused to chase the dragon of eternal more.
He still builds—Scope3 is his latest venture, tackling emissions data in the supply chain. But he’s not playing billionaire cosplay. No yachts. No helicopters. No Bond villain lair with his name on the gate. “I will never be that wealthy. Even if Scope3 is immensely successful, we will give that money away.”
And here’s the part people can’t swallow: “We never wanted to have so much money we didn’t have to make choices. It’s meant that we can’t be completely ridiculous about our life. We have an amazing life, we can do almost everything we want. But we can’t quite do anything we want—we have to talk about our budget like anybody else does.”
That’s the lesson. Choices matter. Accountability matters. Being forced to make trade-offs is not a curse—it’s what keeps you tethered to reality.
Billionaires Are Obnoxious (and Addicted)
And O’Kelley is right about billionaires being obnoxious.
Bezos’s $46 million wedding in Venice, dripping in diamonds and super yachts, was not aspirational—it was embarrassing. Tech bros parading into inaugurations decked out like the Met Gala for lobbyists? Obnoxious. The fact that there are now more than 3,000 billionaires while whole countries are collapsing under debt? Obnoxious.
As O’Kelley put it: “You can’t have a yacht and a helicopter and an island, and a big building with your name on it and all these things, because then you’re just sort of obnoxious. No human can actually truly appreciate that.”
And here’s the kicker: even when you become the billionaire, it’s not enough.
Look at Elon Musk. The man won capitalism. Rockets, satellites, cars, social networks—check. More cash than Croesus. But he couldn’t leave it there.
Instead, he’s been torching Tesla’s credibility and nearly sinking Twitter/X because money wasn’t enough. He wanted political clout. He wanted cultural dominance. He wanted to rule the world.
That’s what happens when wealth stops being freedom and becomes pure ego fuel. Ego is a fire that never stops eating.
How Not to Be “That Guy”
So if you want to avoid turning into the cautionary tale, here’s the playbook:
LinkedIn Is Not Therapy: Redefine Success
Your job is what you do, not who you are. Stop stapling your self-worth to your LinkedIn headline like it’s the Dead Sea Scrolls. Nobody is impressed by “visionary growth-hacking AI thought leader.” They’re scrolling. They’re not clapping. The real flex is being able to shut your laptop and still recognize yourself in the mirror.
Stop Chasing the Next Comma: Cap the Ego
Set a number that’s enough. Write it down. Stick it to your fridge. O’Kelley literally doubled his “enough” and gave the rest away. If you’re still sprinting past your own number, you’re not ambitious—you’re an addict. And here’s the bad news: there’s no rehab for billionaires.
Be More Than a Spreadsheet: Diversify Your Identity
Learn to bake bread. Coach your kid’s terrible soccer team. Paint something hideous. Volunteer. Even boredom is healthier than being defined by dashboards. If the only interesting thing about you is your QBR deck, you’re not a human being—you’re a PowerPoint in khakis.
Consequences Are Human: Stay Accountable
Unlimited wealth erases consequences, and consequences are what make us real. Budgets aren’t punishment—they’re oxygen. If you never have to say “no,” you’ve stopped being a person and turned into a cartoon billionaire with a Gulfstream.
Coach Builds Character: Spoil Less
Luxury feels like a reward, but it’s a trap. Spoil yourself too much and you’re unbearable. Spoil your kids too much and they’ll think coach is a violation of human rights.
O’Kelley admits business class at 6’5” is his indulgence—fine—but he doesn’t want his kids thinking it’s the baseline. Because once luxury becomes the floor, reality feels like an insult.
The Punchline
The worst fate isn’t failing to become a billionaire.
The worst fate is becoming one and still thinking that’s who you are.
And if that stings? Good.
It means you needed to hear it.
