Going back to a job after being the CEO

I spent three years as the founder and CEO of a company. This year I'm buying media at an agency.

There is a version of this that's a failure story and a version that's a strategy story, and the honest answer is that it started as the first one and turned into the second faster than I'd have predicted.

The part I expected to be hard#

Titles. I'd been the person who decided things, and now I'm the person who executes against someone else's decision, and I assumed that would be a daily indignity.

It was, for about three weeks. Then it stopped, and what replaced it was a genuinely pleasant discovery: an enormous amount of what I'd been carrying wasn't work, it was responsibility for outcomes I couldn't control. Payroll. Whether the company existed next year. Whether the people who joined me made a good decision. That weight is invisible while you're under it and extremely visible the week after it comes off.

I slept better in January than I had since 2013. That's not a metaphor.

The part I didn't expect to be hard#

Being bad at something again.

I've been buying traffic since 2009 with my own money, so I arrived thinking I knew this. What I knew was how to spend a few hundred dollars a day carefully. That is a completely different discipline from operating at scale, and the difference isn't a multiplier — it's a different job with different failure modes.

At small budgets your problem is signal. You never have enough data and every decision is made on noise. At large budgets you have all the signal you need and your problem is that mistakes execute instantly and completely. A misconfigured campaign doesn't waste $200 while you notice. It spends real money before anyone opens the tab.

The skills I'd built were largely about extracting conclusions from thin data. Most of them were irrelevant, and some were actively harmful — the instinct to intervene early, which is correct at $200 a day, is expensive when the account has enough volume to stabilize on its own.

Why this was actually the right move#

I get to see inside brands at a scale I couldn't reach as a vendor. For three years I sold to marketing directors and only ever saw the outside of their operation. Now I'm in it. I can see how the budget actually gets allocated, who really decides, what gets measured, and which vendor promises land as credible versus insulting. That's competitive intelligence I could not have bought.

The feedback loop is immediate and unambiguous. After three years of a marketplace where I couldn't tell how much of the volume was me, it's clarifying to work in a job where the number either went up or it didn't.

It bought me time to think. I don't yet know what I'm building next. The industry consensus is that you should go straight from one company to the next while the momentum is warm. I've watched people do that and start something they hadn't thought about because stopping felt like losing.

What I'm actually watching for#

I'm not planning to be a media buyer for long, and I'd say that out loud to anyone who asked. This is a paid vantage point.

What I'm watching for is the gap — the thing every brand I touch is doing badly with tools that don't exist yet. Three years of selling into this market taught me what people say they want. A year inside it will teach me what they actually do, and those have never once been the same thing in my experience.

The ego cost of the title was about three weeks. The information is going to be worth years.