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When I was in my thirties, I never imagined I would be where I am today. I’m rebuilding my firm from the ground up, at sixty, around artificial intelligence. If you had told me back then that this is how my career would go, I’m not sure I would have believed you.
If you’re reading this and you’re nowhere near sixty, maybe take it as a bit of a warning. And if you’re closer to my age, I hope you take it as the opposite, as a little permission.
I’ve noticed that a lot of founders my age have quietly made up their minds about something. They’ve decided the AI wave came along too late for them, and that this kind of transformation is a young person’s game. I understand the feeling, because I used to think the same way. It turns out I was wrong. Age isn’t the obstacle here. If anything, it might be the advantage.
The Call
A few years ago I made a decision. I was done running a lifestyle business, and I wanted to build something that could actually scale and someday sell. I’m a solo founder. It was during Collective54 office hours early in my membership when I was delivered a message loud and clear: find a strong number two.
So that’s what I did. And almost immediately, this person started turning over rocks I had been stepping around for years, things I knew were there but had been content to ignore.
The Trials
One of the first things he did was ask my team a simple question. What is your role here? Nearly every time, the answer came back the same way: “Whatever Rob tells us to do.”
That was a hard thing to hear, because a company that runs on whatever the founder says isn’t really a business. It’s a bottleneck with a payroll. And it told me something uncomfortable about the team I had built.
Within a year, every single one of my full-time employees was gone. All of them. I won’t pretend that was easy, but it was honest. The truth was they didn’t want to be held accountable. They were comfortable doing the work the way they had always done it, and they had no real interest in the journey I was trying to go on.
I should be candid about something else, too. My transformation was probably a good ten years late. For a long stretch I was a single dad raising my daughter, and there were risks I was unwilling to take while she still needed me at home. I cherished those years and would not change a thing. But it added years I never expected to spend back when I was younger and mapping out how all of this would go.
So I didn’t start over because I finally had it all figured out. I started over because I was finally able to.
The Transformation
As painful as the turnover was, it turned out to be a gift. I had a blank slate, with no holdovers to slow down the changes I wanted to make. That’s when I committed to making Fintelligent an AI-first firm.
This is the part I want to be clear about: an effort like this has to be led by the founder. You can’t hand it off to someone else. I happen to be fortunate, because I know my way around technology and I can build things even without knowing how to write code.
As I dug in, I started to see the work in front of me in two buckets:
- App-based work, which needed software and structure to run well.
- Agent-based work, which AI could handle with the right oversight.
We are leading with service, not tech. US service sector revenue dwarfs software revenue by a ratio of at least 6-to-1. Services is where I want to be.
So much of finance and accounting is routine, and it turns out that agents are remarkably good at routine. That changed what I needed from the people I hired. I stopped looking for more accountants, and I started looking for orchestrators instead.
An orchestrator does three things:
- Directs the AI and the agents.
- Verifies that the data coming back is actually right.
- Uses judgment to help our clients make more money.
That last point is the whole reason clients hire us in the first place, and it’s the one thing no agent can do for them.
The Part Nobody Talks About
There’s a quieter advantage to doing all of this at my stage of life, and it doesn’t get talked about much. Most of my big financial commitments are behind me now. I’ve had time to build liquidity outside my business. The tuition is paid. I sold my house and moved into something smaller, where somebody else handles the upkeep.
What that buys me is two things most founders are desperate for: staying power and focus. I’m not stretched thin, and I’m not distracted. I get to point all of my energy at the business.
The Return
So was it worth it? I work a lot these days, and I love it. I don’t think I’ve ever had more fun in my career. I get to talk with founders every single day, smart and innovative people, and help them fix their profitability so they can turn around and invest, grow, and run their own AI plays. The best days of all are the ones where I help a founder pass due diligence and finally exit at a premium.
I’ll be honest that my story isn’t finished. The payoff is still murky, and I can’t tell you yet how it all ends. But I have never been more confident about where my company is headed, and I have never enjoyed the work more than I do right now.
So if you’re deep in your career wondering whether you’ve got another act left in you, let me say this as plainly as I can. Go for it. Don’t let anyone tell you what you can’t do because of your age. The AI moment didn’t pass you by. You might just be exactly the right person, at exactly the right time, to lead it.
If this resonated, here are three ways to go further: