Dennis Yu interviewing me for the Rising Talent Podcast, July 2026. About nine minutes.

Dennis Yu had me on the Rising Talent Podcast to walk through how agencies actually change hands. Not the theory of it. The part where an owner who has never sold anything works out what their business is worth, gets their numbers in order, and gets to a close without losing the deal halfway through.

Here is the short version of what I told him.

Most owners have no idea they are allowed to sell

This is the thing that surprises people. A founder will run an agency for nine years, take a decent income out of it, complain about it constantly, and never once seriously ask what it is worth. They assume selling is something that happens to other people, at other sizes, in other industries. It is not. If a business has clean books and can run for a week without the owner in the room, somebody will want it.

Dennis and I spent most of this conversation on that gap, because closing it is most of the job.

Stop betting on the Hail Mary

The mistake I see on the buy side is falling for one deal. An operator finds a business they love, decides that is the one, and spends four months chasing it. Then the seller gets cold feet or a better offer, and the operator has nothing. Four months, no deal, no pipeline, back to zero.

The fix is unglamorous. Build deal flow so no single conversation carries your whole year. When we are running properly we will have around twenty-one offers out at once. Not because every one closes, but because the ones that do close are the ones you were never emotionally married to.

Nobody is running ads for this

We do not buy ads to find deals. Automation and AI do that work now, and the difference is not small. Our sourcing costs came down by roughly seventy to eighty percent, and the volume of deals we see went up around tenfold. Same team, same hours.

That is also the honest answer when people ask what AI actually changed in this business. It did not replace judgement about which businesses are worth buying. It removed the expensive, boring part in front of that judgement.

Exit prep is not complicated, and it should not cost you anything

When an owner tells me they want to sell in a year, the first thing I ask for is boring: a clean profit and loss, three years of financials, and a CIM that explains the business to somebody who has never heard of it.

That is the whole starting kit. If a broker wants to charge you to assemble it, walk. We put that together for owners at no cost, because a seller with organised numbers is worth more to everybody in the room, including us.

AI integration is now the biggest single lever on your multiple

This is the newest change and the one most owners have not priced in. Two agencies with identical revenue no longer get identical offers. The one that has genuinely built AI into how the work gets delivered gets a materially better multiple, because the buyer is purchasing margin that scales rather than headcount that does not.

If you are eighteen months out from selling, this is the highest-return work available to you. Not a rebrand. Not a new website. Rebuilding delivery so it does not need another twelve people to double.

The twenty-four to thirty-six month window

Most sales that go well were set up two to three years before the close. That is the window where you clean up the books, reduce owner dependency, and get the operational story straight. It is also the horizon that matters for SBA financing, which is how a large share of these deals actually get funded.

Selling in ninety days from a standing start is possible. It just costs you money, and the money it costs is usually more than two years of preparation would have.

Why deals die

You cannot force love. I have had deals with perfect numbers on both sides fall apart because the seller could not picture handing their people to that particular buyer. That is not irrational and it is not a problem you fix with a better spreadsheet.

What you can do is have enough conversations running that one collapse is an inconvenience rather than a catastrophe. Which brings it back to deal flow.

Structure is what actually closes it

Price gets the attention. Structure gets the signature. Seller financing, earn-outs, SBA preapprovals, an equity rollover so the founder keeps some upside: those are the tools that bridge the gap between what a seller wants and what a buyer can defend to their own capital.

When a deal feels stuck on price, it is usually not stuck on price. It is stuck on risk, and structure is how you move risk around until both sides can live with where it sits.

Watch the whole thing

The full conversation with Dennis runs about nine minutes and covers all of the above plus how we work with investors on the buy side. If you are an agency owner thinking about an exit in the next couple of years, the exit prep section is the part to start with.

Deal volumes and cost figures in this piece are from my own firm rather than an outside auditor, and are described as I gave them on the episode.