Year nine of running my agency, I sat in my office in Belfast and said, “Screw it, I am done.” Two years later I sold the agency for a multi-seven figure sum and exited in 2022. The difference between those two moments was not the business. It was that I had spent the 24 months in between building optionality.

Let me ask you the question almost no agency owner answers honestly: when is the right time to sell?

The honest answer is, when you do not have to. The day I sat at that desk, burnt out, the only two options I could see were walking out and never looking back, or selling. That is a terrible position to negotiate from. I would have taken any offer on any terms at that moment. My brother Marty was my business partner, and he talked me off the ledge. Thankfully, he did. Because the feelings, whether they were good or bad, were momentary. The decision would not have been.

Optionality means having multiple paths I could choose to walk down at any time, rather than the one path you walk when you have run out of choices. This article is how to get there.

The three paths a well-run agency should always have open

Optionality is not “thinking about exit.” It is having more than one outcome available, and being in control of which one you choose.

At any moment, a well-run agency should have at least three paths open.

Path 1: Keep the business and take the cash flow. The agency runs without you. It generates predictable profit. You take distributions. You do not sell. You just benefit from the cash machine you have built.

Path 2: A partial sale or partnership. You bring in a partner, sell a minority stake, or merge with a complementary business. You retain equity, you stay involved, and you reduce your personal risk while unlocking some of the capital sitting inside the business.

Path 3: A full exit. Someone else takes 100%. That is what I did.

The problem is that you only think about optionality when you are completely exhausted. By that point, you have one path: sell to whoever shows up, on whatever terms they offer.

Optionality is built in the boring months. Recurring revenue, delivery systems, client diversification, your leadership team, pricing discipline, sales systems, KPI cadence, data hygiene. All of the operational work I have written about across the other pillars is, in the end, optionality infrastructure. The thing that determines whether year nine of your agency is the moment you negotiate from strength or the moment you negotiate from desperation.

The one-page acquirer story

On top of the operational infrastructure sit two things buyers actually buy: the acquirer story and the absence of obvious risk.

The acquirer story is not a pitch deck. It is a one-page document that answers five questions a buyer will ask before they ever consider a price.

1. What does your business win at?

This is positioning, and it needs to be narrow. “We are a full-service creative agency” is not positioning. It is a description of everyone. “We are a performance creative engine for D2C brands doing £5M to £30M in revenue” is positioning. A buyer can understand it. They can see the market, the customer, the capability, and how it fits into whatever they already own.

At my agency, positioning evolved over the years. Early on we did everything for everyone. By the time we sold, we had a clear service line, a clear client profile, and a clear reason somebody would choose us over any other agency in Belfast or beyond.

2. Why do your clients stick with you?

This is the retention mechanism. Buyers want to see that revenue is durable, not one-off. What keeps clients coming back month after month? What stops them leaving?

In a strong agency, retention comes from three things:

If retention is based on “they like working with us”, that is a relationship, not a mechanism. Relationships leave when people leave. Mechanisms survive transitions.

3. What is your economic engine?

Pricing model. Gross margin range. Capacity constraints. A buyer needs to see that the business generates margin consistently, not just revenue. If your margin moves around unpredictably, the buyer assumes the worst quarter is the real number and prices the business at that level. This is exactly what agency profit benchmarks anchor against.

4. What makes it transferable?

Can delivery run without the founder? Can sales operate without the founder’s personal network? Does the reporting cadence exist on a calendar, not in your head?

Transferability is not about removing the founder entirely. It is about proving the business can function at 80% or better without them. This is where the owner extraction work becomes the moment that turns a business into an asset. I left my agency five years ago and it is still doing brilliant things. That is the proof a buyer needs. The business is not you.

5. What is the growth opportunity post-sale?

Buyers are not buying what you have built up to now. They are buying the opportunity of what they can build on top of it. Can they cross-sell your services into their existing client book? Can they expand geographically? Can they productise your offer?

One of the best things I did before our sale was build a three-year growth plan for what we would deliver if the acquirer never bought us. It showed them we had thought about growth at the highest level. We were already on track. With their resources, we could do it faster. That document changed the tone of the conversations.

Write all of this on one page. If you cannot, you are not ready. You are unclear, and clarity is the first step.

The serendipitous pivot: build authority with the buyers before you need them

This is the move almost no one would even consider.

In the years before we went to market, we designed websites and brands for the M&A firms (the merger and acquisition firms, the money people, as I call them) in Belfast who would eventually be involved in our sale. We built around six brands and websites for strategic businesses in that space.

We did good work for them. So when anyone in their world asked, “who do you know in digital?”, we were the only name that came up.

It compounded. We had a client called Boojum who went from three stores to 22 and was then acquired. When I walked into any business in Ireland and said we worked with Boojum, people knew the brand. That association was a visible success story that opened doors before the conversation about us even started.

The lesson is uncomfortable but true: position yourself in front of your future buyers and their advisers years before you need them. Make your work visible. Make your results measurable. Become a known name in your target buyer’s world before you ever need to sell.

The second-bite trap

There is a deal structure called the second bite that most agency content never covers properly. It is where a lot of money is made, and where a lot of founders get trapped.

A second bite means you do not sell 100%. You sell a majority and retain a minority stake. Then you participate in the upside when the business sells again, usually to a larger buyer three to five years later.

This is how private equity roll-ups work. They acquire your agency, combine it with others, grow the group, and sell the group for a much higher multiple than they paid for any individual piece. Your retained equity rides that multiple expansion. I am working with a couple of agency owners on exactly this kind of deal right now.

It sounds attractive. It can be brilliant. But only if four conditions are true.

The business must grow without you. If growth requires your energy, a second bite traps you in the business for another three to five years. You have sold your freedom and kept the obligation.

Reporting must be clean. Delivery leadership must exist. Pipeline must be owned by a rule, not a person. Without those, the buyer cannot grow the business after the deal, and your retained equity goes sideways.

The deal terms must make sense to you. A 60/40 split (60% on completion, 40% tied to performance over three years) is very different from a 90/10. Earnouts, rollovers, retention clauses, this is where deals get complicated and messy. Understand exactly what you are signing and what it requires of you both now and in the future.

You must trust the buyer. If you are retaining equity, your return depends on how they run the business after the deal closes. Due diligence is not one-directional. You should be vetting them as hard as they are vetting you.

The key question to ask yourself: if I retained 20% of my business and had zero operational control, would I trust this buyer to grow it? If the answer is no, or you are not sure, do not take the second bite. Take the full exit and move on.

You do not increase your valuation by sounding better

You increase it by removing the reasons a buyer would pay less.

Buyers apply discounts. Every gap in your business is a reason to reduce the multiple. Here are the six most common discounts I see, and the operator fix on each one.

Discount 1: Key person risk. Founder involved in sales, delivery, and client relationships. The buyer sees dependency. The fix is role-based ownership, an operating cadence, documented process, and a real management layer. This is the foundation that every other lever sits on top of.

Discount 2: Client concentration. One client is more than 25% of revenue. The buyer sees fragility. Lose that client and the business is impaired. The fix is to cap single-client exposure, grow your mid-tier accounts, and build deliberate client diversification.

Discount 3: Margin quality. Gross margin looks OK in aggregate, but you cannot explain it by client or service line. The buyer assumes the worst pockets are hidden. The fix is service-line costing, scope control, and margin visibility by client.

Discount 4: Revenue quality. Most revenue is project-based and volatile. The buyer applies a lower multiple than they would for retainer revenue. The fix is a retainer mix, longer commitments, and a land-and-expand sales motion.

Discount 5: Reporting risk. You cannot produce weekly numbers, or the data is messy. The buyer sees a control risk. The fix is a weekly KPI cadence and tight data hygiene.

Discount 6: Delivery risk. Delivery quality depends on specific people rather than a system. The buyer sees scalability as a risk. The fix is good handoff processes, QA checklists, and documented operations the team uses every day.

If any of those discounts hit you, fix it before you go to market. A buyer who finds it in due diligence will price it twice as hard as a buyer who finds it has already been resolved.

The perception trick during negotiations

A small story to close.

The minute there was serious interest in our agency, and people were talking about the business in other rooms, I switched on our retargeting ads. Instagram, YouTube, display. Every buyer, every adviser, every M&A person who had been on our website saw the agency everywhere they looked online.

At one point, a buyer told us, “you guys are everywhere.” Little did they know the campaign was costing almost nothing to run. We were already running retargeting; we just increased the ad spend for a six-week window during negotiations.

It created the perception that the agency was bigger, more visible, and more established than the numbers alone would have suggested. That is not deception. It is positioning. We were already running the ads. We just amplified them during the critical window. Perception of scale can be manufactured cheaply, in the precise weeks when it matters most.

What to do this week

Two actions.

One: write your one-page acquirer story. The five questions above, one page, no more. If you cannot fill in a section, that is the gap that is the work for the next 90 days.

Two: score yourself zero, one, or two on each of the six discount factors. Key person risk, client concentration, margin quality, revenue quality, reporting, delivery. Pick the three lowest scores. Those are your priorities for the next quarter.

If you want a complete picture of how your acquirer story and your discount exposure shape what your agency could be worth, the free Agency Valuation Calculator walks you through the assessment in about 10 minutes. It scores you across the same levers buyers actually price against, including the six discounts above and the transferability test.

If you are already inside the exit window and want to talk through the strategy, the Exit Advisory programme is built for founders planning a 12 to 36 month exit. Book a discovery call if you want to discuss where you sit on the optionality framework.

Hear this in practice on Exit Ready: