Creating Financial Clarity Before Signing a Deal

We were introduced to the owner-manager of a specialist training business operating in a niche sector who needed business owner exit planning support before making any deal decisions. The business had grown steadily and was producing strong EBITDA relative to its size, with credible interest from both trade and private equity buyers.

The founder had a financial adviser already, but had reached the stage where an exit, partial sale, or investment round was actively being considered and he did not feel confident they had the specialist knowledge required to help him and his family through a potential deal.

Conversations with potential buyers were already underway. Indicative valuations and deal structures had been discussed, including majority sale, minority investment, and earn-out structures.

The central question repeatedly asked of him by investors and advisers was simple:

“What’s your number?”

He did not have a defensible answer.

Like many founders, he could describe revenue, EBITDA, pipeline, and buyer interest in detail. What was missing was clarity on the personal side of the equation.

What level of proceeds would actually support the life he and his wife wanted.
What trade-offs were acceptable.
How different deal structures would change his future options.

At the same time, operational pressure had recently reduced due to strengthening the management layer, creating a rare window to step back and think properly rather than react. He described this as the first real opportunity to stop and take stock.

Business owner exit planning starts with clarity

Our first step was not to discuss buyers or valuation multiples.

It was to establish the foundations to make a great decision.

This sits at the heart of our Cash Out With Confidence approach.

We began with a structured priorities and values exercise, completed by him and his wife independently, to clarify what mattered most personally and as a family. This created a working reference point for all later modelling and trade-off discussions.

Alongside that, we gathered detailed financial inputs. Income, assets, pensions, property, spending, education costs for children, and known future commitments such as university funding and parental care support.

This forms part of our fixed fee financial planning process.

Turning life goals into numbers

Using cashflow modelling, we then built a forward projection of his financial life under multiple scenarios. This included different exit timings, different sale values, continued involvement through non-executive work, and variations in post-sale income.

Rather than producing a single “answer”, the model allowed interactive testing of assumptions. Changing exit dates, proceeds, income levels, and lifestyle costs, so they could see the consequences clearly.

This shifted the conversation from abstract valuations to genuine context.

Rather than starting with:

“What can I sell for?”

The more useful question became:

“What outcome do I actually need, and what structures get me there safely?”

This type of work underpins our business owner exit planning approach with founders and our wider exit planning for business owners conversations.

Testing real-world options

We tested immediate trade sale, partial liquidity with retained control, and delayed exit with further growth.

We also modelled the effect of property changes, education funding, care commitments, and lifestyle spending increases following a transaction.

Particular attention was paid to tax timing, including capital gains tax payment and cashflow effects in the year following sale, using current guidance from HMRC.

As the modelling developed, offers and deal structures were no longer judged purely on headline price, but on how well they supported long-term personal and family objectives.

The founder could see which ranges and structures worked and which created unnecessary future pressure.

Client reflection

He later summarised the value of the process in his own words:

“Thanks very much for all of your efforts. Really, really appreciate it. Very grateful.

Explaining to his fractional CFO after the first meeting, ‘we had a planning discussion around our “magic number”. This was an enjoyable, different, and interesting meeting. We did some interesting exercises about what’s important in life, rather than focus purely on the financial options at this time, which was unexpected and valuable.’”

The outcome

With clarity established, the exit discussion moved forward on firmer ground.

He entered buyer and investor conversations with a defined financial target range, a clear understanding of acceptable structures, and a tested view of post-transaction life.

The process also highlighted that continued non-executive and advisory work after a transaction was both realistic and desirable, and this was incorporated into the modelling rather than treated as an afterthought.

The result was not a forced decision, but a grounded one.

Exit, partial exit, or investment could now be evaluated against a clear personal benchmark rather than guesswork.

This case illustrates a recurring pattern with founder-led businesses. Transaction conversations often start before personal clarity exists. When that happens, price becomes the anchor and pressure drives timing.

By contrast, when personal financial requirements and priorities are modelled first, negotiations become more disciplined, options are preserved, and decisions are less likely to be regretted later.