How Much Value Are CEOs Leaving on the Table? With David Boim

What we talked about.

In this episode of Sunny Ray's show, host Sunny Ray talks with David Boim about how much value CEOs leave on the table before a sale. David works with owners and CEOs through DSB and Associates and hosts the International Business Strategy Group, a community of more than 1,670 CEOs worldwide. He explains that many companies are not ready to be sold because their financials, operations, and succession plans are not in order. He shares examples of a manufacturer that raised its margins before selling for far more, a software company that brought in new leaders and later sold for a large cash price, and a professional services firm that grew quickly after rapid change. The conversation covers CEO blind spots, working backward from revenue goals to marketing KPIs, using AI to build standard operating procedures and test growth plans, why training needs testing, and how fear of change holds leaders back. David also warns about earn outs and a hacking scam disguised as an acquisition offer.

David Boim shows how unprepared financials, missing succession plans, and fear of change quietly cost CEOs millions before they sell.

The questions, and the answers.

What do you mean when you say CEOs are leaving value on the table?

Many owners want a liquidity event in a year or two but don't understand what their company is worth today. Buyers don't care about your blood, sweat, and tears. Most companies aren't prepared to be sold: financials aren't in order, there's no succession plan, and revenue opportunities are missed. I see that leakage all the time, and it directly lowers the price.

Why might a CEO not see that value?

I think CEOs put an artificial ceiling on their companies because the business depends too heavily on them. They become the single point of failure. They haven't invested in training or acquiring leaders, and they often don't take criticism well. I ask, what do we know for sure? If you could do it, it would already be done.

Where should a CEO look first for what they're missing?

If you haven't figured out what's missing, you need outside help identifying it. We run what we call an operational x-ray. In about a week we examine operations, find where leakage is hurting the financials, and build a plan to fix it. People inside for years only know your company, so you need an outside view, and someone who will help do the work.

How are you using AI to help CEOs, for example with standard operating procedures?

Many people use AI as an echo chamber, and I'd say don't do that. A buyer will expect standard operating procedures for each department, and AI is great for building them. I also tell CEOs to feed their company information and website into an AI tool, then ask what it takes to grow from X to Z, including marketing investment.

What questions should CEOs be asking their team?

First, ask openly for feedback on where the company can improve. Then look at ongoing training. Most organizations I know don't test, and training without testing is just orientation. Testing shows whether people know their job and how good your training is. If everyone does poorly, either hiring or training failed. Training also needs to be interactive, not one way.

What tends to stop leaders from acting on what they find?

Fear of change. After 35 years in venture capital and equity investment work and 17 turnarounds, I see three groups. About 70% resist change, about 25% embrace it, and about 5% live change. At one professional services company, changes in the first 30 days took utilization from 55% to 85% and billing from 40 to 65 million.

When should a CEO bring in an outside perspective?

When you've hit a plateau and don't know what's next, when competitors grow faster, or when you're losing money. It's even more critical if you plan to exit in two to three years. Without a succession plan and documented procedures, a buyer may impose a massive earn out, so you're still working for your payout instead of cashing out.