Its’ Not Fortune Cookie Wisdom…Its’Just Logic

Bridging the Wealth Gap and Value Gap: A Small Business Owner’s Guide to Retirement and Selling Smart

By Michael Shea March 11, 2025

If you’ve ever watched Moneyball—and if you haven’t, go check out this clip here—you’ll remember the scene where Billy Beane, played by Brad Pitt, is trying to rebuild the Oakland A’s on a shoestring budget. He’s sitting across from his scouts, who are stuck in the past, rattling off the same old metrics for success: batting averages, home runs, the “look” of a player. Then Peter Brand, the numbers guy, steps in and flips the script. “We’re not selling jeans here,” he says. “We’re looking for runs—wins. That’s it.” It’s a lightbulb moment: value isn’t always what it seems on the surface.

For small business owners, that scene hits home in a big way. You’ve spent years—maybe decades—pouring your heart into your company. It’s your baby, your legacy. But when it comes time to think about retirement or selling that business, you’re not just facing a wealth gap (the difference between what you have and what you need to retire comfortably). You’re also staring down a value gap (the difference between what your business is worth today and what it could be worth with the right strategy). If you want to step up to the plate and knock it out of the park, you’ve got to address both. Here’s how.

The Wealth Gap: Your Personal Moneyball Moment

Let’s start with the wealth gap. Most small business owners I talk to have a fuzzy picture of what “enough” looks like for retirement. You might have a number in your head—say, $2 million—but does that account for inflation, healthcare costs, or the fact that you might live to 95? Too often, owners assume their business will be the golden goose that funds their golden years. But here’s the catch: if you don’t know your target, you’re swinging blind.

Think of it like Billy Beane’s A’s. He didn’t just need players—he needed runs. For you, it’s not just about having a business; it’s about having enough liquid wealth to sustain your lifestyle when the paychecks stop. Step one is getting crystal clear on your wealth gap. Sit down with a financial planner and run the numbers. How much do you need annually? How long will your savings need to last? Factor in Social Security, investments, and—crucially—the potential proceeds from selling your business. That’s your “runs” total. Without it, you’re guessing, and guessing doesn’t win games.

The Value Gap: Turning Your Business Into a Heavy Hitter

Now let’s talk about the value gap, because this is where Moneyball really shines. In that clip, Peter Brand points out that the traditional scouts are overvaluing flashy stats and undervaluing the unsexy stuff—like on-base percentage. Small business owners do the same thing. You might think your business is worth a fortune because of your loyal customers or your killer location. But buyers? They’re not buying your past hustle—they’re buying your future cash flow, your systems, your scalability. If your business relies on you to keep the lights on, its value takes a hit.

The value gap is the difference between what your business is worth today and what it could fetch if you optimized it. Maybe it’s $500,000 now, but with some tweaks—streamlined operations, a stronger management team, diversified revenue streams—it could be $1.5 million. That’s a million bucks you’re leaving on the table if you don’t act. Start by asking: What’s my on-base percentage? In other words, what’s driving real value? Dig into your financials. Look at your EBITDA (earnings before interest, taxes, depreciation, and amortization). Buyers love that stat. Then, get your house in order—document processes, reduce owner dependency, and build a business that runs without you. That’s how you close the value gap and turn your company into a heavy hitter.

The Playbook: Marrying Wealth and Value for the Win

Here’s where the rubber meets the road. To retire comfortably and cash out smart, you’ve got to marry these two gaps into one cohesive strategy. Let’s say your wealth gap analysis shows you need $3 million to retire, but your business is currently valued at $1 million. You’ve got a $2 million shortfall. Closing the value gap can get you partway there—maybe boosting your sale price to $2 million with three years of focused effort. The rest? That’s where personal savings, investments, or even a phased exit (like staying on as a consultant post-sale) come in.

Think of it like Billy Beane’s lineup. He didn’t just need one star player; he needed a team that collectively got on base and scored runs. You don’t just need a big sale; you need a plan that combines sale proceeds with other assets to hit your retirement number. Start early—five to ten years out if you can. Work with a business broker or valuation expert to benchmark your company’s worth today and map out growth. At the same time, tighten up your personal finances—max out retirement accounts, diversify investments, and cut unnecessary expenses. It’s not sexy, but it’s the unsexy stuff that wins.

The Bottom Line

Small business owners, you’re not selling jeans—or baseball cards. You’re selling a future: yours and your buyer’s. Addressing the wealth gap gives you clarity on what you need to walk away with. Tackling the value gap ensures you’ve got something worth selling. Together, they’re your ticket to a retirement that doesn’t leave you scrambling in the ninth inning.

So, channel your inner Billy Beane. Stop swinging at the obvious pitches and start playing the numbers game. Your business isn’t just your livelihood—it’s your Moneyball moment. Make it count.

For more on selling your business and exit planning in Tampa Contact Tampa Business Broker Michael Shea at 813-733-6245