Big Exit, Bigger Regret? How to Sell Without Leaving Millions on the Table

If there’s one theme I hear repeatedly from business owners who’ve sold their company, it’s regret. According to the Exit Planning Institute (EPI), 76% of business owners regret selling their businesses within a year of the sale.

As far as my experience goes, here’s the thing. The regret is not for selling, but for how they sold.

It’s not uncommon for founders to miss out on millions due to poor exit strategies, misjudging market needs, and making poor partnership and equity decisions that can lead to costly mistakes. Additionally, they may fail to plan appropriately for potential acquisitions or sales, resulting in lost value.

Someone who understands this well is Chad Morissette, an entrepreneur-turned-M&A-advisor who has helped hundreds of entrepreneurs achieve successful exits. In fact, our Lifestyle Investor Mastermind members rated his session one of the best they’ve ever had. And, for good reason. He has been on both sides of the table: both as a founder who sold multiple companies and as an advisor guiding others through high-stakes transactions.

So, let’s unpack some of Chad’s biggest lessons for anyone considering a future exit — and doing so without regret.

Why Most Sellers Leave Money on the Table

The first —and perhaps most significant —mistake founders make is failing to cast a wide net.

In the U.S. alone, there are more than 5,000 private equity firms. Combined with strategic buyers, family offices, roll-up groups, and international acquirers, the pool of potential buyers grows exponentially.

Despite this, many business owners present their company to only a few potential buyers. They don’t run a broad process. They don’t create competition. This means they’re leaving a lot of capital and dry powder on the table, as Chad explains.

In other words, unless you have multiple groups competing for your business, you will never get maximum value.

Who Buys Companies in the Lower Middle Market

Chad’s firm specializes in the “lower middle market.” These are companies that generate $5 million to $50 million in revenue annually and earn between $1 million and $10 million in EBITDA.

Compared to ultra-high-end deals you read about in the news, it’s a huge market. There’s just one problem: this market is underserved. Many advisors focus only on exits of $75 million to $100 million or more. Chad’s team assists entrepreneurs who might otherwise go unnoticed.

From technology to franchising, biotechnology to business services, they’ve represented founders in a wide range of industries. Because the fundamentals of preparing, positioning, and selling a business are universal, the process works across industries.

Why Experience on the Sell-Side Matters

Chad’s firm stands out in that every advisor on his team has been a founder themselves, which is one reason our Mastermind members resonated with his talk.

Not just founders, but entrepreneurs who’ve sold their companies as well.

Why is this important? It matters because selling a business is one of the most high-stakes and emotionally charged transactions you will ever undertake. When you’re burned out, sued, or worried about making payroll, it helps to sit across from someone who has been there.

As Chad puts it, “We’re not just talking theory — we’ve lived it.” It’s that credibility that builds trust. For founders, it facilitates taking advice, following the process, and ultimately achieving a successful exit.

Always Be Ready to Sell

Regardless of whether you’re actively planning to sell, you should always prepare to do so. Why? Opportunities often appear out of the blue.

Sometimes, acquisitions come knocking on your door when you least expect them. A business without prepared financials, unreliable systems, or undocumented teams is likely to miss out on this opportunity or accept a lower price.

By thinking about the end in mind, you can change the way you run your business. You’re forced to build systems, strengthen operations, and document processes that make the company less dependent on you. Ironically, this makes running more enjoyable, whether or not you sell.

The Two Buckets of Exit Readiness to avoid regret

As Chad explains, there are two buckets of readiness: personal and business.

1. Personal readiness.

• Would you like to sell because you’re truly ready or because you had a bad week?
• What’s your “why”? Is it retirement, boredom, burnout, or the desire to try something new?
• Is your estate and tax planning structured in such a way that it is tax-efficient?

This is a step that many founders skip. Often, they move directly to financials without considering whether they are emotionally and strategically ready to exit.

2. Business readiness.

• Do you think your company would pass a due diligence stress test?
• Are your operations modern and scalable?
• Is your HR, marketing, and technology strategy appealing to buyers, or is it outdated?

Founders often assume that profit alone equals value. Buyers, however, look beyond earnings. Their focus is on culture, systems, customer diversity, intellectual property, and growth opportunities.

Valuation: The Tough Love Conversation

Another common mistake? Founders overestimate their business’s value.

It’s not unusual for owners to be off by millions, if not tens of millions. A good advisor serves as a reality check in situations like these.

In the end, the price is determined by the market. Valuation is both an art and a science. In addition to revenue multiples, it’s important to have a strategic fit, synergies, and a compelling story to tell.

But here’s the kicker: even if you sell for a significant number, you need to ask, “What do I actually net?” Taxes, fees, and earn-outs can dramatically affect your take-home pay.

Because of this, Chad insists on running a net proceeds analysis. Using it, you can determine whether your long-term wealth goals will be met by how much money you actually receive into your account.

Why Three Years Out Is the Sweet Spot

To maximize your exit, start planning one to three years in advance.

It is okay to start earlier. And yes, deals can come together faster. However, a one- to three-year window provides enough time for:

• Clean up your finances.
• Shore up the operations.
• Strengthen the management team.
• Modernize marketing and tech.
• Tell a compelling story about your growth.

In addition, it allows you to structure the sale tax-efficiently. If you wait until the last minute, you will almost always end up with a lower valuation and more stress.

Diversification: The Risk of Overconcentration

Diversification is one of the most important lessons I teach in the Lifestyle Investor community. However, many entrepreneurs have their businesses tied up to 70%, 80%, or even 90% of their net worth.

That’s dangerous. If the business falters, everything could collapse.

This is why selling, even partially, isn’t just about cashing out. Investing in a diversified portfolio can fund your lifestyle for decades by de-risking, protecting your family, and reallocating capital.

Attracting More Buyers, Driving Higher Offers

Finally, let’s revisit the regret we began with: too few buyers.

For the best possible exit, you need multiple buyers. As a result of that competition, you get a better price, better terms, and more leverage.

Today’s buyer pool is broader than ever before. Besides private equity and strategics, you’ve got family offices, venture-backed groups, roll-ups, and international buyers. However, many founders and advisors do not explore the full range of options.

The result? Missed opportunities and lower valuations.

Final Thoughts on avoiding selling regret

One of the biggest financial and emotional events in your life is selling your business. When you do it right, you preserve your legacy, secure family wealth, and create new opportunities. If you do it wrong, you’ll regret it, knowing you’ve wasted millions.

The biggest lesson? Prepare now. If you don’t think you’ll sell tomorrow, act as if you will. Put in place the systems, get your financial house in order, and learn the playbook.

By doing so, you won’t be one of the many founders who wish they’d taken a different path when the right opportunity arises.

Key Takeaways

• Cast a wide net. You’re more likely to maximize value if there are more buyers at the table.
• Always be ready. Your business should be run as if it might sell tomorrow.
• Separate personal vs. business readiness. As you prepare operations, reflect on your “why.”
• Get real on valuation. Prices are set by the market, not by your emotions.
• Plan one to three years out. In that window of time, you can optimize and structure.
• De-risk your wealth. It’s not advisable to have 80–90% of your net worth tied to one business.
• Tell a better story. Your business should be positioned not just on its financials, but also on its growth potential.

Featured Image Credit: RDNE Stock project; Pexels: Thank you!