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Most entrepreneurs spend years pouring their blood, sweat, and tears into building a business, yet very few prepare themselves for what happens once the deal is finalized.
In this episode of The Exit, host Steve McGarry sits down with Mark Miller, Managing Director of the Hilton Family Office and CEO of Hilton Tax & Wealth Advisors. With nearly four decades of financial services experience, Mark shares the tactical—and often overlooked—financial and emotional strategies required to maximize your company’s value and keep what you earn.
What is Your Business Actually Worth?
Want a quick estimate of your company’s value before diving into exit planning? Use our Free Valuation Calculator to get an immediate estimate of what your business could fetch on the market.
The Danger of a “Generalist” Team
One of the most eye-opening revelations from Mark’s experience is how often multi-million dollar exits go wrong simply due to the wrong advisory team.
“Nine times out of ten, people come to us after an exit and they’ve done it incorrectly,” Mark warns. The primary culprit? Relying on everyday bookkeepers, standard CPAs, or general corporate attorneys who lack specialized transactional expertise.
Mark recalls a powerful example of a business owner selling a massive collision center network in Atlanta. The founder was brilliant, but he trusted his long-term CPA to handle the sale. Because that CPA only had experience in standard compliance and tax returns, they lacked the specialized knowledge required to structure a complex exit. The result? Nearly 40% to 50% of the windfall vanished into taxes.
When navigating an exit, you aren’t just looking for standard legal protection; you need “brain surgeons”—specialists who know how to structure deals to minimize tax burdens, occasionally bringing them down to near zero.
When is the Right Time to Exit?
While there is no universally perfect timeframe for maturity—an IT company might explode and exit in three years , while a construction firm might take 20 years to become saleable —there is a perfect time to start planning.
According to Mark, you should begin building your advisory team and putting exit frameworks into place at least one to two years in advance. A comprehensive exit team should ideally feature:
- A specialized transaction CPA
- An M&A attorney
- An experienced financial advisor / wealth manager
- An insurance professional
- An administrative lead to coordinate communication
Without unified communication across this team, critical planning gaps inevitably form, leading to costly post-closing surprises.
Two Levers to Drive Higher Multiples
If you want to intentionally drive up your business valuation before talking to buyers, Mark highlights two essential focuses:
1. Systematize and Memorialize Your Processes
It’s surprisingly common to see $100 million companies operating with zero documented processes. If your operations solely live in the heads of your employees or are tied completely to your personal brand, the asset is incredibly difficult to transfer. Buyers pay a premium for turnkey operations. Spend the money to outsource or hire someone to map out, systemize, and memorialize every core process.
2. Diversify Your Marketing Stools
Sales drive companies, but diverse marketing strategies drive value. Relying on a single acquisition channel introduces massive risk to a buyer. By expanding your marketing channels and adding “new legs to the stool,” you accelerate revenue growth while making the business structurally safer and more attractive to prospective buyers.
The Emotional Shock of the Winfall
An exit isn’t just a financial transaction; it’s a profound lifestyle shift. Founders who have spent 20 or 30 years grinding 80 hours a week suddenly face an abrupt stop.
“Strangely enough, we end up becoming psychologists in many ways,” Mark notes. Founders often miscalculate how their post-tax lump sum aligns with their long-term lifestyle run rate. When the reality of the tax hit sinks in, or the shock of sudden retirement becomes too overwhelming, many find themselves trapped by strict non-compete clauses when they inevitably try to jump right back into the industry. Preparing emotionally for life after the business is just as critical as preparing the balance sheet.
Bringing Elite Strategies to Main Street
Through Hilton Tax & Wealth Advisors, Mark and his partner Brad Hilton (grandson of Hilton Hotels founder Conrad Hilton) are taking the advanced, ultra-high-net-worth wealth preservation frameworks utilized by massive family offices and making them accessible to everyday business owners looking to protect their legacies.
