Double Dip Your Exit to Generational Wealth
- Dr Allen Nazeri DDS MBA
- Jan 30
- 6 min read
Why Smart Business Owners Are Choosing a Second Bite of the Apple Instead of a One-Time Exit
For most business owners, their company is not just a source of income—it is their single largest financial asset, the product of decades of work, sacrifice, and reinvestment. Yet despite this reality, many founders still approach an exit as a binary decision: either sell everything or do nothing at all.
That approach is increasingly outdated—and often dangerous.
In today’s market, the most experienced founders and families are embracing a more nuanced, strategic approach known as Double Dipping. Rather than selling 100% of their company in a single transaction, they pursue a partial exit, taking meaningful liquidity off the table while retaining equity for a second, often more lucrative exit down the road.
Double Dipping is not about greed or hesitation. It is about risk management, value amplification, and long-term wealth creation. When executed properly, it transforms an exit from a one-time payday into a multi-stage strategy designed to protect what you’ve built while positioning your family for generational wealth.
What Does “Double Dipping” Really Mean in an Exit?
In its simplest form, Double Dipping refers to selling a portion of your business—typically a majority or significant minority stake—while retaining meaningful ownership to participate in future upside.
In practice, this often looks like:
Selling 51%–80% of the company to a strategic buyer or private equity firm
Retaining 20%–49% equity through rollover or reinvestment
Partnering with capital that brings infrastructure, systems, and growth resources
Positioning the business for a second exit in three to seven years
The first transaction provides liquidity and de-risking. The second delivers wealth creation at scale.
This approach allows owners to step off the tightrope of “all-or-nothing” decision-making and instead operate from a position of strength, flexibility, and foresight.
The Power of Owning a Smaller Piece of a Much Larger Pie
One of the most common objections founders raise when discussing a partial exit is dilution. After all, many owners spent years building 100% ownership and emotional control over their business. The idea of owning less can feel counterintuitive—even threatening.
But ownership percentage alone is meaningless without context.
Owning 100% of a $25 million company may feel emotionally satisfying, but owning 25% of a $200 million company is financially transformative. The difference lies not just in valuation, but in scale, systems, and sustainability.
Strategic and institutional partners bring:
Professionalized management and reporting
Access to capital for acquisitions and expansion
Sophisticated pricing, contracting, and compliance infrastructure
Talent recruitment and incentive alignment
Credibility with lenders, payers, and counterparties
These elements allow the business to grow faster—and often more profitably—than it ever could under founder-only ownership.
Double Dipping is not about giving something up. It is about multiplying what remains.
Why Waiting for the “Perfect Exit” Can Be a Costly Mistake
Many owners delay exploring exit options because they believe the business will be worth more “next year.” Sometimes that is true. Often, it is not.
Time introduces uncertainty, and uncertainty introduces risk. Markets shift. Technology evolves. Regulations change. Personal circumstances intervene. Buyers price all of this into valuation—whether founders like it or not.
This is where too many business owners encounter the 5 Ds, often with devastating consequences.
The 5 Ds That Quietly Destroy Business Value
Every seasoned M&A advisor has seen strong businesses lose value—not because they were poorly run, but because owners waited too long.
Death is the most obvious and tragic. Without a proactive exit or succession plan, families are often forced into rushed or discounted sales during emotionally charged moments.
Disability can remove a key operator overnight. If the founder is integral to revenue, operations, or relationships, buyers immediately apply discounts for key-person risk.
Divorce frequently creates forced liquidity events, partner disputes, or shareholder misalignment. Deals stall, litigation erupts, and value erodes.
Disagreement, particularly among partners or family members, can paralyze growth. Buyers are wary of fractured ownership groups and will either walk away or materially reduce offers.
Disruption may be the most underestimated risk of all. Artificial intelligence, automation, reimbursement shifts, regulatory changes, and new competitors can compress margins far faster than most owners anticipate.
The uncomfortable truth is this: no business is immune.
Double Dipping allows owners to get ahead of these risks rather than react to them.
How Double Dipping De-Risks Without Walking Away
A partial exit does not mean abandoning the business or its mission. In fact, it often allows founders to stay involved in the areas where they add the most value—strategy, relationships, vision—while shedding operational burdens.
The first liquidity event accomplishes something critically important: it decouples personal financial security from business performance.
Once that pressure is removed, founders make better decisions. Growth becomes intentional rather than desperate. Risk-taking becomes strategic rather than existential.
Most importantly, owners no longer have all of their net worth tied to a single asset exposed to the 5 Ds.
The Two Bites of the Apple: Liquidity First, Wealth Second
The first exit in a Double Dipping strategy is about stability and protection. Owners often use this capital to diversify investments, address estate planning, support family needs, or simply gain peace of mind.
The second exit is where true wealth multiplication occurs.
With stronger systems, higher EBITDA quality, expanded scale, and often multiple acquisitions completed, the second sale is frequently priced at meaningfully higher valuation multiples. In many cases, the retained equity alone is worth as much—or more—than what the founder received in the first transaction.
This is how exits evolve from “life-changing” to legacy-defining.
Who Should Seriously Consider a Double Dipping Strategy?
Double Dipping is not for every owner, but it is particularly effective for founders who:
Have built a business with at least $2 million in EBITDA or strong momentum
Are still energized and want to remain involved post-transaction
Operate in scalable industries such as healthcare, services, manufacturing, technology, or EMRA
Want liquidity without fully stepping away
Care about long-term value, employees, and legacy
Mid-career entrepreneurs, family-owned businesses, and founder-led platforms are often ideal candidates.
Common Misunderstandings That Hold Owners Back
Many founders mistakenly believe that buyers only want full control. In reality, most private equity groups prefer owners to retain equity. Alignment matters.
Others fear loss of control, when governance, voting rights, and decision-making authority are all negotiable when properly structured.
Perhaps the most damaging misconception is that “it’s too early to talk about an exit.” In truth, the best exits are planned years before the transaction—not months.
Why Execution and Advice Matter More Than Ever
Double Dipping is not a simple brokerage transaction. It requires sophisticated positioning, buyer selection, valuation engineering, and deal structuring. The wrong partner—or the wrong advisor—can eliminate the very upside the strategy is designed to capture.
Founders who attempt partial exits without experienced guidance often discover too late that they retained the wrong percentage, accepted restrictive terms, or aligned with capital that limits future optionality.
The goal is not just to sell—it is to sell intelligently.
Final Thought: One Exit Is an Event. Two Exits Are a Strategy.
Selling a business once can change your life.Selling it twice can change your family’s future.
Double Dipping is not about hesitation or indecision. It is about recognizing that wealth creation does not have to end at the closing table.
For owners who want liquidity, protection, upside, and legacy, the question is no longer whether to sell—but how.
And increasingly, the smartest answer is this:
Double Dip your exit.
Dr. Allen Nazeri, aka "Dr. Allen," boasts over 35 years of global experience as an entrepreneur. He is the Managing Director at American Healthcare Capital and Managing Partner at PRIME exits. Dr. Allen provides strategic growth consulting to leadership teams of both privately held and publicly listed companies, ensuring their preparedness for successful exits. Dr. Allen holds a Dental Degree from Creighton University and an MBA in M&A and Investment Banking from the University of Bedfordshire. He is also a Master Certified Intermediary (M&AMI), a prestigious designation awarded to a select group of M&A advisors who have demonstrated exceptional negotiation skills and successfully led large, complex middle-market transactions to close.
Dr. Allen is the author of "Value Engineering: Strategies to 10X the Value of Your Clinic and Dominate the Market!" and the brand new book "Selling Your Healthcare Company at a Premium". Dr. Allen offers a free valuation to business owners ready for a partial or complete exit strategy. Dr. Allen collaborates with strategic buyers, private equity firms, and institutional investors, taking direct accountability for the annual successful sell-side representation of over $1 Billion in enterprise value across healthcare, Engineering, Manufacturing, Robotics and Automation.
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