Private Equity Rollovers: How to Sell Your Company Twice
Most founders think of selling their business as a one-time event. But many of the biggest exits happen when you sell twice, to the same buyer.
How? Through an equity rollover structure, you sell a majority stake to take cash off the table now, stay on to grow the business with your new investment partner, and earn a second, often larger payday when the company sells again.
For founders running $10M–$30M in revenue with $1M+ EBITDA, this model turns a single transaction into a wealth-building strategy, one that rewards both the years you've already invested and the next few you'll spend scaling smarter.
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Real Example: Turning One Exit into Two
Imagine your company generates $3M EBITDA and sells for a 5x multiple: a $15M valuation.
You sell 70% for $10.5M in cash and keep 30% ($4.5M on paper).
With your PE partner’s backing, you expand into new markets, professionalize operations, and complete add-on acquisitions. EBITDA doubles to $6M within four years.
At the next exit, still at a conservative 5x multiple, the company sells for $30M.
Your 30% rollover now pays $9M. This is often referred to as ‘two bites of an apple’.
Total founder proceeds: $19.5M - almost double what a full sale upfront would have delivered.
Why This Strategy Works
The Deal Mechanics: What Really Drives the Outcome
Selling twice only works if the deal is structured right. That means understanding liquidation preferences, waterfalls, and rollover equity—the levers that determine how proceeds flow at each exit.
Liquidation Preferences: Who Gets Paid First
A liquidation preference defines how investors recoup their money before profits are shared.
A 1x non-participating preference means the investor gets their initial investment back before proceeds are split. A 2x or participating preference lets them take double—or keep participating after their return.
Example: Founder vs. Investor Outcome
Two deals with identical valuations can yield dramatically different outcomes.
Always model preferences before signing the LOI—your lawyer can’t fix bad economics after the fact.
The Waterfall: How Proceeds Actually Flow
When the company sells again, the waterfall determines who gets what. It’s the payout hierarchy behind every second exit.
Why it matters: Waterfalls decide your real payout on the second sale. A small difference in preference or carry can swing millions.
Common Rollover Structures
Quick Founder Self-Assessment
✅ Your business earns $1M+ EBITDA
✅ You still have 2–5 years of energy left to grow
✅ You’ve hit a ceiling without capital or infrastructure
✅ You’d like liquidity now and upside later
✅ You’re open to partnership and shared control
If that sounds like you, a private equity rollover may be the best way to maximize what you’ve built.
FAQs: Selling Twice Explained
What is a private equity rollover?
It’s when you sell most of your company but keep equity in the new entity—allowing you to profit again when the next sale occurs.
How much equity do founders usually keep?
Typically 20–40%, depending on the company’s size, growth outlook, and investor structure.
How long do founders stay after selling?
Usually 1–5 years, depending on goals and deal terms.
What’s the biggest risk?
Rollover equity only pays off if the company grows. Choosing the right partner is critical.
How can I negotiate fair terms?
Hire an M&A advisor who models liquidation preferences, waterfall outcomes, and carry splits before signing.
Can I defer taxes on the rollover portion?
Often yes, especially when equity is rolled into a new entity. Always confirm with a tax advisor early.
Key Takeaways
Normalize EBITDA with clear documentation.
Use multiples as a guide, not a rule.
Validate value with comps and payback math.
Structure deals to balance risk.
Bring in professionals for complex or leveraged transactions.
Final Thoughts
A private equity rollover lets you enjoy the best of both worlds—liquidity today and compounding wealth tomorrow.
By selling once and structuring your deal for a second payout, you convert your business from a single asset into a strategic wealth engine.
At Breakwater M&A, we help founders design these deals every day—balancing valuation, structure, and long-term payoff.
📘 Download our Million Dollar Exit Guide to see real deal models, or schedule a confidential call to learn how to sell your company twice.
Recommended Reading
For more resources on evaluating offers and exit strategies, explore these related Breakwater articles:
Should You Sell Your Business to Private Equity?
How private equity structures deals and when selling to PE beats a strategic buyer for founder outcomes.
What to Do If You Receive an Unsolicited Offer for Your Business
Practical steps to evaluate, respond to, and create leverage around an unsolicited offer without losing control.
How to Sell a Business in Canada: Step-by-Step Guide for 2025
A Canada‑specific, step‑by‑step playbook covering timelines, advisors, and legal nuances.
Can You Sell an Unprofitable Company? (How to Avoid a Distressed Exit)
Options for owners with negative or thin profits and how to avoid distressed‑sale traps.
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