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PE Rollover / Second Bite Simulator

Model a PE-backed rollover scenario with a second exit 3-5 years later.

From Chapter 12: PE Ownership Structures

In a PE-backed recapitalization, you keep equity in the company alongside the private equity buyer. You get significant cash at close but also keep 'a second bite of the apple' when the company exits in five to seven years. This structure is common with add-on acquisitions and situations where founders want to retain upside while monetizing some value.

The value of rollover equity depends on how much you keep, what percentage of the company it represents, and what multiple the company trades at on exit. A 20% rollover stake in a company that grows from 5x to 8x EBITDA could be worth significantly more than your initial exit proceeds. But modeling this correctly requires understanding dilution, the growth path, and realistic exit scenarios.

First Sale Parameters

Second Sale Parameters

Three Scenarios

Bull Case (1.5x growth)

First Bite $0
Second EV $0
Equity Value $0
Second Bite (after tax) $0
Total Proceeds $0

Base Case (1.0x)

First Bite $0
Second EV $0
Equity Value $0
Second Bite (after tax) $0
Total Proceeds $0

Bear Case (0.5x shrink)

First Bite $0
Second EV $0
Equity Value $0
Second Bite (after tax) $0
Total Proceeds $0

How PE Rollovers Work

The deal structure: buyer pays you X in cash for partial company stake and commits to a growth plan. You keep Y% equity. In five years, the company exits at a higher multiple. Your Y% stake is worth more. You receive additional proceeds. This gives you leverage to a growth scenario without bearing all the risk of private ownership.

Calculating Rollover Equity Value

Start with your expected stake percentage post-close. Model the company EBITDA growth over five years based on buyer's growth plan. Apply a reasonable exit multiple. Calculate your stake value at exit. Discount back to today using a risk-adjusted rate (20-30% for growth equity risk). The present value of your rollover is what that equity is worth today.

Managing Rollover Risk

Rollover equity is illiquid and depends on future performance. Negotiate tag-along rights so you can sell your stake at the same time other shareholders do. Get clear documentation of your ownership percentage to prevent dilution. Understand any clawback provisions if the company underperforms. Structure your stake for tax efficiency.

Common Mistakes

Overestimating future growth

PE buyers are ambitious about growth targets. Reality is harder. Use conservative growth projections, not the buyer's aggressive deck. A 5x to 8x exit is optimistic. Plan for 5x to 6x unless the buyer has a clear track record.

Underestimating dilution

Your rollover percentage can be diluted by future financing rounds or add-on acquisitions. Negotiate anti-dilution language and tag-along rights to protect your stake.

Ignoring liquidity constraints

Rollover equity is illiquid for 5-7 years. Make sure you can afford to keep this money in the deal without needing access. Don't roll more than you can afford to lose.

Frequently Asked Questions

What does 'second bite of the apple' mean?
It means you get paid twice: once when the PE firm buys (first bite) and again when the company exits and your equity stake is converted to cash (second bite). The second bite gives you leverage to growth upside beyond your initial exit proceeds.
How much should I keep in a rollover?
This depends on your confidence in the buyer's growth plan and your risk tolerance. Common rollover percentages are 5-20%. Keep more if you believe in the buyer, less if you want to monetize and reduce risk. Align your rollover with your personal financial situation and goals.
Can my rollover equity get diluted?
Yes. Future fundraising, employee option grants, or add-on acquisitions can dilute your percentage. Get explicit anti-dilution language and tag-along rights. Make sure your rollover stake is protected from dilution from new financing rounds.
What if the PE exit is delayed or value drops?
Delayed exits extend your holding period and increase risk. Value drops hurt your exit proceeds. These are rollover risks. Negotiate governance rights to stay informed about the company's path. Build flexibility into your personal financial plan since rollover proceeds are unpredictable.