Ah, the classic dilemma of selling out completely versus staying in the game with a smaller stake! Let's break it down:

  • Selling 100%: When an entrepreneur sells their entire company, they're cashing out completely. They walk away with the full sale proceeds and wash their hands of the business. It's a clean exit with no strings attached. They can go sip cocktails on a beach or jump into a new venture without looking back.

  • Selling 80% and Reacquiring 20% via an LBO: Now, this is where it gets interesting. If an entrepreneur sells the majority but then reacquires a minority stake through a Leveraged Buyout (LBO) orchestrated by another party, they're still in the game, albeit not in the captain's chair. Here's what happens:

    • They get a chunk of change for the 80% they sell, which is nice.
    • By holding onto a 20% stake, they could benefit from any future growth or upside the new owners create with their financial wizardry and strategic moves.
    • However, they're also taking on risk. If the LBO piles on debt and things go south, their 20% could shrink in value or, in a worst-case scenario, become worthless.
    • They might also have to deal with new bosses (the majority owners), which could mean less control and possibly clashing visions for the company's future.

So, it's a trade-off between total freedom and potential future gains (with a side of risk). It's like deciding whether to eat the whole chocolate bar now or save a few squares for later, hoping they'll taste even sweeter.

Sources: Overview of Leveraged Finance, Overview of Leveraged Finance, Differences between Co-invest and Secondaries?, SaaS LBO, Leveraged Buy Outs in RE?

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Considering that most LBOs are done by sponsors and a founder is typically not working at a fund at the same time they are running a business - you don’t see a founder sell 80%, then later re acquire 20% which would make their ownership then 40%? That’s just not a realistic transaction.


What you will see though is that a founder, assuming in the rare case they are the only shareholder - they could sell 80% of the business to cash out, then roll forward 20% of the equity that they owned into the new entity. This would require the founder to stay on during the duration of the hold, and they would only be able to monetize if and when the sponsor sold the asset again at a higher value. They would then get 20% of the incremental equity gained during the period and the sponsor would retain the 80%. Still, it’s extremely unlikely a fund is allowing a founder to roll more than 1-5% forward due to economics. They still have to make the IRR work in order to justify the transaction in the first place.

 

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