Successful Exits: Real, Fake, and How to tell the Difference

For those of us in the startup world, the term exit has a specific meaning. It’s the endpoint of a founder’s involvement with a startup. A successful exit means that the founder made a bunch of money right? The old adage on startup exits used to be that exits were measured this way:

Small: You made enough to change you car
Medium: You made enough to change your house
Large: You made enough to change your life

In public, we see exits measured by total deal value, and we celebrate the unicorns, and the 9-figure exits – but how often are we able to see what really happened from a founder perspective? Actual founder outcomes are important to understand for those in this business – and it’s important to understand opportunity cost and how to calculate Return on Investment for a founder. Here’s a rundown on “fake” exits, secretly unsuccessful exits, and a take on how to measure a founder’s actual ROI in an exit.

Fake Exits

1. Private Equity majority ownership stakes: You see the press release, the shining coverage – xyz startup sells for $300 million, or $1.2 billion! Dig deeper, and it turns out that a PE firm has purchased majority ownership from the VCs backing a startup. While founders may receive some cash liquidity, they have to stay on to deliver the next phase of growth. Founders “exiting” in this way in 2021 may find that their stake is now worth much less than the announcement price tag, as late-stage startup valuations have shrunk dramatically.

2. Stock acquisition by a larger private company: everyone gets stock in the rocket ship right? I founded a company in 1999 that was acquired by a pre-IPO Intralinks for $1.2M on paper in 2000 – my shares were worth $350 after the crash (I was 22 and it was a great education). This kind of exit could go really well too – but it’s not technically an exit, as you are just trading one illiquid asset for another, and you must keep up the fight until a future exit event.

3. Down Exit (below VC preference): When VCs and other early investors invest in your company, they often buy preferred shares, which come with a liquidation preference. If the company is acquired for less than this valuation, then the investors receive everything. Companies that raised at extremely high valuations in 2021 may find themselves in this situation. Consider a company that raises $300M on a 1.2B valuation in 2021, and then falls 80% in value in 2022 (in line with its public saas peers). If the company is forced to exit at the lower valuation, founders could end up with nothing despite having built a one-time unicorn!

This has happened before.

How to Calculate Founder ROI

Let’s say you get past all the traps, and you’re on your way to a successful exit. What was the return on investment of all the blood, sweat, and tears in the end?

Consider my situation. I was saving $150k per year (working FT + fractionally) prior to starting HiddenLevers. It took 3.5 years for my income from the business to equal this opportunity cost. It took almost a decade to build HL and sell from there, a time in which the S&P 500 roughly tripled in value. If I had kept working corporate jobs, I would have invested 525k, and that might have tripled to around $1.6M by the time of the HL exit. So I can compare that amount against my exit as one reference point – if I hadn’t exceeded that amount, I would have been better off keeping my day job! [1]

You can calculate your rate of return by dividing total exit by the initial sweat equity investment amount (in this case 525k), and then annualizing the result. If it’s greater than 10% you beat the long term performance of the equity markets.

It’s also worth noting that had I kept my day job, I’m sure that my career would have advanced, further increasing my opportunity cost. Now, none of this matters if you weren’t saving a dime to begin with, or if your quality of life doesn’t suffer as a result of starting a company. But most founders have other options, so it’s worth making the comparison to understand whether the numbers add up. And of course, this also provides insight into another thing – just how much you value being able to leave the grind and build something for yourself!

[1] We use net savings and not top line income, because we need to know how much capital you would have been able to invest in the alternate case, where you never left your day job. Net savings is a reasonable approximation of that – but if you’re the sort of person whose lifestyle expands to absorb additional income, then a comparison of after-tax salaries in both cases might be more relevant.

[2] To really calculate this accurately, you could create a spreadsheet that calculates opportunity cost year by year, but here I’ve just used rough averages to illustrate the point.

P.S. If you got this far – one way I got to my exit was by running super efficiently, and I’m proud of HiddenLevers’ 53% EBITDA margin at exit. Fractional developers helped me to get to that level of profitability – see how I can help you do the same via

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