After their main exit, two founders received a secondary payout structured as a promissory note. This 'bonus' was taxed as earned income at a ~50% rate, not as capital gains (~25-30%). This structuring detail cut their net proceeds in half, highlighting a critical and non-obvious tax trap in complex M&A deals.
Related Insights
Successful founders prioritize cash upfront over potentially larger payouts from complex earnouts. Earnouts often underperform because founders lose control of the business's future performance, leading to dissatisfaction despite a higher on-paper valuation.
The most powerful incentive for increasing employee ownership is to make founder exits to their employees tax-free. This aligns financial self-interest with a social good, making it more profitable for a founder to sell to their team than to private equity.
Founder Aaron Galperin moved from high-tax California to no-tax Texas specifically to avoid state income tax on his company's sale. This pre-exit relocation is a crucial, often overlooked financial strategy that significantly increases a founder's net take-home pay from a liquidity event.
Founders should be wary of earn-out clauses. Acquirers can impose layers of pointless processes and overhead costs, tanking the profitability of a successful business and making it impossible for the founder to ever receive their earn-out payment.
The founder's partnership allowed him to build a company without shouldering the initial financial risk. This "halfsies on risk" structure meant he never had true control or ownership, ultimately capping his upside and leaving him with nothing. To get the full reward, you must take the full risk.
A $33M exit sounds huge, but Scott Galloway only took home $2-3M. This was because he owned just 20-30% of the company and had to split proceeds with his ex-wife. It's a powerful reminder that founder equity and personal circumstances, not the sale price, determine the actual take-home amount.
The number of founders taking secondary liquidity after their seed round is twice as high as the 2021 peak. While this de-risks the journey for founders, there is almost no parallel liquidity offered to early employees, creating a growing divide in early-stage risk and reward.
Logan and Jake Paul's accelerator offers $125K for 7% equity, but structures it as a $25K SAFE plus a $100K priced round. This unnecessarily complex structure forces founders to incur immediate legal costs for the priced round, reducing their net investment compared to a simpler, single SAFE.
Post-exit financial planning is too late. Jacqueline Johnson learned from her banker that founders should be interviewing and establishing relationships with firms like Goldman Sachs or UBS *during* the sale process to create a full strategy for taxes and investments beforehand.
To retain founders who've already cashed out, use a dual incentive. Offer rollover equity in the new parent company for long-term alignment ('a second bite at the apple'), and a cash earn-out tied to short-term growth targets. This financial structure is crucial when managing wealthy, independent operators who don't need the job.