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.
Two founders rejected a $20M acquisition offer they felt was too low. After successfully pivoting their business during the pandemic, they returned to the same buyer and received a doubled offer of $40M with better terms. This shows how patience and focusing on business performance can dramatically improve an exit outcome.
Marshall Haas sold a controlling stake in his company but retained significant equity. His goal was not just a cash payout, but to create a structure that provided ongoing cash flow, a continued advisory role, and a way to avoid the boredom and financial anxiety that often follows a complete, all-or-nothing exit.
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.
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.
Before selling two-thirds of his company Gym Launch for $31M, Alex Hormozi had already taken $42M in distributions. This proves that for highly profitable businesses, the wealth generated from ongoing operations can be far more significant than the headline exit price, flipping the script on the importance of the final sale.