What's Your Deal? · Oct 21, 2026 · 46m · 38m saved
With Mike Grossman, Author of Failure Is an Option, previously CEO of six venture-funded companies
One US startup spent about 18 months trying to go public, twice, and failed both times. A strategic buyer then paid meaningfully more for it than either IPO would have raised.
Mike Grossman, author of Failure Is an Option and a former CEO of six venture-funded companies, told Matt Uhler on What's Your Deal? that the failures were what made the better outcome possible. Most founders treat a pulled IPO as a defeat. Mike, who ran that company, treats it as proof of his book's argument.
"Sometimes things are unpredictable, and sometimes failure is actually what helps lead to something more successful."
Mike began his career at Johnson & Johnson, Intuit and McKinsey, then left corporate life roughly 30 years ago to found and run venture-backed companies, six of them as CEO.
The full interview is covered here so you can skip it. 46 minutes of audio, 8 minutes of reading.
Here are the 8 lessons that matter.
Key Takeaways
Two failed IPO attempts ended in a sale worth more than either listing would have raised
Mike says focusing on the outcome is a distraction, and his results improved once he stopped
Congress once wiped out a business he had grown to a $30 million run rate
Adjacent opportunities are rarely as close as they look, so doing less usually wins
A CEO who is sure of the path should be willing to risk being fired by the board
Nearly every company Mike ran became profitable through spending discipline, not growth at any cost
Going fully remote in COVID made recruiting easier, not harder, for a 300-plus-person company
Advice from Bill Campbell, over his own board's objections, made one company's sale possible
1. Two Failed IPOs, Then a Sale
Mike's most recent company was US-based but spent about nine months preparing to list in Australia. COVID hit and the plan collapsed. A second attempt later fell through too. After roughly 18 months and two failed IPOs, a strategic acquirer stepped in.
Mike Grossman's company sold for more than either IPO would have raised
"A big company came along, swooped in, and paid more money, meaningfully more money, to buy us than we would have received had we gone public in the first place." — Mike Grossman
Mike opened the interview with it as his clearest example of a failure that helped.
"Sometimes things are unpredictable, and sometimes failure is actually what helps lead to something more successful." — Mike Grossman
