My Favorite Mistake — 202: A Former Bank CEO’s Journey from Entrepreneurship to Incarceration and Back: Shaun Hayes

Author of “The Grey Choice” — Episode page with links, transcript, and more

My guest for Episode #202 of the My Favorite Mistake podcast is Shaun Hayes. He was the cofounder and former CEO of Allegiant Bancorp, headquartered in St. Louis, Missouri. Shaun started multiple successful businesses, was involved in the casino business, and bought, owned, and sold hundreds of residential and commercial properties. He is an entrepreneur, an author, a speaker… and a felon.

He was a principal at three banks that failed in 2011 and 2012. Five years after selling a company for an enormous profit, Shaun committed a felony. He was incarcerated for his crime eight years later. Now out of prison, he’s the author of The Grey Choice: Lessons on My Journey From Big-Time Banking to the Big House (and Back).

In this episode, Shaun tells two favorite mistake stories. The first was about “going crazy and wanting to fire somebody” when he then realized that the problems were the result of his mistakes as CEO of the bank. The second story is about the mistakes and bad choices that led to his conviction.

Questions and Topics:

At an early age – making decisions that are not illegal but grey in the “interpretation of the rules”?

How he justified it…

Why go forward with it even knowing it was illegal?

Did this lead to bank failures?

Why did the legal process take 7.5 years to play out before being indicted?

The dynamics / decision around pleading guilty?

Do you remember something early on that got you 1% off course?

The need to specifically define your moral compass?

What’s it like starting a business once out of prison?

Being a speaker today to help others?

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