My Favorite Mistake: Business Lessons from Failures and Success

A Former Bank CEO’s Journey from Entrepreneurship to Incarceration and Back: Shaun Hayes


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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.

Shaun discusses the impact of his experience on his personal and professional life and how he has worked to rebuild his reputation and move forward. The episode offers valuable insights into the challenges of entrepreneurship and the importance of taking responsibility for one's actions.

Shaun provides valuable insights into the challenges of entrepreneurship, discussing how his ambition and drive to succeed led him down a path that ultimately resulted in his downfall. He emphasizes the importance of taking responsibility for one's actions and not making excuses, acknowledging that he made mistakes and accepting the consequences of his actions. Despite the difficulties he faced, Shaun remains optimistic and determined to use his experience to help others learn from his mistakes.

We also discuss the challenges of being a CEO, the importance of transparency and honesty in business, and the need for forgiveness and second chances.


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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My Favorite Mistake: Business Lessons from Failures and SuccessBy Mark Graban

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