
What can Startup Founders learn from Bank Robbers?
04/07/25 • 37 min
In this episode, we explore what aspects of the criminal mindset -- and prison life -- can be applied to the journey of startup founders -- both in funding and growing their businesses. Graceann Bennett interviews author Gregory Roberts as he relates colorful stories of both his successful string of startups, as well as how he actually funded one of his companies with a bank robbery. It then moves into prison, where Roberts deals with some of the more powerful gangsters in America, and compares their leadership styles to those of capitalist CEOs.
order your copy of the book today at piratesoldierking.com
In this episode, we explore what aspects of the criminal mindset -- and prison life -- can be applied to the journey of startup founders -- both in funding and growing their businesses. Graceann Bennett interviews author Gregory Roberts as he relates colorful stories of both his successful string of startups, as well as how he actually funded one of his companies with a bank robbery. It then moves into prison, where Roberts deals with some of the more powerful gangsters in America, and compares their leadership styles to those of capitalist CEOs.
order your copy of the book today at piratesoldierking.com
Previous Episode

Manhood : in Prison, and in the Free
In this third episode, Graceann Bennett interviews author Gregory Roberts about how the ideals of manhood and self-identity are embodied in the all-male prison population, a group that is almost all alpha-males, forced to live together in tight quarters. They then contrast this with how men have been emasculated in 21st Century Western Culture, and talk about how "old-school" manhood might be able to inform and guide today's younger generations.
order your copy of the book today at piratesoldierking.com
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In this episode, we talk about Gregory's journey as the son of two agnostic scientists into a bona fide worshipper of Satan and finally his transformation into a born again Christian, and how that transpired in prison... as well as some valuable wisdom that he learned along the way.
order your copy of the book today at piratesoldierking.com
Pirate Soldier King : The Interviews - What can Startup Founders learn from Bank Robbers?
Transcript
All right. Welcome to Pirate Soldier King. I'm your host, Graceann Bennett, interviewing Gregory Roberts. All right. Okay. This one, Excited for today. So this one, this one's a good one because this one gets personal. So in addition to hosting this show with you, I'm also a startup CEO. and embarking on, yeah, exactly. You got the holy water right there for the company. So someone might be asking themselves, how does a startup CEO, successful startup CEO like yoursel
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