Podcast: Lessons on Life from Former White Collar Criminal Jeff Grant on The Sydcast

With Prof. Sydney Finkelstein of the Tuck School of Business at Dartmouth College, Oct. 19, 2021

4 min readOct 20, 2021

This is perhaps my most incisive podcast ever (at least I think so). How could it not be, as I was interviewed by Prof. Sydney Finkelstein of the Tuck School of Business at Dartmouth College. A must-listen if you and/or someone you care about have been prosecuted for a white collar crime. — Jeff

Episode Summary:

He is addicted to prescription opioids, he attempts suicide, he’s found guilty of white-collar crime and serves 13 months in prison. Now he’s out, free, and has a chance to do something good for others, and himself, with the rest of his life. This was, and is, Jeff Grant, and on this episode of The Sydcast we hear his story. Link to Sydcast on Art19.com: https://art19.com/shows/the-sydcast/episodes/b6473d6d-3cc5-4484-b4ba-42ddad226991.

Listen on Spotify:

https://open.spotify.com/episode/76SiZJYqWMu9ka9Sx2aPfT

Listen on Apple Podcasts:

https://podcasts.apple.com/us/podcast/111-lessons-on-life-from-former-white-collar-criminal/id1453232081?i=1000538873869

Sydney Finkelstein

Syd Finkelstein is the Steven Roth Professor of Management at the Tuck School of Business at Dartmouth College. He holds a Master’s degree from the London School of Economics and a Ph.D. from Columbia University. Professor Finkelstein has published 25 books and 90 articles, including the bestsellers Why Smart Executives Fail and Superbosses: How Exceptional Leaders Master the Flow of Talent, which LinkedIn Chairman Reid Hoffman calls the “leadership guide for the Networked Age.” He is also a Fellow of the Academy of Management, a consultant and speaker to leading companies around the world, and a top 25 on the Global Thinkers 50 list of top management gurus. Professor Finkelstein’s research and consulting work often relies on in-depth and personal interviews with hundreds of people, an experience that led him to create and host his own podcast, The Sydcast, to uncover and share the stories of all sorts of fascinating people in business, sports, entertainment, politics, academia, and everyday life.

Jeff Grant

After an addiction to prescription opioids and serving almost fourteen months in a Federal prison (2006–07) for a white-collar crime he committed in 2001 when he was lawyer, Jeff started his own reentry — earning a Master of Divinity from Union Theological Seminary in the City of New York, majoring in Social Ethics. After graduating from divinity school, Jeff was called to serve at an inner city church in Bridgeport, CT as Associate Minister and Director of Prison Ministries. He then co-founded Progressive Prison Ministries, Inc. (Greenwich, CT), the world’s first ministry serving the white collar justice community.

On May 5, 2021, Jeff’s law license was reinstated by the Appellate Division of the Supreme Court of the State of New York.

Now again in private practice, Jeff is an attorney and counselor-at-law providing private general counsel, legal crisis management, and dispute strategy and management services to individuals and families, real estate organizations, family-owned and closely-held businesses, the white collar justice community, and special situation and pro bono clients.

For over 20 years Jeff served as managing attorney of a 20+ employee law firm headquartered in New York City, and then Westchester County, NY. Among other practice areas, the firm engaged in representation of family-owned/closely held businesses and their owners, business and real estate transactions, trusts and estates, and litigation. Jeff also served as outside General Counsel to large family-owned real estate equities, management and brokerage organizations, in which role he retained, coordinated and oversaw the work of many specialty law firms, including white collar defense firms.

Insights from this Episode

Why Jeff wanted to become an attorney
Family struggles Jeff went through during his auto-medication addiction problems
How Jeff ended up in prison and what his experience was
The steps of Jeff’s return journey to life after prison
How Jeff supports white-collar criminals
Patterns of white-collar crimes
Institutional challenges towards fraud

Quotes from the Show:

“I became addicted and slowly I started to deteriorate where I couldn’t show up at work anymore and I couldn’t run my firm even though it was continuing to be successful” — Jeff Grant [12:11]
“I was betting my livelihood and health of my family and my future in ways that were just reckless” — Jeff Grant [17:02]
“I learned more about human nature and respect and care and character in prison than I’ve learned in my entire life.” — Jeff Grant [24:48]
“[About his early life as a successful attorney] Positional power and money bought me the illusion that I had anything important to say and that anybody ever cared what I had to say, and the truth was that I was just a narcissistic mess” — Jeff Grant [27:18]
“I’m afraid that what we are doing is that we are teaching business leaders and political leaders…we are teaching them the wrong values” — Jeff Grant [50:17]
“[About people who make fraud] It’s not okay to take advantage of the system so long as you, either don’t get caught or if you do get caught, you won’t get prosecuted for it” — Jeff Grant [50:34]