Ex-Felons Who Found Success After Prison

Navigating life post-incarceration can appear to be an intimidating journey riddled with unknowns. Yet, as numerous individuals affected by the justice system have experienced, the path to achievement upon leaving prison, as you reconstruct and reshape your identity, can lead to extraordinary, fulfilling, and significant accomplishments.

The stories featured here are testaments to the strength of the human spirit and the power of redemption. The individuals profiled in this blog have not only overcome the barriers posed by their incarceration but have also emerged as influential figures in their respective fields. Their journeys underscore a crucial message – that the end of a prison term is not the end of the road.

Jordan Belfort

Famously known as the “Wolf of Wall Street,” Jordan Belfort started his career as a stockbroker at L.F. Rothschild and later founded Stratton Oakmont, a brokerage firm involved in financial fraud and money laundering. His firm employed over 1,000 stock brokers and was responsible for stock issuances totaling more than $1 billion. In 1999, Belfort was indicted for securities fraud and money laundering. He cooperated with the FBI, leading to a reduced sentence of 22 months in prison out of a four-year sentence.

Belfort’s Post-Incarceration Comeback

After his release, Belfort reinvented himself as a motivational speaker and writer. He authored the memoirs “The Wolf of Wall Street” and “Catching the Wolf of Wall Street,” which became best-sellers published in around 40 countries and translated into 18 languages before being adapted into a film directed by Martin Scorsese titled the “Wolf of Wall Street.” He also ventured into cryptocurrency investments and remains a prominent public figure.

Martha Stewart

Martha Stewart is a renowned American entrepreneur and domestic lifestyle innovator. Her rise to fame continued with the launch of the monthly magazine “Martha Stewart Living” in 1990 and the syndicated television show of the same name in 1993. These ventures were key steps towards realizing her goal of creating a multichannel media and marketing firm. Martha Stewart Living Omnimedia went public in 1999, briefly making Stewart a billionaire and the first female self-made billionaire in the U.S.

However, Stewart’s career faced a significant setback in December 2001 when she sold 4,000 shares of ImClone Systems, leading to accusations of insider trading. This led to her stepping down as chairman and CEO of her company in 2003. She was eventually convicted and sentenced to five months in prison which she served in Alderson Federal Prison Camp in West Virginia, followed by five months of home confinement.

Martha Stewart’s Success After Prison

Despite these challenges, Stewart rebuilt her career post-incarceration. She returned to television with new shows and business ventures, including a line of CBD gummy supplements launched in 2020.

Charlie Shrem

Charlie Shrem, an early Bitcoin entrepreneur, co-founded BitInstant, a Bitcoin exchange company, and served as its Chief Executive Officer and Compliance Officer. He was also a Vice Chairman of the Bitcoin Foundation, dedicated to promoting the Bitcoin virtual currency system. Shrem’s legal troubles began when he was arrested in January 2014 at JFK Airport for his involvement in a money laundering case related to the Silk Road marketplace, an online black market.

Prosecutors alleged that Shrem and his co-defendant, Robert Faiella, were involved in laundering $1 million worth of bitcoins to facilitate illegal drug purchases on Silk Road. Despite his role as Compliance Officer, responsible for ensuring BitInstant’s adherence to anti-money laundering laws, Shrem facilitated Faiella’s Bitcoin purchases for Silk Road users. This included processing orders for Faiella, failing to file suspicious activity reports, and deliberately helping Faiella circumvent BitInstant’s anti-money laundering restrictions.

In September 2014, Shrem pleaded guilty to a reduced charge of aiding and abetting unlicensed money transmission. He was sentenced to two years in prison in December 2014 and ordered to forfeit $950,000. He began his prison sentence at Lewisburg Federal Prison Camp in Pennsylvania in March 2015 and was released around June 2016.

Charlie Shrem’s Post-Incarceration Comeback

After his release, Shrem continued his involvement in the cryptocurrency world. He joined Jaxx in 2017 as its director of business and community development and later served as the chief operating officer. In the same year, he became involved in the cryptocurrency Dash and proposed the creation of a debit card for Dash coins. He also founded CryptoIQ, an advisory business aimed at mainstreaming cryptocurrencies. In November 2018, he announced a partnership with the Internet operating system Friend as an advisor.

Despite his conviction, Shrem has continued to be an active figure in the cryptocurrency community, contributing to its development and engaging in various projects and initiatives.

Robert Sherrill

Raised in a challenging environment in Nashville, Robert Sherrill‘s early life was troubled. His mother’s addiction to drugs and the eventual eviction from their home led him down a difficult path. In search of stability and driven by a need for financial security, Sherrill turned to selling drugs, which eventually led to his arrest and a 17-year sentence for a drug transaction. His time in prison became a turning point. Sherrill, reflecting on his father’s death in prison and having his desire to contribute to his society.

Robert Sherrill’s Success After Prison

Upon his release, Sherrill opened Imperial Cleaning Systems (ICS), a growing commercial cleaning, restoration, and janitorial company based in Nashville. The success of this business and others he started in the wake of its success lead to his new nickname, “The Million Dollar Janitor.”

His efforts in community service and entrepreneurship were recognized when he received both gubernatorial and presidential pardons. These pardons were not only a testament to his personal transformation but also a symbolic lifting of the stigma associated with his past, allowing him to further his business goals and continue his impactful work with the youth of Nashville.

Piper Kerman of “Orange is the New Black” Fame

Piper Kerman‘s journey to prison began after she graduated from Smith College. In 1993, at 24 years old, she became involved in a serious criminal activity when she flew to Belgium with a suitcase of money intended for a West African drug lord. This was a part of her involvement with a woman who was deeply engaged in a drug-smuggling ring. Kerman left this criminal lifestyle after a few months, but the consequences of her actions caught up with her. Kerman was indicted in 1998 on charges of felonious money-laundering activities and sentenced to 15 months in the federal correctional facility in Danbury, Connecticut, of which she eventually served 13 months.

Kerman started writing a book while incarcerated, culminating in her memoir “Orange Is the New Black: My Year in a Women’s Prison.” This book was later adapted into an Emmy Award-winning original series for Netflix, which ran for seven seasons.

Piper’s Success After Prison

Following her release, Kerman became actively involved in advocacy and reform efforts related to the criminal justice system. She serves on the board of the Women’s Prison Association and has been a part of various initiatives and organizations working in public interest. Kerman has spoken at significant platforms, including the White House on topics like re-entry and employment, the importance of arts in prisons, and the conditions for women in the criminal justice system. She has also testified before various U.S. Senate and House subcommittees on issues concerning solitary confinement, conditions for women prisoners, and the federal Bureau of Prisons.

Michael Milken

Michael Milken, a notable American financier, played a pivotal role in the development of the market for high-yield bonds, also known as junk bonds, during the 1970s and 1980s. Milken’s innovative strategies in the bond market transformed the way companies raised capital and were instrumental in many corporate takeovers of the 1980s.

After graduating from the University of California, Berkeley, in 1968, Milken began his career at Drexel Firestone, which later became Drexel Burnham Lambert. There, he became the head of the bond-trading department and was central in popularizing junk bonds, which were seen as high-risk but offered high returns. By the mid-1980s, Milken’s network and Drexel Burnham’s ability to raise large amounts of capital significantly influenced the landscape of corporate financing and acquisitions.

His career was derailed when he was indicted for racketeering and securities fraud in 1989 as part of an insider trading investigation. He pled guilty to securities and reporting violations but not to racketeering or insider trading. Initially sentenced to ten years in prison, his term was reduced to two years for cooperating with authorities and demonstrating good behavior.

Milken’s Success After Prison

After his release from prison, Milken redirected his focus towards philanthropy and medical research. He co-founded the Milken Family Foundation and became the chairman of the Milken Institute. He has been heavily involved in funding research into cancer and other life-threatening diseases, leveraging his wealth and network to support various medical and educational initiatives. Milken’s efforts in this field earned him recognition as a major philanthropic figure, notably in medical research.

Martin Skhreli

Martin Shkreli, often known as the “Pharma Bro,” is a former hedge fund manager and CEO of the biopharmaceutical company Retrophin Inc. Shkreli first garnered attention in the finance world during his time at Cramer, Berkowitz, and Company, where he made a name for himself through short-selling stocks. After leaving Cramer Berkowitz, he worked as a financial analyst and then went on to found his first hedge fund, Elea Capital Management, in 2006. His career in the pharmaceutical industry included the acquisition and substantial price increase of certain drugs, notably Thiola, a drug used to treat the rare disease cystinuria.

Shkreli’s legal troubles began with his involvement in multiple fraudulent schemes. In 2018, he was sentenced to seven years in prison for committing securities fraud and securities fraud conspiracy. This sentence came after a conviction where he was found guilty of two counts of securities fraud and one count of securities fraud conspiracy. These charges were related to his management of two hedge funds, MSMB Capital Management and MSMB Healthcare, and his role at Retrophin. Shkreli was accused of defrauding investors and engaging in a complex scheme involving the manipulation of Retrophin’s stock.

During his time in prison, Shkreli was noted for not being a model prisoner. He was initially held at the federal prison in Fort Dix, New Jersey, known for its relatively lax atmosphere. However, he was later transferred to the Metropolitan Detention Center in Brooklyn and then to a federal prison in Allenwood, Pennsylvania, due to his continued involvement in running his business illegally using a cell phone from prison. His incarceration at Allenwood was marked by stricter security and less freedom compared to Fort Dix. Even from prison, Shkreli attempted to stay in the public eye. In 2020, he requested a temporary release to assist in developing a vaccine for COVID-19.

Shkreli’s Success After Prison

Shkreli’s comeback story is playing out in real-time on his X account, where he often shares his entrepreneurial ideas and talks about the progress he’s making with various artificial intelligence tools. As of December 2023, Shkreli is involved in a software company called DL Software and an AI project called Neets which offers speech and voice cloning.

Building Your Post-Incarceration Comeback Story

No matter where you are in your journey: pre-sentencing, inside right now, or navigating re-entry, your post-incarceration comeback story begins now. Those who are pre-incarceration can start making plans for their release, including starting to write a book, planning which classes to take while away, or coming up with a strategy to address substance abuse issues, all of which can better position you for success upon re-entry. If you’re navigating re-entry and have your bases covered (including staying in compliance with supervised release), it’s about finding a support group, gaining secure employment and starting to do the brick-by-brick hard work of showing those in your community that you’re a changed person and that you’ve learned from your mistakes.

It’s possible.