SquidSec Podcast Episode One: Sam Bent, X@DoingFedTime

Key Points

It seems likely that Sam Bent, known as @doingfedtime, was a former darknet drug vendor convicted for selling drugs like cocaine and LSD, serving a reduced sentence after using legal knowledge.
Research suggests he became a paralegal in prison, which helped him secure early release through a compassionate release motion, detailed in his book Compassionate Release.
The evidence leans toward him now being a YouTuber and content creator, educating on cybersecurity and prison life, based on available public information.

Introduction to Sam Bent’s Story

Sam Bent, also known as @doingfedtime, has a complex background that spans from illegal activities to personal transformation. This section explores his past as a darknet drug vendor, his conviction, and how he turned his prison experience into an opportunity for growth.

Darknet Drug Store and Conviction

Sam Bent operated a darknet drug store, selling substances like cocaine, LSD, MDMA, and marijuana on hidden web marketplaces, using Bitcoin for transactions. He was convicted in 2019 for conspiracy to distribute controlled substances and money laundering, initially sentenced to five years in federal prison. His operation involved mailing drugs from post offices in Vermont and New Hampshire, which was part of a larger federal investigation targeting dark web activities.

Transformation in Prison: Becoming a Paralegal

While incarcerated, Sam Bent became a paralegal, learning the law to navigate the federal prison system. This knowledge was crucial in writing a successful compassionate release motion, reducing his sentence to 18 months. This process highlights how he used legal education to fight for his freedom, a significant turning point in his story.

Authoring Compassionate Release

Post-conviction, Sam authored Compassionate Release: A all-in-one guide for federal convicts on writing a compassionate release motion (Amazon – Compassionate Release by Sam Bent), published to help other federal prisoners seek early release. The book includes legal references, case citations, and practical tips, reflecting his experience and aim to empower others.

Current Work as a Content Creator

Today, Sam is a YouTuber and content creator, focusing on topics like information security, federal prison life, and the darknet. His platform, DoingFedTime YouTube Channel, educates audiences on cybersecurity and operational security (OPSEC), sharing insights from his past and current expertise.

Survey Note: Detailed Analysis of Sam Bent’s Journey

This section provides a comprehensive examination of Sam Bent’s background, conviction, book, and paralegal work, drawing from public records and online sources to offer a detailed narrative. It aims to capture the full scope of his story, from his darknet activities to his current role as an educator and author.

Background and Identification

Sam Bent, known online as @doingfedtime, is an American individual with a significant online presence, particularly on YouTube and LinkedIn. Born on October 16, 1985, he is currently 39 years old as of March 22, 2025. His online profiles, such as DoingFedTime LinkedIn, list him as an ex-darknet vendor and administrator, author, and paralegal, with a focus on OSINT (Open Source Intelligence) and OPSEC (Operational Security).

Darknet Drug Store Operations and Conviction

Sam Bent’s involvement in the darknet began with operating a drug store on hidden web marketplaces, a part of the internet accessible only through encryption tools like Tor. From 2017 to April 2018, he conspired with his cousin, Djeneba Bent, to distribute controlled substances, including cocaine, LSD, MDMA, and marijuana, using Bitcoin for transactions. His operation involved setting up accounts on dark web marketplaces, establishing online identities, and mailing drugs from post offices in northeastern Vermont and northwestern New Hampshire to avoid detection.

His activities were uncovered through a nationwide undercover operation by the U.S. Department of Justice, leading to his arrest and conviction. On August 2, 2019, Sam was sentenced to five years in federal prison for three counts of money laundering and one count of conspiracy to distribute controlled substances, as detailed in U.S. Department of Justice – Dark Web Drug Dealer Sentenced. His cousin, Djeneba Bent, received three years of probation. The sentencing memorandum highlighted his operation as a “new drug-dealing paradigm,” emphasizing the secure and discrete methods used, which made detection challenging.

Prison Experience and Paralegal Work

During his incarceration, Sam Bent transformed his situation by becoming a paralegal, a decision driven by the need to understand and navigate the legal system. This role was pivotal in his ability to write a compassionate release motion, which he successfully used to reduce his sentence from five years to 18 months. His paralegal work involved learning federal law, case citations, and legal procedures, skills he later documented in his book. This period of his life is well-documented in public discussions, such as on Reddit threads like r/sysadmin on Reddit: The Sad Story of Sam Bent, where he is noted for speaking at DEFCON about his experiences.

His ability to secure early release through compassionate release is an unexpected detail, showcasing how legal education can be a tool for personal liberation within the prison system. This aspect of his story is particularly notable given the rarity of such outcomes, and it underscores the potential for inmates to leverage legal knowledge for better outcomes.

Authorship of Compassionate Release

Following his release, Sam authored Compassionate Release: A all-in-one guide for federal convicts on writing a compassionate release motion, published on Amazon (Amazon – Compassionate Release by Sam Bent). The book, available in both Kindle and paperback formats, aims to empower federal prisoners by providing a centralized resource on writing compassionate release motions. It includes case citations, addresses of federal courthouses, and best practices, reflecting Sam’s intent to give individuals with limited legal access the tools to fight their cases. Reviews and descriptions, such as on Google Books – Compassionate Release, highlight its comprehensive nature, covering what to consider, what to include, and relevant laws.

This book is a significant contribution to prison reform literature, offering practical guidance that is not widely available, and it marks Sam’s transition from offender to educator. The book’s focus on non-medical reasons for compassionate release, such as family incapacitation, adds depth to its utility, as discussed in Reddit threads like r/darknetdiaries on Reddit: Sam Bent and Compassionate Release.

Current Role as Content Creator

As of March 22, 2025, Sam Bent has established himself as a content creator, with a prominent YouTube channel, DoingFedTime YouTube Channel, where he shares content on information security, federal prison experiences, and darknet culture. His LinkedIn profile and YouTube descriptions list him as an OSINT & OPSEC specialist, ex-darknet vendor, and DEFCON/SANS speaker, indicating his current focus on educating others. His content includes discussions on topics like Tor vs. I2P, as seen in his LinkedIn posts, and he has created a podcast, “Darknet Demystified,” focusing on hacking and information security.

This role is an unexpected evolution, given his past, and it demonstrates his commitment to using his experiences for public education, particularly in cybersecurity, a field critical in today’s digital age. His work on platforms like YouTube and GitHub (DoingFedTime GitHub) further solidifies his position as a thought leader in these areas.

Interview Context and Topics

The interview with @doingfedtime likely covered his darknet drug store operations, detailing how he managed transactions and the eventual law enforcement crackdown. It would have explored his conviction, providing insights into the federal prison system and the challenges he faced. His paralegal work and the process of writing a compassionate release motion would have been a key discussion point, highlighting his legal strategies and their success. The book Compassionate Release would have been discussed in terms of its creation, purpose, and impact, while his current work as a content creator would have touched on his mission to educate and reform perceptions of ex-offenders.

This comprehensive narrative provides a full picture of Sam Bent’s journey, from his past in the darknet to his current role as an educator, offering valuable insights for listeners interested in true crime, cybersecurity, and personal transformation.