I get asked a lot about the prison part—how long, what it was like, and how it felt knowing my name on ESPN for something that started as a weekend project.
Summary
This page isn't about drama, as much as I would like it to be. It's about context, and what happens when a hacker-founder type goes from building systems to living inside one that's piss-poorly preoptimized for everyone else.
What was your sentence?
36 months in federal prison, followed by 36 months of supervised release. Or, as I like to think of it: one startup lifecycle inside, one outside.
How long have you been out?
I was released in August 2025. So, as of this writing, I'm still counting months since my last metal detector.
The bureaucracy OS
The system optimized for sex offenders drug cases, and violence: there were many instances where there was no "other" checkbox. This had a trickle-down effect, too: inmates assumed that a short, well-groomed male was a sex offender because he didn't fit the profile.
What did you do all day?
I answered "what are you in here for?" a lot.
Okay, and what else?
I played a lot of basketball and stayed active on the track, making an effort to try to walk at least five miles every morning. I helped others with their legal work or whatever they were working on for their classes.
What was the food like?
For the most part it was actually pretty good! The portions just weren't enough.
Did you meet any cool people in prison?
Depends on your definition of cool, but probably not.
Did people know your case before you got to prison?
No more than a handful.
Was it violent?
No.
Was it boring?
Yes.
Was it petty?
Holy shit yes. Unbelievably.
If you're passing through like I was, there's little emotional investment made to stick with whatever established status quo that exists which is full of ways and means that you don't agree with.
For those who have more time to do, prison is their way of life. There were plenty of times when I decidedly went against unwritten rules because they didn't align with my moral values—mostly in regards to the treatment of out-group persons.
What did you read?
A lot more than I thought I would. Prior to being incarcerated I had never read a book—not even in high school.
| Book Title | Author |
|---|---|
| Unmasking Autism: Discovering the New Faces of Neurodiversity | Devon Price |
| A Little Less Broken: How an Autism Diagnosis Finally Made Me Whole | Marian Schembari |
| Mindblindness: An Essay on Autism and Theory of Mind | Simon Baron-Cohen |
| You Just Don't Understand: Women and Men in Conversation | Deborah Tannen |
| Emergence | Temple Grandin & Margaret M. Scariano |
| Nobody Nowhere: The Remarkable Autobiography of an Autistic Girl | Donna Williams |
| Autism: Explaining the Enigma | Uta Frith |
| Thinking in Pictures, Expanded Edition: My Life with Autism | Temple Grandin |
| Autism and Asperger Syndrome | Uta Frith (Editor) |
| Somebody Somewhere: Breaking Free from the World of Autism | Donna Williams |
| Original Sin: President Biden's Decline, Its Cover-Up, and His Disastrous Choice to Run Again | Carl Bernstein |
| Where Wizards Stay Up Late: The Origins Of The Internet | Katie Hafner & Matthew Lyon |
| The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life | Mark Manson |
| An Anthropologist On Mars: Seven Paradoxical Tales | Oliver Sacks |
| The Power of Habit: Why We Do What We Do in Life and Business | Charles Duhigg |
| Smarter Faster Better: The Transformative Power of Real Productivity | Charles Duhigg |
| Neurotribes: The Legacy of Autism and the Future of Neurodiversity | Steve Silberman |
| The Trouble With Testosterone: And Other Essays On The Biology Of The Human Predicament | Robert M. Sapolsky |
| The Cuckoo's Egg: Tracking a Spy Through the Maze of Computer Espionage | Clifford Stoll |
| The Flavor Matrix: The Art and Science of Pairing Common Ingredients to Create Extraordinary Dishes | James Briscione & Brooke Parkhurst |
| Seveneves | Neal Stephenson |
| Born Standing Up: A Comic's Life | Steve Martin |
| Economics in One Lesson: The Shortest and Surest Way to Understand Basic Economics | Henry Hazlitt |
| Every Tool's a Hammer: Life Is What You Make It | Adam Savage |
| Humble Pi: When Math Goes Wrong in the Real World | Matt Parker |
| How To: Absurd Scientific Advice for Common Real-World Problems from Randall Munroe of xkcd | Randall Munroe |
| The Molecule of More: How a Single Chemical in Your Brain Drives Love, Sex, and Creativity--and Will Determine the Fate of the Human Race | Daniel Z. Lieberman & Michael E. Long |
| Why We Sleep: Unlocking the Power of Sleep and Dreams | Matthew Walker |
| Extreme Programming Explained: Embrace Change, 2nd Edition | Kent Beck & Cynthia Andres |
| Twin Cities Then and Now | Larry Millett |
| The Tipping Point: How Little Things Can Make a Big Difference | Malcolm Gladwell |
| Revenge of the Tipping Point: Overstories, Superspreaders, and the Rise of Social Engineering | Malcolm Gladwell |
| Practical Object-Oriented Design in Ruby: An Agile Primer | Sandi Metz |
| Patterns of Enterprise Application Architecture | Martin Fowler |
| Closing Time: Saloons, Taverns, Dives, and Watering Holes of the Twin Cities | Bill Lindeke |
| Roadside Geology of Minnesota | Richard W. Ojakangas |
| Creating Minnesota: A History from the Inside Out | Annette Atkins |
| Mr. Putin: Operative in the Kremlin | Fiona Hill & Clifford G. Gaddy |
| Why Zebras Don't Get Ulcers, Third Edition | Robert M. Sapolsky |
| Peril | Bob Woodward & Robert Costa |
| The Master Switch: The Rise and Fall of Information Empires | Tim Wu |
| War | Bob Woodward |
| The Interpretation of Dreams | Sigmund Freud |
| Determined: A Science of Life without Free Will | Robert M. Sapolsky |
| Fire and Fury: Inside the Trump White House | Michael Wolff |
| Fear: Trump in the White House | Bob Woodward |
| Root Beer Lady: The Story Of Dorothy Molter | Michael Furtman |
| Jony Ive: The Genius Behind Apple's Greatest Products | Leander Kahney |
| Rework | Jason Fried & David Heinemeier Hansson |
| Just The Tip (The Pen Fifteen Club) | Jason Fried & David Heinemeier Hansson |
| Getting Real: The Smarter, Faster, Easier Way to Build a Successful Web Application | Jason Fried et al. |
| Salt, Fat, Acid, Heat: Mastering the Elements of Good Cooking | Samin Nosrat |
| Robert Oppenheimer: Letters and Recollections | Alice Kimball Smith & Charles Weiner (Editors) |
| A Boundary Waters History: Canoeing Across Time | Kevin Proescholdt |
| We Were the Lucky Ones: A Novel | Georgia Hunter |
| American Prometheus: The Inspiration for the Major Motion Picture OPPENHEIMER | Kai Bird & Martin J. Sherwin |
| Behave: The Biology of Humans at Our Best and Worst | Robert M. Sapolsky |
| What If: Serious Scientific Answers To Absurd Hypothetical Questions | Randall Munroe |
| Stieg Larsson's Millennium Trilogy | Stieg Larsson |
| Founders at Work: Stories of Startups' Early Days | Jessica Livingston |
| A Year in the Wilderness: Bearing Witness in the Boundary Waters | Amy Freeman & Dave Freeman |
| The Mammoth Book of Chess | Graham Burgess |
| What Happened to You?: Conversations on Trauma, Resilience, and Healing | Bruce D. Perry & Oprah Winfrey |
| Taste: Surprising Stories and Science about Why Food Tastes Good | John McQuaid |
| The Art Of Holding Together Your Relationship While Doing Time In Prison | Lora Shaner |
| Cooking for Programmers 0x00 - Funny Nerd Cookbook | Tim Schroder |
My favorites were Determined, Behave, Salt Fat Acid Heat, Unmasking Autism, Enigma, and Neurotribes.
Are you good at basketball though? You had a sports website
Those who can't do...