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Prosecutors said Fleishman acted as a middleman by introducing hedge fund traders and company execs he knew would give them illegal tips.
In September 2011, he was found guilty of one count of conspiracy to commit securities fraud and one count of conspiracy to commit wire fraud.
Fleishman was sentenced to 30 months in federal prison. He ended up having to serve just 14 months at a minimum security camp in Colorado.
Here are a few takeaways from his Reddit AMA:
On His Daily Routine:
"I had a routine of running, reading and writing. I got some naps in too!"
On The Worst Part About Prison:
"The worst part was just not being able to be with my family. Missed wearing my own clothes, eating fresh fruits and vegetables, driving a car and surfing the Web."
On His Workout Regimen:
"I ran about thirty miles a week. I walked about twenty. I did push-up, pull-ups, dips 3-4 times a week. For me the best place was on the track walking or running laps, listening to my music at the foot of the Rockies in the desolation of the high desert plains."
"Guys are really disciplined for the most part. I was a slacker compared with the routines of others. Good friend I made there lost over a hundred pounds. There is a lot of positive peer pressure. Saying you don't work out is like saying you don't usually shower!"
On His Prison Job:
"I made 12 cents an hour locked up in a kitchen cleaning and filling trays for folks like the Unibomber."
On Special Skills He Learned:
"I learned how to make a pizza crust in a microwave using a tortilla and olive oil."
On His Favorite Books He Read:
"Jonathan Tropper Nelson Mandela Mark Twain TC Boyle "Born to Run" "Man's Search for Meaning"
"I only read about a book a week. I knew guys who read a book a day! Inmates are very disciplined...or many are in terms of diet, exercise and education."
On Being A Diabetic In Prison:
"Was not easy. At least the meds were free! But I had very few options in terms of food and could not test my blood sugars throughout the day. I had to line up at 6am for Medical if I wanted to do so!"
On What The Other Inmates Did To Get Locked Up:
"90% of the guys at the Camp in Colorado were there on drug charges. Many of them for selling pot. My bunkmate like to point out how when he was on his way to the prison to self-surrender he saw a ton of pot shops in Denver."
On Whether Prison Is Really Like 'Orange Is The New Black':
"I have not yet read the book but really enjoyed it on Netflix. They get a lot right--details like the blankets were identical to the ones I slept with!"
Since his release, Fleishman has written a book "Inside Story: The Wall Street Criminal Who Wasn't". Fleishman claims that he didn't commit those insider trading crimes.
"I found myself caught in an absurd injustice that saw me first accused then convicted of an Insider Trading crime I did not commit. Unlike many who pled guilty in exchange for probation, and others who cooperated with the FBI and whose lies under oath were exposed in my own trial, I chose to maintain my integrity and my innocence and paid the price, receiving a prison sentence of two and a half years," he writes on his website.
He says he's currently working at a small software startup his friend run.