By David Meister
Easy Investing
The proliferation of trading apps and user-friendly brokerage websites like Charles Schwab and Fidelity has made it easier than ever to open investment accounts and start trading. And this trend isn’t limited to the outside world. Financial literacy is growing both in the public and behind prison walls. Inmates across the country are taking advantage of financial courses, mentoring each other, and educating themselves on how to make their money work for them.
A Profitable Pastime
In 2019, I started hearing good things about the financial literacy class at the Idaho Department of Correction. I had a connection to the class through a Teacher Assistant I knew, and a great rapport with the instructor — we all called him “Mr. D” because no one could pronounce his last name.
Though I wasn’t enrolled in the class, I was allowed to check out financial books and take home copies of the course materials. What fascinated me most was the Direct Investment Plan (DIP), which allowed inmates to buy stock directly from companies using snail mail — bypassing the need for a broker or brokerage account, both of which are largely inaccessible to incarcerated individuals.
DIP plans made investing tangible. Even owning a handful of shares made the market feel real. I was hooked. By May 2020, I was ready to send in my first DIP order.
Then the COVID pandemic hit, and the stock market crashed. Even with my limited knowledge at the time, I knew this was a golden opportunity to buy. But DIP purchases take months to process — and I needed something faster.
Since I couldn’t open a brokerage account without a valid ID, a family member stepped in and opened one in their name, listing me as the beneficiary. I was officially in the game.
I scraped together what I could — $90 here, $150 there — and started buying bargain-priced shares of United States Oil (USO), an ETF that owns stock in American oil companies. It was trading at just over $2 a share when I bought in. I figured, if the U.S. oil industry couldn’t recover from COVID, nothing could. I was right.
The COVID-19 stimulus checks pumped extra cash into the prison economy, giving inmates like me the rare opportunity to invest. I put most of my stimulus money into the market, and even though USO performed a reverse split at the bottom of the market, it rebounded — and I made out like a bandit.
“Buy the dip” isn’t just a meme. It became a mindset.
Now, investing has become a popular pastime in prison. It’s like a new kind of sport with real stakes. Inmates gather to track stock trends, perform fundamental and technical analysis, share tips, and compare account sizes. It’s immersive, competitive, and community-driven.
The inmates most drawn to investing are usually over 35 or came in with some financial background. But it’s not just the college-educated types. The guy who runs the poker table — the one who does mental math without blinking and understands odds — often excels in the world of stocks too.
It’s the thrill of the gamble. The rush of a good call. And like the drug trade, it carries real consequences when you get it wrong. That edge makes it addictive — and empowering.
Of course, there are huge barriers to investing from prison. Inmates can’t open bank accounts or brokerage accounts without a valid ID, and prison IDs don’t count. Even when they do have state IDs, many brokerage firms won’t work with incarcerated people. Some prison systems even ban inmates from operating businesses, which can prevent account creation altogether.
But there are exceptions. The Idaho Department of Correction has shown surprising openness, allowing inmates to open bank and brokerage accounts. The results have been overwhelmingly positive. A small but strong community of smart investors has emerged — and it’s changing lives.
Win, Win: Inmates Invest in Success
I’ve spent over twenty years incarcerated. Whether I remain behind bars or am released someday, investing gives me a legitimate way to earn money, provide for myself, and contribute to my future.
Financial literacy has given me more than knowledge — it’s given me purpose. It’s engaging. Immersive. It connects me to a future I can build, even from a cell.
These skills don’t stay locked up. They follow us home. Investing has become a tool for long-term success, and for some, even a chance to start saving for retirement.
Behind bars or beyond them — society wins when inmates invest.