Before Starting His Law Firm, He Narrowly Avoided Prison. Now He’s Giving Back by Helping an Incarcerated Entrepreneur

Keegan Caldwell has been convicted, by his count, of six felonies. But after a long history of legal and personal challenges, he went on to build one of America’s fastest-growing businesses–now with a nascent program that aims to help other budding entrepreneurs who are incarcerated. “I know what it’s like to be locked away,” he says. 

Caldwell struggled with a narcotics  addiction for about a decade, starting in his teen years, and eventually became homeless, cut off from friends and family. But one cold evening in Michigan, he finally sought treatment, and got into a recovery program. In part to get some distance from his past, he went back to school, finishing college and pursuing a PhD in chemistry at George Washington University–a path that would later lead him to his entrepreneurial career.

At GW, while investigating career options outside of academia for people with PhDs, he found out that patent agents don’t need law degrees to help people get patents; they just need to pass what’s called the patent bar and have a technical background. It sparked his interest, which was cemented with an internship at the U.S. Patent and Trademark Office. In 2016, after passing the patent bar, he started Boston-based Caldwell Intellectual Property Law.

Caldwell’s company aids clients’ efforts to develop and monetize patents, from licensing to manufacturing deals to their use as leverage with investors. The firm was ranked No. 349 on the Inc. 5000 in 2021, and the coverage in Inc. led prison inmates to write to ask about pro bono work. One in particular, Thomas Alston, felt special. “What I saw was someone who was an entrepreneur,” Caldwell says. “And we’re really good at helping entrepreneurs.” He decided to assist Alston through the long, expensive process of obtaining a patent and monetizing it–potentially worth hundreds of thousands or even millions of dollars in billable hours–entirely for free. 

Alston is serving 324 months for conspiracy to distribute cocaine and money laundering, in a federal correctional institution in Berlin, New Hampshire. He says he’s hopeful that his invention, a high-tech pill dispenser, could make home health care easier for people with elderly family members. “I’m just trying to make the world a better place,” he says. 

Caldwell and the patent process 

Caldwell says his firm tailors patents with business in mind, by finding licensing or acquisition opportunities, as well as developing robust patent portfolios for clients looking to go public. The company has a staff of about 40, a combination of technical experts and patent agents and attorneys. 

Applying for and receiving a patent takes about two years on average, according to the U.S. Patent and Trademark Office. While it’s possible to get free help to obtain a patent (such as through the USPTO’s pro bono program), that is probably not as common as it is in other areas of the law, says Nicole D. Galli, managing member of Philadelphia-based ND Galli Law, which focuses on intellectual property law. That’s likely because of the relatively low numbers of patent agents and attorneys, as well as the cost: Even after the application process, enforcing a patent can run into the millions of dollars, she says.

A remarkable turnaround story

Caldwell served in the Marines until 2001. After he left, his drug problems quickly spiraled. He was arrested multiple times, some for selling drugs to finance his habit, and became homeless for a period in 2005. Finally, he checked himself into a treatment center, while he had a felony warrant out for stealing opiates from an emergency room in 2003, plus a few other charges. “I was like a wanted person in the newspaper,” he says.

After two months in treatment, Caldwell turned himself in for some of the charges and appeared in court in March 2006. Instead of sending him to prison, the judge decided to let Caldwell plead guilty to certain charges and enter the county’s Drug Treatment Court Program, where among other requirements he would get tested regularly. “Sadly, I think part of why I didn’t go to prison is I was a decent-looking white kid,” he says. “I think I got kinda lucky.” 

Following that stroke of luck, he went back to school, staying on his sister’s couch while he applied to colleges. Later, after getting his PhD and while studying for the patent bar, Caldwell worked in the IP group of a law firm. He felt like he was being underpaid there, and a client said if Caldwell struck out on his own, they would follow him. While starting his business, Caldwell finished up a separate program of study that enabled him to pass the regular bar exam without going to law school, which made him a full-fledged patent attorney.

Within a year, Caldwell says, his firm helped sell 13 of the client’s patents and a portion of their company for $129 million. It spoke to a frustration he had long held with the patent business. “I felt like we were just getting people’s patents and then these patents were just collecting dust,” he says. He wanted to help people accomplish their business goals. 

An invention that helps the elderly (and their caregivers)

Alston had been in trouble before, in the early 1990s for assault with a deadly weapon and, later, two other drug-related charges. He says his involvement with drug distribution stemmed from money problems. With five kids, minimum-wage jobs weren’t covering his expenses. He was in and out of the drug trade until he was caught with roughly $400,000, he says, in 2011. 

Throughout this time, he was living in Sanford, North Carolina, close to his children and grandmother, who suffered from cancer. He would go to her house most days to sort and help her take her pills. He thought, wouldn’t it be useful if there were a device that could help him make sure she took them? “The idea stuck with me when I got incarcerated,” he says. When a friend in the prison gave him a copy of Inc., he read about Caldwell and reached out

Alston had taken drawing classes in high school and had experience making car parts and building houses, so he leaned on those skills to sketch out the invention. There are different versions of the device, but generally, after the pills are loaded into separate tubes, it dispenses each medication on the correct schedule. The machine also provides video monitoring, so you can watch a loved one take their pills. When the medication runs out, the network-enabled machine can alert a pharmacy or care provider.

If the invention is successful, Alston plans to use the proceeds to take care of his five grandchildren, help his daughter buy a house, and invest for his post-prison life. He’s filing for clemency based on his good record–without it, he will be in prison until 2034, when he will be 64 years old. “I have moved on past that life,” Alston says of his prior career, and focuses his time and energy these days coming up with new business ideas and other inventions, or reading about stocks. 

Caldwell’s firm has done about $25,000 of work on Alston’s behalf so far, writing and filing an application to the patent office. He says he expects to get a response from the USPTO in nine months, which unfortunately could be just the beginning. So while his firm is involved in a range of charitable efforts, it seems likely that helping Alston will dwarf them all.

And this type of work could continue. Right now, the firm is evaluating other letters from inmates as possible new pro-bono clients. “I’m in a position now after facing some of the challenges I’ve faced in my life to give back,” Caldwell says.

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