Before President Donald Trump took the oath of office in January, he handed off management of the Trump Organization's business interests to his two eldest sons, Donald Trump Jr. and Eric Trump. The family-owned company has been in various lines of business over the years—most famously, there are hotels, casinos, and golf resorts, some owned and others licensed. Ties, steaks, and a controversial seminar business have also borne the Trump name.

But Donald Trump Jr. has also been involved with one particular business with real implications for the technology sector: patent enforcement. Beginning in 2011, Trump Jr. worked for—and owned part of—a company called MacroSolve. While MacroSolve had supported itself selling software for more than a decade, by 2011 its focus had shifted to patent lawsuits as the company's main source of profit.

MacroSolve's actions soon made it part of a longstanding debate in the tech industry over "patent trolls," companies that do little or no business other than filing patent lawsuits. But MacroSolve management never accepted the idea that the company was a "troll," and it said so in interviews.

"If you enforce your rights, you're a troll," MacroSolve CEO Jim McGill said in a 2014 interview with Ars Technica. "If you don't, big companies will walk all over you."

Whatever you call it, MacroSolve's brand of patent enforcement had initial success—its lawsuits earned the company close to $5 million. When the litigation campaign eventually collapsed in 2014, MacroSolve was absorbed by a defense contractor called Drone Aviation Holding Corporation. That organization has its own close ties to the Trump presidency, and there's no telling whether, or if, Drone Aviation will try to enforce old MacroSolve patents or its own patents.

President Trump's views on patents and patent reform still aren't clear, but family members have strongly influenced his policy views in other areas so far—and there's a bit more clarity as to where Trump Jr. stands on this topic. After browsing through MacroSolve's litigation history, reading every MacroSolve 10-K, and looking through every news clip and press release that mentioned the words "MacroSolve" and "Trump" via the Nexis database, a pro-patent vantage point emerges. On top of all that, public statements from Trump Jr. himself reveal some strongly held personal views on patent policy that emerged during his work for MacroSolve.

“Location, location, location”

MacroSolve was originally known as Anyware Mobile Solutions, an Oklahoma company founded in 1997 by David Payne. The plan was to create applications for PDAs and cellphones, according to a Tulsa World story on MacroSolve's "rise and fall." In 2008, the company went public, hoping to profit by helping businesses embrace the era of the smartphone.

It didn't work out. Between 2008 and 2010, sales plunged from $2.7 million to $638,000. But MacroSolve got one last, great chance—US Patent No. 7,822,816, issued in October 2010. At the time, MacroSolve's chairman said the patent could make the company into a billion-dollar business. The patent describes a "remote computing device" that sends out a questionnaire to a user, gets answers, and makes those answers available on the Web. Thus, in MacroSolve's view, it applies to anyone using questionnaires on a mobile app.

In early 2011, MacroSolve embraced patent litigation as a means of making money. The company went in big: over the course of a year, MacroSolve filed dozens of lawsuits against 59 different companies, all filed in the patent-friendly Eastern District of Texas. Patent trolling had hit a peak, and it was easier than ever to squeeze money from companies afraid of litigating in East Texas. Discovery rules in that district were tough on defendants, and judges rarely decided cases on summary judgment, making patent litigation hugely expensive. After just a few months of filing lawsuits, MacroSolve reaped more than $1 million in settlements—much more than its struggling software business was worth.

Perhaps fearing blowback from its aggressive litigation campaign, MacroSolve's board decided to make someone else the company's public face. That's when it turned to Donald Trump Jr., who was hired on as the new spokesman in September 2011. Trump Jr. struck a deal to do two years of PR work, and he received at least $45,000 and 5,000,000 shares of MacroSolve stock as an initial payment, according to company financial reports.

In interviews and comments made at the time, Trump Jr., then executive vice president of the Trump Organization, described MacroSolve as a "pioneer" that he was excited to partner with. He called mobile apps "digital real estate." He said the Trump Organization would be integrating MacroSolve technology into its businesses.

"Just as in physical real estate, digital real estate is location, location, location," Trump Jr. said in a statement after he was hired in 2011. "Having a company's brand and logo on the screen of mobile devices is a valuable place to be for a company looking to drive revenues and productivity."

In an interview with Oklahoma City's Journal-Record, Trump Jr. said that he would be "opening his Rolodex" to help MacroSolve expand beyond Oklahoma. The company's patent was set to be a big part of that effort. MacroSolve owned "a landmark patent with stability and very high growth potential as one of the few publicly traded companies in the industry," the new spokesperson told the newspaper.

“That hunter's nose”

Trump Jr. immediately took on a public role in pushing the newly patent-focused company. In November 2011, he introduced MacroSolve CEO Steve Signoff to investors at the New York City Small Cap Conference.

"On our show Celebrity Apprentice, it really only takes one single factor to set an apprentice apart from another," Trump Jr. told the crowd. "It isn’t their popularity, their appearance, their famous or infamous name... It’s their edge."

For businesses, that "edge" is a good "mobility solution," said Trump Jr. "That is why it was so important for me and Trump-branded businesses to find a mobility-solutions company with that edge in the digital world. That's MacroSolve."

MacroSolve had "that hunter's nose," a proven record in mobile, and "their patent portfolio puts them years ahead in innovation," he added.

If the company's patent was innovative, that innovation wasn't translating into sales of products or services. The company's sales plummeted through the end of 2011, but MacroSolve executives told investors to hang on—the Trump "edge" was just around the corner.

"These third quarter revenues do not yet reflect the significant and strategic business development agreements we've put in place in Q2 and Q3 with Donald Trump Jr. and The Richards Group, both of which we expect will yield us major national accounts and sales that will create a very positive impact," MacroSolve CEO Steve Signoff told investors in December 2011, explaining away dismal financial results.

Sales of the company's products kept slowing as MacroSolve's docket of East Texas cases grew. It filed 10 more lawsuits in December 2011, putting global travel companies on notice that their apps infringed the '816 patent. Four airlines got sued—Southwest, United, Continental, and American. So, too, did Priceline, Hotels.com, Travelocity, Hertz, and Avis.

In early 2012, MacroSolve filed lawsuits against a new batch of corporate defendants, including Facebook, Walmart, Yelp, Geico, Marriott, AOL, and Inter-Continental Hotels. It also sued Newegg, a retailer whose top brass had spoken out against patent trolls. Lawyers at Newegg and Geico would ultimately bring together a coalition of companies to fight MacroSolve's patent.