Over 20 years of tech and lifestyle entrepreneurship.
John Roa is a lifelong entrepreneur, technologist, philanthropist, business investor, and writer. He has founded and managed six technology companies since learning to program at age 11. His largest company, ÄKTA, went on to be one of the fastest growing companies in America in both 2013 and 2014, and was fully acquired by Salesforce Inc. (NYSE: CRM) in September 2015. He is currently the CEO of Caden.
“A Practical Way to Get Rich, and Die Trying”, Roa’s memoir on his meteoric rise, and subsequent crash, as the CEO of ÄKTA was released in September 2020 (Viking / Penguin Random House).
Outside of business, John is a passionate activist and philanthropist, having been a partner and donor to dozens of non-profit organizations as well as founding and running his non-profit organization, Digital Hope, from 2010 to 2014. Digital Hope focused on building a digital bridge between international NGOs with high levels of impact but little means of fundraising, and passionate micro-investors in America and Europe. Digital Hope successfully executed projects with orphanages, wildlife sanctuaries, schools, anti-trafficking centers, rehabilitation centers, and more, in over a dozen countries.
He is a sought-after speaker on the topics of Entrepreneurship, Artificial Intelligence, Innovation, Digital Transformation, and User Experience Design.
John Roa’s Second Acts
Entrepreneur John Roa made his imprint on Chicago’s tech scene with UX consultancy ÄKTA. With a host of projects on the way, however, that may have been just the beginning.
Sitting in the tranquil environs of his self-designed West Loop loft sipping a cocktail, John Roa is relaxed, composed—a picture of self-possession. As our conversation drifts from his many projects to philosophy to his habit of fostering kittens, he is, at turns, contemplative and almost whimsically reective. And why shouldn’t he be? At the age of 32, Roa has the world on a string. The founder of user experience consultancy ÄKTA, he sold the rm in late 2015 to San Francisco-based tech giant Salesforce for an undisclosed sum—walking away, one presumes, set for many lifetimes. Cut to a mere few weeks before the sale, however, and Roa’s life was anything but meditative.
“The last few months [before the sale] were so unbelievably stressful, it was at a level that I didn’t even understand stress could get to,” he says. “Debilitating stress, if I’m honest.”
While anxiety levels understandably ramped up for Roa as the sale approached, his entire journey with ÄKTA was, he says, an incredible, years- long high-wire act. A self-described below average student from Grosse Pointe, Mich., with huge entrepreneurial inclinations, Roa was “struggling through a business degree” at Western Michigan University when he began running a video game marketing firm startup in Los Angeles. This exposed him to who would eventually become some of the sector’s most talented designers and user experience personnel—relationships that would prove to have enormous consequences.
Though he eventually sold the L.A.-based start-up, it wasn’t the stuff kids dream about. “I was more broke when I sold it than when I started it,” he says. Young and deeply in debt, he moved to Chicago, where, bouncing around the city’s burgeoning, mid-recession tech scene, he started to notice something. “A lot of tech startups had begun to pop up,” he says. “And because I’d been through it once, I was very valuable to them. I started to advise them, coach them, just kinda mentor and be of assistance. What I quickly discovered was that the place I was most valuable to them was in the art and science of design.”
The story of ÄKTA is far beyond the scope of this piece. In fact, Roa’s writing a book about it, with a goal toward deating the pervasive romanticism that now pervades the tech scene and highlighting how dicult “making it” really is. Suffice it to say, however, that, by the time he sold the rm Roa really had made it. He had roughly 100 employees and contractors, and counted as his clients such blue-chip companies as BMW, Whirlpool, Starbucks and Motorola.