Steve MacDonald, a serial entrepreneur, angel investor, and tech enthusiast, embodies a mindset that embraces innovation, resilience, and adventure. Inspired by the Medici family, who once transformed Florence into a Renaissance-era “Silicon Valley,” MacDonald’s entrepreneurial journey unveils a story of audacity and determination that would give the Medicis a run for their money.
MacDonald’s initial journey in Florida was fraught with challenges. “Tampa didn’t have a startup culture or a big investor base,” he reflects. Despite these hurdles, his indomitable spirit set him apart. His zest for adventure combined with his never-quit attitude were the driving forces catapulting success, whether it was starting a company, running the Antarctica Marathon, climbing and skiing the three tallest mountains in Ecuador, or immersing himself in the art of music.
It was also the secret sauce behind his giant early business success, which includes founding and selling three tech businesses: TechHealth, founded in 1999 as a web-based healthcare management company, sold to Apex Group. MamaBear, founded in 2012 as a family & child safety app, sold to Grom Social. And myMatrixx.com, founded in 2001 as a web-based pharmacy benefits management company, sold to Express Scripts. All told, the companies sold for a collective $400 million. Having made his mark as an entrepreneur, MacDonald pivoted to investing. He took a leading role in Florida Funders, a hybrid venture capital and angel investing organization, launched his own angel fund MacDonald Ventures, and invested in dozens of tech startups, marking his arrival as a major tech angel investor.
While fostering growth in early-stage companies, MacDonald and his wife chose to make a dramatic personal shift. Moving his family to a historic villa in Florence, Italy, he spent a year delving into new experiences, cultures, and business ideas, while also taking time to enjoy life and family. In doing so, he recognized that disruption and reinvention are not just for startups but a necessity for the individual entrepreneur as well.
While in Italy, MacDonald spoke at several startup conferences, met numerous young entrepreneurs, judged pitch contests, learned from the inside about the European and Italian start-up scenes and experienced the unique challenges facing young companies trying to launch in different, often more-challenging cultures. These experiences led MacDonald closer to the legacy of the Medicis, a powerful banking dynasty that revolutionized business, politics, and culture in the Renaissance era. Inspired by their example, MacDonald gleaned invaluable lessons in building lasting businesses, nurturing the arts, and establishing a cultural legacy. The Medicis, he realized, made Florence the Silicon Valley of their era – a beacon of innovation and wealth who reshaped the city-state where they lived and far beyond.
“Reading about the Medicis and observing the indelible family crest and legacy on hundreds of buildings and art made me ponder the bigger picture of building businesses,” MacDonald shares. “What mark do we want to leave? Creating a lasting legacy, fostering, investing in and mentoring the next generation of change agents is important and remarkably challenging. But it’s a goal worth pursuing.” This experience deepened MacDonald’s commitment to transforming Tampa into a powerful hub for startups and dynamic businesses.
Looking ahead, MacDonald foresees a more hands-on role with the companies he invests in. His vision for the future involves strategically investing in a handful of high-potential companies and nurturing them into rapid-scale ventures, creating a sort of mini-version of Berkshire Hathaway’s vastly successful holding company.
Through his unique fusion of entrepreneurship and adventurous spirit, MacDonald is leaving a lasting imprint on the world of startups. He already oversees a portfolio of more than 100 early-stage companies, eight of which have become “unicorns” with valuations exceeding $1 billion each.
Like the Renaissance Medicis, MacDonald is more than just an entrepreneur or investor. He’s a patron of innovation, a conduit for change, and a passionate participant in life’s grand adventure. Just as the Medicis forever changed the face of Florence, so too is MacDonald reshaping the business landscape in Tampa and beyond.