Angel investor looks to lead the next generation, fund dreamers and make money in the process

Steve MacDonald sees his mission as pretty straightforward.

He wants to find dreamers and innovators, smart people with good ideas and the desire to see them through. And then he wants to give them the money they’ll need to see those ideas come to life and, in the process, make a better world.

Simple, right?

For anybody else, the answer would likely be no. But to hear MacDonald talk, what he’s proposing and what he wants to do with his life is as easy as can be.

One of the reasons for that is he doesn’t ask anyone to do something he hasn’t already done.

And MacDonald, 53, has done a lot.

Along with being an angel investor, a trusted mentor throughout Tampa Bay’s startup community, he’s also a marathoner and mountain climber.

MacDonald made his fortune after founding myMatrixx, a pharmacy benefits company, in 2001. He grew it into one of the largest companies in the industry and then sold it in 2017 for $250 million. 

Rather than sitting on his wealth, MacDonald, the Business Observer's Top Entrepreneur in 2013 who has more than $400 million in exits of companies he founded, started MacDonald Ventures.

The firm, as well as the mentorship he does throughout the area, is a way for him to indulge in a passion for finding entrepreneurs with change-making ideas he can back and watch grow.

The website for the firm says MacDonald Ventures is “more than investors, we embed ourselves at inception, partnering with inventors, challengers, adventurers to cultivate leaders.”

But MacDonald himself put it in simpler terms: “I want to help build the next generation of change agents and surf in their wakes.”

“As an investor, what I’m looking for is those early-stage entrepreneurs, with lots of energy, lots of ambition, creativity,” MacDonald says.

“People that I see that have ideas and the willingness, the fortitude, to take these ideas to market and build them.”

For MacDonald, helping these entrepreneurs is a way to pass on the knowledge he’s developed over the years and help make lasting change.

He sees this as a personal responsibility. There is too much negativity in the world, he says, and what the world needs is people with positive ideas that will help improve the lives of others.

The firm invests anywhere from $50,000 to $1 million in companies at all stages of the start-up process.

Among the companies MacDonald has invested in over the years are MammaBear App, an app that allows parents to monitor their children’s online activities; Booksy, an app that allows you to book health and beauty services; and Skillshare, an online learning community offering classes for people looking to embrace their creative side. Overall, he has a portfolio of over 100 angel investments, according to his website. 

MacDonald says the desire to help people get their business started either by investing money or being a mentor is rooted in a desire to do good in the world. And that desire is rooted in his upbringing.

Orphaned at a young age, he says his adoptive parents’ love is probably what makes him so open to helping others.

“If my parents hadn’t adopted me and taken a chance, who knows where I would be,” he says. Helping others now “is my way of paying it forward.”

Other than giving money, one valuable of way of giving back is passing on the lessons from his failures.

And he’s had his fair share.

A company he started called AccessLife failed when the internet bubble popped in 1999. And then he was fired from a second company he founded, TechHealth.

But, he says, his biggest mistake — a term he doesn’t like — is when he didn’t have the confidence or experience to trust his own instincts.

MacDonald says he’s faced situations when a gut feeling was telling him what to do — but he ignored it. “And then the outcome was what my gut told me it was going to be.”

Over the years he’s learned to identify the feeling and to have the confidence to trust it. And while he can’t teach someone to trust their instincts, he believes they can be taught to identify the feeling and learn to gain confidence in it.

That, though, is just one small lesson of the many he passes on to those he mentors.

But it’s hard to just sweep it away. That’s because confidence is so important for startups, which face the near-impossible road of taking a germ of an idea and creating something the world didn’t even know it needed.

And, that is the essential point of what MacDonald does. He knows smart people can come up with solutions and he sees it as his mission to make sure they stay focused and never lose sight of the goal.

“Nothing worth having is easy,” he says. “You’re going to have lots of obstacles along the way, it’s part of it. Don’t blame anyone except yourself and learn from those obstacles. Apply those lessons and move on.”

Oh, and it doesn’t hurt that everyone gets to make few bucks along the way.