Athletes of Influence: Craig J. Lewis evolves as an entrepreneur and angel investor

Craig J. Lewis launched Gig Wage with a mission to offer a reliable, convenient way for 1099 workers to get paid. But in the process Craig has learned the power of what he coins “compounding interest.”

Craig describes how as a fintech entrepreneur, he is constantly learning and evolving. As an angel investor, he is constantly learning and evolving. And the two are intimately connected.

“My work as an entrepreneur and operator in Gig Wage helps me be a better investor, advisor, board member. But then doing those things actually then help me be a better operator and entrepreneur,” Craig said.

The investment ecosystem

Craig knows first hand the challenge of securing venture capital, a process that can be profoundly challenging for Black founders. He has raised over $29 million since founding Gig Wage as a fast and efficient payment platform for employers and gig workers.

As a leader in the fintech industry, Craig says investing and deploying capital in his company helps him better figure out what he likes investing in. As an entrepreneur, he can quickly spot a startup with potential. “It’s a good breeding ground to be a good angel investor,” Craig said.

Craig contemplated private wealth management. But in the end, he opted for a more hands on approach. He handles his investments directly and doesn’t put money in public holdings. Everything is private. Through angel investing, he has learned the differences between wealth preservation and wealth creation.

“So the entrepreneurs are really this kerosene and this lightning rod of value and wealth creation, which actually makes you the best person to spot alpha and make investments. The power of being an entrepreneur and operating gives you a really unique seat to become a world class investor. But nobody’s talking about this, right?”

As a seed investor in Black, brown and women-owned businesses, Craig routinely draws on the lessons he learns to inform his work as CEO of Gig Wage. After writing a check, he asks himself: Would you write a check for your business today? Would you introduce an investor? And what questions would you ask yourself?

When Craig speaks at investment conferences, he encourages entrepreneurs aspiring to be investors that you don’t have to write a big check to get into the game. But you do need deal flow. Craig argues that writing even a small check for seed funding or Series A funding can be enough to exercise that investment muscle and start to build out a network that fuels deal flow.

With his own tech startup to run, Craig doesn’t have time to waste when searching for prospective investments. He hunts for founders with domain expertise at startups where he can bring immediate value.

“I’ve done this long enough that I’m seeing companies fail and shut down. I’m seeing companies pivot. I’m seeing companies succeed. I’m seeing people growing faster than me. I’m seeing people growing slower than me … You have the whole ecosystem at your disposal. So it’s a pretty powerful tool for an entrepreneur,” Craig explained.

Becoming a smarter CEO and board member

Craig has served on various boards, including recently joining MassChallenge’s global board of directors as the only member that doesn’t live in Massachusetts. Over the years it has changed how he runs Gig Wage board meetings.

Operating from the mindset that the board should never be surprised during a meeting, Craig for more than two years met one-on-one with each member beforehand. But once he joined other companies’ boards, he shared that modus operandi with founders and CEOs. To his surprise, they called him crazy.

“I was like, ‘None of you guys do this? And none of you guys are even interested in doing it?’ They’re like, ‘We would never do that.’ And so I started to unpack this, but I’m learning from these other entrepreneurs. And we have so much better board meetings now that I don’t do that. They’re much more organic. There’s much more discussion and debate. Everybody doesn’t feel prepped. But I had to learn that.”

On the flip side, he approaches his role on the boards on which he serves differently as a fintech startup founder. In a Gig Wage board meeting, Craig is always on the lookout for meaningful recommendations rather than off-the-cuff suggestions. Even more valuable is when a board member can alter the way he or she thinks about a particular topic in a meaningful way.

“Now, as an investor or a board member, that’s how I think about it. I’m like, ‘Craig, you got a million suggestions. Do you have any recommendations?’” Craig explained. “That’s what I’m focused on trying to give because I know that’s what is the most valuable.”

That added value is just one of the reasons Craig continues to push himself to be a better CEO through continued angel investing. It creates a dynamic environment where he is continuously improving in both roles. He advises that your company will never pull you into the next phase as CEO. “You have to pull the company to that place,” Craig explains.

“Every investor update I get, every new deal I look at, every data room I’m in, every board meeting I sit in, every deal I say no to, I’m getting better, and you can’t get that by only operating the company … it’s just all compounding,” Craig said. “The more I can do the better I get.”