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How Craig Lewis Pivoted From Hoops To CEO Of A Payroll Tech Firm For The Gig Economy

How Craig Lewis Pivoted From Hoops To CEO Of A Payroll Tech Firm For The Gig Economy

payroll tech
Craig J. Lewis, founder and CEO of Gig Wage, a payroll solution firm that supports gig workers. Photo credit: Gig Wage

Former pro basketball player-turned-entrepreneur Craig J. Lewis has gone from hoops to building a payroll technology company with high-profile backers, and in the process of picking his investors, he said, some were attracted by his audacity.

Lewis is the founder and CEO of Gig Wage, a payroll solution firm that supports gig workers. He has raised more than $13.2 million with backers that include investor and former AOL CEO Steve Case, Foundry Group, and Green Dot.

Before he became an entrepreneur, Lewis played Division 1 basketball in college and professional basketball in Europe. He earned a degree in communication in 2004 from Morehead State University.

To build Gig Wage, Lewis leveraged years of experience working with payroll technology at HR software provider ADP and a stint as chief strategy officer at the facial recognition firm Kairos.

He lists among his achievements selling more than $10 million of payroll and payments software. Lewis is the author of a book, “The Sport of Sales.”

The road to success was not easy. Lewis had to change the original idea for his company — a tough sell for early investors. “It took some sacrifice,” Lewis told The Moguldom Nation. “It wasn’t a selfish decision, it was about the next Black entrepreneur. Now I’m in a position where those early investors who would have been affected by shutting the company down are ecstatic because their ROI is growing tremendously.”

Lewis discussed with The Moguldom Nation how he successfully changed the direction of his company, selected his investors and why he chose Texas for his launch.

Moguldom: You are not new to the startup world; you were a part of Kairos. Can you explain your work there?

Craig Lewis: I was the chief strategy officer at Kairos from 2012 to the end of 2014. That primarily entailed strategy, sales, and fundraising. We started as a timekeeping technology company doing mobile enterprise timekeeping on iPhones, then we pivoted and became a facial recognition company. When the front-facing camera came on the iPhone in 2013, we started selling facial recognition technology.

Craig J. Lewis, founder and CEO of Gig Wage, a payroll solution firm that supports gig workers. Photo credit: Jae Oates

Moguldom: How did the pivot happen?

Craig Lewis: I remember the day we were told we needed to pivot into facial recognition. Funny enough, we were already letting people use our time clock to punch in and punch out for work, and that is how we stumbled upon and realized facial recognition was a huge opportunity. I helped write one of the early versions of our go-to-market process as a facial recognition API. It had been about a year into facial recognition, Q4 2014 or Q1 2015, when I walked away from my day-to-day activities at Kairos, kept my stake in the company, and started Gig Wage. I started it directly after Kairos.

Moguldom: Was that your first executive role with a startup?

Craig Lewis: When I finished playing ball in Europe, I started a company that failed in the sports marketing arena. So, I was an entrepreneur before going down the payroll and technology path.

Moguldom: Gig Wage didn’t start as what it is today, right? What was Gig Wage originally?

Craig Lewis: We were Vistage Payroll, and the idea was free payroll for small businesses. We were trying to be a company like Gusto today with a Credit Karma model and leverage payroll data and give it away to small businesses. Brian (Brackeen) from Kairos, today Lightship Capital, was the one that gave me the idea. I was going to do a modern payroll, but we were on the phone one day, and he suggested I make it free. So for the first couple of years, we were trying to deploy free payroll for small businesses.

Moguldom: Then you changed direction to focus on small businesses or businesses that hire 1099 contractors. Then what happened?

Craig Lewis: That’s how we started. We started off helping small businesses pay 1099 contractors, but we’ve evolved a lot over time. We’ve built this financial infrastructure for all types of businesses. Now, we’re primarily focused on large enterprises and marketplaces where you can push a button, and a gig worker can do the work for you. Large companies use our technology to bring operational excellence and a positive financial experience to their contract workers.

Moguldom: Warren Buffett says that you invest in what you know. You know payroll and stuck with it. When you look at the future of Gig Wage, HR and payroll, where do you see that going?

Craig Lewis: I started at ADP (Automatic Data Processing, a human resources management software provider) in 2008, so anything payroll or ancillary to payroll, I know the underlying technology. For me, I think payroll will serve as a unique base. What’s unique about it is that it is a way to help tens of millions of gig workers. Payroll serves as a unique path into a lot of different industries and other opportunities. Originally, the idea was that the payroll data was important and valuable. So now, if you look across payroll and HR, what is everyone trying to do? They’re trying to help people extract payroll data, employee data, and leverage that data. Most of these APIs connect to ADP, Paycor, or Paylocity. For us, we think instead of trying to connect to all these different platforms and extract the payroll data, we will just build up a user base of payroll data. Now, we’ve got this really interesting gig payroll data that we think will help drive a lot of additional services — things like portable benefits for these workers, insurance, savings, tax, and so much more. We can leverage this gig economy data to empower a lot of these workers, who typically fall in the low- to middle-income consumer range. We believe the payroll data itself becomes super important and we’re tackling and collecting a lot of unique payroll data.

Craig J. Lewis, founder and CEO of Gig Wage, a payroll solution firm that supports gig workers. Photo credit: Jae Oates

Moguldom: How many employees do you have?

Craig Lewis: We’re at 12 full-time employees and by the end of this year, we should be up above 30.

Moguldom: Revolution with Steve Case is part of your investment portfolio from your raise. Did you go through their competition or pitch directly to them?

Craig Lewis: I didn’t do the competition, which I think is great. I went the old-fashioned way and got introduced to one of the partners through a potential customer. An on-demand company, Dispatch, was looking at our technology to pay their drivers, and they were on the fundraising trail. We are a Series A company, and Dispatch is a Series B/Series C company, so they were stages ahead of us. They liked our technology and what we were doing and said, “Hey, you should meet one of our investors.” So I got introduced to Mary Grove, ran our traditional due diligence process, and that’s how they got on the table.

Moguldom: Is that pretty much how you met your other investors as well?

Craig Lewis: We went through an accelerator with TechStars and Western Union. TechStars also invested in the Series A. However, all of my investors ran normal diligence processes. Green Dot Corporation, which is a publicly-traded company, invested off of their balance sheet. After several months of due diligence, the Foundry Group ran an accelerated due diligence process to participate in the round. So, we are taking a pretty traditional approach to it.

Moguldom: How has it been for you, a Black man, trying to raise money?

Craig Lewis: Venture capital is hard to get either way, no matter what color or gender you are. It becomes more difficult as your shade gets darker and your gender is not male. As a Black man, it was already hard raising money. It was more difficult being Black. One of the things I learned about it, though, was it was an opportunity to educate. So, a part of my fundraising journey and running these traditional due diligence processes was helping investors understand how to look at my business and how to look at me as an entrepreneur.

One of the first things I would do to every single investor is ask them how many Black entrepreneurs they’ve invested in? Because I knew the answer. That would always set the table for what level of character the person I am dealing with before pitching. I’m picking and choosing my investors.

I don’t subscribe to the idea that these investors have the magic touch and they get to pick who the great entrepreneurs are. I’m choosing people that fit my narrative and what we’re building.

Craig J. Lewis, founder and CEO of Gig Wage, a payroll solution firm that supports gig workers.

I knew that they didn’t invest in a lot of Black people, but I wanted to hear their answer so I could check their character. I could then educate them on how they needed to evaluate my business differently than what they’ve done on the rest of their portfolio because clearly, they haven’t done it.

I think that audacity and, quite honestly, courage and leadership were some of the things that attracted a lot of people that ended up investing with us. Fundraising is challenging.

Craig J. Lewis, founder and CEO of Gig Wage, a payroll solution firm that supports gig workers.

Asking the question would give me some crazy responses, but I saw it as an opportunity to identify the type of investors I wanted to work with and educate them on the process.

Moguldom: What advice would you give to other founders who are wondering if they should stay on their course or pursue another market opportunity for their company?

Craig Lewis: You’ve got to follow your conviction. For me, the basic service that we’re providing doesn’t matter. What I mean by that is I know that I’m going to be doing something in payroll because that’s what I know, payroll technology. That’s what gives me my edge. When I’m talking to these investors, and they’ve got billions of dollars under management or some of the angel investors have sold companies for billions of dollars, the thing that I’m better than them at is payroll. So I’m going to stay in that lane. Whatever type of payroll solution I bring to the world, we can get there, but the goal is still the same.

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Wealth creation, legacy, pursuing a passion, living out my ambition, going big, raising venture capital — those are all the same goals. As entrepreneurs, you have to check yourself and ask what you are deeply convicted about. How you get to that end goal may change, and you may need to pivot. That’s what allows me to get up every day and do it and why pivoting wasn’t a big deal.

The other thing that’s important about the pivot, though, is when we made the pivot, I was looking for a path forward. We were struggling with the original idea. So as I was out there looking for a path forward, I saw this market opportunity. The interesting thing about being Black is, if I wasn’t Black, I probably would have shut the first iteration of the company down and then started a new company. I was given that advice, but because at that particular time I had already raised three-quarters of a million dollars, I didn’t want to be the guy, the Black guy, to lose these early people’s money.

My conviction about creating wealth, creating a legacy, building something special, and returning capital to my investors is what allowed me to endure through the tough moments.

Moguldom: You could have launched in Silicon Valley or New York. Why did you decide to set up in Dallas?

Craig Lewis: The real answer is that I’m from here, and my mom’s food is really good. The business answer is that I think Dallas is one of the best possible places you can build a business. One of the biggest reasons I’m here today and I was able to last this long, is because of geography, cost of living, cost of doing business, and the cost of talent. I was able to maintain and endure challenging moments and still take care of my wife and kids while building this business in a way that I would not have been able to do in some of the more expensive markets. Now, it may have taken me a little bit longer, but being here allowed me to last a little bit longer. Some of the best business advice I’ve ever gotten is don’t run out of oxygen. Being in Dallas and building my business here in a state and city like this has allowed me to have a little bit more oxygen to get to an inflection point.

Moguldom: What did the next five years look like for Gig Wage?

Craig Lewis: It’s going to be audacious, unique, and spectacular. You know, the only options for us are nine- and ten- figure-type exits, IPO, etc. We’re building a valuable asset to the market. Large corporations are already investing in our organization. We’re an attractive asset, and we’re just warming up. In the next five years, that goal of wealth creation and legacy will build something that people cannot ignore. It will help many independent workers, low- to middle-income workers, to take care of their families. So it’s going to be an exciting journey over the next 16 months. Be on the lookout for a Gig Wage debit card on the back half of this year.

Read more: ‘I’m A Rare Bird Being A Black VC With A Fund Of $150M To Invest’: David Hall, Partner At Revolution’s Rise Of The Rest Seed Fund