Building a $100M+ FinTech Venture from Michigan: Ryan Rosett, Founder and Co-CEO of Credibly (Part 1)

Ryan has bootstrapped a FinTech small business lending business from Michigan, raised Private Equity funding to scale, and then bought the PE stake back through a Management Buy-out. Excellent case study!

Sramana Mitra: All right, Ryan, let’s start at the very beginning of your journey. Where are you from? Where were you born, raised? What kind of background?

Ryan Rosett: Thanks for having me on the show. I was born in Detroit, Michigan. I grew up in Southfield, Michigan. Then I was in West Bloomfield, Michigan, which is just a suburb of the city of Detroit. I went to college at University of Michigan and then proceeded to get my law degree at University of Detroit. I never practiced law, but I do have a law license. I’m licensed in the state of Michigan and in Georgia as well.

Sramana Mitra: What time frame are we talking? When did you finish your law degree and enter the working world?

Ryan Rosett: I was in law school when I entered the working world. I graduated law school in 1995. My first entrepreneurial venture was as a second year law student. I opened a coffeehouse in a suburb of Detroit called Birmingham, Michigan. It’s a little downtown district.

At that time, I think there were probably 150 or so Starbucks nationally, with probably a majority of them in Seattle. When I came out of the University of Michigan, there were a number of coffee houses in Ann Arbor but nowhere else. I enjoy the morning routine of going, waiting in line, getting a cup of coffee, sitting down, and reading the paper or whatever the case may be. We just didn’t have that experience at that time. So I ventured into opening a coffee house while I was in law school. That was my first step into being an entrepreneur.

Sramana Mitra: Did you do that full time after you finished law school?

Ryan Rosett: No, I did it for a portion and then I sold it. It was a very successful little coffee shop. It would have lines out the door. It had live music and was open 24 hours, seven days a week. It was quite unique at the time.

I didn’t love retail. I learned pretty quickly that I didn’t love relying on employees to show up. It was just one store, so I didn’t have healthcare to offer employees. I didn’t have stock options to make it more attractive to hire better or higher quality talent. It was just difficult. I determined pretty quickly that this type of business isn’t for me. But it was very successful and I learned. I made a little bit of money and went on to something else.

Sramana Mitra: And what was that something else?

Ryan Rosett: I would say it was an amazing learning experience. I started my second venture, which was a company called Cactus Creek. It was a Microbrewed Beer of the Month Club. This was around 1996 when the internet started and Amazon was simply selling books. We had a website and were taking online orders. This was super early in the world of the internet. We had a phone number. It was called one, eight hundred, two, six packs, which is what you got. You got two different six packs every month. It was a subscription-based business.

I really liked the centralized element of a business where you controlled the end, where orders were taken, very similar to an online business today. You control the merchandise, the shipping, and things of that nature.

What I didn’t anticipate was that it was purely a holiday-based business. It peaked at Christmas and then at Father’s Day. It was a gift-based business. So it was hard during the leaner months to maintain the business from a cashflow perspective. That was probably an experience that I’d say I failed, but it was an amazing learning experience, when I think about it.

Ultimately, we sold it to a competitor, but it was a sale where they’re going to fulfill the obligations for the customers. We managed through the process, but I didn’t make money on the sale. So I don’t view it as a success.

Sramana Mitra: All this while, you’re not practicing law at all.

Ryan Rosett: No, I never practiced law. I did take the bar. I’m still a member of the bar, and I use it all the time. I couldn’t be happier that I went to law school. A lot of people don’t like it, but I thought it was super interesting and enjoyed it.

This segment is part 1 in the series : Building a $100M+ FinTech Venture from Michigan: Ryan Rosett, Founder and Co-CEO of Credibly
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