A Serial Entrepreneur’s Journey into FinTech: Felix Rodriguez, Founder and CEO of finally (Part 1)

Felix has done nine ventures and sold several of them. He is currently building a venture-funded,
AI-enabled FinTech venture. Really intelligent, scrappy maneuvering in various alleys of online entrepreneurship.

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

Felix Rodriguez: Thank you for having me. I came to the United States when I was five years old from the Dominican Republic (DR). My grandma had arrived before us, and she had about thirteen kids in the DR.

Sramana Mitra: Wow.

Felix Rodriguez: After she got to the US, she’d get enough income to be able to justify getting a visa for each one of us kids. So, by the time it was my dad’s turn to come over, I was five. I was very fortunate to have gotten here at a young age and grow up as an American.

Sramana Mitra: What year was that? When did you come?

Felix Rodriguez: I believe it was towards the end of 1985.

Sramana Mitra: And what did you do for education? You came to Florida, right?

Felix Rodriguez: A lot of us from the DR mostly go to New York. I was in the Bronx.

Sramana Mitra: All right. Okay. What education path did you follow?

Felix Rodriguez: The American dream for my family – my uncles, my dad, and I lived this, was entrepreneurship. Every single one of them had their own business, and I saw the impact that they had. That stayed with me forever, but I pursued a traditional going-to-school route. My real interests from a very young age were always computers. I started coding HTML when I was twelve years old and putting stuff on the web. I became a network engineer and spent about five to six years working at a bank dealing with all the systems, auditors, and regulators.

Sramana Mitra: What happens after that?

Felix Rodriguez: I remember in the summer going to my CEO and telling him about my idea of helping other small businesses get professional email and an online presence. I said, “Do you mind if I use the extra server we had?” He asked me to go ahead.

I would say it was probably 2004. The initial concept was that I start off with a directory of businesses and local businesses. Then I quickly found out that I was the first sales guy. I developed the website and the application and then also spoke to the clients. I learned that they wanted more professional email. They wanted to use a professional domain and they wanted a website. I told them that I should provide that service.

By the end of the summer, I had signed up over 3,000 small businesses to the directory. I went to my boss, and I said, “Barry, I’m going to be leaving.” He goes, “Kid, what are you talking about?” I said, “Well, I started the thing. Thank you for the server. I now have over 3,000 customers and I’m generating more revenue, more income than from my salary here at the bank. And it looks like it’s a really good opportunity.”

He told me, “You’re not going to leave empty handed.” He ended up being my first investor and a lot of my other coworkers were also investors in my first venture. So, I was starting in a place where there was already a lot of money. I didn’t have to go find money.

 Sramana Mitra: What did you do with that business?

Felix Rodriguez: We ended up growing it, expanding it, adding additional products. So, we launched a website hosting and design for small businesses, grew that to about another 5,000 customers before it was sold to what’s now called Deluxe Corporation. We ended up running that for about almost two years and grew it to about 50 team members before exiting it.

Sramana Mitra: What kind of revenue level did you reach with it?

Felix Rodriguez: The revenue was less than ten.

Sramana Mitra: Ten million revenue in two years?

Felix Rodriguez: Yes. It’s still definitely one of the fastest growing companies that I’ve been a part of.

Sramana Mitra: When you exited it, what kind of multiple did you get? What did you sell it at?

Felix Rodriguez: That’s a story for another day, but at the end of the day, I don’t think I made the best decision there. I think this happens to young entrepreneurs. When you start a company, you don’t know how far you can go. I was very young. I thought I should sell, but people are hard to recruit and the relationships I built with those key people were lost.

So, if you’re going to go short, don’t do it. Then the other thing is, by the time it was sold, I personally had a three-year non-compete clause. These are the things you don’t know and don’t think about if it’s your first time going through it.

We should have sold to a different company that we had an offer, and I should have gone to work and be part of their team, right? The other offer was from a public company. I think I would have learned a lot from doing that sale as opposed to doing a sale where I was not a part of that future.

That’s what I learned. Although it didn’t set me back, it certainly helped me with my future other businesses? I had a nice story to tell that I sold my first startup. For the next two that I built, I was also able to raise capital and sell them as well. So, it helped me in that sense.

Sramana Mitra: So, how much did you sell that for?

Felix Rodriguez: I’m going to say it’s not enough. The second offer would have been game-changing, life-changing, but the first offer that I took was not.

Sramana Mitra: You were not the 100% percent owner of that company. You had investors, right?

Felix Rodriguez: Absolutely, I started off with investors.

Sramana Mitra: Did you get enough money in that exit such that you had some capital to work with in the next venture?

Felix Rodriguez: It opened up a lot of doors and a lot of connections and it gave me some time to go work on something else. But I’ve never been the type to take long breaks. I immediately started something in a month or two.

Sramana Mitra: No, I’m not talking about the time to take a break. I’m talking about time to seed fund your next venture. See the thing that works well if you have an exit early on is that you have capital with which to seed your next venture for serial entrepreneurs.

Felix Rodriguez: I did not do that till probably my fourth startup because of my partner in the first business. He was really attached to me. He was much older, and he wanted to keep doing things together. I also felt committed to him. I didn’t need to go raise money because I had access to some capital.

Sramana Mitra: I see.

Felix Rodriguez: So, I think that was the benefit of it that I could raise capital.

Sramana Mitra: There’s a reason why you are skirting the question that I’m asking you. I’ve asked you three times. How much did you sell that company for? You don’t want to answer that question is what I’m gathering.

Felix Rodriguez: I feel like I probably shouldn’t answer it considering there were kind of two offers and maybe I could have done better, you know?

Sramana Mitra: All right. What year does this bring us up to when you’ve sold the company and you’re back with the clean slates?

Felix Rodriguez: I’ll give you the specifics. During that time, we also had a couple other startups that we were starting. So, we were able to work on those immediately. By the time we sold WebImage, that was January of 2007.

This segment is part 1 in the series : A Serial Entrepreneur's Journey into FinTech: Felix Rodriguez, Founder and CEO of finally
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