What makes a good business partner, first enterprise client, and selling your company with Mark Fleming Jr. (Founder of Signature Closers)

Callan Harrington 00:01
You're listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here.

Callan Harrington 00:21
Today's guest is Mark Fleming. I'm really excited about this. Mark founded Signature Closers, which was acquired by Stewart Title in February of 2021, where he now serves as the Senior Operations Director. Mark's got his hands in all kinds of ventures. He's an angel investor, a co-founder of a company called Talent Share, and the managing partner at MM Capital. Mark, I don’t think there’s anything you're not doing right now, which is exciting. Welcome to the show!

Mark Fleming 00:51
Thanks for having me, Callan. I appreciate it.

Callan Harrington 00:53
Yeah, in your own words, tell us what you're up to right now.

Mark Fleming 00:56
To your point, a little bit of everything. So, in February of 2021, our company, Signature Closers, was acquired by Stewart Title, and that was quite an interesting learning experience. You know, it's a Fortune 800 company, publicly traded, so the due diligence process alone taught me so much that I'm still applying today. I’m now working there in more of a strategic sales role, helping to integrate our technology and systems under the broader umbrella of this large company. We’re a small fish trying to blend in with a huge corporation. I’m involved in strategy, helping build out our e-closing solutions, and keeping our team on the right trajectory.

Outside of that, I co-founded a company called Talent Share. It's a startup with a very interesting idea; we’re connecting collegiate athletes to youth athletes through a marketplace or app for lessons and coaching. I'm passionate about that. The business was actually created during a coffee chat with a friend of mine, Dan DeLucia, who was the pitching coach at Ohio State at the time. We were discussing NIL (Name, Image, Likeness) and how there are a lot of big deals out there for football and men's basketball players, but other athletes aren't getting the same opportunities. Dan mentioned to me that he had a pitcher who was all Big Ten but was bussing tables for $15 an hour at a local country club. Dan had suggested to that pitcher, “Hey, you ought to think about teaching lessons. When I was in school, I made a couple hundred bucks an hour getting four or five kids together, charging them $40 or $50, and teaching them how to pitch.” But the student-athlete had no idea where to start. He said, “That sounds great; I’d love to make $200 an hour, but where do I market myself? How do I find parents?” And this was an all Big Ten pitcher, so we’re not talking about a random person. That’s what motivated the creation of Talent Share. I also have two daughters who participate in sports like lacrosse, swimming, and field hockey, which don’t get as much exposure as others, so this is our way of bringing opportunities to those sports. We’ve also partnered with Justin Inacio, a former Ohio State lacrosse player who is now a professional lacrosse player, and he’s on our team, which is really exciting.

Then, there’s MM Capital, where I’m currently working under an LOI (Letter of Intent) with an organization that I’m looking to bring under my umbrella—sort of a holding company where I can oversee and invest in the business, almost like a chairman role. My goal is to build out a portfolio of companies in industries I understand well and can add value to by partnering with good operators and leadership teams. So, yeah, that’s what’s on my plate right now.

Callan Harrington 04:03
Wow, no shortage of things to do, for sure. You’ve got all sorts of cool things going on right now. I’ve heard you mention before that you’re an “accidental entrepreneur.” What does that mean? Where did that come from? Where did this all start?

Mark Fleming 04:18
That’s a great question. Actually, I was on a podcast last week, and I was sort of accidentally on that podcast by myself. Justin, who I just mentioned from Ohio State, set us up on the Shrimp Tank podcast here in Columbus to talk a little bit about Talent Share. That morning, I texted him, “Hey, I’m running a few minutes behind,” and he called me, but I missed his call because I was trying to get out the door. He texted me back, “Hey, I’m really sick. Can’t make it.” I was like, “Oh geez, he set this up. Am I supposed to go in or not?” So I went in anyway, and they asked a little bit about how Signature Closers started. That’s when I came up with the phrase “accidental entrepreneur” just last week. It wasn’t like I sat down one day and said, “Okay, I’m going to be an entrepreneur. I’m going to start this company, raise capital, or put my own money in, and knowingly go into that journey.” It was one of those things where—it's kind of a long story, but I'll try to make it short—I was in college...

Callan Harrington 05:17
What did you want to do?

Mark Fleming 05:18
Well, you know, I didn’t know. I was 21, 22 years old. I started Signature when I was going into my senior year at Miami University. I tell people I kind of majored accidentally as well. I liked real estate and law, and I still do. I was able to take courses in those areas under my finance major at Miami University in Oxford, Ohio, and that’s why I went the finance route. It wasn’t that I thought, “Oh, I want to be in investment banking or work for some big company.” That wasn’t on my radar. I just liked finance, real estate, and law, so I could use those courses toward my major. Sounds good. So, to answer your original question, I didn’t really know what I wanted to do at that age. I did grow up in an entrepreneurial family. My dad had some experience in real estate, buying and selling houses, and managing rental properties. I’d seen the flexibility but also the challenges in that world. Looking back, my parents tell me stories about school fundraisers where I would broker deals or sell things, so I guess I had an entrepreneurial spirit, but I never had the intention of starting a business. It’s funny how it played out, and that’s why I consider myself an “accidental entrepreneur.”

Callan Harrington 06:39
It is interesting. I definitely wanted to start a business, but I didn’t know where to go with that. So that’s interesting. And what I find so funny about your story is that you didn’t want to be an entrepreneur, but you founded a company in college, which is not a normal thing. What led you to the founding of that company?

Mark Fleming 07:00
It initially started as a summer job. I was going into the summer before my senior year, looking at internships in the financial world—Ameriprise Financial, Northwestern Mutual—companies that offered unpaid internships. There’s nothing wrong with that; you can learn a lot. I’m very entrepreneurial now, but I think having a couple of years of experience in a business, especially a startup or small company, is helpful when creating your own business. My advice to those graduating and looking to start businesses is that there may be some who are qualified to jump right in if they surround themselves with the right people. But having a couple of years of experience working within an organization where you’re seeing and doing a lot before starting your own business can be helpful. There’s nothing wrong with those internships.

Back to my story, my dad suggested I consider becoming a notary. He had connections with title companies, and I could make maybe $100 per closing, which sounded good versus an unpaid internship. So I became a notary and started doing closings in the middle of nowhere—like, “Hey, there’s a farmhouse 20 miles outside of Oxford at 9 pm.” I’d do that closing because no one else wanted to. Through that, I built a reputation as someone willing to work hard. I went to work for Cardinal Health, thinking I was done with the notary business, but I had met someone who had a network of notaries around Ohio who would refer deals they couldn’t cover. My dad suggested I think about starting a side business where someone else handles the day-to-day, and if they’re a notary, they get first dibs. Maybe there’s some type of revenue share or commission based on the business they handle. It was a bit of creative thinking.

I found a partner, but being young and naive, I eventually had to go in a different direction. She went direct to one of my clients, and suddenly I went from doing 30 deals a month to zero. My mother-in-law eventually jumped into the business and ran the day-to-day for several years. That was our path. I joke about it being “BC” (Before Chris) and “AD” (After Development). My mother-in-law, Jennifer Kays, ran the business day-to-day in the background while I worked at Cardinal. My next job was in Employee Benefits, where I stayed for about four years. I found that job because I did a closing during my lunch break at Cardinal for a company in that space. I thought their office was cool, and they suggested hiring me. One thing led to another, and I ended up taking a job there, moving to another company shortly after due to some issues at the original one.

I spent a lot of time in Employee Benefits and became an expert in the space. I regularly dealt with an ERISA attorney and learned so much. At the same time, the side business eventually became a full-time business. I had experience in several areas and could step in and run it full-time. So, I was at Cardinal, gained an Employee Benefits background, and then made the leap to a software company in Cincinnati, where I met Chris Chapman, my technical co-founder. That’s the backstory leading up to when I jumped full-time with Signature.

Callan Harrington 15:19
One of the things I find interesting, and I’ve seen this many times, is that from the outside, you look like a young guy who had a great exit from the company—an overnight success. But it’s always a steady progression over a number of years, with setbacks and changes. It’s not just this giant hockey stick. Is that accurate?

Mark Fleming 16:00
Oh, 100%. Overnight success, to me, doesn’t exist. I’m not saying people don’t do it quickly and scale fast, but even then, there’s probably been a lot of groundwork laid before you see that scale and growth. For us, this was a part-time business for almost five years. I’ve been with Signature for 15-plus years now, and I went full-time in March 2012. It took about eight years until we sold the company in January 2020. It was definitely a slow and steady organic growth. But we did hit a point where we ramped up pretty quickly over two or three years.

Callan Harrington 17:22
How did you find your technical co-founder?

Mark Fleming 17:27
I met Chris at a company called Blue Spring Solutions in Cincinnati. The side business was becoming a lot of work, so after hours, Jennifer would schedule closings using a Google Calendar and an Excel spreadsheet. I would come home, take the orders placed for the day, and copy and paste the information into QuickBooks. Then, I’d send invoices to our customers and create bills to pay the notaries. It doesn’t seem like much, but when you’re working a full-time job, have two young kids, and a young family, it was a lot. I was ready to say, “This may not be the best fit. I need to move on.” But Chris had heard about the business somehow and asked me to grab lunch at BW3s to talk about it. I shared my challenges—needing a calendar, easier payment processes, and easier invoicing. He jotted notes down on a napkin and said, “I think I can build a website for you.” We laugh about it now because it was just what I needed, and we came to an agreement where he would grow into the business if it worked, and if not, no sweat off my back—no money exchanging hands. It was a win-win because he had upside, and I didn’t have downside. It turned out to be the perfect partnership.

We didn’t even know it at the time, but when I first met Chris, I didn’t realize that his brother Tanner and I had lived together at Miami in a duplex. It’s a small world. But Chris built the website in the fall of 2011, and we released Closing Manager in October or November of that year. That’s how we met.

Callan Harrington 20:08
I’ve seen this in venture-backed companies as well. It’s a great approach to wait until you have the business established before bringing on a CTO or even sales staff. You don’t know what to automate or what your needs will be. Sometimes you bring on a partner who doesn’t align with the vision or skill set to operate the company you want to build. But you were more selective by then, with a clearer understanding of your issues and whether Chris’s skill set aligned with solving them. Is that correct?

Mark Fleming 21:06
Absolutely. I think I got very lucky that Chris and I have complementary skill sets. There were so many things that happened between the time I met Chris and the acquisition that, had they not played out exactly as they did, who knows what we’d be doing today? But I believe there was a big element of fate or divine intervention in our story. Chris and I connected, and he just happened to be the right co-founder for me. He had experience in business process management. It was funny—the first company that approached us after we released Closing Manager was using Resware, which Chris had worked with extensively. We had already discussed building out integrations to streamline processes. That first client started sending us 1,000 orders a month, and we decided to integrate with Resware, which turned out to be the right decision. Most larger national title companies started using Resware, so we were lucky to have Chris’s experience and the right connections. That integration became a big part of our growth.

Callan Harrington 24:20
That first enterprise client can be a huge game-changer. You mentioned that Chris was the right partner, and you had already experienced the opposite with a partner who didn’t work out. Partnerships are hard. It takes time to flesh out how to work together, especially when equity is involved. What gave you the comfort level to bring on a partner after a negative experience? And what made this partnership work so well?

Mark Fleming 25:34
To be honest, I was young, naive, and a little desperate. I was at a tipping point, ready to give up on the business because it had become too much—a headache after hours, issues that needed resolving. So I thought, “What’s the downside risk here? If it doesn’t work out, I’ll shut down anyway.” That lack of downside risk gave me the comfort to take the chance. My familiarity with Tanner from Miami and knowing Chris had a good reputation in our company also helped. Chris had a strong focus on business process improvement, which aligned well with what we needed.

As an entrepreneur, I’ve read quite a few books, and the Traction series, particularly the Entrepreneurial Operating System (EOS), talks about the visionary and integrator roles. Many great companies have had that combination—Steve Jobs and Steve Wozniak at Apple, for example.

Callan Harrington 27:19
Just to clarify for our listeners, the visionary is typically the CEO, thinking three to five years down the road, often focused on sales and marketing. The integrator is more like a COO, handling operations and ensuring the business runs smoothly. I’m a big believer in EOS, especially for small and mid-sized businesses.

Mark Fleming 27:50
Exactly. For us, it was the perfect marriage. I’m definitely a visionary—I’m diagnosed ADHD, and while there are challenges, I consider it a superpower in terms of creativity and innovation. But it’s easy to get pulled in many directions. Chris, on the other hand, is very stoic and focused. He kept us on track. I remember suggesting ideas like building out an automated email and text system in 2012, but Chris insisted on staying laser-focused on what we were good at. To his credit, that focus paid off. We eventually built a supplemental product in 2018 called Sync, similar to what our competitor Snapdocs was doing. But had we gone down that road in 2012, it would have been too soon and taken us off course.

Chris’s focus on what drives revenue, improves customer experience, and cuts costs was key to our success. We spent most of our time on those three things.

Callan Harrington 30:30
So you got your first enterprise customer, which took you from 100 to 1,000 monthly transactions. How did that change things?

Mark Fleming 30:42
It was pretty hectic, especially before the integration. Around the holidays, I was working crazy hours, entering orders, and scheduling closings. But it opened my eyes to the fact that there was a lot more business out there. When Chris and I first sat down, we thought 2,000 signings a month would be a great business. We got this client sending 1,000 orders a month, and we were like, “Wow.” We started setting higher targets—2,000 signings, then 8,000 like one of our competitors, and eventually aiming to compete with Snapdocs, which had raised hundreds of millions of dollars. We didn’t realize how big this could be. We thought it would be a cool little side business with a couple of thousand orders, but here we are, years later, having done over 62,000 transactions in a month.

Callan Harrington 32:20
That’s incredible. So, did you make the decision to exit, or did it happen organically?

Mark Fleming 33:13
It definitely happened organically. We had some inbound interest. The first time we tried to sell the company, it was because we were overwhelmed. In 2013, we had a customer who was one of our larger clients, and we offered to sell the business for $100,000. It was worth more than that, but we were frustrated with the stress of dealing with notaries, cash flow, and the day-to-day challenges. Thankfully, they said no, and we had to solve those issues in other ways.

In 2018, we had a company owned by a big PE firm that expressed interest in acquiring us. But we grew so quickly that we were too big for their creative structure but not big enough for a full acquisition. So that fell apart. Another PE firm in Philadelphia approached us about complementing a remote online notary platform they were building. But when they looked at our margins, they realized we didn’t fit their portfolio needs.

In July 2019, we started getting more serious interest from companies that saw us as a strategic acquisition.

Callan Harrington 38:12
You eventually sold the company to Stewart Title. How has life changed since then?

Mark Fleming 38:18
It was a meaningful transaction personally and for the company. It’s opened up opportunities for investing, giving back, and helping others through advisory roles. Going through the acquisition process taught me a lot, and it was a great opportunity for us as a family and as a company. Stewart Title’s infrastructure took a lot of stress off my shoulders—accounts receivable, accounts payable, HR, and benefits are all handled by centralized offices now. That’s been a huge relief.

Life has changed in terms of reduced stress and having more time to focus on things that matter to me, like building out a portfolio of companies and working on projects I’m passionate about. It’s been a positive experience overall, and I’m excited to see what comes next.

Callan Harrington 41:15
That’s amazing. One of the things we always end on is, what advice would you give your younger self? If you could do it all over again, what would you say?

Mark Fleming 41:27
Trust your gut and surround yourself with people who push you to be better. As I’ve gotten older, I’ve become more selective about who I spend my time with, and I focus on people who make me better. That’s been a big part of my growth. When you’re younger, it’s easy to spread yourself thin, but now I have a clearer understanding of who and what are most important to me.

Callan Harrington 42:16
So true. Everyone has an opinion on what you should do, but you have to follow your gut and do what gives you energy. There are a million ways to make money, but you have to enjoy what you’re doing. That’s excellent advice. I appreciate you taking the time, Mark. This was a fun conversation, and I’m excited to see what comes next for you.

Mark Fleming 43:08
Thanks, Callan. The last thing you mentioned reminded me of Jim Collins’ hedgehog concept—where your passion, skill set, and what people are willing to pay for intersect. That’s advice I’d give my younger self too. It’s been great talking with you, and I’m excited to see what’s next for both of us.

Callan Harrington 44:05
Absolutely. Thanks for coming on the show, Mark.

Mark Fleming 44:08
Thanks for having me.