Episode 36: Monica Wooden’s journey: A leadership story

Oscarlyn Elder:

Starting a company from scratch and later selling it in a headline-making deal is the dream of many entrepreneurs. For some, like Monica Wooden, that’s not the end of the story. The rest of the happily ever after comes about when that success turbocharges the opportunity to live and share your values and purpose. I’m Oscarlyn Elder, Co-Chief Investment Officer for Truist Wealth, and this is I’ve Been Meaning To Do That, a podcast from Truist Wealth, a purpose-driven financial services organization. We appreciate you listening.

In the year 2000, Monica co-founded MercuryGate International, a leader in transportation management software. She grew it from the ground up during the challenging days of the dot-com bust, building a culture focused on shared success and meaningful innovation. In 2018, she and her business partner sold the company in a major private equity deal, enabling not just their own success, but creating substantial wealth for many early investors and employees.

Since then, Monica has channeled her time and resources into philanthropy and community impact, funding scholarships, supporting sports programs, and creating vital resources for women in need, especially those in rural communities. Today, we’ll explore her journey from the early sparks of leadership to building a high-growth company to creating a legacy that reflects her values.

Monica Wooden is a current client of Truist Bank and Truist Advisory Services Inc. No cash or non-cash compensation was provided, nor was there any compensation arrangements in place for this guest based upon her involvement in this podcast. Any comments or references to taxes herein are informational only. Truist and its representatives do not provide tax or legal advice. You should consult your individual tax or legal professional before taking any action that may have tax or legal consequences. Monica, welcome to I’ve Been Meaning To Do That.

Monica Wooden:

Thank you, Oscarlyn. It’s a pleasure to be here.

Oscarlyn Elder:

Monica, I’ve been excited to have you on our podcast ever since we met at an event in Florida earlier this year when I had the opportunity to really talk with you and to learn some of your story. One of the things we talked about was how much of your leadership spirit was developed at an early age. What or who were some of the influences?

Monica Wooden:

Teachers, coaches, parents, brothers, and sisters I had growing up. I was the youngest of five, so I think as my siblings would say, I got all the breaks. I was a pre-Title 9 baby, so there wasn’t a lot of organized sports for girls back then, but I always followed my brother around, always had a ball in my hand, and everybody would pick me over him, so it was kind of fun. But then in 1972 when Title 9 became law, the explosion of sports for women was just astronomical. So, I played four sports in high school, two sports in college. So, you can imagine, and every one of them involved a ball, so I always had a ball in my hand. So, I would say my mom was big mentor for me in that she really never went to my games or any of my practices because she worked really, really hard.

My dad also, both were laborers. He came from a small town in the Finger Lakes in New York. Everybody was a blue-collar worker. I had some of the most amazing teachers’ guidance. I ended up being class president for four years, student council president for a couple years, and I kind of look back on that, and all of those experiences of staying kind of that busy and being involved in school leadership positions really set the stage of even when I went off to college and was captain of my teams and president of our fraternity. So, I think I had a lot of good teachers, a lot of good coaches, and good parental supervision.

Oscarlyn Elder:

So, through all of those channels, you were able to really build confidence in your leadership skills?

Monica Wooden:

Yeah, very much. I think sports is... It could be drama, it could be music, it could be art. It’s got to be something that takes a person’s interest and builds that underlying confidence, and sports was my ticket.

Oscarlyn Elder:

At some point, you ended up in your career at IBM and you’ve shared with me that that time at IBM was really quite formative. What were you involved in that shaped your path forward?

Monica Wooden:

Yeah, it was a great formative part of my working and going to a company like IBM, you get to see what success looks like. So, when I got to IBM, they actually were in dire straits. So, this is when they were just starting the transition to move from a product company to a services company. So timing was terrific for me. I got to start a couple of new businesses inside of IBM at a young age. I had the most incredible IBM executive mentors and actually learned some of my greatest achievements, I think, came from really understanding how the IBM attorney worked with the sales and marketing and executives to put win-win deals on the table, especially back when it was really important for IBM to be transitioning into a services business. It was a magnificent eight years of experience at IBM that really laid the groundwork for my next journey.

Oscarlyn Elder:

So, you started a technology company in 2000, and that was really during the dot-com bust, and I’m assuming it was definitely not easy during that particularly challenging time. What were the toughest challenges and how did you push through those?

Monica Wooden:

The first challenge, of course, was the funds needed to start a company. Because the dot-com bust, I mean, I had a business proposal where I was looking at needing $17 million to do this company and there was no money around. I mean, people were offering like $300,000 and we’ll take 30% of your company and you have to use all of our accounting services. I mean, it was kind of a joke. So sometimes not the best situation turns out to be a real good situation.

I went to friends and family, and I asked friends and family if they had $50,000 increments hanging around that was maybe in a savings account or not doing much, and they wanted to invest in a startup. So, between friends and family, myself, and my partner, we raised $1.2 million. I worked without pay for five years, so that saved a lot of money. We were able to bring on 20 initial employees, and when your back is against the wall and you’re building a new product, you build it fast, you get it out there, you get clients. If you could believe this, we were actually profitable in our second year.

Oscarlyn Elder:

So you were able to go to friends and family, and you had the confidence to pitch them on your idea.

Monica Wooden:

Actually, the funniest thing that happened in the journey was they never wanted to sell to get out. They wanted to go as long as I went. It does show though that these are not high investment folks. These are folks that took a chance and believed in something and ended up working out for them.

Oscarlyn Elder:

Absolutely, and it also says something about your family and the way in which you were reared. Your family had the savings to be able to invest in you in that way. I’m assuming that might go back to your parents and the way that you were raised.

Monica Wooden:

Yeah, this is really a lesson that I think that I wish all youngsters or young adults could learn. You always have to pay yourself first. You have to save something. So, I grew up in probably lower middle class at the time. My mom would always save something, give something to others, and then provide for what we needed, and it was a routine. It was always that way. So, when I started my working career, I would buy savings bonds for my kids. Every paycheck. I would always save. So, I graduated from graduate school at 23, so from 23 to 40, that’s 17 years.

I saved enough money to be able to work without pay for five years, invest in my startup and support my family as well. So that means you have to have good habits. Everybody in my family had the same mindset. I was the only one of the five that actually worked for a corporation. So, they were all entrepreneurs themselves, so they used to rag me a little bit that I was the only one that didn’t have my own company. And then eventually at 40, which I think is the average age in the United States for folks to start a business, and we all know why, right? You’ve identified a problem that needs to be solved. It’s hard to find something when you’re so young and you haven’t gone through a lot of life experiences. You have to have some capital, some money saved.

Oscarlyn Elder:

Absolutely. I was reading a book, beginning to read a book this weekend that mentioned that as well, Monica, that we have this perception that successful entrepreneurs are just out of college or college age, and that’s just not the reality.

Well, I love hearing about your personal path to success, but I know a strong motivation for you over your career has been the idea of shared success. We’ll come back and talk about that in just a moment.

Monica, you refer to win-win-win deal making. Could you explain what this concept involves and describe its origins?

Monica Wooden:

Yeah, this was a lot of the stuff that I learned at IBM, especially from the executives that I work for and the attorney that your customer has to win first. The company has to win, and typically there’s involved partners. And so, you have to structure deals where everybody’s going to win. And when I looked at that deal-making back when I was at IBM, I structured a contract that it didn’t matter whether the customer wanted to host the software themselves, have us host it, buy a perpetual license, pay a subscription fee, pay a transaction fee. I put it all in one contract, you pick, so wherever you are.

Another really, really important thing that I did: I never had a contract that was beyond month to month, so my customers could terminate in a month’s notice. There was no long-term contracts and people said to me, “Well, why do you do that?” It’s real simple. If my product doesn’t work for them, they can terminate. If they have a merger or acquisition or something going on that’s going to change their dynamics, need to let them out of it. And we had a 95% retention rate. So that goes along with this win-win-win. Everybody’s got to win, and they got to win all the time consistently in the game.

Oscarlyn Elder:

That’s very powerful and it strikes me that in order to create the win-win-win, to your point, you’ve got to be creating value constantly with what you’re delivering to the client. MercuryGate is notable for the high percentage of women it employs both in technical and senior leadership positions, roles where women have historically been underrepresented in the tech world. Was that a specific goal for you and how did it happen?

Monica Wooden:

There was no specific goal. When you start a company, you just want good people at good value who work really hard no matter what they look like. That’s really all you’re going for. But what happens along the way is when you’re out there, especially a female CEO, and you’re talking to prospects and you’re talking to people that you want to hire, it brings different people to the table that want to be involved that maybe haven’t seen a female in a non-traditional type of role, especially in transportation or in software. Certainly, that’s changed a lot. I would say in the 25 years since starting MercuryGate, I think the profession of supply chain professionals is almost now dominated by women.

And so, these young professional women would come to MercuryGate and understand that, “Hey, we are in a high dynamic area. It’s an area in which we haven’t been that strong in. At the same time, here’s a terrific innovative company with no BS, nothing.” Half of our employees work from home. The other half worked in our central office, but it was also a good workplace environment. And I think that also attracts a lot more people. But then when you hire one, they have a network and then they have a network. And this is to me how companies are built and how you get diversity of thought.

Oscarlyn Elder:

How did your leadership style evolve throughout your ownership and leadership of MercuryGate, maybe even stretching back to IBM or earlier?

Monica Wooden:

I was actually fired from IBM. I really liked what I was doing, and I really liked my customers and my team, and I didn’t want to leave. And new executive comes in. It’s not any different than new head coach comes in in a sports team, they’re going to get rid of everyone of bring on their own assistants. So, it’s not unusual for that to happen. So senior executive comes in, kills off all of his executives, wants to bring his own team in, and I didn’t want to go.

So, I held my ground for about a year, and he finally pushed me out, but I had good compensation package. And that was the impetus for me to actually learn about a problem in transportation management software where only the biggest companies could afford to solve that and automate it. And I wanted to build the product where no matter the size of the company, they could all afford software would allow them to optimize and automate their shipments. And the internet was truly the best means because when you deal in transportation, most of the participants in transportation are outside of your company, and so the internet makes it easy to do business and connect people.

So, a multi-tenant, web-native architecture from the timing was perfect. But that firing allowed me to say, “Hey, let me go do something now that, I saw a problem and now I can solve it.” And then at MercuryGate, good or bad, I was kind of what they call the rescue dog. We didn’t have much turnover. Sometimes that’s good, but sometimes it’s also not so good. I viewed that if a person wasn’t successful in their job, then I wasn’t doing a great job of mentoring them or giving them enough education or support to be successful. I definitely managed downward. I think the biggest thing came when I brought in a board of directors. I wasn’t a big fan of managing up. To me it was like a waste of energy. Now people laugh, right? Because typically CEOs need to adjust. They have to be able to manage upward to their stakeholders, their shareholders, their board members. So, I had to change my leadership style a bit and not be such a rescue dog.

Oscarlyn Elder:

Yeah, I think that’s an important call-out. What I’m hearing you say is that you had a comfort zone. You really had an area that you were completely expert in, which probably ties back to all of your sports involvement, all of your history, right? You were really good at coaching folks up and mentoring people, and that was your comfort zone, but ultimately you also had to learn the skill and lean into managing upward, interacting with your board of directors, interacting with your shareholders because that’s what you had to do to be successful in this different, more complex environment.

Monica Wooden:

Yeah, exactly.

Oscarlyn Elder:

The sale of MercuryGate in 2018 put some dollar signs and numbers I think on this idea of shared success. And in many cases they were big seven-figure numbers and some of your early employees and investors became millionaires out of that deal. How did the idea of shared success factor into your decision-making during the sales process?

Monica Wooden:

A lot of the employees that came on board, especially from the dot-com bust where there was a lot of people unemployed, they took lesser salaries, but we gave them stock options. So, I would say over half of the company, so when we sold the company, there were 300 employees, so there were about 150 employees that had stock options, and they were treated as founders of the company themselves. They would even buy their options so that they knew when the company was going to sell, they would have long-term capital gains rather than ordinary income.

That’s how confident these folks were. At the same time, when you go that long, people can get tired. So, one of the things I did about five years earlier was I took the top 20 employees and most of the initial investors and paid them out. So, we took the $1.2 million that was initially invested, paid those friends and family out, and then I took about 20 of our top employees that had been rowing for quite a long time and let them cash in about 25% of their equity. And it was important for me to explain to them that they’ve worked so hard in selling companies, you really need to think like a hockey stick.

It takes a long time to build the value, but once you’re there, it goes up really, really fast in comparison to years. But giving them that small cash-out earlier allowed them to get a second wind and to really row harder. I felt really good doing that. It’s like taking chips off the table. You’re safe now. You’re good. Let’s go and let’s see if we can run this thing up.

Oscarlyn Elder:

Monica, with all your hard work and success, you earned the opportunity to craft a substantial philanthropic legacy for yourself. We’ll talk about how you’ve approached that opportunity when we come right back.

Monica, selling MercuryGate, the company that you co-founded, was a huge milestone for you. Why did you choose to sell the company when you did?

Monica Wooden:

I think it has a lot to do with when you build something, if you feel that it’s solid and mature and the people around are excellent, it means that you can let someone else go the next leg. So, if you’re going to build something great, you have to be able to have it run and managed by other people. You can’t always be there. And so one of the big things for me was in 2018, I felt that nobody could wreck this product. No one could destroy this company. You often hear about these stories, right? You sell and then five years later, I mean, right at IBM, we did this all the time. I didn’t want that to happen to this, so we felt that we moved it along so that the software was so good, so solid, there were so many customers all around the world that were using it, and the team was terrific.

They were still committed that now was a great time to put this in the hands of the next leader. To be honest, we didn’t ever put together a formal package to go out to sell the company. We got a lot of unsolicited offerings, and those unsolicited offerings started coming in in December of 2017. This was kind of crazy. We actually had 13 unsolicited offerings and made a decision in August of 2018 and picked one. We didn’t pick the highest bid. We picked a company that we knew had a good CEO that I really liked, that I felt would do a really good job of taking the company through the next path. And it worked out great because last year the company was finally sold to a strategic buyer that actually looks exactly like what we had tried to build when I was at IBM. You talk about life going full circle. When I look at the company that now has the software and the size of them, that’s exactly what we were intending to build in 1996 at IBM.

Oscarlyn Elder:

Right. Almost like a boomerang moment is kind of how I’m envisioning it in my brain.

Among the projects that you funded, one of them is the Monica Wooden Center for Supply Chain Management and Sustainability at the University of South Florida and also scholarships honoring your family members. How do you decide where to focus your philanthropy?

Monica Wooden:

If you think about your life, the first 20 years, you learn how to learn. The next 20 years, you learn by looking around you and people that you work with. Then the next 20 years, you’re the owner and the lead mentor, so you’re working hard and lifting others and making sure that your 300 employees’ families are all doing great, and then the next chapter you look at enabling others to do the work. So that’s where I came up with … the University of South Florida, worked hard to get accreditation for a master’s in bachelor’s in supply chain. And I felt being local and living in the area … it’s a school that has 50,000 students, half of them are first generation college, which I am. But this would enable students that go to this prestigious university to get degrees and to go into professions of supply chain.

So, we find internships, of course, we support scholarships and find jobs. It’s been very rewarding to watch the center grow over the past seven years. As far as other areas for purpose, I wanted to also give back to where I came from. We’re all transient, but we’ve all come from someplace. When my mom passed away, it was important for me to leave a legacy about her, and so I did STEM scholarships for female at my high school. And then my father who was where I learned how to hunt and fish, and he was a mason, so I did a 10-year scholarship around someone who enjoys hunting and fishing. Whether they go to college or go into a trade, doesn’t matter. We do another 10-year scholarship for someone who is in the construction/architecture type of field, a high school student, and so I’m always looking and seeing where we can enable.

Probably the project I’m most proud of is when I was in Tampa, I went to a meeting or a charity event around supporting women’s shelters because I always wanted to give to women’s shelters. And I walked away from that event saying, “I have never seen a city with the most unbelievable, charitable, excellent facilities for women’s shelters ever.” This is an A++ organization. So, I went back with the knowledge of what that looks like and went back to my hometown where the sheriff there happened to be a high school friend, and we talked about they didn’t have a shelter. They only had a 1-800 number, and so I worked with them. We found a huge house that can support 10 families at a time, and I was able to buy that and support them in getting that off the ground. It’s been three or four years.

The success has been amazing, and that’s in a rural town that we forget about. These shelters are so important for women who they don’t know where to turn. What I saw in the Tampa area, again, just like how I saw things done at IBM, gives you a picture of what it could be. We actually called the place the House of Rose, which is my mother’s middle name. For the folks who run that shelter home, I’m enabling them to do better work. For the folks that run the center at supply chain, I’m enabling them to do a great job for our youth, and so it’s all about me using money to enable and lift other people to do the heavy lifting now.

Oscarlyn Elder:

That’s incredible. Monica, what you’re doing is creating real impact in the world in multiple ways, but in areas that really speak to your heart and to your experience and you’re taking your business lens and applying it to the work that you’re doing in the community. What advice would you offer to others who are or who hope to be in a similar position of wealth and leadership when it comes to living and sharing their values?

Monica Wooden:

We seem to be a society of gratification. We want something today rather than looking at the future. You have to be able to look at the future, and if you do that, it allows your values to run your entire life. I don’t want to die and then just have a bunch of money that goes someplace. I want to see it today. I want to see the people who are going to be successful in lifting others. You have to understand that this whole thing about compound interest, it’s a simple thing, but it’s amazing how we forget about it.

We want the newest of this and that. I buy a car and I drive it until it doesn’t work anymore. I still have a car in my garage that I bought in the year 2000. It’s 25 years old. It gives me great joy instead of buying another hot rod to give that money to some of these very purposeful places that have a chance to lift everyone, and I love doing it. There’s so many great projects out there. At the same time, it takes really good people that you’re investing in to do these projects, and I think that’s the number one lesson for me. You have to look at the people and they have to have similar values as you.

Oscarlyn Elder:

Well, there were a few words that you said there that resonate with me and that is I heard joy, values, and people. And what comes through is that you have really found joy in doing your due diligence and finding the people and the institutions to connect with that align with your values that you’re able to help enable to go make a specific impact.

Monica Wooden:

Yeah, that’s right, and it does take some work. It takes time, but it’s really joyful to give.

Oscarlyn Elder:

Monica, you’ve turned your business success into a lasting legacy that affects so many people, and I know there’s much more to come. We’ll get some final thoughts from you when we come back in just a minute.

Monica, thank you for sharing your story with us today. Your early lessons in leadership, the way you built and sold a company and then created a meaningful legacy is a great example of the intersection of financial planning and values that we talk about here on the podcast on a regular basis.

Monica Wooden:

Well, thank you very much for having me. I really appreciate being part of your podcast. I enjoyed the questions that you asked, and I hope together I’ll see you down the road.

Oscarlyn Elder:

Absolutely. Before we completely wrap up, we have a tradition here on I’ve Been Meaning To Do That. We ask our guests, “What’s the one thing that you’ve been meaning to do that you haven’t done yet and that you’re willing to commit to do now with our audience listening?”

Monica Wooden:

Wow, put me on the spot. That’s great. One of the things since I’ve been retired is I’m trying to replace bad habits with good habits, and these are new habits. I have four bad habits, and so what I’ve done is I’ve picked up four new habits to replace those four bad habits, and I think I’m doing a pretty good job of getting there. I’m still not there, I want you to know, but the good habits are really good. I spend a lot of time with audiobooks.

Oscarlyn Elder:

Nice.

Monica Wooden:

I spend a lot of time doing puzzles.

Oscarlyn Elder:

Awesome.

Monica Wooden:

I spend a lot of time at the gym. I coached youth sports for 15 years and was part of a little league board of directors for 10 years, so I spent a lot of my time on the field coaching and mentoring during my years, but now I replace that with now I play softball.

Oscarlyn Elder:

Awesome.

Monica Wooden:

I golf, I hunt, I fish, I do all those other things, but I added softball, puzzles, and then a good workout routine to the gym to replace those nasty four habits that I had, so I’m still working on it.

Oscarlyn Elder:

Well, we wish you all the best of luck as you continue to embrace those good habits and exercise those more frequently. It sounds like wonderful endeavors all the way around.

Monica, thank you for joining me today, and listeners, I want to thank you as well. If you liked this episode, please be sure to subscribe, rate, and review the podcast and tell friends and family about it. If you have a question for me or a suggestion for this podcast, email me at dothat@truist.com. I’ll be back soon for another episode of I’ve Been Meaning To Do That, the podcast that gets you moving toward fulfilling your purpose and achieving your financial goals. Talk to you soon.

Speaker 3:

Oscarlyn Elder is an investment advisor representative, Truist Advisory Services Incorporated. Any comments or references to taxes herein are informational only. Truist and its representatives do not provide tax or legal advice. You should consult your individual tax or legal professional before taking any action that may have tax or legal consequences.