Leadership Strategies For Professional Growth And Success With Todd Fleming

We all want to achieve our goals and be successful. We want to make a significant difference and drive change. But are we taking the steps needed towards professional growth? Lance chats with Todd Fleming, Vice President and General Manager for Legends Global Sales. Todd has taken on several high-profile roles in his career. In navigating that path, he touches on the need for flexibility and agility, working with like-minded people, and the importance of grit. As he said, “I wasn’t necessarily the best, but I was willing to outwork everyone else.” Looking to advance your career to a higher position? Todd Fleming gives you the ladder to reach it.

Listen to the podcast here:


Against the Sales Odds and Todd Fleming Review Leadership Strategies For Professional Growth

I’m excited about this episode. Not only is this person I’ve done business with over the years, more importantly, but he’s also a good friend of mine. We shared a lot of goals, laughs and drinks over the years. We even fell asleep one time at a San Antonio Spurs game both in the suite because we were tired after a long day. Without any further due, I like to welcome a good friend of mine, Todd Fleming. He’s with Legends.

He’s the VP and General Manager for their Global Sales Division. Todd, I’m so excited you’re on. We have a lot of roads underneath this, so welcome to the show. Talk to everybody because we get a lot of people on this because there were some people in sports entertainment and some people aren’t. Talk about your job. What’s your role with Legends.

First of all, thanks for having me on and hopefully, people find this to be a good little session. In my role at Legends on the Global Sales side, we do everything from ticketing, hospitality, and all the way down to special catered events and tours inside of sports facilities and some of the vertical towers that we have globally.

My role, quite honestly, is I view it as I’m still a sales guy. What that means is, new business development is critical for everything that we do at Legends. I spend a fair amount of my time doing long engagements along with sales cycles on business development because obviously, in the project world, those things maybe 6 to 10 years in the making before they come out of the ground.

The other side of what I do is, once we do have an engagement on the revenue side, the management team that hits the ground and is the catalyst for the work that gets done and the success that we have on the ground. I act as a support system. From a managerial standpoint, they flow in through me, from the Global Sales side, but I view my job as supporting them being a sounding board for them. Mixing things up with them from time to time to ensure that we’re doing, on a day in and day out basis, what we’ve told the client that we would execute for them as part of the engagement. I do that against domestic work as well as international.

In your world, you’re coaching sales leaders and sales teams on the ground on a lot of the projects that you’ve been involved in and creating a partnership with. You’re a live fire at all times. You’re a promise keeper, execution and at the same time communicating that back and forth to the client and making sure that the ground forces are getting done when they needed to get done.

It’s even a little bit bigger than that too and this probably not going to be rocket science to most people in this session, but when you’re an agency, you answer to the client, but you also have to answer internally. Legends is very much a big organization at this point, but we still run close to the vest with everybody playing a part in any project that we have.

It’s not only communicating to the client and ensuring that we’re doing what we’re supposed to be doing. It’s coaching the management team on the ground to communicate upward, sideways, downward, but then it’s also my job too. It’s to make sure that I’m communicated internally where the additional opportunities are inside that engagement. Communication is essential to everything that I do on a daily basis.

From talking to you, it’s always live, many live executions at all times. The premise of the show is to have people talk about like, “How did you get here? How did you get to this spot?” Bring us back. Todd, enter sports and entertainment because right now, high-level consulting and leadership, how do you even land here?

My journey has been fun and I love talking about it because it’s a little atypical, but it’s worked for me and I’ll even go back even before sports. My first job coming out of college, I was in it my senior year of college. I’ve got my start in the entrepreneurial space. If you go back to 1999 to 2000, dot-com was everything.

I had an opportunity to work for a brand new dot-com. We had the worst domain name that you could ever think of was EverythingDecor.com was the company. It’s a massive domain name. In hindsight, you would have shortened that. It was one of the first times that call it flooring, office supplies, anything that you could think of to set up an office or inside your house was being asked to be put online, that people could purchase.

Our financial backer was Flooring America, which at the time was the third-largest retailer of carpet in the United States. They still exist and I’m not sure if they’re as big as what they were. They decided to enter the dot-com business. Me as a young 21 and 22-year-old helping launch this site, it gave me the perspective of what it takes to be successful in business. I was a sales guy, almost like a buyer per se, but I was walking in Dalton, Georgia, where all the textile mills are that produce products like Shaw Industries, Mohawk carpet. They’re all headquartered right there.

You’ve got to do something unique. You have to do something different to differentiate yourself. 

My job at 22 years old would be walking to these executives and sometimes the owners of these companies and talking to them about the internet and talking to them about how placing their products online was going to be the wave of the future and how it was going to benefit their business. Almost 10 out of 10 times, these guys didn’t have a computer on their desk.

It is very interesting that you are in a space that wasn’t well-defined because you end up later in your career doing the same thing for Legends.

I’ll speed this up a little bit, but yes, if you fast forward from 1999, 2000, 2008, 2009 and 2010, when Legends was starting to be talked about. It’s much older in 2010, when we launched the Global Sales side, but it felt eerily similar.

I didn’t realize that you were in that early, but you did a redo. You’re a buyer. It’s a very competitive space. Where do you go from there? What’s the next move for you?

I went through the boom and fizzle. We decided to launch. We were making some money, but we had to go through our next round of financing. In a weird way, learning the financial, aspects of the business, I got a taste of it early on, but we didn’t get financing the second time around. We went from 50, 60 plus employees one day to literally zero. At that time, I had some opportunities coming out of school to get into sports. I played basketball. It’s a small school basketball, and then my brother was a pro baseball player and so for me, it was like, “I wanted to make my name somewhere else.” That’s why I went the dot-com route.

When the company shuttered to me at that point, I was like, “You need to do something that you’re passionate about.” Like something that you love, you care about and you understand to a certain extent. What it taught me was I understood business and sports could go together. I came back to Ohio. I was living in Atlanta. That’s where the dot-com was.

I came back to Ohio. I didn’t know anybody in the sports industry, but I got into contact with my professors at Mountain Union College, which is now the University of Mount Union. They knew of a job that the Cavaliers were sourcing as an account executive, so ticket sales. It made sense. What I did was I went through the formal process, submitting your resume through an HR process. I felt like I had a little bit of sales knowledge and I said, “I’ve got to do something to differentiate myself.”

Have you done the other thing for about a year?

Yes, but I’m still 22.

You were coming right out of school. You had some experience.

I had a little bit of experience in the grind, and this is where it helped me. I said, “You’ve got to do something unique and different to differentiate yourself.” I went through the formal process so that way I didn’t offend anybody, but I called the organization and tracked down who the VP of ticket sales was at that time, which was Jim Van Stone. Who’s now at Monumental.

ASO 39 | Professional Growth
Professional Growth: It’s not only communicating to the client and ensuring that we’re doing what we’re supposed to be doing. It’s coaching the management team on the ground to communicate well.

Fortunately for me, a lot of this probably was luck. He answered his phone. Maybe the assistant was off doing something else, but he answered his line and he gave me 10 to 15 minutes. We wrapped for a little bit, and he gave me the time. He said, “No guarantees, but I’ll get you the interview.” He dropped me at the director of sales and I had an interview the next week live and in person. Fortunately, I didn’t put my foot in my mouth during that interview and was offered the job.

You came in with some clout, and there’s no doubt whether we know this or not, Van Stone’s probably telling people, “This guy gave me a call,” which is part of the course of your career, which is interesting. You go in the Cavs. Obviously, at that point, there’s a lot of people on that introductory team at the Cavs that are still in sports and are players. You came in with that crew. What were you like as a salesperson? If you’re manager, if I had them at the moment, where were you a pain in the butt? What were you good at?

What I focused on as an athlete, I wasn’t the best athlete either. I wasn’t the best basketball player, but I outworked people. To me, it was a little bit of the mentality of, “I knew time management. I knew when I was at my peak and I set my day up for my calls and appointments when I was at my peak.” I wasn’t number one on the board.

It’s self-management. At the end of the day, it’s to know yourself, people are worried about all these other factors. It’s so cliche to say control the controllable but that works like managing yourself.

The self-evaluation that a salesperson or a manager has to go through, the internal discussion that you have to have with yourself is to identify. To me, it was always, “What are you great at? There are some things that you’re not good at. You got to work on those, but if you can put yourself in a position every day to do the things that you’re great at, you’re going to have more success.”

Tell me what you weren’t good at.

I didn’t know what this could be as a career. To me, the notoriety that you can say, “I work for a sports team,” I probably fixated more on that, than buckling down early in my career to try to say, “Where do I want this to go?”

It was cool to say, “I got a job in sports.”

No doubt. The route I took where I was a pain in the butt, was probably that. I probably could have produced more revenue, could have been more efficient in the conversations, but I didn’t have a mapped out goal for myself that early in my career. I’m sure I caused my managers a ton of stress because I was missing opportunities. I wasn’t taking things seriously.

Activity that produces a really good end result is the only thing that matters in that environment. 

That’s exactly what I was going to say. They were probably sitting there going, “He doesn’t take it seriously. It’s not seen as a career.” You’re laying bricks. You’re not building the cathedral. You spend time in the Cavs. How long were you there and what’s the promotion there?

What’s interesting because Van Stone left about eight months into my tenure there, he went out to Philly. He went 76ers or Flyers. That’s when Chad Estis came in, which he’s been on here before. When Chad came in, the whole dynamic of ticket sales at the Cavs changed. It went more from telemarketing, which was the early-2000s. Chad was a corporate seller. It was about building relationship, rapport and going more from a B2B standpoint.

That got me back into the time in Atlanta and it felt more comfortable. Trying to develop a relationship with somebody go out of the office, be more outbound. It changed. My evolution there was, he went from selling tickets and groups and single nights to having the ability to sell sweets more of a premium product. Chad came in and we created some different club spaces inside the arena.

How did you change when Chad came in? How did your view change?

It was all about me. To me, I’m now in a position where I’m more comfortable. Doing things over the phone was never my strong suit. Being in front of somebody and having this type of dialogue and reading body language, is where I’m the best. When we had the ability to go out of the office and set up meetings, that is when my mentality shifted and I could then see from myself. This is where I wanted to be in my career, and then I wanted to flip to the managerial side of the business because I wanted to go figure out how to set these businesses up.

This is right around the point. You’re a few years in, at this point.


There is a spot because that’s when I first had met you and then you took off. Your career started to accelerate. You got opportunistic. Where’d you go from there?

I turned down a few things early on because I had a son that was living in Ohio and I wanted to make sure that was all lined up before I pursued career opportunities. I went from the Cavs to Miami Heat. We get LeBron in Cleveland.

LeBron fell due to Miami.

I was even going out of Miami before he got there. One of the things that happened to mind. I went to Miami to run their inside sales department, and which again was putting together entry-level staff members, recent college grads, new people breaking into the industry and trying to change the culture of how things were sold in Miami.

The title there is what, Todd?

I was the Director of Inside Sales when I first started. By the time I left there, I was Director of Sales. I oversaw inside sales have shuttered. I’ve overseen group sales on the arena side.

Inside sales shuttered because LeBron came.

No. That happened later. I was there having some great success during Dwayne Wade’s first year, but Pat Riley had just retired and Stan Van Gundy was the coach. They started 0 and 7, but we ended the year, 42 and 40. That whole group had come together. Those young guys, it was Lamar Odom, Dwayne Wade, Skip to My Lou, Caron Butler. That group had come together and gone 42 and 40.

I need everybody to follow this. You went from the pure seller and jumped right in the leadership. Where did you skin your face because that’s elite? All of a sudden, you have 10, 15 people under you and you are managing an army of one before that. What was the hardest thing for you there?

ASO 39 | Professional Growth
Professional Growth: There are some things you’re not good at. You have to work on those, but if you can put yourself in a position every day to do the things you’re great at, you will have more success.

The hardest thing for me to learn was the cadence of the executives upward. How did they want to be communicated to? I always try to approach the staff in a genuine way of like getting to know them and trying to create communication with them that globally they understand the expectations, but how it’s implemented and how they’re held accountable, that’s more on a one-to-one basis.

I felt like that was good. That’s a little bit of the point guard in me from back in the basketball days is managing a group, but making it individualistic. Where I skinned my face and learn quickly is how do you communicate to executives. It’s not long-winded. It’s very succinct, a lot of bullet points, but this learning how each individual, what type of information they wanted to receive and when did they want to receive it, that was the hard part for me breaking into management.

When you think about managing a team and you become a higher performer because you got promoted. You got a shot. If somebody was marketing you and you were marketing yourself, so they thought a lot about you, what pissed you off about salespeople that you realized? I look at leaders and people that can lead sales, what are some things that rubbed you about salespeople? You talked about managing up, which is most people do not even fathom how to master that. They’re not mastering that by mistake and trial and error. What ticked you off about salespeople are grinding you a little bit.

This may sound a little weird, but I think salespeople are like stand-up comics. They are a little insecure. The confidence that salespeople exude isn’t always real. Behind the scenes, there’s a little bit of, “Am I doing the right things? Am I not?” What I saw early on in my managerial career is that they would give up too early, meaning on the conversation on the sale. That was a confidence thing. It boiled down to, they’re not asking the right questions or they’re not talking to the right people.

That became where their confidence took a hit, and they would give up on the process or the discussion way too early. They didn’t know how to pivot, to go find who else made the decision or the right solution to the objective. That was the thing that pissed me off and still pisses me off to this day because a lot of salespeople give up.

It does and they give up early on themselves too. If they can’t go to the shortest tree, the lowest hanging branch and pull the lowest apple off, and all of a sudden, you’ve got to get up a ladder, some of them give up because it’s not easy. Sales is not easy. From there, what’s your next move because you’re there for another two years or so?

I was there for two seasons, but it was not even a full two years.

This feels like two years, no matter. That’s the seasonality of that business. Where do you go?

I’ll give you a quick story, too. It’s the worst managerial moment that I’ve had in my entire career. I’m taking over some other staff and have a depth of army now with people. We get Shaq which changes the world. He’s coming off 4 straight, 5 straight NBA finals appearances, that type of scenario. Obviously, he and Kobe didn’t get along, but he’s still the biggest name in basketball at this time. He comes to Miami. Money’s not an issue in that town. We actually sell ourselves out of a job.

The inside sales team was influential in a catalyst in the sales. Once we got Shaq, I had to let all 24 of those people go in one fatal swoop. What it taught me, and it became a lesson later on, is that people matter, and trying to solve that issue in the future has become part of who I am. Unfortunately, for me to continue to grow and to reach the heights that I wanted to do, managing the arena and group sales side, which were the only things that were being sold at that point for the Miami Heat, wasn’t going to be the way that I got to my goals.

I developed four things that I wanted to do. I wanted to work for an NBA championship-caliber team. I wanted to work with a player or a team that drove sales. People think it’s easy when a team is great. It’s not because the expectations of your marketplace change adjusting to that. I wanted to go through a city and state relocation. I thought that those were four things in the world of sports entertainment that teach you how to do business differently. I said, “I’ve already worked with two great players, LeBron, Shaq and D Wade. I can check that box. Championship. If I stay in Miami, we’re probably going to be that.”

When things aren’t going the way you planned them, do not give up. Learn how to pivot and find the right solution to the objective.

Maybe I can check that box, but I got fixated on the city and state relocation. I thought like going through politics and setting up finances and how do you do that? Fortunately, at that time, the Nets were moving from the Meadowlands to Brooklyn. They were in the beginning stages of that. I had been recruited by the NBA to go, so I opted in. I moved from Cleveland to Miami, get rid of all my winter coats to get into Miami.

What’s the role with the Nets then?

I took what would be perceived as a lateral move. I went to take the inside sales role and director of inside sales. By the end of my tenure there, I had overseen inside sales. I had overseen a senior level staff and I got paid to be the first one to open up our New York office. I had three different staff that were six miles apart but doing astronomically different sales routines.

I was there for three years. The role was to build the base in Jersey. We had a good team. We had Kidd, Carter and Richard Jefferson. I have a good team, built a base. That way, it was sufficient enough to move to Brooklyn. Again, it was recruiting New York, and how do you get them to participate for four games or more at the Meadowlands?

Without getting into names and people, you’re a high D CEO/President. There’s no doubt, those were trials by fire. What did you learn about your sales leadership there because you hadn’t got much differently?

What I took from that is, “You better know your crap at all times.”

Who are we talking about? Is it Brett Yormark?


Brett’s a very high D.

He moves at a pace that most would fall down after 24 hours and he keeps it going 365.

You got to be on your game and he’s moving quickly, hard and fast, and there’s not a lot of excuses.

It was, “You better know your stuff at all times, and it can’t be superficial. You better drill down into the detail and be able to communicate what the next steps are.”

You’re dealing with a much different leadership team than Chad Estis. What did you learn there and how did you evolve?

To me, it boiled down to activity matters but an activity that produces a good end result is the only thing that matters in that environment.

It’s not an activity for activity’s sake.

No. It was, “We’re going to be active because it’s the right type of activity that produces money coming through the door.”

You and I have talked about this a thousand times. That’s what some sales leaders that don’t get. There’s a difference between activity and being busy and busy work as opposed to profitable action. At the end of the day, who cares how many dollars you make, if you’re making a sale.

That’s all he was about and that ownership was about. Quite honestly, that’s the market of New York. It’s a Metropolitan area like, “If you’re not making money, what are you doing? Why are you even here?” He challenged on a day in and day out basis, the headcount, the personnel and we did it to ourselves too. It’s like, “We have to have the high performance here,” because we’re essentially fending the fan that has supported this team for decades. We’re moving six miles away, but they’re never coming. They don’t do that. You’re moving literally, it was six miles door to door but that marketplace to this marketplace, they won’t go.

ASO 39 | Professional Growth
Professional Growth: You better drill down into the details and be able to communicate what the next steps are.

I don’t know if that’s the Hudson River, East River, that minus with The Great Wall of China. That territorial boundary there is a different marketplace.

It’s a mentality thing too. There are people in Brooklyn because that’s where they’re at now, and that became the fan base, but you have to attract Manhattan. There were people in Brooklyn that were upset that you’d spend time in Manhattan because they live in Brooklyn their entire life and have never gone to Manhattan.

Would you say that you became more of an assertive leader?

Yes, you had to.

I hate the word aggressive, but I love the word assertive because you and I have talked about that for decades.

It had to be more assertive and it had to be done with purpose.

It starts getting interesting for me because you have a couple of little trips here. You got to pay attention to the sled here because now there starts to be some movement. That next move, was it Charlotte?

No. The next move is back with Chad in the Dallas Cowboys.

All of a sudden, the age of the new stadium comes into play because at this point, the only NFL stadium, it’s built from when you start is like Lincoln Financial Field.

That’s it, yes.

Now, Dallas started to build a stadium, and they weren’t getting great press either. It was going to be the most expensive anything. You get recruited back by Chad as The Four Horsemen of The Apocalypse. Doug Dawson, Al Guido, Todd Fleming, who am I missing? Now, all of a sudden, the fourth person of the apocalypse isn’t there, it’s the three-headed monster. You guys have to bring on this massive staff to sell the stadium that’s being planned out. Talk about that experience.

What this experience taught me is the pre-planning to launch a business. It was all about the tactics. There are two faces. It’s all about the tactics, strategy and the things that you do to be ready that put us in a position to have success. The way that we even hired people. If you remember, we did group interviews because we needed to find charts, straight out of the gate. We knew where this pricing was going to go.

We needed to find the best possible talent in a very quick and efficient manner. Even the way that we went about hiring and interviewing people to be part of the staff was astronomically different. It’s the way that we trained. The sales centers were not as grandiose. The way that the sales center was developed, how we officed in a trailer situation, it became the pre-planning and the focus that you have to have to launch something was different. It’s still something that carries on. That’s where the focus goes.

You started the Nets and freaking get it done at all costs, guerrilla warfare if you need to, talk about how you started to develop more strategy? I remember you at this point and there is so much strategy. To be recruiting, training and developing salespeople or strategies, there’s a strategy to product knowledge. There’s a strategy to the phases by which we’re going to sell because this has never been done on the scale before. To give perspective to everybody, your first task, how many new suites were there and how many club seats? This has never been done before at this point.

The managerial approach and style of people are different. 

There were 300 suites and 15,000 club seats inside 80,000 fixated seat building that could expand it to 100,000.

It’s suites at that point. The most you would ever have been like 80. This had 300 suites.

No doubt, it’s 300 and then it ended up being 370 at the very end.

That concept hadn’t been fully vetted out, meaning it wasn’t a new vote to have club seats. You’re talking maybe 300, 400 at Mercedes Benz Club at the Cavs, as opposed to now you have to sell out this massive number. What was the number your team had a hit with those club seats?

There were 15,000 club seats that were there. The total COI, the Contractually Obligated Income that we were shooting for was 500. The entire stadium had a PSL concept on it, except for, there were several thousand seats in the upper corners that did not. This is where strategy started to make sense to me. Chad was like, “You got to be in Steven Jones’s hip pocket.”

As we were trying to develop how to phase this, trying to hire people, we were actually selling during this timeframe as well. I traveled around with Steven to breakfasts, lunches, sometimes the occasional cocktails. He would set up the meetings with some of the most influential people in the region. You would be meeting them over breakfast and he would go through the spiel of what it would mean to their family, and then he would look to me.

He would say, “Tell him what’s happening at the stadium.” How do you tell a story about a hole in the ground? How do you paint the picture through renderings and visuals? It boiled back to a lot of what you and I have always talked about. It is, “I’ve got to start to figure out what’s happening in the mind of the person on the other side of the table.”

It goes back to what you were doing.

This isn’t show and tell. With the images of the stadium, we all know what AT&T has become. It was beautiful. It looked even great on renderings. It didn’t matter when I was getting ready to ask somebody for $150,000 per seat before they even got a chance to buy their tickets. It was before I could even get to that point, I had to figure out all the things that we know to do. What were they doing? Why were they doing it? What are their objectives? What would they even see themselves using this new vehicle? What would they use it for? That helped then to paint the picture of why the stadium was being built.

It became even more and more critical to do the behavioral side of things and figure out what matters to that person on the other side of the table. When we launched the campaign with the sales team, leading the charge, that’s how we went about it every single day. It’s not somebody showing up at this sales center and you’re walking them through a tour and hoping that they buy at the end. There are specific things and questions that you need to get answered at each stop that’s then going to make your time to dive deeper into the information in the closing room much more impactful.

I would say that I remember being involved at some level. I wasn’t involved with it every day in terms of strategy, even in that sales center. What dawned on me at that point, what I learned out of that project was how to create artificial momentum and how important that artificial momentum was. What I mean by that is, you got to be recognizing in every pitch where there’s a natural interest and where you got to create that momentum with a question and ask or an outcome at a certain spot. I don’t like the word scripted, but that flow was down.

Everybody on the staff, by the end of that project, they could probably recite to you almost verbatim what would happen at each stage of that center. The other thing that we had to learn there is how do you overcome perception. Every single day across the street. If you remember that gas station that was across the street from the sales center, there was a TV crew there every day.

You guys were getting brutalized in the marketplace with overpricing. There were things that got out and the press was attacking it, and those salespeople had to deal with the price objection before somebody walk in the door.

There’s a strategy behind that, and then there’s the marketing strategy that we put in place to dispel the rumors.

The whole thing was always a perception issue. You’re dealing with perception at all times. That’s tough for a salesperson. To anybody who’s reading, you’re only as good as the weakest link on your sales team, so it has to be built for the lowest common denominator, not the high performer. At the end of the day, because there are all these sales people. You’re in that position for and I wouldn’t say it’s a career-maker, but that’s a huge credibility to your resume right there.

I would say it differently. I think it is. The success that I’ve been able to have since then, none of that exists without that project.

Essentially, the Cowboys get into a partnership with the Yankees on a concept called Legends. You guys started creating this model, Legends Global Sales, which would duplicate essentially what you guys did in Dallas for anything that came out.

The Yankees-Cowboys came together from the Hospitality side. This launched as the food and beverage provider inside the AT&T and Yankee Stadium as well as the merchandising side. That’s how we started the conversation about the revenue generation from premium and ticketing was ongoing, but I was getting recruited at that point to go to Charlotte. I was faced with some real hard decisions. I loved living in Dallas. I truly loved the organization. Certainly, that vehicle or stadium was going to be a revenue generator for the future. The opportunities for jobs were still there. It was the desire to run your own show per se.

What role in Charlotte? What’s the title?

I was the VP of Sales and Service.

ASO 39 | Professional Growth
Professional Growth: It really became the pre-planning, and the focus you have to have to launch something was just different.

The whole shebang, everything you’ve been working for.

Everything that I felt was important to me and I wanted to have the responsibilities, it was being offered to me. I had the caveat of a little bit of insight during the recruitment process that the Jordan acquisition of the team or potential acquisition of the team was real. It became appealing. They hired a new CRO who had come from the Bills, a guy named Pete Guelli. Who’s now the Head of Commercial Operations for the Giants. I had a little bit of synergy with him because we had the NFL connection. I thought this would be a great working situation. I have all the responsibilities and Charlotte is not a bad town to live in.

You show in your career. You’re a very talent risk.

I am. I don’t know if it’s part of my makeup. I’ve always desired to experience different cities and different ways of living. Again, where I was young and maybe didn’t take my career seriously, it was all about working with great people and where’s the best opportunity.

You go into this. I want you to think specifically about this question. You have all this experience. This is your fifth opportunity. You’re going to do what’s different this time. You go into that one. You’re saying, “I got to do more of this.” What is it?

There were two things I wanted to accomplish there. I wanted to change the image of the brand. How do you do that from the ticket sales side of it? How do you become more of a community partner in this and that? This becomes the place where fun, excitement and value for your dollar happens, so that was one thing. The other thing that I wanted to do is I wanted to get the pricing right. I went deep into the analytical and research side of our pricing. I quickly identified that in 2009 and 2010, which were the times that I was there. The NBA champions were the Los Angeles Lakers.

There were certain seats in Charlotte that were more expensive than the center court seats for the Lakers at Staples. Again, that didn’t feel right to me and I felt like it was a hindrance in the marketplace. To me, it was, “How do we change the brand and how do we get pricing correct, so that the marketplace sees value in spending their money here?” Particularly if the North Carolina kid comes home and buys the team, as it turned out, he did. As it turned down, I failed on the pricing.

Was it too much?

This is important for everybody here. I was willing to lose and willing to fail. I stood on the table for some things that may be perceived as assertive and aggressive. I was recommending after nine months of doing diligence internally at all different departments, as well as the NBA involved in some of their analytical people. Right at the fact that we needed the lower pricing in a lot of areas, but the demands showed that in other areas, you could raise it.

I went as far as building out projections of how we sell more and make more money, as well as took a crack at the marketing plan of how do we message this the right way. I got told in those meetings that we will never be the organization that is in the paper that lowers pricing. It shocked me and made me realized, whether they were right, I was right or I was wrong, that you got to work with like-minded people. There was a little bit of a standoffishness there that I thought was misaligned that would never put us in the position to have success.

How long were you there?

Pride is not the greatest thing to recommend to people. I was there less than a year.

It’s all about the tactics and strategy and the things you do to be ready that put us in a position to succeed.

Is that a do-over for you?

No. It’s not a do-over. The timing that I wish we were a little bit longer, but no. I don’t regret making that decision. It was an unbelievable learning experience for me of truly vetting organizations from top to bottom and making sure that you’re aligned on a strategic approach, direction and goals.

Would you ask different questions in the interview process to figure it out? That was your controllable there.

Completely my controllable. I think back often on how we went about those nine months of this research project and arriving at this. Could I have done some things differently? Probably at the tail end of the presentation side of maybe setting it up better, so that way it may be as not as shocking in the room. In regards to going there and having the ability to work with Michael Jordan and his people on a day in and day out basis to understand what it means to be a $1 billion brand and how you need to operate, I wouldn’t change that for the world. I would do more diligence on the front end of making sure that there’s alignment for where we need to go to have success.

Back then, strategy became a theme and reading people at the moment became a theme. It’s a combo. You leapfrog out of there.

Ironically, I went there and within several months, Legends Global Sales, which was sales and marketing, when we originally launched, was not a thought anymore. It was gaining momentum and I had been asked to come back. I fought it for a while and then went through this process and realized, “Charlotte wouldn’t be a place ideally for me to have the success that I think should happen.” I made the decision to come back as Legends was launching from the sales and marketing side and that was done in 2010.

We launched in 2010, the sales and marketing side. We come out of the gates strong with San Francisco and then followed that up almost within six months for sure, with the Rose Bowl. We come out of the gates with two unbelievably important and one historic project. I had a great chance to get into the RFP process, and what does that mean and how do you respond and show depth but also tell a story.

I look back on your career that I was involved in because it became a piece of my business too, where Legends was offering training or including training as part of their solution. It was me and my company, primarily me. Understanding your job, you were pitching CRM services and training. You became my best number one salesperson. You weren’t working for me.

When I say that, a lot of business owners coming into the Tyson Group at the time was because Todd Fleming was bringing it to the table. It was that whole thing. I want to set the table for everybody. Todd has to put divine design to something because he was tasked with going to sell the service. That was his primary role, and you were employee number two.

Two or three on the Global Sales side.

Legends existed from the Food and Beverage standpoint, but you’re 2 or 3 and you’re tasked with selling the concept. Truly for everybody, I want you to understand something, Todd and I talked a lot about this mess. This is conceptual sales at its best. He is selling air. It’s a very expensive air.

I look back at it and again, I don’t know if it’s because it’s was one of the first things that we did at Legends. It’s still some of the most enjoyable times I’ve had at Legends. We sold a CRM system, where we had coupled with another partner and build out a platform that was inside Microsoft Dynamics, and then obviously the training. It was enjoyable because it gave me a chance to do business with my friends, but it showed me that the connectivity of what Legends is. We have something that can play a part in every single space inside the sports world. It didn’t matter.

You’re in the business world. We used to argue that all the time. The integration is all in the drivers on sales of the business. You could take that model and go into an insurance company and do the same thing.

We started this whole thing off like it was the entrepreneurial side of what I was doing was amazing. That drew me to the internet company and to Legends.

Anybody that’s reading this, especially because we have two audiences here. We have senior leaders, managers and directors that listen to this, but we also have an audience of salespeople looking to figure that out. If you’re trying to figure it out or you’re a younger manager and you’re worried about this ladder progression of it has to be one step, the next time must be higher, you’ve proven at some level at being a little bit of a risk-taker trust in yourself. You’ve made a few lateral moves that have catapulted you, and then you’ve changed your role.

Right now, you got to understand at the beginning of the startup of Legends Global Sales, Todd was not managing a team. Todd’s back to managing Todd and trying to execute with senior leadership and what he’s helped design the blueprint and sell it to people, to other senior leaders. You all need to realize if you looked at it on paper and you’re only going, “I’m not managing 15 to 20 people here, but I’m managing potential revenue of millions.” That’s where you’re looking at, correct?

Yes, 100%. For me, it was always this, I want to make sure that this comes across the right way because I do understand the titles matter but they never mattered to me. You can call me whatever you want. For me, it was all about, what are the responsibilities and what’s the pay? What’s my opportunity? Those were the things that matter to me. It was, “What are the responsibilities and do they match what my expectations are?” By the way, are you going to pay me for that? That’s what matters.

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When you talk about value, you’re going to compensate me in a way that shows you value me. You launch this and this thing grows. This is back to where you start centering to where you are right now. You get heavily involved and this is where we’re back to the top again because I can remember one of the big projects you sold was COTA, it was a racetrack in Austin. That’s what brought you there, but then you also got involved for many years in helping plan and consulted with AS Roma. This is now back to where you start to have your tentacles out there. You’re managing multiple products and hundreds of salespeople and leaders underneath your guide in multiple languages.

It happened chance because there were two people in the office when we got Americas’ job and one of them had multiple responsibilities for multiple organizations. To run that project, I was the only one that was available to go do it. It was originally going to be a one-year deal. I was going to maintain a little bit of my responsibilities of business development and trying to grow Legends and fly back and forth. When it became a two-year deal, it was like, that’s not going to work for my family and so we moved. It was great. If you think of Circuit of The Americas, it’s been a common theme in my career. It was, it didn’t exist and you have to make it exist and to make it stick.

Did you go back to the beginning? Todd has sales training in San Antonio. He says you have to come down and do it. We spent a lot of time in San Antonio. He brings the team to a Spurs game. We’re both exhausted. We’re sitting in a suite, we had a couple of drinks. We weren’t even liquored up and we’re sitting on this couch. Me on one end and him and the other, and we’re exhausted from the day. We both fall asleep and I look at him.

I go, “Do you think we should both go hit the hotel?” We were all staying at the same hotel. “Do you want to get an Uber and go hit the hotel?” He goes, “I’m exhausted.” We both realized that at the same time that we got old at the same time together. I shared that with him. We always have laughed about that because if you rerun that to 2 or 3 years forward, we would have been partying with players after the game.

We would have been trying. I remember that conversation thoroughly. Leading up to this training session, we meet on that day. We were talking a big game about having a few drinks and a cigar or two.

We had big plans that evening, but we look at each other and we were both tired.

Circuit of The Americas was great. We created something out of nothing with the partners, and it’s been fun to watch. If you go back, I said, “Those are four things I wanted to accomplish in my career.” I’d given up on the championship side of things because that’s out of your control, but something else started to pop into my mind. I’m married to a Colombian woman, and so the international landscape has always been exciting to me.

I started to chase international projects. I do think that if you look at international Europe and South America, they’re America back in the late-‘80s, early-‘90s before the boom of our stadium. To me, it’s like, “To go back to where my heritage is from and to go see where my wife’s family derives from and to have a chance to do all of that and do business, that sounded cool.”

We’ve got a few projects over there. We’ve opened a stadium in Madrid. I’ve had a chance to have my hand in all of that and take some of the strategies and the practices and evolve them to meet what it means to do business in Italy, specifically, Rome. What does it mean to do business in Madrid? It’s because it’s different than doing business in Milano and Barcelona.

Taking all the things that I know and the experiences all the way back from Atlanta, and then implementing those now across our global perspective, it’s been a fun and enjoyable journey. It’s still challenging at times. We don’t have all the answers and we still lose probably more than I want to, but it’s been a fun journey for me to be on.

I got a couple of speed questions after this. You’re in a unique position, where you’re involved in very complex sales processes for well into 7 to 8-figure sometimes in some of the products you’re involved with. Going forward with sales right now, what has changed, the adjustment and what’s exactly the same? There are a lot of people are talking and even me. We’re talking about this new business reality. Some people say, “Turn the switch back on. I don’t believe that. I think there are some hybrid things that are going on.” What’s your experience? What’s your opinion on that?

You and I talked about this even pre-pandemic. We were together when the world shut down. I tend to agree with you that COVID has changed the landscape. In the world of revenue generation, we’ve realized that managing by the results is ever more important. Again, activity is activity. I’ve always taken the managerial approach of, everybody’s style being different, and the way that they go from A to B may be different. We have to have an umbrella that everybody operates underneath, but you got to give people the freedom to make it work their own way.

During COVID, offices may not exist the way that they used to exist, and as sales personnel, you’ve got to manage by the results. The communication that we need to have as managers moving forward clearly outlines what the expectation is and how somebody is going to be evaluated against that expectation, and then get the hell out of the way and let them do their deal and manage by the results. I think that’s going to be the wave of the future.

I keep saying in a lot of training we do, what to find a win yesterday, you might not have to find a win today. Those results might be incremental steps to get a deal. A lot of little beachheads you’re grabbing.

The other thing is too and this may be more sports entertainment, live entertainment related. Those businesses were hurt financially hard.

Other than a restaurant in New York, the second-worst business to be in during the pandemic.

I would agree. A lot of times, Legends has a lot of sweat equity in the game but it’s now like, “Where do we deploy capital that accelerates a relationship and a project or allows us to become a much more of a substantial partner in your business?” That’s one thing that’s going to change. Moving forward, you may see more private equity money come into sports and see more agencies that are taking financial stakes. It’s going to be an interesting process to see where that goes financially.

Across the board too, even if you take it out of sports or entertainment. There’s a lot of partnering going on that way. The last three questions and this has been a great interview because I got insight from you that I didn’t realize before. I’ve often told you one of your greatest strengths is. I’m not a heart and flower guy. If you read this for the first time, for me to give hearts and flowers is, I’m one of these Clubhouse rooms giving people hugs is not my style.

It’s been fun watching you evolve and you have truly evolved and on purpose. It’s not like you all have to understand to get that result, sometimes whether it’s a strategy when you go to Dallas, whether it’s learning how to manage up in Miami or learning how to manage up differently with results. If evolution is the thing and evolves the right way, that’s how species survive or that’s how our own species survives right or the wrong person. I’m going to ask this one differently. Your funeral, that casket is up at the front of the room or coming in the funeral home. I know this is morbid, what song do you want playing?

Can I do two?

Yes. Talk about the audiences then if you had two. Is it the same audience?

Yes and no.

Is it the beginning and the end of it?

I try to fancy myself as like the melting pot. Different people, different views, different backgrounds and all that stuff, I try to be accepting open and have diverse of a network as possible.

You were going to a rap concert, the week after we had dinner and they were closing stuff down.

Ironically, the first song is going to come from that rap. I went to see Ice Cube after I left you, and it was around my birthday. To me, It Was A Good Day would be one, and then I fancy myself salsero, which means a male salsa dancer. That is because of my wife. Colombians are arguably the best salsa dancers in the world. That’s how I met my wife in the salsa merengue club. There’s a song called Oiga Mire Vea, which is about a woman from the town that she’s from in Cali, Colombia and it’s amazing. It’s by Guayacan Orquesta. Those would be the two that would be played at my funeral.

You have young kids now, they say, “Dad, what does success mean?” Do you say what?

It’s a great question. I’m literally in it. I’ve got a 21-year-old, 14 and 12. The 21-year-old is at the Ohio State University. He’ll be graduating next year from the Fisher School of Business. He’s got his head on straight, but I do this all the time. To me, success looks this way for the individual. It is, “Can I look myself in the mirror and say the following things? Am I happy with what I’m doing? Am I doing it with people that respect and care for me and I respect and care for them? Do I have an opportunity every single day to have success based upon the things that I’m great at?”

If you can put yourself in those positions, that to me is a success. I get all the things to trickle off of that financial, wealth, recognition, respect and all flow off of that. I say this to my kids all the time, “If you can answer those three things every single day in the mirror to yourself, then you’re in a good spot. Then you’ve had success.”

What book besides mine do you gift the most?

Shoe Dog by Phil Knight. I have said this to you. I don’t read a lot of business books. I read a lot of war generals and leaders of that perspective because if I could do it all over again, I’d be a history professor of the Roman empire. Shoe Dog gives you everything. It gives you sports, a tragedy, calculated risks, a brink of extinction. It gives you a true insight into what it takes to be an entrepreneur, a leader and a life-changing or world-changing company. The ebbs and flows of what Phil Knight went through with that company. Even as recently into modern history, like modern-day that how it’s all changed to me is fascinating. It’s how he was able to navigate it all. Outside of your two books, that’s what I give the most.

What a great interview. I was excited about doing this and I can’t wait to get this out. Thanks for being on. I appreciate you, Todd.

I appreciate you. I hope it was successful for everybody and good luck.

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About Todd Flemming

ASO 39 | Professional GrowthSales & Marketing professional specializing in revenue generation, marketing & business development.