How Great Sales Leaders Remove Obstacles, Not Just Close Deals With Colin Cook

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What does it take to lead sales for some of the biggest stadiums, sports franchises, and entertainment venues in the world?

In this episode of Against the Sales Odds, Lance Tyson sits down with Colin Cook, Executive Vice President of Sales at Legends Global, to explore the leadership principles that have shaped his journey—from serving as an Army officer to leading a global sales organization of more than 350 professionals.

Colin shares the story behind Legends’ work on iconic venues like SoFi Stadium, Mercedes-Benz Stadium, Allegiant Stadium, and the new Buffalo Bills stadium, while offering practical lessons on consultative selling, building resilient teams, and leading through disruption.

Together, they discuss:

  • Colin’s unconventional path from the military to sports sales
  • How Legends creates world-class fan and client experiences
  • Leading major stadium projects through the uncertainty of COVID-19
  • Why transparency, empathy, and adaptability are essential leadership skills
  • How buyer expectations are changing across generations
  • The mindset every young sales professional should develop to succeed

Whether you’re leading a sales team, managing change, or looking to elevate your leadership game, this conversation is packed with real-world insights from one of the most respected leaders in sports business.

🎙️ Listen now and discover why the best leaders focus on removing obstacles—not creating them.

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How Great Sales Leaders Remove Obstacles, Not Just Close Deals With Colin Cook

Introduction: The Business Of Monetizing Revenue

I’m so excited about this episode of the show because I feel like this individual I have been on a journey with from Tampa to now, where he is now, Colin Cook, who’s the EVP of sales for Legends Global. Colin, I’m so excited to have you on. You and I riff so much. This is going to be like one of our coffee talks that we have anyway. It’s been a long time coming to get you on this. I’m excited. Colin, give the audience a one-two for the audience that does not know who Legends Global is, and then talk about your role and your responsibilities at Legends.

Now, thanks for having me on, Lance. I’m really excited to do this as well. Obviously, we go back a long time. Legends Global, ultimately, if you think about what we are as a company, is we are a provider of revenue services and support for some of the world’s largest sports franchises, leagues, rights holders, and all different types of live entertainment venues. If you boil it all down, ultimately we are in the business of monetizing areas of congregation. Whether it is selling naming rights for a new NFL stadium, programming the F&B in an existing venue, booking concerts, driving nightly revenue, or selling a private event within a venue, we work across the spectrum to help our partners monetize areas where people are coming together and doing things live.

I love it. Give the audience a couple of ideas of some of the projects Legends has going on right now, past, present, or future, whatever you feel comfortable talking about.

We work across the spectrum of live sports and live entertainment at this point in time. We’ve worked on the majority of the new NFL venues that have happened in North America. That was always the core of our business. Selling personal seat licenses, long-term suite leases, and sponsorship to some of these major sports stadiums like AT&T Stadium, Mercedes-Benz Stadium, Allegiant Stadium, SoFi Stadium, and most recently the Buffalo Bills’ new Highmark Stadium.

We branched out from there and built out more of a holistic food and beverage business and merchandise business. Now we’re doing everything from selling for the Las Vegas A’s and their move into Las Vegas, all the way to a number of international projects that I’m sure we will get into with partners like Chelsea Football Club, Athletic Club, and across the spectrum.

With the acquisition of a company called ASM Global two years ago, we then got into the live entertainment and venue operations business. We’re also operating venues around the world. That could be everything from a rodeo venue, Cowtown Coliseum down in Fort Worth, Texas, through to AO Arena in Manchester, Avicii Arena, and about five NFL stadiums at this point. Across the spectrum, changes are different every now.

No doubt. That’s a wide portfolio too. Take whatever you like. Whatever you like. Legends is working on it. Talk about your role. What’s your role in this grand scheme? Legends is a really big company at this point, and where do you fit?

I’ve been fortunate to be here for seven years, and it’s been a really interesting journey because there have been multiple iterations of what this company is and what we’re oriented towards and then how we’re growing at the current point in time. I sit as EVP of sales, and I sit over three core businesses. The NFL sales business, so focused on design optimization, sales campaigns, building sales teams, going to market, and delivering the revenue for PSLs and suites within the NFL.

I also sit over our international sales business, so effectively taking the business model and bringing it into Europe and some other international markets in Asia and Asia Pacific and a little bit in the Middle East, and thinking about how we can use North American monetization strategies, but do it in a highly local context within European football. Also our private events business, which is actually super interesting.

We operate over 450 venues around the world, and just within North America, we’ve got a couple hundred that have the ability to sell private events. That’s really the outside of the box, like selling an NFL stadium for a total takeover by a Fortune 500 company all the way through to a chamber breakfast or a fantasy football draft. How do we really think about these assets and monetizing them when the lights are not on for an event?

As much as I know about Legends, I feel like I’m going to learn a lesson. What’s that? Seven years. If you had asked me getting on here, “How long has Colin been over Legends?” I wouldn’t say seven years. It seems like only yesterday. Talk about the headcount and what reports up into you, that structure underneath you.

I’ve got a globally distributed team, obviously, especially with international business. I’ve got a head of the Iberia market, Diego Grau, who’s unbelievable and has led our Barcelona project and then come on to the corporate team. I’ve got a team in the UK of Vicky Jaycock and Oliver Wright that really support our UK properties and our growth. I’ve got an NFL business where all the NFL teams are rolling up. Each of those has a head of projects. When you actually start to add it up across that, and then you add in Christina Morgan, who leads our private event sales business, there are about 350 salespeople and sales managers that roll up through that group under the three divisions.

It’s interesting. Many people tuning in do not realize what goes into sports. I only think about trades and what happens on the field.

I was one of them.

We’re going to get into it. I get more interested in the business side. I get so tired of watching it because we’re so integrated into the whole thing. Colin, I ask a lot of the guests, how the hell did you get here? How do you land at the top of a global sales organization, and where did you start, where did you come from?

From Service Academy To Sports Sales

It’s definitely a different story than you hear from a lot of individuals, but I grew up in Halifax, Nova Scotia. I’m from the East Coast of Canada, grew up a hockey player, as one would expect. A really exciting time in Nova Scotia hockey. There were a lot of really good players, and we outkicked our coverage in the number of guys that we put in the league. I actually left home at sixteen, came down to the States, and went to boarding school, played the boarding school hockey thing. I ultimately went back to Canada to play my junior hockey career, played that all the way out until I was 21 years old. I couldn’t play in the NCAA because the eligibility things at the time were very different than they are today for what’s considered professional.

You wish you were playing now.

They’re a little different. Ultimately, I was headed back to Canada to play, and you can play university hockey, college hockey in Canada after having played pro. A lot of guys go back there, 21, 22, 23, and then go do their degree at that point in time. I was talking to a number of programs across the country and especially in Ontario at the time. I went to visit one of them. While I was there, it was actually in the same town as the Royal Military College of Canada, which is a Division I program in Canada. It’s effectively our National Service Academy because we have the Canadian Forces. It’s Army, Navy, and Air Force all in one institution, but effectively it’s Canada’s West Point.

There was just something about it. It just pulled me in. I said, “I’ve always done school and hockey. Why not just add this whole other element and dive into this and try it out?” I had no real service history in my family in the immediate term, but there was just something about the brotherhood of it and pushing yourself to the limit and learning this skill set and basically getting to go to leadership school and get paid to do it, and play hockey sounded like a pretty good setup.

Where would you have ended up if you stayed in the military? What branch of the Canadian military?

Actually, you have to pick one when you go to Canada. I went in as an army officer cadet. I was an infantry officer and tied into that piece, and then actually pivoted and went into some of the intelligence world and that side of it. It’s a little different than West Point, where we would play our season, and then you would actually get shipped off to training somewhere across the country, and you would spend an 18-to-20-week training block. Most of our graduates, when they are actually commissioned as a second lieutenant, are coming out as fully trade-qualified officers. It’s a little different than the US, where you get your MOS assignment when you graduate. We would get them early. We were going through all of those progressions. I commissioned as an Army officer.

Were you just in during your time while you were in school, or did you have additional? What does that look like?

I did. I did about just under seven years total, counting some of the school time, and then stayed afterwards for a few years in a number of different roles that were pretty interesting. It was the greatest experience I could ever imagine. I highly encourage people to look for places where you can go, whether it’s the military or somewhere else, where you could be a part of building something, learning leadership early. Having that service-oriented element early in your career is just really important.

Look for places where you can go and be a part of building something. Having that service-oriented element early in your career is just really important.

When you walk out of that after seven years, and obviously at that point you’re thinking of a career, “What am I going to do?” At that point in your head, you were equipped to do what? What were you thinking?

It was interesting because I did not really know. We have a great network of ex-cadets that have gone on and done their military time, and they’ve got out and worked in industry. I connected with one gentleman who has a finance background and did investment banking, a little bit of private equity stuff, and was in New York. He recommended, he said, “You could really take a path down a finance track. It’s analytical, you automatically are polished coming out of the military, you know how to present,” because as an officer, basically your job is to tell the story and convince other people that they need to believe it. Effectively, you’re selling as an army officer every day. He was like, “I think finance is a good path.” I actually took a job in finance, and I moved to Chicago.

I did not know that.

Now I’m finding some new stuff. I took a job, moved to Chicago, and said, “Maybe I’m going to go down this finance path and be a portfolio manager, find where that’s going to go.” I was there for about six months. I knew it wasn’t for me, not because of the company I was with, but it was a little bit of, there are some crazy statistics. It’s like 90% of veterans who come out of the military leave their first job within eighteen months because there’s a big changeover.

I was a team athlete, and then I papered over the end of that by staying in the Army. When that ended, it was like I was looking for this sense of mission, teamwork, seasons, and living within that cadence. I found myself sitting at a desk and said, “This actually probably isn’t for me.” At this point, I’m 28 years old, and I have no real civilian experience. I quit this job, and I call my dad, and I tell him, and he’s like, “You really need to figure out what’s next.”

You’re at the tail end. You’re 28 years old, right? What are you going to do?

As it happened, a guy who was from my hometown of Halifax, Matt Hill, was at the Tampa Bay Lightning, leading their suite sales program. I called Matt, and I said, “Is there any way I can come down and coach to learn to play for six months or something as I figure out what I need to do?” Matt said, “Sure, but no, actually, I think you need to find a way into ticket sales.” Lance, I honestly thought he meant working in the box office, tearing the ticket stubs coming through the door.

It goes back to what we said earlier. I had no idea of the engine that goes behind what our business is. At 28, I took the leap, moved down to Tampa, and took an inside sales job. It was everybody who studied sports management and came right from school into this job. You’ve got this guy who’s older and coming out of the Army.

I was just going to say that, too. Sports early on does not pay a ton. It’s one of those sales jobs that’s starting at a hundred. You’re probably starting at 25 to 30 plus commissions, and you’re dealing in the entry levels of inside sales. Colin’s 28 years old. He’s going up against 22-year-olds. How did that work for you?

It was actually great because I took the position very early on that I knew I had this relatively unique leadership experience, as anyone who goes to a service academy and you graduate a platoon commander at 22 or 23 years old, and you’ve got people that you’re now legally in charge of that have been in the Army longer than you’ve been alive. You end up having that leadership experience. I knew I had that.

I just took the perspective of “I’m going to learn everything I can about how this business works, because if I can connect my business acumen with my background as an athlete and leadership experience from the Army, then that would be something that could probably propel me.” I just took a long view of it and, being completely transparent, unbelievable organization I worked for. Steve Griggs, Jared Dale, Ryan Cook, everybody I worked with, it was just such an awesome time.

It was a great organization.

The “Lightbulb Moment” In B2B Sports Sales

I could not have started at a better place. I still keep in touch with so many of those guys. It was just one of those situations where I’m a Canadian kid from Halifax that’s living in Florida, working for an NHL team. I did not really care about the money because I had that sense of “We have a season, we have a mission, we have a goal, we’re chasing something as a unit.” That just made it really fun.

You made that connection. As you’re in your first sales job, and you have a lot of salespeople working for you. You and I have talked a lot about sales. What’s a young Colin in sales? I have heard everything. I’ve heard, “I was at the top of the board.” I’ve heard one of your fearless leaders, Chad, say he was a solid 5, 6, or 7 on the board. Where’s Colin at that point?

It was funny. When I first started out, the first six months, I was like, “This is not it.” I’m calling somebody that came to one game last year and saying, “I hope you had fun. Do you want to come to 41 next year?” It was hard for me in the B2C context. It was easy to call and talk to people and have conversations, but it was quite difficult for me early on to have that asking-for-money conversation with an individual, especially if someone did not have some existing deep affinity. It all switched when we started getting into B2B sales.

The light bulb went off for me. “They’re going to use this money somewhere. They’re going to go do a steak dinner. They’re going to do a rewards trip. They’re going to go take this marketing money and go do something with it. I’m passionate about what they can do, aligning with us and entertaining via hockey. I’m not asking for that individual’s money. I’m asking for money that I know is going to get spent somewhere else. Now it’s consultative.

Now we can sit down and have a conversation about what they’re trying to achieve and everything.” That was the light bulb moment for me. “Wait, we’re just having a conversation and trying to figure out a mutual fit.” Then I fell in love with it because everything in your pipeline becomes a little puzzle, and it becomes a little problem that you have to solve and figure out.

Sales Obstacles: Everything in your pipeline becomes a little puzzle. It’s a little problem that you have to solve and figure out.

 

That makes total sense. That’s really well said, too, because the value proposition made sense in your head because it’s something you would have done. I love that. You’re in sales, and Tampa had a smaller inside team, so you got a chance to spread your wings and things like that. Talk about your success and some of your trajectory in Tampa there.

I did about a year and a change on the inside sales team. I was not top of the board. Similar to Chad, who’s a mentor of mine, I was a 5, 6 guy in inside sales, but then I moved on to the corporate sales team. We had a really strong group of guys, and that was mostly selling premium, a little bit of some university sponsorship stuff we were involved with, but mostly the suites and premium clubs. At a really advantageous point as a business, we were reaching capacity. We were really being able to get creative with some of the premium stuff we were offering.

I spent a couple of years on that team, about eighteen months actually. I did finish first on the board once in that team forever. The guy that finished second, I text him once a year and remind him. The irony is that from top to bottom on our team of seven people, we had all sold over a million dollars in inventory, and from top to bottom, I think the gap was $106,000 or something from first to seventh. It’s almost a funny joke. We still have a group that we talk about. We had probably one of the greatest teams ever put together in that scenario because we all had a lot of success as a team and were hyper-competitive about it.

I was going to say we’re not competitive, are we?

Not at all.

I think about our early interactions when we were doing some coaching down there. Colin, I’ve told the story a couple of times. I would always work with emerging leaders and the leadership team, and I would get scheduled out. I’d have breakfast and lunch and dinners for 2 or 3 days in Tampa. It was great. I was eating a lot, but my schedule was packed. One evening, Colin and I had dinner, and I had forgotten a belt. I forgot a belt. When you travel as much as I did, Colin was so astute because he heard me whining about it at some point.

He brought me to Brooks Brothers, got me a belt, and then we had dinner. That’s when our connection happened over a belt. You never know. To that point, it’s not who you know, it’s who wants to know you. I always look at you as a master networker, a master at network analysis and making those connections and things like that. At that point, you’re starting to get close to your late, really late twenties, and you start to say, “What’s my next move?” Where do you go from there?

I was on the corporate sales team, and I was giving a really hard, strong look at leaving sports and going back and doing a full-time MBA program. I studied political science as an undergraduate. I felt like I had a little bit of a gap. Now that I was in business and I really liked sales, I felt like I had a little bit of a gap in hard business skills. I had some friends that had gone down that path. I was really strongly thinking about that. As fate lined up, an opening happened to be an inside sales manager within the Tampa Bay Lightning.

I had been there about two and a half years and had this chance to move into a management role. At that point, I was like, “If I do go back to school full time, I’m just going to be coming back to get my old job.” To this day, that’s one of the favorite jobs I’ve ever had because you’re basically a coach, and you’re going from, “How do I buy a car? I do not know how to sign my lease. Can you help me?” with young people coming in to actually shape them, and seeing where they are today is pretty cool. I had this moment of, “The business acumen and the background leadership stuff that I’m really passionate about, if I wasn’t doing this, I’d be a hockey coach.”

That came together for me. I did that and then ultimately moved into a senior manager role in a ticket sales group under Travis Pelleymounter. At that point, we had reached a sellout capacity with the Lightning. We’d had a lot of deep playoff runs, hadn’t yet won the first cup, but we were at a point where the business had changed. We had drawn down a lot of the new business team, built up more of a service team, and it had nothing to do with the organization whatsoever. It was a little bit. I had this itch to go do something that was asymmetrical, go do something that did not have a clear probability. It wasn’t a hundred percent probability of success.

Sales Obstacles: Truth: Never shirk away from telling the truth even if it’s to your superior and even if it’s not going to make them happy. And never lie to your troops because you will never get that back.

 

I had gotten interested in the agency world. At the time, the Allegiant Stadium project was happening. Mercedes-Benz and Levi’s Stadium had concluded. Legends was this up-and-coming organization within the sports industry. There was something about it for me that really appealed because you have to go from A to B and it’s very linear. A sales cycle for a team is very cyclical. You’re going to do things at the same time every year and hope to find some incremental gain and adjust your approach. Ultimately, there’s a cyclicality to it. What Legends does and what agencies do is linear.

You’re going to start here and go from A to B, and B is when the stadium opens, and there is no. You do not get time back. If something breaks, if something’s going sideways, if something is going on, then ultimately you just have to pivot and go around it because every day is a day closer to the stadium opening. You do not get extra time. You cannot try again next year. There was something about that that really appealed. When you boil it down, it was “You’re here, and you need to get here. Here are your resources.

Here are the things you need to be mindful of. Go get it done.” To me, that’s a mission in the Army. That’s exactly how we get a mission brief. It’s no different than “Go execute against this objective, and you have X amount of troops and X amount of time, and go figure it out.” It was a thought process that appealed to me. I also liked the idea of building a team from the ground up and getting to shape a lot of that.

Let me go back to one thing. I’ve counted how many times I’m a pattern guy. You talk about missions, and you talk about seasons, like a certain phase and something as you start to look, but also move up in management. Talk about what you realize about your leadership at that point. Before you turn the page to the next step, what did you use from your military? What were some other things that at that point you realized that maybe you did not think about before?

Leadership Philosophies: Truth, Duty, And Valor

One of the best pieces of advice I got was when I was actually still at the college, and there was this gentleman that had been a colonel in Afghanistan for us, and I was having coffee with him and said, “I am going to be a young guy coming out as a platoon commander in the military. What should I be thinking of?” He said, “It’s all wrapped up in the college’s motto. Our motto is Truth, Duty, Valor.” He said, “Truth, never jerk away from telling the truth, even if it’s to your superior and even if it’s not going to make them happy, and never lie to your troops because you will never get that back.”

Duty was the second one. He said, “Duty is very easy. When it’s fun, be at the back, and when it sucks, be right at the front.” Valor, which you would think you know what that is in the military, but he said, “It has nothing to do with bravery in the traditional sense, but it’s having the moral courage to do what’s right and to hold to that.” That was my framing of how I thought about leadership experience. I am very close with my father and someone that I look up to incredibly. We had this acronym called HIRE that we had used my entire life growing up.

Valor has nothing to do with bravery in the traditional sense, but it’s having the moral courage to do what’s right.

It stands for Humility, Initiative, Responsibility, and Enthusiasm. The whole basis of that was every time you approach some challenge in life, some job, some role, approach it with those four constraints. Blending those two together was my baseline of how I thought about how I wanted to show up for my people, have that “it’s not about me” mentality. It’s about how do I use these to show up for them? That part, I do not want to say I had to figure it out. I certainly did not. I had a ton to learn when it came to it, but I had a framework for that.

What I did not have a framework for and really had to learn was how to manage up, how to think about communication, how to make sure that you’re getting all the stakeholders on board, because ultimately it’s a very matrixed business, especially in ticket sales at that point in time. It was really important to figure out that network and influence network internally, and how do you manage up and how do you keep multiple projects going at the same time?

I really worked a lot on that phase of my career, setting the intent like this is where we need to get to, and then allowing for that diffused responsibility of letting the team figure out a path to get there and not being overly micromanaging or dictatorial. I found that helped a lot with managing those matrix environments when you can sit down with marketing and the community foundation and analytics and say, “Look, here’s the end goal. We need a renewal and retention model. I am not going to say it needs to have A, B, and C, but it needs to do this. Now go build that.”

That’s where a lot of sales leaders often fall down, as they get overly prescriptive with some of those internal groups where ultimately we’re a customer of these really highly talented internal teams. Just give them a brief of what you need them to build for you and come back. That was a learning curve for me because early on I would say, “I want this, and it should look like that.” I had to step back and say, “Actually, I cannot be prescriptive. You have got to let the experts go be the experts.”

Well said. From there, you interview, and you get a golden opportunity to get involved in the agency world, right? You get a shot at Legends where you are now. Can you talk about that? It’s interesting because you have a unique perspective, and a unique experience is probably even more interesting.

Adapting To The Pandemic: The Columbus Crew Project

It was a really interesting project. It was the Columbus Crew’s new stadium project owned by the Haslam Sports Group. The Haslam Sports Group had purchased the team, had a new stadium project approved, and needed help and support. How do we get there and figure it out? It was funny because people gave me the, “You work for a hockey team in Florida. Why would you go work for an MLS team in the middle of Ohio?” That doesn’t seem to make sense on paper. It was the challenge aspect of it. It was like, this might not succeed.

The Columbus Crew at the time had almost left the market, and there had been this big Save the Crew campaign. It’s actually the first soccer-specific stadium that was built in North America was the venue they were currently playing in. It was quite old and quite dated. It did not have any premium. There was like this real opportunity to take a club and transition them from something very straight, historical into a totally new era.

It jumped forward about 25 years. I knew it also wasn’t, like I said earlier, guaranteed success. It was a chance to come in and start fresh. It was a chance to learn from a lot of really good people that had also been brought in for the project and the leadership team at Legends. I just said, “I am going to dive in with really no grand master plan.”

People said to me, they were like, “You’re going to go to an agency and do a project and then after that project, you’re just going to be looking for another job. Isn’t that how it works?” I was like, “Maybe it is. We will find out.” I knew I wanted to go and do the project, and I just had a feeling that saying yes to that and taking on an opportunity that maybe wasn’t as glamorous on the outside and from a brand perspective. It often gives you more opportunity to learn and grow.

As we have this conversation right now, it’s the World Cup. Soccer’s gaining popularity. You rewind 6 years ago, 7 years ago, it’s still the sixth league in a four-league country.

I have a lot of customers in MLS.

Now, something interesting happens in the marketplace. Here you are building a new stadium, you’re in a people business, and we get hit with what?

The COVID pandemic. We were on the ground. I want to say we got there like October of 2019. We’re building the sales center, and we’re recruiting a team. We had about 30 people all in, 25, 30 people recruiting this team. People are moving there. We’re building the sales center. We’re getting all excited. Talk about asymmetrical. Sometimes, like the sales center wasn’t ready. We didn’t have an office. We did the first month of training in a WeWork in Columbus. We just rented the bathroom, so you just have to adjust and figure it out.

Sales Obstacles: A lot of sales leaders fall down because they get overly prescriptive. We’re ultimately a customer of our internal teams, so just give them a brief of what you need them to build for you and come back.

 

We did the WeWork thing, and we had this big excitement. We’re all going to move into the office, and we’re going to have the sales center. We’re going to get going. We were there three days before Tom Hanks and Rudy Gobert got COVID, and they shut it down and said, “Everyone grab your computers, and you’re going home.” We were sitting here like, “We were going to go on sale in a month.” Now we do not know if sports are ever coming back. How are we going to figure out how to go take a new stadium?

Especially in a marketplace like that, where we knew we would have to grow the database substantially. We knew we would have to go find a lot of new B2B and high-net-worth buyers and young professionals that were going to want to buy stuff. We knew we had to go do all of this hunting, and now we couldn’t do it in person in a sales center as Legends typically does. It was this really unique challenge. We basically stepped back. We had about a six-month delay in getting on sale.

We said, “How do we put this whole thing together and build the whole system such that we can go do Zoom meetings and drive all of this interest through the top of the funnel and all the pieces?” Ultimately, we ended up doing 8,476 Zoom meetings to sell out that stadium. I will never forget it. It was unbelievable. Give that number again. That’s unbelievable. 8,476 Zoom meetings, to be exact. It was the course of about eleven months. By the time we got on sale to when the stadium opened, it was eleven months.

If you listen to this, you get it. The stadium has experience like you trying to sell it at that point via Zoom and not be able to experience an experience center, and you got a fragmented sales process that’s causing even more delay. At that point, if my memory serves me correctly, you guys were deep in the Islanders building their new stadium. The Clippers had just kicked off, the start of Just starting to. There were three projects that were like one Midwest, one East Coast.

We had SoFi still wrapping up as well.

You were up at SoFi.

That’s exactly right.

You guys were wrapping up. It was a fight. It was not easy. Introducing something like a small bit of those other projects. They had Against Columbus is the big cities. Columbus is totally awesome.

Established brands, big four leagues.

Now, is it safe to say, Colin, that like, when you think of supply chain and things that you worked on in the military, how did that come into play with this? The coordination that you worked on? I always thought that would have been really good training for you there, that whole looking at things, right?

It was. The biggest thing that I took away from that background was stepping back and planning time to plan. One of the big things you learn in the military by force is that you, as the leader, need to have solitary time. You cannot always be with your men and with your men and women doing things. You have to have the solitary time to step back and think about how you might approach this problem, because as an Army officer, you’re the ultimate risk mitigator. People, I think, get a bit of a perspective, and I am very passionate about veterans coming into our industry and business in general.

There’s a sentiment sometimes that is like, “It’s the military, there are A and B and C and policy and all of these things.” When you actually peel it back, that exists to create discipline and a way of thinking, but there’s no more asymmetrical environment in the world than combat. What you actually have is a lot of people that were trained to think about risk mitigation, and think about how to get from A to B, accomplish the mission without causing your team to be in trouble or any of those things.

That aspect of it, the sit back and plan. I would sit there and write an op order, write a mission plan, and say, “If we need to go get 60,000 leads, here are the people that are going to be involved and here’s the order in which we’re going to do it.” It was a really good way of structuring your thinking on how to solve problems. That’s why a lot of military people actually do really well in consulting, because that’s baked into us early.

What did you realize about selling at that point? What changed? What was the thing you had to do more about, like when you’re thinking about methodology and sales process or even just the tactics, what did you start to form? You now are out of selling. You’re backroom now, your backroom strategy.

It was. I took a real approach at that point in time to step back and think about it. Legends does this exceptionally well. There are many groups that do it. What I learned coming into the business was very much about frameworks and value propositions. There’s never a script. We’re never sitting there saying, “Say A, then B, then C.” We run a read-and-react offense that we’ve worked on with Lance for many years.

It became even more important in that scenario, especially in COVID, a high degree of empathy, really meet the customers where they are, and really do the listen-to-understand piece so that we can sell into some gaps. It’s a little bit easier when you have the sales center. It’s not easy. That’s probably the wrong word, but it’s easier because you can stand there and say, “This is the seat, sit in it, try it out, and here’s this big fancy 3D model and like all these things that we have, these toys we have.”

Sales Obstacles: It became even more important to have a high degree of empathy, really meet the customers where they are, and really do the ‘listen to understand’ piece so that we can sell into some gaps.

 

Oftentimes within our sales centers, reps end up presenting more than they’re actually pitching and selling. When we stripped all of that away, really the core focus for the sales team became, “Now we really need to sell. We really need to understand how to analyze in a really deep way, because you’re going to get one shot and it’s going to be 35 minutes and the person’s at home probably in their pajamas doing something else at the same time.” It was a very different environment to be in. We really had to focus on the engagement, the question asking, and figuring out that empathetic, “What are we selling into?”

When you get your shot to perform, you’re really aiming some of this in small like, “Here’s what you have to do. Here’s the KPI at this point of the sales process. Here’s the KPI. Here’s your objective,” whatever you want to call it. Key performance indicator. You have to do really well there.

We really had to say we baked it out like those KPIs were all the way down. This is something we’ve carried across all of our subsequent projects, but like being really diligent in the number of touches per lead, scoring people based on their past purchase history to understand which bucket they might fall in. Even though you might say these are suite clients or these are premium sales clients, we’ve actually got different channel approaches within each of these products, and we’re coming at them with different value propositions.

Sometimes they flip between different customer journeys, and that’s all expected. It was very much about understanding, “What am I walking into?” The other thing we talked about a lot was “Walk, do not run,” like “Smooth is fast,” right? “Slow, smooth, and smooth is fast.” That attitude was really important because they weren’t coming onto the lot to be sold. We didn’t have them in front of us. We didn’t have physical control of their time. We had to be that much better at the conversations.

From a leadership perspective, you talked about leading the matrix or looking at it, and then you also mentioned earlier about managing up. Now, what’s interesting about the agency world or even the world you’re in, you’re like an embassy. You’re an embassy in the UK, like the American embassy in the UK. It’s probably bugged. Our embassy’s bugged. They’re even friendly. You have to serve the client nation. You’ve got to serve your team. You’ve got to take care. You’re managing up to the client and to the senior management, and then you have your team down here. You get like this three-way triage of information. What did you learn about that, and how did you manage that? You definitely embedded.

Mastering Stakeholder Management And Embassy Relations

After the Columbus project, I moved on to our corporate team. I was working on how we scale a lot of what we just talked about across different properties and collegiate and pro and all of those different places. That was a really interesting role for me because I got to spend a lot of time on the road sitting with our customers and our partners, helping diagnose a little bit of like, “Okay, what do you want from this partnership and how should this work?” The biggest thing I took away from that year and a half in that role was really to sit down and ask the question, “How do you want to receive information? What works best for you? Should we have a quick conversation once a week that you and I are talking about? Do you want a polished report on a Friday?”

That’s a real little sign.

How do you receive information?

That’s what people miss in the manager job because it’s supposed to be dictated to them. I work with a lot of sponsorship, partnership marketing teams. I’m like, you should be asking how they want to be managed and led as opposed to the other way around, and you fit around that because that personalizes everything, and personalization turns into customization. People start to have higher value.

There’s the internal and down to your team of, “How do you want to be coached? Do you like direct feedback?” and that’s right, or “Do you need to have your tires pumped?” The effort was how you take that and how you bring it to the client?

It’s almost the same thing, though.

Yes. What do you need from us? Oftentimes we’re dealing with the executive leaders at these companies. I was fortunately heavily involved with the Buffalo Bills. Phenomenal, cool project, great executive team we’ve worked with. Oftentimes it’s helping them, “What do you need from us to help manage your other stakeholders, be it politicians in the community, your ownership, your ownership groups, investors, all of those pieces. How can we come in and be a partner with you to help you do that?” A lot of people do not ask the question to your point.

Most of the time they’re going to come back and say, “What do you think works best?” It becomes their idea, not your idea. It doesn’t have to be your idea. You spend time on the corporate side, and then you get another big project.

I did. I was passionate about the NFL space, and we’ve been chasing a few projects. The one that actually came to fruition at this point in time, coming out of COVID, was the Buffalo Bills’ new stadium up in Buffalo. Obviously, close to the Canadian border for me. My family actually lived in Western New York at the time. My parents had moved down. It was just a really unique opportunity for me to come into a brand that I really saw ascendant with Josh Allen and everything that was going on and a really, really special fan base.

When you think of Bills Mafia, it is, I’ve said to many people, it is more like a Premier League football club than it actually is an NFL team, because you can meet someone that’s never been to Buffalo and is a Bills fan because their great-grandfather was from Buffalo. There’s a lineage to it that I think is really impactful. There’s actually more Bills fans outside of Buffalo Niagara than the total population of the Buffalo Niagara region. We were on it. It was crazy. It’s in this place where we got to take a super historic franchise fan base from a building that is quite old, it’s a 55-year-old building-ish at the time, and bring them into the future.

There’s always the obvious question of, “PSLs are coming. That’s going to be a net negative, and do you think you can go and get the sweet term and the total COI that you would expect to sell? In this marketplace, I do not think it’s possible.” I just had a bit of a chip on my shoulder that Buffalo really wanted to outkick what everybody thought and prove themselves.

If you get the building design right, if you’re authentic to the fan, you think about user experience and journey, the best part that came out of that project was we were from day one in the concept design meeting with the architects and the Bills leadership team, all the other constituents around the table. It will be a very special building when it opens in August, because it is one of the buildings that function the best when they feel the place that they’re in. It might be one of the most of-the-place buildings that I’ve seen be built in the NFL.

What’s really unique about as I’m thinking of your career, and I’ve talked to a lot of people and I do not think there’s a pure pathway. I think it’s everybody’s own unique pathway. Your career really goes to like four cornerstones: it’s military, it’s Tampa, it’s Legends. You enhance your responsibility internally, or your credibility internally, by getting it, getting one job done, and that came through that Columbus project. You capitalized on some things internally and then another, another project that you helped lead. You would say this.

It takes a team to lead one of those projects, and there are a lot of moving parts. It’s massive. Sales and the integration. The way I look at this is like each one of these moves are seasons in there, and there’s a mission. Each one’s very mission-led. Talk about that in terms of, because the Buffalo project for you was another end cap that allowed you more responsibility internally. Maybe talk about how your leadership, your executive leadership evolved there, how that allowed you to start. Now your responsibilities grew immensely.

It did. As you said, we were fortunate in Buffalo. We had almost 60 people on the ground there. It was the best leadership team I’ve ever assembled. We were very intentional about building the ghost roster of who we need on the team and hiring people around you who are really good at the things you’re really bad at. We had an exceptionally well-built team there, which allowed me the opportunity to continue to grow my own career, as you mentioned, but ultimately, it really comes down to that project was a capstone, to use your words, of putting all of the pieces together.

Hire people around you that are really good at the things you’re really bad at.

We went into that as an organization very early on saying, “We need this to be the one that develops all the talent in the process and all of these elements,” because it was actually the first NFL stadium post-COVID that had opened. There was this bullwhip of 6 or 7 years where you had all these young individuals that never got a chance to work on an NFL stadium. Go get that right. It was building that framework and understanding how to. That was the first time I was really put in the position of client, not relationship ownership, managed back up to our executive team, playing the ambassador role to extend your embassy.

That helped me frame up where I wanted to go. As conversations are happening like, “What’s next?” I just have this bent. I do not know if it’s in my personality or what it is, but I like those things that are a little bit in the gray, or they’re a little bit like, “How are we going to figure this out? What does this look like?” I’ve developed a little bit of a track of, “Here’s a sticky problem,” or “Here’s something that’s unique and a little bit different,” and come in and bring fresh eyes and go get it.

I was going to say that I think, as I listen to your story, I know a little bit about your story, and then it takes all types. Some people go for the very defined next steps, “Here’s my responsibility.” To me, you’re always more of a problem solver, and you grab a problem or an opportunity and do not worry about the comp. Do not worry about the title. For me, the title, the comp always follows. They do not have to lead. Solid done. That’s you in a nutshell. Look at you now, right? From Legends from a property all the way to leading a global division of all the properties and acquisitions.

If you had to sum up your look for the audience, if you decide, I am breaking down two things. You will have an interesting perspective, but maybe if you had an analogy, it would be cool too. If you look at your business development, your sales philosophy, just take your leadership hat off for a sec and just say, “You’re looking at the operating environment is different. It’s fast-paced.” Nobody can tell if it’s good or bad. What’s your sales philosophy right now?

Future-Proofing Sales In A Disrupted Market

I am highly focused on there being a lot of disruption coming into our business. We think a lot about the premium sales world and how we’re designing venues and how we’re going to go create these experiences. I am highly focused on us. Oftentimes we are thinking about designing and selling something that will not exist for 5, 6, sometimes longer years. We have got to get ahead of the trend. Right now I am very focused on how we sell against some of the commoditization and monoculture that’s going on writ large.

You’re seeing millennials get older, and they’re starting to get some more buying power. There is the wealth transfer going on from the baby boomer generation, but millennials, and I am one, we lived in the world of sameness and very slick minimalist design. The Chipotle looks the same, whether it’s in San Diego or New York, this millennial aesthetic, it was all stripped down and clean. We’re seeing this pendulum swing the other way with the Gen Z group. There is this real push against monoculture. There is also a huge push against materiality.

It will always be nice to buy nice things or buy luxury goods, but you’re actually seeing people buy used Hermès bags on eBay so that they can photograph it and put it on Instagram like they just came out of the store. They’re buying fake affluence, but the thing you cannot buy is standing pitchside at Chelsea for a match. As we’re thinking about first sale for our clients and selling into finding new partnerships, we’re talking a lot about that, as we can help partner with you on that journey.

Going down a level of what we would call a second sale, when we’re actually selling on behalf of our partners. It’s how we have that experience in that narrative that is highly personalized because live events will be the last thing to go. We’ve never seen more interest. See what’s going on with the World Cup and these other global events. People want to be together, and they want to live. They want to put their phone down and get off social media and have an enriching experience because of all the turmoil that’s going on in the world. We’re trying to sell into that disruption, showing how we can help our partners, but then ultimately, when we go to market, show that it’s more highly individualized.

Would you say that being adaptive to the disruptive environment is probably where it’s at?

Super adaptive. It goes back to the acronym from my father. Humility. When it’s not working, kill it fast, pivot, try something different. That’s never been more important.

When it’s not working, your dad has some of the best. I still have got to get this dinner with him. It has to happen. How do you summarize your leadership philosophy? It seems to me it’s stayed the same, but your perspective has changed. It’s the same, but your view is wider. I am not articulating you properly.

That’s right. I have the core frameworks from experience, as everybody else does. Everyone is shaped by their earlier experiences. As you progress as a leader, it definitely evolves. More so now than ever, I am very much on the front foot of how do I remove obstacles from my people? How do I make sure that the intent is clear so that they can go operate and do their best work? How do I make sure that I step back and provide the framework and the pathway for them ultimately to go do it? I made a conscious decision early in my career, and this might be a bit of the military or the hockey influence, but that I was going to be very transparent as a leader.

Sometimes I am overly transparent, but I am willing to walk on that side of the line because I think that that’s highly important as you’re managing a diverse global team, like the speed at which we move in our world right now and the amount of opportunity that’s out there and the disruption in the sports space in general. It’s just really important for people to have the psychological safety to know that they are part of the unit and that we’re going to get this done together.

It’s just really important for people to have the psychological safety to know that they are part of the unit and that we’re going to get this done together.

I’ve started to over-index even more on that, particularly the last three or four years, as my role and scope have changed because you do not have the time or the ability to go sit with all of the people I used to be able to go sit with. I cannot go to 150 venues. I get to Europe a lot. I am in Europe every 5 or 6 weeks right now, but you still do not have time to make it to every property in the given space of a couple months. How you project that and create a culture of that mentality so that it can have a trickle-down effect has been the real focus.

Earlier, we saw that transparency comes down to truth, duty, valor, as you talked to me earlier. I guess if you had to put it in a sentence or philosophy or quote for your leader?

It’s not about you. That’s like the go-to.

You can land it right there, man, because then it’s not about you. Firestorm of questions ready? That always has these questions. You’re going to get a massive deal done, and you’re flying overseas and thinking of the next big deal that you’re trying to get done, walking into the meeting or on the plane. What’s the song?

That’s great. I am probably going with something Tragically Hip. “New Orleans Is Sinking,” something along those lines. I’ll listen to something that will bring me back to being in the locker room in hockey. That was always The Tragically Hip, or something like I want to be back in that headspace.

Final Thoughts: Success, Time Management, And Legacy

Got it. It’s game time. You’re backwards to go forward. Besides my books, of course. What is the book, you and I? I still have The Children of Ash and Elm on my own. I literally looked at it last night. I started it, but I am not finishing. I have got six books going on right now. It’s a book about Vikings. Him and I, so a book you would give the most to an employee, to a customer? It would be a go-to. Every graduate I am going to graduation for my niece. That’s what I give. The place that you go. It’s sitting right behind me. There it is right there. What do you get?

Four Thousand Weeks by Oliver Burkeman. I read it recently. Six months ago I read it, and I’ve been gifting it to all kinds of people. The general thesis is that if you live to 80, you have about 4,000 weeks. It is a smack-you-in-the-face perspective, especially for people in the sales world with a million things going on. It’s just such a good perspective. He talks about time management, and you’re never going to do everything that you want to do, so just get comfortable with the idea that you’re making an opportunity cost decision. Enjoy the thing that you did pick. Do not always be pining for the other thing. Your inbox is always going to be Sisyphus. It’s never going to be empty, so stop worrying about it. Just a really good presence.

You’re always pushing the boulder. You know what? I am literally on my phone right now ordering the book. Four Thousand Weeks. It’s so good. You did not tell me that one before. Last question. What a great interview. You have got nieces or nephews, let’s say. You’re sitting on the edge of a dock. Niece to the left, nephew to the right. They’re 6 or 7 years old. They go, “Uncle Colin, what does it mean to be successful?” You say Remember Colin, a 6 or 7-year-old. You must quote it that way. Go.

To me, success means I’ve been pretty philosophical about this with some of the stuff that had gone on in my personal life the last few years. Ultimately, success is the ability to create a platform within your life where you get to do the things you want to do. If I was talking to a 6 or 7-year-old, I was just going to count you on that.

Success is the ability to create a platform within your life where you get to do the things you want to do.

I was like, no, platform is right.

If I was talking to a 6 or 7-year-old, I would just tell them, “Follow your instincts, and whatever you’re passionate about, chase it.”

Awesome advice. Colin, as always, man, verbal brevity. You get to the point. I always said about you, and I think this is really important, talk to a lot of leaders. It’s one thing to know what magnetic north is, what you get pulled to, but it’s a whole other game to know what that true north is. Every time I talk to you, I feel like you know that true north and all the different strategies and conversations you’re having. I appreciate you, my friend. I really do. Thank you for your time. It’s been fun to be along for the ride, man, seriously.

I would not be here without you. The ride’s just getting started is what I tell people all the time. That’s what it is.

I love it.

 

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