Leeds Business Insights Season 4, Ep. 6: Ryan Heckman Transcript

Maria Kuntz: Today's LBIdea is to invest in your connection between the left and right brain, your heart, and your soul. Our guest today is Ryan Heckman, a two-time Olympian, Leeds alumnus, and long-time entrepreneur. Ryan co-founded Rallyday Partners, an investment firm dedicated to providing holistic support to company founders and their employees, where he serves as CEO and managing partner.

Thank you for joining us today, Ryan.

Ryan Heckman: I'm excited to be here. Thanks for having me.

Kuntz: Great. Well, we've got a lot to talk about. We're going to just dive right into questions. You were an Olympic skier before you became a student at C.U. Tell us why you chose to pursue a college education and what your experience was like at Leeds.

Heckman: Well, choosing to go to college was, I mean, always in the cards. I didn't intend on going my whole life without being educated. I think what made it a little harder was I didn't really go to high school. So, getting into college was a challenge, not wanting to go.

Ryan Heckman Headshot

I would add a third challenge, which was paying for it, of course. I lived with a really, I'd say, cute couple. They're in their 鈥90s now, but when I was younger, I lived with them. And she was a librarian at our school. And they both really valued education. And it was a year after my last Olympic games, they just said, "Look, you should go to college," and made the case. They also said that if I went then they would pay for the whole thing-

Kuntz: Wow.

Heckman: ... which was, kind of, a big...

Kuntz: Your angel investors.

Heckman: My angel investor. Good one. Certainly angels. That's for sure. But I applied to Stanford, and my joke is they sent me, like, a cease and desist order. It wasn't any reference to holding my application on file. Let's just put it that way. My backup plan was C.U. Nothing against C.U., but all my friends were going to C.U., so I just wanted to do something different, but-

Kuntz: Sure.

Heckman: ... I applied to C.U. and got denied again. A very thoughtful denial letter by comparison, but a denial, nevertheless. And Jane Hill, the librarian, went on my behalf to C.U. in 抖阴传媒在线 and met with one of your admissions counselors and convinced him to give me a shot. And so, they had me as an acceptance on a conditional basis and was on probation for two of the three years that I was at C.U. And so, yeah, it was, I guess, a blessing and a curse because I think when I did get into school, I just felt really lucky that I could go to college, you know, and probably showed up with more enthusiasm and more rigor because of the privileged feeling that I had. So, I think it fed me to work a little harder.

Kuntz: Thanks for sharing that. I mean, you think about the fact that you're an Olympic skier and then to share about rejections, right? Getting no's when maybe you're used to a lot of yeses in life. I think there's a lot that can be learned from that experience, both for the listeners, and I'm sure you learned a lot.

Heckman: I think that's insightful. I mean, the other part of it was just the irrelevancy that I felt on campus. It's a big school. Particularly, those general ed classes are typically, you know, 300 to 500 students. And to be one of the 300 to 500 and to be one of the least educated of them, having been on the world stage for as many years as I was, was just really a hard phase of my life.

There was a payphone outside near Varsity Pond that I passed in the first year I was at school seemingly every day. And my coach had told me that I was going to want to come back and ski and to just give him a call if I ever felt the need. And what I never told him was I wanted to come back skiing every day.

I mean, that did not go away. I missed my teammates. I missed the relevancy. I missed the competition. I missed being good at something really badly. I hadn't had that in a while. I didn't really have a lot of friends on campus. And every day I passed this payphone was a test of my conviction. And over time, it just strengthened my resolve to not just get done with school, but to kick some ass, you know, because I, I hated that payphone.

Kuntz: You probably never look at a payphone the same way most people do.

Heckman: Thankfully, none of us have to look at payphones anymore.

Kuntz: A relic.

Heckman: My wife tells me not to tell that story because she says it dates me, but I still tell it because it was so real.

Kuntz: There's a few out there. I saw one on a road trip in the middle of Southern Colorado.

Heckman: There you go.

Kuntz: Well, let's fast forward from that experience. And can you walk us through your career trajectory and what led you to found Rallyday?

Heckman: Well, that is a long story. I should finish with C.U., though, because-

Kuntz: Oh, yeah.

Heckman: ... I had a really good experience, particularly the last two years at Leeds, where I finally got to take, like, real business classes, you know, and I had some amazing professors. I also rode on an airplane before I started college with a private equity executive named George Gillett. And funny enough, George was on the speaking tour at C.U.-

Kuntz: Oh.

Heckman: ... my sophomore year.

Kuntz: Okay.

Heckman: And I had ridden on the airplane with him. And when I got done with the plane ride after talking his ear off for eight hours, he said, "If you ever get a college degree, give me a call. I'll give you a job." And so...

Kuntz: Nice.

Heckman: Yeah, I was pretty excited, but it'd been four or five, six years, I guess, since I'd seen him on that airplane-

Kuntz: Yeah.

Heckman: ... and he came, and he spoke in the law school building, and I went to attend his lecture. It was for post-graduate students only, but I snuck in and went up and reintroduced myself to him. And I just said, "Is the offer still there? I'm getting pretty close here." And he said, "Absolutely." So, you know, C.U. is just a great segue for me to get academic confidence, some inspiration, and serendipitously reconnect with the guy who gave me my first job. So, that was a tremendously valuable moment.

Kuntz: What an amazing story about connections, tenacity, dedication. Thank you so much for sharing all of that.

Heckman: Yeah. So, I started in private equity actually at a young age. Usually, the path is you do a couple of years of investment banking or whatever, and then you go get your MBA, and then you might get an interview at a private equity firm, but for example, I would never get a job at the firm that I run today. It's a very difficult field to get into and it's, kind of, an apprentice model. So, it's just brutal. And that I got in at the age of 23 was very lucky. And I've been doing it now for 26 years, two halves of my career.

First 15 years, my goal was to become a partner at one of these firms. And I did and started my own private equity firm with some friends, some fellow partners. And at 40, something weird happened to me. My friends say that I had a midlife crisis and give me grief about it. On reflection, I think it was more of an awakening, but I, I just didn't feel like being a private equity investor was noble. That's the only word I can come up with, but I didn't necessarily like the arrogance of my industry, backseat driving for a living, which is, kind of, what we do. Didn't seem all that, all that virtuous.

And I just thought there was something more in my life than investing like that. And I wanted to get closer to the action. So, I talked to the bunch of the CEOs that I supported. And unanimously, they all said, "We've been waiting for this conversation. You should just go be a CEO and just go jump in the deep end of the pool. And we have faith in you." The problem was nobody with a good company was going to hire me, like, because-

Kuntz: Right.

Heckman: ... you know, like, I had no credentials, no competency, and no track record that would get me even in the door and never mind land the job. And so, I bought a job. I mean, like, I'm unabashedly saying this on this podcast. I bought a little business with 11 employees. My office was above the tuxedo section at the Men's Wearhouse, which is not the best men's clothing store in the world. And it was just so funny to go up this spiral staircase amidst all the tuxedos. So, it was very humbling. And what's cool is, like, I built that business. It was a healthcare organization. And I built it from 11 employees to over 450 employees.

Kuntz: Wow.

Heckman: I grew our profit from under a half a million dollars to $14 million of profit and learned how to lead people. And it was just a transformational phase of my life. It was really hard. I would say it was way harder than my skiing career and maybe my school career put together because the pressures of running a business are hard, the pressures of running a business while it's doubling every three months is exponentially harder, and doing it as a first timer, I would liken it to showing up at a ski area and getting off a lift and heading straight to a black diamond-

Kuntz: Yeah.

Heckman:听... you know. Pretty stupid, actually, if you think about it, but, you know, I did it. And I knew how stupid it was. The proof is this. I would not take any outside money. So, I did all of that with only my money. So, the only thing that could prevent me from growing was my own capital, but it also helped me take this risk without worrying that I was going to endanger other people's lives.

Certainly, I felt an obligation to the employees, but taking other people's money is a big deal. And so, that was one way I mitigated any of the danger I could have caused by my stupidity, but it was just a great learning experience. I wouldn't trade it for anything. And then when I sold that business, the question was what next?

And I decided that I was going to take all of those learnings from being the CEO of this business, combine it with my disdain for private equity, and where I ended up at 40 with my mid-life crises, and reinvent the private equity industry right here in Colorado with two of my dear friends. And so, at Rallyday, we've been in the process of building a new kind of private equity firm now for five years. And it's been just a whole bunch of fun and adventure of a lifetime, I would say.

Kuntz: I mean, incredible. You know, I love it. You've taken all that competitive energy, the ability to apply, sort of, rigor and training to really follow passions and develop a dream.

Heckman: Yeah. One question I get sometimes is 鈥淲hat did I learn from my Olympic experience that I've applied to business?鈥 And there's a few things that stand out. One is that in an individual sport, I was competing against 100 of the best athletes every weekend. The odds of me winning were literally less than 1%, which also means that I spent most of my skiing career losing, right? I mean-

Kuntz: Yeah.

Heckman: ... 99% of the time. And that's hard. So, you learn to evaluate yourself not on, results, but on progress. And I think, in business, that is really important that you just wake up every day and try to get better each day and not focus necessarily on winning or losing. Just get better. So, that's been very helpful. A second one is that I don't necessarily mind failure if the intention was good. And in all of these cases, my biggest risks that I took, for example, leaving private equity and buying a business with 11 employees, and I didn't get paid for four years.

The why... to use Simon Sinek's word, the why was so strong that I didn't care about the what anymore. And I was willing to fail every day in pursuit of something that I thought was going to be more noteworthy in the long term. And the third one is just, I guess, the humility of the chase. And I would just say, like, the higher we set our goals, the more humility we generally have because the chances of you reaching those goals are very slim. And so, I think I've shown up, particularly the last 10 years, with a great deal more humility because of the audacity of the goals that I had established for myself seems so farfetched most of the time.

Kuntz: And yet, here you are, you are the CEO of a private equity firm.

Heckman: Ain't that wild?

Kuntz: So, you mentioned earlier that you have disdain for private equity. And I guess that means you're trying to do something or you're doing something quite different at Rallyday. Can you explain how it differs from traditional private equity firms?

Heckman: Well, there's a lot of structural differences, and I'll quickly do those, but there's a bigger conversation that's probably more evocative and profound. But functionally, the people who run Rallyday, at the very top, all were CEOs and founders. And I've always found it a little funny that most private equity funds, their leaders have never run a business and yet they're being paid to run businesses. So, I just find that curious.

And so, here at Rallyday, all of us have actually, like, made 1,000 mistakes that every one of our CEOs are going to make. And we try to help them not make those mistakes, but if they do, more importantly, earn the right to a phone call when they make a tragic mistake because they know we're going to help them through that as opposed to judging them for that.

And I think that empathy comes from our own mistakes and an acknowledgment when you're moving fast and you're trying to do something big, the odds of making mistakes along the way only go up. And so, we'd rather them be aggressive than avoid mistakes, I guess you could say. And they feel that from us every day. The second thing we've tried to do is, what I call, humanize the journey, which is to acknowledge that in our industry, typically, we talk about the assets that we manage. Like, that's a thing.

Kuntz: Yeah.

Heckman: And when you're at a industry conference or whatever, like, one of my peers will come to me and say, "Tell me about Rallyday." And the next question typically is, "How much assets do you have under management?" And it's a way of gauging how successful you are. It's almost like asking someone how big their bank account is-

Kuntz: Yeah.

Heckman: ... or what car do they drive, or what school do your kids go to, or where do you live in Denver. And my answer to them is always, "I manage zero assets." I follow that by saying, "We lead people. We don't manage assets." And what I mean by that is the objective is obviously professional. We want to create a lot of value, but the journey is very personal, you know.

Whether it be for the CEOs that we partner with or their executive teams, the middle managers, the employees, they're showing up at our workplace. And we treat that like the privilege that it is. And our obligation is to not manage them. No one likes to feel managed. We want to earn their followership, and we want to be their leaders and take them personally to places they didn't think they could before meeting us and take their companies even further because they're growing so much as individuals. And so, when we talk about what we do for a living, it's all about humanizing that journey very personally.

And then the third thing is just kindness and humility, you know. I know that sounds funny, but, like, that's actually a differentiator in our industry. I think that everybody at Rallyday strives to be two things at the same time. We strive to be aggressively humble. And what that means, there's a lot of people that I know who are super aggressive and super not humble. I also know people that are really humble, but typically not very aggressive. And so, we look for this duality of character. And, you know, as it turns out, it works because there's nothing more special than someone that is both of these things at the same time.

Kuntz: Yeah. You have shared in previous conversations that you bring fginto the investing world, that spirituality is really important to you. How do you bring that into the world? How do you bring that into these interactions, into the work that you do with these leaders?

Heckman: Let's start with what I mean by the word spirituality, maybe to start-

Kuntz: Let's start there. Yeah.

Heckman: I would just suggest that we are all raised in school, starting in school, even at a very young age. My first recollection of my grades that I took home to my parents was in the third grade. I think before then, it was, kind of, E's and S's and-

Kuntz: Sure.

Heckman: ... so forth.

Kuntz: Excellent. Satisfactory.

Heckman: Yeah. There was one... I, I forget the year. I think it was third grade, though, might have been fourth, when there was, like, A, B, C, D, and F, right? Like, all of a sudden, like, that meant something. And the way you got those grades was by learning knowledge and then being able to regurgitate that knowledge in an exam or on a paper or in your homework or whatever. So, very left-brain activity. And the reward system was built to reward an overabundance of rigor as it relates to the left brain.

Now, you might have had an art class in there somewhere, P.E., but generally speaking, we are hardwired to do really well test taking. And then if you do really well on those tests, you get into a college, like the university of Colorado Leeds School of Business, where the same thing happens, you know, how good you are on your tests results in a grade point average, which then helps you get a job. And so, basically, for about 18 years, 19 years, in my case it was 23 years because it took me a little longer to finish school, you're rewarded on your left brain.

Kuntz: Yeah.

Heckman: And I think it wasn't until I left private equity that I just saw how silly this was, that the right brain was really powerful and that the heart was really powerful. There's an expression that people don't quit their jobs. They quit their bosses. Well, that's all about the heart, right?

Kuntz: Yeah.

Heckman: Think of a boss that you really enjoy reporting to. And it, it's not because they're good at taking a test.

Kuntz: Right.

Heckman: It's because you believe in their heart, and you believe that their heart believes in you back. Like, there's a thing. And then there's your soul. And the soul is, kind of, a interesting word that means different things to different people, but what I've tried to do the last 10 years is try to honor all four of those together, so left brain, right brain, heart, and soul. And I spent a lot of time working in all four of those realms.

And I'll give you some reasons why this is important. So, in business, if you don't innovate, especially today, your business is going to be gone because the rate of innovation is happening, and somebody is doing it. And if you're not doing it, you're getting left behind, and that business will wither away. Well, innovation comes from the word creativity. That has nothing to do with your left brain. Nothing. Leading people. We've talked about this briefly as an anecdote, but when it comes to leading people, the first job is to deserve a follower. And you do that through the demonstration of your character.

Again, character has nothing to do with your left brain. Problem solving. This is a good one. We oftentimes solve problems with our left brain and realize that curiosity, asking more questions before you start processing, could have given you a shortcut to solving that problem, but curiosity comes from a wholly different place than your left brain. In fact, your left brain tends to override your curiosity. Creating value.

You know, at the end of the day, consumers pay a certain price for your product or service, and they're willing to pay that price because the value that they get is an excess of the price. That's how it works. You go buy a car. It better do a little better than what you paid for it, right? When you're at work, the people that we remember that add the most to an organization are those that are in service to that organization. Well, that doesn't come from your left brain.

Kuntz: No.

Heckman: That comes from your soul and your spirit and your heart. It means that you're motivated by serving other people. There's a word, servant leadership. Well, that is not something that you learn by taking an exam. You learn that through experiences. And the last one is just, you know, going back to innovation but at a very personal level is the ability to be continuously learning. So, not joking you when I make this comment, but I am learning at a faster pace today than I did when I was in college or any time thereafter.

I'm on a increasingly steep learning curve at this phase of my career. And that comes from humility. That comes from this acknowledgment I've only reached maybe half of my potential. And damn it, Ryan, I really want to do better. And the only way I'm going to reach that potential, which might be elusive, is to make sure that I'm always learning. And that's humility.

And so, when you add these all up, creativity, your character, your sense of curiosity, your aspiration for service to others, your own internal humility, these are things that we're almost discouraged from exploring in our educational system. And you, kind of, have to seek these out elsewhere, put yourself in uncomfortable experiences, to obtain these things. And so, when I talk about spirituality, it means investing in your spirituality, which is the, for me, the definition means the connection between your left brain, your right brain, your heart, and your soul.

Kuntz: That's really beautiful. I just learned a lot. I'm going to be reflecting and listening to this after it's published. How is this received by the world around you? I mean, there are probably people who are just dying to work with you, and maybe there's some people who are like, "Not my flavor." What has that experience been like?

Heckman: I'd have to go back to the principle of the mountain of average. It's this principle. It's a framework. It's the simplest framework in the world, but it basically says that in every field, every classroom, every office building, every sport, that there's a bell curve. And now that we're speaking at the University of Colorado Leeds School of Business, we all know what a bell curve means.

For me, it meant a savior from my poor grade, but a bell curve basically says that in any endeavor, there's the left hand tail, which are the underperformers, then that's, like, let's just say 10%, you know, they don't get it, they're not motivated, they're not working, and they're getting really bad grades. On the other end of that bell curve is the other 10%. That other 10% are the people who are changing the world. Those are the people that are doing exceptional things in service to an objective and to audacity that is more powerful than anyone can even imagine. Think of Elon Musk. He lives over there.

Kuntz: Yeah.

Heckman: Okay? And I know he's not very popular right now, but if you think about people who have changed our world... Throw Steve Jobs in there if it's more comfortable to you. Take Jeff Bezos and put him in there. Take Ruth Ginsburg. Put her in there. These people are living a life that is oftentimes misunderstood by the middle, which is the mountain of average, the 80% that live in that bell curve, who are simply looking for the most comfortable way to succeed. And just repeat those words. They're looking for the most comfortable way to succeed as defined by their school or by their parents.

Kuntz: Or their community.

Heckman: Whatever.

Kuntz: Yeah.

Heckman: Like, it's all about meeting somebody else's view of them. And they're just trying to get there as comfortably as possible. And by the way, we all live in various... at different points of our lives in this bell curve, but I believe that Rallyday is living on the far right of the bell curve. And I fully expect for at least 80, if not 90% of our industry to think that we have lost our minds. And when I get to that level doing anything, I should add, I know I'm on the right track. If people shake their head, roll their eyes, ask me what the hell I'm doing, it usually means-

Kuntz: You're on the path. You're on your path.

Heckman: ... I'm on the path, I'm on the path to greatness. And so, we're proud of maybe being the misfits as defined by 80% of our industry. It's something that we wear with a badge of honor.

Kuntz: And I mean, forgive me if I wasn't even thinking misfits. I think that when hearing you describe the work you all do, I think people who want to be CEOs, want to be leaders, are seeking greatness, but the way in which you pursue greatness is a calling to something very deep, very demanding, that even for... if you took bell curve of all the people who said they want to be great CEOs and great leaders, there's a mountain of middle there, and not everyone's willing to work and function and build a company in the way you're describing and the types of communities you're building and the leaders you're developing through the mentorship you're describing.

Heckman: Well, and as it turns out, when we are looking for, like, the very best CEOs that are going to do really special things in their industries, we're looking for CEOs with creativity.

Kuntz: Yeah.

Heckman: We're looking with ones that have an exemplary amount of character. We're looking for CEOs that are showing up every single day with a curious mindset. We're looking for CEOs who are servant leaders. And we're looking for leaders who don't just act humble but are actually humble on the inside.

And in this case, they're attracted to Rallyday because they found their place, they found their people, they found a place where we're going to celebrate them every single day and pick them up when they fail, which they will, and they found a partner who is going to be there through thick and thin and join them and be additive to their desire to do something exemplary and extraordinary. We were looking for leaders who want to build legendary businesses.

Kuntz: How do you find that? Like, how do you know when you're seeing someone who's got the character, has the curious mind, and might be the next person to build a legendary business?

Heckman: I would liken it to finding a good partner or someone to marry. It's, sort of, a random walk in many ways, but there's a certain chemistry that happens to all of us when we meet that person who really arouses our spirits, you know, where it's like, you get, like, a goosebumps.

Okay? And in business, it's no different. A lot of times, we'll meet leaders for the first time here in Denver at our headquarters in Cherry Creek. And I mean, you can usually tell within the first five minutes, you know, and it's because that chemistry gets made. It's like finding your soulmate, I guess you could say. And it's our job to be out there in the market and let other founders and CEOs know that we exist and just have a cup of coffee together and find out if our goals are aligned and see if the chemistry thing happens, you know.

Kuntz: Yeah.

Heckman: I mean, I get it.

Kuntz: Great. Well, what advice would you give to current or aspiring entrepreneurs or even students based on your experiences?

Heckman: Well, it should be implied at this point, but don't let the work get in the way of your life. What I mean by that is the days of work-life balance are... I think a lot of us have concluded that doesn't exist. I think a more evolved version of that is that you just have an integrated life. COVID helped us with this, you know. You're constantly going in and out of work and life. I think that work can very easily consume you.

And the kind of work I'm talking about is like the work of impressing others or meeting other people's standards or the pressure of performing, so performative work. And if that does consume you, you aren't experiencing life. And as we talked about, the only way that spirituality gets any power is from doing things outside of work and having that higher calling that you talked about. My mom taught third grade for, like, 30 years. And it was a really crummy job.

I mean, she made no money. The students were very painful at times, especially in the third grade. And their parents, sometimes, were very painful. And she would skip home from work every single day because a third grader learned to write the letter E for the first time or read an entire sentence for the first time that day. And I think that that becomes central to people who want to live this different way of living to find those sources of accomplishment and fulfillment versus through the eyes of other people.

So, I think whether you're a student or you're a founder, just feed your soul and be in service to other people and do get good grades because when you get good grades, you get to pick your boss. And that's very important. You don't want a boss to pick you because you may not want to follow that person, but when you do really well in school, and you have a good reputation, and you've got a resume that says you did other things, and just show up for class, a lot of organizations and people are out looking for you, and then you get to choose your job as opposed to the other way around. So, I think that's critical.

And for the founders, it's just so scary. You know, when you're running a new business that's got a lot of risk, I'm telling you it is one of the scariest things I've ever done in my life. And usually, the demons would come out at night. One of the things that I think helps a lot is to make sure that you've got a... either a business partner that you can share some of that burden with, you have a good friend outside of work, someone that you can confide in, or best yet, you have a partner, a wife, a husband, a partner who is going to pick you up at the end of those tough days and be there for you when nobody else is, and that's going to help you get through the adversity, because starting a business is the easy part.

It's building a flourishing business is the hard part. And that takes a long time and a lot of failure. And you're going to feel that every day. And it can crush you. It certainly had its moments of crushing me. So, I think surrounding yourself with some people who really care for you deeply and help feed your soul is very important.

Kuntz: Ryan, thank you so much for being a guest today. I think listeners, students, entrepreneurs are going to have a lot to listen to, learn from, and really reflect on.

Heckman: Well, thanks for the opportunity. I have been spending more time at Leeds lately. And it's been really fun. It's not that I forgot about C.U., but, I don't know, I guess I'm, like, in this phase of life where being around young people and being back at the university is, is really fulfilling.

Kuntz: Wonderful.

Heckman: So, I hope this is just the beginning of more work that I can do there in service to the school's future. I'm very proud and honored to be an alumni.

Kuntz: Wonderful. If somebody did want to get in touch with you, a student, another alum, what's the best way for them to reach out?

Heckman: You know, I would say LinkedIn is probably the best because there you're going to get a caricature, I do a fair amount of posting. By the way, at the intersection of spirituality and business is what I write a lot about. And so, they're going to get some good content. And you can always direct message me. And I check those about once a month. And, you know, I will make sure I find you if you find me.

Kuntz: Wonderful. Thank you so much for your time. We really appreciate having you as a guest.

Heckman: Thank you.

Kuntz: Thank you again for listening to Leeds Business Insights. Make sure you're one of the first to hear every episode by subscribing to the show wherever you get your podcasts. Leeds Business Insights podcast is a production of the Leeds School of Business and is produced by University FM. We'll see you next time.