S4E6: Ryan Heckman - From Olympic Slopes to Entrepreneurial Success episode artwork

EPISODE · Mar 26, 2025 · 33 MIN

S4E6: Ryan Heckman - From Olympic Slopes to Entrepreneurial Success

from Leeds Business Insights · host Leeds School of Business

What does it look like to move from a life of intense athletic competition into the realm of business? What aspects of being an athlete translated well into entrepreneurship, and what strong career motivation can be derived from understanding a simple bell curve? Ryan Heckman is a two-time Olympian, Leeds Business School Alumnus, and a longtime 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.In this episode, Ryan discusses his unique career path to the world of private equity. Ryan shares personal anecdotes about his college journey, career challenges, and his midlife crisis-turned-awakening that led to the founding of Rallyday. He emphasizes the importance of integrating left brain, right brain, heart, and soul in business, and how Rallyday Partners is shifting the paradigm within the private equity industry through its focus on humanizing the journey and fostering aggressive humility among its leaders. Check out this fascinating conversation.Leeds Business Insights Podcast is a production of Leeds School of Business and is produced by University FM.EPISODE QUOTES:The higher the goals the greater the humility[12:11] 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.What differs Rallyday from traditional private equity firms? [14:48] “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.What does it mean to be aggressively humble at the same time[15:51] 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.SHOW LINKS:Ryan Heckman | RallyDay ProfileRyan Heckman | LinkedIn

What does it look like to move from a life of intense athletic competition into the realm of business? What aspects of being an athlete translated well into entrepreneurship, and what strong career motivation can be derived from understanding a simple bell curve? Ryan Heckman is a two-time Olympian, Leeds Business School Alumnus, and a longtime 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. In this episode, Ryan discusses his unique career path to the world of private equity. Ryan shares personal anecdotes about his college journey, career challenges, and his midlife crisis-turned-awakening that led to the founding of Rallyday. He emphasizes the importance of integrating left brain, right brain, heart, and soul in business, and how Rallyday Partners is shifting the paradigm within the private equity industry through its focus on humanizing the journey and fostering aggressive humility among its leaders. Check out this fascinating conversation. Leeds Business Insights Podcast is a production of Leeds School of Business and is produced by University FM. EPISODE QUOTES: The higher the goals the greater the humility [12:11] 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. What differs Rallyday from traditional private equity firms? [14:48] “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. What does it mean to be aggressively humble at the same time [15:51] 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. SHOW LINKS: Ryan Heckman | RallyDay Profile Ryan Heckman | LinkedIn

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What does it look like to move from a life of intense athletic competition into the realm of business? What aspects of being an athlete translated well into entrepreneurship, and what strong career motivation can be derived from understanding a...

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