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By all appearances, by the time he was 40, was at the top of his game. He had been a two-time Olympic skier, earned his college degree despite setbacks and built an impressive career in private equity. But an industry conference triggered an epiphany—he realized he needed to do something with more heart. Heckman shared his story in a conversation with Leeds. Comments have been edited for length.

How did your Olympic training have an impact on your life and business?

It’s a big part of who I am. At 10, I wrote for a school paper that I wanted to be an Olympic skier and it was only six years later that I was in my first Olympics. I wasn’t very good at school or other sports, so I doubled down and leaned into something that I was good at. I went to my second Olympics when I was 18 and was ranked ninth in the world a year later. I learned to set big goals and accept small steps and required failures to attain them.

You mentioned on that it was a challenge to catch up academically in college.

It was a major challenge. I was older than most of the students, and I was woefully behind academically. And I kind of lost my identity that was so attached to skiing.

Naively, I had applied to Stanford, with no GPA, no ACT, no SAT, and I got like a “cease-and- desist” order from those guys! Then I applied to CU and got denied. I was scared I had messed up my whole future in the pursuit of my Olympic dream, but my librarian advocated for me to a CU admissions director who allowed me in but on probation. While it was hard and I felt beneath the other students academically, I felt a huge sense of privilege that I even got to go to college.

Those first couple of classes I took were so discouraging. I walked past the phone booth outside of my first classroom near Varsity Pond every day, and I was so tempted to call my coach and say, ‘College is not for me; I should go back to skiing.'

What kept you going? I imagine you have a built-in spirit of perseverance.

I did, and I still do today, but that would understate how emotionally challenging that situation was. Those first two years I was in general ed classes, and it seemed so far afield of my business goals that I chose over skiing. Imagine me going from being an Olympic athlete on television to being one of 500 students in a big auditorium and one of the dumbest kids in the class. I would say a little bit of fear motivated me; I didn’t want to fail.

Once I got into Leeds, I flourished. We had an accounting professor named Mad Dog MacFee, and it was a difficult class, but I got 100%. It was my first moment of victory. Then I graduated with a 3.98 GPA. I was summa cum laude. I was really proud of that and it gave me confidence outside of athletics.

I learned your first job offer came from a chance encounter on an airplane.

I was 16, and I rode on a flight to Zurich with a private equity investor named George Gillett. He owned Vail Resorts and other high-profile assets around the country. I talked to him the entire flight. When we got off the plane, he said, ‘If you graduate from college, give me a call.’

I called him my senior year and he invited me to a Broncos game. He asked me how much I wanted to make. I recalled my parents saying the most they had ever made was $40,000, so I said, ‘I’d like to make $40,000.’ George stuck his hand out and said, ‘How’s 37,500?’

And you went to work for him?

Yes. I thought I had really won the lottery because I was going to make all this money and live in Vail. It turned out that the job was with his M&A group in Atlanta.

I talk with a lot of young people who have grown up in Colorado, and I advise them to leave so they can come home and stay forever. When you’re first starting out, the geography of your job should be like number 20 on your list of criteria. You should look for where you’re going to get the most responsibility and coaching.��

What was your career trajectory to get to Rallyday?

I was with George Gillett for five years, six years at a private equity firm in Denver and then eight years at a firm I co-founded with some of my former colleagues.

Then something funny happened when I turned 40. I was at an industry conference in Orlando, Florida. I just had my daughter. I was in this room with 2,000 white males with blue blazers, loafers and a lanyard around their neck, and I thought: I don’t know if this is who I want to be long-term. I don’t know if I want my daughter to see me in this industry. It was not the clothes but the soulless feeling that sort of felt suffocating to me. I thought there was something more noble out there for me.����

Ultimately, I bought a small healthcare business in Denver with 11 employees and I applied my deal-making expertise. I had done a lot of healthcare investing, so I knew something about it. I hired an executive coach to help me with leading people, which I deployed across the whole organization. We all went on that journey together. I grew the business to 450 employees over five years.

That was a bold move to buy a company.

It was a huge move. I raised no outside capital. Building a business of that size without any outside capital is very difficult. We almost missed payroll about a dozen times, but the business ended up having $14 million in profit, and I sold it for a big number and several of my direct reports became millionaires.

In retrospect, it was probably the last thing I should have done after having a daughter! But I’m very proud of it, and it inspired me to imagine as an alternative to traditional private equity.

By having a human-centered focus, Rallyday is taking a radically different approach in the private equity industry.

We raised $150 million within six months. We had 97 meetings, and at the end, only five investors. Which means 92 people thought we were absolutely nuts.����

How did you keep your spirits up?

I believed in the mission and had total confidence in the outcome. I figured it was just a matter of when, not if. Our first investment was a research organization for the pharmaceutical industry. We put $20 million into it, and we returned the entire $150 million fund we had raised in two years with that one investment.����

My three partners and I have all built companies as a CEO and founder. It gives us a distinct advantage to connect with CEOs and founders on an emotional level. When things get hard, we can be a thought partner.

How do business schools play a role in teaching these ideals?

It’s not just a business school’s responsibility to teach these things. It’s the school’s responsibility to encourage students that they need to invest in themselves.

At Rallyday, we expect our employees to invest in their heart, mind and soul, and we have a leadership program that teaches what we call ‘super skills’—common skills performed at an elite level. For example, we have a curriculum to help teach people how to listen better, lead with empathy and other ‘soft’ skills that make the difference in the real world. Most of those skills are learned from challenging experiences that take you out of your comfort zone.

It sounds like you’re doing remarkable things at Rallyday.

We talk a lot about what makes a company legendary. Typically, there’s scope and there’s scale. But there’s a third way to become legendary, and that’s through the quality of your craft—to do something so special that people are attached to your purpose and way of doing things at an emotional level. Hermès handmade products in France come to mind. They are probably a thirtieth the size of Louis Vuitton, but they command 10 times the price for the same product. It's not the brand per se, it's the craftsman identity that creates more meaning to the product.

At Rallyday, our purpose is to empower leaders to create the most value for the most people and to share in the experience of a lifetime.��

What are your thoughts on the rapid adoption of AI?

I highly recommend that students read the book Empire of Wealth by John Steele Gordon. It does a great job of illuminating the dozens of economic transformational periods in our history.

We're at one of those times right now. The profundity of AI is that 5-10 times the amount of capital that went into the last wave of technology is now being applied to a technology that could triple our productivity as a society.

So how do we shape the future of business in positive ways?

In some ways you could argue it's sort of ‘back to the future.’ What happens when everybody in America can answer the same question in a matter of seconds that used to take 10 years? That levels the playing field of knowledge, so you have to differentiate yourself.

Ryan Heckman was among the panelists on the Funding Innovation Panel on Private Capital Markets hosted by the Burridge Center for Finance.