Ishould have ended up as a lifer in the U.S. Armed Forces. Instead, I’m a five-time tech industry CEO who created over $4 billion in corporate value and took Weave public on the New York Stock Exchange. This journey has led me to a fascinating place in life. I’m truly excited, yet humbled, about the opportunity to help others toward success and freedom as a venture partner with Pelion Venture Partners, Utah’s largest venture capital (VC) firm.

Where to begin

In the early 1970s, a Black U.S. airman from Texarkana, Texas, met a German “Fräulein” while stationed in Europe. That initial meeting led to marriage, my birth near Amsterdam and a childhood in Germany, the Philippines and all over the U.S. before landing in Great Falls, Montana.

After my father retired in 1980, he struggled to find a decent-paying civilian job to supplement his meager pension. We struggled to make ends meet even with food stamps and other assistance. So, in my early teens, I landed a job bagging groceries at the base commissary. With no hourly wage, I only got tips from customers, meaning I had to provide outstanding service.

I made $25 to $30 a day in tips, which was incredible money in the 1980s—especially for a boy in his early teens. After my shifts, I gave the money to my mother, who took what was needed to pay bills—anything remaining she gave back to me.

I met interesting people from all over the world as a bag boy, and I became an astute observer of their behaviors. I also learned valuable communication and engagement skills that helped me as I grew older. 

Looking back, this is probably one of the biggest learning experiences I’ve had in my life, but it’s not a sob story. From my perspective, this was just what families did when things were tough: close ranks and pull together. This is also true in business; you pull together and move forward.

I dated a girl in high school who changed my life forever and became my future wife, Kristy. We married shortly after graduating, and I attended college using student loans. I worked three jobs during school, but then our first son got sick and was hospitalized. In an instant, we were under a mountain of medical debt and down to our last month’s rent. I was failing school, overworked and exhausted.

Without telling Kristy, I went to the Military Entrance Processing Station one morning in 1987. Recruiters from each military branch were stationed there. I went to enlist in the Air Force, but the wait to join was nine months. I needed to enlist, or we wouldn’t have a place to live. Disappointed and not knowing what to do, I turned to leave the building. Then, the Navy recruiter said, “Couldn’t get in, could you? How about this? How about you come and join the Navy?” 

I’d never even considered the Navy. I’d never seen a ship or the ocean or even a sailor. But he closed with this line, “I have a job for you; you could be a software engineer. I can get you into boot camp in literally a month, and you can earn the G.I. Bill to pay for college when your Navy service is over.” 

That was all I needed to hear; I enlisted on the spot, and it was the best business decision I ever made. Then, after five years of active duty, it became apparent that, with my vocation, I could triple my pay by entering civilian life. I left the service, and we moved to Utah to be near our families. 

Because of my software training and experience, I got a job at WordPerfect in research and development within one week. I started attending what is now Utah Valley University, the G.I. Bill and Pell Grants paid for college, and I changed my major to business management. I worked and went to school full-time until I graduated in 1996 with a bachelor’s degree in business management. 

During this time, I stayed with WordPerfect through a few transitions and eventually moved into product marketing. Then, I joined a few other tech companies in the early Silicon Slopes era, and my career took an interesting turn.

From software marketing to C-suite executive

A former WordPerfect colleague contacted me in 1999 about this back-end software platform that handled credit card processing so people could buy stuff directly online. Back then, if you wanted to buy something on a website, you called a 1-800 number on the homepage to make the actual purchase. I told him, “No thanks,” because I wasn’t sold on this whole e-commerce idea. However, John Bodine reached out to me again three months later—“Roy, this is going to change the world, and we really need you on our team.” 

After thinking about it a bit more, this innovative, disruptive and transformative e-commerce concept stuck with me. Being a part of something that could literally create an industry was intriguing. I realized this technological inflection point could completely change how we bought and sold products and services. So I joined the 10-person startup in Provo called Authorize.Net. 

One thing I’ve learned throughout my career is that no matter how unique, innovative or creative an idea may be, there are always others working on that same idea. The differences between those who succeed and those who fail are execution, determination, timing and a bit of luck. At Authorize.Net, we had all four.

I eventually became president of Authorize.net, and we ushered in the e-commerce era. Interestingly, we sold the company three separate times: first to GoToNet for $90.5 million, then to Lightbridge for $82 million and finally, to CyberSource for $662 million in 2005. 

This three-part sale journey gave me the equivalent of a real-world MBA with specialties in mergers & acquisitions, investment banking and financial engineering (aka, creating corporate value). During the latter part of my time with Authorize.net, I was approached by several private equity groups (PEGs), and each invited me to join one of their portfolio companies. 

This was my first exposure to PEGs, and the more I learned about them, the more I liked what they were about. After selling Authorize.Net to CyberSource, I was asked to serve as CEO of a PEG portfolio company that had recently been taken private. Thus began an entirely new and exciting stage of my career as I discovered an incredible financial formula: 

• Buy a company for $100 million to $200 million.
• Invest in its growth.
• Execute some financial engineering.
• Sell the company for two to three times what you paid for it after three to four years.

This is exactly what we did with that first company.

As it turns out, I ended up doing this same thing three different times within 10 years. I almost felt like I had to look over my shoulder as I thought, “Okay, it’s not easy. But how come other people don’t know about this?” They did. But I learned how to leverage debt and invest capital into innovative, disruptive and transformative companies to accelerate growth and increase value—all while in Utah. 

During those years, I helped bring several firms to Utah and created thousands of jobs. I’m very proud of these accomplishments, not because of the money I made, but because we blessed lives through job creation, helping people provide for families, buy homes and send kids on missions and/or to college. Then, suddenly, I retired. I was done. Except, clearly, I wasn’t.

From retirement to venture capital partner

I retired in 2019. Was it all it was cracked up to be? No, of course not.

During my retirement, I was contacted by Blake Modersitzki and Chris Cooper of Pelion Venture Partners and asked if I’d be interested in interviewing for the CEO position at Weave. I had known Blake and Chris since the 1990s when we all worked at WordPerfect. Their sales pitch was straightforward: “We know what you’ve done over the past 20 years. We’re considering taking Weave public, and we’d like you to interview for the job.”

Naturally, I was intrigued. I knew Pelion. I knew of Weave. I’d seen what both had accomplished. But I had never taken a company public. However, as someone who loves doing hard things, I went through the interview process and started as Weave’s CEO in December 2020. 

From the beginning, I had marching orders from the Board of Directors to take the company public in 2021. I dove in, quickly learning as much as I could by partnering with mentors and advisors. I worked on boosting the company’s operations while preparing for the Initial Public Offering (IPO). As we progressed through the year, it became clear that the fourth quarter would be our likely IPO time frame.

Taking a company public includes many exciting decisions. One of them is selecting an exchange where your company’s shares can be traded—NASDAQ or the New York Stock Exchange (NYSE). Both exchanges are excellent and offer different benefits, but the NYSE made an interesting pitch. 

Knowing I was a U.S. Navy Veteran, they suggested, “Wouldn’t it be cool to have a veteran take a company public on Veteran’s Day?” While this wasn’t the sole reason we selected the NYSE, it was a wonderful gesture on their part that helped me make my decision about where we listed the company. On November 11, 2021, Weave completed its IPO and became a public company, raising $120 million in the process.

It was surreal. Here’s this small-town kid from Great Falls going to Wall Street, ringing the bell to start the trading day on Veteran’s Day and signing a book of other companies that have listed on the New York Stock Exchange. It was also my 35th wedding anniversary, and my wife was able to join me!

What also made the IPO special was to do it as a CEO who happens to be Black. I know some people will always view me as a Black CEO and not simply a CEO. Regardless of how the word “Black” fits, I hope it’s an example and an inspiration. I hope others believe they can do the same or accomplish even more when someone who looks like me achieves the many things I’ve done throughout my career. They can do it right here in Utah, where anything is possible. 

While Utah, like other states in our country, must continue to encourage and guarantee equal opportunity and access to people of all races, ethnicities, backgrounds, religions and genders, my career has thrived here because people invested in me, believed in me, helped me believe in myself and saw me for who I am—not just what I look like. And I am truly grateful to Utah for the growth and development I’ve experienced here, both personally and professionally.

After the IPO, the Board asked me to stay and run the company. But I’m not a public company CEO. For a number of personal and health-related issues, I stepped away from Weave 11 months after the IPO and retired again in September 2022. Except … Blake and Chris reached out to me, again.

This time they had a different offer: “Why don’t you join our firm as a venture partner?” When they described the role of a venture partner, I immediately thought, “This is how I can pay forward what others have done for me.” 

I define a leader as someone with the ability to see in others what they don’t see in themselves who then helps others achieve their true potential. While I will continue to sit on various boards and advise companies, I now have the opportunity to serve as a mentor to entrepreneurs, founders, CEOs and executives in a peer-to-peer relationship. I can share my experiences, lend my expertise and help them navigate the complexities and challenges of building and growing successful companies.

In other words, I hope to have the courage to share with others the mistakes I’ve made so they don’t make the same mistakes.