How These CEOs are Living a Life of Climb
The journey to true leadership isn’t easy. Like climbing Denali, K2 or Everest, it’s the challenge of a lifetime. It’s for those with enough grit and commitment to rise to the occasion every day.
While each CEO’s journey to the summit is their own, they don’t have to do it alone. Through Vistage, they each have a team of peers, a seasoned guide and world-class tools and resources to lean into.
They’re all heroes on their unique leadership journey, lifting everyone around them as they ascend to new peaks.
Ryan Hogan, CEO of Hunt A Killer
Ryan Hogan is the CEO and co-founder of Hunt A Killer, an immservice game subscription where people play detectives in a mystery story. Each month, subscribers receive a red-and-black box with clues, ciphers and documents for investigating a case. The stories change frequently, with six episodes in every “season,” and shift between the genres of horror, sci-fi and mystery.
He has used storytelling to grow revenues at his company from $132,000 in 2016 to more than $27 million in 2019. In 2021, revenues are on track to exceed $50 million.
Hogan is quick to point out that his business growth didn’t come easy. Co-founder Derrick Smith shipped the first batch of 1,500 mystery boxes out of his basement in Baltimore, Maryland, and used a local printer to produce the content. “We didn’t start off doing things amazingly. We listened to our customers, and iterated the experience,” says Smith.
Hogan’s long-term vision for Hunt A Killer drives the necessary changes he needed to make in his business to ensure his company’s success: “At the end of the day, we’re not an event company, a subscription box company or a retail company,” he says. “We’re an organization that wants to bring the world together through immersive experiences.
Hogan’s CEO tips on expanding your company:
- Listen to your customers
- Iterate their feedback and grow with their needs
- Prioritize authenticity in your products
- Keep your customers engaged by giving them a community
Apolonia Rockwell, Founder & CEO of True Safety Services
Since the passing of her dear family friend, Apolonia Rockwell has made it her mission to enhance onsite safety in the workplace. She started her company to ensure every business has the right resources, training, and expertise to improve employee safety. As a first-time CEO, she struggled with taking her company to the next-level. She was feeling stuck in day-to-day activities and felt unsure on how to execute her bigger-vision goals.
“Once I joined Vistage, I quickly understood the value of building a strong leadership team. After that, everything changed. I finally had the freedom to be the visionary that my company needed.“
Apolonia learned how to assemble a strong foundation of leaders. The leadership skills she learned from Vistage helped her attract top talent and cultivate a positive culture for her employees. She learned the value of having employees who share the same core ideals.
“Today I have a strong leadership team rowing in the same direction. My business is growing, I’m attracting top talent and creating an inspiring company culture with everyone committed to the same core values.”
Apolonia’s CEO advice to new leaders:
- Carve out time for your company’s big-picture goals
- Stop doing everything and start doing the right things for your business
- Grow a team of leaders who share the same values Step out of the weeds to be the visionary your company needs
Mike Rydin, Founder & CEO of HCSS
In 1986, with no business education “or ever having read a business book,” Mike Rydin founded a software company for the construction industry out of his bedroom in Sugarland, Texas. Total revenue for that first year was $8,000.
After 10 years of running HCSS, Rydin built the company to a dozen employees and $1 million in revenue. Still, he found himself stymied — with every staff member coming to him for everything all of the time. “I was up to my eyeballs, constantly working out the day-to-day problems of the business,” he says.
It was at that point in 1996, he knew he had to get out of the weeds and start delegating in order to scale. That’s when Rydin joined Vistage. From then on, he says, he was immersed in business information, books and ideas from speakers across the country.
“I was getting thoughts from everywhere on how to run a business, which gave me an amazing amount of knowledge to apply to any problem that arose. I was also getting a lot of help from my Chairs — I’ve had three since I became a member 25 years ago — and from my fellow Vistage members. I’ve learned from everyone. It turns out most of us have the same kinds of problems.”
Today, with 400 full-time employees and about 4,000 contractors across North America, many of whom are heavy highway infrastructure professionals, HCSS plays a critical role in helping to build the backbone of this country. Occupying a huge campus with three buildings, the company surpassed $100 million in annual revenue in 2020 and continues to grow, expand and thrive.
“The fact that during the first 10 years we went from $10,000 to $1 million— and in the next 15 or 20 years we went from $1 million to $100 million — I’m absolutely certain that we couldn’t have done all the clever things we did, or have grown to that size, without Vistage,” says Rydin.
Mike’s CEO tips on running a fast-growing business:
- Build a team of leaders to work as the backbone of your company as it grows
- Let yourself learn from other leaders, CEOs, businesses, and challenges
- Delegate work orders to other tiers of employees
- Allow managers to handle day-to-day problems
Shaun Castillo, President of Preferred Technologies
A West Point graduate, Shaun Castillo exited the Army in 2005 with no formal business education but with a strong desire to start a company with his dad, an entrepreneur.
They founded Preferred Technologies, a security integration company. “My dad started out as president while I was running operations. After a few years he graciously stepped back so I could take the reins,” says Castillo.
“By 2015, the business was solvent and with sizeable revenue, but wasn’t making profit. I was still figuring things out and making financial mistakes when I received an email from Vistage Chair, Ken Proctor. The email struck me the right way, so I agreed to meet with him.”
Shaun said that after just a few meetings and one-on-one coaching sessions, he realized he had been making bad business decisions. ”I was struggling to figure out how the heck our company was going to make money. The group helped illuminate key obstacles that were getting in my way.”
He largely credits his turn for success to his interaction with his group members and Chair. Castillo says he had “instant trust” with his group of peers and learned how to openly discuss his weaknesses and ask for help. “We put everything on the table — our business problems, personal issues, kids — whatever comes up. I do ‘life’ with this group, and the experience has fundamentally changed who I am and how I lead the company.”
Shaun’s advice on overcoming poor financial decisions:
- Analyze financial information from comparative companies
- Price your products based on value
- Build a budget – and stick to it!
- Transition from a historical financial view to a forecast view
- Leverage your debt
Darren James, President of KAI Enterprises
Darren James wanted a way to meld his work as an architect and civic leader toward impacting undeserved communities.
When you look at Darren James’ career, it’s hard to tell where his work as a professional architect ends and his work as a civic leader begins.
“It was never the plan, but they’re so intertwined,” says James. “A lot of the work I do is truly going to transform Dallas for the better, and it overlaps what I do on a daily basis. I joke from time to time that KAI is my night job.”
To clarify, James is president of KAI Enterprises, an integrated architectural, engineering and construction services firm. But he also sits on several boards in the Dallas-Fort Worth area, affecting civic change that’s as substantial as erecting new buildings.
Most notably, James is chair of the Dallas Black Chamber of Commerce — the oldest continually operated Black chamber in the United States — and board president of Fair Park
First, a revitalization committee overseeing the restoration and management of Fair Park, home to both the State Fair of Texas and a history of racial animus. Taking on such roles is hardly the path of least resistance, but James says they’ve led to high rewards. “I’ve been able to take my experiences and grow my business and open some doors at KAI,” he says. “But I also have a responsibility to take the information I have and share that with others so that they have similar opportunities.”
James has learned a few tricks to manage his responsibilities, from being aware of his energy levels to delegating and taking time off to recharge. He’s also found a resource in his Vistage Chair, Becky Powell Schwartz, who helps clarify issues with James on both forand nonprofit challenges.
The chamber has seen a huge uptick in membership this year, the Dallas City Council approved the board’s master plan for Fair Park and KAI is expanding its operations. All of which means James is ready for his next “day job.”
“It goes back to why I wanted to be an architect,” he says. “The community can and should be better, and if I’m not going to do it, who is? I want to be part of the solution.”
CEO Tips from Becky Powell-Schwartz, Darren’s Chair
- Listen with an open mind and be OK with discomfort. Darren listens to all sides and, given the institutions, he deals with a lot of discomfort. But that helps him get to a win-win solution for all.
- Create a culture of trust. Darren is great at building teams he can delegate to. He leverages his time and talents toward developing and mentoring teams that can work independently.
- Walk your talk. A lot of people give you lip service. Not Darren. He doesn’t just say it, he does it.
Vassar Byrd, CEO of Rose Villa Inc.
Vassar was an economist with a master’s degree from the London School of Economics who felt like she could do more. After complaining about horrific conditions in an elder living facility where she volunteered, a friend challenged her to do something about it.
That’s when she decided to create a community that was different than anything she had seen. In 2006, she became CEO of Rose Villa, a dilapidated community with no infrastructure development and few computers. When Vassar joined Vistage in 2010, they had a vision of what it could be — and needed $70M to get there. While she couldn’t be fully transparent with her direct reports at the time, she could share her journey with her Vistage peers. They helped her think through decisions, vet ideas, and gain her footing. The group and Vistage Chair supported her every step of the way.
Today Rose Villa is a nationally known, state-of-the-art community with several net-zero energy neighborhoods and in the final phase of a $166M expansion. Vassar’s staff is fully empowered, allowing her to focus on the big vision — to grow and evolve.
Michael B. Russell, CEO of H.J. Russell & Company
In 2003, Michael B. Russell became CEO of the Atlanta-based H. J. Russell & Company (Russell). His father, Herman J. Russell, had started the firm 50 years earlier as a plastering business and built it into the nation’s largest African American-owned construction-services company.
Under the elder Russell’s leadership, the firm had defined the Atlanta skyline, building iconic structures including Atlanta’s Olympic Stadium, Hartsfield-Jackson Atlanta International Airport, the Coca-Cola Headquarters, and the Georgia World Congress Center.
The company was also a longtime pillar of the civil rights movement, both financially and otherwise. In the 1960s, Dr. Martin Luther King, Jr. would regularly hold meetings with other civil rights leaders at the Russell family home.
Over the next decade, Michael worked with his family to expand their operations into Texas, North Carolina and Alabama. The company built the University of North Carolina-Charlotte’s 49ers Football Complex, renovated terminals at Dallas/Fort Worth International Airport, and completed the National Center for Bioethics at Tuskegee University.
Michael didn’t forget his roots: The company helped construct Mercedes-Benz Stadium, home to the NFL’s Atlanta Falcons.
Then Michael got a call that would add to the company’s civil rights legacy: Help build the Smithsonian’s National Museum of African American History and Culture in Washington D.C. Russell was selected as the project’s construction management at-risk firm, monitoring the buildout of the 400,000-square-foot facility, 60% of which is below ground. When the museum broke ground in February 2012, the company supervised the 70-foot excavation needed for the building and made sure it wouldn’t destroy an underground water table or destabilize nearby buildings like, say, the Washington Monument.
Michael joined Vistage in 2009 on a friend’s recommendation. It came during a time in Michael’s career when he needed a better sounding board to deal with internal company issues. “I felt that I was on an island trying to make decisions by myself,” he says.
Michael’s Vistage group in Atlanta has helped him overhaul his hiring practices so that he brings in executives who are the right fit for the company. Specifically, he hired an industrial psychologist to make sure the work style of new hires meshed with their colleagues and the company overall.
Michael has also taken to heart the statistics surrounding family businesses, knowing that second-generation businesses only have a 30% success rate — and third-generation businesses even less. For Michael, G3 is about ensuring the long-term success of his company and family.
“Some of what we do today doesn’t necessarily mean that we need to do the same thing tomorrow,” says Russell, who was recently named to the Atlanta Business Chronicle’s “Power 100,” which highlights the city’s most influential residents, and was named as one of 28 CEOs to watch by Family Business Magazine in October 2021. “We’re trying to keep as entrepreneurial as we can, which allows people to leverage what we do today into possibly something different tomorrow.”
JC Maldonado, CEO of BizGro Partners
JC Maldonado wasn’t raised in a family of entrepreneurs. By the time he was in college, he knew he wanted to run a business. Luckily, Fordham University had evening classes, so, while pursuing a law degree by night, he founded a mergers and acquisition company by day. That was in 2000 and, with the exception of the Great Recession, he’s been able to grow the business year-over-year into the company he leads now.
After the recession, Maldonado and his partner reinvented the company and established a whole other niche. They decided to focus on an underserved market by acquiring profitable small companies of a certain size in the B2B arena, essentially transforming BizGro into a large holding company that is a professional acquirer. It was a smart move, and they began growing exponentially. They also have continued to grow throughout the pandemic, buying companies that were essential and thriving.
Today BizGro Partners is at $240M in annual revenue with 1,200+ employees and a market value upwards of $350M. Maldonado joined Vistage in 2019 because he wanted to be around other entrepreneurs, partner with them and learn from them. He’s now surrounded by positive, forward-thinking people who want to grow, too. His Chair, the diversity of speakers, resources, the group dynamic — all bring value to his thought process.
One thing that’s changed since Maldonado joined Vistage is his mindset about being an entrepreneur. He now approaches it as a lifestyle. New challenges are going to pop up every single day and if you emotionally react you’re going to burn out. You have to allocate your energy properly. There’s a difference between a problem and a disaster. You can’t treat every problem like a disaster; you’ve got to keep things in perspective.
Maldonado had big aspirations when he started out, so he still considers his business to be a work-in-progress. There’s lots of room for growth, but he’s very happy with how far he has come.
Top CEO Tips from JC Moldonado:
- Focus on the solution, not the problem.
- Manage consistent incremental growth, year over year.
- Know that new challenges are going to pop up every day. Embrace them and allocate your energy properly.
Braydan Shaw, 6th Generation Owner of Burns 1876
Braydan Shaw is the 6th generation owner and president of Burns 1876, a 146-year-old western retail and manufacturing company — the longest-running family-owned business in the industry. With all that responsibility comes some unique challenges and Shaw is not about to let anything slip on his watch.
Braydan says his focus is “always on making sure the business will endure many generations into the future. That means we’re committed to slow and steady growth, and refrain from risky decisions.”
Yet, at the same time, he explains, the business has survived and thrived because his predecessors were able to quickly adapt to the changing times. “When the automobile threatened our equine product line back in the 1930s, my great grandfather created and patented a collapsible storage pouch that was attached behind the seat. My grandmother gained momentum in that lane by inventing saddle blanket seat covers.”
In a family business like his, Braydan points out that it’s easy to have blinders on and to continue doing things the way they’ve always been done — which is one of the reasons he joined Vistage.
“Being part of a diverse group of peers has opened my eyes to different practices and perspectives. There’s also all the resources, webinars and speakers that spark great ideas that I take back to my team to implement. But I think what I’ve come to value most is the opportunity to think through any issue that comes up with a whole group of peers who I trust and respect. That aspect alone is worth the price of membership.”
Braydan says he comes from a family who was called by the spirit of West — cowboys who kept moving forward, looking for a better life. “They endured great hardships and never sat on their laurels. They were striving to be better every day and set up the next generation for success. I am, too.”
Braydan’s strategy for running a long-time family-owned business:
- Always stay focused on the long-game — setting future generations up for success.
- Commit to slow and steady growth.
- Refrain from risky decisions.
- Take off your blinders— the way things have always been done— and try on different perspectives.
Caryn G. Mathes, President and General Manager of Puget Sound Public Radio KUOW
As a kid, I aspired to be a print journalist. By age 14, I had a byline in the youth section of our local daily paper. In college, I leveraged that experience into a TV news writing job, which ultimately led to being a weeknight TV anchor at age 19. From there I went into commercial radio; the skills and contacts I gained positioned me for a news director job at an NPR station. I took an opportunity to be general manager at that station and now have been the CEO at three NPR affiliates.
While directing the change and growth of an organization is exciting and fulfilling, it can also be isolating, draining and demoralizing. About a year into my tenure in Seattle, I met a very dynamic female CEO of a mission-driven nonprofit and she piqued my interest about Vistage and even introduced me to her Vistage Chair.
That was in 2015. Since then, my Vistage experience has impacted me tremendously. As members, we are encouraged to work on our businesses and organizations and avoid submersion in them. The support and guidance through Vistage helped me build and nurture fantastic teams leading to the growth and transformation of my organization. In my 7-year tenure we’ve had net growth of 55 new staff members, doubled the annual revenue to $22 million and expanded the reach and impact of our content. I give Vistage credit for helping me stay focused, try new approaches, safeguard my own health and well-being and that of my teams — and avoid discouragement and despair.
But the greatest benefit has been the gift of perspective — the ability to pull back and look at a situation from different angles. When I am in the fray of the day-to-day, I can be consumed. My Vistage meetings provide a safe space where you can say anything, explore any issue and have the full support and counsel of your peers. The meetings give me additional perspective, tools, leadership learnings and experience by proxy that amplify my own. The monthly group gatherings, expert speakers and coaching time with my Vistage Chair allow me to take a deep breath when I’m in the midst of a challenge and look at it with new eyes.
Mathes leads to:
- Enhance KUOW’s relevance and resonance through high-quality, innovative journalism
- Involve the community in setting the editorial agenda
- Rebuild KUOW’s digital, mobile and on-demand modalities to capture new audience and raise KUOW’s value proposition with a changing demographic
- Secure KUOW’s future in the highly disrupted and disintermediated news arena through mature marketing and fundraising practices, and
- Recruit/retain/grow media’s “best and brightest” with an emphasis on racial equity and inclusion
Start living your life of climb
This leadership path has been traveled by 100,000+ top-performing business leaders for more than 60 years. It requires a daily climb, constant rigor and a commitment to growth. But the journey is well worth the effort, for it will bring you to peaks you never thought possible.
These executives have grown their businesses to new levels by prioritizing leadership and strategy. Enhance your own leadership by leveraging their tips and applying their perspectives to your own challenges.