How These CEOs are Living a Life of Climb

CEO tips for 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.

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.


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Category: Leadership


About the Author: Vistage Staff

Vistage facilitates confidential peer advisory groups for CEOs and other senior leaders, focusing on solving challenges, accelerating growth and improving business performance. Over 2…

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