We were lucky to catch up with Taylor Radway recently and have shared our conversation below.

Taylor, thanks for joining us, excited to have you contributing your stories and insights. What was the most important lesson/experience you had in a job that has helped you as a business owner?

One of the most important lessons I learned before becoming a business owner came from one of the most unconventional jobs I’ve ever had: working as a bounty hunter.

Most people think bounty hunting is like what they see in movies—kicking down doors, chasing fugitives, and making arrests. While there were certainly moments like that, the reality was that the majority of the job was surveillance, investigation, tracking, reconnaissance, and managing a constant stream of moving pieces.

At any given time, I could be actively searching for ten or more fugitives. Each one had different leads, different family members, different habits, and different locations they were known to frequent. Success depended on being able to prioritize information, make quick decisions, and stay focused under pressure.

I remember one particular night when we had spent several hours conducting surveillance on a residence where we believed one of our targets was hiding. We had vehicles positioned, people watching multiple exits, and we were preparing to make contact. Right before we moved in, my phone rang. A trusted source told me that another fugitive we had been searching for had just been spotted across town.

At that moment, I had two high-priority opportunities competing for my attention. If I stayed, we might catch the first suspect. If I left, we might capture the second. The wrong decision could mean losing both.

Situations like that happened constantly. You had to quickly assess the quality of the intelligence, evaluate the resources available, delegate responsibilities, and make a decision with incomplete information. There was no time for overthinking. There was no room for panic.

Looking back, that experience prepared me for entrepreneurship better than any business class ever could.

As a business owner, I face similar situations every day. Multiple clients need attention. Employees have questions. Sales opportunities appear unexpectedly. Problems arise that demand immediate action. Everything feels important, and sometimes everything actually is important.

Bounty hunting taught me that success isn’t about doing everything at once. It’s about staying calm, gathering the best information available, prioritizing effectively, and executing decisively. It taught me how to manage multiple high-priority tasks without losing focus on the bigger objective.

Most importantly, it taught me that execution matters more than perfection. The people who succeed in both bounty hunting and business are rarely the ones with perfect information. They’re the ones who can make sound decisions, adapt when circumstances change, and continue moving forward under pressure.

Those lessons have stayed with me throughout my entire career and continue to influence how I lead companies, manage teams, and solve problems today.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’ve never taken the traditional path, and looking back, that’s probably what has shaped me the most.

My career started where a lot of people in the security industry begin: standing at the door of bars and nightclubs. I was a young guy working bar security, learning how to manage conflict, read people, and keep situations from escalating. Most people think security is about being the toughest person in the room, but I quickly learned it’s actually about communication, awareness, and leadership. The best security professionals solve problems before they ever become physical.

From there, I worked my way into security management roles where I oversaw teams, operations, and large venues. I learned how to lead people, manage schedules, handle client relationships, and take responsibility for the safety of hundreds or even thousands of people at a time. Those experiences taught me that leadership isn’t about giving orders—it’s about creating systems, building trust, and setting the standard through your own actions.

As my career progressed, I had the opportunity to work within Apple’s fraud division. That experience exposed me to a completely different side of security. Instead of dealing with physical threats, I was investigating fraud, identifying patterns, gathering intelligence, and protecting both customers and company assets. It sharpened my analytical skills and taught me how to make decisions based on facts, evidence, and attention to detail.

Around the same time, I was also working as a bounty hunter, which remains one of the most unique and challenging experiences of my career. Bounty hunting required a combination of investigation, surveillance, intelligence gathering, tracking, and execution. Every day involved solving problems with incomplete information and adapting to constantly changing circumstances. It taught me how to stay calm under pressure, manage multiple priorities simultaneously, and execute when the stakes were high.

Eventually, I decided to bet on myself and started my first security company.

Like most entrepreneurs, I didn’t have all the answers. What I did have was experience, determination, and a willingness to outwork almost anyone. Over time, I grew that company into an organization with more than 150 employees and over $6 million in annual revenue. We provided security services for clients ranging from entertainment venues and festivals to corporate properties, hotels, private communities, and major brands. More importantly, we built a reputation for professionalism, customer service, and quality execution.

Today, I continue to operate in the security industry as an owner and operator of my second security company, where my team provides professional security services throughout Connecticut and Massachusetts. Our focus is simple: protect people, solve problems, and represent our clients with professionalism. Whether we’re providing event security, property security, executive protection, or security consulting, our goal is to create safe environments while delivering a level of service that exceeds expectations.

At the same time, I’ve built a second passion into a growing business: combat sports media.

Combat sports have been a major part of my life for years. Through my media platforms, podcasts, interviews, and content, I’ve had the opportunity to cover some of the biggest stories, athletes, and events in mixed martial arts, bare-knuckle fighting, boxing, and grappling. What started as a passion project has evolved into a growing media brand that allows me to combine my love for storytelling, business, and combat sports.

If there’s one thing that connects everything I’ve done—from security guard, to fraud investigator, to bounty hunter, to entrepreneur, to media personality—it’s that I’ve always been fascinated by people. Understanding how people think, what motivates them, how they respond under pressure, and how to build meaningful relationships has been the foundation of every success I’ve had.

What sets me apart is that I haven’t learned business from a textbook. I’ve learned it in bars at 2 a.m., on surveillance operations tracking fugitives, inside corporate fraud investigations, managing hundreds of employees, negotiating contracts, building companies, and interviewing world champions. My experience has been earned through real-world execution.

What I’m most proud of isn’t any specific business achievement. It’s the fact that I’ve been able to continuously reinvent myself while staying true to my values. I’ve gone from security guard to company owner, from employee to entrepreneur, and from consumer of media to creator of media. Along the way, I’ve created opportunities not only for myself but for employees, clients, athletes, and partners.

For potential clients, followers, and supporters, the biggest thing I want them to know is that authenticity matters to me. Whether I’m protecting a client’s property, interviewing a fighter, building a business, or creating content, what you see is what you get. I’m a business owner, a father, a combat sports enthusiast, and someone who genuinely believes that hard work, adaptability, and relationships are still the foundation of long-term success.

My story is proof that you don’t have to follow a conventional path to build something meaningful. Sometimes the most valuable experiences come from the roads nobody expects you to take.

Can you tell us about a time you’ve had to pivot?

If there’s one word that has defined my career, it’s pivot.

I actually love that word because I believe the ability to pivot is one of the most important skills an entrepreneur can develop. Business rarely goes according to plan. Markets change, clients change, opportunities appear unexpectedly, and sometimes life forces a decision on you whether you’re ready or not. The people who succeed aren’t always the smartest or the most talented—they’re often the ones who can adapt the fastest.

One of the biggest pivots of my life happened on my birthday.

At the time, I was working as an Operations Manager for a security company. I had invested countless hours into helping grow the business. I was responsible for managing operations, employees, client relationships, scheduling, and putting out fires every day. Like many dedicated employees, I treated the company as if it were my own.

Then, on my birthday, I was fired.

No warning. No backup plan. No roadmap for what came next.

I remember driving home that day with a million thoughts running through my head. I was frustrated, disappointed, and uncertain about what the future looked like. Like most people who suddenly lose a job, I immediately started thinking about what my next move should be.

That night, I called someone whose opinion I respected. I explained the situation and asked a simple question:

“Should I go find another job, or should I start my own company?”

Without hesitation, they said, “Start your own company.”

That conversation changed my life.

The truth is, starting a company wasn’t the safe option. The safe option would have been finding another management position, collecting a paycheck, and moving on. Instead, I decided to take everything I had learned throughout my career—from bar security, security management, fraud investigations, and bounty hunting—and bet on myself.

I didn’t have investors.

I didn’t have a large bank account.

I didn’t have a perfect business plan.

What I had was experience, relationships, and confidence in my ability to solve problems.

So I started my first security company.

Like every entrepreneur, I faced challenges almost immediately. There were long days, sleepless nights, difficult clients, staffing issues, cash flow concerns, and countless moments where things didn’t go according to plan. But there was also something different: every obstacle was now mine to solve.

Looking back, being fired on my birthday was one of the best things that ever happened to me.

At the time, it felt like a setback. In reality, it was a redirection.

That experience reinforced a lesson I still carry with me today: sometimes the biggest opportunities arrive disguised as disappointments.

As entrepreneurs, we often talk about growth, success, and achievement, but those things are usually preceded by uncertainty. The ability to pivot isn’t just about changing direction when things go wrong. It’s about recognizing opportunity when life unexpectedly changes your path.

Since then, I’ve built companies, led teams, worked with incredible clients, and created opportunities that never would have existed had I simply looked for another job.

Whenever I face a challenge today, I remind myself of that birthday. What felt like the end of something was actually the beginning.

That’s why I believe successful business owners don’t just survive uncertainty—they learn to thrive in it. Because every pivot creates the possibility for a new outcome, and sometimes that outcome ends up being far better than the one you originally planned.

Any advice for growing your clientele? What’s been most effective for you?

People often expect there to be some secret marketing tactic, sales script, or growth hack behind building a successful business. In my experience, the most effective strategy for growing my clientele has been much simpler: respond quickly, do what you say you’re going to do, and genuinely care about helping people.

It sounds simple because it is simple—but it’s also surprisingly rare.

Over the years, I’ve learned that most clients aren’t just buying a product or service. They’re buying trust. They want to know that when they call, someone will answer. When they have a problem, someone will help solve it. When a commitment is made, it will be honored.

One of the habits that has helped me grow every business I’ve been involved with is responding quickly. Whether it’s a phone call, text message, email, or social media inquiry, I try to get back to people as fast as possible. In today’s world, speed matters. Most business owners know how frustrating it is when you’re trying to hire someone and don’t hear back for days. I’ve won countless clients simply because I was the first person to answer the phone and provide a solution.

Beyond responsiveness, I’ve always believed your word is your most valuable asset.

If I tell a client I’m going to call them back, I call them back. If I tell them a proposal will be delivered by Friday, it’s delivered by Friday. If I commit to solving a problem, I follow through. Business is built on trust, and trust is built through consistency. Every promise you keep creates confidence. Every promise you break creates doubt.

Another strategy that has been incredibly effective is staying in touch with clients even when I’m not trying to sell them something.

Many business owners only contact clients when they want business. I’ve always taken a different approach. I’ll check in to see how things are going. I’ll ask how their family is doing. I’ll send them an article that may help them. I’ll connect them with someone in my network if I think it could benefit them. Sometimes the conversation has nothing to do with the services I provide.

I’ve found that when people know you genuinely care about their success, the relationship becomes much stronger than a typical business transaction.

The reality is that clients have options. In most industries, there are dozens of companies offering similar services. What often separates one company from another is the relationship. People want to work with people they trust, people who communicate well, and people who make their lives easier.

Throughout my career, whether in security, consulting, marketing, or media, I’ve tried to operate from a simple philosophy: find ways to be valuable before you ask for anything in return.

If you consistently answer the phone, keep your word, follow through on your commitments, and show people that you’re there to help, your clients become more than clients. They become long-term relationships, referral partners, and advocates for your business.

Looking back, some of my biggest opportunities didn’t come from advertising or marketing campaigns. They came from people telling others, “If you need help, call Taylor. He’ll take care of you.”

That’s still the most powerful form of growth there is.

Contact Info:

• Website: https://www.TheRadwayGroup.com
• Instagram: @TaylorRadway
• Facebook: https://www.facebook.com/taylor.radway.9/
• Linkedin: https://www.linkedin.com/in/aylorradway/
• Youtube: @CombatMayhem

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