What made you want to do the work you do? Please share the full story.

Wealth transfer planning involves a really interesting combination of finance, family, and legacy building. When I worked in a family office environment, I saw how the ultra-wealthy approach these challenges differently. They have access to strategies and best practices that many successful people are unaware of.

I realized there was a huge gap. You have families worth $15-50 million who are incredibly successful but don’t have access to the same level of sophisticated planning that families worth $100 million or more do. I started Catalyst Advisory to bring those family office best practices to a broader group of high-net-worth families who deserve that level of service and strategy.

Tell us 3 surprisingly easy and 3 surprisingly difficult things about your business.

Surprisingly easy:

1. Getting results for clients – When we have the right client in the right situation, the results can be absolutely incredible. This might involve saving families millions in estate taxes or creating liquidity strategies that preserve generational wealth. Making sure we’re working with the right clients is the important part. When that happens, the results will come.

2. Explaining the benefits or value of my services – When I’m talking to the right person or family, showing the value is straightforward. When you can demonstrate how proper planning might save someone millions in estate taxes or show a business owner how they can protect their business, the benefits are clear.

3. Maintaining work-life balance – I have three active sons, and our family’s schedule is busy. Having those family commitments actually makes it easier to set boundaries around my working hours.

Surprisingly difficult:

1. Wearing multiple hats – As a mostly solo operation, everything falls on me. It’s a constant challenge, especially when it involves things that are outside my areas of expertise.

2. Coordinating with multiple advisors – Getting attorneys, CPAs, wealth managers, and family members aligned takes some effort because of all the moving parts.

3. Managing the emotional side of planning – These conversations involve mortality, family dynamics, and other sensitive issues.

What are the 3 things you like best about your work and why?

1. The strategy sessions – I love sitting down with successful families and mapping out solutions to complex problems. Every situation is unique.

2. Bringing clarity to confusion – The life insurance and estate planning world can be complex, and I genuinely enjoy cutting through all the jargon to help people understand their options and make informed decisions.

3. The generational impact – When we get the planning right, we’re not just helping one person or even one generation. We’re creating structures that can benefit families for generations to come. That’s incredibly meaningful work.

What are your greatest 3 skills and how have they helped you succeed?

1. Relationship building – Whether it’s with clients, other advisors, or strategic partners, this business is built on trust and collaboration. My ability to build genuine relationships has been crucial.

2. Simplifying complexity – I have to be able to explain strategies in terms that clients can understand and feel confident about.

3. Finding solutions – I genuinely enjoy the puzzle-solving aspect of this work. Every family’s situation is unique and being able to find solutions is critical.

Tell us about a time where you saw a surprising outcome that you did not expect.

The most surprising outcome was actually when my previous employer had to suddenly close its doors. I had been telling my wife for a couple of years that I wanted to eventually start my own firm, but I didn’t think I was quite ready yet. She encouraged me to start building my credentials to add to my experience.

When the company closed, it forced me into a decision I thought I’d make in a few more years. But it turned out to be exactly what I needed. Starting Catalyst has allowed me to serve clients the way I always envisioned, and the timing ended up being perfect, even though it required a leap of faith. I’m grateful for my wife’s support along the way.

What is the biggest challenge you face each day and how do you handle it?

The biggest challenge is being responsible for every aspect of the business. At my previous employer, I could focus purely on client work and strategy. I didn’t have to think about marketing, maintaining the website, managing business finances, or handling administrative tasks. Now, I’m the CEO, CFO, head of marketing, and lead advisor all rolled into one.

I handle this by being very intentional about time blocking and prioritizing client-facing work during my peak energy hours. I also batch similar tasks together. And if there’s something I can’t handle on my own, or it’s not the best use of my time, I’ll hire a contractor.

What do you value most and why?

Faith and family. My faith provides the foundation for how I approach business and relationships. And my family keeps everything in perspective. These values also influence how I work with clients and my motivation for helping families build legacies that align with their values.

What achievement are you the proudest of and why?

Raising my three sons. Building a successful business is rewarding, but watching my boys grow into young men of character is what I’m most proud of. I’m already having conversations with my oldest about entrepreneurship and business ownership, and seeing his interest in what I do gives me hope that we might be building something generational ourselves. Everything else I do professionally is ultimately in service of being the best father and role model I can be for them.

What is your favorite movie and why?

I Can Only Imagine. It is such a beautiful story of redemption and forgiveness. It’s the kind of movie I can watch with all of my kids and they enjoy it and understand the message. Plus the music is really good!

What advice would you give to your younger self and why?

Don’t wait until you feel 100% ready to make big moves. I spent too much time thinking I needed more credentials, more experience, or the perfect timing before starting my own firm. The truth is, you’re never going to feel completely ready for the next level. There’s always going to be something else you think you should learn or accomplish first.

I was telling my wife for years that I wanted to start my own business “someday,” but I kept finding reasons to wait. When my previous employer closed and forced my hand, I realized I had been more ready than I thought. Sometimes you have to bet on yourself before you feel fully prepared.

Who has been your biggest mentor in life (personal or professional) and how have they helped you?

My father has been my biggest mentor, though he probably doesn’t even realize it. He set an incredible example for work ethic, integrity, and always doing things the right way, even when no one was watching. Growing up, I watched him approach every job and responsibility with the same level of commitment and honesty, whether it was big or small.

He taught me that your reputation is everything and that shortcuts might save you time in the moment, but they’ll cost you credibility in the long run. Those lessons have been fundamental to how I approach client relationships and business decisions. In a field like wealth transfer planning, where trust is everything, the foundation he gave me about character and integrity has been invaluable. He showed me that success isn’t just about what you accomplish, but how you accomplish it.

Just for fun, what is your favorite food?

There are a lot of potential answers here, but I’ll go with a nice steak. We also eat a lot of Italian food in our house, and Thai is always a great option for takeout.

Connect With Steven Bowles: