How Steven Bowles Turned Deep Expertise Into a Thriving Solo Business

Steven Bowles spent seven years learning how the ultra-wealthy protect and transfer billions. Working inside a family office advisory group, he saw the sophisticated strategies that families with $100 million+ used to preserve generational wealth. But he also noticed that successful entrepreneurs and business owners worth $15-50 million had no access to these same strategies.

Most advisors either focused on the ultra-wealthy or pushed generic solutions. Steven saw an opportunity and was interested in going out on his own, but he was hesitant to make the leap. Then his employer suddenly closed. The decision he thought was still years away became immediate.

In fall 2022, he launched Catalyst Advisory. Within months, he was generating revenue. Today, he works with entrepreneurs, real estate investors, and business owners, bringing family office-level planning to people with illiquid assets.

This is his story of turning deep expertise and strategic relationships into a profitable solo business, and why waiting until you feel "ready" is often the biggest mistake.

How do you explain what Catalyst Advisory does in simple terms?

We help successful families and business owners protect what they've built and transfer it efficiently to the next generation. Most of our clients have built substantial wealth through their businesses or real estate, but they don't need a full family office. We give them access to the same sophisticated planning tools that ultra-wealthy families use, things like advanced estate planning, asset protection, and strategic use of life insurance, without the overhead of a traditional family office.

What led you to start Catalyst Advisory?

I spent seven years in a family office watching ultra-high-net-worth families implement strategies to preserve and transfer wealth. But I kept seeing this huge gap. Families worth $15-50 million, incredibly successful people, couldn't access this level of planning because they weren't quite wealthy enough for traditional family offices, and they'd built their wealth in businesses and real estate rather than liquid assets that private banks want to manage.

The final push was when my employer suddenly closed. I'd been thinking about going out on my own for a few years, but I kept finding reasons to wait. When the company shut down, it forced my hand. Looking back, the timing was perfect even though it didn't feel that way in the moment.

How did you know you were ready to launch your own business?

Honestly? I didn't feel ready. I kept thinking I needed more credentials, one more year of experience, the perfect timing. The truth is, you're never going to feel 100% ready.

What I did have was seven years of deep experience, my Chartered Life Underwriter (CLU®) designation, strong relationships with attorneys and CPAs who knew my work, and clients who trusted me. When the opportunity came, I had to bet on myself even though I didn't feel fully prepared.

How did you land your initial clients?

My first clients came through the professional network I'd built over seven years. Estate planning attorneys, CPAs, and wealth advisors I'd worked with started referring clients who needed exactly what I offered. That existing credibility was crucial because I wasn't starting completely from scratch.

The other big source was client referrals. When you solve a complex estate tax problem or help structure a business succession plan, those clients know other people facing similar challenges.

What was hardest about the first year?

Wearing every single hat. At the family office, I could focus purely on client strategy and relationships. Marketing, operations, compliance, and technology weren’t my responsibility.

Suddenly, I'm doing everything all at once. I've since learned to outsource the things that aren't my core expertise. But that first year, I was doing everything myself and learning the hard way what I should delegate.

What does being "independent" mean for your business model?

It means I'm not tied to any insurance company or product provider. I can access the entire market and recommend what's truly best for each client's situation, not what generates the highest commission for me.

Most advisors in this space are captive to specific carriers or product lines. They might have three or four insurance companies they can work with. I can work with dozens. When a client needs a specific type of policy or strategy, I'm finding the absolute best solution rather than trying to fit them into whatever my employer happens to sell.

Clients feel that difference immediately. There's no hidden agenda. If I recommend something, it's because it's the right answer for their specific situation.

How do you build trust with new clients?

Trust in this business comes from competence, consistency, and genuine care for outcomes.

First, I demonstrate competence by actually understanding their situation. Too many advisors pitch solutions before they've fully understood the problem. I spend a lot of time in discovery reviewing their existing estate documents, understanding their business structure, and talking with their other advisors. When I finally make recommendations, clients know I've done the work.

Second, I'm consistent in what I say and do. If I promise to coordinate with their attorney, I do it. Basic stuff, but it builds confidence over time.

Third, I'm willing to say "no." Not every opportunity is a good fit, and I tell people when something isn't right for them. That kind of honesty builds trust faster than any sales pitch.

Which marketing channels have worked for you?

Strategic networking has been my primary channel, but it's very intentional networking, not just showing up at chamber of commerce mixers. I build real relationships with estate planning attorneys, CPAs, and wealth management advisors who see clients with problems I can solve.

This business is built on trust and referrals, which means playing the long game with relationships.

How do you structure your week as a solo operator?

I'm very intentional about time blocking. Client-facing work like strategy sessions, discovery meetings, and coordination calls with other advisors happen during my peak energy hours, typically mornings. That's when I'm sharpest, and clients deserve my best thinking.

Administrative work, email, and operational tasks get batched into specific afternoon blocks. I'll dedicate specific afternoons to that kind of work rather than letting it interrupt my entire day.

I also protect time for deep work on complex planning cases. Some strategies require hours of uninterrupted thinking. I block those sessions and treat them like client appointments.

Family time is also non-negotiable. I have three active sons, and that actually helps create structure. When you know you need to be at a baseball game at 6 pm, you work more efficiently during the day.

What part of running the business surprised you most?

I genuinely enjoy the strategy work even more than I did at the family office. When it's your business and your reputation on the line, there's a different level of investment in getting things right.

Also, how quickly the right clients find you when you're clear about what you do and who you serve.