Why I Invest the Way I Do

In the fall of 2008, I was splitting my time between the classroom and the trading desk. I was in the middle of my MBA, and I was also working with my stepdad, who had been in the fixed income markets since 1979. We were managing money for retail clients, primarily through individual bonds and preferred securities, and when the financial system collapsed, we weren't analyzing it from a distance. We were holding the very positions that were unraveling in real time.

Fannie and Freddie preferreds, which we owned, went to zero, and several large European banks suspended their preferred dividends entirely, adding to the sense that even senior securities weren't immune. We were on conference calls late into the night with analysts, bank reps, and sometimes regulators, working to understand the scope of the damage, how the situation was evolving, and what might come next. These weren't abstract losses or theoretical risk models. These were preferred securities purchased at $25 that were now trading at $6. What had started as a methodical, long-term strategy turned into something much different. We were now modeling scenarios, evaluating credit structures, and repricing risk in real time. Clients who had trusted us with their savings were watching their account values drop, and we stayed focused on the work of assessing risk to be best positioned for whatever was coming next.

The Lost Art of Due Diligence

After the worst of the crisis passed, we went back to what we always did, building portfolios security by security, looking for income that could hold up across market cycles. Every day started by reading and evaluating current economic data, reviewing trades from the prior day, and then moved to the terminal, scanning for individual positions that showed up on our screeners. Some were familiar names we had already done the work on and were waiting to buy at the right price. Others were new and required a fresh round of due diligence to understand both the issuer and the structure of the specific offering.

Our due diligence process involved listening to analyst calls, reviewing company earnings, reading 10-Ks, and in some cases, having direct conversations with management. If the issuer was local, we might drive by the facility ourselves. On smaller issues, especially municipals or attractive tax-exempt offerings, we sometimes had access to the executive team, which helped us get beyond what the prospectus said.

Of the non-traditional due diligence we did, one example that stands out was a student housing project issued through a private activity bond structure. These are tax-free bonds tied to public-private partnerships, and while they offer some yield pickup, they also come with added risk. In this case, it was a university apartment complex, and I wanted to know more than what the financials said. I called the office, spoke with the receptionist, asked about vacancy rates, and whether there was a waitlist. I looked at enrollment trends for the university, studied the surrounding rental market, checked online reviews, and tried to get a sense of the bigger picture.

On paper, the yield looked attractive, and the bond had some backing from both the university and the state. But after all the work, we passed. A few years later, the project failed, the apartments shut down, and bondholders dealt with missed payments and steep price losses. That decision to pass didn't show up in any performance report, but it saved our clients from unnecessary risk and hassle.

This is why terms like high-quality, reliable income matter. We're not chasing yield. We're building portfolios that hold up, and sometimes that means passing on something that looks good upfront but doesn't deliver when it counts.

How Experience Shapes My Investment Approach

That experience, working in the fixed income world, shaped how I operate to this day. I still read an enormous amount compared to most in the planning profession. It's just a habit. I continue to evaluate every position with nearly the same level of discipline I used on the bond desk. This deliberate approach often leads me to move slower than others who manage money, but it has helped me avoid making emotional or reactionary decisions during volatile periods. It served me well through the financial crisis and again during COVID. While I've evolved professionally and expanded the tools I use, that foundation has not changed.

When clients ask about my investment strategy, philosophy, or request a formal investment policy statement, what they're really asking is, "How do you operate, and why?" For me, the answer comes from experience. I started in fixed income, building portfolios one position at a time, learning how to evaluate risk, read structures, and generate reliable income. Over time, that evolved into financial planning, thinking in terms of cash flow, goals, taxes, and long-term tradeoffs. In recent years, I've added a third lens through financial therapy, helping clients make better decisions by understanding the emotional and behavioral drivers behind money.

This combination of technical training, mentoring, and lived experience shapes how I operate today. While parts of my approach may appear qualitative or relationship-focused on the surface, the core of my asset management work is rooted in everything I've learned through that evolution. It's not theoretical. It's built from years of doing the work, asking better questions, and staying focused on what holds up.

Jonathan Kolmetz is a Licensed Professional Counselor, Financial Advisor, and President of Oaks Wealth Management. He holds an MBA, a Master’s in Clinical Mental Health Counseling, and is passionate about helping families rewrite their money stories.