When I look back at my career, I see two very different worlds that, in their own way, shaped the investor and entrepreneur I’ve become. The first was digital commerce — a space that demanded speed, experimentation, and adaptability. The second is structured capital and private credit — an environment that rewards patience, discipline, and long-term thinking.
At first glance, these two worlds couldn’t be further apart. One thrives on constant change, the other on stability. But in reality, the lessons I learned in digital commerce continue to inform how I approach investing today.
The Digital Commerce Years
My early years in business were deeply tied to e-commerce. It was a time of rapid growth, when new technologies were opening doors for entrepreneurs at an unprecedented pace. Starting and scaling businesses online gave me invaluable exposure to opportunity — but also to risk.
In digital commerce, you move fast because the market demands it. Consumer behavior shifts quickly, and companies that fail to adapt disappear. That environment forced me to learn agility. It taught me how to spot trends early, how to test ideas before committing fully, and how to embrace failure as a teacher rather than a final verdict.
But while e-commerce offered incredible upside, it also revealed its weaknesses. Growth often came at the expense of stability. Cash flow could be unpredictable, margins were tight, and a single change in platform rules or consumer preferences could wipe out months of progress.
Those realities made me realize something fundamental: speed is powerful, but it cannot be the foundation of everything.
Transitioning to Structured Capital
As I matured as an entrepreneur, I began searching for a framework that emphasized resilience over momentum. That search led me to structured capital and private credit.
Unlike the fast-moving world of e-commerce, private credit is about predictability. It is rooted in cash flow, collateral, and long-term agreements. Every deal is structured to balance risk and reward. There is no illusion of overnight success; instead, the goal is steady, contractual returns that investors and borrowers can both rely on.
What drew me to this world was not just the stability it offered, but the clarity. In private credit, terms are transparent, incentives are aligned, and success comes from discipline rather than speculation. It was a stark contrast to the volatility of digital commerce, but it felt like the natural next step in my journey.
The Lessons That Carried Over
Although I shifted industries, I didn’t leave my e-commerce experience behind. In fact, the lessons I learned there continue to shape how I think about capital today.
- Agility matters, even in structured environments. Markets change, and while private credit is less volatile, it is not immune to shifts. My background in adapting quickly allows me to anticipate change and adjust frameworks before it’s too late.
- Data is only valuable when paired with judgment. In digital commerce, analytics were everything. But numbers without context often mislead. Today, I still rely on data, but I filter it through a framework of discipline and fundamentals.
- Growth without resilience is a trap. I’ve seen businesses collapse because they chased expansion at all costs. That experience fuels my commitment to investing in structures that are sustainable over the long run.
These are the threads that connect two seemingly opposite careers. What I once thought of as a chaotic training ground has become a foundation for clarity.
Building for the Long Term
The greatest difference between the two worlds is time. E-commerce often rewards what happens this quarter. Structured capital rewards what happens over decades.
For me, that shift has been transformative. It’s not about abandoning ambition, but about channeling it differently. Instead of asking, “How fast can this grow?” I now ask, “How long can this last?”
That mindset has influenced every part of my professional life. It affects how I lead teams, how I design strategies, and how I evaluate opportunities. It’s also why I believe private credit is one of the most important tools for investors today — it offers a way to generate stable income while avoiding the rollercoaster of public markets.
If you’d like to explore this topic further, I’ve written on long-term wealth building through structured capital where I explain why I moved away from traditional models.
Conclusion
Shifting from digital commerce to structured capital was more than a career move — it was an evolution of philosophy. One world taught me speed, the other taught me discipline. Together, they shaped a balanced approach to investing: agile when necessary, patient when it matters, and always focused on sustainability.
In a business culture that often celebrates the quick win, I’ve learned that the real victories are the ones that endure.
Stuart Simonsen
Stuart Simonsen
