I'm Rob. I've spent my career moving between worlds that don't always talk to each other - investment banking, private equity, venture-backed startups, and now AI in finance. That range of experience is what drives most of what I write here.
I started on the deal side, working in bulge-bracket investment banking and middle-market private equity, where I learned how capital really moves and what makes businesses worth buying (or not). After graduate school at Harvard Business School, I co-founded Exporta Technologies, a VC-backed B2B supply chain tech company that I scaled to an eight-figure run rate before exiting. Building a company from scratch taught me more about business than any deal I ever worked on.
Today I run Caserta Training, where I'm building the next generation of financial modeling and professional development training - with AI baked into the curriculum, not bolted on as an afterthought. I also manage Monaco Venture Partners, an investment firm with five portfolio companies under management. Beyond that, I coach business professionals and consult independently across finance, strategy, and operations.
Patterns of Choices reflects the best thinking I've encountered over the years, and that thinking has always happened at intersections - where finance meets technology, where strategy meets personal discipline, where macro trends meet individual decisions. In corporate strategy, outcomes are rarely the result of a single bold move. They're the culmination of a pattern of choices - hundreds of small decisions that compound over time into something that looks inevitable in hindsight. The same is true in our personal lives. Our daily habits, the way we allocate our time and energy, the risks we take or avoid - these are all patterns of choices that quietly shape where we end up. I want to break down those patterns.
Outside of work, I'm based in Austin, TX. I follow the real estate markets closely - I know the neighborhoods and where the value is hiding. I've helped friends navigate the home buying process, identify investment properties, and walk away with solid returns. I stay on a rotation of group fitness classes and get plenty of help from my goldendoodle. If you want to talk deals, startups, or markets - I'm always up for it.