Become The Bank
Before we earned our first dollar, we owed over a million.
Built on Debt
Hudson Far West was built on debt—over $2 million of it: mostly auto financing, term loans, and credit cards. All of it was paid back. That risk built the business—and nearly broke it, too.
To be clear, we couldn’t have started without certain financial institutions. I don’t think some of those early finance companies—even though they were eventually paid off profitably—fully understood the risk they were taking with our company.
Back then, for example, financial reps at car dealerships, along with their underwriting counterparts, were playing an origination game: more loans, more fees. We were getting so many approvals that I even checked in with a loan officer at one of the dealerships we were working with to make sure nothing was broken—that our application wasn’t omitting anything or unintentionally misleading.
This business was built on debt—and on my ability to access it, manage it, and ultimately outgrow it.
I can take risks—big ones, too—but I’m actually quite financially conservative in many ways. I started my career in debt restructuring. Launching a small, luxury “rideshare” rental business focused on Uber and Lyft drivers in NYC was a risky proposition—especially in an industry I had no background in. I wasn’t an operator; I began my career as an investment banker and later became an investment professional. I had never run a business.
It also wasn’t the kind of business venture capitalists were going to fund: a one-man team, capital-intensive, with depreciating assets—none of it screamed VC-friendly. Honestly, one reason I chose the idea was because it didn’t require VC funding.
While Uber and Lyft were new companies, the concept of leasing vehicles to New York City for-hire vehicle (FHV) or taxi drivers dates back over a century. Uber was an old idea, reimagined—and it sparked an ecosystem where other old (and new) businesses could be reinvented. Our leasing model, though traditional in many ways, was undoubtedly born of Uber—driven by its genuine disruption of incumbent players and NYC’s unique regulatory environment.
We Pivoted, We Survived
Being a “finance person,” of course I built out cash flow and IRR models. I laid out ‘upside’, ‘base’, and ‘downside’ cases. We launched in 2016 and scaled up in the years that followed. The business relied on debt, cash flow, and the assumption of healthy Uber, Lyft, and FHV trip demand in NYC.
COVID was beyond any downside imaginable. Even if I had modeled a hypothetical ‘crash’ case scenario, it wouldn’t have captured the devastation the pandemic dealt our business. But that’s not how the world, or life, works.
Long story short: we survived, pivoted, pivoted again, and survived. Today, the business no longer relies on debt to grow and has expanded beyond our own fleet operations (more on that another day).
During those difficult pandemic days that felt like weeks, weeks that felt like months, and months that felt like decades—when a generational crisis hit—some banks were kind, and some were not. What was my takeaway?
My assumption now is that most bankers—and, for that matter, most outside investors—won’t be there for you when you need them. In fact, at the exact moment you need them most, they’ll cut you off—along with your credit line.
To be clear: most, not all.
Debt is a Tool, It’s Also a Weight
Some people can handle a lot of debt. I did—for a while. But when I began paying it off, I physically felt lighter.
Equity can feel like debt too—especially when it comes from investors you rely on for repeated capital injections. I’ve learned that I don’t want to run a business that requires a lot of debt—or work with non-strategic investors, particularly those I can’t operationally partner with (i.e., purely financial backers).
So, if you’re like me—and know you don’t have a high tolerance for relying on banks or outside capital—how do you create and grow a business?
If I knew then what I know now (an impossible thing), I would’ve pursued a business that didn’t require much debt or external funding—something I could “bootstrap”. It’s slower, more painful, and the scarcity of capital forces you to think carefully about every decision. But it teaches you in a way no teacher or classroom ever could. Today, cheap software and AI tools make that path more viable—and your thesis easier to prove.
Leverage is a powerful tool—but freedom from it is even more powerful. Become your own bank.
Final Note
It’s not lost on me that some businesses require outside capital. If you’re building a real estate portfolio, it makes sense to take on mortgages. Unlike a vehicle fleet, real estate tends to appreciate—but you still have to run the numbers.
At scale, debt or equity financing can become a competitive advantage—especially in real estate, manufacturing, or breakthrough tech. And if you're running a finance or insurance company, debt isn’t optional—it’s fundamental.
Finally, if debt is very cheap, it might also make sense to use it to enhance returns without significantly increasing risk to your business.
The above reflects my experience—it isn’t universally applicable to all businesses or circumstances.