At 25 years old, after completing my master’s degree at Fordham University and chasing my dream of becoming a professional soccer player, I took a corporate job with Frito-Lay. I spent my 9-to-5 working there and my afternoons/weekends building DIG. I spent five years doing that and I was comfortable. My corporate job made me feel empty because I was selling a product that doesn’t help society but I countered that with the feeling I got from helping kids with DIG.
I didn’t make enough money to make big investment moves but I did make enough to pay the bills and put some money in my 401k. With rising costs in Connecticut, future positions at Frito Lay being only small salary increases and the fact that I didn’t fit in with corporate society, I saw the writing on the wall.
At 30 years old, my friend Nick in Hartford said to me, “Imagine what you could do with DIG if you could take M-F meetings without worrying about your corporate job.” For some reason, I had never thought about it that way. Nick was an entrepreneur and I didn’t know many entrepreneurs so his perspective really hit me when we spoke. I realized it was not only DIG that could thrive, but I could also get into real estate and other projects.
I knew I had some income with DIG so I made the jump. I gave my boss at Frito Lay two months to replace me. He pushed me hard to stay, even telling around thirty people in a regional meeting that entrepreneurs are usually unsuccessful and that I should call him when I need bread and milk. Being the competitor that I am, I wrote down what he said and I have looked at it hundreds of times since then.
The first year of full-time entrepreneurship was tough. I said yes to every coaching opportunity that came my way, even when it meant losing money. By the end of that year, I sat down with my accountant and close friend, Cecil, who took a hard look at my finances and told me bluntly, “You either need to start making real money or go back to your corporate job.” That conversation was a wake-up call. I had to be more strategic and disciplined in my decisions, so I started saying no to opportunities that weren’t aligned with my long-term goals.
By year two, I started to stabilize, and DIG was more on solid footing. I began thinking about diversifying my income, which led me to real estate. I was determined to make sure I wasn’t 100% reliant on DIG. I was finally able to secure a mortgage because lenders wanted at least two years of consistent income from small business owners.
Over the next three years, I bought six multifamily properties in central Connecticut, stretching from Shelton to Vernon, along Route 8 and I-84. I saw that stretch as an area with underpriced properties compared to their rental potential. While appreciation was a nice bonus, my focus was always on cash flow. I evaluated each deal based on the PITI (Principal, Interest, Taxes, Insurance) compared to the rental income I believed I could generate.
Doing real estate projects and DIG at the same time was an entirely different level of work. Keeping remodelling projects moving on schedule, managing tenants and other parts of this work was way more demanding than I anticipated. I learned that rental properties are different from DIG in terms of work commitment. DIG is consistent, manageable work while real estate is a ton of work in the beginning and then not much work once everything is set.
Today, after covering PITI on all my properties, I’m generating great income each month in cash flow. This not only comfortably covers repairs and other unforeseen costs but also provides the diversification that I sought.
Now, my focus is on building systems to improve efficiency and minimize risk across my ventures. Once I’ve solidified those systems, I’ll be ready to take on the next challenge with the same passion and determination that got me here.