As an entrepreneur, being right once is hard. But if you can do it three times, achieving financial independence is easy.

The First: Building a Profitable Business

I started this journey in 2017 from my parents' basement. At the time, I was one year away from retiring as a professional basketball player overseas. I didn’t make much money, so I had no savings and no technical ability to develop an app. Given my situation, I knew the only way for me to build a profitable business was to create a service business.

This business ended up being International Sport Recruitment (ISR).

Before landing a pro contract in 2013 in the British Basketball League, I first had to put myself in the vicinity of this opportunity. I did this by securing a full international postgraduate scholarship to the University of East London.

It took almost two months of surfing the internet late into the night to find this needle in the haystack.

From that experience, I knew immediately I could make a business from it because there were thousands of other student athletes from the US like myself who wanted to extend their career however possible.

I represented myself as an agent and my basketball career took all of my attention for the next four years, so the business idea I had in 2013 didn’t launch until January 2017.

The business model was simple. Universities in the UK had a KPI to increase their international student population, and the sports teams wanted to improve their standings by recruiting US student-athletes in certain sports.

My only job was to play matchmaker between student-athletes and UK universities.

I received a commission between $2,000 and $2,500 for every student-athlete I successfully recruited.

The downside to this business was that payment was not released until students were enrolled and on campus for one to two months.

When I received that first payment of over 10,000 GBP from the University of East London, it felt like six figures.

In total, I ended up making over six figures with ISR. But just as I figured out how to scale to six figures annually and eventually seven figures by utilizing an app to streamline the recruitment process, Covid happened.

That was me being right the first time.

The Second: Building a Six-Figure Cash Flowing Business

Although I made over six figures in total with the first business, building a cash-flowing business that makes six figures per year is the next level.

This business was called Virtual Attention (VA) and it was started from a villa in Bali.

VA was a virtual assistant business to help business owners delegate without having to communicate directly with virtual assistants.

One of the big differences between ISR and VA was that with VA, I had a co-founder (my girlfriend), which meant everything moved much faster.

Our first client was the founder of Barefoot Wines, which was cool because that’s the wine I used to drink in college.

The first year we did $93,000 in revenue, which was just shy of our ambitious first-year goal of $100,000. The second year we reached $133,000 in only the first seven months before shutting down due to our first daughter being born prematurely.

The first time with ISR, I had an app built which we never used due to Covid. Then the second time, we built a Shopify app and a three-user login app, which we never finished.

Both of these experiences provided the knowledge to understand what works and what doesn’t, and how to actually scale a business.

With VA, we clearly proved we could consistently generate six figures. This is the biggest milestone to unlock the ability to build something that can lead to financial independence.

However, the last piece that needed to be solved was how to build a system and technology that could scale to seven figures and beyond.

The Shift in Mindset

Reaching seven or eight figures involves a shift in mindset. Instead of focusing on survival, you focus on growth and optimization. You start targeting larger markets, investing in scalable systems, and leveraging the power of delegation. It’s about multiplying your efforts and creating a business model that can handle exponential growth.

The Third: Swing For The Fences

In baseball, the home run hitters steal the headlines. But it is also common for the players who hit the most home runs to also lead in the number of strikeouts.

I am currently in the midst of trying to be right for the third time.

Before starting on this current path, I went down the rabbit hole of venture capital.

After shutting down VA, I was looking for a way to expedite the process the third time around and from venture capital I landed on accelerators.

In 2021, I started NGHBR, a professional network for digital nomads.

In 2022, NGHBR was accepted into Techstars, which is the second most popular accelerator behind Y Combinator.

The initial investment from Techstars is $120,000 for 6%, including $20,000 in cash and an optional $100,000 convertible note. They then have the right to follow on if you raise a round of venture capital.

Being in Techstars accelerated the shift in mindset.

Once I went through the program, I quickly realized we could revive VA to make it venture scale.

We rebranded Virtual Attention to Vyrtual and built a task management platform that embedded the original service business on the platform.

In 2023, Vyrtual was also accepted into Techstars.

With NGHBR, I went through as the Chief Executive Officer without much of a team. With Vyrtual, I was the Chief Product Officer alongside a growing team.

For me, this third time has shifted from the idea of having one at-bat to hit a home run to obtaining as many at-bats as possible. I’ve taken on the mindset that within the third time, I can swing as many times as my resources allow and I only have to be right once.

The biggest difference between the first, second, and third times is that both the floor and ceiling are exponentially higher.

Hitting a home run this third time is my singular focus.

The $5M Home Run

For me, the home run means hitting the magic number of $5M liquid. Why $5M? Because with a simple investment approach, it is straightforward to yield a 10% annual return or $500,000 per year. That’s a comfortable income that allows for a lifestyle of freedom and choice—financial independence.