At the end of May I spent three nights at a lake house in New Hampshire on a business retreat with three of what will be my co-founders in a new business venture—three people with which, if I’m being completely honest, I am fortunate to even have a seat at the table.
We had three primary goals for this trip:
To determine if we could see ourselves really pursuing this together
To determine what and who would be needed to achieve it and how and when it could be
To determine whether we were each “all in” with a monetary and time commitment
And in between all our big-picture concepting and whiteboard brainstorming, we’d swim, paddleboard, kayak, play horseshoes and cornhole, and cook fresh food throughout the day.
(That bonding time also helped us determine Goal #1.)
As I looked around the table, I was so excited to be there—being a part of the birth of something I never thought I would be, but always secretly wanted to be.
I struggle to consider myself an entrepreneur, even though I have multiple streams of revenue (including a public speaking career, writing, a video production company, real estate investments, physical and digital products, and providing coaching/consulting services).
I consider myself to be a hustler. Not the swindly type, but the work-hard type.
For me, a real entrepreneur is someone who sets out to create a business to fulfill a purpose, scales it, and (potentially) sells it. For me, someone like the founder of a tech startup is a real entrepreneur. And for some reason, despite all my achievements, those are the people I feel most insecure around.
I have many friends in the space. And when I hear them using language I don’t fully understand and talking about investors and Q3s and KPIs and MVPs, I turn into that shy 5-yr-old kid again, scared to speak up or ask a dumb question.
This new business gave me a chance to be a “real” entrepreneur. Of a tech startup, even!
So yes, I was indeed excited. But just as quickly as I became excited, a wave of worry, fear, and regret washed over me.
It was all becoming real that day. And that meant how it impacted my life was real, too.
I had braced for some impact. But there was one was I was not prepared for.
Many people might not know this, but I’ve been renting out properties for short-term stays and corporate housing for years. It started with the house I was living in back in 2015. I’d rent it out on Airbnb when I’d travel. Once my wife and I moved in together in 2018, I turned it into a full-time short-term rental. After some renovations and figuring out how to optimize guest experiences, I started turning a nice profit.
Real estate has always been a secondary passion of mine—my mother has been in the industry as a broker for almost three decades—and once I had figured out how to maximize my profit on these properties, I wanted to continue to grow my portfolio.
For the past twelve months, I’ve spent every extra second available searching online for properties I could turn into rentals. I looked at condos, multi-family units, manufactured homes, single-family homes, and even undeveloped land. I looked at places in town, places near hospitals and universities, and places out in the country that would be good vacation spots. I looked at hundreds of properties and toured many of them with several different brokers.
And then I found the one.
It was a 1.3-acre piece of waterfront land looking out at four miles of Pamlico River, the river I grew up on swimming and fishing. It had enough land for me to put multiple little vacation spots on—a three-bedroom house, a camper or tiny home, and maybe even a yurt (which are surprisingly popular right now).
It was adjacent to the ferry that took people from one side of the river to the other and while that could be a deterrent for some people, I was going to lean into it and make it part of the property’s story. I’d call it the “Ferry Keeper’s Cabin.” Short-term guests love that sort of stuff.
And the absolute best part about this property is that it had its own river beach. Most riverfront properties down there have rock or bulkheads, but this had a 280-foot cove of sandy beach. A private beach looking out at four miles of water. The picture would sell itself.
I made an offer and it got accepted that day. I went to work on my plan immediately
I called tiny home builders, manufactured home dealers, RV/camper owners, and everyone in between to figure out how I could best make this work. I got estimates for septic systems, electric hookup, driveway installation, and more.
I created the vision. I even started naming little parts of the property.
I fell in love.
Not only would this be an income-producing property for me, but it would also be a vacation home for my family to spend weekends on the river that meant so much to me.
But then I went away for this three-day trip for our first founders' meeting of this new business.
And we determined, as a group, that we all needed “skin in the game.” This meant something needed to be at stake and it needed to hurt if we lost it. So we all decided to make a significant monetary investment in this venture as a sign of our commitment to the idea.
It was the most I’d ever invested at a single time.
But I was investing in myself and my team and I believed in what we were building.
Then it hit me like a ton of brick. I couldn’t do both this and the river beach.
I had the money for one or the other. And I certainly didn’t have the time to pursue both while still making the money I needed to make to cover my bills and expenses.
I didn’t know what to do. I had done a lot of pre-work already for the river property and I’d paid my due diligence and earnest money deposits. But I could afford to sacrifice those things. The hard part was how much I had already emotionally invested. That, I didn’t feel like I could lose.
I wanted to cry.
But I didn’t have time to. I had to make the decision before I left the next day.
The out-of-pocket monetary cost would be about the same. Both would require a lot of my time. And I was very interested in pursuing both, outside of their ability to generate income for me.
But one would change my year. The other could change my entire life.
So I chose the one that could change my life and hoped that if it was meant to be, another sandy river beach (metaphorically and/or literally) would present itself to me in the future.
The word “decide” derives from the Latin roots, de (“off) and cadere (“to cut”). It literally means that when we decide on something, we “cut off” all other options except those that matter most.
There is no success without some sort of sacrifice.
And a sacrifice cannot be made without a clear and clean decision to do so.