Double Duty on the Water and Land: My First Week as a Dual Business Owner
When you build something from adversity, every win hits harder—and every loss teaches you more. Both Choppy Seas Fishing and Choppy Seas Landscaping & Design were born from tough seasons in my life, and if you’ve followed my story, you know that already. If not, I’d encourage you to check out our documentary or dig into some of my earlier blogs.
This past week marked my first official one running both businesses side by side. It was intense, unpredictable, and honestly—exactly the kind of week that reminds me why I started all this in the first place.
Planning for a Packed Week
With commercial striped bass season opening here in Massachusetts, I knew things would get hectic. On Sunday night, I mapped it all out:
Monday, Thursday, Friday (maybe Saturday): Landscaping jobs
Tuesday & Wednesday: Commercial fishing runs
We prepped the trucks, tuned the mowers, stocked the coolers, and made sure the boat was dialed in. Jeff—who works with me on landscaping and also serves as my first mate—helped get everything lined up so we could hit the week running.
Early Starts and Quick Turnarounds
Monday started with a big pruning job that we finished by 4 p.m. I timed it that way so Jeff and I could go home, meal prep, talk strategy with my dad, and catch a couple hours of sleep before our 3:30 a.m. fishing departure.
Tuesday morning, we steamed out early and marked some fish—but they weren’t biting. Then came the gut punch: we had brought the wrong gear to P-Town. Rookie mistake. It stung, but that’s how you learn.
On a brighter note, Tuesday also marked the launch of our “Choppy Seas” ice cream flavor in collaboration with B’s Homemade Ice Cream. Cookie dough, Oreos, and blue sprinkles—made in honor of the commercial guys and our documentary. We stopped by, grabbed a pint, and hit the reset button.
Small Wins, Big Lessons
Wednesday we had the right gear—but no fish. We landed one keeper, lost another at the back of the boat, and chased hunches. One paid off: I threw a live mack in a random spot, and it worked. A small win, but I’ll take it. We sold the fish, grabbed a bite, and rolled into the next day.
Thursday? Brutal. My dump truck started rumbling mid-mulch run and died out. Not exactly ideal when you’ve got a full landscaping schedule. It’s now in the shop, and I’m hoping it’s a quick turnaround—jobs are stacking up.
Friday was a full catch-up day: 26 or 27 lawns on the list. We hustled, borrowed a second mower, and powered through in the heat.
the importance of a day off
Saturday was supposed to be another workday. But sometimes, you need to listen to life when it tells you to pause. I took the day off to spend time with my fiancée Megan. We had breakfast, hit the beach, and took a breath after a long week of chasing tides and mowing lines.
Now I’m sitting in the sauna, writing this blog and already planning next week.
final thoughts
Running two businesses isn’t glamorous. You lose fish. Your truck breaks down. You work until your hands stop working—but it’s all worth it. These hard weeks make the wins taste sweeter.
To anyone out there chasing their own dream—whether it’s with a rod in hand, a shovel, or something entirely different—remember this: adversity builds resilience. Stay moving. Stay grateful. And keep going.
– John Dentino
Owner, Choppy Seas Fishing & Choppy Seas Landscaping & Design