Connor MacLeod RI grew up in Portsmouth, Rhode Island, where the ocean was part of everyday life. Raised in a close and supportive family, he learned early on the value of responsibility, hard work, and showing up for others. Those lessons stayed with him as he began shaping a life tied closely to the water.
After graduating high school, Connor attended several maritime schools and earned multiple licences and certifications. At just eighteen, he achieved his 100-ton Master’s Licence, an early milestone that allowed him to step into leadership roles long before most people his age. He started his career in commercial fishing, working on offshore lobster boats and gillnetters. The long hours and demanding conditions helped build the discipline and calm focus he is known for today.
Connor went on to captain rescue and tow boats, passenger ferries, and the Newport Harbormaster vessel. In 2014, he joined Reinauer Transportation as a Second Mate and PIC Tankerman, gaining years of experience in precision-based maritime operations. While working offshore, he quietly began building something of his own.
In 2018, Connor founded Tall Tailz Charters. What began as a part-time project grew steadily, and by 2024 he committed to it full-time. His charter gained statewide attention after breaking the Rhode Island state-record tautog in 2021 and again in 2025.
Beyond his career, Connor is deeply committed to giving back. He founded the Dennis Fitz Foundation to support addiction awareness and regularly donates fishing trips to charities and foster youth. His life reflects steady growth, purpose, and a belief that meaningful work often starts small and builds over time.
What is your typical day, and how do you make it productive?
My days usually start early. I like being up before the sun, especially when I’m running trips. I check weather, tides, and gear first. That routine keeps me focused. If I don’t get organised early, the rest of the day feels rushed. Productivity for me is about preparation, not speed.
How do you bring ideas to life?
Most of my ideas come from frustration. If something doesn’t work the way it should, I pay attention to that. That’s how Tall Tailz Tog Jigz started. I couldn’t find a jig that did what I needed, so I built one. I test ideas quietly, improve them slowly, and don’t rush to show them off.
What’s one trend that excites you?
I’m encouraged by how many younger people are reconnecting with hands-on work and outdoor skills. Fishing, boating, and craftsmanship are becoming appealing again. That matters because these skills teach patience and accountability.
What is one habit that helps you be productive?
Keeping things simple. I don’t overcomplicate plans. I make short lists and stick to them. Once a task is done, I move on.
What advice would you give your younger self?
Slow down a little and trust the process. You don’t have to prove everything all at once.
Tell us something you believe almost nobody agrees with you on?
I think most people already know what they should be doing. They just avoid the discomfort of starting.
What is the one thing you repeatedly do and recommend everyone else do?
Show up consistently. Talent matters, but reliability matters more.
When you feel overwhelmed or unfocused, what do you do?
I go outside. Even if it’s just walking near the water. Movement clears my head better than sitting and thinking.
What is one strategy that has helped you grow your business or advance in your career?
Treat every role seriously, even if it feels temporary. Every job I had taught me something I use now.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
Early on, I tried to take on too much at once. I burned myself out. I learned that pacing yourself leads to better decisions.
What is one business idea you’re willing to give away to our readers?
If you’re skilled at something niche, teach it. Workshops and small group learning are undervalued.
What is one piece of software that helps you be productive? How do you use it?
I use simple calendar and notes apps. Nothing complex. If it takes too long to manage, it’s not helping.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
I enjoy biographies. Hearing how others worked through setbacks puts things into perspective.
What’s a movie or series you recently enjoyed and why?
I enjoy documentaries. Real stories remind you that progress is rarely overnight.
Key learnings
- Consistency and preparation create long-term results more reliably than speed or hype.
- Practical ideas often start as solutions to everyday problems.
- Hands-on experience builds judgment that can’t be replaced by theory.
- Giving back strengthens both community ties and personal purpose.