Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?
Michael: I’ve been lucky to build my career around things I’m genuinely passionate about, and this is actually the third company I’ve run that’s tied to something I love.
My first venture was co-founding a sports recruiting business that helped kids pursue their dreams of playing sports at the college level and beyond. After that, I built and scaled a business focused on helping nonprofits raise money to create global impact. And now, as the CEO of Boatsetter, I’m lucky to be doing something that taps into one of my biggest passions—being outdoors and spending time on the water.
For me, I’ve always found that being on a boat is a magical experience. It’s one of the places where you can actually disconnect and spend time with family and friends. Some of my favorite memories are from being on the water—whether it was fishing with my dad when I was younger, learning to wakeboard as a teenager, or scuba diving while traveling. These days, I’m making more memories with my family and kids, and even learned how to wakesurf recently!
Adam: In your experience, what are the key steps to growing and scaling your business?
Michael: To successfully grow and scale Boatsetter, it’s essential to stay laser-focused on the core value proposition of this two-sided marketplace: empowering boat owners to earn income from their vessels while giving millions of people access to incredible on-the-water experiences.
Achieving this requires a two-pronged approach. First, we need to continually empower owners. We obsess over how to enhance the platform with tools that help owners scale their business, how we provide them with innovative marketing tools, and how we provide dedicated support to help them thrive. Second, we need to grow the brand and the category. We do that through targeted marketing, fostering partnerships, and delivering a seamless and enjoyable rental experience that encourages repeat bookings. When owners provide a great experience, guests become our greatest ambassadors. It’s a flywheel.
Adam: What do you believe are the defining qualities of an effective leader?
Michael: Defining qualities of an effective leader include the ability to build and scale a world-class team by setting a clear vision, empowering individuals with autonomy and trust, and fostering a culture of continuous learning and growth. This is achieved by creating an environment rooted in trust, high standards, and mutual support. A culture of experimentation encourages learning from both successes and setbacks, while new challenges and opportunities drive ongoing development. Open communication and regular feedback ensure everyone understands their impact and feels supported. At Boatsetter, celebrating collective wins reinforces a shared commitment to the mission and inspires continued excellence across the organization.
Adam: How can leaders and aspiring leaders take their leadership skills to the next level?
Michael: Get comfortable with uncertainty and remain relentlessly curious. Seek mentors, surround yourself with people smarter than you, and constantly reflect on what’s working and what’s not. At Boatsetter, we’ve built a culture around curiosity, and we embrace continuous learning and development.
Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?
Michael: First, double down on your strengths. Know what you’re uniquely great at and build from there.
Second, stay customer-obsessed. Use data and feedback to understand what your users want and need, even before they ask for it.
Third, build a mission-driven culture. People follow passion. If your team believes in the mission, they’ll go above and beyond.
Adam: What is your best advice on building, leading, and managing teams?
Michael: Hire individuals not just for what they’ve done, but for where they’re headed. Create an environment where people are empowered, supported, and excited about the work. At Boatsetter, we’ve built a culture where the team actually uses and loves the product, and that makes a massive difference in their commitment and creativity.
Adam: What are your best tips on the topics of sales, marketing, and branding?
Michael: Sell experiences, not just products. At Boatsetter, we don’t just rent boats, we sell happiness and unforgettable memories on the water. That mindset shifts how you market, position yourself, and communicate with your audience. Also, know your demographics. For instance, we’ve tailored our offerings based on Gen Z’s rapid growth on our platform and created curated experiences that align with their values—accessibility, connection, and adventure.
Adam: What is the single best piece of advice you have ever received?
Michael: “Hire for where they are going, not where they are.” That advice, from a former boss, changed how I build teams. Talent is important, but potential and trajectory matter just as much, sometimes more. When you invest in people who are on the rise, they grow with your business and often exceed your expectations.
