At Arena, we believe the best business stories start long before the first client meeting or policy sold. They begin in childhood homes, on sports fields, and in the quiet moments when people decide what kind of life they want to build.
Hunter Rappleye’s story is exactly that — a winding path from busy family life and competitive golf greens to becoming a commercial insurance broker focused on helping business owners protect their legacies.
Growing Up in a House Full of Siblings — and Competition
Hunter grew up in what he calls a “madhouse.” He’s the youngest of five kids, including triplet older brothers and an older sister. His dad always joked that he “didn’t like money” because he kept having kids. But despite the chaos, Hunter wouldn’t trade his childhood for anything.
From an early age, competition shaped him — whether it was striving to match his sister’s school achievements or chasing his brothers’ sports records. Golf became Hunter’s primary sport, and he dedicated countless hours to it, hoping it might help him earn a college education. Summers meant 70-hour weeks on the golf course, grinding toward improvement.
“I knew I wanted to use one of those sports to go to school and try to get education discounted. Golf was probably my best option.”
Arena Conversations: Flexibility and Family
Though golf took Hunter far, he always knew he wanted a career that offered flexibility — a lesson he learned from his father, who worked in commercial lending and was always present at Hunter’s games.
“My story is one of my dad always showing up… I wanted the same experience, where if my daughter does dance once a week at five o’clock, I always want to be there.”
Hunter’s dedication to his family life is at the core of his career choices. It’s clear in the way he talks about his wife (whom he met through a mix of church connections and a dating app) and his two daughters.
From Math Major to Commercial Insurance
Despite majoring in math in college, Hunter didn’t initially plan for a career in insurance. After a stint in personal insurance and financial planning, he joined InterWest Insurance, following his brothers once again.
He discovered that commercial insurance fit his strengths — understanding numbers, building relationships, and problem-solving for business owners. Unlike life insurance sales, business insurance felt necessary and tangible.
“You have to have business insurance… If you don’t have a great relationship with your current broker, then let’s have a conversation because you have to have it.”
The Arena of Commercial Insurance: Learning, Serving, and Growing
Hunter is candid about the learning curve he faced early in his insurance career, especially coming in as a young professional during COVID. He credits InterWest’s strong training program and support from experienced brokers with helping him bridge gaps in expertise and earn clients’ trust.
He also learned the critical balance of technical knowledge and emotional intelligence. Building rapport, asking the right questions, and truly understanding clients’ needs became central to his approach.
“Sometimes you just barf on the business owner about coverages… but if they don’t have a problem or if you don’t know what their problem is, it’s just total jargon.”
Looking Ahead: Giving Back and Building a Legacy
Today, Hunter remains dedicated to his clients while beginning to mentor newer brokers, helping guide the next generation in the industry. His definition of success reflects not just professional achievement, but being present for family and building a life rooted in purpose.
“Success to me is being able to provide for my family, but also being able to see them grow up… If I was at the top of the list for numbers, but I’m gone on Saturday mornings and I’m missing stuff, that’s not success to me.”
At Arena, we love stories like Hunter’s — real journeys of grit, growth, and the commitment to serve others both in business and at home.
Join the Conversation
Want to hear more inspiring stories? Subscribe to Tell Us Your Story…Welcome to the Arena! and stay tuned for more conversations with changemakers who share their story, just like Hunter!
Listen to Hunter’s story and episode: Click To Listen!
Be a guest on our show: Click to submit your name and story!