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Jake Holehouse, 31

HH Insurance Group, principal agent

  • By Louis Llovio
  • | 5:00 a.m. October 14, 2022
  • | 2 Free Articles Remaining!
  • Class of 2022
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Jake Holehouse was in ninth grade when he got an 82% in Spanish.

He was a student at Admiral Farragut Academy in St. Petersburg at the time and got an A in every other class.

Not bad, most any parent would think. But Holehouse’s father, Ron, was not any other father.

The insurance entrepreneur grew up one of 10 children and had to work hard to build something, something to give his own kids. An 82% was simply not tolerated.

“My dad and I had very different definitions of acceptable grades,” says Holehouse, now the principal agent at HH Insurance Group in St. Petersburg.

To teach his son the value of hard work, and the dedication needed to get the proper grades, soon after the report card arrived Ron began driving his son 82% of the way home. The other 18% was a mile and a half.

For those unfamiliar with the Academy, it is a prep school that includes mandatory participation in Naval JROTC. That meant Holehouse was in fatigues and carrying his school bags. His father, ever the strategist, had notified neighbors of the punishment and asked they refuse the boy a ride home when he called, which, of course, was the first thing Jake, who thought he could outsmart his dad, did.

“The first day I was pretty mad about it,” he says. “And from there I basically went before and after school every day to the Spanish classroom and did tutoring, to the point of being able to know enough to get that grade up.”

While the lesson may sound harsh to some, for Holehouse it is a reminder of the lessons about hard work and dedication his father taught him.

These are lessons that have guided him in the decades since, giving him the confidence to build his own insurance practice. Holehouse, who went to Florida State University to study insurance, first went to work for a carrier after graduation. He spent about six months there and then joined the family agency, starting in an entry level customer service position and working his way up into sales.

Regions Bank acquired the company in June 2015. But Holehouse wasn’t happy with the corporate structure and left not long after. “The entrepreneur within me wasn’t really the right fit,” he says.

He had a noncompete, so for the next two years worked for a carrier again until it expired.

In 2018, he reopened the business.

“We started at zero,” he says. “It was basically three of us walking in the front door that day and having zero policies and being like, ‘Alright, we’re going to start growing.”

Nearly five years later, the company has 47 employees.

What it doesn’t have is Ron.

He died about six months after the agency opened.

“It was really cool and fun to be able to hit the reopen switch while he was still alive, while he was still here,” Holehouse says. “I’m sure he was super proud.”


City of residence: St. Pete Beach

Employer: HH Insurance Group

Title: Principal agent

Birthplace: Florida

Years in area: 31

Marital status/children: Married, no kids

Alma mater/degree: Florida State University, BS and MS

What community group or organization are you most involved with? Seminole Boosters, Tampa Bay Watch

Are you working from the company office, home office or hybrid? Me, office. Most of our team is in a hybrid role.

What’s the weirdest job you’ve ever had? Or the weirdest task you’ve ever been assigned? In college we partnered with the FSU Antarctica lab to use their freezers and build ice luge blocks to sell for tailgates.

What’s your top tip for being productive? I create a plan and work my plan on a daily, weekly and yearly basis. Most people underestimate what they can accomplish in a year and underestimate what they can do in 10 years. I typically break my goals down into family/relationship, work, personal, vacation and giving goals to help create balance compared to performance-only type goals.

If you could have a side hustle, what would it be? Charter fishing captain

What’s your favorite off-hours activity? Watching Florida State football and fishing

What’s the most significant item on your life bucket list — and what’s keeping you from completing it? Scuba diving the Great Barrier Reef. The 25-hour flight.

What’s your favorite podcast? Joe Rogan

At what percentage on your phone do you start to get Low Battery Anxiety? 35% to 40%

What are the top three apps used on your smartphone? Outlook, phone and messages

What books are you reading now? Awaken the Giant Within by Tony Robbins

What’s your go-to music genre, band or act to be inspired? "Lose Yourself" by Eminem

Who would play you in the movie of your life? Gabriel Macht

Where is your happy place? Florida Keys

Describe yourself in three words: Achiever, focus, grateful

Who is your mentor for your career and why? My dad. My dad grew up as one of ten kids in the typical Irish Catholic family. Through incredibly hard work from having little he created an entrepreneurial foundation that I have been able to build on.

What are the biggest lessons you have learned from your mentor? Hard work, anything is achievable, find your passion and build your life around it, take risks and never stop learning or growing and always work to grow yourself and those around you.


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