What it really takes to build an agency from scratch. Capital, grit, risk, hiring your first producer, surviving year two — the unfiltered founder experience.
42 episodes from Craig Pretzinger & Jason Feltman, hosts of The Insurance Dudes Podcast
04/21/2026 · 8 min read
Kirk Chester built GRIT Insurance Group by going deep on blue-collar niches—construction, manufacturing, contractors—instead of chasing every account. Here's the execution-first playbook he shared on The Insurance Dudes.
03/28/2022 · 5 min read
The identity crisis is real: are you a salesperson who owns a business, or a business owner who sells? The answer to that question shapes every major decision you make. This SOLO Playbook episode is about getting clarity on who you are and what that means for how you run your agency.
03/02/2022 · 4 min read
The insurance agents who build something significant share a willingness to take calculated risks that their more cautious competitors won't. This SOLO Playbook episode is about the difference between recklessness and boldness — and how to make the moves that actually matter.
10/02/2021 · 5 min read
Javier Najera's story involves the kind of agency lows that most agents would find career-ending. He didn't end his career. He used the disaster as fuel for one of the most instructive rebuilds in independent insurance. This recast brings his story back because it's exactly what agents in a hard stretch need to hear.
09/18/2021 · 5 min read
Dave Williams built multiple successful businesses and carries the kind of competitive drive and genuine heart that makes a rare combination. This recast revisits the lessons from his original appearance — because they're worth hearing again.
09/18/2021 · 6 min read
Dave Williams built and sold multiple businesses before landing in insurance. His framework for thinking about risk, growth, and the entrepreneur's relationship with failure is the recast this audience needed to hear again.
08/21/2021 · 5 min read
Dr. Alex Mehr co-founded Zoosk, scaled it to over a billion dollars in revenue, and then kept going. This recast brings back one of the most expansive conversations in Insurance Dudes history — on what it actually takes to build something significant.
07/02/2021 · 5 min read
Every agency owner who wants to grow faces the same fork in the road eventually: do you build it from scratch through production and marketing, or do you buy a book that already exists? Both paths can work. Both paths can fail spectacularly. The one that's right for you depends on factors most people don't analyze carefully enough.
06/28/2021 · 6 min read
The business problems most agency owners think they have — the underperforming producer, the stalled growth, the energy drain — are often downstream of something that's happening in their head. The mental game of agency ownership is real, it's demanding, and almost nobody talks about it directly.
06/18/2021 · 5 min read
Every dollar you spend in your agency either buys you something today or builds something for tomorrow. Most agencies are spending almost everything on today — and then wondering why tomorrow looks exactly the same as this year.
06/14/2021 · 5 min read
The conversations every agency owner avoids — with underperforming staff, difficult clients, and their own reflection in the mirror — are exactly the conversations that determine whether the business grows or stalls. Courage isn't a personality trait. It's a business skill.
05/06/2021 · 5 min read
Julian Chambers returns to break down what happens after the commitment — the real work of figuring it out in motion and why most agents underestimate how good they are at it.
05/05/2021 · 5 min read
Julian Chambers built something significant in insurance by doing what most agents won't: committing before the path was fully clear and trusting himself to figure out what came next.
04/09/2021 · 6 min read
Part 2 with Matt Dietz moves from the gritty scratch-build years into the growth phase — the specific decisions, personnel moves, and mindset shifts that took his agency from established to expanding.
04/09/2021 · 6 min read
Jason revisits the Garrett J. White episode and pulls out the most durable and provocative pieces — the unfiltered perspective on why most entrepreneurs stay small and what it actually takes to change that.
04/07/2021 · 7 min read
Matt Dietz built his agency from nothing — no inherited book, no partner's clients, no soft start. Craig digs into the gritty early chapters of that story and the principles that made the foundation hold.
06/15/2020 · 6 min read
Six companies. Fifty million dollars in combined sales. And the most important thing Mike Watts will tell you has nothing to do with revenue.
04/10/2020 · 6 min read
He was thirteen years old when he figured out that someone had to do the work and it might as well be him. By the time Travis Gensler got into insurance, he'd already been an entrepreneur for most of his life.
03/27/2020 · 7 min read
Katherine Kinney has been a life coach, a yoga and meditation instructor for eight years, and a business owner for twenty-one. Her take on what actually drives sustainable success will challenge how most insurance agents think about performance.
02/19/2020 · 7 min read
After sitting down with Entrepreneurs On Fire founder John Lee Dumas, the conversation kept rattling around in my head. Here are the key takeaways from that interview and how they translate directly into actionable strategies for insurance agents.