The Insurance Guys podcast is dedicated to agents by agents. Scott Howell and Bradley Flowers discuss all aspects of becoming an insurance agent and give real life examples of their experiences in all aspects of hiring, sales and the day-to-day reality of running your own successful insurance agency.
Site
RSS
Apple
Data updated on 27/09/2026
Recent rankings
Latest chart positions across Apple Podcasts and Spotify rankings.
Shared links between episodes and podcasts
Links found in episode descriptions and other podcasts that share them.
Discover shows related to The Insurance Guys Podcast, based on actual content similarities. Explore podcasts with similar topics, themes, and formats, backed by real data.
Ron Shroyer puts a number on the biggest decision an agency owner will ever make: one hour on Zoom and maybe a three hour dinner. That is how long most sellers spend vetting the firm that is buying the largest asset they will ever own, and it is the thread running through this entire conversation. Shroyer, Vice President of M&A Business Development at Alliant Insurance Services, returns to the show to tell Scott Howell and Bradley Flowers what has actually changed since the roll up boom. Cheap capital dried up first, and the firms that bought a hundred agencies in twenty four months never built the integration to make that scale pay, which is why organic growth across the publics has slid into the low single digits. From there Shroyer separates private equity backed from private equity partnered, explains why earnouts so often turn into earn ups, and shows how Alliant's employee ownership, 51 percent employee held with every third employee a shareholder, drives better than 90 percent retention across roughly 120 acquisitions in ten years. Bradley brings the buyer's side of it, laying out why falling insurance rates have him further from acquiring an agency than he has ever been. Then Scott asks the question nobody says out loud: why do so many owners take the big check and spend the next three years fighting the company they sold to?
SHOW OVERVIEW
00:00 Cold open and sponsors
01:03 Welcome, and the incomparable Bradley Flowers
01:55 The Hampton Inn waffle theory of customer behavior
05:00 Guest introduction: Ron Shroyer, Alliant Insurance Services
06:48 Consistency, and the empty hotel in downtown Mobile
08:30 From InsurTech to brokerage: how Ron landed at Alliant
10:14 Inside a six billion dollar flat organization
11:19 Culture is the most overused word in the industry
12:31 Knowing which agencies to listen to
14:33 Where M&A actually stands right now
16:08 Private equity backed versus private equity partnered
16:55 Buying a hundred firms in twenty four months and never integrating them
18:19 Osmosis growth, and why Bradley is not buying right now
21:01 Earnouts, earn ups, and the team you leave behind
21:46 Employee ownership and what Alliant is actually looking for
22:48 The USI and Aon shake out
23:26 The big check and the boss problem
26:07 Why acquisitions die on the vine
27:33 120 deals, 90 percent retention, integrated immediately
28:37 The Band-Aids you never ripped off before selling
29:51 AI as the excuse to cut staff, and the Nava Benefits bet
31:41 Should you sell because you are afraid of AI?
34:44 Keeping your people after the check clears
36:30 B shares, spot bonuses, and the recruiting test
37:42 How to tell whether an acquisition actually worked
39:01 Staying on as owner, and the next generation behind you
41:16 From 2.5 times revenue to multi year earnouts
43:57 Multiple bites of the apple
46:14 How to reach Ron Shroyer, and the close
How Can a New Podcast Studio and a Dumpster TV Rescue Inspire Your Insurance Agency?
Wednesday, September 16, 2026 • Duration 51:27
Scott and Bradley record from their new podcast studio, a real upgrade they plan to keep fully equipped and open to other local business owners. Bradley admits the weekly grind can start to feel like a job instead of a joy, then they get a lift from a call Scott made to a listener who is just launching his own agency.
Bradley tells the full story of his new Samsung Frame TV landing in a dumpster by accident and getting pulled back out. That leads into agency realities: the Rough Notes curse of post-feature staff turnover, Kenneth outgrowing his operations manager role, and the ongoing challenge of keeping working mothers in an industry largely run by women. Bradley floats a daycare for employees as one possible fix.
He also explains to his leadership team why he is not selling. Young kids and a lot of runway still ahead keep him all in
Insurance Unplugged
Wednesday, September 9, 2026 • Duration 37:05
On this The Insurance Guys episode, Scott and Bradley skip the guest chair and open the mailbag. They talk through who actually carries the show, why M&A multiples are still high while rates soften and a Hub International IPO looms, which carriers besides Progressive make quoting less painful (QuoteWell, Novella, Liberty Mutual, Nationwide, Travelers), why post-bind inspections keep adding work after the policy is already bound, and whether one AI tool can really answer the phones, book appointments, and talk to the CRM. No pitch. Just two agency owners answering what listeners asked.
How Can Independent Insurance Agents Break Into the Global Market?
Wednesday, September 2, 2026 • Duration 44:18
In this episode of The Insurance Guys Podcast, Scott Howell and Bradley Flowers welcome Chris Ball, chairman of WING and the man Scott calls the coolest guy in insurance, for a conversation on how independent agents can compete on a global stage. Chris walks through a career that began reluctantly in his dad’s office and later took him to aviation and aerospace work in New York, including high profile accounts like U2’s jet, then to Marsh in San Francisco before a culture clash sent him home. He shares his firsthand view of 9/11 from nearby as the planes hit and the towers fell, then explains how WING’s network of independent entrepreneurs across cultures now helps members solve complex risks together. The discussion turns to embedded insurance already common in Japan and ripe for North America, which countries treat insurance as seriously as the United States (the UK and Germany among them), and Chris’s blue ocean play: using that global independent network to go after accounts the mega brokerages want. He outlines a five year plan built on organic growth, recruiting top producers, and giving them equity in their books, and closes with a direct challenge to independent agents. You already have the capability and the partners. Go get the global work.
Fireworks Show Accident
Wednesday, August 26, 2026 • Duration 48:31
In this episode of The Insurance Guys Podcast, host Scott Howell kicks things off by introducing co-host Bradley Flowers and sharing news of their new real estate venture in Mobile before the conversation turns to Bradley’s frustration with the bureaucratic delays and inefficiencies involved in securing a simple permit to build three interior walls. Scott then formally introduces the episode’s special guest, his business partner Clinton Orr, appearing on the show for the first time, and the two recount the three-and-a-half-year journey filled with obstacles that finally made Clint an official agency owner. They discuss the decision to bring on Patrick McClure as a fractional sales leader who also served as something of a therapist for the partners, then dig into their early days starting out as competitors in the same Nationwide program office. Clint shares the gut punch of finishing that program only to discover there was no agency waiting for him, how he eventually joined Scott’s agency, struggled at first, and ultimately found his successful niche insuring real estate investors. Scott details how he used ChatGPT and Claude to draft their buy-sell agreement, which was later reviewed by attorneys and accountants, outlines his long-term goal of eventually selling the current agency and launching a new one with Clint as majority owner, and Clint opens up about navigating recent tough market conditions, the personal doubt he faced while weighing his future and family, and the genuine excitement he feels training a new hire and mentoring others who want to succeed in the insurance business.
How Did Podcasting, Branding, and Insurance Come Together to Transform Our Business Journey?
Wednesday, August 19, 2026 • Duration 01:04:02
Johnny Gwin, the podcast’s original and current producer, joins Scott Howell and Bradley Flowers to look back on the show’s early days, the discipline of reaching fifty episodes, and the technical challenges of those first recordings.
He shares career advice, walks through David Ogilvy’s core advertising principles, and traces his own creativity to television, music, and formal training at Portfolio Center in Atlanta, Ga. The conversation covers the naming of Portal Insurance, the podcast’s potential future in video and broader business topics, and what Johnny has learned about the insurance industry.
Johnny also discusses his work with Meducate AI, which uses AI-cloned physician voices for patient education, while Scott introduces his Gift Giver app idea. The episode wraps with Johnny’s straightforward editing approach of listening at 2.2x speed to catch every detail and keep the final cut tight.
The Greatest Technological Shift in Insurance
Wednesday, August 12, 2026 • Duration 54:26
Scott Howell and Bradley Flowers welcome Garrette Droege to discuss the major technological shifts reshaping insurance. Garrette shares how his theater background strengthens client work through improvisation, then explains why blockchain remains actively developed by financial institutions and how crypto is maturing into institutional digital assets and stablecoins. The conversation explores AI as a force multiplier that lets younger agents upskill quickly, covers practical tools already boosting agency productivity, and examines how AI will handle routine tasks while humans focus on higher-value work. Garrette urges owners to start experimenting with AI now, much like the early days of cyber coverage, and closes with the rising need for proof of humanity against deepfakes.
Modernizing A Billion Dollar Company
Wednesday, August 5, 2026 • Duration 59:37
In this episode of The Insurance Guys Podcast, host Scott Howell joins co-hosts Vishal Sankhla and Bradley Flowers to welcome special guest Andy Barker, CEO of Houchens Insurance Group. Scott opens by sharing a recent meeting with Auto Owners about securing a contract for his agency before the conversation turns to Andy’s impressive career path, which began with a transition from Cingular Wireless into insurance in 2002. Andy discusses his ownership of a D-1 sports training gym and how his passion for fitness shapes his business philosophy, then explores how technology such as Out Market AI elevates both customer and employee experiences. He details Hawkins’ successful intern program that develops young talent into future leaders, the history and cultural impact of the company’s ESOP, and a growth strategy built on strong organic performance supplemented by selective acquisitions. Andy also reflects on his initial skepticism toward artificial intelligence and how it has become a powerful workflow enhancement, before predicting that the independent agencies that thrive in the years ahead will be those remaining nimble and adaptable to change. The episode closes with a lively round of rapid-fire questions.
Greatest Game Changer in Insurance Agency Management You Need to Know
Wednesday, July 29, 2026 • Duration 49:24
In this episode of The Insurance Guys Podcast, Scott Howell and Bradley Flowers dig into practical agency management wins, starting with Bradley’s most profitable month happening while he was on paternity leave and the KPI-based monthly/quarterly bonus structure that replaced pure commission for account managers. They stress account rounding and a smarter cross-sell process (account managers start the conversation, then hand off to an inside sales team), debate what a true “producer” is and how to handle agency vs. self-generated leads, explore the value of strong operations roles and even a fractional COO offering, and touch on industry cycles, government pressure on rates, the costly driver-to-vehicle ratio problem, hiring experienced vs. green talent, job-shadowing candidates, and the hard call of letting a toxic employee go.
The Greatest Strategies for Building a High Net Worth Personal Lines Insurance Agency
Wednesday, July 22, 2026 • Duration 58:48
In this episode of The Insurance Guys Podcast, hosts Scott Howell and Bradley Flowers welcome Ben Walker of Custom Insurance Solutions and CIS Private Client. Ben shares his remarkable journey from owning a KFC franchise and managing movie theaters to building a thriving high net worth personal lines agency. He opens up about the early churn and burn days of writing any business possible before niching down after buying out his partner, sparked by a visit from a Pure Insurance rep. Listeners will hear practical strategies for marketing to affluent clients through targeted direct mail, understanding their mindset around risk management rather than price, and building deep relationships that win business. Ben also discusses the story behind his book Fortified, his ambitious five year plan to lead nationally while quadrupling premium, and why he values independence over selling the agency. A must listen for agents ready to elevate their high net worth game. Find Fortified on Amazon or by messaging Ben directly.
