The Insurance Guys Podcast

Scott Howell opens the books on air: I Protect Insurance has been losing money month over month for most of the year, and he says the quiet part out loud, that everybody else's agency is apparently perfect and only his is in a soft market. Clint Orr, now a partner and owner after thirteen years together and a buy sell agreement that finally got signed over lunch at Taco Mama, joins Scott and Bradley Flowers to walk through what they actually did about it. The two have been meeting on Google Meet for an hour a day with a spreadsheet from fractional CFO Carrie Wallace, working tab by tab through salaries, IT, travel, advertising and professional fees, and in a single week they cut just under $50,000 in annual expenses. That includes offices that exist only as a place for an employee to sit, more than a thousand dollars a month in AI subscriptions spread across four ChatGPT accounts and three Claude accounts, and seat licenses nobody was using. From there Clint lays out SummerSlam, the three KPI team contest built to carry the agency through the dog days, and what he had to unlearn going from top producer to leader.

Show Overview

01:06 Welcome, and the incomparable Bradley Flowers

01:53 Pet peeve: the brand new territory sales manager who corrects you

03:04 Shorter is always better, and banks are the worst offenders

05:22 The unsolicited calendar invite and the unsolicited drop by

07:03 Part two: Clint Orr, now an owner at I Protect Insurance

08:34 The daily Google Hangout through the financials

11:48 Why Clint wanted the operations side

12:26 Lead block and metaphorical touchdowns: hitting the inflection point

14:25 Everything you never see until you have to do it yourself

16:00 Kenneth leaves, and the smart plug named Kenneth

18:39 The F reorg, the ten thousand dollar bill, and signing at Taco Mama

20:24 Do not hand somebody ownership six months in

21:23 The admission: losing money month over month in a soft market

22:45 The fractional CFO, the spreadsheet, and the tab by tab review

24:10 Just under fifty thousand dollars in annual expenses, gone in a week

25:23 Which offices actually earn their rent

27:29 The hidden cost of an office: coffee, toilet paper, printer paper, internet

28:57 Cut mode, and why you read the bank statement instead of QuickBooks

29:38 Over a thousand a month on AI: four ChatGPT accounts and three Claudes

31:15 Consolidating the tools instead of collecting them

32:17 Seat licenses, shared logins, and website maintenance

33:44 Try to cancel and watch the fifty percent off appear

34:15 The Adobe Sign story: offboarding matters as much as onboarding

36:35 Counting walk ins with the security system instead of guessing

38:25 The monkey off the agency's back

39:40 SummerSlam: three KPIs, team goals, and real prizes

44:18 Two new producers, a sabbatical, and a summer that held

46:28 No longer siloed

47:21 When money is the trigger, you do not leave it at the door

48:30 From hustler to leader

51:06 The gift bag, the birthday calls, and what changed

53:21 One percent better: ranch ad

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

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

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.

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.

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.

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.

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.

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.

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.