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.