The Insurance Guys Podcast

Seth Zaremba hands the episode its title seventeen minutes in: halfway to somewhere is 100% to nowhere. He says it about a rental Chevy Traverse that has a touchscreen and a row of physical buttons doing the exact same job, which Bradley Flowers calls the most hideous confusing thing he has ever seen, and which both men immediately recognize as what an agency looks like when it tries to be all things to all people. The spine of the hour is Tesla's full self-driving as the working analogy for AI in an insurance agency. Scott Howell opens with the hot take that FSD is the biggest invention since the airplane. Seth, who lets the car drive 94 percent of his miles, explains why the legacy automakers cannot shortcut their way to it, then runs the same argument at insurance processing: the infrastructure has to be built before anything drives itself. From there they get into what agency staff actually fear about AI, the Acrisure layoffs and whether AI was the reason or the excuse, why a new AI tool gets trained like a hire instead of installed like software, and what happens to personal auto premium once the cars are measurably safer. Seth closes on what ships next for Service Center: email first, then voice.

Show Overview

00:00 Cold open and sponsors

01:03 Welcome, and the incomparable Bradley Flowers

01:47 Hotel waffles, and whether Ryan Hanley wanted to be a great American

02:11 The newspaper on the porch, and the welfare check

06:39 Guest introduction: Seth Zaremba, BeAtomic

08:48 The hot take: FSD is the biggest invention since the airplane

09:55 Seth's numbers, and why he almost never drives

10:42 Road rage, cortisol, and the Oura Ring

13:52 Will every manufacturer have this in fifteen years?

14:01 Why the legacy automakers cannot shortcut the infrastructure

15:04 The Chevy Traverse with buttons and a screen that do the same thing

16:17 Trying to be all things to all people, in cars and in agencies

17:29 Halfway to somewhere is 100% to nowhere

18:34 What FSD and the Service Center rollout have in common

19:48 Will AI take my job? What Bradley is telling his team

20:51 The Acrisure layoffs, and AI as the excuse

21:46 A bonus for any employee who finds a job to automate

22:46 Expense or revenue: the only two levers a top 100 can pull

24:34 Treat a new AI tool like a hire, not like software

26:26 Buy stock in the human, sell stock in the processor

27:08 Carrier access, portals, and whether anyone pushes back

29:24 The walled gardens are over, and who is trying to stop it

30:21 The wild west before you get to Denver

32:00 The power drill argument for AI security

33:00 The carrier that used AI to write a letter warning about AI

34:25 Personal auto, FSD discounts, and whether the premium disappears

35:53 Liability never goes away, it just moves

37:04 Why supervised FSD may be more dangerous than unsupervised

38:33 The crash data, and what a mirror costs now

39:13 Why people hate a premium that changes every month

40:20 If every car stops for you, pedestrians get the right of way

41:52 Where Service Center is now, and what ships in October

43:16 Email is the second leg, voice is the third

45:14 Why standardization beats knowing every carrier portal

47:45 Talking to your own agency data

48:42 Which carrier to go to first, and the data that would tell you

50:12 Hiring a firm to build the agents instead of doing it yourself

51:34 Internal AI versus external AI, and where to spend

52:50 HawkSoft, Applied, Vertafore, and the AMS thaw

54:33 Rewards come from action, and the sign off

55:43 The Insurance Guys promo code and the 2027 F1 drawing

Ryan Hanley's answer to the title question is that one model is not enough yet. He runs several and treats each like an employee with its own job: Claude when a whole team needs the same projects and memory, Kimi K3 from Moonshot for everyday work at a fraction of the cost, GrokBot for agent work inside live systems, and OpenClaw when he wants no guardrails at all. Bradley Flowers brings the other half of the argument from his own hiring process, where the model started hedging on DISC assessments and taking up for the candidate instead of giving him the read he asked for. From there it turns practical. Ryan walks through an insurance prospecting build step by step: anonymize the book, have the AI define five ideal client profiles, build the contact list, then run a seven touch cold drip that adjusts on real feedback. He also explains how an agent found a hundred publishers, ranked them by likelihood, and landed his book deal by emailing five at a time. Bradley has an agent living in his service manager's inbox to win back 60 percent of her day. Scott Howell asks for the 2027 forecast and gets a market that hardens a little, plus a warning about the downward pressure building on agencies that stay out of the tech game.

Show Overview

00:00 Intro and sponsors

01:06 Welcome, and the incomparable Bradley Flowers

01:45 New studio, and the property manager on the other side of the wall

02:14 Guest introduction: Ryan Hanley, Finding Peak

03:49 The Mark Walters story: billions shifting under federal investigation

05:11 Smart people do stupid things, and rule one is do not commingle funds

06:14 Regulated versus unregulated, and what you are allowed to say

08:20 Facebook ads for realtors, and the weight loss ad that lasted eight minutes

09:54 Baseball cards, a twelve year old, and a GrokBot arbitrage business

12:28 An Airbnb run on eight programs for a thousand dollars a year

13:51 ChatGPT, Claude, Grok, OpenClaw and GrokBot, sorted by guardrails

14:27 Why Ryan moved to OpenClaw and off Claude

15:56 Running DISC assessments through AI, and the model taking up for the candidate

16:51 Kimi K3, open source, and what a Chinese model actually means

18:21 Treat every model like an employee with its own strengths

19:01 An AI agent living in the service manager's inbox

20:30 Nobody taught AI 101

21:16 Interview the AI about you before you put it to work

21:48 Easy Mode: the book deal, and where the title came from

24:35 How an agent landed the deal, five publisher emails at a time

26:30 The insurance prospecting version of all this

27:31 Five ideal client profiles, HVAC contractors, and a seven touch drip

29:05 You used to think inside the tool, now you just name the goal

30:54 How the book actually gets written: talk to text, then edit

32:34 End every prompt with: ask me your questions one at a time

33:52 The 2027 forecast: harder, but not a hard market

34:21 Do not blame the soft market, and do not take credit for the hard one

34:42 Fifty percent commercial property in a soft market

35:36 PIF and retention are the metrics, not revenue alone

36:31 The downward pressure building on agencies that skip tech

39:07 HawkSoft, Momentum, AgencyZoom, and who is actually moving on AI

41:03 Stop accepting standard development cycles

43:22 Build the feature your CRM does not have

44:55 Why private equity owned platforms do not fund AI

46:03 Hand an agent ownership of AgencyZoom

47:32 ITC, IndieTech, and the conference shakeout

48:08 Rewards come from action, and the sign off

A guest no-showed, so Scott Howell brought two stories instead. The first is an auto claim he calls the craziest he has ever heard. A customer buys a $17,000 Mazda from a dealership Scott also insures, puts liability only on it because he was in a hurry, then drops it back off for a check engine light. The next morning the dealership's technician gets T-boned at a green light, and the driver who hit him calls The General and buys a policy while waiting on the police. Between liability only coverage, garage keepers liability, and an at-fault driver with nothing in force at the time of the wreck, nobody pays for the totaled car. The owner's existing Progressive policy would have covered it if he had never called them at all. The second story is the title. An employee at a friend's agency threw a rock through a Tesla's back window on his way to work, the Tesla followed him to the office and called the police, and he was handcuffed in the parking lot at 9:30 in the morning while his coworkers watched from the window. The owner later found the search still open on his screen: what to say to the police after you throw a rock through somebody's window. Which brings Scott and Bradley Flowers to the moral, which is vet your people before you hire them.

Show Overview

00:00 Cold open and sponsors

01:03 Welcome, and the incomparable Bradley Flowers

02:26 Guest no-show, so Scott brought two stories

02:59 Story one: two clients who do not know each other exist

04:40 A check engine light, and liability only

05:05 T-boned at a green light

05:53 The at-fault driver buys a policy while waiting on the police

06:45 Garage keepers versus direct and primary

07:35 Nobody pays: three policies and one totaled car

09:00 The twist: calling Progressive is what killed the claim

09:59 He found a lawyer, and he is suing the dealership

10:38 Story two, names withheld

12:02 A rockhound, an F-150, and a Tesla that cut him off

13:23 They follow him to work and call the police

14:33 Handcuffs in the parking lot while the office watches

14:54 The browser tab left open on his desk

15:39 Were there signs? The slammed door

16:30 Vet your people, and what nine interviews at Progressive buys

17:47 Fast on the ones you want, slow on the ones you are not sure about

18:02 The AI written email that withdrew her candidacy

18:54 The Facebook comment that did dad no favors

19:20 Recap, and there is always tomorrow

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.