The Insurance Guys Podcast

Jordan Gerheim runs Outside Chief Legal, and Bradley Flowers found him the way most business owners find a lawyer: he needed a cease and desist sent, and it got handled in about eight minutes. The argument of the hour is that this is exactly the wrong way to do it. Jordan's firm sells what it calls partner plans, a fixed fee the client is supposed to exhaust, on the theory that a lawyer who already knows your business is cheaper than one learning it during a crisis. He and the hosts work through the pile of things agency owners skip: the LLC agreement pulled off the internet that is currently ending both a business and a friendship, the employee handbook that gets read in court either for you or against you, the non-disparagement clause that belongs in every severance agreement, the carrier contract Scott Howell admits he has never read word for word, and the commission quoted at 18 percent and written at 15. The part to file away is the AI stretch. Anything you type into a model without an attorney directing it is discoverable, and smart lawyers have gone from asking for your social media to asking for your prompts. Show Overview 00:00 Cold open and sponsors 01:04 Welcome, and the shirt change nobody warns you about 02:42 The new phone system, and why Bradley tried an answering service first 06:09 Is the AI receptionist ready yet? 07:27 Guest introduction: Jordan Gerheim, Outside Chief Legal 10:18 The cease and desist that took eight minutes 11:41 The partner plan, and a law firm you are supposed to exhaust 14:02 Building a house without a foundation 14:46 The lawn care analogy for legal work 15:46 Why switching carriers means explaining your business all over again 17:10 The LLC agreement off the internet that ended a friendship 18:16 The employee handbook that works for you or against you 19:17 LLC or S corp, non-competes, and the day one checklist 20:18 Asking legal questions in Facebook groups 21:00 Confidently wrong, and the New Balance theory 22:02 Regulatory opinions before you enter a new state 23:04 Whatever happened to the non-compete ban 23:58 The real game is out-legaling you until you quit 24:27 What a non-compete is actually trying to protect 25:20 Living wills, power of attorney, and Operation Hamilton Bridge 26:51 The silver tsunami, and who is licensed to inherit your agency 28:25 A handbook is a living document, not a file cabinet 29:05 AI and the legal industry 31:07 Closed models, and forty thousand pages of discovery 32:28 Replicating the bookkeeper with Claude, then keeping her anyway 33:40 The most ChatGPT'd cease and desist you have ever seen 35:33 What AI still cannot give you: confidence 36:03 The Grant Cardone deposition and the question about AI prompts 36:55 Discoverable: what that actually means in a lawsuit 37:40 They used to ask for your social media, now they ask for your AI 38:22 Drafting it with AI does not make your lawyer's job easier 39:15 If the attorney provides the AI, is it privileged? 40:32 Recording your calls, and what refusing to says about you 41:24 Risk management is not risk prevention 43:15 The non-disparagement agreement that belongs with severance 44:12 Why severance is a new contract, and what else belongs in it 46:15 Protect and promote: the other half of what a lawyer is for 47:21 The carrier contract you signed and never read 48:46 The commission quoted at 18 percent and written at 15 49:24 Who has the leverage, and what to do when it is not you 51:22 What defense work teaches you that carriers never ask about 52:54 The $42,000 the MGA forgot to pay 54:14 A carrier will never pay more than it is contractually obligated to 56:11 Do agency owners know their own coverage? 57:40 Do not write your own E&O, and do not write your own cyber 59:21 The cyber endorsement that does not really cover anything 01:01:06 Generative AI exclusions are starting to show up 01:01:57 Every mastermind is now a two day AI conversation 01:04:06 Where AI actually shows up in quoting right now 01:05:11 Scott's plan to go be an HVAC contractor 01:07:56 LiDAR, Claude, and an estimate that came within $805 01:08:51 What the NAIC is actually regulating 01:09:41 The VAs who made up the data, and the carrier that shut it all down 01:11:22 It is still a relationship business 01:11:58 The carrier that would not appoint them for using too much technology 01:13:29 The QR code problem Silicon Valley does not see 01:15:33 Two kinds of agency owners: sued, and going to be sued 01:16:21 Why your staff treats a lawsuit like a copperhead in the room 01:19:10 Telling your own client to go see an attorney 01:20:22 The people who hate lawyers call one first 01:21:03 How to reach Jordan 01:21:30 House divided, and the moment the rivalry turned 01:24:25 Rewards come from action, and the sign off

Julie Shiyou-Woodard, President and CEO of Smart Home America, explains how Alabama went from an insurance market that bottomed out in 2006 to one that holds steady while the states around it burn. Her own household got the non-renewal letter on a Monday and a tripled premium quote from the same carrier on a Wednesday. What followed was roughly fifteen years of what she calls persistent engagement: seven pieces of legislation, building code amendments, third party verification by a role her team calls Switzerland, and a no match grant program funded by a twenty five dollar bump in every Alabama agent's annual license fee. The proof arrived with Hurricane Sally, which crawled in at four miles an hour and left homes near Fairhope sitting in the eyewall for eight hours. Ninety nine percent of fortified homes came through it, many without a claim at all, and other states' insurance departments started calling to ask what Alabama was doing. Julie walks through how another state copies the model, what an agent somewhere else should do first, and why the insurance discount is the byproduct rather than the point. Before any of that, Bradley Flowers explains the black bear that was standing in his garage. Show Overview 00:00 Cold open and sponsors 01:04 Welcome, and the incomparable Bradley Flowers 01:49 Auburn fans are the New York Jets of college football 03:33 The black bear in Bradley's garage 04:20 Twenty nine seconds, and the attack numbers nobody expects 05:08 Guest introduction: Julie Shiyou-Woodard, Smart Home America 07:46 Julie's bear solution: play the podcast in the garage 10:01 The bear that got the hood open, and the claim they paid 11:11 Why has nowhere else followed Alabama's lead? 12:36 Changing insurance is like turning the Titanic 13:39 The origin story: thought leaders talking before Ivan hit 15:14 Ivan, then Dennis, then Katrina eleven months later 16:02 Why rebuild it the same way it just failed? 16:13 Finding IBHS, and dropping the bunker for one hazard 17:28 2006: dropped on Monday, tripled on Wednesday 18:36 Fortified is not a product you buy at Lowe's 19:34 The glass dome over the Alabama coast 20:13 Third party verification, the role they call Switzerland 20:37 Seven pieces of legislation and a lot of nagging 22:03 Within 24 hours of moving here, somebody tells you to buy fortified 22:56 The discount is the byproduct, not the reason 23:24 What the Hurricane Sally claims data actually showed 24:32 Four miles an hour, eight hours in the eyewall 26:03 Lose the shingles, keep the water out 27:00 Ninety nine percent, and why other states started calling 28:15 Strengthen Alabama Homes, and why this is not only an Alabama story 29:19 You have to pay a homeowner to make a good decision 30:52 What a no match grant has to accomplish 32:16 The discount that does not depreciate 33:17 Who sponsored it, and the account the general fund cannot touch 34:35 The license fee that pays for all of it 35:10 Ten thousand dollars, first working day of the quarter 36:16 First come, first served, and not income based 36:58 Building it to be fraud proof 37:45 How another state copies this 38:47 The nonprofits that cover the economic barrier 39:21 What an agent in another state should do Monday morning 39:53 Why California is still on the Fisher-Price version 41:16 Water sensors, Ting, and carriers mailing you the kit 42:38 The smart nine volt battery and the total loss clock 44:11 Agents as first responders

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.