Explore every episode of the podcast The Insurance Guys Podcast

Four members of the Outmarket leadership team join Scott Howell and Bradley Flowers: Vishal Sankhla, Joanna Paredes, Anshu Jain and Alpesh Patel. The news is Outmarket Lite, a version of the platform priced at about $1,000 a year, which Vishal traces back to a text from Bradley asking how smaller agencies could ever afford AI. Vishal also walks through the Series B, why raising twice in one year is a good sign and not a bad one, and growth to more than 300 agencies, including about 30 of the top 100 brokers. Joanna, who ran operations for an independent agency in Texas before joining Outmarket, makes the case for judging AI tools on level of impact, explains why a general tool like Claude struggles with the repeatability that coverage work demands, and gives her best change management advice: put the naysayers in the trial. Scott asks the question every HawkSoft user wants answered, and Anshu explains how Outmarket connects to the AMS instead of trying to replace it. Then Scott asks how long until a customer's data goes straight into the Travelers portal and comes back as a quote. Anshu tells him it will not happen like magic anytime soon, which Scott takes as good news for his career. Alpesh closes on why AI may make standardization less necessary, not more, because the value is in personalization. Show Overview 00:00 Cold open and sponsors 01:02 Welcome, and the incomparable Bradley Flowers 01:49 The beach, the dog, and the 2010 SEC Championship 03:37 180 agency processes and procedures put into AI 04:39 Introducing the Outmarket team 06:20 How a text from Bradley became Outmarket Lite 07:13 Outmarket Lite at about $1,000 a year 07:53 Why raising twice in one year is a good sign 08:31 From seed round to Series A to Series B 09:59 More than 300 agencies and 30 of the top 100 brokers 10:33 Is the source of truth moving out of the AMS? 11:16 The work was always happening outside the AMS 11:59 Proposals and quote comparisons in minutes, not hours 13:32 A shout out to Joanna's husband 14:26 You're in it too deep: where does an agency even start? 15:54 Joanna's path from claims to agency operations 16:31 Level of impact, and avoiding the tool spiral 17:19 Why a general AI misses the nuance in a policy 18:28 Repeatability, consistency and accuracy 19:06 From 4 workflows to more than 40 19:36 Black helicopters, and where your data goes 19:44 Meeting agencies where they are, and how people stay independent 20:14 Who keeps up with the newest models? 20:48 Dual monitors, and the policy checker who does not trust AI 21:45 Save the 26 minutes, then read what it gives you 22:24 Treat it like a new hire, and change management pro tips 23:23 Put the naysayers in the trial 23:56 Sitting with the account manager who will not touch it 25:04 HawkSoft, and when thoughtful turns into stalling 26:08 The AMS as one source of data among many 26:53 Connectors to AMSs, Salesforce and HubSpot 27:58 We don't want to be your next AMS 28:19 How long until AI quotes straight into the carrier portal? 29:57 Not like magic anytime soon 30:10 No standards, and a broker of data in between 31:35 Six months to a year: the producer's bird's eye view 32:05 Scott's backup plan: HVAC school 32:55 Experienced coders, experienced agents, and talking to AI 33:55 Can you connect Claude Teams to Outmarket? 34:33 Outmarket Lite and the agent who would build it themselves 35:16 Taking price out of the equation 36:46 Personalization at scale, and no going back to PVC pipes 37:36 Claude is the electricity, Outmarket is the appliance 38:41 Things have never moved this fast in insurance 39:50 Rewards come from action, and the sign off

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.

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.

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.

In this episode, Scott Howell and Bradley Flowers welcome fractional sales leader Patrick McClure to share proven strategies for doubling insurance agency revenue. After a light-hearted introduction featuring Bradley’s humorous “Insurance Soup” story, Patrick discusses his journey from Clemson football to building a successful career in insurance. He outlines his effective onboarding process, emphasizes how to run high-impact sales meetings with targeted deal strategy and role-playing, and highlights the transformative value of a fractional sales leader. Packed with practical leadership insights, this conversation delivers actionable tactics for agency growth and sales excellence.

In this episode of The Insurance Guys Podcast, Scott and Bradley sit down with Seth Zaremba, CEO of B Atomic, to discuss how his innovative platform is revolutionizing insurance agency operations. Seth shares the evolution of Be Atomic and its Service Center, which standardizes core processes, automates routine tasks, and dramatically boosts efficiency. The conversation explores how agencies are reducing manual workloads, increasing CSR capacity, and streamlining endorsements and remarketing through smart automation and data connectivity. Discover a practical hybrid approach that combines AI with human expertise to cut costs and improve agency performance. Seth also outlines how to get started and offers listeners a special promo code for an exclusive F1 experience. Tune in to learn how this technology is helping agents move from paperwork panic to policy perfection.

In this unfiltered conversation with Scott Howell, Bradley unpacks the 17 things he found broken in his agency after a month away, introduces the “Client Concierge” role he borrowed from Billy Wagner that’s reshaping how Portal Insurance handles quoting and producer development. Scott brings his own takeaway from the Paradiso Mastermind — a 15-minute weekly employee check-in — and both hosts get real about soft market struggles, summer scheduling with kids, and knowing when to cut your losses on the wrong hire.

In this episode of The Insurance Guys, hosts Scott and Bradley kick things off with some lighthearted Southern banter about accents before welcoming Ryne Ring, Director of Gig Economy and Embedded Products at The Citadel, a program administrator specializing in embedded insurance solutions. The conversation explores the evolving role of AI in insurance, from its potential to cover emerging risks to cautionary tales of agents misusing the technology and losing contracts, while diving deep into embedded insurance models. Ryne shares insights on how these products integrate seamlessly into customer journeys, from popular travel insurance in Japan and innovative jewelry programs like BriteCo’s appraisal tools to master policies covering thousands of gig economy workers on platforms connecting independent contractors for tasks like cleaning or lawn care. The discussion highlights practical opportunities for agents to participate through custom programs for rental equipment, tenant liability, and more, emphasizing benefits like consistency, customization, and stronger client relationships rather than being sidelined. Personal stories add warmth, including Ryne’s college-era diner management adventure, chaotic first days in the industry, and a memorable recruiter lunch at Taco Bell, alongside reflections on the industry’s endless learning curve and the strategic use of AI in HR and hiring. The episode wraps with ways to connect with Ryne on LinkedIn and Twitter, offering valuable takeaways for insurance professionals navigating the gig economy and embedded opportunities.

In this episode of The Insurance Guys Podcast, Scott Howell and Bradley Flowers welcome Michael Lebor and Kayden Stephens from Momentum AMP to discuss how artificial intelligence is transforming agency management systems. The conversation traces the evolution of Momentum from its early days as NowCerts through its development into a fully integrated, conversational platform designed to be keyboard free. Guests explore the inevitability of AI in insurance, its role as a superpower for agents, and practical applications such as natural language automation workflows and the advanced AI agent known as Momentum Claw. They also cover carrier adoption of AI, the acquisition of TrustedChoice.com for enhanced digital market access and referrals, and an open agnostic approach that integrates with any tool to benefit agents. The episode includes a live demonstration of an AI voice assistant handling complex policy questions in real time, offering actionable insights for professionals ready to embrace the future of insurance technology.

In this episode of The Insurance Guys, Scott Howell and Bradley Flowers dive into the greatest challenges facing high-risk insurance markets and the complexities of agent classification. Scott kicks things off with a humorous take on insuring strip clubs under a fictional Death Machine Insurance agency built for high-hazard risks, sharing an insightful anecdote about the Las Vegas strip club business model where dancers pay a nightly door fee to work. The conversation then turns serious as Scott recounts his agency's frustrating experiences with 1099 independent contractors in the property and casualty space and why that model often falls short. Bradley breaks down the IRS guidelines for determining 1099 status through behavioral control, financial control, and the type of relationship, while Scott shares how his attempt to revise contractor terms resulted in an immediate departure. The hosts also critique a Vanderbilt University study alleging widespread insurance overcharging, voice concerns about potential federal interference in P&C insurance, and highlight the massive costs of carrier advertising. Responding to a listener question, they address the legal boundaries for using unlicensed virtual assistants in an agency and strongly recommend consulting the state's Department of Insurance or a compliance law firm to ensure full clarity and avoid regulatory pitfalls.

In this insightful episode of The Insurance Guys Podcast, Scott Howell and Bradley Flowers sit down with Kasey D’Amato to explore how emotional intelligence (EQ) is becoming a game-changing leadership skill in the insurance industry. Rather than focusing solely on traditional sales tactics, this conversation dives deep into building scalable businesses, leading with emotional intelligence, navigating difficult conversations, and creating high-performing, trust-based team cultures. Whether you’re a solo producer or running a growing agency, this episode offers practical strategies for playing the long game in insurance.

Scott Howell and Bradley Flowers welcome Ty Robben, a seasoned casualty insurance expert with roots at Great American and Palomar Specialty, for a warm and insightful conversation that mixes engaging personal stories with forward thinking industry analysis. Ty shares his memorable White House internship blunder of spilling toner across the East Wing carpet and his love for Pepperdine's stunning Pacific overlook campus before the group explores the current state of the casualty market, including the transition out of the hard market, persistent challenges in habitational and auto lines fueled by social inflation, and the growing role of AI in transforming underwriting efficiency. Ty opens up about building his own AI powered platform on nights and weekends to better handle complex risks, sparking lively talk on disrupting the MGA and wholesale space, the real value of skilled intermediaries, the drag of legacy technology and slow invoicing, and the future shaped by market cycles, potential government intervention, and the pressing need for tort reform. Thoughtful, optimistic, and thoroughly human, this episode offers a smart look at both the challenges and exciting opportunities ahead in casualty underwriting.

In this episode of the Insurance Guys podcast, host Scott Howell is joined by Kabir Syed and Bradley Flowers to explore how artificial intelligence is reshaping the insurance industry. They discuss AI's impact on agency management systems, workflow automation, and evolving employee roles. Through real-world examples, the guests highlight efficiency gains while cautioning against blind reliance on automation. They advise agencies to embrace AI tools proactively, maintain data ownership, and foster a culture of experimentation. The overarching message is clear: AI won't replace the human relationships central to insurance, but agencies that fail to adapt risk being left behind. Bullet Points - Impact of artificial intelligence (AI) on the insurance industry - Transformation of agency management systems (AMS) through AI - Challenges and opportunities presented by AI integration - Importance of human relationships and trust in the insurance business - Automation of routine tasks and its effect on employee roles - Predictions for the evolution of traditional roles in insurance agencies - Embracing AI tools and fostering a culture of experimentation - Integration of AI with existing AMS platforms and the challenges faced by legacy systems - Efficiency gains and cost reductions associated with AI technology - Practical advice for insurance agencies on starting small and augmenting human judgment with AI

In this episode of the Insurance Guys podcast, hosts Scott Howell and Bradley Flowers welcome Anshu Jain and Vishal Sankhla, co-founders of Outmarket AI. Drawing on their experience at Meta, Uber, and IBM, the duo built an AI platform helping insurance agents analyze policies, compare quotes, and appeal claim denials. Scott and Bradley share real-world success stories from using the tool in their agencies. The founders also announce a $17 million Series A funding round. The episode highlights how AI is transforming insurance, empowering agents to focus on advisory roles while improving efficiency and client outcomes. Bullet Points - Introduction to Out Market AI as a technology platform for insurance agents. - Discussion of the positive experiences of insurance agents using Outmarket AI. - Backgrounds of the co-founders and their previous work in technology and insurance. - Insights on how lessons from major tech companies apply to the insurance industry. - Explanation of how Out Market AI analyzes insurance policies, claims, and quotes. - Features of Out Market AI, including customizable workflows and accuracy in data analysis. - Real-world examples of how Out Market AI has helped agents with claims and policy comparisons. - The potential impact of AI on the future of the insurance industry. - Recent funding news and plans for scaling the company. - Information on how insurance agents can learn more about and access Outmarket AI.

In this episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers dive into the rapid evolution of artificial intelligence in the insurance industry, joined by recurring guest CJ Hutsenpiller. The trio discuss how AI, specifically tools like Claude and ChatGPT, are transforming agency operations, from streamlining workflows to integrating with agency management systems. They highlight tangible use cases such as automating prospecting, remarketing analysis, and calculating true costs of service. The hosts also address the challenges legacy management systems face in keeping up with new AI capabilities and urge agencies to embrace these advances to stay competitive. They touch on market trends, including advertising in the insuretech space and current agency buying and selling climates, noting the impact of rate cycles. The episode wraps up with practical advice on how insurance professionals can start leveraging AI by simply asking the tools for implementation instructions, and emphasizes that taking action is key to staying relevant in a rapidly changing landscape. Show Overview 00:00 Gaining advertisers during COVID 05:55 Encouraging product trial for listeners 09:23 Mastermind event in Phoenix 11:08 Preparing an AI presentation 16:29 Explaining efficient policy updates 18:51 Using CLAUDE for daily prospecting 21:18 Legacy insuretechs evolving with APIs 26:00 Challenges in buying home insurance 27:05 AI enhancing online insurance buying 33:01 AI-driven premium adjustment tool 34:32 Tracking service costs with Claude 38:15 Using AI tools for learning 41:18 AI fear affecting agency owners 45:23 Timing insurance sales in hard market 47:55 Podcast closing and contact info

In this episode of the Insurance Guys podcast, host Scott Howell and co-host Bradley Flowers sit down with Kevin Panter, a 37-year insurance industry veteran and president of Kevin Panter Insurance. Kevin shares insights on transitioning from captive to independent agencies, emphasizing ethics and proper preparation. He discusses building community involvement as a volunteer firefighter and EMT, growing his agency network SNA, and mentoring his children entering the business. Kevin offers advice for agents feeling stuck, stressing self-investment, continuous education, and community engagement as keys to long-term success. Bullet Points - Transitioning from captive to independent insurance agencies - The importance of community involvement and personal branding - Experiences and stories from the insurance industry - Advice for new agents and those considering a career in insurance - The role of ethics in the insurance profession - The significance of networking and collaboration among agencies - Family dynamics and legacy in the insurance business - Strategies for agency growth and overcoming stagnation - The impact of personal investment in community relationships - Insights on industry challenges and opportunities for agents

In this episode of The Insurance Guys Podcast, hosts Scott Howell and Bradley Flowers welcome Max from Novella to discuss trends and challenges in the insurance industry. The conversation covers wholesaler processes, the evolving role of brokers, and the impact of technology and surplus lines on the market. Max shares insights from his time at Lemonade and his journey founding Novella. The episode features industry anecdotes, including a humorous story about Bradley dropping his visitor badge in a toilet at Progressive HQ, and highlights the importance of relationships and adaptability in insurance. Bullet Points - Personal anecdotes and humorous stories related to the insurance industry. - Introduction and background of a new participant, Max, and his company, Novella. - Examination of the relationship between retail brokers and wholesalers. - Challenges faced by new entrants in the wholesaler market. - The evolving landscape of insurance technology and its implications. - Trends in property and casualty insurance, particularly regarding surplus lines. - The importance of independent brokers in providing tailored insurance solutions.

In this episode of the Insurance Guys Podcast, host Scott Howell is joined by Kelly and Bradley Flowers for a lively discussion on the shifting insurance market and effective account manager compensation. The group explores strategies for navigating a soft market, emphasizes the importance of client retention, and shares insights on agency leadership, training, and culture.. The episode blends practical advice with humor and candid reflections on the realities of running a successful insurance agency. Bullet Points - Current state of the insurance market, focusing on the transition from a hard market to a soft market. - Implications of market changes for insurance agents and agencies. - Importance of client retention and effective communication in a competitive market. - Challenges faced by agencies in managing client relationships and remarketing strategies. - The significance of product knowledge among agents and its impact on client interactions. - Leadership dynamics within insurance agencies and the need for clear hierarchy and accountability. - Strategies for optimizing existing business and improving retention rates. - The importance of proactive prospecting and maintaining a growth mindset in agency operations.

In this episode of The Insurance Guys Podcast, host Scott Howell and Bradley Flowers interview Hunter Nelson, who started his own insurance agency at just 18. He shares his unconventional journey, from door-knocking for leads in high school to specializing in trucking insurance. The discussion covers challenges of being a young agent, fraud prevention, strategic hiring, and the importance of grit and continual learning. Bradley and Scott swap stories about client service, underwriting, and managing risk, offering practical advice for agency growth. The episode is both insightful and inspiring, highlighting innovation and determination in the insurance industry. Bullet Points - The journey of a young insurance agency owner who started at 18 years old. - The importance of customer experience and exceptional service in the insurance industry. - Strategies for recruiting and hiring experienced agents from other agencies. - Challenges faced by young agents in a traditionally older industry. - The significance of networking and involvement in industry organizations for securing carrier appointments. - The impact of fraud in the trucking insurance sector and the importance of secure certificate issuance. - Underwriting practices and client selection criteria for trucking insurance. - Financial risk management related to commission chargebacks in insurance policies. - The role of talent and team culture in accelerating business growth. - The importance of persistence and grit in overcoming challenges in the insurance business.

In this episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers sit down with Mick Hunt, visionary business leader and host of the Mick Unplugged podcast, to discuss how insurance agencies can leverage technology and AI to modernize, streamline operations, and stay competitive. The conversation dives deep into building custom tools, rethinking traditional agency management systems, and why usage-based pricing is changing the insurtech landscape. Mick shares insights from high-profile podcast guests, the importance of “skin in the game” consulting, and practical ways agencies can utilize AI for prospecting, sales, and efficiency. The hosts and Mick tackle the myth of AI replacing insurance agents, emphasizing that while AI will enhance productivity and alter hiring patterns, the advisory role will remain crucial, if agents continue to up their game. From advice on balancing video and audio branding to stories about using AI for negotiation and workflow automation, this episode is packed with actionable takeaways for forward-thinking insurance professionals. Tune in to hear how building your own tools and embracing innovation can help your agency thrive in the age of AI. Show Overview 00:00 Podcast introduction and host welcome 04:52 Highlighting Mick's podcast journey 07:05 Starting the podcast journey 11:56 Changing the consulting model 13:57 Growing an AI brand with podcast 16:18 Impact of modern AI trends 19:40 AI's shift to usage-based pricing 24:18 Confidence in product and pricing 28:04 Using AI for lead research 31:47 Cold calling versus cold outreach 34:28 Using AI for business efficiency 36:49 How agents handle carrier issues 41:15 Tech layoffs blamed on AI 42:42 AI streamlining insurance processes

In this episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers welcome Chris Huebner, 2025 Agent of the Year, to discuss innovative strategies for building referral partnerships in insurance. They share insights on moving beyond traditional marketing, leveraging social media, hosting educational events, and creating personalized client experiences. The conversation highlights the power of thoughtful, individualized gestures over generic gifts, and offers practical tips for agents to deepen relationships with clients and referral partners, ultimately driving business growth in a competitive industry. The episode blends humor, real-world examples, and actionable advice. Bullet Points - Recognition of Chris Huebner as the 2025 Agent of the Year by the Insurance Journal. - Strategies for building effective referral partnerships in the insurance business. - The shift from traditional marketing tactics to developing referral partnerships. - Innovative approaches to providing continuing education (CE) classes for realtors. - Importance of personalized marketing and thoughtful gift-giving to strengthen client relationships. - Engagement tactics for networking and building familiarity with referral partners. - The role of follow-up communication in converting leads into referral partners. - Insights on creating memorable experiences and differentiating oneself in a competitive market.

In this episode of the Insurance Guys Podcast, host Scott Howell welcomes Bradley Flowers and Michael Weaver for a lively discussion on insurance agency management and innovation. Bradley shares stories about Mardi Gras in Mobile and agency life, while Michael details the growth of Agency Coach AI, an AI-powered sales coaching platform for insurance agents. The conversation explores how AI-driven role play, call analysis, and flexible service platforms are transforming sales training, operational efficiency, and customer engagement, highlighting the importance of data-driven strategies and ethical, customer-friendly business models in the evolving insurance industry. Episode Highlights - The introduction and development of Agency Coach AI, an AI-driven coaching platform for insurance agents. - The benefits of AI technology in sales training, including real-time feedback and role-play simulations. - Common challenges faced by insurance producers in sales conversations and how to overcome them. - The importance of rapport building and effective communication in closing sales. - The economic considerations and pricing models for AI software in the insurance industry. - The integration of AI tools with existing phone systems and their impact on agency management. - The contrast between traditional sales training methods and innovative AI-driven approaches. - The ethical considerations of contract practices in the insurance technology space.

In this episode of the Insurance Guys Podcast, hosts Scott Howell and Bradley Flowers are joined by marketing expert Chris Langille to discuss the realities of AI, ChatGPT, and digital marketing for insurance agents. Blending humor with practical advice, they debunk common myths about AI-driven search, highlight the continued importance of Google and social media, and share actionable strategies for building an effective online presence. The conversation also covers generational shifts in search habits, the pros and cons of various ad platforms, and the value of embracing new marketing channels alongside proven fundamentals. What The Guys Cover: - Introduction of the main guest and his diverse professional background. - Examination of the hype and misconceptions surrounding ChatGPT and AI. - Comparison of ChatGPT and Google in terms of search behavior and market share. - Insights into user intent and the effectiveness of different marketing platforms. - Emphasis on the importance of social media and video content for insurance marketing. - Analysis of advertising strategies, including the advantages of Facebook Ads over Google Ads. - Recommendations for budget allocation in marketing and the role of SEO. - Encouragement for insurance agents to leverage younger generations' digital skills and community engagement

In this episode of the Insurance Guys Podcast, host Scott Howell and guest Corey Fischer, General Manager for Agency Distribution at Progressive Insurance, discuss Progressive’s approach to balancing direct and agency channels, insurance pricing, and leveraging technology like telematics and AI. Joined by Bradley Flowers and another contributor, they explore market trends, agency partnerships, and Progressive’s efforts to innovate in auto and property insurance. The conversation highlights the importance of transparency, strong carrier-agent relationships, and adapting to industry changes, offering practical insights for insurance professionals navigating a rapidly evolving marketplace. Episode Highlights - Discussion on the role of independent agents versus direct sales in insurance distribution. - Insights into Progressive Insurance's business model and premium distribution. - Examination of pricing strategies and market competitiveness in different regions. - Exploration of telematics and its impact on insurance rating and customer behavior. - Challenges and opportunities related to autonomous vehicles and their insurance implications. - The importance of technology and data analytics in pricing and underwriting. - Strategies for agency partnerships and enhancing agent relationships. - Overview of Progressive's growth initiatives in various insurance segments. - The significance of company culture and core values in driving innovation and success. - Addressing common misconceptions about pricing differences between direct and agency channels.

In this episode, hosts Bradley Flowers and Scott Howell interview Stacy Korsgaden, candidate for California Insurance Commissioner. The discussion explores the challenges facing California’s insurance market, including overregulation, limited carrier options, and the strained FAIR Plan. Stacy shares her industry experience and outlines her plans to attract new insurers, embrace innovation, and improve consumer education and disaster response. The conversation highlights the importance of informed leadership, the impact of regulatory decisions, and the need for reform to restore a healthy, competitive insurance environment for Californians. Show Overview - Overview of California's insurance market challenges - Discussion on the candidacy of Stacy Course Gordon for California Insurance Commissioner - Impact of overregulation and Proposition 103 on insurance pricing and availability - Importance of real-world insurance experience in leadership roles - The role of the Department of Insurance in regulating and supporting the market - Strategies for attracting new insurance companies to California - The significance of consumer education regarding insurance processes and expectations - Examination of the FAIR Plan and its implications for the insurance market - Insights on the relationship between insurance agents and market dynamics - The need for innovative solutions and technology in addressing insurance issues in California

In this live episode of The Insurance Guys Podcast, hosts Scott Howell and Bradley Flowers engage with the Young Agents of IIAG. They discuss pressing challenges such as legislative changes, tort reform, and market dynamics, with insights from guest John Barbour. The conversation covers the impact of litigation, coalition-building for political influence, and recent legal reforms in Georgia. The hosts blend humor, personal stories, and expert advice, encouraging agents to stay informed, proactive, and united as they navigate the evolving insurance landscape. The episode closes with a motivating call to leadership and community engagement. Highlights: - Live podcast recording at a recent insurance industry conference - Engagement with independent insurance agents and professionals - Discussion of industry insights and challenges - Legislative updates affecting the insurance sector - Importance of coalition-building among insurance agents - Impact of tort reform on the insurance market - Role of independent agents in the legislative process - Cultural challenges and public distrust in the insurance industry - Strategies for navigating complex insurance regulations - Encouragement for agents to take proactive steps in their businesses and communities

In this episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers welcome Sam Louwrens, a young and refreshingly candid commercial insurance producer, for a lively discussion on the future of insurance, especially how to make it more appealing to Gen Z. Bradley Flowers kicks things off with a passionate rant about common misconceptions and bad advice that frustrate agency owners in online forums. The trio then explores why insurance is often misunderstood and underappreciated, tackling topics like industry mediocrity, the value insurance brings to society, and how the sector could attract innovative young talent. Sam shares his journey into insurance, emphasizing the appeal of residual income, flexibility, and creative opportunities for newcomers. The conversation candidly critiques tech disruptors, industry hype about AI, and highlights strategies for competing in the commercial space. If you’re interested in honest insights, humor, and advice on staying consistent in the insurance world, this episode is a must-listen!

In this episode, Bradley and Scott sit down with Will Hall from Game Point Capital, an agency that is playing a unique role in college sports during the NIL era.

In this episode, Scott takes us through his recent health scares and what he is doing to come back from the brink.

In this episode of the Insurance Guys Podcast, hosts Scott Howell and Bradley Flowers sit down with legendary agent Von Mueller, who shares his expertise on selling life insurance, annuities, and health policies at a remarkable volume, all while working just eight months a year. Von Mueller dives deep into the power of asking thoughtful, engaging questions as a tool to generate appointments and build genuine client relationships, stressing that listening and genuine interest are far more effective than simply dispensing information. He lays out actionable strategies for agents to overcome the struggle of getting in front of prospects, suggesting a “practice over study” approach and a formula for crafting compelling questions across different age groups. Key takeaways include leveraging your property & casualty book of business, using strategic questions to spark deeper conversations, and focusing on helping clients avoid financial pitfalls such as taxes and inflation. Von Mueller also offers details about his training resources for agents eager to take their sales skills to the next level.

In this episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers talk with Matthew Vega-Sanz, CEO and founder of Gail, about how AI is changing the insurance industry. Matthew shares his story, starting with a car-sharing app for college students, then building Lula, a top insurtech company, and now working on Gail, an AI platform focused on insurance and financial services.They talk about why insurance agencies need AI built for their field, share real examples of how agents can work more efficiently, and discuss why data privacy matters when using AI. Matthew explains how Gail’s voice-powered AI agents handle calls and how its custom insurance “GPT” keeps data safe and accurate. The episode also covers how many agencies are using these tools, tips for getting started, and special offers for listeners who want to try Gail. If you want to see how AI can make your agency run better and more securely, this episode is worth a listen.

On this episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers welcome the always insightful and entertaining David Carothers. The trio dives into practical strategies for insurance agents, focusing on personal and agency branding, leveraging technology for efficiency, and the importance of sticking to your lane within specialized markets. David Carothers shares the story behind his new sales book, co-authored with his son, offering daily sales wisdom and a forthcoming podcast expansion. He gives tactical advice for handling out-of-state insurance opportunities, especially in states like Florida, highlighting critical underwriting and policy nuances. The group also discusses automation tools for agencies and innovative lead-gen tactics, revealing how David Carothers generated 500 paid leads in 30 days using AI-optimized Meta ads. The episode closes with updates on The Protege competition, the need for more diversity in the insurance industry, and tips on building a resilient, well-rounded agency. Expect a balance of actionable advice, candid industry talk, and plenty of banter!

In this engaging episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers welcome back Becca Rubenfeld, co-founder of Anchor Watch, to discuss the evolving landscape of crypto insurance, specifically insuring Bitcoin assets. The conversation covers real-world scenarios, including a story of $160,000 in stolen Bitcoin and the challenges of recovering crypto after theft. Becca Rubenfeld breaks down common crypto scams, the latest tactics in cybercrime, and how Anchor Watch’s unique custody and insurance solutions can offer both technical and traditional protections. The trio also explores how insurance brokers can now partner with Anchor Watch through a new broker program and highlights the growing need for specialty crypto coverage for both individuals and commercial clients. With the rise of institutional money and changes in market dynamics, this episode is a must-listen for agents interested in entering the crypto insurance space. Becca Rubenfeld also shares updates from recent industry conferences, making this a timely conversation on a cutting-edge insurance niche.

On this episode, Scott Howell and Bradley Flowers welcome Shelby Tirado and Chris Huebener from Brightway Insurance in Jacksonville, FL. The crew explores the agency’s impressive operations, including a high-volume new business model that writes about $1 million in new premium each month and has a network of over 600 referral partners. Shelby Tirado and Chris Huebener share insights from their restaurant industry backgrounds that translate into insurance success, such as multitasking, energy, and customer service. The episode covers Brightway’s unique approach to onboarding, producer development, and referral partner management, all fueling their strong growth. They discuss strategies for staying top-of-mind with referral sources, adapting in a tough Florida market, and why hiring outside the insurance industry can be a game-changer. Whether you want to scale your agency or refine your process, this episode is packed with actionable wisdom from top performers.

On this episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers welcome David Watson, partner at Mappus Insurance Agency and founder of Risk Advisor. The conversation starts with laughs about wild car stories, lost SD cards, and minivan mishaps. The discussion then moves to the core topic, which is bringing technology-driven efficiency to personal lines insurance. David shares the evolution of Risk Advisor, a digital intake and AI-powered underwriting platform that was built to streamline and standardize the quoting process for independent agencies. He explains how the platform helps agents quickly identify qualified carriers, avoid wasted time, and reduce errors. This, in turn, makes agency operations more consistent and data-driven.The hosts discuss software integration, data management, and the business model behind Risk Advisor, including pricing and the absence of long-term contracts. The episode also offers candid insights into industry frustrations, such as difficult data vendors, and ends with actionable advice for listeners who are looking to modernize their agencies.A must-listen for agents seeking practical tech solutions to boost profitability while keeping the fun in the business.

On this episode of the Insurance Guys Podcast, hosts Scott Howell and Bradley Flowers sit down with Jeff Wingate, President at Rate Insurance, for a deep dive into the realities of building a top 100 insurance agency through organic growth—not mergers and acquisitions. Jeff Wingate shares Rate’s journey from relying almost entirely on mortgage-generated leads to creating a scalable, tech-driven, virtual organization sourcing business nationwide. The conversation uncovers the advantages and challenges of proprietary technology, integrating APIs with carriers and mortgage partners, and the long runway of hiring and training licensed agents. The trio also gets candid about industry cycles, consumer patience, AI’s impact on agency operations, and cross-selling strategies for bundling auto and home. With honest discussions about setbacks and wins, this episode is packed with lessons for agency owners seeking to grow smart in a changing market.

On this episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers welcome master storyteller and branding expert Neal Foard. Drawing from decades of shaping global brands like Toyota and Budweiser, Neil Ford shares practical insights on how storytelling can transform an insurance business, elevate client relationships, and create long-lasting impressions. The conversation covers why human connection and authenticity matter more than ever in today’s AI- and automation-driven world, and how small gestures, like handwritten notes and genuine kindness, make brands stand out. Neal Foard also offers actionable storytelling techniques insurance professionals can implement immediately, and highlights his Storyfire course for those serious about perfecting this essential skill. The hosts and Neil Ford swap personal stories that illustrate the power of storytelling not just in sales but in everyday life. If you want to grow your agency, connect more deeply with clients, and communicate your value, this episode delivers inspiration and tactical advice.