On Episode 129 of the Agent Boost Podcast, Dan and Mike sit down with Tyler Rees and Josh Benson, longtime friends and business partners who built one of the fastest growing Medicare FMOs in the country before selling it to Humana.

Tyler and Josh trace their path back to central Pennsylvania, where they started out selling final expense insurance door to door, eventually founding Innovative Financial Group (IFG), scaling it to over $125 million in final expense premium and $300 million in annuities, then pivoting hard into Medicare in 2020. That pivot took them from 4,500 apps their first AEP to more than 25,000 the next year, and eventually to an 18 month acquisition process that ended with Humana buying the company in 2022.

The second half of the conversation shifts to what Tyler and Josh are building now: EnrollHere, an insurance technology platform designed to solve the industry's biggest blind spot, siloed data and a total lack of accountability in lead generation and marketing. They break down how EnrollHere's call control and compliance scoring tools have helped partners cut cost per acquisition in half, why they see themselves as a neutral "Switzerland" in the distribution world rather than a competitor, and the audit framework they're building to finally hold publishers and marketers to the same standard agents and agencies already face.

They also get into the mechanics most people never see: how hierarchy actually works when one agent reports to multiple upline agencies, why lifetime value varies so wildly between partners, and why they believe cracking Medicare Advantage is the hardest and most valuable problem in the industry to solve. It's a candid look at building, selling, and rebuilding in a space that rewards the operators willing to actually understand the data.

***Chapters***

00:00 Welcome & Introducing Tyler Rees and Josh Benson

01:19 Childhood Friends Turned Business Partners in Insurance

04:58 Splitting Paths - Corporate Detour vs. Going Independent

06:03 The Cold-Call Trick That Built a 400-Agent Team

09:17 Founding IFG and Buying Out the Business11:33 The Pivot to Medicare & a Massive First AEP

14:35 The Call From Humana & an 18-Month Diligence Process

17:31 Scaling Post-Acquisition, the Walmart Deal & Stepping Away

23:56 Why They Built EnrollHere - Solving Insurance's Data Problem

28:51 Staying "Switzerland" & Building the MVP With Niko and Tim

34:06 The Call Center Breakthrough - Cutting CPAs in Half

38:08 Why Data Beats Gut Feel on Lead Quality

40:01 The Marketing Accountability Gap in Medicare

44:02 Spoofed Numbers, Dupe Routing & Bad Actor Tactics

48:01 Building a Compliance Audit Standard for Publishers

53:08 Is Telesales Dead? Why Phone Enrollment Still Matters

54:23 Shared Visibility & the End of "Pay and Pray"

59:43 What the Lifetime Value Data Actually Shows

1:02:12 Beyond Medicare - ACA, Final Expense & Attachment Rates

1:06:22 Cracking Hierarchy - EnrollHere's Core Advantage & Wrap Up

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On Episode 128 of the Agent Boost Podcast, Mike sits down with longtime agent and agency owner Riley Garner for a conversation that starts personal and ends up being a masterclass in why experience, both lived and professional, is what actually builds trust in healthcare.

Riley opens up about his son's sudden health crisis: a routine day swimming in the Virgin River turned into E. coli, then Shiga toxin, then HUS, then dialysis at Primary Children's Hospital. As a licensed agent himself, Riley walks through what it's actually like to be on the other side of the desk, dealing with ACA coverage through Molina, life flight bills, a denied ambulance claim, and the appeals process, and how even industry veterans get surprised by their own EOBs.

It's a real time case study in why insurance gets a bad rap until the day you actually need it, and why agents who've lived through a claim fight understand something no training manual can teach.

From there, the episode traces Riley's full arc in the business: Chick fil A to personal trainer to a last minute Medicare license earned three days before the deadline, into Connection Point, then Go Health during the 700 enrollments a season era, through the Covid era collapse of the big box telesales shops, and into the hybrid field and digital model that Dan and Mike built out of that chaos. Riley became a team lead, grew the WellCare book, moved to Tampa to build out that market, and has now come full circle, opening his own agency, Health Plan Assistance, in St. George, Utah, combining phone, virtual, and face to face enrollment under one roof.

Mike and Riley make the case that this hybrid, trust first model is exactly where the industry is headed, and Riley's path is a live example of what building it the right way looks like.

If you're an agent thinking about going independent, opening a physical office, or just want a real story about what insurance means when it's your own family on the line, this episode is essential listening.

**Chapters**

00:00 Welcome & Introducing Riley Garner

02:15 Riley's Son's Health Crisis: E. coli, HUS & Primary Children's Hospital

05:11 Riley's Own ACA Coverage and the Molina Bills

10:21 Why Even Agents Struggle to Understand Their Own EOBs

12:40 Chick fil A, Meeting His Wife & Getting Licensed in 3 Days

16:04 Utah as a Medicare Call Center Hub & the Old War Hero Era

19:34 How Big Box Telesales Went Off the Rails

24:13 The Two Types of Telesales Agents & Becoming a Team Lead

26:55 Growing the WellCare Team & Moving to Tampa

30:14 Building Health Plan Assistance in St. George

33:08 Why Face to Face Is Making a Comeback

36:42 Riley's 5 Year Vision & How to Reach Him

40:34 Wrap Up

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In Episode 127 of the Agent Boost Podcast, Dan and Mike open with a "week of survival" tone. AEP certifications are dropping, the agent force is demoralized, and the industry feels like it's in a constant state of flux. On a lighter note, both of their sons got licensed this week, a small but meaningful signal that the business still has a future for those who approach it the right way.

The centerpiece of this episode is a raw, unfiltered breakdown of why the telesales model in Medicare is dying, and why it's happening from three directions at once. Regulatory pressure has systematically outlawed nearly every outbound marketing mechanism, leaving consumer-generated inbound calls as the last legal lane. Even that lane is compromised, as lead generators routinely run unapproved URLs behind a single CMS-submitted site, meaning almost none of them are truly compliant. The 1-to-1 marketing rules that were supposed to clean up the industry have instead choked off the lead supply entirely.

Carriers are finishing the job. They've made clear they prefer local, field-written business over phone enrollments, and they're backing it up with 100% call audits on telesales, requiring human review (not AI), and forcing agencies to write up agents even when the consumer never complained. It's a Salem witch trial environment, and field agents are held to zero equivalent standard. The agents getting burned are often the best ones left, the ones who survived 4+ years without a termination, while 2.5 to 4.5 million Medicare Advantage members are expected to be displaced this AEP with fewer and fewer agents available to help them.

Dan and Mike also make a strong case for why FMV commissions are actually a bargain for carriers. When you pay an agent, you're not just paying for a sale. You're paying for acquisition, ongoing customer service, and retention, all bundled into one nominal fee. Carriers cutting brokers out of the equation will have to replace all three components with internal infrastructure, and they won't save money doing it.

The episode closes with a timely breakdown of the Walmart retail program for 2027, covering tiered A/B/C stores, first right of refusal for agents in good standing, and cost-sharing through FMOs. Both hosts are bullish on retail as the landing spot for displaced telesales agents, and they urge agents not to wait until September. Stores will be gone before AEP kicks off.

If you're a telesales agent wondering where to land this cycle, an agency owner trying to understand why the economics stopped making sense, or a field agent who wants to know what the carriers are actually thinking, this episode is essential listening.

***Chapters***

00:00 Welcome & Week of Survival — Both Sons Get Licensed

01:09 The State of the Industry Going Into AEP Certifications

04:29 Why Everything Is Changing Faster Than Ever Before

07:29 Telesales Is Dead — Setting Up the Core Argument

09:55 How 1-to-1 Marketing Rules Choked Off the Lead Supply

13:21 The Lead Generator Problem — Noncompliant URLs and the Washing Machine

19:51 The Economics of Telesales Are Broken — CPA vs. LTV Explained

24:54 "The Juice Isn't Worth the Squeeze" — The Math No One Wants to Do

27:52 Carriers Don't Want the Business — And They're Showing It

33:31 Salem Witch Trials — Carrier Crackdowns on Phone Enrollments

38:16 Carriers Are Turtling — What That Means for Distribution

41:14 The Warning for Displaced Telesales Agents — There's Nowhere Left to Hop

42:05 War Hero or War Criminal? Why 700 Enrollments Is No Longer a Badge of Honor

43:34 The FMV Argument — What Carriers Actually Get for That Commission

49:40 Walmart 2027 — Tiers, First Right of Refusal, and the Retail Opportunity

57:27 Wrap Up & Final Thoughts