The Reagan RedZone

Episode 21 - AI Overreactions, Beachfront Real Estate, and Valuations

Wed, 01 Apr 2026 10:00:00 -0400

Join us on the 21st episode of the Reagan RedZone as Webb Milward, Kevin Stipe and Brian Deitz discuss AI disruptions in the industry, public and private broker valuations, and the value of owning the client relationship.

Episode 20 - Going For It on Fourth Down

Tue, 03 Feb 2026 10:00:00 -0400

In this episode of The Reagan RedZone, Mark Crites and Webb Milward are joined by Jon Loftin of the MJ Companies to discuss what it takes for a top privately held firm to remain competitive and thrive.

Episode 19 - 2025: She's a Beaut, Clark

Tue, 09 Dec 2025 09:30:00 -0400

In this final Reagan RedZone episode of the year, Webb Milward, Brian McNeely, and Harrison Brooks recap key trends from 2025, share strategies brokers should focus on as we head into a new year, and make predictions for what we'll see in 2026.

Episode 18 - Joel Wood on Industry Trends and Blackberry Phones

Fri, 24 Oct 2025 10:00:00 -0400

In this episode of The Reagan RedZone, Webb Milward and Brian Deitz are joined by the President & CEO of The Council of Insurance Agents & Brokers, Joel Wood, to discuss key takeaways from the CIAB's annual insurance leadership forum at the Broadmoor. Specifically, their conversation focuses on M&A trends, talent movement, and the impact of AI on the insurance industry.

Episode 17 - Late Night Omelets, Higher Valuations, and a Job Well Done

Tue, 16 Sep 2025 08:30:00 -0400

Join us for the seventeenth episode of The Reagan RedZone, a podcast that explores key trends, takeaways, and insights for the insurance distribution industry.

In this episode, Tom Doran, Kevin Stipe, and Webb Milward reflect on the evolution of the Best Practices Study over the years, the importance of benchmarking your agency's performance, and future predictions for the industry.

Episode 16 - Look At Me Now: The 2025 Top 100 List

Tue, 22 Jul 2025 10:00:00 -0400

In this episode of the Reagan RedZone, Mark Crites, Kevin Stipe, and Webb Milward look back at how the Business Insurance Top 100 Insurance Brokers list has evolved, break down the biggest takeaways from the 2025 rankings, and share what it all means for insurance brokers navigating today’s market.

Episode 15 - Market Update: When Siblings Finally Agree

Mon, 16 Jun 2025 10:00:00 -0400

In this episode of The Reagan RedZone, Webb Milward is joined by Brian Deitz and Brian McNeely for a mid-year check-in and a deep dive into the current state of the insurance mergers and acquisitions (M&A) market. Their discussion explores the number of announced deals this year, the impact of recent mega-deals, the current rate environment, and what this could mean for brokers in the months ahead.

Episode 14 - We're Still Standing

Tue, 20 May 2025 10:00:00 -0400

Join us as Bobby Reagan, Harrison Brooks, and Webb Milward reflect on events that have shaped their careers, the resiliency of the insurance distribution industry over the last 50 years, and how brokers can best position themselves to face future challenges.

Episode 13 - Tariffs, Ross Perot, and Ferris Bueller

Tue, 15 Apr 2025 10:00:00 -0400

Welcome back to the Reagan RedZone, a podcast that explores key trends, takeaways, and insights for the insurance distribution industry.

Join us on our latest episode as Brian Deitz, Brian McNeely, and Webb Milward discuss the current situation with tariffs, the economy, and the potential impact on the privately held insurance broker.

As mentioned in the episode, if you are interested in participating in our Growth & Profitability Survey, please email benjamin@reaganconsulting.com.

Episode 12 - Chuck E. Cheese and the Valuation Gap

Tue, 18 Mar 2025 10:00:00 -0400

Tune into this month's episode with Tom Doran, Mark Crites, and Webb Milward as they discuss the current state of insurance broker valuations, focusing on the differences between internal and external valuations. Their conversation highlights the challenges of size insecurity in the industry, the critical role of talent recruitment in ensuring agency growth and success, and how an up-to-date perpetuation strategy can tackle both.

Episode 11 - Hot Takes With Hot Grandpa

Thu, 13 Feb 2025 10:00:00 -0400

Tune in to the latest episode of the Reagan RedZone, where Kevin Stipe, Harrison Brooks, and Webb Milward share their insights on what privately held firms should expect in 2025, the top opportunities they can capitalize on, and the key areas to focus on for success.

Episode 10 - Lessons in Authentic Leadership with Paul Hering

Tue, 21 Jan 2025 11:00:00 -0400

The new year is here, and the Reagan RedZone is back in action! Join us for our first episode of 2025 as Bobby Reagan and Webb Milward are joined by esteemed guest Paul Hering, recently retired Vice Chairman of Marsh McLennan Agency. In this episode, Paul reflects on his outstanding career in the insurance industry and shares pivotal lessons he learned as an authentic leader.

To learn more about Reagan Consulting, visit www.reaganconsulting.com.

Episode 9 - Big Deals, Bold Predictions, and BMX Bikes

Tue, 17 Dec 2024 12:30:00 -0400

It's time for the final Reagan RedZone episode of 2024!

In this episode, Brian Deitz and Brian McNeely, Reagan Consulting Partners, and Webb Milward, Head of Strategic Development at Reagan, discuss three massive deals that happened this year, organic growth predictions, and what they would focus on in 2025 if they were a private insurance broker. As a bonus, listen to find out what their favorite childhood Christmas gift was.

To learn more about Reagan Consulting, visit reaganconsulting.com, and to sign up for GPS, visit reaganconsulting.com/gps-sign-up.

Episode 8 - Can't Keep the Good Brokers Down

Tue, 12 Nov 2024 10:15:00 -0400

We are back with the eighth episode of the Reagan RedZone! Listen in as Harrison Brooks and Mark Crites, Reagan Consulting Partners, join Webb Milward, Head of Strategic Development at Reagan, to dive into the current state of the insurance brokerage industry, assess Q3 2024 GPS performance, and discuss their perspectives on 2024 growth and market trends.

To learn more about Reagan Consulting, visit reaganconsulting.com, and to sign up for GPS, visit reaganconsulting.com/gps-sign-up.

Episode 7 - Election Impact with CIAB President & CEO, Joel Wood

Thu, 07 Nov 2024 11:00:00 -0400

Welcome to the seventh episode of the Reagan RedZone. Join us for a special election edition as CIAB President & CEO, Joel Wood, sits down with Reagan Consulting CEO, Kevin Stipe, and Head of Strategic Development, Webb Milward, to discuss how the election results will impact the insurance brokerage industry.

To learn more about Reagan Consulting, visit reaganconsulting.com.

Episode 6 - The Golden Era Turns Bronze

Thu, 15 Aug 2024 10:00:00 -0400

Welcome to the sixth episode of the Reagan RedZone. Join us as Reagan Consulting CEO, Kevin Stipe, Partner, Tom Doran, and Head of Strategic Development, Webb Milward, sit down to recap the state of insurance brokerage, assess Q2 2024 GPS performance, and discuss their perspectives on 2024 growth and market trends.

If you have any questions about our Growth & Profitability Survey, please reach out to Logan Brown at logan@reaganconsulting.com.

To sign up to participate in GPS, visit https://www.reaganconsulting.com/gps-sign-up.

To learn more about Reagan Consulting, visit reaganconsulting.com.

Episode 5 - Wake Up Call?

Thu, 30 May 2024 10:00:00 -0400

Welcome back to the fifth episode of the Reagan RedZone. Join us as Reagan Consulting Executive Chairman, Bobby Reagan, President, Brian Deitz, and Head of Strategic Development, Webb Milward, sit down to recap the state of insurance brokerage, assess Q1 2024 GPS performance, and discuss their perspectives on 2024 growth and market trends.

To learn more about Reagan Consulting, visit reaganconsulting.com, and to sign up for GPS, visit https://www.reaganconsulting.com/gps-sign-up

Episode 4 - Live from the Reagan Summit: Predictions for 2024

Tue, 07 May 2024 10:00:00 -0400

Join us on the Reagan RedZone, featuring Mike Victorson, CEO of M3 Insurance, for the first live recording from the 2024 Reagan Summit conference. Listen as Webb Milward, Kevin Stipe, Brian McNeely, and Mike review the predictions made during the 2022 Summit and debate their predictions for what the next 2 years have in store for Insurance Brokers and Agents.

Episode 3 - Knock, Knock. Who's there? Institutional Investors.

Tue, 16 Apr 2024 10:00:00 -0400

Join us on the Reagan RedZone as we recap Reagan Consulting's 2024 Insurance Investor-Connect Conference with Reagan Partner, Harrison Brooks, Partner, Mark Crites, and Head of Strategic Development, Webb Milward.

To learn more about Reagan Consulting, visit reaganconsulting.com, and to sign up for GPS, visit https://www.reaganconsulting.com/gps-sign-up.

Episode 2 - Will the Optimists Prevail?

Thu, 29 Feb 2024 08:00:00 -0400

Welcome back to the second episode of the Reagan RedZone. Join us as Reagan Consulting Executive Chairman, Bobby Reagan, President, Brian Deitz, EVP and Partner, Brian McNeely, and Head of Strategic Development, Webb Milward sit down to recap the state of insurance brokerage and discuss their perspective on 2024 growth and market trends.

To learn more about Reagan Consulting, visit reaganconsulting.com, and to sign up for GPS, visit https://www.reaganconsulting.com/gps-sign-up

Episode 1 - The Other 40%

Thu, 14 Dec 2023 08:00:00 -0400

Welcome to the first episode of the Reagan RedZone. Join us as Reagan Consulting CEO, Kevin Stipe, Partner, Harrison Brooks, and Head of Strategic Development, Webb Milward sit down to discuss their unique take on the state of insurance brokerage and their bold predictions for 2024.

Sign up for GPS - https://www.reaganconsulting.com/gps-sign-up

Kaiser Family Foundation health benefits survey - https://www.kff.org/health-costs/report/2023-employer-health-benefits-survey/

Producer Recruiting & Development Tool - https://cld.bz/JznN0Pe

The Reagan RedZone Trailer

Wed, 13 Dec 2023 01:30:00 -0400

Welcome to The Reagan RedZone! From Reagan Consulting, we are excited to bring you a new podcast to dive into insurance distribution industry key trends, takeaways, and insights.

Click here to learn more about Reagan Consulting: https://www.reaganconsulting.com/