Episodes

How Travis Hedge Built an AI-Enabled Brokerage at Vouch Insurance
June 18, 2026

How Travis Hedge Built an AI-Enabled Brokerage at Vouch Insurance

Callan Harrington sits down with Travis Hedge, Co-Founder and CEO at Vouch Insurance, to explore how his company became an AI-enabled brokerage generating 73 NPS scores and $200M+ in funding. The conversation dives into Vouch...

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How Scott Tannas Turned One Small-Town Agency into a $775M Exit
June 11, 2026

How Scott Tannas Turned One Small-Town Agency into a $775M Exit

Host Callan Harrington sits down with Scott Tannas, Chairman of Western Investment Company and Canadian Senator, to explore how he transformed a single small-town insurance agency into a massive enterprise. Scott shares the r...

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Chad King's M&A Strategy That Grew King Risk Partners to $125 Million
June 4, 2026

Chad King's M&A Strategy That Grew King Risk Partners to $125 Million

Host Callan Harrington sits down with Chad King, Chairman and Founder of King Risk Partners, to explore how he transformed a 6-person family agency into a $125 million powerhouse with over 600 employees. Chad shares the pivot...

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How Rollo Insurance 5X'd in 5 Years Without a Niche or Outside Capital
May 28, 2026

How Rollo Insurance 5X'd in 5 Years Without a Niche or Outside Capital

Callan Harrington sits down with Jackson Rollo, President of Rollo Insurance, to explore how he became president at 24 and led the agency through 5x growth over 5 years without private equity backing. Jackson explains Rollo's...

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How Brokers Can Become True Risk Advisors with Aclaimant President David Wald
May 21, 2026

How Brokers Can Become True Risk Advisors with Aclaimant President Da…

Callan Harrington sits down with David Wald, President and Co-Founder of Aclaimant, to explore what it truly means to become a risk advisor in today's insurance market. David shares the unexpected origin story of Aclaimant an...

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Chris Paradiso's Retention System Every Insurance Agency Needs
May 14, 2026

Chris Paradiso's Retention System Every Insurance Agency Needs

Host Callan Harrington sits down with Chris Paradiso, owner of Paradiso Financial and Insurance Services, to dive into the retention strategies that form the foundation of real agency growth. Chris shares how his 50+ employee...

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How Lyndon Block Built 7 Insurance Brokerages Through Community Building
May 7, 2026

How Lyndon Block Built 7 Insurance Brokerages Through Community Build…

Callan Harrington sits down with Lyndon Block, President & CEO of Block's Agencies, Prairie Insurance, Mello Insurance, and Rosthern Agencies, to explore his unconventional path to building 7 insurance brokerages across Saska...

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How Curtis Barton Built Alkeme into a $2B Insurance Powerhouse
April 30, 2026

How Curtis Barton Built Alkeme into a $2B Insurance Powerhouse

Curtis Barton didn't take the traditional path to building a large platform agency. He convinced six agency owners to merge their businesses, raise private equity capital together, and build something that had never been done...

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Breaking Down Modern Claims Operations with Snapsheet President Andy Cohen
April 23, 2026

Breaking Down Modern Claims Operations with Snapsheet President Andy …

Callan Harrington sits down with Andy Cohen, President and COO of Snapsheet, to dive into why claims operations represent the biggest opportunity left in insurance, and what it actually looks like when carriers get it right. ...

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What Top Insurance Producers Do Differently with Paul VanderMarck
April 16, 2026

What Top Insurance Producers Do Differently with Paul VanderMarck

Host Callan Harrington sits down with Paul VanderMarck, Chief Technology and Innovation Officer at SageSure, to explore what the best insurance producers actually do differently, and why a softening market is about to make th...

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Kyle Nakatsuji on What the Future of AI in Insurance Actually Looks Like
April 2, 2026

Kyle Nakatsuji on What the Future of AI in Insurance Actually Looks L…

Host Callan Harrington sits down with Kyle Nakatsuji, CEO and Founder of Clearcover and Dearborn Labs, to explore how AI is reshaping insurance from the ground up. Kyle shares his unconventional path from persistent business ...

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How Matt Naimoli Built a Referral Network with 1300 Custom Bobbleheads
March 26, 2026

How Matt Naimoli Built a Referral Network with 1300 Custom Bobbleheads

Matt Naimoli went from college baseball player to building one of the fastest-growing insurance agencies in America using an unconventional $10,000 bobblehead campaign. What started as a networking attempt became a systematic...

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Jim Waterwash's Playbook for Retaining Clients After an Agency Acquisition
March 20, 2026

Jim Waterwash's Playbook for Retaining Clients After an Agency Acquis…

Host Callan Harrington sits down with Jim Waterwash, Partner at INSocial Risk Advisors, to get into the details behind their 90%+ retention rate across 5 agency acquisitions, as well as the hard lessons that got them there. J...

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How Jeff Snyder Built Matic to 750K Leads Through Loan Servicing Partnerships
March 12, 2026

How Jeff Snyder Built Matic to 750K Leads Through Loan Servicing Part…

Callan Harrington sits down with Jeff Snyder, President of Matic, to break down how an “unqualified” first employee built one of the most successful embedded insurance platforms in the mortgage servicing space. Jeff shares th...

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How Eric Roberts Built the Cross-Sell System Behind His $20M Agency
Feb. 26, 2026

How Eric Roberts Built the Cross-Sell System Behind His $20M Agency

Callan Harrington sits down with Eric Roberts, owner of My Insurance Group, to break down the systematic approach behind building a $20 million agency that generates 270 new inbound leads monthly without any cold calling. Eri...

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How Eddie Knezevich Built a Lead Machine Through Continuing Education Webinars
Feb. 19, 2026

How Eddie Knezevich Built a Lead Machine Through Continuing Education…

Callan Harrington sits down with Eddie Knezevich, President & CEO of NLF Partners, to break down the continuing education lead generation system that transformed his wealth management practice. Eddie shares how he built a mac...

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How Patrick McBride Built an Insurance Agency Targeting Harley Davidson Owners
Feb. 12, 2026

How Patrick McBride Built an Insurance Agency Targeting Harley Davids…

Host Callan Harrington sits down with Patrick McBride, founder of The McBride Agency, to explore his unconventional approach to building a successful independent insurance agency. Patrick shares how he transformed his persona...

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How Andy Harbut Scaled a Niche Insurance Brokerage in One Year
Feb. 5, 2026

How Andy Harbut Scaled a Niche Insurance Brokerage in One Year

Callan Harrington sits down with Andy Harbut, Co-Founder of NewCo Risk, who built a multi-million dollar insurance brokerage in just one year after leaving the big brokerage world. Andy shares how he and his partner, Josh, ca...

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Jennie Lyttle's Cold Calling Playbook for Insurtech Outbound Success
Jan. 15, 2026

Jennie Lyttle's Cold Calling Playbook for Insurtech Outbound Success

Callan Harrington sits down with Jennie Lyttle, Sales Director at Salt and one of the most skilled cold callers in insurtech. Jennie breaks down her most successful campaign ever, the “broker box” initiative at Beam Benefits ...

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Clinton Houck's Framework for Driving Non-Core Product Adoption
Jan. 8, 2026

Clinton Houck's Framework for Driving Non-Core Product Adoption

Callan Harrington sits down with Clinton Houck, VP of Insurance and Distribution at Fair, to explore how to successfully drive adoption of non-core products within P&C insurance agencies. Clinton brings serious insurance expe...

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How Caleb Cramer Used Webinars to Scale AgencyZoom to Thousands
Dec. 18, 2025

How Caleb Cramer Used Webinars to Scale AgencyZoom to Thousands

Callan Harrington sits down with Caleb Cramer, Chief Revenue Officer at LAUNCH, to break down the exact group demo process that helped AgencyZoom onboard thousands of agencies to their CRM product. Caleb shares his experience...

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The Story Behind one of Nationwide's Most Successful Marketing Campaigns with Brad Barnett
Dec. 11, 2025

The Story Behind one of Nationwide's Most Successful Marketing Campai…

Callan Harrington sits down with Brad Barnett, former VP of Enterprise Marketing at Nationwide and current independent consultant, to break down one of insurance marketing's most successful campaigns. Brad managed over $300 m...

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Inside the Strategic Shift Coming to Insurance in 2026 with Callan Harrington
Dec. 4, 2025

Inside the Strategic Shift Coming to Insurance in 2026 with Callan Ha…

Host Callan Harrington breaks down why the insurance industry may be entering a new growth phase and shares a standout story from his Bold Penguin days that proves what’s possible when momentum shifts. With enterprise carrier...

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How Nick Golubitsky Uses AI and RevOps to Transform GTM
Nov. 13, 2025

How Nick Golubitsky Uses AI and RevOps to Transform GTM

Callan Harrington sits down with Nick Golubitsky, VP of Revenue Operations at GreenSlate, for a deep dive into how AI is actually being used in go-to-market today. Nick brings over 8 years of revenue operations experience acr...

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