Episodes

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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Why Ryan Hanley Says Every Insurance Leader Needs a Personal Brand
Nov. 6, 2025

Why Ryan Hanley Says Every Insurance Leader Needs a Personal Brand

Host Callan Harrington sits down with Ryan Hanley, President of Linqura and one of the insurance industry's most recognized voices, to break down the content strategy that built his personal brand over 20 years. Ryan shares h...

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Why Insurtech Companies Are Losing the Messaging Battle with Callan Harrington
Oct. 30, 2025

Why Insurtech Companies Are Losing the Messaging Battle with Callan H…

Callan Harrington returns from ITC Vegas with a critical observation that every insurtech needs to hear. Despite increased capital flowing into the market and genuine excitement around new technology, decision makers are comp...

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Why Margeaux Giles Spent a Year Rebranding Her Startup
Oct. 23, 2025

Why Margeaux Giles Spent a Year Rebranding Her Startup

Callan Harrington sits down with Margeaux Giles, CEO of IRYS Insurtech, to break down their year-long rebranding process that transformed both their external presence and internal culture. Margeaux shares why rebranding felt ...

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Alex Harris on Building Partnerships That Drive Revenue and Mutual Benefit
Oct. 16, 2025

Alex Harris on Building Partnerships That Drive Revenue and Mutual Be…

Callan Harrington sits down with Alex Harris, co-founder of Fiat Growth and Fiat Ventures, to unpack how great partnerships actually drive growth. Alex shares the story of bringing together two major players in insurance, Lem...

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Go-to-Market Benchmarks Every Insurance Leader Must Know with Callan Harrington
Oct. 9, 2025

Go-to-Market Benchmarks Every Insurance Leader Must Know with Callan …

Callan Harrington breaks down the evolving go-to-market landscape for insurtech companies, sharing insights from his presentation at InsureTech New York's Education Day. As founder of Flashgrowth, Callan examines what's staye...

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How Chris Kessler Built Multi-Million Dollar Insurance Partnerships
Oct. 2, 2025

How Chris Kessler Built Multi-Million Dollar Insurance Partnerships

Host Callan Harrington sits down with Chris Kessler, Chief Product and Platform Officer at Bold Penguin, for an in-depth look at enterprise solution selling. Chris brings a unique background in strategy consulting that has di...

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How Ido Deutsch is Using Paid Media to Acquire Insurance Agencies at Scale
Sept. 25, 2025

How Ido Deutsch is Using Paid Media to Acquire Insurance Agencies at …

Callan Harrington sits down with Ido Deutsch, VP of Growth at Agentero, to break down one of the most successful (and shocking) paid media strategies for acquiring insurance agencies. Ido shares how he built a predictable and...

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How Amber Wuollet Repositioned an Insurance Product and Hit Sales Goals 2x Faster
Sept. 18, 2025

How Amber Wuollet Repositioned an Insurance Product and Hit Sales Goa…

Callan Harrington sits down with Amber Wuollet, Director of Product & Lifecycle Marketing at Cowbell, to explore how thoughtful marketing can change the trajectory of an insurance product. After years of lackluster performanc...

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Closing the Chapter: From That Worked to The Insurance Growth Lab
July 29, 2025

Closing the Chapter: From That Worked to The Insurance Growth Lab

Callan Harrington, Founder of Flashgrowth and host of That Worked , reflects on the journey of his podcast as he records its final episode before shifting to The Insurance Growth Lab. In this solo episode, he dives into the o...

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Matt Farrell - COO at Niobium Microsystems: Succeeding in the Earliest Stages, Evaluating Potential Employees, and Creating Work/Life Alignment
March 13, 2025

Matt Farrell - COO at Niobium Microsystems: Succeeding in the Earlies…

Matt Farrell is the COO at Niobium Microsystems, a trusted hardware design company developing high-performance microelectronic components to enable the secure collection, processing, and distribution of critical data. Matt is...

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Mastering Content Strategy, Delegation, and Creative Efficiency
March 6, 2025

Mastering Content Strategy, Delegation, and Creative Efficiency

In this episode of That Worked , co-hosts Callan Harrington and Sullivan Finlay dive into content strategy, delegation, and maximizing creative output. Sullivan shares how structured planning has transformed his workflow, the...

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The Power of Improv, AI-Driven Content, and Buying Back Time for Growth
Feb. 27, 2025

The Power of Improv, AI-Driven Content, and Buying Back Time for Grow…

In this episode of That Worked, host Callan Harrington and comedian/content creator Sullivan Finlay explore how improv can transform leadership, the evolving landscape of AI-driven content creation, and why outsourcing is ess...

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