Episodes

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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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Feb. 20, 2025

The Ethics of AI, Digital Likenesses, and the Future of Content Creat…

In this episode of That Worked , host Callan Harrington and comedian/content creator Sullivan Finlay dive into the rapidly evolving role of AI in entertainment, content creation, and brand collaborations. They explore the eth...

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Feb. 13, 2025

Focusing on Insurance: Why Specialization Changes Everything

Callan Harrington, Founder of FlashGrowth and host of That Worked , takes a deep dive into the strategic decision to niche his business into the insurance space. In this solo episode, he breaks down the fears, challenges, and...

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Feb. 6, 2025

The Power of Niching Down, Adding Instant Value, and Vulnerability in…

In this episode of That Worked , host Callan Harrington and co-host Sullivan Finlay, a writer, comedian, and content creator, dive into the challenges and opportunities of building a career in the evolving digital landscape. ...

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Jan. 30, 2025

Sriya Maram - Co-Founder of Persana AI: The Modern GTM Stack, Prompt …

Sriya is the Co-Founder of Persana AI. Persana AI is a Y-Combinator-backed AI tool designed to enhance sales through hyper-personalization, seamless integration, and united workflows. Prior to Persana AI, Sriya was a Product ...

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Jan. 23, 2025

Scott Knowles - Co-Founder and CEO of Deep Vector: Empathy in Sales, …

Scott Knowles is the Co-Founder and CEO of Deep Vector, a web-based software platform that transforms unstructured documents into actionable insights with speed and precision. Prior to Deep Vector, Scott was the Founder and C...

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Jan. 16, 2025

Dan Snyder - CEO & Co-Founder of Lower: Launching a B2C Line, Growth …

In this episode, you’ll learn: How to adapt from a B2B to B2C mindset. When to acquire externally versus build internally. How an entrepreneurial culture empowers high performers. How to grow market share in a down market thr...

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Jan. 9, 2025

Tom Grote - CEO of Agape Automation: Narrowing your Focus, Stong Valu…

In this episode, you’ll learn: How narrowing in on what you’re really good grows profits. The value of seeking out educational opportunities later in life. How to maintain balance between operational excellence and innovation...

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Dec. 19, 2024

David McFarland - Founder and CEO of Coterie Insurance: Building the …

David McFarland is the Founder and CEO of Coterie Insurance. Coterie Insurance puts insurance agents and brokers first, delivering instant business insurance across the United States. Since 2018, Coterie has raised over $100M...

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