Episodes

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 million in annual media spend and a $50 million portfolio of sports and entertainment partnerships during his 20-year tenure at Nationwide. He was instrumental in developing the iconic NFL partnership featuring Peyton Manning and the return of the famous "Nationwide is on you...

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 spend up 27% and major players like Nationwide committing $1.5 billion to tech, all signs point to a market ready to get back on offense. In this episode, Callan unpacks what it really takes to capitalize on that kind of opportunity. He explains how the Bold Penguin team h...

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 across multiple insurtech companies and shares real campaigns and tools he's implementing right now. This conversation cuts through the AI hype to focus on practical applications that are driving results. Nick walks through a live enterprise lead campaign using multiple AI too...

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 how he went from nearly being fired by his father-in-law to becoming a sought-after speaker and industry leader through consistent content creation. Ryan explains his unique approach to content development, filtering ideas through leadership topics and insurance applications...

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 completely lost trying to figure out what these companies actually do. When everyone claims to be "the AI company for insurance," the messaging becomes indistinguishable noise. Callan breaks down why this positioning crisis is happening and reveals the massive opportunity it cr...

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 necessary after 3 years of rapid startup growth and how the process became much deeper than choosing new colors and logos. The conversation reveals the unexpected internal benefits of rebranding, from aligning employees on the company mission to dramatically improving conte...

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, Lemonade and Bestow, and transforming that collaboration into a revenue engine, not just a press release. He explains how journey mapping, trigger-based campaigns, and data-driven targeting helped unlock meaningful customer adoption. Along the way, Alex opens up about his vira...

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 stayed the same from 2024 and what's rapidly changing in 2025 as AI transforms sales and marketing strategies. Callan covers critical benchmarks for scaling revenue from zero to 1 million, 1 to 10 million, and beyond 10 million in annual recurring revenue. He explains when to hi...

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 directly shaped how Bold Penguin consistently lands household names as enterprise clients in the insurance space. The conversation centers on Chris's detailed solutioning process, which goes far beyond typical sales approaches. He walks through his methodology of engaging wit...

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 affordable machine generating leads via Facebook. He breaks down the mindset that led him to bet on paid social, the experimentation framework behind his campaigns, and why chasing “more leads” is the wrong strategy. For insurance companies looking to diversify beyond tra...

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 performance, Amber’s team uncovered insights that helped a struggling policy hit its 12-month sales goal in just 6 months, without changing a single feature. The conversation also touches on Amber’s career journey, including lessons from a launch that collided with COVID shutdowns an...

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 origins of the show, what it became, and why now is the right time to focus fully on the insurance space. With stories, founder-inspired lessons, and a glimpse into what’s next, Callan shares the evolution of the podcast. In this episode, you’ll learn: How That Worked began ...

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 a multi-time founder and early-stage executive. Before the startup world, Matt was a coach for the University of Dayton Men’s basketball team and later the Assistant Athletic Director at the University of Dayton. In this episode, you’ll learn: How to create work/life ali...

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 power of visual content boards, and why repurposing content is essential for expanding reach without reinventing the wheel. They also break down the 10-80-10 rule of delegation, an approach to outsourcing that helps creators and entrepreneurs focus on high-impact work. Plus,...

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 essential for scaling creative work. Sully shares improv techniques—such as adaptability and active listening—that boost effectiveness both on stage and in the workplace, while Callan emphasizes the growing importance of human-driven insights in an AI-saturated environment. Tog...

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 ethical dilemmas of AI-generated personas, the impact of deep research tools on competitive analysis, and how AI is reshaping creative industries. Sullivan shares his perspective on balancing creative integrity with AI-driven scalability, the challenges of licensing digital like...

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 long-term benefits of narrowing focus in business. If you’ve ever hesitated to specialize, this episode is packed with insights on how niching down can unlock exponential growth opportunities. In this episode, you’ll learn: The importance of industry expertise for diffe...

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. They explore the vulnerability of content creation, why niching down can accelerate business growth, and how relationship-building plays a crucial role in expanding creative opportunities. Sullivan shares his insights on adapting to industry shifts, while Callan discusses add...

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 Manager at LinkedIn. In this episode, you’ll learn: The value of participating in hackathons. What a modern GTM tech stack looks like. How to develop a ‘prompt engineering’ skill set. How using your own product impacts your product roadmap. How to...

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 CEO of Modgic, a software company that provided workers' compensation and mod analysis tools for the commercial insurance industry and was successfully acquired by Zywave in 2021. In this episode, you’ll learn: The power of narrowing your focus. How innovat...

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 through acquisition. How avoiding over-accommodating a seller in an acquisition leads to long-term success. Follow Dan on LinkedIn Connect Follow Callan on LinkedIn Subscribe to the Newsletter

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. How to build a business grounded in courage, empathy, and doing the right thing. The importance of surrounding yourself with a diverse team with complementary skills. Follow (guest) on LinkedIn Connect Follow Callan on LinkedIn Subscribe to the Newsletter

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 in funding and partnered with over 10,000 insurance agencies and brokerages across the country. Prior to leading Coterie, David was Chief Actuary at Clearcover, a personal auto insurtech startup in Chicago. David is also a Fellow in the Casualty Actuarial Society and ...

Ry Walker is the Founder and CEO of Tembo. Tembo is the Postgres developer platform for building every data service. Their mission is to collapse the database sprawl of the modern data stack with a unified developer platform. Prior to founding Tembo, Ry was the Founder and CEO of Astronomer, which has been a huge success and has raised over 280 million dollars. In this episode, you’ll learn: How to navigate the difficulties of layoffs. The value of selling 5% of your shares du...