CSTMR

In this episode, Rory Holland sits down with Chris Levy, President and CEO of Pursuit, a mission-driven community development financial institution (CDFI). Chris shares his remarkable homegrown journey, rising from a summer intern to the head of the organization in just over a decade.

In this episode, host Rory Holland sits down with Levi King, the serial entrepreneur and visionary behind Nav. Levi’s story is a masterclass in building a mission-driven brand, starting with the deeply personal pact he made to secure the Nav.com domain to honor a small business legacy. The conversation moves far beyond typical fintech metrics, diving into the “brutal” 360-degree feedback exercise that transformed Levi from a boss into a leader at age 26.

In this episode of Mighty Finsights, host Rory Holland sits down with Joey Bouchard, Founder and CEO of QuoteWell, to discuss the modernization of the wholesale insurance industry. Joey shares his journey from the high-stakes environment of Palantir to solving the Gordian Knot of insurance quoting. They explore the Human+ model—a philosophy that uses technology to empower brokers rather than replace them.

Join Rory Holland and a panel of CSTMR specialists—Jack Macy, Brendan Bresnahan, and Romina Gomez—for a deep dive into the world of digital discovery. As AI tools like ChatGPT and Google’s AI Overviews challenge conventional search tactics, financial brands must shift to a mindset that expands brand visibility across digital channels.

In episode 31 of Mighty Finsights, Rory Holland interviews Mike Nellis, CEO of the Austin Community Foundation (ACF), about the pivotal role of community foundations in today’s economy and philanthropic landscape. Mike discusses how ACF serves as a “charitable bank” and community endowment, connecting people and resources to tackle issues like housing affordability. They explore the generational wealth transfer and the skepticism younger generations hold toward traditional philanthropy.

For many business and marketing leaders, the realization that your marketing team is understaffed or underskilled happens naturally. It may happen gradually, but having more work than people to do it is a fact that can’t be ignored for long. Deciding how to fix the imbalance of tasks and talent is another challenge entirely. Cut the work? Unlikely. Hire more staff? Too many internal factors at play. Partner with a marketing agency?

The way people search, discover, and engage with information is changing fast. GenAI tools like ChatGPT and Google’s AI Overview are becoming go-to resources for quick answers—reducing clicks and rewriting the rules of online visibility, especially for fintech and financial services firms. Even when users start with a search engine, they’re often served AI-generated summaries instead of traditional link lists.

Join us for Episode 30 where host Rory Holland sits down with Jason Henrichs, CEO at Alloy Labs and co-host of the #1 global fintech podcast, Breaking Banks. They dive into Jason’s journey, from co-founding Perk Street, an early concept of Banking as a Service (BaaS), to leading community bank innovation at Alloy Labs. They explore the critical role of trust in building financial brands, especially in today’s environment.

In a free-market economy, growth may be the most widely accepted, and commonly held goal for businesses. The path to achieving growth is less obvious. This explains why there is an endlessly growing literature on the subject. For companies in the fintech and financial services space, sometimes the path to growth gets reduced to a simplistic formula: more advertising + more budget + better tech = growth. That approach is incomplete.

At CSTMR, we love original content. If done correctly,it builds authority, showcases expertise, and delivers real and long-lasting value. But compelling original content takes time, resources, and subject matter depth across multiple channels and departments. For many of us (marketers, small business owners, startup founders, etc.), especially those with lean teams or tight timelines, keeping up with that demand is a challenge.