The Insurtech Leadership Podcast

The Insurtech Leadership Podcast•insurtech.podbean.com

Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers. New episodes weekly.

Last refreshed: July 9th, 2025 at 8:24 PM ⓘ

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Episodes

Most People are Really Good People (w/ Cory Isaacson, CEO reThought Insurance)

Cory Isaacson had built ad run several major software businesses and filed 5 Patents before he started ReThought Insurance . This time he sat down with a venture partner and wrote down exactly what he wanted to achieve and the market opportunity that would become ReThought. He hand-picked his co-founders based on their common beliefs and deep subject-matter expertise in insurance. According to Cory, "If you start with a Big Vision and Big Dream you make it a lot longer and more successfully than...

Dec 21, 2020•12 min•Ep. 8

Taking Over as CEO (w/ Jennifer Carroll, CEO Veruna, Inc.)

Jennifer Carroll , CEO at Veruna, Inc , is a Technologist & Attorney based in Austin. She has a unique leadership story. Unlike most Insurtech Founder-CEOs, she was asked by the Board to join in early 2020 when she was strategic advisor on growth plans. Veruna is creating an agency management system for the modern age, access and report on your data, independent brokers and MGAs. Changes she’s brought as new CEO: Prioritizing people to have time with families and moving around during the day...

Dec 14, 2020•9 min•Ep. 7

How to Create AI products with Authentic Demand (w/ Larry Lafferty, CEO Velocity AI Works)

Today's episode is a series of short lessons on applying AI to Insurtech from software veteran Larry Lafferty . Veloxiti deploys a genius business model strategy, where they start with AI for Dept. of Defense to produce the R&D and first versions of products, then moves them to a separate company that commercializes and productizes the AI tech into the various vertical use cases like Insurance. 4 Critical Lessons for any SaaS Software business in 2021: 🚣🏽‍♂️AI Is Software: Media does us a ...

Dec 08, 2020•9 min•Season 1Ep. 6

The Billion-Dollar Micro-Insurance Opportunity (w/ Dr. Kyshun Webster, CEO Compassion Society Benefits)

Meet Dr. Kyshun Webster, CEO of Compassion Society Benefits, who is bringing a new diversity of ideas & perspectives to change insurance. His MGA focuses on creating new insurance models around the growing demands of 21st century families. Dr. Webster is driven by his upbringing as a New Orleans native who grew up in single-parent home, where he learned at a young age the need to address the wage loss for family care-givers. In his own words, "We bring together digital natives, industry vete...

Dec 01, 2020•13 min•Season 1Ep. 5

Why to Get People Excited About What You're Doing (w/ Ian Jeffrey, CEO Breathe Life)

How different is building a business in Canada versus the Valley or New York? Today's episode with Ian Jeffrey, Founder & CEO at Breath Life tells a story of relishing these different perspectives: Competition for Talent and Money Sure there's more talent and investors in the valley, but the competition for those resources is fierce, Try retaining that deep experienced talent in the valley when they realize you're not the next Facebook, versus Building a business with people who are attracte...

Nov 24, 2020•13 min•Season 1Ep. 4

People Committed to the Cause vs. Employees (w/ Anurag Shah, CEO Aureus Analytics)

Today's episode features Anurag Shah, CEO Aureus Analytics. Before raising his $5m Series A, he moved his family to the US and shifted the entire focus onto Insurance: "The whole industry is based on data, but data was just being neglected." 🤸🏽‍♂️On Corporate Resiliency and Engagement: “We’ve always found more value in people more committed to the cause, rather than looking at their past experience or educational qualifications. People who are willing to give you their best time and energy wit...

Nov 06, 2020•8 min•Season 1Ep. 3

Why Real Leaders Listen to Their People (w/ Max Drucker, CEO of {Carpe Data)

As a leader, how do you do something meaningful an authentic with Diversity & Inclusion? Rather than doing some empty letter to shareholders, Max Drucker went deep in 2020 with his employees and realized quickly that more diverse ideas will make his company better. So he has fundamentally re-mapped the way his company creates roles and hires people. Four key lessons in today’s 12-minute podcast: 🔀 How to Hard Pivot your company when the landscape shifts 🔫 How to be transparent with employe...

Oct 22, 2020•13 min•Season 1Ep. 2

Taking My Company Remote (w/ Phil Reynolds, CEO of BriteCore)

The incredibly dynamic Phil Reynolds, CEO Britecore , founded the one of the world’s first and most successful core insurance platforms. From Silicon Valley, right? No, from Missouri . . Today’s guest built a team, a product, and helped shape what was to become Insurtech. This incredibly dynamic leader sets the standard for being ahead of the trends, global entrepreneurship, and just genuinely being a thoughtful leader. . Today you can learn how to hire the most talented engineers on a global sc...

Oct 08, 2020•13 min•Season 1Ep. 1

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