Host - Rory Holland - cstmr.com - Linkedin: CSTMR

Interviewed - Joey Bouchard, QuoteWell

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In This Episode

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. Joey explains the importance of the underdog mindset, the value of choosing applied learning over traditional academia, and why the clearinghouse for risk is ripe for digital transformation. Whether you're interested in insurtech innovation, tactical leadership advice, or the connection between dating and sales Joey’s perspective is well worth a listen.

Key Takeaways

1. The "Human+" Philosophy: Success in insurtech isn't about total automation; it’s about using technology to remove friction so human brokers can focus on high-value relationships.
2. The Underdog Mindset: Joey highlights how his hatred of losing and intense work ethic—honed as a non-Ivy League recruit at Palantir—drive his success at QuoteWell.
3. Solving the Data Gap: QuoteWell was born from the realization that wholesale insurance lacks standardized data, creating a massive opportunity.
4. Wholesale Insurance as a Clearinghouse: Despite being a legacy sector, wholesale brokers facilitate 25% of commercial transactions, making them a critical infrastructure for the economy.
5. The Power of the Caesura: Joey discusses the importance of "taking a beat" or a pause before making major decisions to ensure clarity and strategic alignment.
6. Applied Learning vs. MBA: Joey explains why he chose a hands-on strategy role at Aon to learn the messy reality of insurance instead of pursuing a traditional graduate degree.
7. Mission-Driven Work: Innovation in insurance isn't just about software; it’s about the real-world impact of ensuring businesses can survive catastrophic losses.

Chapters

00:00: Young, and Determined

02:14: Introduction with Rory Holland

03:30: Austin Eateries and Sales Wisdom

08:05: The Hunter Mountain ACL Incident

11:15: The Palantir "Bootcamp" Experience

14:15: Learning Perseverance and Grit

17:45: The Decision to Tackle Insurance

20:45: Five Countries in Five Days

23:30: Niche Expertise as a Career Catalyst

25:30: Growing Up in a Pawn Shop

28:30: The Pawn Shop Bait Counter and Samurai Swords

31:15: A Legacy of Hard Work

34:00: Defining QuoteWell and Wholesale Brokerage

39:15: Building the "First 30"

43:00: Empowering Brokers

44:45: Corporate Consolidation vs. The Collaboration Economy

49:15: Why Mission Matters

53:30: The Ruthless Elimination of Hurry

57:30: Connecting with QuoteWell

58:33 Closing Remarks with Rory Holland