Welcome to Founder Real Talk, a podcast for founders, by founders.
We explore the real journey of building and growing a company. Each episode, we go beyond the highlight reel to unpack the strategies, decisions, and hard lessons that shaped successful businesses, revealing the good, the bad, and the ugly behind the growth.
Jeb Dunkelberger is the founder and CEO of Coalition Health Group, an insurance services platform modularizing healthcare functions to make alternative funding accessible to small and mid-sized businesses. After early market demand sparked massive hiring, Jeb faced the painful reality of "startup indigestion"—over-scaling a service team before sales converted. He opens up about executing tough workforce reductions, establishing intentional tension within leadership, and why listening and radical accountability are the ultimate tools for scaling both a business and a life.
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Chapters
(00:00) - Intro
(01:55) - Modularizing insurance for main street employers
(06:40) - Partnering with 18,000 clinical locations
(07:34) - Commercial wins vs. 80% team retention
(09:56) - Startup indigestion and the trap of early hype
(11:40) - The brutal reality of health insurance sales cycles
(16:36) - Conceptual alignment, commitment, contractual
(20:47) - Maintaining team trust through workforce reductions
(26:08) - Building intentional tension in the executive team
(29:07) - Flattening the chain of communication
(32:10) - Stop talking, start listening, serve others
Links & Resources
Referenced in the episode:
Keywords
founders, entrepreneurship, health insurance, Coalition Health Group, self-funding, alternative funding, healthcare startup, sales operations, ICP, startup indigestion, leadership development, workforce reduction, company culture, executive coaching, startup scaling
