Host Levi Te Slaa sits down with Barry Sackett, managing partner and long-time advisor to business owners across the Midwest. Barry traces his path from a family of lawyers to roles as in-house counsel, controller, CFO, and now managing partner. He explains why his work is really about building trust in every transaction—often before legal issues turn into lawsuits.

Barry digs into the realities entrepreneurs face: scaling themselves as the business grows, avoiding “inventor’s disease,” and not snapping back to old roles when growth gets hard (the “rubber band effect”). He also unpacks the shift toward fractional general counsel services, what AI can and can’t do for legal work, and why the Midwest’s lawyer shortage is both a challenge and an opportunity for innovative firms.

You’ll hear a favorite client story that went from humble beginnings to a $60M private equity valuation—and then into meaningful community philanthropy. Throughout, Barry returns to one theme: grit as the through-line of every successful founder.

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