S1E5: When Growth Starts Stealing From Your Family with Ben Glass

As Chase Calhoun went from buying a foreclosure sight unseen to running a real estate and construction operation with more than 130 units under management, the pressure didn’t stem from a lack of opportunity; it came from becoming the bottleneck in the business. Capital constraints, scattered responsibilities, market cycles, and the need to hire before he felt ready forced him to confront the limits of doing too much himself. You’ll hear how Chase is learning to simplify the work, delegate real ownership, build systems from painful experience, and turn a founder-led hustle into a business that can scale beyond him.

As Paul TenHaken built a thriving digital agency and later became mayor of Sioux Falls, the outside story looked like momentum, influence, and achievement. But underneath it lay cash flow panic, purpose stagnation, and the weight of stepping into public leadership. A meaningful conversation with his wife, a political smear days before an election, and the uncertainty of leading through COVID forced him to confront what leadership costs when the money, reputation, and answers are no longer guaranteed. You’ll hear how Paul moved from success to significance, learned to lead without control, and rebuilt his view of work around calling, community, and the greater good.

Botanie Soap had grown from a tiny kitchen-based soap operation into Montana’s largest natural soap manufacturer, but behind that growth was a founder carrying too many seats and a wife who never expected to lead the company without him. Then Tim was diagnosed with an aggressive cancer and gone within weeks, leaving Lindsay Joss Iudicello to face grief, motherhood, ownership, and a 25-person company she once only touched part-time. You’ll hear how Lindsay chose to grow instead of freeze, leaned on the structure already built through EOS, and learned to lead the business forward without becoming the founder she lost.