Wealthyist E75: From One Truck To Gen Two: Building a Life—and a Business—Outdoors with Bret Achtenhagen

Kent Halleen, wealth manager for Annex Private Client, sits down with Bret Achtenhagen, president and CEO of Seasonal Services, the Wisconsin landscaping firm he launched in 1994 with a truck, a tractor, and a newly announced first child on the way. Brett walks through that first $70,000 year, the farm-kid love of dirt and seasons that pulled him out of an office, and 32 years of steady growth built on natural stone, time in clients’ kitchens, and outdoor spaces people actually use. The conversation turns to the harder work now underway: shifting from founder to second generation as his 31-year-old son begins to take over—what the next generation wants the company to become, and how to pass a family business without breaking the family. Halleen draws the parallel to wealth planning: tax, gifting versus buyouts, estate design, and the cost of leaving concentrated “plants” unpruned. Along the way they cover the firm’s process (motivation first, then design and budget), decades-long client relationships that now include the kids’ homes, and current high-end demand—wellness courtyards, year-round pavilions, and synthetic turf that still serves a deeper brief: get families off screens and back outside.