The UpFlip Podcast

239. 3 Hard Truths About Running a $5M Contracting Business

May 18, 2026·27 min
Episode Description from the Publisher

Steve Griggs transforms backyards into multimillion-dollar outdoor experiences. After 40 years in the landscaping industry, Steve has built a $5M/year design firm catering to high-net-worth clients—including lawyers, investors, athletes, and celebrities.In this episode, Steve sits down with Ryan Atkinson to share the gritty reality of scaling a premium service business. From trimming bushes with his union-worker father in New York to starring on Bravo's Backyard Envy and authoring a best-selling book, Steve knows exactly what it takes to command top-tier prices. He explains why trying to be "good at everything" is a race to the bottom, why you should never just cut grass, and the exact strategy he recommends for landing your very first luxury client using nothing but a $500 investment and a yard sign.If you're ready to stop competing on price and start becoming the undisputed expert in your market, this episode delivers the blueprint.🎙️ What You’ll Learn in This Episode:The Free Yard Sign Strategy: How to land your first high-paying customers by offering free, creative work in wealthy neighborhoods to trigger word-of-mouth referrals.Commodity vs. Creative: Why services like laying pavers or cutting grass kill your margins, and how to pivot to high-profit, creative planting where you charge for the outcome, not the flower.Managing Elite Clients: The "no excuses" approach to project management that wealthy clients demand when things inevitably go wrong on a job site.Trust and Verify: Steve’s golden rule for hiring a team and stepping out of the day-to-day labor so you can focus purely on sales, marketing, and brand vision.Tags: Home Services, Service & Consulting, Business mindset, Business scaling, Luxury LandscapeResourcesGrow your business today: https://links.upflip.com/the-business-startup-and-growth-blueprint-podcast Follow Our Second Channel Here: https://next.upflip.com/spotify Connect with Steve: https://www.linkedin.com/in/stevegriggsdesign

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