Sometimes the biggest wins in business come from the boldest pivots.
For Dave Sheridan, that pivot happened in 2023 when he was “inches away” from spending $30,000 on a sailboat. Instead, he sold his house, invested $130,000 into equipment, and launched Ascension Tree Care in Milford, Michigan.
Two years later, the company is pacing for $650K–$750K in annual revenue, with a growing team, strong Google presence, and a new plant healthcare division that promises recurring revenue. His story is a blueprint for anyone who feels stuck in their career and wants to build something real.
The Burn-the-Ships Leap
Before tree work, Dave spent a decade in manufacturing software sales—comfortable, but unfulfilled. After watching his brother (an arborist) at work, he saw both the skill required and the business potential. Armed with spreadsheets and sales experience, he sold his house, bought gear, and partnered with his brother and a close friend.
That all-in decision gave him momentum. By the end of his first partial year (May–Dec 2023), they pulled in $290K. The following year: $550K. Now in year three, they’re scaling toward three-quarters of a million.
The Tools That Defined the Business
Their starter kit included a used chip truck, a 12-inch chipper, a dump trailer, and a work truck. Later came the game-changing mini skid steer. Renting one at $400/day drained profits fast. Buying one paid for itself in efficiency, safety, and the ability to land bigger jobs.
These equipment choices also defined their market. Instead of chasing land clearing projects (where full-size skid steers dominate), Ascension Tree Care leaned into residential work. Their mini skid can squeeze through 36-inch gates—perfect for lake homes and tight-access backyards around Metro Detroit.
Why Plant Healthcare Changed the Game
For Dave, the future of tree service isn’t just in removals and trimming—it’s in plant healthcare.
Unlike one-off removals, plant healthcare brings customers back season after season. Treatments for pests, diseases, and overall tree health create recurring revenue, boost customer lifetime value, and make the company more attractive for acquisition down the line.
Startup Costs
Surprisingly, it doesn’t take millions to get started. Ascension Tree Care invested about $25K total:
- $13K for a used flatbed truck
- $10K for a water tank and motor
- Additional spend for chemicals and PPE
Knowledge Investment
The real challenge isn’t the money—it’s the know-how. Even with Dave’s brother’s arborist background and degree in environmental science, the learning curve was steep. Diagnosis, application methods, and regulations are always evolving.
Still, it’s worth it. Dave’s dad now runs the plant healthcare applications, giving him a purposeful role while keeping sales and pricing in more experienced hands.
Strategic Payoff
Plant healthcare smooths out the seasonal rollercoaster. Instead of scraping through slow winter months, Ascension can keep cash flow alive with contracts from golf courses and repeat customers who want healthier trees year after year.
Dave summed it up well:
“There’s really only one way to build a customer base in plant healthcare—you’ve got to get out there, sell, and refine the system as you go.”
Marketing That Worked
Like most startups, Dave leaned on his network early. But scaling meant layering in smarter marketing channels:
- Google Business Profile: Over 100 reviews, fueled by a process (ask onsite, send a text link, follow-up email).
- Google Ads: Outsourced after a rocky DIY attempt. Current cost per lead ranges from $60–$150 depending on keyword.
- Direct Mail (EDDM): Postcards targeting lake homes deliver a steady return.
- B2B Outreach: Adapted from “@StumpGuyTy” playbook, emailing landscapers, builders, and golf courses. This landed recurring contracts and off-season work.
Facebook ads haven’t worked yet, but Dave is testing simple iPhone “before and after” videos, which consistently perform well for other service businesses.
Building a Strong Team
Ascension Tree Care is a true family business. Dave runs estimates and admin, his brother leads climbing and plant healthcare, and their friend Scott handles operations and equipment. Two crew members are learning to climb, Dave’s sister helps with phones, and his dad now focuses on plant healthcare applications.
Partnership works here because roles are crystal clear:
“It’s like a marriage. You need trust, defined responsibilities, and upfront conversations about what happens if someone wants out.”
Key Takeaways
Dave’s story is proof that you don’t need a perfect plan—you need a bold move and relentless follow-through.
- Go all in: Selling his house created the urgency and capital to launch.
- Invest smart in equipment: The mini skid was worth every penny.
- Add recurring revenue: Plant healthcare is the lever that turns a seasonal business into a scalable one.
- Market aggressively: Google reviews, PPC, and B2B outreach built a reliable pipeline.
- Build the right team: Clear roles and trust are non-negotiable in partnerships.
For anyone stuck in a job that feels safe but empty, the lesson is simple: choose a challenge, commit fully, and build from there. You don’t need to know your five-year plan—you just need to do the next thing.
