Scaling From $1M to $50M+

First, as we head into the holidays next week, I want to start off by saying thank you. This past year was incredible and filled with a lot of growth and learning. ShareWillow is my life’s work and I really appreciate you all being on this journey with us.

Over the course of this year, I’ve met hundreds of incredible business owners from across the country. Those conversations inspired me to start the ShareWillow Podcast, which has been one of the most fulfilling things I’ve done this year.

I started the podcast with a simple goal: uncover exactly how the best owners in the trades grow revenue, protect their margins, and build lives they actually enjoy.

I wanted to take this moment to recap some of the learnings from the podcast this year. In this newsletter, we’re recapping six pieces of advice that fundamentally changed how I think about service businesses.

Craig (Ocean State Air) scaled from $1M to $8M in eight years by shifting his perspective on assets. He stopped viewing vans as vehicles and started viewing them as individual business units capable of generating $1.5M annually.

He told me, "I want to get my guys trained up and to a point where each installer or lead has its own business."

When a lead technician understands they are the CEO of their truck — making them responsible for gross margins, job costs, and customer satisfaction — everything changes. Instead of micromanaging start times, Craig helps them understand the numbers that drive profitability. They stop acting like employees who happen to drive company vehicles and start acting like owners running million-dollar ventures.

Jarod Smith (Clogbusters) dropped a hard truth about leadership energy. Most owners tend to spend the majority of their time trying to help the people at the bottom. "We're like, 'Oh man, poor Jimmy. His numbers are bad... we know Jimmy can do it,'" Jarod said.

But that energy is wasted. It’s like a quarterback coach ignoring Peyton Manning to spend 70% of their time on the third-string rookie.

Jarod’s advice is to devote your time to your A-players (the people at the top). Give them the transparency and tools to break records. The bottom performers will either step up to match the culture, or they will step out.

Chase Farris attributes his growth from one truck to $2M in revenue to one metric: Speed. He operates on the 24/48 Rule: Respond to a lead within 24 hours, and get on-site for an estimate within 48 hours.

When a lead comes in, Chase’s team calls immediately. Then within 48 hours they show up with a wrapped vehicle, uniforms, and a professional presentation. "I always try to put myself in their shoes and what I would want when someone was coming to bid for my property," Chase said. While competitors are winging it, Chase systemized the customer experience from first contact.

Lacey Coleman trains her team to sell the lifestyle, not the machinery. When presenting options, she uses a "Standard, Good, Better, Best" model, but follows it up with storytelling.

Instead of pitching a "high-efficiency variable speed unit," she pitches a unit based on the customer's life. If a customer entertains outdoors, she says: “We have something you can stand next to and you can barely tell that they're running. It’s an extra $5,000 because it's more efficient and it's very quiet." The specs justify the price, but the story closes the deal.

Jim Hinshaw (Service Nation) insists you stop selling "maintenance agreements." A "maintenance agreement" sounds like a chore. A "Club Membership" sounds exclusive and valuable.

The pitch isn't just about checking a box, it's about selling prevention. Jim tells the story of a condenser fan blade that develops a tiny crack. A tech on a routine visit spots it and fixes it for cheap. If missed, it shatters in July, destroying the condenser coil and leaving the homeowner without A/C for weeks. The "Club" turns a potential disaster into a simple fix.

Zach Rollins (Downspout) figured out a way to turn the awkward "tipping moment" into a massive marketing engine for his power-washing business.

Instead of asking customers to tip his technicians directly, he trains his team to say: "If you want to take care of the tip, just leave us a five-star review mentioning my name, and the company will give me $20."

This is brilliant for three reasons:

The result? 40% of Downspout's customers leave reviews, and some of his employees are adding $500 a week to their paychecks through performance incentives.