Winter Summit 2026: 6 Contractor Coaching Members Who Achieved Award Winning Results

Every year at Winter Summit, the Breakthrough Academy community gets a rare look at what real progress looks like across the trades. Not polished highlight reels, but honest stories of growth, setbacks and leadership in action.

During our annual awards night ceremony, we recognize contractor coaching Members with standout accomplishments, from profit gains to community involvement.

This year’s award winners didn’t just build better businesses. They built better habits, stronger teams and clearer thinking. Here’s what stood out.

Charlie Bethell: Community Drives Growth

As this year’s Community Builder of the Year, Charlie’s impact wasn’t measured in revenue. It was measured in relationships.

Even as a self-described introvert, he made a deliberate decision to show up. Charlie leaned into something many contractors avoid: connection.

The takeaway? Growth doesn’t just come from systems, but it comes from people. The more you give to your network, the more your business expands with it.

Bill & Taffy Ragan: Turnaround Starts With Ownership

Winners of Turnaround Business of the Year, Bill and Taffy proved that even the toughest seasons can be reversed with the right approach.

A year ago, their business was deep in the red. Fast forward 12 months, and they’ve rebuilt into a profitable and stable operation.

The shift wasn’t luck, but it was leadership alignment. They got clear on roles and committed to better hiring. They also stopped reacting to problems.

Their story is a reminder that tough years aren’t the end. They’re just data, and what matters is what you do next.

Ryan Lermitte: Leadership Is Presence

Named Leader’s Circle Member of the Year, Ryan’s growth was beyond business performance. It was in how he showed up.

He focused on protecting his attention, being more present and leading with authenticity. He’s now got stronger relationships, better decision-making and a more balanced business.

When a leader’s distracted, the team feels it. Your leadership starts with how you show up every day.

Blake Butry & Danny Phillips: Execution Changes Everything

Blake and Danny, owners of roofing company Churchill USA won Implementers of the Year because they didn’t just talk about systems, but also built them.

From recruiting pipelines to SOP libraries, they committed to implementation at a high level. But their key quality is their mindset: fail forward, fail faster, then just do the thing.

Too many contractors know what to do but hesitate. Be like Blake and Danny - execute!

Curt Janzen & Kevin Boschee: Leadership Is a Team Sport

Curt and Kevin from the Beyond Group of Companies have shown what’s possible when leadership is shared and not carried alone.

Recognized as Leaders of the Year, their success wasn’t just about numbers, though the numbers were strong. It was about partnership.

They built a business where accountability, trust, investment in people and complementary leadership styles drive results.

If you’re trying to carry everything yourself, you’re limiting your growth. This leadership duo proves that strong businesses are built by strong partnerships.

Nick & Joe Cloutier: Systems Unlock Scale

As Entrepreneurs of the Year, Nick and Joe from Willie C. & Sons Landscaping demonstrated what happens when grit meets structure.

Nick started with hustle, but real growth came when he stepped out of the day-to-day and built systems. Bringing in his brother, implementing KPIs and focusing on data over guesswork transformed the business into a scalable operation.

The key lesson? Hard work gets you started. Systems take you further.

Ready to Build a Better Business?

If you see yourself in these stories, and you’re ready to take the next step, book a complimentary discovery call with Breakthrough Academy. We’ll help you turn insight into action and build a business that actually works for you.