He Grew a Gutter Company to $6.5M Using This Mindset

Running a contracting business in 2026 isn’t easy. Many owners come into the year with ambitious goals, only to hit unexpected setbacks: slower sales, staffing changes, rising pressure, and the constant feeling that there’s always more to fix.

In a recent episode of Contractor Evolution, former BTA Member turned coach, Jason Alcott, joined Danny Kerr to unpack one of the biggest challenges contractors face during uncertain times: mindset.

Jason has sat on both sides of the table — first as the GM of a growing contracting business and now as a coach working with dozens of BTA members. One pattern he sees over and over again is contractors getting trapped in what he calls the Gap, where they're constantly measuring themselves against where they want to be instead of recognizing the progress they’ve already made.

The result? Burnout, frustration and reactive decision-making.

Instead of jumping straight into tactics, Jason argues that business owners first need to reset how they view their business, their team, and their progress.

Key takeaways for contractors:

• Your mindset impacts your entire team.
  When owners operate from stress and frustration, teams feel it immediately. That energy affects communication, morale, and decision-making throughout the company.
• Don’t ignore your wins.
  Jason encourages contractors to regularly stop and identify three wins from the previous week. It sounds simple, but it shifts your focus from problems to progress. This also helps create momentum.
• Aggressive goals are fine, if you measure progress properly.
  Contractors often set ambitious targets, then beat themselves up when they fall short early in the year. Jason’s advice: focus on gains and progress, not just the distance between you and the end goal.
• Short-term team goals create engagement.
  One practical strategy discussed in the episode is creating 90-day goals that every employee can influence. When teams can see measurable progress and celebrate small wins together, engagement increases dramatically.
• Positive momentum matters.
  Businesses grow faster when teams feel like they’re winning. Celebrating progress consistently can change the entire atmosphere inside a company.

The conversation is a strong reminder that scaling a contracting business isn’t just about systems and strategy. The way you think, and the way you lead your team through challenges, directly affects your results.

If you’ve been feeling stuck, overwhelmed, or frustrated in your business lately, this episode offers a practical framework for resetting your perspective and regaining momentum.

Ready to build a business that grows without burning you out? Book a complimentary discovery call with Breakthrough Academy to explore how our coaching, systems and community can help you scale with more clarity and confidence.