Contractor Evolution

Breakthrough Academy
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Breakthrough Academy presents Contractor Evolution. In this show we unpack the systems, tactics, and skills you need to take your fast-growing contracting business to the next level. If you’re here to learn what it takes to scale up, work less, and increase profitability, you’ve come to the right place. Stay tuned to learn what separates the new breed of contractor from the old school, and welcome to your ultimate guide to the business of contracting.

  1. 2D AGO

    249. How $10MM contractors get more done (with less meetings, emails, and messages) - Luke Hansen, Blake Butry and Adam Sylvester

    Landscapers! Learn how to build a killer annual strategic plan for your business at our free web class on December 9. Spaces are limited, so save your spot now. https://trybta.com/CE-SPL-Dec9 Get your free communication resource bundle here: https://trybta.com/DL249 To learn more about Breakthrough Academy, click here: https://trybta.com/EP249 How much money have you lost to unclear instructions, buried emails, and missed change orders? Poor communication is a hidden cash flow destroyer EVERY contractor falls victim to, but no one really talks about. In today’s episode of Contractor Evolution, Danny is joined by CompanyCam founder Luke Hansen and two high performing contractors for a roundtable discussion on how to invest in clear (and profitable) communication across your organization. You’ll learn: ⚙️ Real world systems for keeping your crews, project managers and clients all on the same page 🗣️ The single most impactful communication ritual to aligning your team with your company goals 💪 The secret to maintaining healthy projects, keeping things on time and on budget Want more webinar replays? Check out these episodes 👇 Episode 244: Secrets of $10MM Contractors: 6 Steps to Freedom Episode 231: STOP Losing Money to Poor PM: No-Frills Project Management Tips Episode 212: How to Manage Budgets, Forecasting and Cash Flow Like Matt Risinger 00:00-Intro 05:32-Meet the panel 08:28-Transfer in: Where is your communication costing you sanity/time/money? 14:32-Signs your communication is whack 21:58-Question 1: How do you ensure communication doesn't all flow through YOU? 32:28-Question 2: How do you keep your team on the same page? 42:21-Question 3: What does a strong sales-to-production handoff look like? 54:46-Biggest takeaways 59:39-How to implement change (next steps) 01:11:45-Bonus question: What communication tools do you use?

    1h 24m

  2. NOV 26

    248. How to Destroy Your Limiting Beliefs (Real Coaching Session) - Kedma Ough

    Landscapers! Learn how to build a killer annual strategic plan for your business at our free web class on December 9. Spaces are limited, so save your spot now. https://trybta.com/CE-SPL-Dec9 To learn more about Breakthrough Academy, click here: https://trybta.com/EP248 Take our 5 minute quiz and get your custom roadmap to growing your contracting business: https://trybta.com/DL248 When you don’t have anyone keeping you in check, it’s all too easy to get caught up in your own limiting beliefs. Today, business therapist Kedma Ough is on the show to coach Danny and show how tough love can be exactly what you need to break out of a negative thought pattern. — Do you struggle with limiting beliefs or negative self talk? Owning a contracting business makes it pretty hard not to. Complex operations, difficult team members, unhappy clients… the list of negative experiences you have in a week (or a day) is endless. In this episode, business therapist, TedX Speaker and bestselling author Kedma Ough coaches Danny on air to help him break out of old thought patterns and adopt a more positive mindset. We hope this shows you how you can do the same. Episode Highlights: Watch a real life coaching call take place between Danny and business therapist, TedX speaker and bestselling author Kedma Ough.Learn how to unpack your own limiting beliefs by watching Kedma help Danny to do just that.Get strategies for breaking the cycle of negative self-talk on your own or with a coach, therapist or counsellor. More episodes to help get rid of your head trash: 👉 How To Lead WITHOUT Ego (Keith Mercurio's Advice) 💲 Why Most Entrepreneurs Stay Broke - Garrett Gunderson 🧠 4 Mindset Shifts For When You Want To Give Up 00:00-Intro 01:46-Kedma's origin story 16:02-Identifying and challenging limiting beliefs 39:09-Kedma's playbook for destroying limiting beliefs 58:09-Common limiting beliefs for entrepreneurs 08:26-Wrap up

    1h 12m

  3. NOV 19

    247. How AI + One Key Role Will Systemize Your Entire Business - David Jenyns

    Landscapers! Learn how to build a killer annual strategic plan for your business at our free web class on December 9. Spaces are limited, so save your spot now.  https://trybta.com/CE-SPL-Dec9 Take our five minute quiz and get a free custom road map to growing your contracting business: https://trybta.com/DL247 To learn more about Breakthrough Academy, click here: https://trybta.com/EP247 Building systems is the key to scaling your contractor business—but let's be honest, it's time-consuming and tedious work that most visionaries hate doing. What if there was ONE role that could build all your systems for you? In this episode of Contractor Evolution, Systemology author David Jenyns returns to introduce his groundbreaking new concept: The Systems Champion. This isn't an ops manager. It's not a COO. And it's not necessarily an integrator. It's something different—and potentially more powerful—especially as AI transforms how we work. David breaks down exactly what a Systems Champion is, who's the right fit for this role (the answer might surprise you), and how to create and fill this position in your business starting today. If you've been stuck in the weeds building systems yourself, this conversation will change everything. 🎯 WHAT YOU'LL LEARN: • What a Systems Champion actually is (and why it's different from other roles) • The exact profile of who makes the best Systems Champion in your business • How to create this role without adding massive overhead • Why AI is making this role MORE important, not less • Step-by-step process to implement a Systems Champion in the next 90 days • Real examples of how this role transforms contractor businesses 👤 ABOUT DAVID JENYNS: David Jenyns is the author of Systemology and the newly released Systems Champion. He's helped thousands of businesses create scalable systems without the business owner doing all the heavy lifting. His frameworks have transformed how contractors and service businesses approach systemization. 📚 Get David's new book: https://www.systemology.com/scbook/ 🌐 Learn more about David's work: https://www.systemology.com/ 🎥 Check out the last episode we did with David: https://youtu.be/eKNW3GQRM8M More videos on systems building: 🚨4 Essential Business Systems Every Contractor Should Master (with Tony Fraser-Jones): https://youtu.be/4ljBnnHgHJE 🦾From Reactive to Streamlined: Cory’s Business Automation Journey: https://youtu.be/NykhB5J8cE0 💰This $10MM Accountability Systems Has Crews CRUSHING Their Goals (free web class): https://youtu.be/NvBjWbxXjcI 00:00-Intro 01:40-About Dave's new book: Systems Champion 05:38-How to know if you need a Systems Champion 17:16-Traits of a great Systems Champion 29:58-What does a Systems Champion actually do? 38:33-How to make your Systems Champion act as your AI Champion 46:02-How long do we have before AI takes over the trades? 53:37-Wrap up and final thoughts

    57 min

  4. NOV 12

    246. How 8 Years in a Community Changed My Contracting Business - Ryan Lermitte

    Landscapers! Learn how to build a killer annual strategic plan for your business at our free web class on December 9. Spaces are limited, so save your spot now.  https://trybta.com/CE-SPL-Dec9 Take our five minute quiz and get a free custom roadmap to growing your contracting business: https://trybta.com/DL246 To learn more about Breakthrough Academy, click here: https://trybta.com/EP246 Entrepreneurship doesn't have to be lonely. But for most contractors, it is. After years of grinding alone, Ryan Lermitte from Umbrella Property Services discovered something that changed everything: the power of real community. In this episode of Contractor Evolution, Ryan shares his 8-year journey with Breakthrough Academy and reveals why he stayed long after learning the systems. The deep connections, unexpected collaborations with competitors, and the emotional ROI that no spreadsheet can capture. If you've ever felt isolated in your business journey, this conversation will remind you that you're not meant to do this alone. 🎯 WHAT YOU'LL LEARN: Why entrepreneurship feels so isolating (and what to do about it) How investing in community and connections can improve your wellbeing AND your profitability. Why emotional ROI matters as much as financial returns Practical ways to build meaningful connections in your industry ☂️Learn more about Ryan and his business: https://umbrellaservices.ca/ 📈Learn more about how Breakthrough Academy helped Ryan double his revenue and make his goals a reality: https://youtu.be/Pa39XAcLRMY Other stories from REAL contractors like Ryan: 🦾From Reactive to Streamlined: Cory’d Business Automation Journey: https://youtu.be/NykhB5J8cE0 ✋STOP Losing Money to Poor PM: No Frills Project Management Tips (Contractor Roundtable): https://youtu.be/xIMb9X4A2Zo ⭐️More coaching success stories: https://www.youtube.com/playlist?list=PLGzGbmYmvpYonpJ_EAAUldCob7iimjgmc 00:00-Intro 01:46-About Ryan's journey in Breakthrough Academy 06:46-How do you build relationships beyond transactions? 15:19-How to "Be Real" with the people around you 17:55-The true ROI of community as a contractor 22:14-How to overcome imposter syndrome 26:24-Why give back? 31:05-Should you collaborate with your competitors? 34:03-Ryan's unforgettable moment from Winter Summit 2025 39:26-How to know if you're in the right community 45:38-Wrap up and how to connect with Ryan

    47 min

  5. NOV 5

    245. The AI Playbook Every Contractor Needs in 2025 - Greg Shove

    Landscapers! Learn how to build a killer annual strategic plan for your business at our free web class on December 9. Spaces are limited, so save your spot now.  https://trybta.com/CE-SPL-Dec9 Take our 5 minute quiz and get a custom roadmap to systemizing your contracting business: https://trybta.com/DL245 To learn more about Breakthrough Academy, click here: https://trybta.com/EP245 Over the next 5 years the ability to leverage AI tools is going to make or break contracting businesses. But 99% of contracting business owners are barely scratching the surface. Today we’re joined by Greg Shove, founder of Section AI, who’s gonna teach us how to go from AI-anxious to AI-fluent. In this episode, we cover: A roadmap to learning AI for beginners, intermediates and even well-versed contractorsWhat it takes to build a shared company brain that knows your systems, data, and workflowsAnd specific ways to use AI for construction businesses, home service companies and other trades. If you’re ready to stop treating AI like a toy and start using it as your competitive edge, this conversation is for you. 00:00-Intro 01:38-About Greg and Section AI 01:38-About Greg and Section AI 03:34-The AI Revolution: What's Happening and What's Next 07:21-How small business should be benefitting from AI 13:16-Are the trades AI proof? 19:39-Creating a "company brain" with AI tools 29:31-Practical use cases of AI tools for contractors 37:53-How to take the first step to make AI part of your company culture 44:37-Wrap up and next steps

    47 min

  6. OCT 31

    244. Secrets of $10MM Contractors: 6 Steps to Freedom - Danny Kerr

    Landscapers! Learn how to build a killer annual strategic plan for your business at our free web class on December 9. Spaces are limited, so save your spot now.  https://trybta.com/CE-SPL-Dec9 Grab your FREE Contractor Growth Method resource bundle: https://trybta.com/DL244 To learn more about Breakthrough Academy, click here: https://trybta.com/EP244 Whether it's being on the tools, selling jobs, or bookkeeping, we all have something in our business that we HATE doing—and for most 7 figure contractors, it's the relentless struggle with contractor cash flow and time management. The good news? There’s a predictable way out of small business owner burnout. After working with over 1,900 contractors, we’ve learned there are six key systems that, once implemented, give owners the freedom to do whatever they want while truly mastering contractor scaling. 🔨 Swing a hammer. 💼 Lead a sales team. ⚾️ Coach baseball. 🇬🇷 Move to Greece. These proven contractor time management systems transform how 7 figure contractors operate—no more 14-hour days, no more cash flow stress, no more feeling trapped in your business. In a web class we hosted a while back, I unpacked those six contractor scaling systems step-by-step—the same ones that help contractors break free from small business owner burnout and finally build businesses that serve them. Today, that web class is hitting the podcast. You’ll learn: - How to build a business budget to help with contractor cash flow and financial management - The foolproof hiring systems 7-figure contractors use to secure top talent - How to level up your time management skills to implement more systems faster 00:00-Intro 00:54-Welcome to the web class 09:06-About the 6 Systems (Contractor Growth Method™) 10:27-System 1: Financial Controls 14:39-System 2: Defined Roles 21:20-System 3: Hiring Systems 26:20-System 4: Training & onboarding 33:02-System 5: Sales & marketing 39:31-System 6: Goal Setting & Review 49:34-Getting started 57:59-Q&A

    1h 11m

  7. OCT 29

    243. Leading The Change in The Green Industry - Mark Sedgley

    Landscapers! Learn how to build a killer annual strategic plan for your business at our free web class on December 9. Spaces are limited, so save your spot now.  https://trybta.com/CE-SPL-Dec9 Take our 5 minute quiz and get a custom Contractor Growth Scorecard today: https://trybta.com/DL243 To learn more about Breakthrough Academy, click here: https://trybta.com/EP243 LMN, Greenius and SingleOps are three of the biggest names in landscaping software. After rebranding to Granum, CEO Mark Sedgley is on the show to talk about the bright future of the green industry. --- What does it take to lead lasting change, not just inside your business, but across an entire industry? Today’s guest is Mark Sedgley, CEO of LMN, Greenius, and SingleOps, three of the biggest names in landscaping software that are now coming together as one brand: Granum. Mark’s story—from entrepreneur to CEO—offers a masterclass in leadership, accountability, and building companies that put people first. In today’s episode, we talk about his vision for Granum, and what he sees as the future of the green industry. Episode Highlights: - Learn why Granum, the amalgamation of LMN, Greenius and SingleOps was created, straight from CEO Mark Sedgley. - Understand Mark’s entrepreneurial journey and how you can benefit from the lessons he’s learned about leadership. - Get insight into the bright future of the green industry and the trades more broadly from someone who is actively working to improve and professionalize the space. Learn more about Granum: https://granum.com/ 00:00-Intro 01:38-Mark's journey in the Green Industry 10:52-Being an entrepreneur vs. being a CEO 17:10-How to make the right decisions as a CEO 23:26-The future of the Green Industry 30:05-How to address change management in a rapidly changing industry 33:44-About the Granum rebrand: how did LMN, Greenius and SingleOps come together? 39:28-Finding balance as a high-impact CEO 43:52-Wrap up

    46 min

  8. OCT 22

    242. 4 Mindset Shifts For When You Want To Give Up - Danny Kerr

    Landscapers! Learn how to build a killer annual strategic plan for your business at our free web class on December 9. Spaces are limited, so save your spot now.  https://trybta.com/CE-SPL-Dec9 Take our five minute quiz and get your free custom Contractor Growth Scorecard here: https://trybta.com/DL242 To learn more about Breakthrough Academy, click here: https://trybta.com/EP242 Some moments in life can completely shape the way we see the world. Hard lessons, key pieces of advice, or sudden realizations in the face of adversity. Today, Danny is opening up about four moments in his life that would become the mantras he uses to survive and thrive as a successful contractor, business coach and entrepreneur. Episode Highlights: Hear the story of how Danny went from a struggling dyslexic student to a successful paint contractor to the thriving founder and coach he is today.Understand the power of mantras in overcoming adversity, navigating relationships and staying calm under pressure.Benefit from Danny’s vulnerability, as he opens up about the personal and professional mistakes over the last 20 years as an entrepreneur. 00:00-Intro 01:16-Habit #1: F*ck it 04:32-Habit #2: “How can I…?” 07:32-Habit #3: Relinquishing control 09:07-Habit #4: “It’ll be fine.” 11:15-Wrap Up

    12 min
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4.9
out of 5
64 Ratings

About

Breakthrough Academy presents Contractor Evolution. In this show we unpack the systems, tactics, and skills you need to take your fast-growing contracting business to the next level. If you’re here to learn what it takes to scale up, work less, and increase profitability, you’ve come to the right place. Stay tuned to learn what separates the new breed of contractor from the old school, and welcome to your ultimate guide to the business of contracting.

Information

  • Creator
    Breakthrough Academy
  • Years Active
    2020 - 2025
  • Episodes
    249
  • Rating
    Explicit
  • Copyright
    © Copyright 2025
  • Show Website
    Contractor Evolution

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