Contractor Evolution

Breakthrough Academy

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. DEC 17

    251. Are Trades Businesses Future-Proof? (AI Is Coming) - Kasim Aslam

    Take our 5 minute quiz and get your free Contractor Growth Roadmap: https://trybta.com/DL251 To learn more about Breakthrough Academy, click here: https://trybta.com/EP251 Will AI replace construction workers? 🤔 Not yet. But if it ever does, the most successful contracting businesses will be the ones who adapt the quickest. So how do you make sure your business is ready for automation and AI in construction to improve and gain popularity? Today’s guest, Kasim (think “awesome” with a K) Aslam has built and exited multiple multimillion-dollar companies and now dedicates his time to helping business owners and their teams take control of AI… …Before it takes control of them. And in his opinion, that doesn’t mean automating EVERYTHING. It actually means doubling down on humanity at every possible opportunity. If you want to future-proof your business and stay on the right side of the AI revolution, this one’s for you. Episode highlights: Get perspective on the AI revolution from Kasim Aslam, renowned entrepreneur, business strategist and co-founder of Pareto Talent: a Virtual - Assistant agency that focuses exclusively on connecting owners with AI-empowered admin support.Learn why scalable things may not be relevant in the age of AI (and the shifts you need to make to future-proof your company).Understand why doubling down on your people is the counterintuitive way for contractors to win in the modern world. 00:00-Intro 01:15-What will trades businesses look like as AI progresses? 09:35-Are small businesses screwed in the age of Private Equity? 15:21-Biggest AI opportunities and biggest AI red flags 26:59-What happens in 10 years? 36:03-What should contractors be focused on right now? 38:54-Kasim's thoughts on the emotional side of selling a business 49:49-Wrap up

    50 min
  2. DEC 10

    250. Can Learning Less Can Make You More Successful? - Pat Flynn

    Take our 5 minute quiz and get a custom Contractor Growth Roadmap: https://trybta.com/DL250 To learn more about Breakthrough Academy, click here: https://trybta.com/EP250 Do you ever feel like there is WAY too much to learn or feel guilty for not learning enough? Financial literacy, AI, automation software, job site best practices, leadership theory… The list of things you COULD go and figure out is endless. But what if I told you the answer is actually to learn LESS? Our guest today is Pat Flynn: entrepreneur, podcast host and author of several books including Superfans and Will it Fly? In his newest book Lean Learning, Pat lays out a tangible framework for spending LESS time learning the RIGHT things. And today, we’re talking about how to understand what you NEED to learn, what you WANT to learn, and what you DON’T need to learn at all. Episode Highlights: - Understand the dangers of “over-learning” as a contractor and entrepreneur and why we feel so much pressure to “know it all.” - Learn Pat’s framework for determining what is worth learning and what is a waste of your time and energy. - Get tips on avoiding “analysis paralysis” by focusing on ONLY the important data points to make a decision for your business. Get Pat's book here: https://leanlearningbook.com/ Want to learn more about prioritization and decision making? Check out these videos 👇 📝Steal These Prioritization Methods to Get More Done: https://youtu.be/-9zk4mQfL7k ⏰Matt Risingers’ $10MM Time Blocking System REVEALED: https://youtu.be/Pdf4Vpq1KZ4 ✋No More Excuses: Stay Consistent When Goals Go Sideways: https://youtu.be/YBa20g7kQRc 00:00-Intro 01:39-The dangers of "over-learning" for contractors 07:58-The Inspiration Matrix 17:50-"Just in time" learning vs "Just in case" learning 24:45-The importance of community to a contractor's learning journey 33:57-Thinking through the risks vs. "just going for it" 42:54-Micro-mastery vs. Quantum Leaps 51:00-Wrap up

    53 min
  3. DEC 3

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

    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
  4. NOV 26

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

    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
  5. NOV 19

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

    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

    56 min
  6. NOV 12

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

    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
4.7
out of 5
49 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.

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