Contractor Evolution

Breakthrough Academy
  • 4.9 (64)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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. 7 HRS AGO

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

    Builders! Don’t leave 2026 to chance! Join our free strategic planning web class on November 18 to get ahead: learn how to spot cash flow crunches before they hit, identify who to hire before you need them, and lock it all into a proven annual plan used by 1,900+ contractors. Click the link to register now: https://trybta.com/CE-SPB-Nov25 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

  2. NOV 5

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

    Builders! Don’t leave 2026 to chance! Join our free strategic planning web class on November 18 to get ahead: learn how to spot cash flow crunches before they hit, identify who to hire before you need them, and lock it all into a proven annual plan used by 1,900+ contractors. Click the link to register now: https://trybta.com/CE-SPB-Nov25 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

  3. OCT 31

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

    Builders! Don’t leave 2026 to chance! Join our free strategic planning web class on November 18 to get ahead: learn how to spot cash flow crunches before they hit, identify who to hire before you need them, and lock it all into a proven annual plan used by 1,900+ contractors. Click the link to register now: https://trybta.com/CE-SPB-Nov25 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

  4. OCT 29

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

    Builders! Don’t leave 2026 to chance! Join our free strategic planning web class on November 18 to get ahead: learn how to spot cash flow crunches before they hit, identify who to hire before you need them, and lock it all into a proven annual plan used by 1,900+ contractors. Click the link to register now: https://trybta.com/CE-SPB-Nov25 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

  5. OCT 22

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

    Builders! Don’t leave 2026 to chance! Join our free strategic planning web class on November 18 to get ahead: learn how to spot cash flow crunches before they hit, identify who to hire before you need them, and lock it all into a proven annual plan used by 1,900+ contractors. Click the link to register now: https://trybta.com/CE-SPB-Nov25 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

  6. OCT 15

    241. Is SEO Dead? Modern Contractor Marketing Tips - Phil Risher

    Builders! Don’t leave 2026 to chance! Join our free strategic planning web class on November 18 to get ahead: learn how to spot cash flow crunches before they hit, identify who to hire before you need them, and lock it all into a proven annual plan used by 1,900+ contractors. Click the link to register now: https://trybta.com/CE-SPB-Nov25 Take our 5 minute quiz and get your free personalized Contractor Growth Scorecard today: https://trybta.com/DL241 To learn more about Breakthrough Academy, click here: https://trybta.com/EP241 In a world where everyone turns to AI to ask questions, how do you make sure YOU show up as the answer? In today’s episode, Phil Risher reveals the secret to getting ChatGPT and other Large Language Models (LLMs) to promote your business to potential customers in every related search. --- There’s no question that AI is changing the way people ask questions online. So, how do you make sure YOU show up as the answer? In today’s episode, we’re revealing the secret to getting ChatGPT and other Large Language Models (LLMs) to promote your business to potential customers in every related search. Contractor Marketing expert Phil Risher is a long-time SEO strategist that has been on the front lines as AI has changed the game for contractors and home service businesses.  Our conversation covers: The difference between SEO, GEO and AEO and where you should invest your marketing efforts right nowHow Large Language Models actually decide which brands to recommend 4 personalized videos you can make in the next 10 minutes that will increase your conversion rate by 20%. This is a mandatory listen for contractors in every industry. 00:00-Intro 02:07-About Phil and Phlash Consulting 05:29-How is AI disrupting customer search? SEO vs. GEO vs. AEO 12:49-Is SEO still worth doing? 16:10-Becoming a content authority 29:21-How important is a "face of the brand?" 32:41-4 personalized videos for your drip sequence 38:44-Use cases for AI chat bots & automation for speed to lead 41:45-Use cases for self service tools 46:14-How to stay up-to-date on AI without getting overwhelmed 49:58-Connect with Phil

    52 min

  7. OCT 8

    240. Do Free Vacations Close More Deals? John Dwyer’s CRAZY Strategy - John "JD" Dwyer

    Builders! Don’t leave 2026 to chance! Join our free strategic planning web class on November 18 to get ahead: learn how to spot cash flow crunches before they hit, identify who to hire before you need them, and lock it all into a proven annual plan used by 1,900+ contractors. Click the link to register now: https://trybta.com/CE-SPB-Nov25 Take our 5 minute quiz and get your free personalized Contractor Growth Scorecard today: https://trybta.com/DL240 To learn more about Breakthrough Academy, click here: https://trybta.com/EP240 What if you offered a potential customer a free vacation if they hired you by the end of the week? Would it increase your closing rate? Today’s guest John Dwyer (JD, for short) swear by this strategy and in this episode, he’s gonna tell you why. --- What if you offered a potential customer a free vacation if they hired you by the end of the week? Gimmicky? Maybe. But according to today’s guest, it works. John Dwyer, or “JD” for short, has built an entire business around incentive-based marketing. In other words, rather than resorting to price discounting to get more work, what if you looked for a value add incentive instead? Sometimes that’s something small, like a Happy Meal toy. Sometimes it’s a free trip to Disneyland. In this episode, JD breaks down what he thinks are the 5 elements of a successful direct response campaign, including what he calls the WOW factor incentive. This guy’s got some seriously out of the box ideas, so buckle up. Episode Highlights: - Learn how John “JD” Dwyer has used incentive-based marketing to generate over $15 billion in extra sales for businesses across multiple industries. - Understand what the “WOW Factor” is and how it might fit into your marketing strategy. - Get inspired to find creative alternatives the next time you’re thinking of price discounting to get more sales. Get in touch with JD at john@theinstituteofwow.com Learn more about the Institute of Wow vacations Incentive - https://vacationsincentive.com/ 00:00-Intro 01:32-About JD and the Institute of Wow 07:52-What exactly is direct response marketing? 11:01-5 components of direct response marketing 22:41-About the Wow Factor vacation incentive 39:26-How to be the "UN" authority 41:52-Quick hits: best and worse of JD's career 53:00-Wrap up

    55 min

  8. OCT 1

    239. Modern Contractor Sales Process REVEALED (close more jobs starting now) - James Hatfield

    Take our 5 minute quiz and get a personalized Contractor Growth Plan here: https://trybta.com/DL239 To learn more about Breakthrough Academy, click here: https://trybta.com/EP239 The modern buyer doesn’t want to wait. They expect instant answers, real-time communication, and a seamless experience from first click to final payment. Today, Liveswitch CRO James Hatfield is on the show to talk about how create a seamless and speedy experience for customers using virtual --quoting. -- Here’s a hard reality: The modern buyer doesn’t want to wait. They expect instant answers, real-time communication, and a seamless experience from first click to final payment. But most trades businesses struggle to make that a reality for their customers. Today, I’m joined by James Hatfield, CRO at LiveSwitch, to unpack a faster, smarter way to sell—without losing the human connection. We’ll cover how expectations have shifted, where contractors are still falling short, and how to blend speed with authenticity in every step of the sales journey. If you want to win the “race to the face” and elevate your customer experience, this one’s for you. 00:00 - Intro 02:03 - History of Liveswitch 04:15 - Balancing race to face vs. personalization 07:46 - What does the modern buyer expect from a sales process? 11:02 - What does the virtual quoting experience look like for customers? 16:37 - Benefits of tech-enabled sales 24:19 - Creating a tech-enabled review/referral process 27:04 - Claiming the property with QR codes 32:16 - Does EVERY customer really prefer tech-enabled sales? 34:20 - Other tech to add to your stack 39:08 - Final thoughts and wrap up

    42 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
    246
  • Rating
    Explicit
  • Copyright
    © Copyright 2025
  • Show Website
    Contractor Evolution

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