Contractor Evolution

Hosted by Breakthrough Academy

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293

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Oct 2026

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About the show

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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October 14, 202640 min

294. Subcontractors or Employees: What’s The Better Model? - Jacob Toler

To learn more about Breakthrough Academy, click here: https://trybta.com/EP294 Take our five minute quiz and get a custom Contractor Growth Scorecard: https://trybta.com/DL294 On the surface, a subcontractor model seems like a good idea. That’s what Red Branch Construction business owner Jacob Toler thought. Higher margin, lower overhead. It worked great for him, until it didn’t. His reputation was unremarkable. His margins were thinning out. Lack of accountability almost toppled the business. And so, Jacob made a massive change that took him from negative profit to a healthy 8.5% net profit. He cut the subcontractors, restructured his office team, and hired four crews in just five months. If you’ve ever wondered whether you should switch from subs to employees or vice versa, then today’s episode will give you a great perspective. 00:00-Intro 02:05-Initial Subcontractor Model 06:47-The Warning Signs & Near-Collapse 15:28-Transitioning to In-House Employees 21:28-Recruiting & Vetting Processes 27:59-Subs vs Employees Model Analysis 35:28-Checklist for Business Model Evaluation

October 7, 202659 min

293. Why Do So Many Contractors Hate Their Business? - Spencer Sheinin

To learn more about Breakthrough Academy, click here: https://trybta.com/EP293 Take our five minute quiz and get a custom Contractor Growth Scorecard: https://trybta.com/DL293 Learn more about Spencer and Entreprenutcases: https://entreprenutcases.com/ Talk to enough contractors and you hear the same sentence. "This isn't fun anymore." Sometimes it comes from the guy who is grinding to make payroll. But just as often it comes from the guy whose business is finally working, who has the trucks and the team and the margin, and who feels absolutely nothing about any of it. Spencer Sheinin has seen both versions up close. He is a CPA, the founder of Shift Financial, and the author of Entreprenumbers. He has owned businesses since 2000, across four companies and 300 employees, and he spent roughly twenty years running work that was never really connected to him. He is now writing a book called Entreprenutcases based on interviews with owners who found real meaning in their businesses and the ones who lost it along the way. In this episode, Spencer and Danny dig into why the business stops being fun. The grind that only works for so long. The moment survival is handled and the fight disappears. And what Spencer calls robot mode, the programming that keeps us chasing bigger and faster instead of better. Then he gets practical. Three archetypes of purpose-driven businesses, two questions every owner needs to answer, and the formation moments in your own history that point to the answer. Danny gets into his own version of it too, including the year he quit painting to fly helicopters and what that taught him about being underwhelmed. Fair warning: Spencer is not here to convince anybody. If money is the whole point for you right now, he says that is fine, and he will be around when it stops being enough. Spencer is offering free live coaching on his own podcast to help owners find their purpose. Learn more at https://entreprenutcases.com/ 00:00-Intro 04:39-Root Causes of Disconnection 09:56-Recognizing Signs of Burnout 22:20-Three Archetypes of Meaning 29:21-Money vs Authentic Purpose 36:22-Finding Personal Purpose 48:02-Organizational Impact of Alignment 52:46-Practical Steps for Entrepreneurs

September 30, 202644 min

292. How To Build A Company Brain With NotebookLM - Grant Fuellenbach

Get a copy of our AI Guide For Contractors and learn the 4 highest leverage AI workflows for trades businesses: https://trybta.com/DL292 Get Grant’s free Claude skills for your business here: https://skillmatch.zite.so/ Most contractors are drowning in AI options. New tools every week. New features buried inside the tools you already pay for. No clear answer on which ones are worth your time. Grant Fuellenbach implements project management systems for contracting companies at GoFirst Consulting, and he uses AI to do it faster. He also hosts the Beyond the Bid podcast. So we asked him a simple question: what should a contractor actually be using right now? His answer was three tools, and two of them are free. Grant walks us through NotebookLM (he calls it the underserved GOAT), Prompt Cowboy, and Claude Cowork. Then he actually walks through the work, with examples: a company brain built from SOPs and training videos, an estimate pulled together from a photo and a few measurements, and an SEO audit that runs on a schedule without him touching it. If you have ever lost a night to an AI rabbit hole and come out with nothing, start here. Find Grant on LinkedIn: https://www.linkedin.com/in/grantfuellenbach or reach him at https://gofirstconsulting.com/ To learn more about Breakthrough Academy, click here: https://trybta.com/EP292 00:00-Intro 01:49-AI in Contracting & Workflows 10:01-NotebookLM & Second Brain 21:59-Prompt Cowboy & Efficiency 25:50-Claude Co-Work & Automations 31:23-Demo of NotebookLM 38:45-Final Recommendations

September 23, 202659 min

291. How To Implement AI Without Losing Your Mind [For Contractors] - Tyler Folkman

To learn more about Breakthrough Academy, click here: https://trybta.com/EP291 Get a copy of our AI Guide For Contractors and learn the 4 highest leverage AI workflows for trades businesses: https://trybta.com/DL291 Tyler Folkman has been working in the AI space for nearly twenty years. You read that right. While most of us were just getting used to having a website, Tyler was working on next level technology. Today, he’s the Chief AI Officer at JobNimbus. He helps provide roofers with the tech they need to make operations quicker, easier and more profitable. Here’s why we wanted him on the show: Many of you are starting to incorporate AI into your business. The result is that we end up wasting a ton of time going down rabbit holes that lead nowhere, maybe even putting our information at risk along the way. Today, Tyler is walking us through a clear roadmap to using AI to build systems once, properly, so you can power your business with good processes and accurate data. And if you’re not a roofer, don’t worry. Everything we discuss today is relevant to any business owner in the trades. Subscribe to Tyler’s AI newsletter here: https://www.tylerfolkman.ai/ 00:00-Intro 04:08-Contractor AI Adoption 13:30-Practical Workflows & Estimating 22:16-CRM AI Integrations 30:08-Managing Data Security Risks 40:25-Staying Current with AI 49:22-Future of AI in Contracting

September 16, 20261 hr 3 min

290. What Happens When You Sell To Private Equity? - Tyler Goodhue

To learn more about Breakthrough Academy, click here: https://trybta.com/EP290 Take our five minute quiz and get a custom Contractor Growth Scorecard: https://trybta.com/DL290 There's a lot of noise about selling to private equity in the trades right now. Some of you may even be considering this as your exit strategy. But how much do you REALLY understand what’s involved in arguably one of the biggest decisions of your life? Our guest today Tyler Goodhue has been involved in the acquisition of over 200 businesses, primarily in the trades, and he's here to discuss the part nobody talks about publicly. What actually creates value, what quietly destroys it, and how to avoid settling for a bad deal. Today, he’s walking us through what actually happens when you decide to sell to private equity. The whole process: the good, the bad and the ugly. 00:00-Intro 02:27-Why Private Equity Loves Trades 08:04-P.E. Acquisition Strategy 11:58-Factors Driving Company Valuation 24:57-Evaluating Owner Reliance Risks 38:20-Common Seller Misconceptions 46:07-Key Contract Deal Terms 53:48-Planning an Optimal Sale

September 9, 202649 min

289. How To Dominate AI Search Results (For Home Services) - Phil Risher

To learn more about Breakthrough Academy, click here: https://trybta.com/EP289 Get a free contractor Lead Source Attribution template and example here: https://trybta.com/DL289 While contractors and construction business owners are busy scrambling to get our websites ready for AI search, Phil Risher is asking a much bigger question: Will your website even matter in 3 years? Phil is a digital marketing specialist who works exclusively with contractors. He's been watching in real time as AI search puts an end to everything we thought we knew about modern marketing. Traffic is dwindling. SEO is changing. And websites... well, they might be dying. Instead, Phil says AI agents will dominate contractor digital marketing strategies in just a few years. In today's episode, Phil shares his predictions, what they mean for the construction industry, and what you need to start building today to survive the next decade. 00:00-Intro 02:03-Recent AI Shifts 03:41-Changing Website Traffic 07:32-Measuring Marketing Success 12:43-Gathering Customer Data 24:25-Building Trusted Brands 31:38-Evolving Ad Landscape 34:56-Selecting Right Agencies

September 2, 202656 min

288. The REAL Impact Of AI in Construction [And How To Prepare] - DJ Carroll

To learn more about Breakthrough Academy, click here: https://trybta.com/EP288 When ChatGPT released in 2022, we all knew the start of a new era in tech was coming. But we couldn't possibly comprehend just how much our industry was about to change. Although robotics are a few years away from replacing field labor, pretty much every other area of a contracting business has been totally disrupted. Today, I've brought on DJ Carroll, a former contractor known for scaling home service companies through disciplined AI and automation, to share his opinions on where the industry is now, where it's headed, and the skills and concepts we HAVE to understand if we want our businesses to survive what he calls the next industrial revolution. This is not a philosophical conversation. DJ gives some real, actionable advice any contractor can implement in the next week. – Learn more about DJ Carroll: https://carroll.media/about/ 00:00-Intro 04:12-Hype Versus Reality 08:28-AI Adoption & Memory Capacity 19:43-Marketing Use Cases 28:32-Building AI Ads 34:50-Adopting Voice Services 40:17-Creating Company SOPs 45:23-Upcoming AI Advancements

August 26, 20261 hr 18 min

287. How To Run Projects Like a $34M Contractor - Caleb George, Scott Kelley, Jordan Coolidge

To get the Project Management resource bundle, click here: https://trybta.com/DL287 To learn more about Breakthrough Academy, click here: https://trybta.com/EP287 Caleb George produces $34M in projects with just three project managers. Scott Kelley’s team can run a million dollar project without asking him a single question. What do these two builders have in common? Exceptional project management systems. In this roundtable discussion, I sat down with Caleb George of Chris George Custom Homes, Scott Kelley of Evolution Design Build, and Jordan Coolidge from Buildertrend to break down the difference between projects that run profitably without owner involvement and projects that require constant firefighting to cross the finish line. – Caleb and Scott are Breakthrough Academy Members who have worked with their coaches and contractor community group to achieve exceptional results. To learn more about becoming a Breakthrough Academy Member, click here: https://trybta.com/EP287 Check out Buildertrend: https://buildertrend.com/ Learn more about Chris George Custom Homes: https://www.chrisgeorgecustomhomes.com/ Learn more about Evolution Design Build: https://evobuildgroup.com/ 00:00-Intro 07:37-Biggest Contractor Issues 09:59-Broken Process Signs 15:38-Defining PM Roles 26:18-Implementing Balanced Accountability 35:49-Optimizing Project Communication 57:51-Streamlining Planning Capacity 1:12:11-Advice for Contractors

August 19, 20261 hr 1 min

286. $7M Playbook: Build A Profitable Landscaping Company - Riley Rivers

To learn more about becoming a Member, click here: https://trybta.com/EP286 Take our five minute quiz and get a custom Contractor Growth Scorecard: https://trybta.com/DL286 At just 30 years old, Riley Rivers owns a $7M dollar landscaping business, pulling in $120K in profit every month. Multiple divisions. Massive contracts. Complex operations. And he does it all in less than 40 hours a week. In this episode, I'm talking to Riley to find out how he built his company, including the key decisions he made as he scaled. If you're ready to step out of the day-to-day and become a real CEO, Riley's story is a must listen. — Riley is a Breakthrough Academy Member who has worked with his coach and contractor community to build a business he loves running. To learn more about becoming a Member, click here: https://trybta.com/EP286 Learn more about Rivers Landscaping: https://www.riverslandscapingmt.com/ Episode highlights: Learn which systems enabled Riley to more than double his revenue without sacrificing profitability. Get insight into Riley’s hiring strategies when it comes to adding high-impact leaders into his organization. Discover how Riley built his team culture… by letting his team build his culture. Find out how he stepped back and let his people establish the company’s core values and the tactics used to live them out. 00:00-Intro 01:55-Journey to $3 Million 07:12-Evolution of Roles 09:41-Strategy for Growth 11:49-Identifying Core Gaps 21:01-Org Structure Strategy 30:18-Cultivating Company Culture 40:22-Leadership and Management

August 12, 202657 min

285. The Formula For Consistent Cash Flow In 7-Figure Contracting Businesses - Bob Gauvreau

Grab a copy of Bob's Top 10 Tax Tips For Self-Employed Contractors: https://trybta.com/DL285 To learn more about Breakthrough Academy, click here: https://trybta.com/EP285 Ever run out of money despite making millions of dollars? This is the situation Bob Gauvreau has seen hundreds of contractors fall into. Revenue is up, profit may even be up. But they run out of cash unexpectedly and when they get hit with an unexpected bill or expense… …they crumple. In today’s episode, Bob walks us through a foolproof system for managing your cash flow so financial stress becomes a thing of the past. Episode Highlights: Learn why your P&L might be lying to you, and which metrics actually matter when it comes to the health of your business Understand where cash gets “stuck” and how to avoid accidentally spending the cash you need to pay the bills. Discover the foolproof system for managing your cash flow and forecasting potential issues 90 days in advance (no more being jump-scared by your bank balance) Get in touch with Bob: https://gauvreaucpa.ca/ 00:00-Intro 02:18-Cash Flow vs Profit 08:32-Tight Cash Impact 15:36-Optimizing Cash Inflows 23:04-Accounts Receivable Systems 29:38-Managing Cash Outflows 43:57-Owner Compensation Rhythm 47:24-Financial Process Organization