Contractor Evolution

Breakthrough Academy
  • 4.8 (65)
  • 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. 1d ago

    278. He Analyzed Over 4,000 Sales: Here’s What Kills Revenue - Ryan Fenn

    To learn more about Breakthrough Academy, click here: https://trybta.com/EP278  Get a copy of Ryan’s Lead Follow Up Formula (The Revenue Engine) here: https://trybta.com/DL278 Most contractors assume the sale is dead after two ignored messages. The data says otherwise, and the money you're leaving on the table is staggering. Ryan Fenn, founder of CHIIRP, has analyzed massive volumes of real customer conversations to find out what actually gets replies, what kills deals, and what the best follow-up systems do differently. In this episode, we break it all down into the three elements that matter most: words, cadence, and channel. You'll learn:  Why the words most contractors use in follow-up are silently killing deals — and what to say instead The data-backed timing and cadence that turns cold quotes into signed contracts Which channel (text, phone, email, video) actually converts — and when to use each one A simple dead quote reactivation system to bring stalled deals back to life Where AI is genuinely helping follow-up right now — and where it's hurting If you've ever wondered why your quotes go cold or how long you should really keep following up, this one's for you. 00:00-Intro 10:44-Follow-up in contracting  14:30-Effective sales language  29:57-Ideal follow-up cadence  44:13-Choosing communication channels  52:01-Risks of AI voice  56:05-Increasing lead conversion

    1h 7m

  2. Jun 17

    277. How To Plan And Structure Your SOPs To Delegate Literally Anything - Moustafa Moursy

    To learn more about Breakthrough Academy, click here: https://trybta.com/EP277  Take our five minute quiz and get a custom Contractor Growth Scorecard: https://trybta.com/DL277 Your crew isn't lazy. Your processes are broken. In this episode of Contractor Evolution, process strategist Moustafa Moursy breaks down why most business systems collect dust, and introduces the OPTIMIZE Framework: a step-by-step method for building SOPs that your team actually uses, so you can stop running every decision through yourself. If you've ever written a process doc that nobody followed, this episode will show you exactly where you went wrong (and how to fix it). In this episode: Why "people problems" are almost always process problems in disguiseWhat you need to define BEFORE touching any software or templatesThe OPTIMIZE Framework: Observe → Picture → Tailor → Implement → Memorialize → Zoom/EvolveThe real balance between owner direction and team input when designing processesHow to know when a process is ready to roll out (instead of endlessly perfecting it)What separates a process that gets followed from one that gets ignored (the triangle)How great processes give your team independence, not just more control Check out Moustafa’s TedX Talk: https://www.youtube.com/watch?v=SemHh0n19LA 00:00-Intro 02:21-Successful vs. Failed Processes 07:21-Defining the Optimize Framework 10:14-Step 1: Observe 15:43-Step 2: Picture 21:58-Step 3: Tailor 34:18-Step 4: Implement 45:54-Step 5: Evolve

    59 min

  3. Jun 10

    276. Micromanaging Is Costing You THOUSANDS - Matt Risinger

    Register for Matt and Danny’s upcoming team accountability web class: https://trybta.com/DL276 To learn more about Breakthrough Academy, click here: https://trybta.com/EP276  If you're the only person on every jobsite who can catch a mistake, you don't have a team; you have a daycare. In this episode, Matt Risinger (from The Build Show) maps the exact path from babysitter to system-builder, so your business runs without you hovering over every decision.  Most contractors don't even realize they're micromanaging. They just know they're exhausted, their PMs won't make a call without them, and nothing gets caught until they personally show up. This episode breaks down why smart owners get trapped as the answer guy, what it's costing them in profit and sanity, and the step-by-step framework to build a team that thinks, decides, and polices standards on its own. You'll learn: How to spot the line between managing and micromanaging, and why crossing it is a silent profit killerThe real cost of being the only person who catches mistakes (hint: it shows up in your margins, your turnover, and your ceiling)How to set non-negotiable standards your team can self-audit before you ever see the workThe exact roles and decisions a PM must own before you can truly step backA simple accountability meeting structure you can use to get real value out of every meetingHow to train independent thinking into your people without killing their ownership when they get it wrongWhat has to be true culturally before your team starts policing standards themselves 00:00-Intro 02:18-The Path to Effective Delegation 10:22-Building Loyalty & Accountability with Subcontractors 16:59-Communication & Standards for On-Site Teams 25:19-Defining Roles & Learning from Mistakes 31:55-Structuring Effective Accountability Meetings 36:50-Training for Independence & Mentorship 48:28-Philosophy on Leading & Treating People

    52 min

  4. Jun 3

    275. Stop Scrambling for Payroll: The 90-Day Cash Flow System for Contractors - Danny Kerr

    To learn more about Breakthrough Academy, click here: https://trybta.com/EP275  Download your free Cash Flow Resource Bundle here: https://trybta.com/DL275 You're winning jobs, billing strong — and still sweating payroll every two weeks. Cash timing slips. Payroll doesn't. Here's how to fix it. In this episode, Danny Kerr breaks down the exact cash flow management system BTA has used with 1,900+ contractors to stop the financial panic and start projecting 90 days ahead, so you can make growth decisions with intention, not desperation. What you'll learn: The 5 cash flow killers quietly draining your roofing contractor business (weak deposits, slow collections, and more)How to build a simple weekly cash flow system — so you know what you can spend before you hire, buy, or marketHow to project your cash position 90 days out and spot payroll pressure before it hitsThe financial benchmarks $10MM contractors actually useHow to stop playing financial roulette and build real confidence in your numbers Whether you're at $1M or pushing $10M, cash flow management isn't optional — it's the difference between scaling and gambling. 00:00-Intro 09:32-Developing Annual Budgets 19:20-Effective Job Costing 23:48-Industry Profit Benchmarks 28:04-Strategic Cash Flow 32:28-Avoiding Cash Flow Destroyers 41:22-Using Cash Flow Projections 53:43-Expense and Overhead Q&A

    1 hr

  5. May 27

    274. He Grew a Gutter Company to $6.5M Using This Mindset - Jason Alcott

    To learn more about Breakthrough Academy, click here:https://trybta.com/EP274 We’re actively working with ~600 contractors, and a LOT of them are struggling — and it's not the economy. Breakthrough Academy coach Jason Alcott reveals the hidden mindset trap keeping contractors stuck, and the one framework that changes everything. Most contractors are measuring their success the wrong way. They're locked in "the gap,” constantly chasing an ideal that keeps moving, instead of looking back at how far they've actually come. In this episode, Jason Alcott (BTA coach and former contractor who scaled Weatherguard Gutters to $6.5M with 25 staff) breaks down Dan Sullivan's Gap and the Gain framework and why fixing your mindset is the prerequisite to every system, every strategy, and every team decision you'll make this year. In this episode: Why 70% of the contractors Jason works with are having a rough year— and what's really behind itThe "Gap vs. Gain" framework that stops the overwhelm spiralHow your mindset as an owner trickles down and silently kills team moraleWhy tactics fail when mindset isn't addressed firstHow to set 90-day goals your team actually cares about (leading vs. lagging indicators)Gratitude as a stress management tool — and why it's more powerful than you think About Jason Alcott:  Jason is a Breakthrough Academy coach and former BTA member who scaled a gutter contracting business to $6.5M before joining the coaching side. He currently coaches 25+ contractor businesses and is actively helping them navigate one of the toughest business climates in recent memory. 00:00-Intro 06:22-Why do we ignore mindset? 10:44-Gap versus Gain 15:29-Shifting your headspace 27:27-Setting activity goals 29:35-Implementing the Gain mindset

    36 min

  6. May 20

    273. He Worked 90 Hours In A Week. Here’s What Happened - Chris Bailey

    To learn more about Breakthrough Academy, click here: https://trybta.com/EP273  Take our five minute quiz and get a custom Contractor Growth Scorecard: https://trybta.com/DL273 Have you ever pulled a 60-hour work week and felt like you got nothing done? Productivity researcher Chris Bailey ran a radical experiment—working 90 hours one week, 20 the next—just to see what would happen to his output. The results challenge everything contractors believe about grinding longer to get ahead. In this episode of Contractor Evolution, Chris Bailey (author of Intentional) breaks down what his 90-hour vs 20-hour productivity experiment revealed about how work smarter not harder actually works. If you're running a contracting business and burning 60+ hours a week in the trenches, this conversation will show you why more hours ≠ more results—and give you practical methods for how to get more done in less time without sacrificing your margin or your mental health. What you'll learn:  The surprising results of Chris Bailey's 90-hour productivity experiment Why working longer hours actually destroys your output (and the data that proves it)How to transition from "warrior" mode to "system-builder" mode in your businessSimple, research-backed methods for intentional productivity The real cost of contractor burnout—and how to prevent it Why the most productive contractors work fewer hours, not more Whether you're stuck in the trenches or building systems to scale, this episode will change how you think about time, energy, and what it actually takes to grow a profitable contracting business. 00:00-Intro 02:12-Addiction to Distractions  03:55-Impact of Tech on Focus  09:51-Lessons from Boredom Experiment 17:08-The Power of Wandering in Leadership 20:00-Busyness Versus Productivity  28:17-Training Brain Presence  31:51-Sleep and Productivity Myths

    54 min

  7. May 13

    272. Negotiating Contracts With AI Can Cost You Millions - Megan Shapiro

    To learn more about Breakthrough Academy, click here: https://trybta.com/EP272  Grab a copy of Megan’s OWN Your Contracts QuickStart Guide: https://meganshapiro.kit.com/590f12c899 Check out Megan’s Negotiation Style Quiz: https://meganshapiro.kit.com/81045b49f1 If you’ve thought about using AI to make the process of drafting, reading, and negotiating contracts easier, you’re not alone. But according to today’s guest, relying on AI for your contracts could be a costly mistake. Because the reality is: AI is only as good as the knowledge of the user. In this week’s episode of Contractor Evolution, we sit down with construction lawyer Megan Shapiro to break down what’s actually happening inside the agreements you’re signing, and how to negotiate them in a way that makes you more profit, keeps you out of legal trouble and empowers you to safely incorporate AI where appropriate. You’ll learn: The biggest contract clauses that quietly kill your marginsHow to spot red flags (before they cost you)A simple three part framework to review and negotiate contracts with confidenceWhere it’s appropriate to use AI in your negotiations (and where it can trigger a legal disaster) 00:00-Intro 05:49-Trade Contractor Contract Rights  07:22-Risks and Common Pitfalls   10:16-Introducing The OWN Framework  17:13-Weighing Specific Contract Provisions  29:29-Change Orders And Delays   39:27-Healthy Professional Negotiation Strategies   47:53-AI In Contract Management

    57 min

  8. May 6

    271. How To Land $100K+ Projects Without Bidding Against Competitors - John Malanchuk

    To learn more about Breakthrough Academy, click here: https://trybta.com/EP271 Get a copy of John’s slide deck here: https://trybta.com/DL271 If you’re relying on leads coming in… you’re already behind. In this episode, Breakthrough Academy Member John Malanchuk breaks down a proven approach to business development for contractors; one that goes beyond marketing and sales, and focuses on building real relationships that generate consistent, high-value work. Drawing from nearly 20 years in the commercial painting space and five years in the Breakthrough Academy contractor coaching program, John shares exactly how he: Builds long-term relationships with decision-makers (not just bids against competitors)Lands $100K+ projects through simple, repeatable outreachUses networking, presentations, and follow-ups to create predictable revenueTurns one meeting into multiple project opportunitiesStructures his CRM and pipeline to stay organized and consistent This isn’t theory—it’s a boots-on-the-ground system you can start using immediately, whether you're in commercial or residential contracting.   Key Takeaways: Business development is proactive relationship building, not reactive sellingThe goal is to get in before projects go to bid and become the trusted go-toConsistency beats intensity—just a few hours per week can transform your pipelineYour network is your biggest asset—leverage suppliers, GCs, and existing contactsFollow-up is everything (and most contractors fail here) 00:00-Intro 03:10-Target Diverse Commercial Verticals  11:40-Residential Business Development Strategies  16:36-Effective Practical Networking Tactics  20:28-Key Success Tracking Metrics  23:30-Avoiding Common Followup Mistakes  28:19-Real World Project Examples  38:46-Implementing CRM Pipeline Systems

    47 min
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4.8
out of 5
65 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 - 2026
  • Episodes
    278
  • Rating
    Clean
  • Copyright
    © Copyright 2025
  • Show Website
    Contractor Evolution

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