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Contractor Evolution

Contractor Evolution

By: Breakthrough Academy
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Summary

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.

Copyright 2025
Art Economics Leadership Literary History & Criticism Management & Leadership Personal Development Personal Success
Episodes
  • 298. How He Scaled From $500K to $5M (A Real Contractor’s Roadmap) - Brandon Smith
    Nov 11 2026

    Get a copy of the episode transcript: https://trybta.com/Transcript298


    Get a copy of our Contractor Success Roadmap and see how 13+ contractors scaled to 7-figures (without working more hours): https://trybta.com/DL298


    To learn more about Breakthrough Academy, click here: https://trybta.com/EP298


    In 2015, Vancouver-based contractor Brandon Smith was doing about $500K a year. Along with his business partner, he was handling sales, running production and estimating his own jobs.


    Eleven years later, he runs a $5M company.


    The road between those two numbers wasn't a straight line.


    There was a declined debit card at Quiznos, an eight-foot whiteboard that looked like a murder board, and a global pandemic that threw a wrench in the plan.


    In this episode, Brandon walks through the exact zig-zagging path he took to go from operator of a 6-figure construction business to the CEO of an award-winning company with time and money to give back.


    He also shares the one piece of advice from Danny he still hasn't forgotten: move faster.


    If you're stuck at a lower revenue than you want to be at, this episode is for you.


    Want Brandon's full sales process? Follow him on Instagram @buildwithbsmith and send him a DM that says "breakthrough." You can also catch his podcast: https://open.spotify.com/show/6lPo3hHrreDSuz6v4MhikA?si=twW4mktVTxqcH2Nec8AxHA&nd=1&dlsi=71a45319798646cc


    00:00-Intro

    06:01-From Laborer to Business Owner

    07:48-Early Financial Struggles

    11:06-Scaling to the $1M Mark

    17:10-Growing from $1M to $2M

    23:53-Leadership Growth for Scaling

    30:49-Business Lessons Learned

    40:01-What Not to Sacrifice for Business

    Show More Show Less
    46 mins
  • 297. Why Your Managers Keep Asking You What To Do - Perry Holley
    Nov 4 2026

    Book an implementation call and join thousands of contractors like Jason in running a better business while working less: https://trybta.com/DI1026


    To learn more about Breakthrough Academy, click here: https://trybta.com/EP297


    Take our five minute quiz and get a custom Contractor Growth Scorecard: https://trybta.com/DL297


    You promoted your best salesperson to run sales. Now they are in your office three times a day asking what you would do.


    That is not a hiring mistake. Perry Holley says it is a development gap, and most owners skip right past it without knowing.


    Perry is an executive coach with Maxwell Leadership, and he has worked with the BTA Community at Winter Summits and retreats for years. He was on the show back in Episode 132 breaking down the 5 Levels of Leadership. He is back to tackle the level that trips up almost everyone: becoming a developer of people.


    He walks Danny through seven steps that have to happen before anyone is actually empowered. Recruit, position, model, equip, develop, empower, measure. When somebody keeps coming to you for answers, Perry says go back through the first five and find the one you skipped.


    The step most owners miss is development. Equipping is teaching the job. Developing is teaching someone to lead themselves: time management, priority management, emotional management, resilience. Skills your crew leads were almost certainly never taught.


    Danny gets into his own version of this with the person now running BTA’s sales team, and what their January review surfaced.


    Perry also covers accountability as ownership rather than blame, why the goal rarely changes but the plan usually does, and the question that tells you whether your team trusts you: are they telling you hard things, or only the good stuff?


    And if your own development has stalled, his answer is irreducible minimums. Fifty words a day. Two pages a day. Small things done daily, consistently, compounding into something you could not have planned.


    Follow Perry Holley and the Maxwell Leadership Podcast for more on this: https://www.maxwellleadership.com/podcast/


    00:00-Intro

    02:24-Executor to Leader Transition

    09:43-7 Steps to Team Empowerment

    15:50-Developing Self Leadership & Management

    19:43-Being a Genius Maker

    26:35-Accountability as Extreme Ownership

    34:56-Final Takeaway

    Show More Show Less
    39 mins
  • 296. How $10M Contractors Keep Crews Busy All Winter (Roundtable) - Mason Marquis, Joe Kelly, Toby Woodiwiss, Luke Hansen
    Oct 28 2026

    Get the free templates from this session here: https://trybta.com/DL296


    Book an implementation call and join thousands of contractors like Jason in running a better business while working less: https://trybta.com/DI1026


    To learn more about Breakthrough Academy, click here: https://trybta.com/EP296


    Winter is the season most contractors brace for. These four have stopped bracing.


    This is the replay of our October Marketing and Sales Roundtable, where Danny sat down with three painting contractors running between $5 and $10 million and the founder of CompanyCam.


    Joe Kelly went from $3.5 million to $10 million in three years at JK Paint in Portland, and he keeps all ten crews working through December and January.


    Mason Marquis runs one of the largest residential painting companies in Dallas, and his winter discount season produced a better gross margin than his busy season.


    Toby Woodiwiss has been building Woodiwiss Painting in California since 2004, holds a net promoter score of 100, and runs at 46% gross profit. Luke Hansen founded CompanyCam after years in roofing.


    Here is what they talk about:


    • The numbers each of them watches weekly, and why every one of them named booked appointments as the earliest warning sign
    • How to tell the difference between passive and active lead sources
    • Which levers you can actually pull when flow dries up.


    00:00-Intro

    04:25-Meet the Panelists

    17:06-Signs of Broken Sales Process

    28:34-Winter Playbook & Data Tracking

    48:18-Off-Season Crew Tactics

    1:03:07-Turning Leads to Booked Work

    1:28:22-Final Advice

    Show More Show Less
    1 hr and 46 mins
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