Sign up to save your podcasts
Or
Share Scaling a Roofing Business from $600k to $6M+ (in just 5 years) | John D O’Leary
Share to email
Share to Facebook
Share to X
Share to email
Share to Facebook
Share to X
Or
Scaling a Roofing Business from $600k to $6M+ (in just 5 years) | John D O’Leary
Do you feel like you’re too old, too late, or too stuck to build something big? Think again.
At 53, John D O’Leary was still climbing roofs, burning out his body, and had nothing set aside for retirement. Most people would have accepted that was the end of their story, but not John.
In this week’s episode of the Build to Win podcast, we sit down with John to unpack how he went from grinding as a one-man crew to scaling a $6M+ roofing business and selling it for more than he ever imagined.
Together, we discuss what really changes when you go from working IN your business to working ON your business, the mindset shift that made it all possible, and how hiring smarter people freed him up to lead.
Listen in now and learn:
- How John grew from $600k to $6M+ in just five years
- Why customer service was his secret weapon (hint: red tickets)
- How he used the “knowing-doing gap” to out-execute everyone else
- What private equity looks for—and how he checked every box
- Why building a business with an exit in mind changes everything
This is a must-listen for any contractor wondering if they’re too far in to start thinking bigger. Spoiler: you’re not.
Well then, what are you waiting for?
Run, don’t walk, and tune in now!
Key Takeaways:
Introduction (00:00)
Meet John (00:30)
How John transformed his business (06:23)
Scaling secrets (15:07)
Why you need to maintain a “customer first” culture (23:34)
Let’s talk about mindset (38:56)
The power of letting go (45:39)
Additional Links & Resources:
🔥 Watch our **FREE** on-demand webinar and learn how to drive 20% net profit with systems and processes: https://www.builderprime.com/webinars/on-demand-webinar-drive-20-net-profit-with-systems-processes?utm_source=RedCircle&utm_medium=Audio&utm_campaign=7
⚡ Learn more about us: https://www.builderprime.com/
📱 Connect with us on social media:
- Facebook: https://www.facebook.com/builderprime/
- LinkedIn: https://www.linkedin.com/company/builderprime/
- Jonathan’s LinkedIn: https://www.linkedin.com/in/jonathanweinberg/
- John’s LinkedIn: https://www.linkedin.com/in/john-kolbaska-a271a757/
- Instagram: https://www.instagram.com/builderprimecrm/
—
Build to Win is a podcast for contractors where we give you the tools to grow your home improvement business. Follow us wherever you listen to your podcasts!
View all episodes
By Jonathan Weinberg & John KolbaskaDo you feel like you’re too old, too late, or too stuck to build something big? Think again.
At 53, John D O’Leary was still climbing roofs, burning out his body, and had nothing set aside for retirement. Most people would have accepted that was the end of their story, but not John.
In this week’s episode of the Build to Win podcast, we sit down with John to unpack how he went from grinding as a one-man crew to scaling a $6M+ roofing business and selling it for more than he ever imagined.
Together, we discuss what really changes when you go from working IN your business to working ON your business, the mindset shift that made it all possible, and how hiring smarter people freed him up to lead.
Listen in now and learn:
- How John grew from $600k to $6M+ in just five years
- Why customer service was his secret weapon (hint: red tickets)
- How he used the “knowing-doing gap” to out-execute everyone else
- What private equity looks for—and how he checked every box
- Why building a business with an exit in mind changes everything
This is a must-listen for any contractor wondering if they’re too far in to start thinking bigger. Spoiler: you’re not.
Well then, what are you waiting for?
Run, don’t walk, and tune in now!
Key Takeaways:
Introduction (00:00)
Meet John (00:30)
How John transformed his business (06:23)
Scaling secrets (15:07)
Why you need to maintain a “customer first” culture (23:34)
Let’s talk about mindset (38:56)
The power of letting go (45:39)
Additional Links & Resources:
🔥 Watch our **FREE** on-demand webinar and learn how to drive 20% net profit with systems and processes: https://www.builderprime.com/webinars/on-demand-webinar-drive-20-net-profit-with-systems-processes?utm_source=RedCircle&utm_medium=Audio&utm_campaign=7
⚡ Learn more about us: https://www.builderprime.com/
📱 Connect with us on social media:
- Facebook: https://www.facebook.com/builderprime/
- LinkedIn: https://www.linkedin.com/company/builderprime/
- Jonathan’s LinkedIn: https://www.linkedin.com/in/jonathanweinberg/
- John’s LinkedIn: https://www.linkedin.com/in/john-kolbaska-a271a757/
- Instagram: https://www.instagram.com/builderprimecrm/
—
Build to Win is a podcast for contractors where we give you the tools to grow your home improvement business. Follow us wherever you listen to your podcasts!