RERUN: Burned Out at 53, Retired by 59: Here's How | John D O’Leary episode artwork

EPISODE · Oct 17, 2025 · 1H 7M

RERUN: Burned Out at 53, Retired by 59: Here's How | John D O’Leary

from Build to Win · host Jonathan Weinberg & John Kolbaska

We have a question for you: do you ever feel like you’re too old, too late, or too stuck to build something big? You’re not alone; and most importantly, it’s never too late.Meet John D O’Leary: At 53 years old, he was still climbing roofs, burning out his body, and had nothing set aside for retirement. Most other contractors would have accepted that was the end of their story, but not John. Instead, he decided to pivot and ended up building a multimillion dollar business in just five years!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.Listen in now and learn:How John grew from $600k to $6M+ in just five yearsWhy customer service was his secret weaponHow he used the “knowing-doing gap” to out-execute everyone elseWhat private equity looks for, and how he checked every boxWhy building a business with an exit in mind changes everythingThis is a must-listen for any contractor wondering if they’re too far in to start thinking bigger. 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=17  ⚡ 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!

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RERUN: Burned Out at 53, Retired by 59: Here's How | John D O’Leary

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