EPISODE · May 18, 2026 · 25 MIN
From OHL Hockey to Commercial Real Estate | Young Entrepreneur Mindset | EP392
from The Real Estate Podcast · host Kormendy Trott Real Estate Team
In this episode of The Real Estate Podcast, Steve Cecchetto sits down with Jason Dasilva — OHL hockey player, CrossFit athlete, entrepreneur, and the young owner behind one of Milton’s most iconic local spots: The Ivy Arms.Jason shares how his competitive sports background shaped his mindset in business, why he decided to purchase the commercial building instead of continuing to rent, and the lessons he learned about commercial real estate investing at a young age. The conversation also dives into adapting through Covid, building strong tenant-landlord relationships, creating long-term value in real estate, and what makes The Ivy Arms such a staple in downtown Milton.VIDEO SECTIONS & TIMESTAMPS0:00 Intro2:03 CrossFit Games & Early Athletic Career4:56 OHL Hockey Journey & Guelph Storm8:31 Billet Life & Team Culture9:53 The Story Behind The Ivy Arms11:24 How The Ivy Adapted During Covid14:07 Why Jason Bought The Building17:33 How To Increase Property Value20:10 Advice For Young Investors22:27 Most Popular Food & Drinks At The Ivy25:27 OutroWatch on YouTube:https://youtube.com/kormendytrottListen on Spotify:https://open.spotify.com/show/1pwncyet9NydbgTmx5D21kLinktree:https://linktr.ee/kormendytrottInstagram:https://instagram.com/kormendytrottYouTube:https://youtube.com/kormendytrottFacebook:https://facebook.com/kormendytrottX:https://x.com/kormendytrottLinkedIn:https://linkedin.com/company/ktrealtyTikTok:https://tiktok.com/@kormendytrottThe Kormendy Trott Team was formed in 2011 by Ariel Kormendy and Adrian Trott. Originally a team of two in Milton, Ontario, KT has grown into a full-service real estate group serving Halton Region, Peel Region, and the Greater Toronto Area.
What this episode covers
In this episode of The Real Estate Podcast, Steve Cecchetto sits down with Jason Dasilva — OHL hockey player, CrossFit athlete, entrepreneur, and the young owner behind one of Milton’s most iconic local spots: The Ivy Arms.Jason shares how his competitive sports background shaped his mindset in business, why he decided to purchase the commercial building instead of continuing to rent, and the lessons he learned about commercial real estate investing at a young age. The conversation also dives into adapting through Covid, building strong tenant-landlord relationships, creating long-term value in real estate, and what makes The Ivy Arms such a staple in downtown Milton.VIDEO SECTIONS & TIMESTAMPS0:00 Intro2:03 CrossFit Games & Early Athletic Career4:56 OHL Hockey Journey & Guelph Storm8:31 Billet Life & Team Culture9:53 The Story Behind The Ivy Arms11:24 How The Ivy Adapted During Covid14:07 Why Jason Bought The Building17:33 How To Increase Property Value20:10 Advice For Young Investors22:27 Most Popular Food & Drinks At The Ivy25:27 OutroWatch on YouTube:https://youtube.com/kormendytrottListen on Spotify:https://open.spotify.com/show/1pwncyet9NydbgTmx5D21kLinktree:https://linktr.ee/kormendytrottInstagram:https://instagram.com/kormendytrottYouTube:https://youtube.com/kormendytrottFacebook:https://facebook.com/kormendytrottX:https://x.com/kormendytrottLinkedIn:https://linkedin.com/company/ktrealtyTikTok:https://tiktok.com/@kormendytrottThe Kormendy Trott Team was formed in 2011 by Ariel Kormendy and Adrian Trott. Originally a team of two in Milton, Ontario, KT has grown into a full-service real estate group serving Halton Region, Peel Region, and the Greater Toronto Area.
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From OHL Hockey to Commercial Real Estate | Young Entrepreneur Mindset | EP392
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