In this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham interviews Jill Wingler and Steve Popovich from the Joe Conlon Real Estate Team at Royal LePage Binder Real Estate in Windsor, Ontario—a top 1% team in Canada. Jill shares her journey: growing up in Windsor-Essex (moving every 2-3 years, living across areas like Belle River/Tecumseh), teaching for six years in London before joining Joe (who dated her sister, arriving in a green clover car/poncho). She focuses on families/east end niches (Lakeshore/Belle River), emphasizing market education to manage emotions in bidding wars. Steve recounts his Saskatchewan roots, music career (Canadian Idol top 40 twice, touring band), bartending/retail, and Windsor move—recruited by Joe after impressing with hustle. He enjoys first-time buyers/downsizers, stressing speed in 2025's fast market (listings sell in 3-4 days).
The team (six agents, four admins) promotes fun dynamics, social media contests (e.g., Nintendo Switch, Cedar Point tickets), and proactive tips: avoid overbidding, pre-inspections. Amid 2025's Windsor outlook (CMHC forecasts modest growth with averages ~$600K, border reopening/hospital boosting affordability post-BoC cuts to 2.25%), they highlight Windsor's value (most affordable city) and opportunities (e.g., Walkerville office in historic house). Funny anecdotes include Joe's back-flip fail/head crack. This episode offers relatable insights for buyers/sellers navigating 2025's competitive scene (rents up 4-6% YoY per Rentals.ca), motivating with stories of teamwork and market savvy.
Guest Bio
Jill Wingler and Steve Popovich are agents with the Joe Conlon Real Estate Team at Royal LePage Binder Real Estate in Windsor, Ontario—a top 1% team nationally. Jill, a former teacher, specializes in families/east end areas (Tecumseh/Lakeshore/Belle River), drawing from her Windsor upbringing. Steve, a former musician (Canadian Idol top 40), focuses on first-time buyers/downsizers, leveraging people skills from touring/bartending. The team emphasizes education, speed, and fun marketing. Connect at realtorsforlife.ca, on Facebook at facebook.com/joeconlonrealtor, Instagram @joeconlonrealtor, or call 519-735-7222 for Windsor-Essex services.
Jill Wingler and Steve Popovich are agents with the Joe Conlon Real Estate Team at Royal LePage Binder Real Estate in Windsor, Ontario—a top 1% team nationally. Jill, a former teacher, specializes in families/east end areas (Tecumseh/Lakeshore/Belle River), drawing from her Windsor upbringing. Steve, a former musician (Canadian Idol top 40), focuses on first-time buyers/downsizers, leveraging people skills from touring/bartending. The team emphasizes education, speed, and fun marketing. Connect at realtorsforlife.ca, on Facebook at facebook.com/joeconlonrealtor, Instagram @joeconlonrealtor, or call 519-735-7222 for Windsor-Essex services.
Key Takeaways
- Jill's path: From teaching in London to joining Joe (sister's ex, funny clover car stories)—highlights family focus, market education to avoid emotional overbidding.
- Steve's background: Saskatchewan musician to Windsor realtor—recruited by Joe's "door kick" for hustle; enjoys buyer/downsizer niches.
- Team structure: Six agents (jacks-of-all-trades), four admins—fun dynamic, social contests (Switch/Cedar Point), Walkerville office nod to Joe's roots.
- Market tips: Speed essential in 2025's fast sales (3-4 days)—pre-inspections, level-headed offers; Windsor remains affordable amid border reopening/hospital growth.
- Funny moments: Joe's back-flip hotel fail/head crack—team trips build bonds.
- 2025 outlook: CMHC predicts stability (averages ~$600K), BoC cuts (2.25%) easing—opportunities in east end/Walkerville.
- Advice: Buyers—education first; sellers—leverage team for wins in bids.
- Universal: Relationships key; proactive planning beats reactive regrets.
- (00:09) - Welcome and Introduction
- (03:37) - Jill's Journey to Real Estate
- (07:31) - Transition to Steve
- (11:38) - Steve's Musical Background
- (13:14) - Naked News Experience
- (16:32) - Tips for Buyers in a Competitive Market
- (17:15) - Conclusion and Contact Information
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