Kelowna Real Estate Podcast

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Episode 120: Matt and Taylor are joined by Chase Stevenson. Chase is the Founder of CHASEIT Group from Kelowna, BC, bringing together a high-performing community, world-class coaching, and strategic investment in companies shaping the future of health and wellness. Their focus is simple: build better humans, stronger communities, and have meaningful impact.

Chase has...

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Episode 119: Matt and Taylor are re-joined by Deana Steele. Deana is the Founder of Keys to Kelowna from Kelowna, BC, the top short-term vacation rental property marketing platform in the Central Okanagan. In 2025, Deana also became an Advisory Parter of Deville Coffee Lakeshore, a local coffee shop on Kelowna's Lakeshore Road.

A trusted leader in luxury furnished va...

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Episode 118: Matt and Taylor are joined by Scott Butler. Scott is the CEO of Highstreet Ventures Inc. from Kelowna, BC, who became CEO in 2022 after being their President since 2010. 

Highstreet is the only BC-based real estate development company that develops, builds, sells, and operates net-zero (step 4) energy ready condos and rentals, while also focusing on crea...

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Episode 117: Matt and Taylor are joined by Kylee Wilson. Kylee is a Co-Founder & the Director of Community Partnerships of bibidi from the Greater Kelowna Metropolitan Area in BC, who is also a Fundraiser for UBCO. Kylee is a natural strategist who blends big-picture vision with down-to-earth care, who channels her love for people and spreadsheets into making bibid...

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Episode 116: Matt and Taylor are joined by Chad Mckillop. Chad is a Realtor with Oakwyn Realty from Kelowna, BC, who has over 20 years of experience in the real estate space. After owning a construction company specializing in award-winning custom renovations and completing 11 successful property flips, Chad obtained his real estate license, and was named Rookie of the...

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Episode 115: Matt and Taylor are joined by W. Brett Wilson, who is well known for being on CBC’s hit reality TV show Dragons’ Den, but is better known as a Canadian entrepreneur and philanthropist.

Brett co-founded FirstEnergy Capital Corp. in 1993, which went on to become Canada’s leading energy investment bank. He has since gone on to develop extensive holdings in ...

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Episode 114: Matt and Taylor are joined by Jeff Hancock & Shane Styles of Tradecraft.

Jeff is the Founder Partner of Tradecraft Consulting from Kelowna, BC, who has over 20 years of success in professional real estate, with a strong focus on development consulting and feasibility. He is the former Real Estate Services Manager at the City of Kelowna, where he was ...

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Episode 113: Matt and Taylor are joined by Ben Oosterveld. Ben is the CEO of Real Estate Reboot Coaching, while also being a business & mindset coach, keynote speaker, and best-selling author. He has lived on both sides of success, from surviving a year in rehab and life on the streets to building and selling a multimillion-dollar real estate business. Today, Ben h...

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Episode 112: Matt and Taylor are joined by Thomas Isaac. Tom is an Aboriginal Law Lawyer & Partner at Cassels Brock & Blackwell LLP from Vancouver, BC. Tom is a nationally recognized authority in the area of Aboriginal law, advising clients across Canada on Aboriginal legal matters and related environmental assessments, negotiations, and regulatory and constitu...

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Episode 111: Matt and Taylor are joined by Doug Gilchrist. Doug is the City Manager, also known as Chief Administration Officer (CAO), for the City of Kelowna from Kelowna, BC. Doug has worked for the city since 2004, and became the City Manager in 2018. The City of Kelowna is unique in it's low reliance on property taxation, which makes up only 20% of the city's billi...

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Episode 110: Matt and Taylor are joined by Paula Quinn. Paula is the Executive Director of the Downtown Kelowna Association from Kelowna, BC, who's lived here for almost 20 years after moving to Canada 25 years ago from London, England. Also A board member of WeBC, COEDC, and the Kelowna Chamber of Commerce, Paula was awarded the 2025 Kelowna Women in Business "Women o...

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Episode 109: Matt and Taylor are joined by Ben Smith. Ben is the President & CEO of Avesdo Technologies from Vancouver, BC, and a pioneer in digital marketing within the real estate development industry and more recently is leading the way for digital sales.

Having marketed more than 15,000 homes and launched hundreds of new communities, Ben's leadership in digit...

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Episode 108: Matt and Taylor are joined by Casey Greabeiel. Casey, an experienced restaurant entrepreneur from Calgary, Alberta, owns multiple restaurants in Kelowna including Salt & Brick (of which he also owns a location in Calgary), Diner Deluxe, and is a Co-Founder of Pretty Not Bad (PNB). In addition, Casey is the VP of Operations for GRETA, an arcade bar with...

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Episode 107: Matt and Taylor are joined by Patrick Bobyn. Patrick is a Partner at Pushor Mitchell LLP from Kelowna, BC, who's also the Vice-President of the Board of Directors for the Kelowna Chamber of Commerce. Patrick's practice areas are primarily business law, real estate, and financial institution security. He places an emphasis on building a trusting relationshi...

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Episode 106: Matt and Taylor are joined by Caroline Coudreau. Caroline is a CPA and Corporate Debt Advisor at Lakepoint Capital from Kelowna, BC, who relocated from Vancouver 2 years ago. Caroline joined Lakepoint Capital just over a year ago, bringing with her more than a decade of experience in commercial lending and financial analysis from her earlier career at Cana...

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Episode 105: Matt and Taylor are re-joined by Dean Desrosiers. Dean is an Owner/Partner, Associate Broker, and Coach at Century 21 Assurance Realty Ltd. from Kelowna, BC, which has been ranked one of the top 5 Century 21 franchises in all of Canada since 2019.

Dean entered real estate in 2008 and since joining Century21, he has achieved Centurion® status each year. I...

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Episode 104: Matt and Taylor are joined by Alkarim Devani. Alkarim is the CEO & Co-Founder of mddl from Calgary, Alberta, who's also the Co-Founder of the development company RNDSQR. Alkarim’s work has gained a multitude of media attention and frequently been the recipient of The Canadian Architecture Awards, MUDA Awards, American Architecture Prize, and the BILD A...

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Episode 103: Matt and Taylor are joined by Anne McMullin. Anne is the President & CEO at the Urban Development Institute (UDI), a non-profit, non-partisan association of the development industry and its related professions, who has long advocated for transformational change. Her career has spanned over 35 years as a business leader, communications executive, and jo...

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Episode 102: Matt and Taylor are joined by Rob Cupello. Rob is the Chief Strategy Officer at Csek Creative, a marketing agency that has been helping businesses tell their stories for 25 years. Rob ran his own marketing agency for 15 years before merging with NowMedia Group/Csek Creative in 2017, bringing his extensive experience in strategic marketing to every project,...