Entrepreneurship Episodes

WATCH ▶️ Watch this episode on YouTube *** EPISODE DESCRIPTION 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 a Master’s in Finance and graduated Summa Cum Laude...

WATCH ▶️ Watch this episode on YouTube *** EPISODE DESCRIPTION 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 vacation rentals and executive housing, Deana delivers exceptional...

WATCH ▶️ Watch this episode on YouTube *** EPISODE DESCRIPTION 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 bibidi’s vision happen. Founded in Kelowna, bibidi's mission is to conn...

WATCH ▶️ Watch this episode on YouTube *** EPISODE DESCRIPTION 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 helps high-performing real estate agents build systems, teams...

WATCH ▶️ Watch this episode on YouTube *** EPISODE DESCRIPTION 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 locations in Edmonton, Calgary, Vancouver, Toronto, and soo...

Episode 54: Matt and Taylor are joined by Brandon Love and Tom Moffat, both Mortgage Brokers at Northshore Mortgage Group from Burlington, Ontario. Brandon and Tom also co-host 2 podcasts, The Invested Entrepreneur, which helps consumers achieve financial freedom, and Commission Breath, which provides tactical information for Mortgage Brokers to scale their business. Brandon & Tom are here to discuss: → What led them to entrepreneurship and the common threads they've seen with successful e...

Episode 52: Matt and Taylor are joined by Nicole Watson, CA, CPA, TEP. Nicole is the Owner and Founder of Watson Chartered Professional Accountant Services Inc. from Kelowna, BC, which provides specialized tax advisory and compliance services clients and other CPA firms across Canada. Nicole has over 20 years of accounting experience, and has been Taylor's accountant for years. Nicole is here to discuss: → GST, CPP, dividends, when to incorporate, tax penalties, and tax deferral. → How pre...

Episode 51: Matt and Taylor are joined by Amanda Van Der Lee. Amanda is the Founder and CEO of How to Host from Kelowna, BC, and it's offshoot companies, How to Style Inc. and Sparkling Stays Inc. How to Host has become a top-rated luxury vacation rental management brand, renowned for its exceptional service and remarkable results, which thrives off of the self-sustaining How to Host ecosystem. Amanda is here to discuss: → How she founded How to Host and it's offshoot companies, How to Sty...

Episode 49: Matt and Taylor are joined by Nicholas Kusmich. Nic is the Founder of the H2H Media Group from Kelowna, BC, is best known as a Leading Digital Advertising Strategist and for having the highest ROI's in the industry (up to 30,973.32%). He has generated over $600M in revenue by creating advertising campaigns that don’t suck and allows you to generate qualified leads without a funnel. Nic is here to discuss: → How he schedules his time, the business practices he follows, and "hack...

Episode 38: Matt and Taylor are joined by Jason Henneberry. Jason is an entrepreneurial junkie from Duncan, BC, with a passion for helping real estate and mortgage pros attract and convert more clients. He’s the creator and co-founder of several widely implemented tech and finance solutions including LenderSpotlight, The VIP Club, Strategy Hub, Fundible and BrokerHQ, while also being the co-founder and COO of Tango Financial, which funds $4.5 billion annually in mortgages. Jason is here to...

Episode 28: Dean Desrosiers stops by the studio to talk about his coaching practice, becoming a partner in Century 21 Assurance, excelling as an agent and pickleball! Dean has been in sales his whole adult life and has been selling real estate since 2008. He has become a mentor in the office as well as becoming a partner in the brokerage last year. Dean has been looked up to as a mentor as long as Matt has known him but is now offering coaching to agents who are looking for it. Dean has a lot t...

Episode 9: Get your notepads ready, Matt and Taylor landed Max Carbone on podcast! Max is an owner/partner of Century 21 Assurance Realty in Kelowna BC and he is also the reason why Matt runs his real estate business out this office. Max gives his advice on a variety of topics and shares stories from his experience over the years. Starting as a young caddy working on the golf course, to selling commercial real estate, to authoring a book, to mentoring and advising top business people from all o...