The Wisdom, Lifestyle & Money Show

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Rhys Wyn Trenhaile, broker and team leader of The Vanguard Team at Manor Windsor Realty Ltd. in Windsor, Ontario. Rhys shares his unique path from being a national championship-winning track and field athlete at the University of Windsor to becoming a seasoned real estate investor and broker. Starting in unive...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham welcomes Jennifer Champion and Christine Traynor from LendCity's commercial mortgage team to explore value-add strategies for multi-family apartment buildings. They emphasize shifting focus from pure cashflow to forcing appreciation through rent increases to market levels and expense reductions, which are more controllable t...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham welcomes Jennifer Champion and Christine Traynor from the LendCity Mortgages team to discuss commercial financing options for Canadian investors. Jennifer shares her journey starting as a value-add investor in New Brunswick during the uncertain times of March 2020, focusing on duplexes and fourplexes before shifting to comme...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Tom McCormick, a mechanical aerospace engineer turned real estate investor from Windsor, Ontario. Tom shares his entry into real estate during the 2020 COVID era, motivated by job uncertainty and inspired by his brother's duplex purchase near the University of Windsor. Starting with a challenging single-family hom...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham interviews Carmen Da Silva, a cross-border CPA and co-founder of SHARE, who specializes in helping Canadians invest in U.S. real estate. Carmen shares her journey from articling at PricewaterhouseCoopers (now PwC) in tax programs to building a family wealth management business, before relocating to Florida in 2003. She discu...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Derek Wormsbecker, a mortgage agent at LendCity who specializes in helping Canadians invest in US properties. Derek shares his journey from starting as a real estate investor in Canada by renting out his first townhouse, to selling properties and redeploying capital into the US market. Motivated by rising costs an...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham interviews Marc Racette, CEO and co-founder of Pulse FX, a Toronto-based foreign exchange and global payments firm. Marc shares his journey starting in international business expansion in Asia, including time in Shanghai, before entering the FX industry over a decade ago. He discusses founding Pulse FX in 2024 to provide per...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Dmitri Bourchtein, CIO and Co-Founder of SHARE, a platform that simplifies US real estate investing for Canadians. Dmitri shares his journey from starting in the debt side of real estate after university to joining Starlight Investments, where he contributed to growing a portfolio from hundreds to nearly 20,00...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham shares a streamlined approach for Canadians and foreign investors to obtain an ITIN (Individual Taxpayer Identification Number) in as little as two hours to facilitate US real estate purchases. As the president of LendCity Mortgages, Scott explains how his company, which specializes in investor-focused financing across Canad...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Milena Cardinal, founder of Cardinal Law in Ontario, about optimizing corporate structures for real estate investments. Milena explains how leveraging shareholder relationships in corporations can simplify multifamily and development projects, highlighting the benefits of a single corporation for holding investmen...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham, President of LendCity Mortgages, dives into strategies for qualifying for investment property mortgages in Canada and the USA without relying solely on personal income. He explains how investors can leverage the property's cash flow through Debt Coverage Ratio (DCR) programs in Canada and Debt Service Coverage Ratio (DSCR)...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham shares insights from his recent presentation at the WealthGenius EXPAND Investor Conference in November 2025, where over 1,100 tickets were sold. Drawing from his experience speaking to a large audience of investors, Scott emphasizes the importance of assembling the right team for real estate success. Using the analogy of no...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Andrew Kim, CEO and co-founder of SHARE, a real estate technology company specializing in US single-family rental (SFR) investments. Andrew shares his entrepreneurial journey, starting with tech startups and transitioning into real estate after discovering the advantages of the US market in 2011 while living i...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham dives into the shifting investment landscape for Canadians, highlighting why many are turning to US real estate amid economic challenges at home. Drawing from charts shared on social media and Statistics Canada data, Scott explains how foreign direct investment has been flowing out of Canada since around 2015, with a signifi...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham interviews Milena Cardinal, a real estate lawyer and founder of Cardinal Law Professional Corporation in Cornwall, Ontario. They dive into the essentials of bare trusts and GPLP (General Partner Limited Partner) structures, explaining how these tools help real estate investors navigate complex partnerships. Milena breaks dow...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Glen Sutherland, a seasoned Canadian real estate investor specializing in US properties. Glen shares his transition from investing solely in Canada to expanding into the United States, driven by limitations in Canadian lending and the desire for more scalable opportunities. Starting in 2016, he began with turn...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Jonathan Faerman, founder of Investium, a platform designed to connect real estate investors for joint ventures. Jonathan shares his journey starting with a condo purchase in downtown Montreal, which he later rented out and sold for profit. Seeking to scale into multifamily properties, he faced challenges in f...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham dives into LendCity's US lending options for Canadians and other foreign buyers interested in American investment properties. As a one-stop shop for residential and commercial lending in both Canada and the US, LendCity simplifies cross-border investing by offering competitive financing without requiring a US visa, partner,...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Alex Ciotoli, an investment-focused realtor in Windsor, Ontario, now with RE/MAX Preferred Realty Ltd. Alex shares his unique background, born and raised in Windsor to immigrant parents who built a successful structural steel business. He discusses growing up in the family enterprise, learning project manageme...

In this episode of the Wisdom Lifestyle Money Show, host Gillian Irving interviews Evan Ungar, a real estate entrepreneur, Guinness World Record holder, and author of the Amazon bestselling book Make the Decision: From Goal Setting to Goal Getting . Evan shares his remarkable background, from breaking two Guinness World Records for the highest standing box jump (63.5 inches) and highest one-leg bo...

In this episode of the Wisdom Lifestyle Money Show, host Gillian Irving interviews Monika Jazyk, a seasoned real estate investor and co-owner of RPI Education. Monika shares her background as a former teacher with a master's degree, mother of four, and how she transitioned into full-time investing over 14 years ago. Starting with buy-rent-hold properties in Northern Ontario, she and her husband bu...

In this episode of the Wisdom Lifestyle Money Show, host Gillian Irving, a mortgage agent with LendCity Mortgages, interviews Michael Matthew, a Chartered Professional Accountant with over 30 years of experience. Michael shares his expertise on helping Canadians navigate US real estate investments, drawing from his background in business consulting and his own experiences as a landlord. The discus...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Ryan Poole, owner of RealTrade and a seasoned realtor specializing in South Florida properties. Ryan shares his journey from growing up in northern Minnesota, where harsh winters and personal loss prompted his move south over 25 years ago, to building a thriving real estate career. Influenced by a mentor's advice,...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham sits down with Jeffrey Woods, a seasoned real estate investor who has been full-time in the industry since 1998. Jeffrey shares his origins as a struggling college student in Ontario, Canada, saving up to purchase his first distressed property—a bank power of sale in Hamilton. He discusses early successes renting rooms to st...

In this episode of the Wisdom Lifestyle Money Show, host Scott Dillingham chats with Nick Messina, a realtor from Team Goran at RE/MAX Care Realty in Windsor, Ontario, and Kass Dipasquale, founder and principal designer at Kass Design Studio in LaSalle, Ontario. The discussion dives into common pitfalls real estate investors face during renovations, such as personalizing spaces too much with uniqu...