playnext.fm

The Truth About Real Estate Investing... for Canadians

From Florida Fixer-Uppers to Muskoka Vacation Resort for 70 With Rachel Holden

·1 hr 26 min·5 clips
A Vancouver condo investor was shocked to see Dallas properties at $200K renting for $1,800 a month.
The episode begins with host Erwin Szeto promoting a U.S. investing workshop and teasing the interview with guest Rachel Holden. Rachel introduces herself, sharing her background growing up in Windsor and moving to Toronto for an advertising career, where she worked at top agencies like TBWA and McCann on major accounts. She explains her transition into real estate, starting with a pre-construction condo and a duplex in Toronto. Rachel details her bold move to Florida in 2011, buying seven properties with a five-month-old baby during the post-financial crisis downturn, highlighting lessons about neighborhood due diligence and pro forma skepticism. She then discusses returning to Ontario to invest in garden suites, facing significant municipal pushback and regulatory changes that hampered the business. The conversation shifts to her current venture: a nine-unit resort on Lake Muskoka, which she operates as a licensed commercial business to avoid short-term rental volatility. Rachel describes marketing strategies like targeting sports teams for off-season bookings and her involvement with local tourism boards. She also outlines her plans for launching an ethical property management service called Caraden Management and her broader vision through Uplift Ventures to combine profit with social impact, focusing on housing's role in health determinants. Throughout, Rachel reflects on challenges like interest rate hikes, construction stress, and balancing entrepreneurship with family life.

As heard by us

A grounded review of how lot rules and infrastructure costs can change a property's investment case.

Property investing feels less abstract as Rachel works through the practical limits of adding a small secondary unit: lot dimensions, setbacks, fire barriers, and the heavy upfront cost of bringing plumbing, heating, cooling, and hydro to the site.

Read the full review in PlayNext →

Why you'd press play

You want property math with dirt under its fingernails, from tight backyard builds to U.S. income properties with the numbers laid bare.

Read the full recommendation in PlayNext →
Listen to the show on
Apple PodcastsSpotify
Play clips from this episodeMore from The Truth About Real Estate Investing... for Canadians