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Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investing Morning Show ( REI Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investing Morning Show ( REI Investment in Canada )
Mark Ainley shares his journey from BRRRRs to running GC Realty, scaling property management in Chicago, and lessons from 20+ years in real estate.In this episode of RealDealChat, Jack sits down with Mark Ainley, co-founder of GC Realty & Development, co-host of Straight Up Chicago Investor Podcast, and long-time property manager and investor.Mark shares how he transitioned from house hacking and BRRRR deals to running one of Chicago's largest property management firms. He explains why property management is often overlooked, how to avoid common investor mistakes, and why focus and systems (like EOS) have been crucial for scaling.Here's what you'll learn in this conversation:How a condo house hack sparked Mark's real estate careerThe story of founding GC Realty & continuing after tragedyLessons from doing 482 BRRRR deals between 2008–2010Why focus beats chasing shiny objects in real estateCritical mistakes: not hiring fast enough, skipping processesThe role of property management in investor successWhy alignment between landlords & managers mattersChicago-specific challenges: red tape, property taxes, regulationsWhy C/D class investing creates 9x more “touches” than A/B classThe growth of Straight Up Chicago Investor Podcast & power of community
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investing Morning Show ( REI Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
In this milestone 100th episode of the Canadian Private Lenders Podcast, hosts Ryan MacNeil and Neal Andreino are joined by guest Chandler Haliburton—real estate investor, landlord, and past co-host of the Master Keys Podcast.Together, they take a deep dive into the current state of the Canadian real estate and private lending markets. From shifts in multi-unit valuations and softening condo demand to rising vacancies and cooling rents, the conversation unpacks where the opportunities and risks lie in 2025. Chandler shares first-hand experiences using private financing to scale his portfolio and highlights why even seasoned, high-net-worth investors lean on private capital.The trio also explores:Where first-time buyers still have value in HalifaxHow flips and BRRRR strategies have evolved in today's marketVariable vs fixed mortgage strategies heading into a major renewal waveSmart refinancing plays and the importance of cash flow disciplineWhy private money isn't just a last resort, but a strategic tool for serious investorsShow Notes:00:00 – Celebrating 100 episodes with guest host Chandler Haliburton04:00 – Market update: softening condos & multi-units, where buyers can find deals07:30 – Rental market realities: vacancies, rent rollbacks & balanced supply13:30 – Private financing in action: using seconds & equity to scale20:00 – Flips, BRRRRs & long-term holds in today's market25:00 – First-time buyer opportunities & Halifax's growing appeal33:00 – Variable vs fixed mortgages: strategies heading into renewal season38:00 – Smart refinancing plays & cash flow management44:00 – Build-to-rent opportunities and long-term strategyPacked with insights, anecdotes, and laughs, this landmark episode is both a reflection on the last 100 shows and a forward-looking roadmap for investors navigating the next cycle.Resources:Keystone Capital GroupCPLP Instagram: @cplpodcastKeystone Instagram: @keycapgroupFind Neal On:Instagram: @neal.andreinoLinkedIn: Neal AndreinoFind Ryan on:LinkedIn: Ryan MacNeilE-mail: ryan@keycap.ca
Real Estate Investing Morning Show ( REI Investment in Canada )
Real Estate Investing Morning Show ( REI Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investing Morning Show ( REI Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investing Morning Show ( REI Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investing Morning Show ( REI Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
In this episode of Canadian Investing in the US, Glen Sutherland welcomes back CPA Kristopher McEvoy for another installment of their monthly accounting Q&A series. Kristopher, a Canadian accountant based in Fonthill, Ontario, specializes in cross-border taxation and real estate investing. He tackles a key question from investors: when should you start using QuickBooks Online (QBO)? While newer buy-and-hold investors may get by with spreadsheets initially, Kristopher explains that investors with more complex operations—like flips or BRRRRs—need proper systems early on to track profitability and stay tax-compliant. Kristopher emphasizes that accounting software like QBO not only helps with tax filing but also enables better business management through automation, delegation, and financial reporting. He highlights the unique nuances of real estate bookkeeping, such as capitalizing interest during renovations and correctly categorizing repairs vs. improvements. For growing investors, Kristopher's firm, LEAP ACT, offers flat-fee bookkeeping services that scale with volume, making it especially valuable for those managing multiple deals. Listeners can connect with him at leapACT.ca and are encouraged to mention the podcast when reaching out.
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )
Real Estate Investor Dad Podcast ( Investing / Investment in Canada )