In this episode of Relentless Growth, Chase Calhoun and Jack Maher rewind to their very first real estate investments—breaking down the deals that started it all. They share what went right, what went wrong, and whether those properties are still in their portfolios.
From financing mistakes to renovation surprises, this candid conversation offers real-world insights for new investors looking to buy their first rental property or flip their first house. If you're wondering how to get started in real estate or what traps to avoid, this episode is packed with valuable lessons, practical advice, and stories from the trenches.
Topics Covered:
How we found and funded our first deals
Real estate investing mistakes we learned the hard way
What we’d do differently as first-time investors today
Advice for beginners entering the 2025 real estate market
Whether you’re just getting started or reflecting on your own first deal, this episode will leave you with actionable takeaways and motivation to keep growing.
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