First, Worst, Best, & Next
Podcast Description
First, Worst, Best, and Next Podcast is the ultimate real estate investing podcast where top investors share their most eye-opening deals—their first investment, their worst failure, their biggest success, and what’s next on their horizon. Hosted by industry experts, this show uncovers hard-earned lessons from seasoned professionals, giving listeners a front-row seat to the strategies, missteps, and triumphs that shaped their careers.
Whether you’re an experienced investor or just starting out, you’ll gain invaluable insights into multifamily and apartment investing, along with other asset classes. Learn what works, what doesn’t, and how to scale your portfolio by avoiding costly mistakes and capitalizing on proven strategies. If you’re looking to grow in the real estate investing space, First, Worst, Best, and Next Podcast is your go-to resource for expert wisdom and real-world experience.
Podcast Insights
Content Themes
The podcast focuses on key topics within real estate investing, particularly multifamily and apartment investments, with episodes that delve into asset management strategies, investment pitfalls, and scaling techniques. For example, an episode featuring Jason Yarusi explores how he transitioned from house flipping to managing multifamily properties, emphasizing strategic planning, refinancing methods, and the importance of effective communication in partnerships.

First, Worst, Best, and Next Podcast is the ultimate real estate investing podcast where top investors share their most eye-opening deals—their first investment, their worst failure, their biggest success, and what’s next on their horizon. Hosted by industry experts, this show uncovers hard-earned lessons from seasoned professionals, giving listeners a front-row seat to the strategies, missteps, and triumphs that shaped their careers.
Whether you’re an experienced investor or just starting out, you’ll gain invaluable insights into multifamily and apartment investing, along with other asset classes. Learn what works, what doesn’t, and how to scale your portfolio by avoiding costly mistakes and capitalizing on proven strategies. If you’re looking to grow in the real estate investing space, First, Worst, Best, and Next Podcast is your go-to resource for expert wisdom and real-world experience.
In this episode, Brad chats with John Todderud, the founder of Cardinal Oak Investments and a former tech professional who transitioned into multifamily real estate. John shares his journey from buying small, rural properties to scaling a full-fledged syndication business. He opens up about the biggest lessons he learned from his “worst” and “best” deals, including the pitfalls of underestimating deferred maintenance and the unexpected rewards of a long-term hold in a stable market. John also discusses his shift from individual ownership to syndication, highlighting the value of building relationships and leveraging investor capital to acquire larger assets.
Key Topics Covered:
John’s path from a tech career to full-time real estate investor.
The evolution of Cardinal Oak Investments from a personal vehicle to a syndication business.
The importance of starting small and learning from mistakes, as with his first three-unit deal.
The harsh lesson of underestimating deferred maintenance on a big value-add project.
Why a “slow and steady” deal in a recession-resistant market turned into a “home run”.
The key differences between a joint venture and a syndication, and why he chose the latter.
The current market and why patience is crucial for finding the right deals.
The value of building trust and relationships with investors as a syndicator.
💬 Memorable Quotes:
“I wanted a property that I could… learn on, essentially to make my mistakes, my small mistakes.” — John Todderud
“It’s not like you fix the roof and suddenly you can get higher rents… a lot of these things don’t translate directly into income, but they do mean a buyer… has fewer things to choke on.” — John Todderud
“I never would have expected it… just a huge pleasant surprise.” — John Todderud on his “home run” deal
🔗 Connect with John Todderud:
Website: learnaboutapartments.com
Email: [email protected]
🎙️ Connect with Host Brad Weaver:
LinkedIn: https://www.linkedin.com/in/bradweaver

Disclaimer
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