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.
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First, Worst, Best, & Next is a business podcast hosted by Brad Weaver, with 20 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.
About the host
Brad Weaver hosts First, Worst, Best, & Next, a business show with 20 episodes published.
Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.
Episode #20
Tyler Chesser's Playbook: Achieving $2.1M Exits and $150M Targets in a Volatile Market
Oct 27, 202546 minS0
<p>In this episode, Brad chats with Tyler Chesser, co-founder and managing partner of CF Capital. Tyler leveraged his background as a top multifamily broker to scale his portfolio and develop CF Capital into a respected partner for investors. He shares his philosophy of constant improvement and details his journey from corporate America to real estate agent in 2013 and how he built CF Capital, which today owns and operates approximately a $200 million multifamily portfolio.</p>
<p>🔑 Key Topics Covered:</p>
How reading books like Rich Dad Poor Dad and Think and Grow Rich was the catalyst for changing his financial min...
John Casmon on 'Failing Forward' and the Power of Midwest Real Estate
Oct 24, 20251h 5mS0
<p>In this episode, Brad chats with John Casmon, former marketing executive, founder and managing partner of Casmon Capital Group , and host of the top-rated Multifamily Insights podcast. John shares his journey from corporate America—where he survived two company bankruptcies that spurred his need for a "Plan B" —to a full-time real estate investor with over $140 million in multifamily investments. He also recounts the pivotal moments that shaped his investing philosophy, from his first accidental home run deal to the painful lessons of his worst investment.</p>
<p>🔑 Key Topics Covered:</p>
<p>How going through two corporate bankruptcies (at Gener...
John Wijtenburg on Transforming a $100M Resort and the CRE Growth Operating System
Oct 3, 202529 minS0
<p>In this episode, Brad chats with John Wijtenburg, founder of LXK Group, an expert in commercial real estate operations and systems, who helps investors and operators scale their portfolios while maintaining their core values. John shares his journey from an economist at Fannie Mae and an apartment broker to a successful hotel operator and asset manager, and discusses his framework for growth in the CRE space.</p>
<p>🔑 Key Topics Covered:</p>
<p>John's career path: from institutional roles to building an eight-hotel extended stay portfolio and now consulting on luxury and boutique properties.</p>
<p>The persistence of the...
John Todderud's Journey from Tech to Multifamily Syndication
Sep 24, 202532 minS0
<p>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.</p>
<...
Beyond the First Deal: Scaling a Real Estate Portfolio with Ian Cruz
Sep 12, 202534 minS0
<p>In this episode, Brad chats with Ian Cruz, a former CPA and boxing coach who has successfully transitioned into multifamily real estate. Ian shares his journey from his roots in big four public accounting to becoming a value-add multifamily investor focused on the Cincinnati, Ohio market. He discusses the importance of building a strong local team when investing out of state, the value of in-person networking, and how a disciplined approach—honed from his years as a boxer—helps him navigate the inevitable challenges of real estate.</p>
<p>🔑 Key Topics Covered:</p>
<p>How the discipline from boxing translate...
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