First, Worst, Best, & Next

First, Worst, Best, & Next

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.

Episodes

October 27, 2025 45 mins

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 approximat...

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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 moment...

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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.

🔑 Key Topics Covered:

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    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 unexpe...

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    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...

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    In this episode, Brad chats with Bruce Fraser, a Forbes Real Estate Council Member and Managing Partner at Elkhorn Capital Partners. Bruce shares his unique journey from running a successful hedge fund for over a decade to becoming a multifamily investor. He explains how his background in macroeconomics led him to focus on hard assets, specifically distressed multifamily properties, as a hedge against inflation. Bruce also provides...

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    In this episode, Brad connects with Tenny Tolafari, a cybersecurity professional turned real estate mogul and co-founder of Xsite Capital. Tenny shares his incredible journey from working 60-hour weeks in corporate America to building and managing a $217 million real estate portfolio. He recounts the full-circle story of a cold call that led to a valuable connection, the challenges of landing their first deal, and the importance of...

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    In this episode, Brad chats with Dusty Eddy, founder of Eddy Capital Group, and a veteran real estate investor with over 23 years of experience. Dusty, who has led over $650 million in multifamily investments and completed 15 full-cycle deals with impressive returns, shares his journey from an institutional background to building his own firm. He discusses the importance of local expertise in avoiding bad deals and leveraging relat...

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    In this episode, Brad chats with Carlos Salguero, an entrepreneur and real estate expert with over 20 years of business and investment experience. After starting four seven-figure companies and exiting one for an eight-figure sum, Carlos is now focused on helping others invest in commercial real estate and building a $1 billion portfolio. He shares how his father's life inspired his interest in real estate and recounts the story of...

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    In this episode, Brad chats with Arn Cenedella, founder of Spark Investment Group, who brings over 40 years of real estate experience, including 35 years as a realtor in Silicon Valley. Arn shares his transition from single-family to multi-family real estate investing, the lessons learned from his biggest investing mistake during the 2008 subprime crisis, and his strategy for building long-term wealth. He als...

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    In this episode, Brad chats with Sam Khairi, founder of Afto Capital and a former mechanical engineer who walked away from a secure 15-year career to chase freedom through real estate and business ownership. Sam shares his journey from passive investor (LP) to active syndicator (GP), the challenges of entering the multifamily space full-time in 2022, and how he's now scaling a portfolio of small businesses with the long-term goal o...

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    In this episode, Brad sits down with Joseph Kimbrough, Marine Corps veteran turned entrepreneur, and the CEO of both Baruk Capital Group and Apex Real Estate Investments. Joseph’s journey started with door-knocking and speeding tickets—and led to creative financing on a 400+ unit deal in Phoenix. We talk wholesaling, multifamily syndications, the importance of investor communication, and why niche assets like workforce housing are ...

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    In this episode, Brad sits down with Chris Lento, founder and managing member of EM Capital Group, to hear how he went from hacking a four-unit house in East Boston to managing large multifamily syndications across the Southeast. With over 18 years of experience in multifamily real estate, Chris shares hard-earned lessons, a few war stories, and why he's bullish on creative strategies like condo conversions and cell tower contracts...

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    In this episode, we sit down with Lee Yoder, founder of Threefold Real Estate Investing, who went from physical therapist to full-time multifamily investor with over 800 units under management. Lee shares how he followed a calling to build something, overcame fear and resistance, and leaned into faith, family, and real estate to change the trajectory of his life and business.

    We dive into his first house flip, his worst and best de...

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    In this episode of First, Worst, Best & Next, host Brad Weaver sits down with Jonathan Nichols—CEO of Apogee Capital, aerospace engineer turned full-time real estate investor.

     

    Jonathan shares his transition from side-hustling real estate with his wife into full-scale multifamily syndication. From a fourplex house hack near AT&T Stadium to a 75-unit off-market home run with zero CapEx and 100% occupancy, Jonathan walks us ...

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    In this episode, host Brad Weaver talks with investor, entrepreneur, and podcast host Axel Ragnarsson, founder of Aligned Real Estate Partners and host of the Multifamily Wealth Podcast.

     

    Axel shares his journey from flipping cars in college to building a 450-unit multifamily portfolio focused in New Hampshire. He opens up about the hard lessons learned from a cash-burning out-of-state deal, the creative strategy behind his best a...

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    In this episode, host Brad Weaver talks with entrepreneur, investor relations manager, and founder of She Is Her, Jazmin Salinas. Jazmin shares her inspiring journey from immigrating to the U.S. at 19 to becoming a successful real estate investor with over 100 land transactions and 1,300 multifamily units. She dives into lessons from her early deals, her pivot into multifamily, and her exciting plans for expanded land investing a...

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    This episode features Mac Shelton from Sweet Bay Capital discussing his experiences in multifamily real estate investing. Mac shares insights into his firm's investment strategies, detailing both successes and challenges. He dives into specific deals, including his "best" and most challenging, offering valuable lessons on underwriting, market selection, and property management. The conversation explores the nuances of student housi...

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    In this episode, Will Matheson of Matheson Capital shares how he went from brokering deals to building a $100M+ multifamily portfolio across the Southeast. He walks us through his first debt deal, the challenges of navigating COVID-era operations, and the keys to scaling profitably while protecting investor capital.

     

    Will also discusses lessons from early mistakes, how his team achieved an average 47% IRR across 16 acquisitions, a...

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    In this episode, Jason Yarusi shares his journey from starting in real estate by flipping houses to scaling his business to managing multifamily properties across multiple states. He discusses the importance of strategic planning, setting clear expectations with investors, and lessons learned from both successful and challenging deals.

     

    Key Takeaways: • Strategic Planning for Investors: Jason emphasizes the importance of preparing...

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