In this episode of Tax Sale Insiders, Brian Seidensticker, CEO of Tax Sale Resources, interviews John Casmon, a multifamily syndicator who transitioned from a corporate marketing career to managing over $150 million in real estate investments.
While the conversation veers from traditional tax sale topics, the insights are especially relevant to investors looking to move beyond single-property acquisitions into scalable, passive-income strategies like real estate syndication.
From Corporate Marketing to Real Estate: The Unexpected Journey
Before entering the world of multifamily investing, John Casmon spent 15 years in corporate marketing. He held roles with industry giants such as Nike, Mountain Dew, and General Motors. It was during his time at GM—specifically during the company’s bankruptcy in 2009—that Casmon had his financial wake-up call.
Witnessing the collapse of a major corporation firsthand underscored the risk of relying on a single income stream, prompting him to seek a more secure financial future.
Real estate initially served as a hedge.
Casmon began modestly by purchasing two and three-unit properties.
These small multifamily properties provided him with essential on-the-ground experience and a better understanding of operational management.
His early success convinced him to pursue more complex investment strategies, but scaling was not straightforward.
A Strategic Pivot from Brand Building to Property Investing
Casmon’s plan was to use flipping as a way to generate capital for larger multifamily acquisitions.
He partnered with a developer to renovate bungalow-style homes on the north side of Chicago, where the strategy involved full second-story additions to maximize resale value.
Initially, the model seemed well-structured: multiple projects at different stages, trolley tours for investors, and a clear renovation process.
However, problems surfaced quickly. The developer failed to scale the labor force with the growing number of projects, and the financial structure relied heavily on project-to-project draws, essentially shifting money from one deal to fund another. When delays occurred or a property failed to sell at the expected price, the entire system began to unravel.
Adding to the challenge, the comps used to justify resale prices were all from the developer’s previous projects. When the broader market softened, the ARVs couldn’t be supported, and profits vanished.
Casmon was left dealing with unfinished projects, unpaid contractors, and mounting stress, especially since this coincided with the loss of his full-time job and the impending birth of his second child.
Flipping Failures That Fueled Future Success
The financial strain from the failed flip projects created a domino effect, but it also clarified what not to do. Casmon’s key takeaways included the importance of thoroughly vetting partners, understanding the operational limits of construction teams, and being cautious of financial setups that resemble Ponzi-like structures.
He also recognized that speculative strategies, such as flipping, exposed him to risks that were outside his control.
In contrast, properties with existing cash flow allowed for better stability and long-term planning. These experiences underscored the value of aligning investment strategies with sustainable, repeatable systems—a mindset that eventually brought him to real estate syndication.
One personal turning point came from a conversation with a coach, who told him he was “failing forward.” While the phrase initially felt dismissive, Casmon later realized that every mistake was laying the groundwork for a more refined investment approach. The failures, though costly, were essential in developing the operational discipline required in larger-scale projects.
Unlocking Multifamily Wealth: Inside the World of Real Estate Syndication
Why Multifamily Outperforms Flipping in Scale and Stability
Casmon’s first multifamily property beyond his small two and three-unit buildings was an eight-unit property. His next deal, a 192-unit complex, was a syndicated investment in which he partnered with other investors. This marked a significant turning point in his investment career.
Multifamily assets provided several distinct advantages over flips.
First, these properties generated cash flow from day one, unlike flips, which consumed capital with the hope of a future payout.
Second, multifamily assets allowed for long-term equity growth and appreciation through value-add strategies, such as improving operations, renovating units, and increasing rents.
Third, these deals offered tax advantages, including depreciation and interest write-offs.
In Casmon’s experience, multifamily investing offered a more sustainable and repeatable path to wealth creation—one that aligned well with his goals for passive income and scalability.
Understanding the Syndication Model
In a syndication, two groups of stakeholders make the deal work: General Partners (GPs) and Limited Partners (LPs).
General Partners are responsible for identifying opportunities, underwriting deals, securing financing, and managing the property.
Limited Partners contribute capital to the deal but remain passive. They share in the profits without being involved in the day-to-day operations.
Casmon described this structure as ideal for professionals who want real estate exposure without managing tenants, contractors, or maintenance issues. GPs handle everything from deal sourcing to operations, while LPs benefit from ownership, cash flow, and appreciation.
Casmon also emphasized that these deals are structured under securities regulations. Most fall under SEC Rule 506(b) or 506(c).
The former allows both accredited and sophisticated investors to participate (provided there's a prior relationship), while the latter restricts participation to accredited investors but allows for public advertising.
For investors seeking passive income through real estate, syndication provides an opportunity to benefit from large-scale assets while outsourcing operational responsibilities to experienced teams.
How Everyday Investors Can Participate in Large Apartment Deals
Casmon’s firm, Casmon Capital, structures deals so that everyday investors can participate. For 506(b) offerings, participants need to demonstrate investment sophistication, even if they aren’t accredited. For 506(c) offerings, accreditation is required.
All offering documents, pro formas, and risk disclosures are prepared by attorneys, and investors have the opportunity to ask questions before committing capital. Distributions are typically made quarterly, with detailed operational updates along the way.
Lessons Learned and Advice for Aspiring Passive Income Investors
Vetting Partners and Spotting Red Flags
From his flipping experience, Casmon learned to pay close attention to how potential partners answer difficult questions. A dismissive attitude—such as “Don’t worry about it”—should be seen as a red flag.
He emphasized that investors should always trust their intuition and probe into areas of concern. Whether it’s a developer, a property manager, or a syndication sponsor, open and honest communication is non-negotiable.
Casmon recounted a situation where a developer was managing multiple flips without expanding his team. The investor base was growing, projects were stalling, and funds were being shifted between properties—an unsustainable system that led to failure.
Mindset Shift: From "How?" to "Who?"
A major turning point in Casmon’s approach came from the book Who Not How by Dan Sullivan. Rather than asking how to solve every problem personally, he now focuses on identifying the right person to handle the task.
Whether you're trying to navigate real estate tax sales in Florida or evaluate a large apartment deal, finding experts to guide the process is often more effective than trying to master every detail yourself.
Casmon applies this mindset across all areas of his business, as well as his personal life, from working with tax professionals to improving his coaching of youth sports.
How to Start Your Multifamily Investing Journey
Casmon offers a free guide titled 7 Questions to Ask Before Investing in Apartments. He also hosts the Multifamily Insights podcast, which features interviews with operators, analysts, and industry professionals covering deal structure, underwriting, capital raising, and more.
Additionally, the Tax Sale Resources Research platform provides data on tax sale properties where investors can find multifamily deals for below-market rates.
Final Thoughts
John Casmon’s career arc, from corporate marketing executive to managing over $150 million in real estate syndications, is a model of strategic adaptation.
His transition from flipping to multifamily was built on real-world lessons, financial pressure, and an unwavering focus on long-term security.
For tax lien and tax deed investors seeking scalable, passive strategies, multifamily syndication offers a path to sustained income and diversified assets. With the right partnerships, due diligence, and mindset, investors can move beyond transactional deals and into long-term wealth-building.
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