From Frat Houses to Private Islands with Mike Cossette, Ep. 728

Mike Cossette is an award-winning RE/MAX broker and co-owner of RE/MAX Gateway in Austin, TX. With over 20 years of experience, Mike has built an impressive investment portfolio of 18 properties—including multifamily units, Airbnbs, and even a private island. Known for blending lifestyle, creativity, and strategic investing, he helps clients and fellow agents scale sustainably while leveraging both real estate licenses and entrepreneurial grit.

 

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Key Takeaways

• Mike’s first house hack was a frat house—literally—with bullet holes in the roof, but it appreciated enough to fund his investing journey.

• Being both an agent and investor gave him an edge: faster access to deals, deeper market data, and commission savings.

• Scaling too quickly without stabilizing operations or budgeting for CapEx can lead to long-term setbacks.

• His private island investment was driven more by lifestyle than ROI—but it’s still appreciated significantly.

• Adaptability, multiple exit strategies, and alignment with personal life stages are key to sustainable investing.

 

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Topics

From Frat House to Financial Freedom

• Started investing in college by house hacking a four-bedroom home with his fraternity.

• Learned property management, rent collection, and legal risks the hard way.

• Despite the chaos, the home appreciated, teaching him about leverage and wealth creation.

Agent + Investor = Advantage

• Uses his license to act fast, save on commissions, and analyze market trends in real time.

• Warns that agents sometimes skip due diligence when investing for themselves—treat every deal with care.

• Highlights liability risks agents face if they don’t operate with transparency or try to “cherry-pick” deals.

Scaling Tips for Agents and Investors

• Warns against growing too fast—stabilize one deal before jumping to the next.

• Many new investors ignore CapEx and exit strategy planning.

• Focus on cash flow and structure, not just buying “a good deal.”

Investing in a Private Island

• Bought a 1.2-acre island in Florida with friends during COVID—initially as a land rental play.

• Faced challenges with permits, infrastructure, hurricanes, and tide levels.

• Currently undeveloped but used for camping, treasure hunts, and family escape—zero pressure to monetize it now.

What He’s Seeing in Austin’s Market

• Submarkets are performing very differently, even within the same price bands.

• Distressed sellers are creating negotiation opportunities not seen since 2008–2009.

• Long-term fundamentals in Austin remain strong, especially with companies like Tesla and Apple investing there.

 

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Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

Round of Insights

Failure that set Mike up for success: Bought a short-term rental in Florida that was hit by multiple hurricanes. It was initially a disaster, but insurance and creative ma