Cocktails & Cash Flow

An evening at Del Frisco's Double Eagle Steakhouse for professionals exploring short-term rentals as a tax and wealth strategy.

If you're a high earner watching most of your bonus and wages disappear to taxes, and you've wondered whether a short-term rental could actually move the needle, this event is built for you.

We're hosting the 5th event in this investor dinner series at Del Frisco's Double Eagle Steakhouse for craft cocktails, hors d'oeuvres, and a candid walkthrough of one real property: a $735K A-frame in Bailey, Colorado that generates $200K+/year in gross revenue. You'll see the actual acquisition strategy, the financing structure, and the tax treatment that makes the numbers work, presented by the owner/operator, the lender, and the CPA who've worked on the deal.

Featured Speakers:

Michael McClearn, Founder & CEO of StayRate, a Colorado short-term rental revenue management company overseeing 65+ luxury properties across the state. Licensed real estate agent at Good Neighbor Realty, specializing in STR investment properties. Michael will walk through his personal A-frame in Bailey from acquisition to $200K+/year: The aquisition strategy, pricing playbook, the systems, and the numbers most owners never see.

Alex Reid, Top 100 Mortgage Lender with 150 STRs financed over the last two years, specializing in creative financing for short-term rental acquisitions. Alex will break down which loan products actually work for second homes and luxury STRs in 2026, how W-2 income translates into approval power, and the financing structures that maximize leverage without overextending.

Steven Chau, Owner at Citadel CPAs, focused on real estate investors and high-income professionals. Using Michael's A-frame as a live example, Steven will show how the short-term rental tax loophole, cost segregation, and accelerated depreciation can offset W-2 income. These are strategies most CPAs don't proactively raise with their clients.

What You'll Walk Away With

• An acquisition framework for identifying top-tier short-term rental opportunities across Colorado
• A real case study with real numbers: acquisition price, debt structure, gross revenue, expenses, tax treatment
• How the STR tax loophole works for W-2 earners (and the material participation rules that make it legitimate)
• Which financing structures unlock STR ownership without requiring you to leave your job
• A framework for evaluating whether STR investing fits your specific tax and income situation

Who This Is For

• High-income professionals (tech, medical, legal, finance) looking for legitimate tax strategy
• W-2 earners curious about real estate as a wealth-building lever, without becoming a full-time landlord
• Anyone who's heard about the "STR tax loophole" and wants to understand if it actually applies to them

The Details:

Complimentary craft cocktails and hors d'oeuvres at Del Frisco's Double Eagle Steakhouse in Denver. Capacity is capped at 30 to keep the conversation small and the Q&A real. RSVP early; this one will fill.

Event Venue & Nearby Stays

Del Frisco's Grille, 100 Saint Paul Street, Denver, United States

Concerts, fests, parties, meetups - all the happenings, one place.

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