The Cincinnati Mistake That Built a $2 Billion Company with Joe Fairless

Real Estate Underground

Real Estate Underground
The Cincinnati Mistake That Built a $2 Billion Company with Joe Fairless
Mar 10, 2026 Season 5 Episode 185
Ed Mathews

Joe Fairless built Ashcroft Capital into one of the most recognized multifamily syndicators in the country — $2B+ in assets, properties across the Sunbelt, and a vertically integrated management company. But he started with $30K, student loans, and an apartment in New York where one paycheck covered rent and the other covered everything else.

In this episode, Joe gets candid about the deals that didn't work, the market conditions that are keeping multifamily investors in a holding pattern, and the one acquisition strategy most operators are completely ignoring right now: going direct to the lender.

Here's what we cover:

  • Why Fort Worth and Orlando are Ashcroft's two highest-conviction markets heading into late 2026
  • How Joe acquired a property for less than the outstanding debt — and what it took to get there
  • The lender relationship play that gives you first look at off-market distressed deals (even if you don't have your own management company)
  • Where the supply/demand shift is — and why Q3 2026 is the number operators keep landing on
  • Joe's personal 3.5% math: out of 140 LP deals across 50+ operators, what's actually gone to zero
  • The fixed vs. floating rate lesson that still stings
  • How Joe defines success — and it has nothing to do with deal count

Joe also shares his three bucket list goals for the year. One involves a fifth grader with a 2040 chess rating. That's all we're saying.

This week's book: The Road Less Traveled by M. Scott Peck

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Additional Resources:

Social Media:

  • LinkedIn -> Ed Mathews (President at Clark St and Elevista)

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