Skip to Content
| June 26, 2025

Building a $1.5B real estate empire

Zillow co-founder Spencer Rascoff and Dotloop founder Austin Allison both knew that owning a vacation home was a great privilege — and an expensive hassle. They’re leveraging their decades of experience in real estate to reshape how owning a vacation home works with a new business: Pacaso. They join host Jeff Berman to reveal how it became the fastest U.S. company to ever reach unicorn status.

Building a $1.5B real estate empire — with Pacaso’s Spencer Rascoff, Pacaso’s Austin Allison and WaitWhat’s Jeff Berman
Download
0:00 / 0:00

About Spencer

  • CEO of Match Group, overseeing Tinder, Hinge, and 20+ dating/social brands (2025)
  • Co-founded Zillow; led growth to $3B revenue, $10B valuation, 4,500+ employees (as of 2019)
  • Co-founder of Pacaso, the fastest U.S. startup to achieve unicorn status (2020)
  • Co-founded Hotwire; acquired by Expedia for $685M in 2003
  • Harvard professor of entrepreneurship; teaches startup and leadership courses

About Austin

  • Co-founded Pacaso, valued at $1.5B within 18 months (2025 Series C)
  • Founded Dotloop, acquired by Zillow in 2015
  • 10 years experience in residential & commercial real estate, started at age 18
  • Served as Zillow executive after Dotloop acquisition until 2018
  • Pioneered tech-enabled real estate transactions and co-ownership models

Transcript: