Industry Relations

An Open Letter to Opendoor

Aug 21, 2025
Rob and Greg dive into the fallout from Carrie Wheeler's resignation at Opendoor. They analyze the impact of activist investors and the future of iBuying amidst shifting buyer expectations. The duo examines how Opendoor and Zillow have operated more like flippers than true market makers. Strategic advice for new leadership includes selling homes ‘as is,’ enhancing agent relations, and creating a coming-soon marketplace for discounted listings. They also discuss innovative financing options to streamline transactions and ensure long-term viability.
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ANECDOTE

Hosts Tease Each Other Over Resignation

  • Rob jokes he had nothing to do with Carrie Wheeler's resignation while teasing Greg about causing it.
  • The hosts open the episode with playful banter about Opendoor leadership changes.
ANECDOTE

Hosts Held And Averaged Into Opendoor

  • Both hosts reveal they remained Opendoor shareholders and dollar-averaged during the crash.
  • Greg notes buying shares below $1 to reduce his average cost, illustrating retail investor behavior.
INSIGHT

Retail Meme Power Moves Leadership

  • Retail investor meme energy and activist pressure can rapidly reshape public-company leadership and strategy.
  • Eric Jackson rallied retail support that amplified pressure on Opendoor's board, contributing to Carrie Wheeler's resignation.
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