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How Pacaso Built a $1.5B Real Estate Empire

Building
June 28, 2025
Zillow and Dotloop founders share how they created Pacaso—America's fastest unicorn in real estate.
Topics discussed in the episode:
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How to leverage past experiences in new startups?
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What is a Reg A offering in fundraising?
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How can founders benefit from joining larger companies?
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Why focus on core markets during downturns?
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How to proactively address regulatory challenges?
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How to manage through adversity by controlling what you can?
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Should founders over-communicate their ideas?
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Why build relationships with potential acquirers?
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How to manage team downsizing with empathy?
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How to stay mission-focused during a crisis?

How to leverage past experiences in new startups?

Applying prior lessons strengthens new ventures.

"I've now been doing this for a long time... and I've seen this a couple of times..."

  • Spencer utilizes past experiences to navigate challenges.
  • Learning from past startups aids decision-making.
  • Experience informs market insights.

What is a Reg A offering in fundraising?

Reg A offerings are innovative fundraising tools for startups.

"We're in the middle of a Reg A offering, which is a way to democratize access to individual investors..."

  • Spencer explains Reg A allows raising capital from the public.
  • It enables companies to file public financials without full IPO.
  • Reg A bridges between venture funding and going public.

How can founders benefit from joining larger companies?

Joining a larger company can amplify a startup's mission and offer growth.

"I believed that being part of Zillow would enable dotloop to achieve its fullest potential."

  • Austin saw acquisition as a way to fulfill the mission.
  • Working with experienced teams offers learning opportunities.
  • Staying post-acquisition can lead to future ventures.

Why focus on core markets during downturns?

Prioritizing core markets sustains startups during economic downturns.

"We had to... focus in on the markets where we had the most scale and the strongest product market fit."

  • Austin advises focusing resources on best-performing markets.
  • Scaling back conserves resources and maintains momentum.
  • Concentrating on strong PMF areas ensures stability.

How to proactively address regulatory challenges?

Being proactive about regulatory issues aids successful expansion.

"I would say that the main thing that we've learned... is that it's really important to be proactive and not reactive on this front."

  • Austin learned to engage officials before entering new markets.
  • Understanding local rules prevents obstacles.
  • Proactive communication builds goodwill.

How to manage through adversity by controlling what you can?

Focusing on controllable factors helps navigate tough times.

"Staying focused on the mission. Staying focused on your team, controlling the things that you can control..."

  • Spencer emphasizes concentrating on mission and team during crises.
  • Controlling controllables aids in overcoming challenges.
  • Experience helps in weathering storms.

Should founders over-communicate their ideas?

Openly sharing your startup idea can bring unexpected opportunities.

"I always err on the side of over communicating about your idea."

  • Spencer believes the potential upside outweighs risks.
  • Sharing can attract acquirers or partners.
  • Fear of idea theft is often overestimated.

Why build relationships with potential acquirers?

Building relationships with potential acquirers can lead to successful exits.

"I always advise startup founders to make a list... and be very intentional long before you want to sell, start building those relationships."

  • Spencer Rascoff recommends founders proactively connect with acquirers.
  • Long-term relationships increase acquisition opportunities.
  • Regular communication positions startups favorably.

How to manage team downsizing with empathy?

Managing team downsizing with empathy is crucial to maintain trust and morale.

"We had to downsize the team. And we did it with class, I think, and took care of everybody."

  • Austin highlights the importance of handling layoffs thoughtfully.
  • Taking care of departing employees preserves relationships and reputation.
  • Approaching downsizing with empathy can aid future rehiring efforts.

How to stay mission-focused during a crisis?

Staying mission-focused can help founders navigate crises and find product-market fit during challenging times.

"If you believe deeply in the problem that you're solving, it serves as a North Star to help you navigate through whatever challenges you're facing."

  • Austin Allison emphasizes that passion for the mission guides founders through adversity.
  • By focusing on solving the core problem, founders can adapt and find PMF.
  • Deep belief in the mission acts as a compass during uncertain times.