Doug Brien

Observer
DISC Type : ci

President & CEO at Roofstock

Oakland, California, United States

Overview

Doug Brien is the President & CEO of Roofstock, a company focused on making single-family real estate investing accessible. He is a serial entrepreneur, having co-founded Mynd and Waypoint Homes, building the latter into a $3 billion portfolio. Doug earned his MBA from Tulane University while playing professionally in the NFL.

Before his business career, Doug was a professional placekicker in the NFL for twelve seasons. He won a Super Bowl with the San Francisco 49ers and was inducted into the Cal Hall of Fame in 2023 for his achievements as the universitys 2nd all-time leading scorer.

A unique fact about Doug is that he used his first Super Bowl check to purchase and flip his first investment property, kickstarting his career in real estate.

Personality Overview

Value Driven

Curious

Assertive

They are generally good communicators and can be hard to convince.  They can sound friendly and charming but can quickly change gears to become inquisitive and probing. They often ask many questions and rely heavily on information and documentation.

Topics They Care About

Real Estate Investing
He co-founded multiple companies to make single-family rental investing simple and accessible, and authored a book on the topic called "The Big Long. "
PropTech
His companies, Roofstock and Mynd, are built on leveraging technology, data, and AI to create a premier platform for the single-family rental industry.
Entrepreneurial Mindset
A serial entrepreneur who took a company public, he often speaks about having a growth mindset and finding ways to scale revolutionary business ideas.

Media Appearances

Doug has no verified media appearances

Work History

10-2025
President & CEO at Roofstock
5-2024 - 10-2025
President at Roofstock
5-2016
CEO and Co-Founder at Mynd
5-2016 - 5-2017
Co-CEO and Co-Founder at Mynd
9-2017
Executive In Residence at University of California, Berkeley, Haas School of Business

Education

1989 - 1994
Political Economies from University of California, Berkeley
1998 - 2002
MBA from Tulane University - A.B. Freeman School of Business

More Information

Social Presence :

Prographics :

Exp : 16 Location : Oakland, California, United States Job Level : Leadership Designation : President & CEO at Roofstock
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Insights For Selling To Doug

During A Call Or A Meeting

DO's

  • Use phrases like ‘clear proof that’, ‘data shows’ etc.
  • Be prepared for a lot of questions, answer them objectively
  • Help them understand the risk aspect fully while inspiring confidence

DONT's

  • Don’t rely excessively on your relationship with them to win the deal
  • Avoid making offhand commitments
  • Don’t try to rush them into a decision, provide all necessary information first

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Doug is

  • Clear proof of product value matters to them, followed by others' testimonials and rapport.
  • Will you ever get a clear answer from Doug

  • They are practical and friendly, don't expect a clear-cut response often.

Insights For Deal Planning

    How fast (or slow) will Doug move?

  • They like to perform full analysis and can take time to make any decision.
  • Can Doug take some risk or not?

  • They systematically evaluate all decisions and are unlikely to take many risks.

You And Doug

Personality Compatibility


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