Startup Icons Share How Zillow and DocuSign Were Born

Two of Seattle’s most influential entrepreneurs recently pulled back the curtain on how they built billion-dollar companies, sharing valuable startup lessons drawn from personal experiences, early failures, and unconventional business strategies.

Speaking at a Founder Nexus event held on Microsoft’s campus, Rich Barton, the entrepreneur behind Expedia, Zillow, and co-founder of Glassdoor, joined Court Lorenzini, the founding CEO of DocuSign, to discuss the ideas that sparked their companies and the decisions that shaped their success.

Everyday Frustrations Sparked Big Ideas

For Barton, entrepreneurship began with a simple workplace annoyance.

After joining Microsoft in 1991, he became frustrated with the company’s internal travel booking system. Believing technology could make the process much easier, he envisioned giving consumers direct access to travel booking information through the internet.

That idea eventually became Expedia, which spun out of Microsoft and went public in 1999.

Barton later found himself facing another frustrating experience while searching for a home.

He said the available real estate information online was poor, despite housing being one of the largest consumer markets. That realization inspired him to launch Zillow in 2004, which later became one of the world’s best-known online real estate platforms and completed its IPO in 2011.

Lorenzini’s entrepreneurial journey followed a different path.

In 2003, he helped launch DocuSign after acquiring a digital signature patent and the company’s brand from the assets of a failed business.

Rather than inventing the original technology, Lorenzini recognized its commercial potential and built a successful company around it. Barton praised that ability, saying Lorenzini had discovered “the pearl in the ocean.”

Today, Zillow and DocuSign together have a market capitalization exceeding $30 billion, while Expedia is valued at more than $23 billion.

Different Business Models, Same Goal

Although both founders built highly successful technology companies, their approaches to growing a business were very different.

Barton has long believed in offering products to consumers for free before developing revenue opportunities. He explained that once a platform attracts a large audience, businesses naturally want access to those customers, even if the platform disrupts the existing industry.

Lorenzini took the opposite view.

He said he never wanted to rely on a freemium strategy because he believed businesses should pay for products from the beginning.

Instead of targeting consumers, DocuSign focused entirely on paying business customers during its early years. According to Lorenzini, that strategy helped the company build a sustainable business before eventually becoming a widely recognized consumer brand.

During the discussion, Barton jokingly responded, “It’s the only strategy I know, Court.”

Avoid Scaling Too Soon

The veteran founders also offered practical advice for entrepreneurs building early-stage startups.

Lorenzini stressed the importance of finding strong product-market fit before investing heavily in sales and marketing. He warned that many startups hire sales teams and launch expensive marketing campaigns before customers are genuinely demanding the product.

According to him, premature spending is one of the biggest reasons startups fail.

Barton agreed that founders should avoid spending large amounts on advertising in the early stages.

Instead, he encouraged entrepreneurs to build products with unique or surprising features that naturally generate word-of-mouth recommendations. In his view, the product itself remains the strongest marketing tool any startup can have.

Company Culture Matters

The conversation also explored leadership and workplace culture.

Lorenzini said he intentionally built DocuSign’s culture as a competitive advantage, believing it played a major role in attracting and keeping talented employees.

Barton admitted his approach was more instinctive but said one lesson from Microsoft’s demanding early culture stayed with him.

When Expedia became an independent company, he deliberately focused on creating an environment built on mutual respect. He compared a successful business to a wheel, explaining that every member of the team must contribute equally for the company to move forward.

Continuing to Shape Seattle’s Startup Community

Although both founders have moved beyond their original startups, they continue to play active roles in the technology ecosystem.

Lorenzini left DocuSign in 2008 and launched Founder Nexus last year, creating a community that supports startup founders. He also serves as a limited partner in Seattle venture firms including Graham & Walker, Ascend, and Unlock Venture Partners.

Barton returned to Zillow as CEO in 2019 before stepping away from day-to-day leadership last year. He continues to serve as the company’s executive chair and has also been a longtime board member at Netflix.

Their discussion highlighted that while successful entrepreneurs often take different paths, innovation frequently begins with identifying everyday problems and finding better ways to solve them.

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