This Entrepreneur Sold A Company To Comcast For ~$400 Million And Is Now Building A Platform To Revolutionize The Mortgage Industry

In this engaging interview, Diane Yu, a repeated founder and highly successful entrepreneur, offers valuable insights into her extraordinary journey from a young graduate to a leading force in the technology and finance sectors.

From her early days at DoubleClick to her role in building FreeWheel, which Comcast acquired for about $400M, and now her current venture, TidalWave, Diane has consistently focused on innovation, learning, and building strong relationships.

Diane talks about planning each day based on what you can learn, thinking about talent and how to retain it, and creating loyalty so the talent stays with you through further journeys.

Listen to the full podcast episode and review the transcript here.

From China to DoubleClick: The Beginning of a Journey

Diane’s story begins in China, where she grew up in a major city. Her father encouraged her to explore the world outside her home country, and she promised to do so.

That promise led her to the United States for graduate studies, which eventually set the stage for her impressive career in tech. Diane’s first significant role came at DoubleClick, one of the earliest companies in the startup venture ecosystem that was starting to develop in New York City.

Unlike present times when venture capital is more commonplace, back then, it was almost non-existent. What made Diane’s journey to DoubleClick special was the serendipity of the moment.

While visiting New York City to meet a friend, she received a call from a recruiter asking if she could come by their office. That simple meeting led her to a life-changing opportunity.

Diane recalls how the VP of Engineering, John Heider, not only offered her the job but also sent her a heartfelt card and gift basket, inviting her to join the company and sealing her commitment to it.

This gesture of authenticity and genuine connection had a profound impact on her, shaping her approach to recruiting talent in her future ventures. Diane learned that if you treat people fairly and with genuine care, they will follow you.

Loyalty, Learning, and Leadership at DoubleClick

Diane’s experience at DoubleClick ingrained a sense of loyalty in her, motivating her to remain with the company even after its acquisition. She spent nearly a decade at DoubleClick, starting as an engineer and steadily working her way up to become the VP of Engineering.

What kept Diane at DoubleClick for so long? She remembers it was the constant opportunity to learn. Every year brought a new job, challenges, teams, and lessons. Over her nine-year tenure, she worked with 11 different teams, always driven by her desire to learn something new each day.

This hunger for knowledge and growth was central to Diane’s leadership style and helped motivate her and her teams. Her time at DoubleClick culminated in Google’s acquisition, which led her to a pivotal career decision: stay at a large company or take the leap into entrepreneurship.

True to her adventurous spirit, Diane chose the latter, leaving the security of her role to co-found FreeWheel. Her objective was simply to learn more. She chose to dive into something she had never done before and push herself out of her comfort zone.

Diane recalls her good friend and co-founder, Dwight Merriman, trying to dissuade her. Later, he agreed with her perspective and has also invested in her second company.

Building FreeWheel: A Phenomenal Success

As a co-founder and CTO of FreeWheel, Diane and her partners built a B2B video monetization platform that connected buyers and sellers in the media industry. FreeWheel became a global leader, enabling media companies to monetize their video content through advertising.

The platform was like an exchange enabling advertisements to be delivered to an audience based on where they want to see and watch videos. Diane recalls that when they started out, they never expected to get the volume of customers, particularly large global media companies.

A crucial moment for the company was landing YouTube as a partner early on, which signaled they were onto something big. Diane recalls when they realized they were building a truly successful business: they reached $1M in annual revenue.

This milestone confirmed that they were doing something right, that their solution was solving a big problem for their customers, and that they had a viable business model. Knowing they were creating value in the media space was a rewarding moment for Diane and her team.

The ~$400M Acquisition by Comcast

FreeWheel’s success caught the attention of Comcast, and after several discussions that began with a potential customer relationship, Comcast made an offer to acquire the company.

Diane and her co-founders saw this as an opportunity to take their platform to the next level, expanding its reach and accelerating growth. The acquisition was finalized for close to $400M, a monumental achievement for Diane and her team.

As Diane recalls, when building the company, the objective was to create a solution for a problem without considering an exit strategy. Comcast presented as the right platform for TV monetization. Comcast not only acquired FreeWheel but also acted as a vesting and resting partner.

But Diane didn’t just cash out and leave. She stayed with Comcast for over seven years, far longer than most founders typically stay after an acquisition.

Diane’s motivation to stay on was driven by the unique opportunity to restructure and integrate five companies Comcast had acquired into a unified platform. For her, it was an unparalleled learning experience—a chance to build something more significant and impactful.

As Diane reveals, the five companies came from different experiences, platforms, and cultures, and she was assigned the task of structuring them into a single platform, rebuilding and building the team under the same culture, becoming one culture, one platform.

Diane saw it as a challenge she wouldn’t have the opportunity to take on elsewhere. She stayed committed to building the platform and team together.

TidalWave: Revolutionizing the Mortgage Industry

After her long tenure at Comcast, Diane made another bold move, joining Better as CTO to gain insight into the mortgage industry. She found an industry plagued by inefficiencies, especially in the mortgage origination process.

Diane realized the magnitude of the problem with the applications in the mortgage industry. Purchasing a home is the most significant investment in an American individual’s lifetime. To do that, they must purchase a mortgage.

Applying for a mortgage involves sending the loan officer detailed information, including their financial history. After that, applicants can do nothing except wait for approval, which can take anywhere from 30 to 45 days. In the end, they can get approved or rejected.

Borrowers often face a long, opaque process with little transparency, which can be a bad customer experience. On their part, lenders struggle with outdated systems that require extensive manual labor and are not cost-efficient.

Seeing a massive problem ripe for disruption, Diane co-founded TidalWave, a SaaS platform designed to streamline and simplify mortgage origination. TidalWave aims to solve a significant problem for borrowers and lenders, making the mortgage process more transparent and efficient.

By leveraging technology, Diane believes TidalWave can help lenders originate more loans while reducing their dependence on manual labor, which will stabilize their businesses through market fluctuations and mortgage rates going up and down.

During mortgage rate downtrends, lenders must deal with high origination volumes and the need for rapid expansion. But, during rate increases, loan officers deal with layoffs because of the over-hiring. Lenders needed solutions to emerge from the boom and bust cycles.

That’s when Diane decided to leverage her expertise in technology and business to create solutions and change the mortgage industry. She founded TidalWave and also took on the position of CEO when she was formerly the CTO. Essentially, this was her foray into financial technology.

Building a Loyal Team and Investor Network

Diane’s journey has been marked by her ability to build long-lasting relationships with her team and investors. Many engineers who worked with her at FreeWheel and Better have followed her to TidalWave, sharing her passion for solving big problems.

Diane emphasizes the importance of trust and loyalty when building a team, especially in the challenging world of startups. She talks about connecting with many people with experience and passion for the mortgage industry.

Diane’s team at TidalWave comprises a combination of engineers who have worked with her for over 20 years, along with people with 20 years of mortgage origination and operational experience working collectively.

The same philosophy applies to Diane’s approach to investors. She has been fortunate to work with investors who supported her from the beginning, including those who backed FreeWheel.

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Diane particularly mentions an investor who backed her back in 2008 after the last financial bust. He saw the potential in FreeWheel and the capability of the founder and the team they built together.

These relationships are built on mutual respect and a shared vision for the future, allowing Diane to select investors who align with her goals and values.

The Road Ahead for TidalWave

Diane’s journey with TidalWave is just the beginning, but her vision is clear. She is passionate about creating a platform that will transform the mortgage industry, making it easier for borrowers to navigate the most significant financial decisions of their lives.

Diane envisions the platform being utilized by a large percentage of lenders who leverage its capability to provide real-time mortgage loan products and offerings to their customers. Borrowers should have a happy, fully transparent experience.

Diane is confident that TidalWave can make a lasting impact by building a cohesive solution that addresses the borrower experience and lender efficiency so they don’t lose money.

As a second-time founder and now CEO, Diane has crossed the bridge from tech to business leadership, a challenging but rewarding transition. She focuses on learning and growing personally and professionally as she leads TidalWave into the future.

Conclusion

Diane Yu’s story is about perseverance, learning, and a relentless drive to solve big problems. From her early days at DoubleClick to the successful exit of FreeWheel and now her new venture with TidalWave, Diane has consistently pushed herself out of her comfort zone to achieve greatness.

Her journey inspires entrepreneurs everywhere, showing that with the right mindset, strong relationships, and a passion for learning, anything is possible.

Listen to the full podcast episode to know more, including:

Diane Yu’s journey from China to the U.S. began with a promise to explore opportunities outside her homeland, leading her to a successful career in tech.
Building long-term relationships and loyalty with investors and team members has been a cornerstone of Diane’s success across multiple ventures.
Diane’s experience at DoubleClick taught her the value of constant learning, team-building, and staying motivated through personal and professional growth.
As a founder of FreeWheel, she helped build a major B2B video monetization platform, eventually leading to Comcast’s $400M acquisition.
Diane stayed with Comcast for seven years after the acquisition, driven by the opportunity to learn and restructure multiple platforms across acquired companies.
Diane founded TidalWave to solve inefficiencies in the mortgage origination process, combining technology with industry expertise to create a better customer and lender experience.
Carefully selecting team members and investors based on trust and long-term relationships has been critical to Diane’s leadership and entrepreneurial strategy.

 

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