This is where Zillow found its edge. Homeowners are inherently curious about their home’s value. Zillow launched Zestimate, a tool that estimated the market value of nearly every home. Though brokers often criticized its accuracy, homeowners stayed engaged, driven by curiosity and frequent updates.

Zillow monetized this attention by selling leads to brokers. When users inquire about a home on Zillow, their query often isn’t routed to the listing broker. Instead, it is sent to a broker who paid Zillow a premium. This leads to sales calls from brokers the user wasn’t expecting. While profitable for Zillow, it isn’t ideal for consumers. A savvy homebuyer might negotiate a rebate directly with a broker rather than allowing Zillow to collect the fee. Once a client is signed, the traditional homebuying process resumes.

Redfin, on the other hand, was an early adopter of Google Maps to display listings—an innovation that significantly boosted usability. Even today, Redfin arguably offers the most user-friendly search interface. From the beginning, Redfin focused on homebuyers, offering them rebates to earn their business. This was a superior approach for consumers: unlike Zillow, which captured the value of client acquisition for its platform, Redfin passed the savings directly to buyers.

Redfin introduced a thoughtful model—rebates for buyers upfront and guaranteed compensation for brokers on the back end, even if the sale didn’t close. This empowered brokers with strong service skills but limited client acquisition abilities to succeed.

In 2019, Redfin tested a digital homebuying process in Boston that allowed buyers to submit offers directly via its site—without a broker. The concept made headlines and had transformative potential, but adoption was low. Despite millions of visitors, few used the feature. The problem was clear: Redfin’s interface mimicked a “Buy” button but still required users to follow traditional offline steps. It allowed buyers to act as their own brokers instead of simplifying the experience. The system lacked the imagination needed for true ecommerce. Imagine an ecommerce platform that lets you buy online—but then requires all the steps of an in-store purchase. That was Redfin’s digital offering.

Innovation demands persistence and iteration. That’s where Redfin stumbled. Redfin’s CEO Glenn Kelman had an opportunity to transform the industry—much like Howard Schultz did at Starbucks. Redfin prioritized flawless execution: necessary, yes, but insufficient for meaningful industry change.

Let me share a personal anecdote. Haresh Sangani, Eduardo Oliveira, and I co-founded Faira, a real estate technology startup we ran until the onset of COVID. Faira was the only company to turn home transactions into a true ecommerce experience—reducing stress and cost for consumers. Despite limited resources, we facilitated hundreds of fully digital transactions. We didn’t ask buyers or sellers to act as their own brokers—we eliminated the need entirely. Sellers focused on net proceeds and timely closings; buyers focused on finding the right home at the right price. Everything else was stripped away. With Faira, buyers could make an offer in minutes—compared to hours on Redfin. Sellers could complete the entire process online.

When Redfin’s Boston experiment fizzled, I expected them to reach out and learn from Faira model. If I were leading Redfin, I would have done exactly that. Once that didn’t happen, Haresh offered Redfin’s CEO a demo of Faira platform. He accepted and helped arrange it at their corporate office—but sent a deputy who asked broker-centric questions and showed little interest in how consumers engaged with a true ecommerce platform.

We never understood why Redfin didn’t show serious curiosity about our transformative model—the only platform that successfully enabled an end-to-end ecommerce experience for real estate. If I had to guess, perhaps Redfin wasn’t fully committed to the Boston initiative and remained more focused on executing the legacy transaction model than transforming it.

Thankfully, Redfin remains in business with a strong brand. That said, it has lost money for investors. Shares purchased at IPO for $15 exited around $10, through Rocket Companies’ acquisition. Rocket now owns both a home transaction and financing platform—giving it the chance to finally revolutionize the real estate industry. I hope they revisit Redfin’s Boston experiment and make home transactions truly easy and affordable.

The focus should be on consumers. A successful platform must abstract out complexity and remove consumer risk from the transaction. It’s similar to an ecommerce site offering unconditional returns—eliminating the risk of a mismatched product. Recent changes in real estate association rules further enable Rocket to offer such a platform. It’s easier said than done, of course. There are numerous anxieties that homebuyers and sellers face—and those must be addressed. Haresh and I would be happy to share what we’ve learned.

This post also illustrates that imagination and courage are just the 35,000-foot view. On the ground, transformation requires excellent execution, experimentation, iteration, curiosity, and humility to learn.

So I leave you with this question: What would you do if you were leading Redfin?

Disclaimer: The opinions expressed are solely my own and do not reflect those of my current or past employers.

Earlier posts in the series: Department of Imagination and Courage,  Microsoft: A Story of Imagination and Courage, Expedia: A Success Story Despite Missed Opportunities, T-Mobile: How an Underdog Outweighed Elephants, and Starbucks: From 4 to 40,000 in 40 Years.