Keith Rabois on Opendoor ($OPEN) Activist Turnaround
15 Sept 2025 · 24 min
In this Sorcery podcast episode, investor and entrepreneur Keith Rabois discusses his activist involvement in turning around Opendoor, the iBuying platform. He explains that while Opendoor once achieved a $20 billion market cap and generated $500 million‑$1 billion of free cash flow, the company failed to build a resilient cost structure, leaving it vulnerable to real‑estate cycles and rising interest rates. Rabois recounts how he and co‑founder Eric Wu partnered to recruit a new CEO—Kaz, the former COO of Shopify—emphasizing Kaz’s founder mentality, product‑innovation chops, and proven ability to slash G&A from 14% to 4% of revenue. The turnaround playbook involves parallel actions: hiring top talent, dramatically reducing bloated G&A (targeting 200‑300 employees versus the current 1,400), deploying AI to automate home pricing, underwriting, and instant mortgage approval, and innovating financing products such as mortgage assumption and lease‑to‑own through a side‑venture called Roam. Rabois also outlines Opendoor’s unique value proposition—instant home sales in minutes and the vision of a “buy‑now” button that can close a purchase in 30 seconds. He contrasts Opendoor’s scale and market‑share in 50+ U.S. markets with competitors like Zillow and Rocket Mortgage, and touches on geographic considerations for future offices (Toronto, Miami). Throughout, he frames the effort as a high‑speed, founder‑led, data‑driven transformation aimed at making homeownership more affordable and resilient across market cycles.
Chapters
The most painful thing one can do other than having healthcare mess in your life is sell a home. On average, in the United States, homes sit on the market for like 80 days. And even after you get an offer, 20% of those offers never close. Imagine doing venture capital where you're not getting a term sheet for 80 days and then 20% of your term sheets would walk away from you.
When Opendoor originally went out, you could sell your house and it gets taken off your hands in 3 minutes and you get the money in 3 days. How is that possible?
Because we price the home automagically.
Let's talk about Opendoor. You mentioned back in 2015, things started go south?
No, no, no. The company did really well. I think we hit $20 billion as a market cap company for at least a day or two. We were making $500 million to $1 billion of free cash flow. But the company did not build the foundation correctly. Vinod Khosla, my partner, warned us about this. He said, you need to keep your fixed costs as low as possible because all real estate goes through cycles. Airbnb went through a similar problem when COVID hit, which was a true black swan.
Let's talk about Kaz. How did you decide this is who we need as CEO?
Kaz tweeted the other day that software, the only speed is faster. So we need to move very fast. Lightning speed. We wanted someone with a founder mentality who moves at lightning speed 24/7. Pure it.
Keith Rabois, welcome to Sorcery.
Pleasure to be with you.
This is one of the most quiet weeks of your life.
Oh yeah, this is pretty typical actually. The only difference is my phone has run out of batteries 3 times and that never happens. Because people have been calling me all the time and I'm not used to that.
You know Apple just came out with a new iPhone?
Yeah, yeah. Unfortunately, I ordered the thin Air. I don't want to carry the heavy one.
Really?
Yeah.
So no, you're not keeping a battery pack on stock. You don't have multiple phones.
No, hopefully people stop calling. I like messages, like iMessage.
So what's going on this week? Let's talk about it. Opendoor.
Yeah, so the company has a new leadership team, most importantly a new CEO. 99% of everything that matters is the CEO. The most important lesson for me over the last 25 years is if you have the right CEO, things that people believe to be impossible are very possible and sometimes probable. If you have the wrong CEO, almost nothing else matters. You know, Vinod Khosla was on my board at Square. My partner now at KV taught me this lesson in a pithy way, which is the team you build is the company you build. It's really easy to get distracted with everything else, like the product, the market, technology, but ultimately it comes down to the people. And so if you can marshal a critical density of talent, you have a shot of winning. That's what we did at PayPal. The reason why we were successful at PayPal was we had an unusual density of talent. We were able to sustain the density of talent, and we were able to accomplish things that most other people would not have been able to. The same thing hopefully will be true. We hired the single best person in the world that I really wanted from day one. There was no other choice in my mind. We can talk about why, but Kaz is the perfect CEO for Opendoor. We have a shot of fulfilling our destiny and our mission to completely transform residential real estate in the United States to start. It's a $289 trillion asset class. It's the largest in the world. Nobody's really innovated in over 30 years of technology. There's really nothing different about buying and selling a home today, except you can do— perform a search. You can perform a search and start your process, but every other part of that transaction is exactly the same as when I bought my first condo in the late '90s.
Let's talk about Kaz. So how did you decide this is who we need as CEO?
Well, we needed someone with product innovation ability. So he was not only serving as the COO of Shopify, but he also ran the product team. So we needed someone who understands how to innovate a product. Opendoor hasn't innovated a product 5, maybe longer, years. So someone who has that muscle on steroids. But most importantly, he's both bold and ambitious, but very disciplined and rigorous and analytical. And that's a rare combination. Ambition. A company like Opendoor needs to be rigorous and analytical, but it can't sacrifice the ambition and the boldness and the willingness to do things and push the envelope in creativity and innovate. And so that was what was very appealing. And then the company on a kind of tactical level just has too much of a bloated G&A. It's always had too much of a G&A that was way out of control since 2015. We need to fix that. There's 1,400 employees. There should be like more like 200 or 300 max. And one of the things he did at Shopify when he got promoted to be COO was cut their G&A as a fraction of revenue from 14% to 4%. And I think they're on target next year to be at 1%. So it's even more important for a non-software-based business to have a G&A that's in line with the cost structure, that's in line with the cycles that real estate always goes through. Every decade, residential commercial real estate goes through cycles and you need a fixed cost structure that can be appropriate for both the high season and the low season.
I kind of want to understand how this all went down. When did you get the call that you're going to be stepping in, joining Keith Rabois?
Well, it was sort of the other way around. I decided that the company needed to be fixed and partnered with Eric Wu, my co-founder and former CEO of the company, and said, "We're going to fix this and then we'll tell everybody else about it later.
Was this like while the meme stock hype was going on? Do you—
well, once the meme stock— um, so we started this project together on July 16th.
Oh wow.
Uh, and so the company's market cap had increased a fair amount with the attention brought by like Eric Jackson and his friends. Probably was trading at instead of 50-some-odd cents a share, probably $1.30 or so. And we said, "Hey, this is— well, it's too bad. It would have been easy to buy out the company ourselves and just own the whole thing if we had paid attention a month earlier," which probably would have been a better thing to do, truthfully. But we were a little lazy. And so it was like, "Okay, $1.30 is more expensive, but the potential of the company is still there." And now that we have catalyzed this movement, it's like a true cult of all normal people who care about the company, who perceive the opportunity, the potential of the company, we can use that to help recruit more talented folks. So we worked with our favorite executive recruiter, Paul Diversa. He posted on LinkedIn, explained the process. We said, Paul, we need to steal our CEO. Here's the criteria. Here's 5 things we absolutely have to have. The company, you know, is running its own search in the background with the wrong executive firm. They're going to come up with all these boring, bland, retread candidates from large companies that are going to be totally dysfunctional. Uh, we're going to find We're gonna find a great candidate and we're gonna tell the company they don't have a choice. We're hiring the right person. And that's what we did.
Sorcery is brought to you by Brex, the financial stack trusted by more than 30,000 companies, including 1 in 3 venture-backed startups in the US. Nearly 40% of startups fail because they run out of cash. Brex is literally built to help founders avoid that. Unlike traditional banks that let your money sit idle, chipping away at it with fees, Brex is designed to help you spend smarter and move faster. Their all-in-one Brix solution combines checking, treasury, and FDIC protection into one powerful account. You can send and receive money globally at lightning speeds, get 20 times the standard FDIC coverage through their partner banks, and even high yield from day one. With same-day and even same-hour liquidity, access your funds anytime. Companies like Scale AI, DoorDash, ServiceTitan, Hims, Anthropic, Flexport, Robinhood, and Plaid trust and use Brix. Start today at brex.com/sorcery. That's brex.com/sorcery.
I listened to an interview. Well, I think it was, it was a profile that Anthony Pompliano did. And then I think you took a picture with him. I don't know. But in this, he was talking about how this is going to be one of the biggest activist revisions of a comeback story for a company. And within that, I'm curious, like, what is the structure? Like, what is the playbook that you lay out here? Is it first talent? Is it Is it then restructuring? Is it then hoping things get fixed?
Well, I think we want to do it all in parallel speed. Kaz tweeted the other day that software, the only speed is faster. And so we need to move very fast, lightning speed. We wanted someone with a founder mentality who moves at lightning speed 24/7, period, and doesn't accept excuses. And so we needed to both innovate and execute all at the same time and recruit in parallel. The playbook I outlined my version of a playbook sometime in July or August. There's like 5 or 6 things the company needs to do, at least according to my strategy. We'll see how Kaz stitches that into an execution plan. I'm sure he has some creative thoughts that are even better to add on top. He's not short of ideas. He's been texting me constantly with like, revs on really good ideas. So he has to put together a plan. He starts Monday morning. I expect we'll have a plan very quickly and then we'll communicate the plan publicly, you know, sometime thereafter.
Can we come? Can we come while you're making this plan?
Sure. It sounds like a great idea.
We'll bring the crew and we'll just document it.
Every company that's ever done that hasn't done so well. There's this old documentary, which is a great movie called Startup.com. I do not recommend this to founders.
Don't document the process.
No.
Okay, so in terms of all this. All right. So let's talk about Opendoor in general macro. How did we get here with Opendoor? You mentioned back in 2015, things started to go south.
No, no, no. The company did really well. You know, we were almost— we were just— I think we hit $20 billion as market cap company for at least a day or two, minted money. We were actually free cash flow. We were between— we're minting $500 million to $1 billion of free cash flow when we were public. Went public in 2020, late 2020, and the company is doing really well, but the company did not build the foundation correctly so that when interest rates rose and the Fed raised interest rates 6 times in a very compressed period of time, unprecedented compression of time. When interest rates rose, the company's cost structure was inappropriate for the amount of transactions that were going to occur in the United States. In a peak United States housing market, 6 million Americans buy a home, And in a bad market, 4 million do. So it's a pretty big variability there. So you need to be able to be profitable or break even in a market when only 4 million Americans transact. Opendoor is currently a transactional business, so we get paid when we buy and sell. And so if less people, like 50% less, are buying and selling, all of a sudden your costs are out of whack. But the reason why I mentioned 2015 is Vinod Khosla, my partner, warned us about this. I remember a meeting, a review we did, Eric and I did,, with Vinod, and he said, you need to keep your fixed costs as low as possible because all real estate goes through cycles, and you want as much variable cost in the business and as low fixed cost as possible. For a variety of reasons, that never really happened. And then in 2021, when we went through the interest rate hikes, or 2022, the company's fixed costs were just way too high, and they're still way too high. But this is something that you can't really have— there's no excuses for. Everybody knows residential is somewhat cyclical. Airbnb went through a similar problem when COVID hit, which was a true black swan. Airbnb has a great business model, 13%, you know, blah, blah, blah, lots of profits on the margin. But when COVID hit and everybody got locked down, guess what? People didn't travel and all of their contribution profit disappeared overnight. And then they realized, oh my God, we were burning money everywhere and we're going to run out. Airbnb almost failed in the first month of COVID and they got— they fortunately put together a fairly clever sort of note with Silver Lake that saved the company. But Airbnb, I wouldn't blame too much. COVID was a once every 50, 100-year sort of black swan. Opendoor needs to think about residential real estate cycles and build the business to be resilient in any cycle and any macro environment. It has to work.
In today's high-speed business world, staying ahead means using the smartest tools possible, including the powerful capabilities of artificial intelligence. Meet Turing Intelligence. Turing builds customizable AI systems designed to solve your mission-critical challenges, no matter your industry. From expert guidance to tailored projects, Turing helps top companies realize AI that's more capable, more adaptable, and more effective. With Turing, discover how AI can accelerate your business growth. To learn more, visit Turing.com/Sorcery, spelt S-O-U-R-C-E-R-Y. That's Turing.com/Sorcery.
How do you start making this go faster? Do you start cutting people? Do you start implementing AI?
Well, we're definitely gonna implement AI. I think that's the biggest unlock. So some of the things that are now, some of the things we wanted to do in the 2015 era in terms of avoiding fixed cost, may not have been completely possible but now are easy. So it shifted from very difficult to easy to use technology to substitute for humans. We see it more and more of this every day. Normal people do this every day. Instead of calling a doctor, they use ChatGPT. Instead of calling a lawyer, they use ChatGPT. This is very common. Instead of using a real estate agent, there's no reason they can't use ChatGPT or an equivalent product. So I think a lot of things have got easier and the magic wand will be easier to deploy. The second thing though that the company needs to do is make homes more affordable. There are many, many Americans that want to buy homes that can't because mortgage prices are just too high. The monthly payment is too high with this interest rate environment. And we need to innovate so that more Americans can afford a home. Calhoun's put out this wonderful statement about the mission and vision of the company that when people buy homes, everybody wins. The communities are safer, better, kids are better, healthier, happier. Owners build value and renters generally subtract and extract. And so we needed a homeownership society and we want to be the company that propels more homeownership. And that includes innovating on the financing side. Most people don't even know that 30% of homes in the United States are— it's legally permissible to assume the mortgage of the person who owns the home. So if someone has a fixed-rate mortgage at 1%, 2%, 3%, You can buy the home and take on their mortgage. We started a company, Eric Wu and I actually started a company called Roam that enables this and makes it sort of friction-free. But by law, 30% of the homes in the United States are instantly available to assume the mortgage. So there's a lot of clever things one can do to solve the affordability crisis in the United States.
When Opendoor originally went out, it was you could buy a house and like, and You could buy a house and— or you could sell your house and it gets taken off your hands in 3 minutes.
3 minutes. And you get the money in 3 days.
How is that possible?
Well, because we price the home automagically. And what we really want to do, the next level, is we want to allow the buyer side to buy the home in 30 seconds. That has been on my wish list for a decade because 70% of Americans buy homes with mortgages. Until you could provide an instant guaranteed mortgage, it wasn't a mainstream product, but many companies now provide instant underwriting for mortgages. So having— imagine every home you see online having a buy it now button. You're like, I like this house, I want it, and just buying it. Yeah, no agent, nothing. You don't have to go see it if you don't want to, um, which is also a trend. There's a macro trend towards buying homes sight unseen that also COVID, uh, sort of, uh, accelerated.
I just had Klarna CEO Sebastian Szymiankowski on the pod, and it was funny, uh, towards the end I was like, you know, We should really think about expanding products here. What if we get into homes? You could buy now, you could pay later homes. And it was a joke, right? He was like, Molly, that's called a mortgage.
Well, one of the reasons why people don't innovate is there's a subsidized government product called a mortgage for what are called conforming homes. And because the government takes on the risk, there's not a lot of incentive for private entities to sort of underwrite better. And that's what led to the mortgage crisis in some ways. People parked the risk on the federal government. Stop that to some extent, but there's still ways to innovate. Like, for example, think about lease-to-own. Wouldn't you like to lease, lease a house, test it out, see if the neighborhood's pleasant, the schools are cool, the noise— is there noise at night? And then you have the right to buy it over time. That should be a mainstream product too.
Is that on your product roadmap?
It's a good idea, actually. I think it should be. But the question is prioritization.
So what's the difference between Opendoor, Zillow, and Rocket Mortgage? How do you—
there's no other place in the United States at any scale where you can buy a home, where you can sell your home instantly. There's other people that profess or try or pilot, but we do this in 50+ markets in the United States. In many markets, we have double-digit market share. In many, many markets, we have 5% or more market share. So if you want to sell your home, you don't want to deal with the uncertainty and risk like the traditional way. Let's backtrack. The most painful thing one can do other than having a healthcare mess in your life or family's life is sell a home. Selling a home is so painful because you list it and you have no idea what's going to happen and how long it's going to take. On average, in the United States, homes sit on the market for like 80 days. And even after you get an offer, 20% of those offers never close. Imagine doing venture capital where you not get a term sheet for 80 days and then 20% of your term sheets would walk away from you. That is actually what happens in homes. So with Opendoor, there's certainty. In speed immediately. The, the real primary reason people need this, like the number one use case, is I want to buy a new home. My family has got larger, or I'm moving cities or states. And typically, if I'm using a mortgage, the bank will not allow me to make a non-contingent offer, or to make an offer that's valid until I clear the mortgage off my prior house. So you have this delegate, like dance of like, oh, I love this house over here, but I can't really buy it till I sell this one. But you don't have any idea how long this one's going to take to sell. And so you may lose the opportunity to buy the new house that is the sort of house, the proverbial house of your dreams, or someone else buys it from you, or you just procrastinate because you know you're gonna have to deal with this mess. So we solve the mess. It's like you can basically trade in your house like you trade in a car. Like something like 50% of cars in the United States are— some of the new car purchases involve a trade-in. So why can't you trade in your house? I'm done with this house. I want this one. We'll take it off your hands.
Boom.
Get your dream house. Move in tomorrow.
America. Free markets.
Exactly.
So are you going to use Opendoor?
Well, we don't currently. So the mission and the goal of the company was always to serve the middle of the bell curve of homes in the United States, technically 83%. So when we go into any market, Bay Area, New York, Atlanta, Dallas, wherever, we price 83% of homes. For better or for worse, my homes are not within the 83%, uh, standard deviation.
Are you saying you're out of the bell curve?
I, I am, uh, well, intentionally. Like, um, you know, like, I, I remember when I was having Lasik and, um, I was so nervous about having Lasik. It's 2003, uh, and the doctor could kind of tell, and he figured out a little bit about me professional, and he did all these tests. It was like an hour-long sort of program. And he comes back to me and he says, like, I'm going to tell you something that you've probably never been happy to hear before. He's like, you're right down the middle of the bell curve. This procedure is designed for you. There's no way anything goes wrong unless I personally screw up. I was like, great, we're finally doing this procedure.
So you're in Miami?
I'm actually more in New York now.
Okay, you're more in New York now.
Yes, right down the street.
Is the company going to be here? Where is the company based?
Well, I'll leave that to the CEO, but the company will be in person. Company will probably have one or two key offices. I suspect that Toronto will be one of them, and I wouldn't be surprised if Miami is a great choice. Miami is one of the best cities in America. It's happiest, healthiest, wealthiest. It's very real estate friendly. As many people know, it's a normal market, meaning like it the bell curve actually kind of works like New York's very atypical in many dimensions, for example. So we'll, we'll evolve, we'll see. But I would suspect that there'll be 2 offices max to start.
What brought you up here?
So I have some family needs. Well, I have some company needs. 8 of my 12 last— about 8 of the last 12 investments are actually in New York. And then secondarily, I need to go to D.C. fairly frequently now. I'm actually going there later today and it's much easier to get back and forth from D.C. to D.C. or from D.C. from New York than Miami. Helicopter, train, plane. Miami, you can only take a plane and it gets subject to weather delays.
You take a helicopter to—
Sure.
To D.C. Yeah. From New York.
Yeah, it's like an hour.
That's crazy.
Why?
That's so— that I've never heard of that.
It's pretty cool.
Helicopters freak me out. So maybe it's not.
Well, if you got the right configuration of helicopter with multiple pilots and stuff, it's, it's, it is more dangerous than many other things. But with the right equipment and the right pilots and the right discipline, it's not that bad.
So do you blade out of the West Side?
Yeah.
Or like down in FIDAE?
Yeah, the West Side.
That's pretty cool. Okay. All right. So maybe let's shift over to D.C. What is the state of the market in D.C.? I'm a big fan of Jacob, all the work he's doing.
Well, D.C., you know, is not a great market for early-stage entrepreneurs, which is my primary job, hence the New York and, you know, some trips to the Bay Area and Miami and other places. It is a wonderful market for people who are building, who are probably post the scaling of a company. The new environment in D.C. is business-friendly. Innovation-friendly and pro-American. And so if you're building a company that can contribute to innovation, GDP growth, productivity gains, or America's national security, there's a lot of, you know, receptivity towards those kind of entrepreneurs. And so you see a lot of successful entrepreneurs spending more time in Washington.
It seems like there has been a huge shift, but it seems like it's kind of getting quiet.
No, no. When I, when I'm in D.C., inevitably I run into very successful entrepreneurs. Like, I'm not— I don't even tell them I'm going to be there. And I just walk down the street and I run into people that are, you know, running $10 to $10 billion and $2 trillion companies without even trying. That was— that would never happen in my life before.
So you see like Jensen walking on the street?
Yeah. Or friends, Patrick Carlson, whoever. People are in DC all the time.
Hey, it's Molly. If you enjoy our interviews, check out our newsletter sorcery.vc where we deliver a once-a-week top deals and tech headlines email and also go deeper on our podcast interviews. Subscribe to Sorcery today and don't forget to subscribe to the podcast on YouTube, Spotify, Apple, or wherever you listen. Link in description to sign up.
More from Keith


#274 Keith Rabois: One of Silicon Valley’s Most Influential Investors and Operators in His Most Personal Conversation Yet
Trump's Cabinet, Google's Quantum Chip, Apple's Flop, TikTok, State of VC with bestie Keith Rabois