The Ledger, every show

“I think the book lean startup may have done more damage unintentionally to software than any other book.”

“Where the founders are no longer there, there's no large shareholder that cares a lot about the company. So over time, many of these companies essentially become hosts for professional leeches whose job it is to suck the company dry while making management loo…”

“There is a level of suicidal empathy that people have developed that is just deadly. It is killing our best companies because people are assuming that everyone is thin-skinned, and they're assuming that people are offended by facts.”

“First of all, I don't think remote works. Generally, it only works for Shopify, and that's because we built more software to make remote work than anyone reasonably thought we could. And I think the jury has fully come back on this topic, that companies that a…”

“What, for most tech companies, AB tests have done have been the safety blanket for management.”

“On my first day at Opendoor, I said, hey, we're going back to the office. Everyone has seven days. And so a bunch of our colleagues decided not to join us on that journey and left the company because they didn't want to work for an in-person company. And we wi…”

“I don't think Open Door had much of a culture. Transparently, I think what happens to companies when they're run by, like, professional managers is, like, culture atrophies.”

“And the result of that, by the way, very objectively is PayPal. Like over and over again, that company made all the wrong decisions because they cared more about today than 10 years from now. And guess what? It is now 10 years from now, and the company's in de…”

“Opendoor will be the most aggressive in-office public tech company.”

“I think being remote is an exceptionally bad idea for most companies.”

“I'm pretty sure Excel has done more damage to the world than any other software.”

“But let's be honest, most even growth companies just cosplay as learners. They have a whole bunch of things you're not allowed to say. A whole bunch of companies have like these religious things they believe that you're not allowed to question.”

“Mark's ability to understand risk adequately is just probably unparalleled in business history.”

“What most people end up doing Is doing this the wrong way, right? They go to SOC II saying, what can I build? And then they build the thing SOC II says you shall build. Which is why all enterprise software ends up being shit.”

“And usually for tech companies, like, your largest expense to an external vendor ends up being, like, your cloud provider. But for Opendoor, number one was millions of dollars written to a very large consulting firm.”

“So Open Door had gone fully remote. So at nine a.m. That Monday, I told the entire company, hey, Open Door is going to be back in the office next Monday. If you don't plan to be in one of these offices, we appreciate your help, but you're no longer with us.”

“Yeah, honestly, Opendoor would have died had it not been for maybe a dozen people.”

“So the first week in Open Door, I changed our career page. Our career page used to say something along the lines of, this is a happy place to work where we all care about each other, and by the way, here are all of our ERGs. Opendoor's career page now says, th…”

“You need to figure out which defaults are killing the company and change them violently. There must not be change management. Because you want the change to feel jarring.”

“We have built the AI exoskeleton around every human being at Opendoor, such that they can be three, four X more efficient than everyone else.”

“Companies cannot have multiple cultures. They just can't. They just die. If you allow a company to have many different cultures, What you end up creating is you lose all short form of communication. And you end up spending a lot of time aligning people such th…”

“In my first four weeks, I killed two entire business lines. Opendoor used to have, essentially, we provided general contractor services to other companies, which was, it was a profitable business for us, but it was not the mission of our company. Our job isn't…”

“My wife's plan, literally, genuinely, honestly, was that we would, like, sell everything we owned, leverage ourselves as much as we could to take Opendoor private, so we could fix it. So I called Keith back in, I think, April, and he was, hey man, I'm thinking…”

“The single largest expense on our income statement was millions of dollars paid to a well-known consulting firm whose advice can be approximated as the following. We paid him five million dollars for this. This voice was basically the following tweet. Do every…”

“So between the time, like you put your address in and you Got an offer. There'd be 11 human beings who touched that. That's insane. That's just an insane outcome. Like, today, zero human beings are in that loop in many of our flows. Like, AI does all of that.”

“Our earnings was the most watched earnings in history. The last National Open House we did broke records for how many people watched it. No. Yeah, by a lot, but not by a lot. We should fact check this, but I think at one point we had 55,000 live viewers.”

“There's no, like, we don't have a PR department. Like, if you email press at opendoor.com, get an email back saying, we don't have a PR department. If you want to talk to someone, DM Kaz on X.”

“I showed up on a Monday, my first Monday at work and I said, Hey everyone, by next Monday, we're back in offices. At that point, we didn't have offices. Like we didn't know where people were gonna go. So we had to like the team had to go sign leases, open up o…”

“We will get to a point where you will buy a home from Opendoor, and if you don't like it, you'll be able to return.”

“I think three years ago, this was an incredibly difficult problem that required human beings to visit homes and look around and look at the shape of the cart. Like, that's the real thing. If you're one side of the street that has a slope, the other side doesn'…”

“We will not choose to stay in a solely asset heavy world.”

“And if you think for a very long time, you're going to have 20% margin buying homes cheaper than someone else, you're just straight up dumb.”

“We don't have that at Shopify. At Shopify, if a marketer wants to create a new landing page, they have to go into GitHub. They have to know how to write some code. They have, like, this is a real thing, and our, so our marketers learn how to write some code. L…”

“The worst decision Meta probably made was Not being more publicly celebratory of Mark personally and Meta generally. I think Meta allowed, because the company was so focused on execution internally, it didn't spend that much time worrying about its reputation …”

“Because, like people overestimate the importance of what, and then massively underestimate the importance of how. Like, people just massively underestimate the importance of how in ways that are just, like, shocking still.”

“I'm very sure that the outcome will be more favorable to us. Like if you think about how LLMs work, you need something to train the machine on. And the fact that we are, we had this discussion in paper, we wrote our thoughts down and they made an outcome. It's…”

“Going remote was incredibly difficult for Shopify. It took us a very long time to get right. I can honestly tell you for the first six to 12 months, it just straight up wasn't working.”

“So if, I think if we knew how painful it would be, I don't know if we would have done it.”

“We don't build bespoke software. There's no if enterprise line anywhere in Shopify's code base.”

“And this Stripe-Shopify relationship Is likely the most value creating relationship in the history of software. It would have been Intel, Microsoft before Intel and Microsoft had had divorce is too hard a word, but had like the thing they did.”

“Commerce on the internet is slightly more weird than it would be if Yahoo had won. Yahoo Stores had won, which is like the Paul Graham product. I like Paul Graham a lot, but I'm very glad that his software at Yahoo did not win.”

“The biggest mistakes I have made in my career have all been of the same shape, unfortunately. And it's just, it's very, I'll tell you the shape. And I like, and it's a lesson I will perpetually learn. I need to relearn every single time. I have a limited the i…”

“Values need to be things that a reasonable person can take both the other side of.”

“The data behind this is undeniable for men, specifically for men, graduating from high school, getting some job experience and getting married in that order as soon as possible. Is more indicative is more indicative of success, including health, wealth, and ha…”

“Groups of people tend to have tendencies towards niceties. So everyone ends up telling each other nice lies. A series of white lies that take very off course. And the job of a founder type is to be, you know, a nuclear bomb of truth over and over again. First …”

“I sent my team, I have a blueprint that I sent to the entire company, because my job was to create strong, repelling forces. I.e., I wanted everyone who didn't like how I was going to run the company to quit.”

“The most dangerous people in any company, if you grab a two-by-two chart, are competent but not mission-aligned people. So your job is to identify who they are and help them move on as fast as possible.”

“The larger the room is, the less space there is for truth, right? But that is the death of companies. This is why big companies are so usually average.”