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CPO Paul Gubbay says Squarespace is training its AI tools with curation and taste

Will generative AI tools help people build better websites, or will they just fill the web with spam? With the recent launch of Design Intelligence, a new website builder full of generative AI tools, Squarespace is betting on the former.

I spoke with chief product officer Paul Gubbay about Design Intelligence and Squarespace’s broader AI strategy. Our conversation began with a glimpse at what other (unspecified) AI-powered website builders deliver when prompted to create a generic spa website: confusing, ugly websites.

This was, of course, a setup for a demo of Design Intelligence, which began with a few prompts allowing Gubbay to specify things like the kind of website he wanted to build and the personality of the brand being featured. The resulting website featured AI-generated design, text, and images, but it looked — for lack of a better word — like a “real” site, with plenty of options for further customization.

Gubbay argued that while other website builders have “scrambled very quickly” to launch AI features, those competitors are asking, “How can we take this technology and use it to stand out to our customers?” while Squarespace has been asking something a little different: “How do we take all these latest technologies and really use it to help our customers stand out?”

Read a transcript of our conversation below, edited for length and clarity.

When I imagine an AI website generation product, I imagine it looking like a prompt — like everything at the beginning of the demo. But here, with every step, you could still go in and customize it. It looks, in some ways, like Squarespace today. So I’m curious: How did you decide where you wanted the AI to step in and generate elements of the website versus where you wanted it to still be customizable by humans?

We’ve taken our time to really think about how these things come together. So we have this principle when it comes to building something like a website or anything visual: I know it when I see it. And I think that holds true for not just professionals, but for anybody.

Trying to build a website through a chatbot is really challenging. It’s like being in a car and typing in “turn left” or “turn right.” You want the system to be able to show you things, and when you see the thing you like, you want to go, “OK, that’s it.” But then you don’t want to be limited by that; you want to be able to continue playing. We want it to feel like a playground.

And so for us, it really was taking this “I know it when I see it” concept. And every time the team came and said, “How about we add a chat? How about we do these things that everyone’s doing?” we were like, “I don’t think that’s really the way people want to do this.” That just became the model for us, and once everyone adopted that, it became very natural for all of us just to think through that ideology.

It was very important for us, also, that we treat the customers’ information that they give us with a lot of respect. You’re telling us something about who you are, you’re entrusting us to take that and use it effectively for you. So we wanted to make sure that the concepts that we showed you in Blueprint would carry through into the system as well, so that you would feel like those choices you made up front weren’t just for naught.

Image Credits:Squarespace

You also talked about this idea of curation and technology. Often those things are set in opposition to each other, but it sounds like you’ve actually tried to build curation into the technology. You even said that you have a curation engine. Can you talk a bit more about what that looks like?

Our CEO says this sometimes; I think it’s true: The fact that we have text generation inside of our website tool, it’s great. But you could also go to Open AI and ChatGPT, type in something, get the text, and copy and paste it [into Squarespace], and that’s fine as well. The challenge a lot of people have is knowing how to prompt those engines the right way to actually get the right output from them.

We have a very specific, proprietary point of view on how we prompt engines and how we curate the content that comes out of them, to get the look and feel and the views that we think are going to be really valuable to our customers based on our experience, based on what they’re telling us, and based on our taste.

AI imagery is a great example of that. We built our whole library of how we prompt [AI models] specifically to get the type of imagery that we want to get out, that we feel is very Squarespace, very right for our customers. We tag and curate those things, and then we feed that back into the system again.

We do that when we look at color palettes; we do that when we think about layout switching. That’s the curation element. It’s our design and creative team spending lots of time thinking about: How do these elements come together? How do we prompt engines? How do we choose what comes out of this and discard the things that we don’t want that come out of this? We keep getting better and better, so you don’t have to do it. The whole point of coming to us is that you don’t have to do it.

It sounds like part of your approach is, you’re not necessarily trying to build all these models yourself. You’re focusing on how you present it and make it accessible and bring it together.

Look, we’re not the LLM experts in creating all these different types of content. We leverage them. We leverage Google, we’re leveraging OpenAI, Anthropic. We have great partnerships. But for us, the secret sauce is how we’re prompting and curating that content as it’s coming out, and making sure it fits what we know about you.

Obviously, Squarespace has made it easy to create and customize websites already. How do you think bringing more generative AI into the process will change that ecosystem? Are Squarespace websites going to look different than they do today?

I’d like to think that they’re going to look even better. It’s very, very important for us, and it’s always been incredibly important for us, that design is always at the forefront. People come to Squarespace because they believe that design is going to make a difference. And a big part of that difference is not just capturing their brand and who they are, but it’s about making sure that the thing that gets pre-created, at the end of the day, feels bespoke.

When you ask a question like that, it could imply they all look the same in some way. And that’s absolutely not what we would want, right? So I think we are going to give people the tools to get even better results faster, but we will always make sure that it’s going to adhere to the vision of what they want.

Squarespace works very closely with designers; you just wrapped up a whole event with design partners. How do you think designers, especially Squarespace partners, should be looking at a tool like AI? To what extent should they see it as a threat versus an opportunity?

I think it’s important to look at it as an opportunity. AI technology is clearly a huge part of our future, and just like any new technology, learning how to leverage it and use it the right way is going to enhance what you’re able to do. I 1 million percent do not believe it replaces design. It’s meant to enhance it. We will continue to play our role to ensure that it enhances it for our customers and our creators.

We just had Circle Day with many [design] professionals. And when I think about something like design intelligence, for me, it just helps them bring a vision to life faster to share with a customer. But of course, [customers are coming to us] to implement all of the things that they want on top of that. If we can inspire them with some choices that they will then change and go deeper on, fantastic. We’re just going to make the job faster for them and maybe easier for them, but we would never replace them.

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TechCrunch Mobility: Uber bets on its former CEO

Welcome back to TechCrunch Mobility, your hub for the future of transportation and now, more than ever, the role AI is playing in it. To get this in your inbox, sign up here for free — just click TechCrunch Mobility!

Tesla kicked off earnings season — at least for this sector — and the shareholder letter, along with Elon Musk’s remarks during the conference call, provided some pretty incredible disclosures I imagine have some investors concerned, or at least puzzled. 

Tesla has backed off previous promises to reach “volume production” of the Cybercab, Tesla Semi, and Megapack 3 in 2026. And while the company has publicly touted expansions of its Tesla Robotaxi service into new cities in Florida and Texas, the quarter-over-quarter data shows a drop in paid robotaxi miles. 

Senior reporter Sean O’Kane took a closer look at a graph shared in Tesla’s shareholder letter.  At a passing glance, the chart appears to show steady growth in paid robotaxi rides between August 2025 and June 2026, O’Kane notes. But the numbers displayed are cumulative, and when broken down by quarter, they show that Tesla’s Robotaxi fleet of Model Y SUVs carrying paying passengers covered around 1.1 million miles in the first quarter. That fell to roughly 700,000 miles in the second quarter, a decline of about 36%.

Musk also disclosed during the call that Tesla needs to accumulate driving data specific to the Cybercab before it can put large numbers of the vehicles on the road. That isn’t terribly surprising; the Cybercab is new, after all. But the reason got my attention. He explained that Tesla has to accumulate miles using Cybercabs retrofitted with steering wheels and accelerator and braking pedals so it can calibrate to the Cybercab chassis.

This marks a change from the company’s previous claims. For years, Tesla has said its fleet of nearly 10 million customer cars has been collecting data that could be used to train its advanced driver-assistance system, Full Self-Driving (Supervised), and future robotaxis. Musk’s explanation suggests there is a misalignment between that fleet data and how it’s applied to the Cybercab.

On the financial front, Tesla’s Q2 earnings show a company plowing money into its next generation of products (CapEx has doubled, and the company is back in negative free cash flow territory). And even though revenue is up, the boost wasn’t enough to offset the cost of doing business. The company’s net income fell 5% year over year.

Deals!

money the station
Image Credits:Bryce Durbin

Travis Kalanick burst back onto the robotics and mobility scene earlier this year with Atoms — a rebranded holding company atop his ghost kitchen project — and a deal to acquire Anthony Levandowski’s industrial automation startup, Pronto. Now the Uber co-founder and former CEO has $1.7 billion in capital to play with. VC giant Andreessen Horowitz led the round with participation from Bain Capital, Fifth Wall, and Uber. Ben Horowitz will join the company’s board following the investment.

This may seem inconceivable for those who remember Kalanick’s resignation from Uber’s top leadership spot nearly a decade ago — and the string of scandals and lawsuits in the year leading up to his departure. What’s even more incredible is that Uber participated in the funding round. The Information reported Uber invested $100 million into Atoms; conversations I’ve had since confirm that figure and provided new information, including that the investment was made six months ago.  

Reminder: In 2016 and while Kalanick was CEO, Uber acquired Levandowski’s self-driving trucks startup Otto. Less than a year later, Levandowski’s former employer Waymo (Google self-driving project) sued Uber for trade secret theft. The companies settled on the fifth day of the trial. 

There is a lot of history, much of it messy, between Kalanick and Uber (not to mention Levandowski). But it appears the ride-hailing company is still willing to invest in them. 

So what is Atoms going to do with this capital? The details are vague, but a company email from Levandowski suggests that Pronto will be a big part of those plans. 

The email states that “Atoms is investing heavily in Industrial AI and physical automation applied to mining and transport.” And later, “Pronto is a core strategic priority for Atoms, and this round is designed to accelerate exactly what matters most to your operations: scaling practical, OEM-agnostic autonomy.”

Other deals that got my attention …

Einride, the Swedish electric and autonomous trucking company, agreed to acquire EV charging startup Flipturn in an all-stock deal worth $38 million.

IBM agreed to buy HRL Laboratories, a quantum computing research lab jointly owned by Boeing and General Motors

Sila, the battery materials startup, raised $300 million in a round led by Atreides Management and Sutter Hill Ventures with participation from 8VC, Bessemer Venture Partners, Matrix Partners, and funds and accounts advised by T. Rowe Price Associates Inc. The money will be used to expand Sila’s factory in Washington state to produce enough anode material for more than 100,000 EVs.

Notable reads and other tidbits

Image Credits:Bryce Durbin

Aurora had some news this week that didn’t get a ton of attention, but probably should. The company launched its second-generation driverless trucks, which include new hardware that is smaller, as well as upgraded sensor-cleaning systems and extended range lidar — all of which is built for a million-mile service life. The initial fleet will be modest and used on its Dallas-to-Houston route. The fleet will eventually reach 200 driverless trucks by the end of the year and will be used to haul freight for customers like Hirschbach, Uber Freight, McLane, and Detmar, the company said. Importantly for Aurora, these trucks do not have a human observer in the cab.

Ford is turning to Apple for its next generation of EVs. Specifically, Ford is going to integrate Apple Maps navigation and mapping, using a new set of developer tools called MapKit for Automotive, into its new line of electric vehicles, starting with the $30,000 midsize truck in 2027. I asked Ford what this means for Google, which is an existing partner. A company spokesperson told me the Apple announcement “does not change the role of Google Automotive Services across our current and near-term production programs.”

The Insurance Institute for Highway Safety released a study called “Rise of the machines: crash experiences of highly automated vehicles and human drivers.” The organization used a far more clickbaity headline (Waymo’s driverless cars crash less often than people) to direct folks to its work. Unfortunately, that headline misses part of the point. The study does provide evidence that Waymo’s current robotaxis have lower crash involvement rates than human drivers. “Overall, when including police-reportable crashes, Waymo’s crash rate was 68% lower than that of human drivers,” the study reads. It also, importantly, concludes that national-crash and vehicle-miles-traveled data collection for Level 4 vehicles “can be improved for more timely and accurate safety evaluations.” 

Mobileye founder and CEO Amnon Shashua plans to step down from the top leadership post after nearly three decades, just as the company pushes into robotaxis and humanoid robots.

The National Highway Traffic Safety Administration will look into developing new requirements for automakers to ensure drivers and passengers can safely exit their vehicles — the result of a petition that asked the agency to open a safety defect investigation into the emergency mechanical door release design on 2022 Tesla Model 3 vehicles. To be clear, this doesn’t mean there will be new rules. 

Rivian has sued the U.S. government for a “full refund” on tariffs paid under President Trump’s “Liberation Day” taxes, which the Supreme Court later ruled unconstitutional. 

Two Volkswagen engineers were charged with securities fraud after allegedly profiting off of insider information related to the German automaker’s joint venture with Rivian. 

Waymo is having internal discussions over how to end its contract with Uber, the Financial Times reported. Close followers of this partnership might have read this, rolled their eyes, and said “DUH!” But there are some interesting details in here, including that Uber-Waymo contract that covers Atlanta and Austin ends in May 2028. Uber told TechCrunch that Waymo says it intends to launch its own app in Austin and Atlanta in January 2028.

WhatsApp is rolling out a suite of new features, including a revamped Apple CarPlay and Android Auto experience.

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Hugging Face CEO calls for ‘radical transparency’ after ‘unprecedented’ OpenAI hack

After OpenAI recently admitted that one of its models had breached the systems of AI platform Hugging Face, Hugging Face’s CEO Clem Delangue posted on X that he was flying to San Francisco to have “a little chat with that ‘rogue agent.’”

Then, in a follow-up post on Saturday, Delangue outlined what he’d asked for from OpenAI. He said he called for “radical transparency,” asking OpenAI to “release the traces from the ‘rogue’ agents so the entire research community can study what happened.”

And he also wants “more capabilities for defenders,” calling for OpenAI to commit $100 million worth of computing power “to help the Hugging Face community build powerful cyber defenses with the best open and closed models.”

Delangue added, “The first autonomous agent cyberattack is an unprecedented event. It deserves an unprecedented response!”

Despite the autonomous nature of the attack, cybersecurity experts suggested that it could also be blamed on human error — namely, OpenAI’s apparent failure to properly configure what should have been a fully isolated testing environment.

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Inside one London founder house rewriting the founder-house rules 

Six twentysomethings in East London have built what they say is the anti-San Francisco hacker house. The goal is a “holistic improvement in life,” rather than “12 weeks, Demo Day is coming,” Rowan Aldean, 26, explained. 

Intrigued, I spent an afternoon visiting the house, meeting its residents, and doing a vibe check. I arrived after Aldean escorted me through the clean sidewalks of a new East London development to where the six-story building stood facing the water. 

The house is called the London Island Founder House — or “Lift House” — and Aldean and his wife, Zahraa, 22, an upcoming pharmaceutical research PhD candidate, have lived there since May, just a few months after it officially launched in March. Aldean sold his previous company last year for millions, he said, and now runs an “applied AI” startup that helps companies learn how to deploy agents. 

Like all hacker houses, Lift House is part startup workspace, part co-living space. The house is named after both its lift — that is, its elevator — and its mission to uplift tech founders, Aldean said. It’s one of the very few co-living hacker houses to exist in London (compared to San Francisco, where dozens — if not hundreds — are scattered around the city at any given time). 

Lift House is a bet that U.K. founders can build successful companies without mimicking the over-the-top hustle culture of Silicon Valley.  

Founders have described stories of San Francisco hacker houses illegally running in warehouses, throwing full-on galas, or setting up in a tent or espousing punishing, 72-hour sprints typical of the “996” work culture.  

“I don’t expect the performative and over-the-top events will be a thing here,” Aldean said, and pointed to one of London’s most successful AI companies, DeepMind. “They’ve won Nobel prizes and built frontier innovation without any song and dance.”  

Instead, Lift House is part of a trend called “Londonmaxxing,” in which founders attempt to optimize everything the London tech scene offers. The London ecosystem feels less showy and less startup bro-y than San Francisco, but its founders share similar ambitions: success, wealth, and market domination.  

London AI startups have raised $12 billion so far in 2026, out of $14.7 billion raised by all London startups, according to Dealroom. Six companies have raised more than $500 million: Wayve, Superintelligence, ElevenLabs, Recursive, Ineffable Intelligence, and Isomorphic Labs, the latter three of which were founded by DeepMind alumni. 
 
The excitement from AI has boosted the morale of the U.K. tech scene, inspiring a new generation of founders, like those in the Lift House, to take big swings. 

L-R; Luke, Zahraa, rowan, varun, david, presence, and wan. Varun is the only one who doesn’t live in the Lift House. Image Credits:TechCrunch

Journaling vs. demo day  

The timeline for living on Lift House is flexible — some people have stayed for a month; others intend to stay for at least six months. They buy their own groceries, Aldean said, although they often cook together and share ingredients. Cleaning is split among the group. Everyone declined to share information about the rent they pay. 

The residents of Lift House aim for a balanced approach toward ambition, each one of them tells me — an almost unheard-of idea by San Francisco startup standards.  

On Sundays, the group will journal together, a practice introduced by David Amor, 28, who runs a brain coaching and training company, helping founders and business leaders understand more about their brain and how it can help optimize business performance. The idea of journaling is to help everyone track how much time they spent in nature that week, how well they ate, and how much they moved their bodies.  

“I’m eating healthier, working out more, and sleeping more,” Luke, 27, who runs an AI-marketing company, said about living in the house. “I always make sure to have lunch now, which is something that is simple, but I wasn’t doing before I lived here.” (Luke asked that his last name be withheld.)  
 
Tuesdays evenings are for volleyball, where the founders play on the house team in a local league.  

After dinner on other evenings, Wan Ying L, 25, who just left an AI startup and is working on a new idea, might play the piano in the living room. Sometimes the group plays Catan or visits art exhibitions together.  

Presence Plumb, 25, is a tech strategist. She likes to host rooftop dinner parties, serving dishes that reflect the different nationalities in the house — from Iraqi to Spanish — while invited founders, researchers, investors, and operators chat about tech trends and investments. 

“It’s a bit calmer, balanced, authentic in a way,” she said of people in the London ecosystem. “They don’t want too much of that only startup tech bro vibe. They want a bit of balance.” 

Each founder follows their own schedules for a typical workday. Amor, for example, is up by 8 a.m. and gives himself exactly 30 seconds after waking up before jumping into his morning work. “I have a clear objective of ‘this is what I want to do in the first half of the day, when there’s no distractions.’” After his morning work routine, he takes a cold shower, “because it increases your dopamine by 250% and that gives me that motivation, that spark,” he said.  

Wan playing the pianoImage Credits:TechCrunch

Luke, meanwhile, is up at around 8:30. His co-founder, Varun, 27 (who asked that his last name be withheld), typically travels to the Lift House to co-work, and the duo starts work at around 9 a.m. with a team call.  

Aldean rarely wakes before 10 a.m. unless something big is happening, like a “crazy angel [investor] call,” he said.
 
When asked what makes this house uniquely British rather than a wellness-focused Silicon Valley founder house, Aldean joked: “Well, we drink tea together like Brits, and in SF folks just drink filtered coffee.” 
 
More seriously, he spoke of how British founders face a different kind of pressure than those in the U.S. They must navigate a cultural aversion to risk, an inclination toward humility, and a shame associated with failure. Instead of forgoing sleep for hustle and grind, they deal with what they call the “tall poppy syndrome,” when the media builds one up only to ruthlessly tear them down should they become too successful, investors and founders say. It makes some founders in the ecosystem wary of displaying too many wins.  

Still, Luke said London is a strong choice for an early-stage founder: There’s a good network, ample early capital opportunities, and an option for a life outside of tech. In many ways, it is much more like New York culturally for founders than in San Francisco.  

“London is so diverse that if you look properly enough, you’ll always find something fun to get involved with,” Amor added, “whether that’s a founder-run club, wellness events, [or going] to jazz nights.” 

Luke and Varun write marketing terms on the whiteboard. They stand for top of funnel (TOFU), middle of funnel (MOFU), and bottom of funnel (BOFU).Image Credits:TechCrunch

Luke and Varun largely avoided venture capital funding by taking advantage of the U.K. government’s SEIS/EIS, which is supposed to help attract more angel investments into local startups. “There’s people who will pay basically the same rate of tax if they give us the money versus if they pay income tax,” Luke explained as another reason he liked starting out in London.  

Aldean also feels the London ecosystem is less cutthroat than the Valley. He recalls his days living in a hacker house in the Bay — everyone’s desk had to face the wall, and it was heads-down, product-building. He felt the ecosystem, at times, was too willing to gossip, which is apparently done quite differently in the U.K.  

“There’s nothing like ‘oh my god did you hear that the CTO just, like, did this,’” Aldean said. “It’s like you’re always worried,” he said, that someone would spread negative stories, especially if it benefited them.  

Aldean also thinks London startups, more than Silicon Valley ones, sell into slow-moving large corporations rather than to each other, meaning one could build without having to kiss up or posture to get their peers to like them.  

To the selling point, Varun and Luke mentioned another difference between the U.S. and U.K. ecosystem. “It’s a relatively fleeting market,” Varun said of the U.S. “You get quick wins. Here, it’s hard to close a customer, but if they close, they stay with you longer.” 

Coming to America

Eventually, though, the road for many U.K. startups goes straight to the U.S. 

In the U.K., founders have access to affordable top talent from universities like Oxbridge and a time zone that makes it easier to work with the rest of Europe, the Middle East, Asia, and parts of North America. In the U.S., however, they have access to the world’s largest economy and, most importantly, a lot of investors willing to write large checks, from pre-seed to growth stages.  

“It’s almost like a factory line in a way,” Varun said. “You start here, and then you expand there or vice versa.”  

American investors are also playing a role in luring British talent away from the country. I told the Lift House residents about one startup founder who said a top investor wouldn’t even back the company unless she relocated to the U.S. She ended up doing so, though decided to keep her family based in the U.K. to raise her children.  

“We had an investor in Miami who said the same thing,” Luke said of an investor trying to get him and Varun to move to the U.S. “It’s quite a common practice.” He and Varun have already begun their U.S. expansion, and despite loving London, the duo hasn’t ruled out moving to the U.S. to be closer to their customers.  

David, who has a brain coaching startup, is the one who introduced journaling into the household. Image Credits:TechCrunch

That’s the tension bubbling beneath not just the U.K.’s tech ecosystem but most of Europe’s. “I work with a lot of people trying to support the European ecosystem more,” Plumb said. 

Yet, founders “talk about London; everyone is bullish on the country until they get the opportunity to leave,” Aldean added. 

The Lift House lease has about a year left, and there is sentiment in the house to keep it going for as long as they can. After all, there aren’t too many in London, though the city sees many short-term gatherings, like the Solana Hacker House meet-up series. Some of the more public co-living hacker houses are part of a global chain, like the San Francisco-based network The Residency, which expanded into London last year, and BaseJump, which is announcing a London version of its hacker house program soon

In 2024, two founders tried the opposite version of the Lift House called “The London Founder House,” which Sifted covered under the headline “The people here don’t want work-life balance.” That home is noted as London’s first-ever hacker house, and though it wound down last year, it left an influence through its concept, events, and connected players around the ecosystem. To even be considered for the London Founder House, one had to have raised at least half a million dollars.  

For Lift House, prospective residents need to show a hobby outside their companies and an interest in fitness. It’s the same pitch many in the Londonmaxxing ecosystem are using to keep people from leaving: That here one can have it all. 

“The culture is to build something that lasts,” Aldean said, “not necessarily burn out chasing a flash.” 

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