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How I Built This with Guy Raz

Advice Line with Anthony Casalena of Squarespace

with Anthony Casalena, Bob Zukowski, Stacey Bernstein, Mahak Mohan

Published November 20, 2025
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About This Episode

In this Advice Line episode of How I Built This Lab, host Guy Raz and Squarespace founder and CEO Anthony Casalena answer questions from three early-stage founders. They first discuss how Squarespace has evolved, including its role in a changing AI-driven web and its AI-enabled features. Then they advise a custom mattress entrepreneur, a clean first-aid brand founder, and the creator of an eating-disorder recovery app on branding, distribution, go-to-market strategies, and leveraging early users, before Anthony shares a key retrospective lesson on following his gut faster.

Topics Covered

Entrepreneurship Product development Artificial intelligence Retail distribution Pre-awareness marketing Therapy Web design and branding Women's health advocacy Personal narrative

Disclaimer: We provide independent summaries of podcasts and are not affiliated with or endorsed in any way by any podcast or creator. All podcast names and content are the property of their respective owners. The views and opinions expressed within the podcasts belong solely to the original hosts and guests and do not reflect the views or positions of Summapod.

Quick Takeaways

  • Anthony views websites as more relevant than ever in the age of AI answer engines, because they supply source material and still handle core business interactions like contact forms, bookings, and purchases.
  • Squarespace has embedded AI and machine learning into many touchpoints, including a Blueprint AI onboarding flow that was recognized as one of Time's 100 best inventions of the year.
  • For a premium, highly technical product like custom mattresses, a credible, modern website and clear scientific messaging are essential to justify high price points and build trust.
  • Small physical-product brands can benefit from omni-channel strategies that place items in high-convenience contexts (like hotels or airports), where design and impulse needs drive trial.
  • Founders with limited budgets should lean heavily on early super-users as authentic ambassadors, especially for sensitive areas like eating-disorder recovery.
  • Packaging and on-product copy need to quickly communicate the "why" behind a product (e.g., fewer chemicals, better for sensitive skin), not just a catchy name.
  • For digital products, it's important to question whether an app is necessary on day one and to consider web or other entry points given consumer app fatigue.
  • Anthony's main retrospective advice to his younger self is to notice decisions he consistently delays and move faster on them, trusting his gut more.

Podcast Notes

Introduction and format of the Advice Line episode

Guy introduces the Advice Line concept

Description of what the Advice Line does[2:54]
• Guy explains that the Advice Line is where they try to solve listeners' business challenges.
• Each week, a legendary founder and former guest joins him to help advise callers.
How to become a caller on the Advice Line[2:54]
• Listeners who are building something and need advice are invited to call in.
• The call-in number is 1-800-433-1298, and callers should leave a one-minute message describing their business and issues or questions.

Conversation with guest founder Anthony Casalena and Squarespace update

Reintroduction of Anthony and Squarespace origin recap

Anthony's previous appearance and Squarespace founding story[3:37]
• Anthony was first on the show in 2019, when he told the origin story of Squarespace and lessons from growing it.
• He founded Squarespace in 2003 as a 21-year-old college student.
• Guy recalls stories of Anthony racing up and down I-95 and physically swapping servers himself.
• Squarespace began because Anthony was frustrated by the lack of easy, good tools to build websites and initially built the software for himself.
• A friend offered to pay $200 to use what Anthony had built, which triggered the business opportunity.
Recent milestones for Squarespace[4:44]
• Since the previous episode, Anthony took Squarespace public.
• The company surpassed a billion dollars in revenue.
• Last year, the company was bought by a private equity group, and Anthony describes this as taking it private again.
• Anthony has remained on as CEO and chair throughout these transitions.

Anthony on what it feels like to have "bosses" after going private

Perspective on who the "boss" really is in a company[5:16]
• Anthony says that when running a company, you always have a boss, whether shareholders or, even if you own 100%, your customers.
• He says nothing has substantially changed in his or the company's day-to-day from being private again.
• He notes they could have remained public and were fine with either structure, but thought going private was a little better.

How Squarespace has expanded beyond simple websites

Overview of Squarespace's current offerings[6:18]
• Guy describes Squarespace as more than website-building; it now offers tools for small businesses to run their entire business online.
• Anthony says they offer a complete set of tools for entrepreneurs, small businesses, and others to get online.
• What began as a publishing product centered on websites and blogs evolved into portfolios and more.
• Squarespace now includes robust e-commerce tools for physical product sellers and service providers.
• They own other companies, such as Acuity, a scheduling product that helps people sell time.
• They acquired the assets of Google Domains and, by brand, are now probably the third biggest domain registrar.
• Squarespace is among the biggest website builders and one of the biggest resellers of business email through Google Workspace.
• Anthony summarizes that they play in many lanes that help people get online.

Relevance of websites in the era of AI and answer engines

Guy's question about AI chatbots and search behavior[8:23]
• Guy notes that more people are using chatbots for search instead of traditional search engines.
• He asks how this shift changes what it means to have a website, given that a website is a business's storefront.
Anthony's argument that websites are more relevant than ever[9:09]
• Anthony explains that websites provide the information that "answer engines" crawl and use, whether from older or more recent data.
• When answer engines lack a real-time answer, they still go to the web, so websites matter both in the index and for real-time interactions.
• Most small-business interactions-such as contacting the business, submitting forms, booking appointments, or purchasing products-still occur via direct interaction facilitated by websites and similar tools.
• Squarespace facilitates these interactions regardless of whether the customer started on a search engine, answer engine, or social network.
• Anthony says they are happy with how Squarespace is positioned in this era.

Squarespace's use of AI and the Blueprint AI product

Guy asks about AI tools within Squarespace and their pace of change[10:00]
• Guy notes that Squarespace already has AI tools to help build websites and designs very fast.
• He observes that the pace of AI change is so fast that it's hard to anticipate what will be available even a year from now and asks what that means for Squarespace's business.
Anthony on AI as a tailwind, not a threat[10:09]
• Anthony says AI has been a phenomenal tailwind for them.
• He is not worried about people using AI to code websites who couldn't code before, since Squarespace has let people avoid coding for two decades.
• He notes that AI and what used to be called machine learning are embedded into every aspect of their product.
• Their Blueprint AI product, which is the primary onboarding path when users click "get started," was named one of Time's 100 best inventions of the year.
• Anthony says they currently have AI enabled at probably 15-20+ touchpoints in the product.
• Use cases include optimizing sites for SEO and what they call AIO (optimizing for answer engines) and helping generate imagery.

Caller 1: Custom Sleep Technology and custom mattress business

Introduction to caller Bob Zukowski and his business

Bob's elevator pitch[10:00]
• Caller introduces himself as Bob Zukowski from Newtown, Connecticut, founder and CEO of Custom Sleep Technology Incorporated.
• He describes the company as a technology company that combines artificial intelligence with proprietary software to design and build mattresses specific to each sleeper's unique body characteristics.

How the custom mattress process works and pricing

Data collection and AI design process[10:28]
• Bob explains that the website has a body profile questionnaire that collects information about physical characteristics of sleepers.
• After the questionnaire is complete, AI mathematically designs the mattress.
• The software delivers these designs instantly to the potential customer, followed by an email with a complete proposal.
Materials used and rationale[11:10]
• Bob says they use exclusively Talalay latex because it comes in multiple densities.
• Different densities are used to support shoulders and hips separately, aiming to reduce pressure on pressure points and align the spine.
• He states that by putting the body in the right position, sleepers have the greatest opportunity to achieve high-quality REM and slow-wave sleep.
Pricing and dual-sleeper configurations[12:18]
• Bob says a queen mattress is in the $3,800 range and a king is in the $4,500 range.
• He confirms they can design a mattress for two people with different needs; each side can be designed specifically for each person.

Bob's background and motivation for starting Custom Sleep Technology

Experience in the latex manufacturing industry[12:38]
• Bob previously worked for the company that manufactures the latex.
• His job was to work with major mattress brands to incorporate Talalay into their products.
Insight that existing brands were not prioritizing sleep quality[12:22]
• Bob came to believe that major brands' number one priority was not how customers slept, but ensuring the mattress would not fail in the field.
• He began doing his own research, pressure-mapping friends and family.
• He learned that weight distribution varies greatly depending on physical characteristics, sleeping position, and height.
• Using eight different densities of latex, he realized he could build mattresses personalized to individual sleepers.

Bob's main business question: distribution and growth strategies

Challenge with traditional retail channels[13:57]
• Bob says they are not well-suited for traditional big-box retail channels.
Exploring partnerships and licensing[14:07]
• He asks whether they should consider partnerships or license agreements with wellness tech companies, fitness organizations, or professional athletes to grow consumer awareness.

Anthony and Guy's feedback on website and branding

First impression of Custom Sleep Technology's website[14:35]
• Anthony, identifying himself as a "website person," says the site looks a little dated.
• He emphasizes that for a premium, scientific product, branding needs to catch the visitor and build trust.
Need for compelling branding and a scientific message[15:39]
• Anthony says he is skeptical of luxury-material narratives (like horsehair or gold) and is more persuaded by scientific explanations.
• He suggests positioning the brand around science and measurable sleep benefits rather than exotic materials.
• Guy reinforces that a dated site undermines willingness to spend $3,000+ and that most customers will not talk to Bob directly; the website has to speak for the brand.

Discussion of potential partnerships and licensing

Using partners to scale awareness and distribution[17:37]
• Guy suggests that, as a small brand competing with large mattress companies, Bob might partner with wellness tech or fitness brands.
• He imagines arrangements where an existing brand uses Custom Sleep Technology as the technology behind a customized mattress offering, potentially marking up the price.
• Guy notes this could let Bob deliver his technology under another brand umbrella without having to build full-scale consumer brand awareness from scratch.
Importance of explaining Talalay and customization to consumers[18:48]
• Guy admits he doesn't know what Talalay latex is and points out that the website needs to explain such terms clearly.
• He emphasizes that the value proposition-"we make a mattress for you specifically"-is different from standard "personalized" claims in the market and must be highlighted.

Caller 2: All Better Co and reimagining the first-aid kit

Introduction to caller Stacey Bernstein and All Better Co

All Better Co's focus and flagship product[25:13]
• Caller introduces herself as Stacey Bernstein from Los Angeles, co-founder of All Better Co.
• She says they are reimagining mom's first-aid kit with "better for you, better for the planet" daily skin health essentials.
• Their current product is the "Don't Scratch That" pen, an award-winning proprietary formula that replaces hydrocortisone for anti-itch and anti-inflammatory use.

Sales channels and current traction

Where All Better Co products are sold[25:42]
• Stacey explains they are DTC, on Amazon, and in about 100+ retail locations across the U.S.
• Retail partners include Erewhon, some resorts, and other locations, as they test which channels work best.
Sales figures and bootstrap status[26:48]
• She notes they are a bootstrap company and have used organic seeding and scrappy tactics to gain traction.
• They came out strong in DTC and then began testing retail, with some margin hit when entering retail.
• So far they have about $200,000 in lifetime sales.

Origin story and target customer

How the idea emerged from personal experience[27:16]
• Stacey comes from a brand background, creating immersive experiences for families and often speaking to families.
• During COVID, her co-founder called about her daughter's severe mosquito bite reactions, which required prescribed steroids.
• Her co-founder's children also dealt with eczema and sensitive skin, so both were searching for safer everyday solutions.
• They joke that, like many moms, they "solve the world's problems in the parking lot," and decided to make the products they couldn't find.
Demographic versus psychographic targeting[29:30]
• Stacey says their demographic is "anyone with skin," but their primary target is moms.
• She calls moms the original influencers and gatekeepers to their communities.
• They design products three steps ahead, as moms do: travel sizes, easy dispensers (like lip-gloss-style for one-handed use), and packable formats.
• They also attract Gen Z and younger users who appreciate travel-friendly, easy-to-use formats.
• All products are made to be chemical-free and as clean as possible.

Stacey's main question: shifting behavior in a legacy category

Challenges of the first-aid category and legacy competitors[30:34]
• Stacey notes the first-aid aisle is not the "sexiest" category and many people don't realize their current products may do more harm than good.
• They face legacy brands like Neosporin and Band-Aid.
Core behavioral and messaging challenge[31:06]
• Her question is how to get consumers to rethink products that have been in their cabinets forever.
• She wants people to buy their products before they need them and understand why All Better Co's products are better.

Anthony and Guy on channels, context, and education

Potential of travel and hotel partnerships[31:18]
• Anthony shares that he discovered some brands via hotel partnerships where products were placed in rooms as quasi-free samples.
• He suggests All Better Co could partner with hotels or resorts, especially family-oriented chains, to provide products in rooms.
• Stacey notes they are already in about six Four Seasons properties and some AutoCamp locations, but sees larger chains like Hilton or Hyatt as attractive targets.
Impulse and convenience purchases (airports and cash wraps)[34:25]
• Guy emphasizes the importance of convenience purchases, citing airport shops where travelers will pay high prices for items they forgot.
• He suggests All Better Co products could sell themselves in airports, given their design and name, especially if packaging quickly conveys benefits.
• He notes the brand could live at cash wraps as impulse buys or in travel sections where pressure to solve a problem is high.
Educating consumers about ingredients and harms[35:16]
• Stacey mentions that many bandages today contain "forever chemicals" (PFAs) and sit in landfills, and that people often don't think about what they put on their skin.
• She notes dermatologists often advise against using Neosporin because it can cause more harm than good and has higher allergy risk than many realize.
• Guy points out that education alone is an uphill battle without large budgets and that purchases still mainly depend on convenience, price, and effectiveness.
• He argues All Better Co already has a product that works and looks good, so focusing on omni-channel distribution and packaging clarity is key.
Improving packaging and communicating the "why"[36:26]
• Guy observes that packaging says things like "Better bandage," "bamboo bandage," "biodegradable," and "latex-free," but does not clearly explain why it's better.
• He references RXBar's simple macro labeling and notes that food brands list protein, carbs, and fiber prominently; he suggests similar concise messaging for skin products.
• He gives Method soap as an example of a brand that succeeded by being beautiful and working well, rather than leading with organic/plant-based messaging.
• He suggests on-pack phrases like "better for sensitive skin" or "fewer chemicals" and comparative statements that stop short of naming competitors.

Caller 3: Kahani and an eating-disorder recovery companion app

Introduction to caller Mahak Mohan and Kahani

What Kahani is and aims to do[40:34]
• Caller introduces herself as Mahak Mohan from New York City, co-founder and CEO of Kahani.
• She describes Kahani as a personalized recovery companion for eating disorders.
• Kahani applies evidence-based therapies in bite-sized format, personalized to an individual's goals, patterns, triggers, and behaviors.
• The goal is to provide a 24/7 companion, since recovery doesn't only happen during therapy sessions.

Current status of Kahani and upcoming App Store launch

Development history and funding[41:25]
• Mahak says they built Kahani while she was at Stanford Business School, partnering with leading clinical psychologists.
• After previously speaking with Guy, they closed their pre-seed round at the end of June.
• They are now building the second version of the app.
Design goals for version two[41:54]
• Mahak describes v2 as a reimagined landscape sitting between gamified, engaging consumer apps and overly clinical tools.
• They want a blend of skill-based progression, so users feel like they are recovering, without overemphasizing gamification.
• They are about to come out of private beta and launch on the App Store in the next couple of months.

Mahak's main question: go-to-market for an App Store launch

Seeking unique and effective launch strategies[42:39]
• Mahak asks what unique go-to-market strategies they can use to create the most effective launch for their target demographic.

Anthony's perspective on app fatigue and discovery

Questioning whether Kahani must be an app[43:28]
• Anthony notes there's significant fatigue around installing new apps, and he feels it personally.
• He suggests imagining Kahani as if it were not an app at all and asking where and how people would find it.
• He also asks whether it could start as a website that leads users to the app once they see value.

Defining Kahani's target users by psychographics and care pathways

Who Kahani is best suited for[44:33]
• Mahak says they focus less on demographics and more on psychographics: people who are motivated and at a certain stage in recovery.
• Ideal users are not in denial, have often gone through multiple treatment centers and higher levels of care, and are now focused on recovery due to a larger life goal.
• Two key discovery moments are when someone comes off a treatment center or higher-acuity care, and when they are in outpatient therapy but need support between sessions.
• Such users may already be engaging in community spaces like Facebook groups or TikTok chats.

Early traction, pilot results, and potential ambassadors

Pilot user base and outcomes[46:09]
• Mahak says they have about 100 users who have tested the app.
• They saw a 23% symptom decrease in four weeks for super-users who used the app more than seven minutes a day.
• Some individuals experienced 60-70% symptom decreases in that timeframe.
Leveraging early users for word-of-mouth growth[47:02]
• Guy suggests that early super-users should be Kahani's ambassadors and that growth will likely be "slow then fast" as they spread the word.
• He recommends exploring whether some users will go public and allow stories or social content to be created around their experiences.
• Mahak shares that one pilot user posted a long TikTok video about using Kahani and its impact, leading to five or six organic inbound contacts.
• She notes that the TikTok algorithm helped this spread, and she initially did not even know the video had been posted.
• She observes that younger participants may be more willing to share publicly than older, more highly engaged users.

Therapeutic basis of Kahani and Anthony's advice on scale expectations

Evidence-based methods underpinning the app[48:55]
• Mahak explains Kahani leverages evidence-based therapies such as CBT, DBT, and others validated in hundreds of clinical trials.
• They are not inventing new therapies but curating exercises and breaking them down into deeply personal, context-specific applications.
Value of small numbers and organic growth[50:26]
• Anthony praises the fact they got five inbound users from a single TikTok and encourages aiming for 10, then 20, rather than jumping to thousands.
• He is a fan of "snowball" spreading and building on the mechanisms that already caused organic growth.

Closing reflections on word-of-mouth and entrepreneurial decision-making

Word-of-mouth as the strongest marketing channel

Guy's view on recommending products[52:27]
• Guy says the best form of marketing is word of mouth, because people will only recommend products they truly believe in, especially if they are expensive or require commitment.
• He notes that authentic stories about how a tool helped someone are more powerful than any paid marketing.

Anthony's advice to his younger entrepreneurial self

Following your gut and moving faster on certain decisions[53:36]
• Guy asks Anthony what advice he would give his 22-year-old self, knowing now how Squarespace evolved from a small web tool to a major e-commerce platform.
• Anthony says the common advice is to follow your gut, and he reflects on decisions he has consistently delayed.
• He observes he often looks back and wishes he had acted faster, and almost never feels he moved too quickly on those types of decisions.
• He now tries to notice decisions where he habitually errs on the side of slowness and keep in mind that he "could have just gone faster" because he already knew what to do.

Reference to Anthony's original long-form interview and a memorable crisis moment

Guy encourages listeners to revisit the original Squarespace episode[54:10]
• Guy reiterates that Anthony's original How I Built This episode is linked in the show notes and calls it an awesome and crazy story.
Anthony's anecdote about a catastrophic server crash[55:34]
• In a clip from the original interview, Anthony recalls receiving a call from a customer asking if Squarespace was okay.
• He called the data center to reboot a server, but it did not come back, leading him to drive to New York while having a panic attack.
• He feared all the data was lost and that his "little experiment" was over.

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

If you are selling a premium or technically sophisticated product, your website and branding must immediately communicate credibility, modernity, and a clear scientific value proposition, or customers will hesitate to pay your prices.

Reflection Questions:

  • • What does my current website and packaging signal about my product's quality and sophistication to a first-time visitor?
  • • How could I rewrite or redesign my homepage and key pages so that a skeptical, analytical buyer would quickly understand why my product works and is worth the price?
  • • What specific improvements to my brand's visuals and messaging can I commit to implementing in the next 30 days to better reflect the true value of my offering?
2

Early super-users are your most powerful marketing asset; if they experience real transformation, intentionally turn them into ambassadors and storytellers rather than relying only on paid acquisition.

Reflection Questions:

  • • Who are the handful of customers or users who have gotten the most value from my product so far, and how am I currently engaging them?
  • • How might inviting one or two of these users to share their story publicly (via testimonials, case studies, or social posts) change the trajectory of my growth this year?
  • • What simple program or outreach could I launch this month to systematically identify, support, and spotlight my strongest advocates?
3

Where and when customers buy often matters more than abstract education; placing your product in high-convenience, high-need contexts (like travel, cash wraps, or post-treatment moments) can drive adoption faster than trying to change behavior in isolation.

Reflection Questions:

  • • In what specific situations are people most urgently aware of the problem my product solves (traveling, in pain, between appointments, etc.)?
  • • How could I get my product in front of customers exactly at those moments-through partnerships, placements, or new channels-rather than only expecting them to seek me out?
  • • What is one unconventional distribution context (e.g., hotels, airports, clinics) I could realistically pursue in the next quarter to test this idea?
4

For digital products, you should question assumptions about form factor: given widespread app fatigue, it may be more effective to start with the lowest-friction entry point (like the web or existing communities) and graduate users into an app only once they see value.

Reflection Questions:

  • • Am I making it harder than necessary for people to try my product by requiring an app download or account creation upfront?
  • • How could I redesign my onboarding so that someone can experience a meaningful benefit in minutes, possibly through a browser or lightweight interaction, before committing further?
  • • What existing communities, workflows, or platforms could I integrate with first so that my product feels like a natural extension of what users already do?
5

As a founder, notice the kinds of decisions you habitually delay and recognize that your intuition is often enough-moving faster on those recurring decision types can unlock significant momentum.

Reflection Questions:

  • • Looking back over the last year, which important decisions did I postpone despite having a strong gut feeling about the right direction?
  • • How might my business look different today if I had acted on those intuitions weeks or months earlier instead of waiting for more certainty?
  • • What clear criteria can I set for myself so that the next time I face a familiar decision pattern, I commit to a faster timeline instead of defaulting to delay?

Episode Summary - Notes by Parker

Advice Line with Anthony Casalena of Squarespace
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