How I Built This with Guy Raz

Advice Line with Anthony Casalena of Squarespace

Release Date: November 20, 2025
Host: Guy Raz
Guest: Anthony Casalena, Founder & CEO, Squarespace

Episode Overview

This episode of “How I Built This: Advice Line” features Anthony Casalena, the founder and longstanding CEO of Squarespace. Guy Raz and Anthony take calls from three entrepreneurs at various stages in their journeys, offering tactical, real-world advice about digital branding, omnichannel strategy, word-of-mouth growth, and leveraging early adopters. Guy and Anthony’s open, often blunt, dialogue makes for a master class on building trust, branding, and scaling a business in rapidly evolving markets.

Key Discussion Points & Insights

1. Squarespace’s Journey: Public to Private & Remaining Relevant

Timestamps: 03:33–09:48

• Anthony’s Role and Company Evolution:
  Anthony recaps Squarespace’s journey, from its scrappy origins to IPO, to being acquired by private equity and going private again—all while retaining his role as CEO.
  • “Running a company, you always have a boss, be it… Even if you owned 100% of it yourself, your customers would be your boss.” – Anthony, 05:10
• Expansion & Suite of Tools:
  Explains how Squarespace has evolved from a website builder for DIYers into a multi-faceted platform for online businesses (sites, blogs, e-commerce, scheduling, domain registration).
  • “What we do is more relevant than ever because this is how normal people participate in the web… we continue to do very well and it’s just kind of a pleasure to be servicing millions of entrepreneurs.” – Anthony, 07:00
• AI’s Influence on the Web & Web Presence:
  Anthony addresses how the rise of AI search/answer engines like ChatGPT and Perplexity impacts the role of the small business website, arguing websites are now even more crucial as the data source for AI and as the hub for real customer interactions.
  • “The website ends up being more relevant than ever… it's being used in both their index and… real-time interactions.” – Anthony, 07:42
  • On AI integration at Squarespace: “Our blueprint AI product… was named one of Times 100 Best Inventions of the year just last week.” – Anthony, 09:23

2. Advice Call #1: Custom Sleep Technology (Custom Mattress Startup)

Caller: Bob Zukowski, Newtown, CT
Timestamps: 10:12–20:03

• Business Model:
  CST uses AI to design custom latex mattresses tailored to individual body profiles, priced at $3,800–$4,500.
• Main Challenge:
  Emerging brand not suited to traditional retail; should he pursue partnerships, licensing tech to wellness/fitness companies or pro athletes to grow awareness?
• Anthony’s Blunt Website Critique:
  • “I’m just gonna go out and say the site looks a little dated… you gotta catch me with the branding or something.” – Anthony, 14:36
  • Both Guy and Anthony stress that the website is the primary salesperson for such a considered purchase; it must build trust quickly.
• Positioning – Science vs. Luxury:
  • “I am a little skeptical when the materials are like… horse hair and… horses from here… why does that make a better mattress? I am susceptible to what I would call more of a scientific message than a rich materials message.” – Anthony, 15:22
• Partnerships and Licensing:
  • “Maybe that’s the angle for the licensing: …if you want something custom… you could be the technology behind that… help them out without having to go from zero and build a brand from zero.” – Anthony, 18:04
• Key Insights:
  • Modernize digital presence immediately—customers won't call or meet you.
  • Lean into the brand’s “custom science” uniqueness—not generic luxury.
  • Partnerships with data-driven wellness tech brands (e.g., Oura, Whoop, Eight Sleep) could be a path to scale.

3. Advice Call #2: All Better Company (Reimagined First Aid Kits)

Caller: Stacey Bernstein, Los Angeles, CA
Timestamps: 24:49–38:12

• Business Model:
  All Better creates “clean beauty”-grade first-aid essentials (like an OTC hydrocortisone replacement), with sustainability and skin sensitivity as differentiators.
• Main Challenge:
  Competing against legacy first aid brands with established trust—how to persuade consumers to rethink essentials like Band-Aid or Neosporin when the category is “not sexy” and education is tough?
• Channel Discussion:
  • Hey, do we double down on DTC, Amazon, or focus on mass retail?
    • Guy: Omnichannel is critical; DTC is noisy, but retail is expensive. Try travel outlets, airports, convenience for impulse/buy-on-need.
  • Anthony’s Travel/Hotel Placement Tip: “I have recently discovered a couple of brands…put in the rooms. I became a big buyer… it’s related to travel.” – 30:33
• Messaging & Packaging:
  • Guy emphasizes that quick, clear on-package education is vital at point of purchase.
    • “Educating people about that’s going to take a lot of time… focus on getting it into as many places as possible where people make convenience purchases.” – Guy, 34:22
  • Both suggest mimicking food macro labeling: “Take what you see in food with 7 grams of protein, 10 grams of fiber, and apply that to what you’re doing.” – Guy, 37:57
• Brand Positioning:
  • “Is it a convenience purchase, is it an impulse? …Your branding lends itself to not being like a sterile medical purchase.” – Anthony, 35:12
• Key Insights:
  • Placement (hotels, airports, impulse locations) can build trial and trust.
  • On-pack education (“plant-based,” “chemical-free,” “safe for sensitive skin”) must be fast and clear.
  • Lean into branding that sets it apart from legacy “clinical/sterile” first aid.

4. Advice Call #3: Kahani (Eating Disorder Recovery App)

Caller: Mahak Mohan, New York City
Timestamps: 40:22–51:37

• Business Model:
  Kahani is a personalized app that uses evidence-based psychological therapies (CBT, DBT, etc.) to assist recovery from eating disorders; launching soon on the App Store as a subscription.
• Main Challenge:
  Standing out for launch; how to get initial traction and maximize launch impact in a saturated app market?
• Anthony’s Insight on App Fatigue:
  • “There’s millions of apps… there’s also a fatigue related to apps. It's kind of a lot for me to install a new app. …Imagine it wasn’t even an app, where do I find it and does it need to be an app?” – 43:08
• Leverage Early User Ambassadors:
  Guy & Anthony strongly recommend building from word-of-mouth, since marketing dollars are limited.
  • “If you're saying, hey, 23% decrease or better outcomes, those are your ambassadors… can you incentivize them?” – Guy, 46:56
• Authentic Storytelling:
  • “Some combination of… vulnerable stories that can relate to people authentically and maybe spread virally is, I think, great.” – Anthony, 50:55
  • Both note that unlike mass-market products, trust and authentic testimonials from real users (including on TikTok) are the most credible marketing for Kahani’s sensitive target population.
• Key Insights:
  • Focus on “psychographics,” not just demographics—find highly motivated users in moments of life transition.
  • Let super-users become evangelists; nurture, incentivize, even create small private community channels for them.
  • Authentic storytelling (user videos, testimonials) can be more potent than broad ad campaigns.

Notable Quotes & Memorable Moments

• Anthony on always having a “boss” as a founder:

  “Even if you owned 100% [of the company] yourself, your customers would be your boss.” – Anthony, 05:10

• Anthony’s advice on branding and digital presence:

  “Your website’s what’s talking to people… You need to basically make it so people can say, yeah, I’ll do that.” – Anthony, 16:36

• Brand-positioning insight:

  “I am susceptible to what I would call more of a scientific message than a rich materials message.” – Anthony, 15:22

• On moving faster as a founder:

  “I would look back and go, what decisions do I always delay on? And I’m always looking back and going, I wish I had done that faster. …Why does it always err in one direction?” – Anthony, 53:11

• On organic, snowball marketing for apps:

  “You were like, we got five [users via TikTok]. That’s amazing. If you can get 10, then you can get 20. …I’m a big fan of that sort of snowball spreading and you encouraging the mechanisms of why it has spread.” – Anthony, 51:00

• Guy connecting omnichannel to branding:

  “Focus on getting [the product] into as many places as possible where people make convenience purchases.” – Guy, 34:22

Important Timestamps by Segment

| Segment | Timestamp | Highlights | |--------------------------|----------------------|--------------------------------------------------| | Squarespace’s Journey | 03:33–09:48 | IPO, going private, AI, company relevance | | Custom Sleep Tech Call | 10:12–20:03 | Digital trust, scientific messaging, partnerships| | All Better Co. Call | 24:49–38:12 | Omnichannel, on-pack comms, travel retail | | Kahani App Call | 40:22–51:37 | Word-of-mouth, user ambassador strategy | | Anthony’s Final Advice | 53:11–54:01 | Move faster, trust your gut |

Key Takeaways

• For founders, brand trust is built or lost instantly online; your website and packaging must tell your story, clearly and fast.
• Scientific messaging and authenticity often trump luxury signaling, especially in crowded or credibility-driven categories.
• Big, established channels are hard to disrupt—creative placement (hotels, airports, communities) and omni-channel can unlock attention.
• Startups with limited marketing budgets must convert early adopters to evangelists and build momentum via authentic storytelling and word-of-mouth.
• As a founder, learn to spot recurring points of indecision, and push yourself to act faster in addressing them.

This rich, transparent episode demonstrates how entrepreneurial strategy, digital branding, and customer-centricity can unlock growth for any stage of business — from the kitchen table to the App Store.