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  1. How I Built This with Guy Raz
  2. Advice Line with Anthony Casalena of Squarespace
Advice Line with Anthony Casalena of Squarespace

Advice Line with Anthony Casalena of Squarespace

How I Built This with Guy Raz · Nov 20, 2025

Squarespace founder Anthony Casalena advises startups on branding, omnichannel strategy, and authentic marketing for niche products.

Even with 100% Ownership, Your Customers Are Your Boss

A founder is never truly without a boss. If not shareholders or a board, the customers ultimately dictate the company's direction and success. This mindset ensures a customer-centric approach regardless of ownership structure, keeping the business grounded and responsive to market needs.

Advice Line with Anthony Casalena of Squarespace thumbnail

Advice Line with Anthony Casalena of Squarespace

How I Built This with Guy Raz·3 months ago

Prioritize Scientific Efficacy Over 'Rich Materials' in Premium Branding

For sophisticated consumers, branding based on unsubstantiated luxury materials can create skepticism. A marketing message focused on scientific proof, tangible benefits, and performance can be more compelling and build greater trust, especially for a high-price-point product.

Advice Line with Anthony Casalena of Squarespace thumbnail

Advice Line with Anthony Casalena of Squarespace

How I Built This with Guy Raz·3 months ago

Target Users by Psychographics, Not Just Demographics

For specialized products, user motivation is more critical than age or location. Focusing on the user's mindset, life stage, and readiness for change (psychographics) can lead to significantly higher engagement and retention than targeting a broad demographic group that may not be ready for the solution.

Advice Line with Anthony Casalena of Squarespace thumbnail

Advice Line with Anthony Casalena of Squarespace

How I Built This with Guy Raz·3 months ago

Your Website is the Source of Truth for AI Answer Engines

In an era dominated by AI chatbots, a website's relevance increases. These AI systems don't create information; they crawl the web to find it. Your site serves as the foundational data source, making a well-structured, up-to-date digital presence critical for discoverability and accurate representation by AI.

Advice Line with Anthony Casalena of Squarespace thumbnail

Advice Line with Anthony Casalena of Squarespace

How I Built This with Guy Raz·3 months ago

Use Hotel Partnerships for Premium, High-Context Product Sampling

Placing products in hotel rooms serves as a 'non-cheesy free sample.' It's a high-context discovery channel where consumers experience the brand as a curated part of a premium travel experience. This creates a strong positive association and drives adoption more effectively than traditional sampling.

Advice Line with Anthony Casalena of Squarespace thumbnail

Advice Line with Anthony Casalena of Squarespace

How I Built This with Guy Raz·3 months ago

License Your Core Technology to Bypass Brand-Building Hurdles

Instead of building a consumer brand from scratch, a technologically innovative but unknown company can license its core tech to an established player. This go-to-market strategy leverages the partner's brand equity and distribution to reach customers faster and validate the technology without massive marketing spend.

Advice Line with Anthony Casalena of Squarespace thumbnail

Advice Line with Anthony Casalena of Squarespace

How I Built This with Guy Raz·3 months ago

Apply Food-Style 'Macro' Labeling to Non-Food CPG Products

Consumers are trained by food packaging to look for simple, bold 'macros' (e.g., '7g Protein,' 'Gluten-Free'). Applying this concept to non-food items by clearly stating key attributes ('Chemical-Free,' 'Plant-Based') on the packaging can rapidly educate consumers at the point of purchase and differentiate the product.

Advice Line with Anthony Casalena of Squarespace thumbnail

Advice Line with Anthony Casalena of Squarespace

How I Built This with Guy Raz·3 months ago

Decisions You Delay Are the Ones You Should Have Made Faster

A founder's retrospective analysis often reveals that delayed decisions were the correct ones, and the only regret is not acting sooner. Recognizing this pattern—that you rarely regret moving too fast—can serve as a powerful heuristic to trust your gut and accelerate decision-making, as inaction is often the biggest risk.

Advice Line with Anthony Casalena of Squarespace thumbnail

Advice Line with Anthony Casalena of Squarespace

How I Built This with Guy Raz·3 months ago