What happens when a young lawyer realizes that adult friendships are slowly fizzling out because time becomes a luxury? Neil Tanna found himself watching his social connections fade as the demands of professional life took over, and instead of accepting this as inevitable, he decided to build a solution.

As CEO and co-founder of Howbout, Neil has created something that's resonating powerfully with Gen Z – a social calendar app that's attracted 5 million users in just five years. Unlike traditional social media platforms that have become entertainment feeds filled with strangers and brands, Howbout brings the focus back to what really matters: your actual friends and the time you spend together. Neil's journey from frustrated lawyer to startup founder offers a fascinating look at how one person's personal pain point became a platform that's changing how an entire generation maintains their friendships.

“We have lowered the barrier of entry to maintaining friendships, which is why our platform is so powerful and it doesn't need to be performative.” – Neil Tanna

In this episode, you will:

• Learn how Neil identified the "Chief Friendship Officer" persona in every friend group and used this insight to solve the cold start problem that kills most social apps
• Discover why Gen Z is surprisingly comfortable sharing their private calendars with close friends, despite older generations' concerns about privacy
• Understand the clever growth hack involving Instagram meme pages that helped Howbout acquire their first 1,000 users without traditional advertising
• Explore how calendar data from 100 million user entries is being used to understand what Gen Z actually does with their time, from date night debriefs to Sunday planning sessions
• Uncover why Howbout's retention rates doubled after shifting focus from utility-first planning to social-first engagement, and what this means for the future of friendship apps

Neil's story challenges the assumption that successful social platforms need to be entertainment-focused or rely on performative content. Instead, Howbout proves that authenticity and genuine connection – even in small, private networks of 5-15 close friends – can drive massive engagement and growth. With ambitious plans to reach 40 million users by 2026, Neil's approach to building "a world where friendships never go on pause" offers valuable lessons for anyone interested in consumer social products and the evolving nature of digital relationships.

Tune in to hear how one lawyer's frustration with fading friendships became a social calendar revolution that's redefining how young people stay connected.

Connect with Neil:

• LinkedIn

Connect with Matt:

• LinkedIn
• Curious Customer Website

As the Founding Designer of Lovable, Nad Chishtie isn’t just building another web tool—he’s helping reimagine who gets to build software in the first place. With a mission to flip the 1% of people who can code into the 99% who can create, Lovable is already turning heads with its impressive $60M run rate in under a year. Nad brings years of product and design thinking to the table, but it’s his ability to blend deep technical abstraction with intuitive simplicity that truly sets him apart. In this episode, Nad opens up about the bold thinking behind Lovable, why friction isn’t always a bad thing in user experience, and how AI can be your toughest design critic—or your best creative partner.

“The way that we see things is that today less than 1% of the planet can create, deploy, and maintain full stack applications.” — Nad Chishtie

In this episode, you will:

• Learn why Lovable chose to build for a broad audience first—before narrowing in on specific user types.
• Discover how early user reactions helped shape key design decisions and why emotional responses like empowerment and speed became the team’s guiding compass.
• Understand how Nad uses AI not just to design faster but to think better—leveraging GPT as a critique board rather than a shortcut tool.
• Explore why the team has intentionally avoided complex onboarding and stuck with a simple chat interface to build anything.
• Hear how real users—from indie founders to romantic partners—are using Lovable to create everything from SaaS businesses to marriage proposals.

Tune in to hear how Nad and the team behind one of Europe’s fastest-growing startups are rethinking what it means to design, build, and launch in the age of AI. Whether you're a designer, founder, or just curious about the future of digital creation—this one’s worth a listen.

Connect with Nad:

• LinkedIn

Connect with Matt:

• LinkedIn
• Curious Customer Website

As the Senior Director of Marketing at LEGO, Madelaine Edwards carries a huge legacy on her shoulders - and does so with clarity and purpose. In this episode of Curious Customer, she joins Matt to share how a 90-year-old brand continues to evolve without losing sight of its origins. Starting from a small Danish carpenter’s workshop in 1932, LEGO has become one of the world’s most recognized and loved brands. But it’s not just about bricks anymore. Madelaine explains how the company’s approach to creativity, play, and innovation keeps LEGO relevant for kids, adults, and families across generations. From navigating shifts in digital entertainment to pushing for sustainability, Madelaine offers a behind-the-scenes look at how LEGO stays playful while building for the future.

”Our hope as a company is that through Lego Play, and through building and rebuilding, it becomes a bedrock for creative confidence and courage and self-belief.” — Madelaine Edwards

In this episode, you will:

• Learn how LEGO balances its timeless core product with constant innovation, releasing over 800 new sets each year.
• Discover how LEGO collaborates with global brands like Nike, Fortnite, and Formula 1 to stay relevant to today’s younger audiences.
• Understand the importance of marketing in shaping both consumer perception and product development—especially when engaging different audiences like girls and adult fans.
• Explore how LEGO is tackling sustainability, including using recycled materials in products like tyres made from old fishing nets and engine oil.
• Hear what Madelaine thinks LEGO will look like ten years from now, and why physical play still matters in a digital world.

Tune in to hear how a classic brand stays fresh without losing its sense of play.

Connect with Madelaine:

• LinkedIn

Connect with Matt:

• LinkedIn
• Curious Customer Website