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