In this episode, we sit down with Songe LaRon, the visionary co-founder and CEO of Squire, the world’s leading barbershop management and fintech platform. What began as a frustrating experience trying to book haircuts during his time as a corporate lawyer turned into a multi-national SaaS business now powering over 20,000+ barbers across the US, UK, Canada, and Australia.
After graduating from Yale and launching his career in M&A law, Songe left behind the security of the corporate world to solve a problem nobody else was looking at. Alongside his co-founder, he built Squire from the ground up—bootstrapping early growth, running their own barbershop to understand the customer, and eventually raising $165 million in venture capital.
Today, Squire is not just a booking tool—it’s a fully integrated operating system and fintech engine helping barbershops run more efficiently, grow faster, and stay financially empowered.
But behind the product is a deeper story—one about bold pivots, overcoming rejection, and why customer obsession is still the most powerful growth strategy in business.
We cover:
- How solving his own pain led to a billion-dollar opportunity
- The leap from Yale Law to barbershop entrepreneurship
- The brutal Series A journey: 59 rejections and 1 life-changing “yes”
- Why every founder needs to live inside their customer’s world
If you’re building a vertical SaaS company—or chasing an opportunity in an overlooked market—Songe’s story is a playbook in grit, intuition, and scale.
// LINKS //
Instagram https://www.instagram.com/jeromedwightx
YouTube https://www.youtube.com/@jeromedwightx
TikTok https://www.tiktok.com/@jerome.dwight
Spotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw&nd=1&dlsi=1ae5fe7561434a39
#challengerx #jeromedwight #songelaron #squire #fintech #startuplife #founderstory #barbershoptech #verticalsaas #entrepreneurship #customerobsession #startuplessons #scalingtech #ycombinator #growthmindset #blackfounders #ceomindset #leadership #buildinpublic #startupgrind
