Ross Williams

Ross is a multi-award winning serial entrepreneur | Built a $50m Subscription Business (Bootstrapped & Battle-Tested) | Growth Strategist | Churn Slayer | Helping You Scale Without the War Wounds

Success and Failures of 25+ years of entrepreneurship

I built a $50M SaaS empire—$8million EBITDA, nearly 200 staff, all bootstrapped with zero external funding. Now, I’m rethinking success, determined to do things differently and share my hard-won lessons. Subscribe below and follow my journey for candid insights, resilience, and real-world strategies:

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How we fell out of love 💔 with dating apps

Dating apps’ honeymoon is over. Users—especially women and Gen Z—are burned out, switching to niche sites and offline events. Match and Bumble face sliding valuations, churn and tougher rivals. AI tweaks won’t restore trust; authenticity wins, meaning big incumbents likely shrink.