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Ross Williams Profile image
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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Generative Romance? AI’s Fast-Growing Role in Dating Apps Could Destory the Entire Industry Forever Post feature image

Generative Romance? AI’s Fast-Growing Role in Dating Apps Could Destory the Entire Industry Forever

The online dating industry is committing an Ouroborosian display of self immolation through it's adoption of generative AI.

5 min read
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Visa VAMP 2025: Survival Guide for Dating & Subscription Merchants – how to still have a business by 2026 Post feature image

Visa VAMP 2025: Survival Guide for Dating & Subscription Merchants – how to still have a business by 2026

The Ultimate Guide to Survive Visa & Mastercard’s 2025 VAMP Era - Online dating, coaching, digital content – this is for you.

4 min read
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Why Swiping Right on AI Is Like Bringing a Blender to a First Date Post feature image

Why Swiping Right on AI Is Like Bringing a Blender to a First Date

Dating apps flirting with full-blown AI is like bringing a blender to a first date—loud, confusing, and nobody’s actually craving a smoothie. Real chemistry happens in coffee shops and speed-dating rooms where you can’t hide behind airbrushed selfies or ChatGPT pickup lines.

2 min read
The $Million Fight Against Loneliness: How Apps Are Turning Strangers into Friends IRL Post feature image

The $Million Fight Against Loneliness: How Apps Are Turning Strangers into Friends IRL

Investors are pouring millions into friendship apps like 222 and Pie, betting that tech-facilitated real-life connections can help solve the modern loneliness epidemic.

3 min read
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