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September 25, 2025 โ€ข 50 mins
Richard Hollingsworth bootstrapped an executive assistant agency to $5M ARR, then pivoted to AI and grew from $1M to $18M ARR in just 8 months. Today, Fyxer serves thousands of professionals with their AI email assistant, and Richard's team has grown from 4 to 40 employees while raising over $40M. Richard and his brother Archie started with data from their EA agency, waited for the right technology moment with GPT-3, then moved to San Francisco to scale. Their focus on professional services over tech companies, combined with a land-and-expand strategy, helped them close a $1.2M deal in 7 days and build a thriving AI SaaS business. You'll learn: How to turn an agency into an AI SaaS company using existing customer data and insights Why targeting professional services instead of tech companies unlocked massive growth opportunities How a land-and-expand sales motion helped convert single users into a 5,000-seat enterprise deal worth $1.2M What mistakes nearly destroyed their customer success during hypergrowth and how they recovered How to maintain culture and intensity while scaling from 4 to 40 employees in under a year Full show notes โ†’ saasclub.io/454 This episode is brought to you by: ๐Ÿ’– Gearheart โ†’ Book a free strategy session + get 20% off select services Get weekly SaaS lessons and new founder stories โ†’ saasclub.io/email
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