Richard Hollingsworth bootstrapped an executive assistant agency to $5M ARR, then pivoted to AI and grew from $1M to $18M ARR in just 9 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.

In this episode, Richard (Co-founder & CEO of Fyxer) breaks down the "Agency to SaaS" playbook. He reveals how they used six years of manual agency data to train their AI models (giving them an unfair advantage), how a "Land and Expand" strategy turned a single user into a $1.2M enterprise deal in 7 days, and the brutal reality of scaling support when your user base explodes overnight.

🔑 Key Lessons

• 💡 The Data Moat: How they used 6 years of manual agency data to train GPT-3, creating a product better than generic AI wrappers.


• 📈 Hypergrowth Reality: Scaling from $1M to $18M ARR in under a year and the specific things that broke (like support response times).


• 🏢 The $1.2M Deal: How they turned a single Facebook Ad signup into a 5,000-seat enterprise contract in just 7 days.


• 🎯 Contrarian Targeting: Why they explicitly ignore the "Tech" market to target Real Estate and Professional Services instead.


• 🧠 Culture of Intensity: The "Unreasonable Effort" mantra used to align a team during a period of extreme scaling.

📖 Chapters

• Introduction & The "Unreasonable Effort" Mantra


• Rich's Background: From Farming to Tech


• Transition to SaaS: Bootstrapping an Agency to $5M


• Early Product Lessons: Why Tech-Enabled Services Failed


• Launching the First Product with GPT-3


• Building the Team: Pitching Technical Co-Founders


• Scaling Challenges: The "Build or Talk to Customers" Rule


• Product-Market Fit: Leveraging LinkedIn Influencers


• Sales & Customer Acquisition: The Move to San Francisco


• Partnerships: The $1.2M Real Estate Deal


• Key SaaS Metrics: Moving from Single Player to Multiplayer


• Tough Lessons: When Support Broke During Hypergrowth


• Company Culture: Hiring for Intensity


• SaaS Trends: AI Agents & Future of Work


• Lightning Round

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Resources:

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