Failed Software Startup: 10 Products Before PMF

Jeb Banner built almost a dozen products that went nowhere over 12 years. His failed software startup streak broke only when he separated product from his agency and found product-market fit targeting nonprofits.

Learn why a failed software startup inside an agency never survives, how Boardable achieved product-market fit by targeting nonprofit boards, and what hidden conversion signals a data scientist uncovered.

Jeb is the CEO of Boardable, a board management platform. After 10 failed software startup attempts as part of his agency to SaaS journey, Boardable reached 7-figure ARR with 2,000 customers in 40 countries.

🔑 Key Lessons

• 📉 A failed software startup inside an agency can't compete for attention: Jeb built 10 products over 12 years - the pattern broke when Boardable became a separate entity.
• 🎯 Target acute pain to prevent another failed software startup: Nonprofits with 50 board members and one admin felt pain far more than for-profits, enabling product-market fit.
• 🛠️ Build for complexity, then sell simplicity: Solving nonprofit complexity first created an advantage when expanding - a finding product-market fit lesson.
• 🤝 Recognize when product-led growth breaks down: Boardable's PLG stalled in the agency to SaaS transition because the user was not the buyer.
• 🧠 Data science finds hidden conversion signals no failed software startup expects: Deleting an agenda item in a trial predicted conversion better than any firmographic data.

Chapters

• Introduction
• What Boardable does
• Business size, revenue, and funding
• How a client request sparked the idea
• Why nonprofits for finding product-market fit
• Building the MVP
• Using Capterra for growth
• Product-led growth to sales transition
• Lead scoring with a data scientist
• The agenda deletion conversion signal
• The failed software startup pattern over 12 years
• Separating product from agency to SaaS
• Why Boardable finally achieved product-market fit
• Competitive landscape
• Lightning round

Resources

• Full show notes: https://saasclub.io/312
• Join 5,000+ SaaS founders: https://saasclub.io/email