Why market research beats intuition in vertical SaaS with Adam Flemming

January 20, 2026
The Payments Strategy Show

Diving into a brand new market without any deep knowledge or industry research is how many kick off their entrepreneurial journeys. 

After five startups, Adam Flemming took a different approach when he founded self-storage platform Cubby – he looked before he jumped. The result? A company built on deep market research that treats payments as a core necessity and goes beyond addressing just the symptoms of customer issues. 

In this episode, Cubby’s Founder, Adam Flemming joined host Becky Kopplin to share hard-won lessons on building a successful vertical SaaS company the right way. 

They discussed: 

  • Why researching the market before launching a company is critical – don't jump into the pool without knowing the depth
  • The critical reason vertical SaaS leaders must treat payments as a core product feature, not an afterthought 
  • How AI’s biggest value is to eliminate generic tasks so operators can focus on what differentiates their business  
  • "Simple" businesses like self-storage are more complex than they appear and require sophisticated software
  • Why digging deep to the root cause of customer problems is better than just providing surface-level support

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