E02: DropInBlog: How this $1M bootstrapped SaaS can expand into a new market.

DropInBlog's Jesse Schoberg has 2,000 happy customers, 2% monthly churn, a Bangkok-nomad life—and a growth curve that has plateaued. I and co-host Rob Walling tear into the real problem: a proven new cohort without a go-to-market plan. Two hours on pricing, positioning, AI/LLM visibility, the agency channel, ABM, and how to expand without breaking the business people already love.…