Jason Cohen

How this $1M bootstrapped SaaS can expand into a new market. | Smart Bear Live 002

Aug 16, 2026 · 2:14:17

Jesse Schoberg's DropInBlog has 2,000 customers, 2% monthly churn, and a plateaued growth curve; hosts Jason Cohen and Rob Walling argue DropInBlog should deliberately push into BigCommerce businesses and agencies serving them. Schoberg says enterprise visitors were 5% of traffic but converting zero; after adding invoicing, audit logs, and white-glove migrations, $399/$499 plans began selling. They tell him to market engineers and marketers separately, pitch marketers on AI/LLM visibility as job security, use ads to learn messaging not just ROI, and build an agency channel because one agency can bring multiple clients. They also challenge his Laravel focus, argue BigCommerce is where the fish are, and advise giving each initiative an owner, separate metrics, and company-wide alignment.

This SaaS founder showed me every metric. It's not good... but we fixed it

Jul 21, 2026 · 2:04:49

Jason Cohen and Dmytro Krasun dissect Dmytro's SaaS ScreenshotOne ($32K MRR, 9% monthly churn, flat growth) and find a structural ceiling around $40K MRR—9% churn on a growing base cancels new revenue. The crux: after four years and thousands of customers, no single large, repeatable market for screenshots-as-an-API has emerged. They lay out four honest options: incremental improvement to push $40–50K MRR; building a different product (e.g., regression testing for marketers) leveraging screenshot expertise; selling the business; or pivoting to AI integrations (MCP server, CLI, SDKs) to get embedded in AI workflows. Dmytro commits to a month of intensive exploration of the AI path, running the business on skeleton mode, to determine if this can restart growth or if he should sell.