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Ever wonder why “I can build it in a weekend” becomes months of maintenance debt? We sit down with TypeSense CEO Jason Bosco.We get honest about developer psychology. Yes, you can build it—but not the years of nuance: typotolerance, geo search, semantic relevance, faceting, and the thousand edge cases you only learn from a large, vocal user base. We talk through when it’s smart to build (their custom observability agent for cost and resource constraints) and when buying is the rational choice. The rule of thumb: tie every build decision to a clear customer benefit, not ego or the thrill of coding.Pricing myths take center stage. The $1 app era and VC-subsidized SaaS taught us to expect “free,” until it disappears or goes enterprise. Jason argues for honest unit economics: no free hosted tier that hides real costs, and a revenue model that survives contact with reality. We also dig into funding: why VC can be great for moonshots but misaligned for dev tools that need decades of stabilit

Join us for the San Francisco Ruby Conference 2025: Building the Future with Ruby. November 19-20 at Fort Mason, San Francisco.