The Bootstrapped Founder 425: AI Best Practices for Bootstrappers (That Actually Save You Money)
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Nov 28, 2025 Discover how to navigate the ever-changing world of AI with insights on designing for permanent migratability. Learn to run old and new prompts side-by-side to ensure smooth transitions, and use AI to diagnose prompt drift effectively. Explore strategies for cost optimization using OpenAI's service tiers and how to front-load data for token savings. Plus, find out about implementing safeguards like circuit breakers and rate limits to prevent runaway costs. Stay adaptable and keep your AI systems thriving!
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Build Migration-Friendly AI Services
- Extract API calls into services that handle prompts and connections so you can swap models easily.
- Run old and new prompts/models side-by-side during migration to diff outputs and roll back if needed.
Real Migration Pain From GPT-5 Rollout
- Arvid migrated from GPT-4 to GPT-5 and found prompts behaved quite differently in production.
- He ran both old and new prompts together, logged diffs, and rolled back when the new model dropped keys.
Diff Outputs And Use AI To Diagnose Changes
- Log both old and new model outputs and run automated diffs to find missing or changed keys.
- Use AI to analyze differences and suggest prompt reshapes, but validate suggestions manually.