In this episode of Built with AI, we discuss building with AI when the hard part is defining success, checking the output, and improving the system.
The discussion covers the shift from code as a technical barrier to prompting through a command line. We look at building data syncs, apps, documents, and workflows with AI while keeping a clear finish line.
We also discuss model choice and usage pricing. Faster modes can buy time at a premium, but the newest model is not always the best model for the work.
A major theme is self-healing and self-improving automation. We discuss outreach systems, email subject lines, send times, creative blocks, rate limits, and how each step should contribute to the final outcome.
The conversation covers hill climbing as a way to optimize. Early signals may be opens, then clicks, add-to-cart events, and conversions. Optimizing one metric in isolation can create misleading results, damage the brand, or produce low-value customers.
We discuss connecting data across commerce, marketing, subscription, customer, and finance systems. Programmatic bookkeeping can remove repetitive work, but payment and account-receivable workflows still need reliable checks.
The discussion also covers the limits of AI-generated creative work. AI can produce several technically good options, but human taste and domain judgment still matter when choosing website copy, headlines, and user experiences.
We close with team adoption. The approach discussed is to lead by example, look for agency and curiosity, automate workflows through natural attrition, and make people responsible for what they send even when AI generated it.
Chapters
00:00 Live sheet syncs for a brand
01:04 Buying time at a premium
03:01 Command-line prompting
03:45 The outreach machine and its rate limits
08:43 Where's the finish line?
13:02 Self-healing loops
15:10 Open rate is a trap
18:01 LTV, profit, and rebills
21:35 How the models feel to use
26:41 CLI trade-offs and the max plan
36:02 Technically good still needs taste
38:31 Names people get excited about
42:40 Creators and human leverage
46:10 Attrition and productivity
50:11 Demo: the ad launcher
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