Dive Club 🤿 Brandon Jacoby - Seeing Taste vs. Creating Taste as a designer
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Apr 21, 2026 
Brandon Jacoby, product and design leader who helped shape Cash App, Capital, and X, now running an independent practice. He talks about taste as a learned skill, how to spot versus create great design, using AI to build bespoke design tools, thriving in 0→1 environments, and practical lessons on onboarding, mentorship, and selling beyond “good enough.”
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Build Custom AI Tools To Accelerate Work
- Use AI to build bespoke design tools and agents that fill gaps in your workflow instead of only using off-the-shelf features.
- Brandon prompts Claude to solve technical blocks and automates repetitive tasks to keep creative momentum.
Amplification Favors Builders Not Bystanders
- Designers who 'run through walls'—question requirements and invent or build missing tech—gain the biggest amplification from AI.
- Those who externalized blockers before may not be automatically empowered by AI without initiative.
Taste As The New Competitive Edge
- Taste is rising as a core differentiator because abundance makes 'good enough' ubiquitous; taste guides choices beyond technical parity.
- Taste can be learned and trained but often requires environment and repeated exposure to diverse creative stimuli.