Why keep multiple ventures active

Jesse explains diversification, creative variety, and risk mitigation for running many projects.

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Episode notes

In this episode, Chris Do sits down with designer, publisher, and entrepreneur Jesse Reed to explore the intersection of design systems, business, and long-term creative impact. Jesse shares his journey from Pentagram to co-founding multiple ventures, including Standards Manual, Order, and Standards, and explains how each evolved from curiosity-driven projects into sustainable businesses. The conversation highlights the importance of focus, simplicity, and decision-making in both design and entrepreneurship, especially when building systems meant to scale across teams and industries. Throughout the discussion, Jesse emphasizes that timeless design principles—typography, structure, consistency—remain unchanged even as tools and platforms evolve.

Timestamps

(00:00) — Intro

(06:45) — Founding Standards Manual

(13:30) — Crowdfunding lessons learned

(20:10) — Balancing multiple companies

(27:05) — Focus versus simplicity

(33:50) — Business models in design

(40:20) — Brand guidelines evolution

(46:55) — Emotional branding shift

(53:30) — Rebrand backlash explained

(01:00:05) — Criticism and creative success

(01:06:10) — Collaboration over competition