Gumroad's Structure: Small Team, Contractors, Open Source

Today’s Episode

Sam Altman said one person will build a billion-dollar company.

Sahil’s already halfway there with just one employee.

Most PMs are still running 6-week sprints. Writing 10-page PRDs. Coordinating between designers and engineers. Sahil ships features from Slack to production in 30 minutes.

Here’s the exact AI workflow powering Gumroad’s $10M ARR:

If AI gets it wrong, your communication was unclear.

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Key Takeaways

1. Three-Tier AI Workflow: Small tasks (Slack → Devon → Production), Medium tasks (GitHub issue → GPT for PRD → V0 prototype → Ship), Large tasks (4-line brief → V0/Codex → Vercel → Cursor → Production). Match the tool to task complexity.

2. From Slack to Production in Minutes: Customer reports feature request in Slack with screenshots. Type "Devon, address this." Devon reads thread, writes code, opens PR, ships to production. "Weeks of coordination at big companies. We just decide and Devon addresses it."

3. The PRD Is Dying: Stop writing 20-page PRDs for AI. Write 4 lines. Let AI prototype. See what it misunderstands. That reveals what you forgot to specify. "The PRD is only as dense as what cannot be inferred naturally."

4. Use AI to Refine Your Thinking: Paste brief into V0, GPT, and Codex. Each builds something different. Their mistakes show your communication gaps. It's a fake conversation with engineers that makes your real spec better.

5. Architecture Is the New Competitive Advantage: Gumroad is deleting 5,425 lines of CSS to migrate to Tailwind (181 lines). Global CSS means every change affects 300 files. Tailwind means one file change. "Devon made a one-file change. With CSS, you're testing 300 files."

6. Tailwind Is Built for AI: Design system in 181 lines: fonts, colors, padding, borders, shadows. AI never guesses. Industry standard with massive training data. "It's like hiring an engineer who already understands 2x4s. AI knows exactly what to do."

7. AI Is 99th Percentile at Most Things: Defer design and code decisions to AI. If it's important, put it in the spec. If not in the spec, let AI decide. "The decisions AI makes are pretty good. That's why we can move super fast."

8. Work on 5 Things Simultaneously: AI is slow. Solution? Run 4-5 AI sessions at once. While V0 builds, check email. While Codex compiles, answer Slack. "It's like having an army of assistants. I don't wait—I fill the dead time."

9. The Dictatorship Advantage: Big companies need buy-in from PMs, designers, engineers, managers. Gumroad: Sahil → Devon → Production. "The hard part at big companies is aligning people to get behind a decision. It has nothing to do with actually shipping."

10. Perfect the Business, Don't Scale It: $10M ARR, $7-8M EBITDA, $2M dividends last year, 1 employee, 35,000 creators. Goal: $10M EBITDA, then perfect the software. "I just want to work on software, make it better, have people use it, be proud of the work we do."

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Where to Find Sahil Lavingia

* Linkedin

* X (Twitter)

* Gumroad

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