🎙️ New Ep. Allen Naliath | Sam Altman + Garry Tan Cold Asks, Win Conditions You Control & Why Friday Stops at 99%

Hey There,

👉 SGP Ep. 28 | Allen Naliath is the Founder and CEO of Friday, a Chrome extension that integrates AI email management directly into Gmail. Two years ago at Stanford, he struggled with the confidence to ask for what he wanted. So he engineered a solution: a 30-day rejection challenge where he had to hear "no" once per day or start to ask for increasingly audacious requests. The problem: people kept saying yes.

He escalated strategically—waiting by a golf cart to ask Sam Altman to sign his laptop, and cold-asking Garry Tan to add him on LinkedIn during a Stanford talk. Garry's response: "Is this a Psyop?" He added him anyway. That connection led to YC.

Today, Friday processes emails via predicted action buttons—users press enter repeatedly to archive, reply, or unsubscribe. Allen personally onboards every user to inbox zero in 10 minutes, even with 18,000 unread emails.

Naliath's catalyst was advice from a founder mentor: "If you want to work on startups when you graduate, don't even apply to Apple and Google. If you have no plan B, plan A has to work." His core insight: most people's win condition depends on the other person saying yes. He reframed it so yes and no are both wins—the win condition is in his control just by asking.

That philosophy runs through Friday's design: it doesn't put email on full autopilot (which "induces anxiety"), it gets users 99% of the way. Friday started as a hackathon project, evolved into a mobile text assistant, then became a Chrome extension after realizing Gmail integration was faster than building feature parity. The average person spends two hours per day in email; Friday users get through 30 emails in 60 seconds.

Key Topics Covered:

• Win condition reframe: "Yes and no are both wins. The win condition is in my control just by asking."

• Cold approaches: Sam Altman golf cart ambush, Garry Tan LinkedIn add during Stanford talk

• Anti-autopilot philosophy: "That induces anxiety. It gets you to 99%—you stay in control."

• Predicted action buttons: archive, reply, unsubscribe—all one-keystroke approvals

• & much more

I hope you find this educational content valuable and can apply it in your business. Until next week - keep experimenting, keep scaling, keep building.

David J Phillips

Founder & CEO at Fondo

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