Toast: Aman Narang. How a Long Wait for the Dinner Check Launched a $2 Billion Business.

After waiting too long to pay his restaurant bill, Aman Narang thought there had to be a better way. His first idea—a mobile payment app—flopped.

But that failure revealed a much bigger opportunity.

Restaurants were struggling with outdated software that many owners hated. Payment systems were expensive, unreliable, and trapped on servers hidden in back offices. Replacing them cost time and money.

But that’s exactly what Aman and his co-founders set out to do: create an entirely new POS system for restaurants—from scratch.

They worked from an unfinished basement, answered customer calls on their own phones, crashed their first restaurant on day one, survived years of rejection from investors—and eventually grew Toast into a business that generates more than $2 billion in annual revenue.

In this episode, Aman shares how a failed product became a billion-dollar company.

What you'll learn:

• How to know when it's time to pivot
• Why investors rejected Toast again and again
• How to convince customers to replace mission-critical software
• Why Toast intentionally stayed small before scaling
• The leadership lesson Aman learned after almost breaking the company
• How Toast survived COVID after restaurants shut down
• What founders should look for when choosing a co-founder

Timestamps:

• 11:25 — The frustrating restaurant experience that inspires Toast
• 15:41 — The first product fails—and reveals a bigger opportunity
• 16:43 — Building Toast: “We grossly underappreciated what it would take.”
• 26:05 — Why nearly every investor said “No.”
• 32:31 — Toast’s disastrous first launch: writing credit card numbers by hand
• 34:18 — Pitching hundreds of restaurant owners before finding believers
• 38:08 — Why customer obsession beats competitor obsession
• 44:17 — Bringing in a new CEO: “We need to rethink how we do things here.”
• 52:31 — The biggest lessons from building a $2 billion company

This episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by Neva Grant with research help from Casey Herman. Our engineer was Kwesi Lee.

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