How I Built This with Guy Raz
How I Built This with Guy Raz

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

July 20, 2026

AI Summary

5 min read

Aman Narang did not set out to build a restaurant operating system. In 2012, he and his co-founders Steve Fredette and John Grimm wanted to solve a much narrower problem: the annoying wait for the dinner check. They built a mobile payment app, convinced the owner of a Cambridge bar called Firebrand Saints to let them test it, and watched it fail. The app was buggy, customers would not download it, and the underlying point-of-sale systems they had to integrate with were a mess of proprietary servers and disconnected data. But that failure revealed something bigger. Restaurant owners hated their clunky, expensive, on-premise systems. They just had no good alternatives. Narang and his team decided to stop building a feature and instead build the entire replacement. They called it Toast.

The Pivot from Payment App to Operating System

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What you'll learn

  • 1 (04:02) **The Problem with Restaurant Tech** - Aman Narang describes the moment a new restaurant's point-of-sale system crashed on opening night, revealing how mission-critical these systems are.
  • 2 (05:42) **The Core Insight** - Before Toast, restaurant software was clunky, expensive, hard to update, and lived on local servers, disconnected from the cloud.
  • 3 (06:04) **The Origin Story** - The idea for Toast began with a universal frustration: waiting for the dinner check.
  • 4 (08:29) **From Indeca to Founding Team** - Aman met his co-founders Steve Fredette and John Grimm at Indeca, where they built a business intelligence platform and mobile e-commerce apps.
  • 5 (11:34) **Leaning In to the Startup** - After Indeca's acquisition, Steve quit first, followed by John, pushing Aman to commit fully to their undefined venture.
  • 6 (13:31) **The "Firebrand Saints" Moment** - At a bar near MIT, the team experienced the long wait for a check and decided to build a mobile payment app.
  • 7 (16:18) **Why the App Failed** - The payment app was buggy and unreliable because it depended on integrating with existing, non-cloud-based POS systems.

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Show Notes

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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