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Restaurants were struggling with outdated software that many owners hated.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.
Follow How I Built This:
Instagram → @howibuiltthis
X → @HowIBuiltThis
Facebook → How I Built This
Follow Guy Raz:
Instagram → @guy.raz
YouTube → guy_raz
X → @guyraz
Substack → guyraz.substack.com
Website → guyraz.com
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
What It Takes to Build Software for 171,000+ Restaurants | Aman Narang
Great software companies often come from understanding pain points at a very deep level.
On Grit, Aman Narang shares how Toast built trust with 171,000+ restaurant operators by helping restaurants manage everything from payments and online orders to staff scheduling and daily operations.
He also reflects on lessons around product-market fit and scaling a company before it’s fully ready.
Guest: Aman Narang, co-founder and CEO, Toast
Connect with Aman Narang
LinkedIn: https://www.linkedin.com/in/aman-narang-155628/
Connect with Toast
LinkedIn: https://www.linkedin.com/company/toast-inc/
Instagram: https://www.instagram.com/toasttab/
X: https://x.com/ToastTab?lang=en
Connect with Joubin:
X: https://x.com/Joubinmir
LinkedIn: https://www.linkedin.com/in/joubin-mirzadegan-66186854/
Email: grit@kleinerperkins.com
Follow on LinkedIn:
https://www.linkedin.com/company/kpgrit
Follow on X:
https://x.com/KPGrit
Learn more about Kleiner Perkins:https://www.kleinerperkins.com/
20VC: Five Lessons Scaling Toast to $14BN Market Cap | The Biggest Mistakes Founders Make in Fundraising, Hiring and Selling with Aman Narang, CEO @ Toast
Aman Narang is the Co-Founder and CEO of Toast, one of the best-in-class vertical SaaS companies of our time with a market cap today of $13.5BN. Five astonishing stats that show the quality of the Toast business today:
$1.2bn in ARR with 48.4% from payments.
Toast Capital has reached $1bn in annualised loans originated.
875k restaurants in the US (Toast has 112k: 13% market share)
75% of locations are coming from inbound channels
The first investor in the company invested $500K at a $3M price
In Today's Episode with Aman Narang We Discuss:
1. The Biggest Mistakes Founders Make:
Why does Aman believe that founders should spend more time fundraising and with investors early?
Why does Aman believe founders should hire managers before they think they need them?
Why does Aman believe that founders do not give up control early enough?
2. Lessons Scaling to a $14BN Market Cap:
What did Aman and Toast do so successfully that allowed them to scale to $14BN market cap in 12 years? What worked?
What are the single biggest mistakes Toast made that hindered their growth most?
What are the first things to break in hyperscaling companies?
What opportunity did Aman and Toast not take that with the benefit of hindsight, he wishes they had taken?
3. Crucible Moment Decisions: Expansion:
How did Aman and Toast know when was the right time to release a second product?
What has enabled Toast Capital to scale to $1BN in loans so efficiently?
How did Aman and Toast scale so successfully into both enterprise and SMB? What are the biggest lessons from doing so? What did not work?
How do Aman and Toast approach geographic expansion? How do they choose which countries to expand into?