
Toast: Aman Narang. How a Long Wait for the Dinner Check Launched a $2 Billion Business.
Hosted by Guy Raz
- 51m
- Transcript
Summary
Written by a model from the transcript; not yet reviewed.
This episode explores the founding and growth of Toast, the restaurant point-of-sale and management platform, through an interview with co-founder and CEO Aman Narang. The guest details his early career at Endeca, the mobile app boom following the release of the iPhone, and the frustrating dinner check experiences that initially inspired a failed consumer payment app. After recognizing that restaurant owners hated their fragmented, legacy on-premises technology, the founders pivoted to build a cloud-based operating system designed specifically for busy restaurants. The discussion covers the company's early struggles operating out of an unfinished Boston basement, navigating early technological failures, surviving a 90% revenue drop during COVID-19, and ultimately expanding to power nearly twenty percent of small business restaurants in the United States.
- When building enterprise software, tailor your platform entirely to the specific workflow complexities of the target industry rather than trying to build a generic tool. 28:33
- Instead of letting early product failures discourage the team, use those obstacles to uncover the deeper, systemic operational problems customers actually need solved. 20:25
- In the early stages of a startup, founding teams can iterate faster and solve problems more effectively by working directly on-site with their first beta customers. 39:37
Chapters
- 0:00Sponsor Introduction
The episode opens with a brief sponsor message from Anthropic, setting the tone for the show.
- 6:13Host and Guest Introduction
Guy Raz introduces the episode and sets up the story of Aman Narang and Toast.
- 7:30The Dinner Check Frustration
Aman Narang explains the everyday annoyance of waiting for a check and how it sparked the idea for Toast.
- 8:15Pivot to Restaurant Operating System
Realizing the broader problem, the founders decide to replace the entire restaurant operating system, not just payment.
- 36:00Leadership Shift and Growth
A new CEO, Chris Camparato, joins to help the company scale and improve operations.
- 37:07Early Customer Acquisition
They secure their first restaurant customer, Dwell Time, and learn hard lessons about reliability and support.
- 41:52Scaling Challenges and Partnerships
Toast partners with GFS to expand beyond Boston, but struggles with scalability and customer support infrastructure.
- 49:41COVID‑19 Impact and Pivot
The pandemic forces Toast to cut staff, pivot to QR code ordering, and focus on off‑premise sales.
- 51:03IPO and Public Life
Toast goes public in 2021, becoming a publicly traded company with a new direction.
- 51:40CEO Return and Future Vision
Aman Narang returns as CEO, reflecting on leadership, partnership, and the company's future.
- 52:24Assessing Market Share and Profitability
The conversation begins with an overview of Toast’s recent profitability and its current 15‑20% market penetration in U.S. restaurants.
- 53:11Targeting Busy Restaurants and AI Opportunities
Toast’s strategy focuses on busy restaurants and leveraging AI to increase sales and customer retention.
Highlights
- 11:07
Almost Quitting to Build Appsstory
The guest and his co-founder considered leaving Endeca to build mobile apps after the iPhone launched, but their boss convinced them to build the mobile business internally instead.
- 15:36
Frustration Inspiring a New Appstory
While waiting ten minutes for a check at a Boston bar called Firebrand Saints, the founders were inspired to build a mobile app so diners could pay their bills from their phones.
- 20:25
Realizing the Full Scopeinsight
The guest explains how the team initially underestimated the vast operational scope of legacy point-of-sale systems, which handled everything from kitchen stations and employee scheduling to inventory and hardware integration.
- 26:50
The Fragmented Restaurant Tech Stackstory
A restaurant owner showed the founders that he was juggling completely separate software systems for payments, loans, accounting, inventory, online ordering, gift cards, and scheduling, with online orders arriving on a fax machine.
- 36:03
Bootstrapping in a Basementstory
To save money on early office space, the founders laid carpet and drywall in an unfinished, unheated basement, buying space heaters to house a team of up to ten people by late 2013.
- 44:18
Google Voice Support Linestory
In the early days, the company's 24/7 customer support phone number routed to a Google Voice number that rang the founders' cell phones directly, leading the guest to personally pick up late-night outage calls.
- 49:21
Surviving the Pandemic Collapsedata
When COVID-19 shut down restaurants, Toast's revenues dropped over ninety percent within weeks, forcing the company to cut 55 percent of its team and quickly pivot to build off-premise QR code ordering features.
Quotes
“The real problem wasn't just paying the bill. It was the technology running the entire restaurant.”
Guy Raz · 7:58 “We were trying to break new ground with this technology.”
Unnamed speaker · 10:14 “2011, Oracle acquires Indica for about a billion dollars.”
Guy Raz · 12:36 “We know, for example, that if a guest comes into a restaurant three times, they're more likely to become a regular.”
Unnamed speaker · 53:47 “The harder you work, the luckier you get.”
Unnamed speaker · 58:23 “We launched this product, uh, recently called Toast IQ Grow.”
Unnamed speaker · 53:57
Sponsored segments
- Anthropic 0:00–0:17
- US Bank 1:07–4:00
- Mobile Supreme 4:47–5:05
- NetSuite 32:17–33:42
About this episode
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 pivotWhy investors rejected Toast again and againHow to convince customers to replace mission-critical softwareWhy Toast intentionally stayed small before scalingThe leadership lesson Aman learned after almost breaking the companyHow Toast survived COVID after restaurants shut downWhat founders should look for when choosing a co-founder Timestamps: 11:25 — The frustrating restaurant experience that inspires Toast15:41 — The first product fails—and reveals a bigger opportunity16:43 — 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 hand34:18 — Pitching hundreds of restaurant owners before finding believers38:08 — Why customer obsession beats competitor obsession44:17 — 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 https://www.instagram.com/howibuiltthis/ X → @HowIBuiltThis https://x.com/howibuiltthis Facebook → How I Built This https://www.facebook.com/howibuiltthis Follow Guy Raz: Instagram → @guy.raz https://www.instagram.com/guy.raz/ YouTube → guy_raz https://www.youtube.com/channel/UCNSfrxNEmCruNtjIzxCBHjg X → @guyraz https://x.com/guyraz Substack → guyraz.substack.com http://guyraz.substack.com Website → guyraz.com http://guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Transcript
10,205 words · 2 speakers
Speaker names marked are inferred from speaking time and the show’s known hosts — they are not voice-verified.
Topics
- Toast
- Boston
- AI
- Endeca
- GFS
- Micros
- NCR
- Firebrand Saints
- Cambridge
- Oracle
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