Toast

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 Restaurants were struggling with outdated software that many owners hated.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.

Aman Narang

Co-Founder & CEO

Toast

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/

Aman Narang

Co-Founder & 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?

Aman Narang

Co-Founder & CEO

Toast

In this new episode of CRO Confidential, we take a look at the proven customer acquisition strategies behind Toast's explosive growth to over $1.1B ARR. Hosted by Founders Fund Partner Sam Blond, this episode features the CRO of Toast Jonathan Vassil, who walks us through Toast's go-to-market and customer acquisition strategies. -------------------------------------------------------------------------------------------- This episode is sponsored by: Northwest Registered Agent When starting your business, it's important to use a service that will actually help you. Northwest Registered Agent is that service. They'll form your company fast, give you the documents you need to open a business bank account, and even provide you with mail scanning and a business address to keep your personal privacy intact. Visit https://www.northwestregisteredagent.com/saastr to get a 60 percent discount on your next LLC.

Jonathan Vassil

CRO

Toast

Maggie Crowley is VP of product at Toast and previously vice president and head of product at Charlie Health, senior director of product management at Drift, and a PM at TripAdvisor. She’s also the host of Build, a podcast dedicated to product and product management. In today’s conversation, Maggie shares: • The value of building a broad-based PM skill set • Three qualities of the best product managers • A step-by-step guide for crafting a product strategy • How to break into PM • Why great writing is often just simplifying your writing • Why being too data-driven is a red flag • The impact of content creation on Maggie’s career — Brought to you by Productroadmap.ai—AI to connect your roadmaps to revenue | Composer—the AI-powered trading platform | Eppo—Run reliable, impactful experiments — Find the full transcript at: https://www.lennyspodcast.com/mastering-product-strategy-and-growing-as-a-pm-maggie-crowley-toast-drift-tripadvisor/ — Where to find Maggie Crowley: • X: https://twitter.com/maggiecrowley • LinkedIn: https://www.linkedin.com/in/maggie-crowley-42a97112/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Maggie’s background (04:06) Three common traits among the best product managers (09:33) Strategy is an important but small part of the job (11:14) How to get better at simplification (13:39) Tips on simplifying your writing (15:13) Ownership as a PM (17:53) Examples of simplifying your work (19:39) Maggie’s Slack support group (21:37) How to improve on following up on your work (23:23) A realistic time horizon for PMs (26:31) Staying in your role vs. trying a new opportunity (27:37) The importance of “carrying the water”  (28:56) Pros and cons of the PM job (31:42) Advice on landing a PM role (34:36) Maggie’s step-by-step process for writing your product strategy (39:55) Not every feature needs a strategy (46:29) The value of working through the process (48:09) Maggie’s one-pager doc  (54:16) Contrarian corner (55:44) The worst product Maggie ever shipped (58:33) Why being “data-driven” is a red flag (1:01:10) Content creation as a career accelerator (1:14:27) Closing thoughts (1:15:17) Lightning round — Referenced: • David Cancel on LinkedIn: https://www.linkedin.com/in/dcancel/ • On Writing Well: The Classic Guide to Writing Nonfiction: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548 • Notion: https://www.notion.so/ • The Minto Pyramid Principle and the SCR Framework: https://www.lennysnewsletter.com/p/minto-pyramid-principle-scr • Drift: https://www.drift.com/ • Maggies Top 5 Product Lessons for 2021: https://www.drift.com/podcasts/build/?wchannelid=hg0p3zf4yx&wmediaid=nxrdvmotr3 • Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennyspodcast.com/unpacking-amazons-unique-ways-of-working-bill-carr-author-of-working-backwards/ • Inside Linear: Building with taste, craft, and focus | Karri Saarinen (co-founder, designer, CEO): https://www.lennyspodcast.com/inside-linear-building-with-taste-craft-and-focus-karri-saarinen-co-founder-designer-ceo/ • Adam Medros on LinkedIn: https://www.linkedin.com/in/amedros/ • How Figma builds product: https://www.lennysnewsletter.com/p/how-figma-builds-product • Strategy Document Template: https://docs.google.com/document/d/1frggEj_gfFD4--8eNkkyY-zHryXbN5uIS8uiMDCYVes/edit • Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: https://www.lennyspodcast.com/shreyas-doshi-on-pre-mortems-the-lno-framework-the-three-levels-of-product-work-why-most-execution-problems-are-strategy-problems-and-roi-vs-opportunity-cost-thinking/ • Einstein quote: https://www.brainyquote.com/quotes/albert_einstein_122232 • The Presentation Secrets of Steve Jobs: How to Be Insanely Great in Front of Any Audience: https://www.amazon.com/Presentation-Secrets-Steve-Jobs-Insanely/dp/0071636080 • Thinking in Bets: Making Smarter Decisions When You Dont Have All the Facts: https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions/dp/0735216371 • Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212/r • Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o • Future: https://www.future.co/ • Ladder: https://www.joinladder.com/ • Pump Log: https://pumplogapp.com/ • Huckleberry: https://huckleberrycare.com/ • Toast: https://pos.toasttab.com/ • Careers at Toast: https://careers.toasttab.com/homepage • What differentiates the highest-performing product teams | John Cutler (Amplitude, The Beautiful Mess): https://www.lennyspodcast.com/what-differentiates-the-highest-performing-product-teams-john-cutler-amplitude-the-beautiful-mess/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Maggie Crowley

VP of Product

Toast

John Cutler writes the popular and beloved product newsletter The Beautiful Mess. For many years, he was a Product Evangelist at Amplitude, which led him to meeting and working with a large number of product teams around the world. Through this role, he gained unique insight into how the best product teams operate. In today’s episode, John reflects on leaving his role at Amplitude, and explains the attributes that the top 1% of product teams share. We also go deep into some of his favorite frameworks and discuss the best way to apply these frameworks to your work. We also unpack skills like product sense and product mindset, and what he’s planning in his new role at Toast. — Find the full transcript here: https://www.lennysnewsletter.com/p/what-differentiates-the-highest-performing — Thank you to our wonderful sponsors for supporting this podcast: • Merge—A single API to add hundreds of integrations into your app: http://merge.dev/lenny • Eppo—Run reliable, impactful experiments: https://www.geteppo.com/ • Vanta—Automate compliance. Simplify security: https://vanta.com/lenny — Where to find John Cutler: • Twitter: https://twitter.com/johncutlefish • LinkedIn: https://www.linkedin.com/in/johnpcutler/ • Newsletter: https://cutlefish.substack.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — Referenced: • Amplitude: https://amplitude.com/ • The North Star Playbook: https://info.amplitude.com/north-star-playbook • Craig Daniel on LinkedIn: https://www.linkedin.com/in/craigmdaniel/ • Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595 • AppFolio: https://www.appfolio.com/ • High Leverage Product Evangelism: https://cutlefish.substack.com/p/high-leverage-product-evangelism • Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/ • The Culture Map: Breaking Through the Invisible Boundaries of Global Business: https://www.amazon.com/Culture-Map-Breaking-Invisible-Boundaries/dp/1610392507 • Innovation Labs: https://innovationlabs.com/ • BEES: https://mybeesapp.com/ • Marty Cagan on Lenny’s Podcast: https://www.lennysnewsletter.com/p/the-nature-of-product-marty-cagan#details • Sooner Safer Happier: Antipatterns and Patterns for Business Agility: https://www.amazon.com/Sooner-Safer-Happier-Patterns-Antipatterns/dp/1942788916 • Teresa Torres on LinkedIn: https://www.linkedin.com/in/teresatorres/ • Andrew Huberman on Instagram: https://www.instagram.com/hubermanlab/?hl=en • TBM 49/52: Pyramid of Leadership Self/Other Awareness: https://cutlefish.substack.com/p/tbm-4952-pyramid-of-leadership-selfother • ChatGPT: https://chat.openai.com/chat • How to Measure Anything: Finding the Value of Intangibles in Business: https://www.amazon.com/How-Measure-Anything-Intangibles-Business-ebook/dp/B00INUYS2U • Accelerate: The Science of Lean Software and DevOps: Building and Scaling High Performing Technology Organizations: https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339 • User Story Mapping: Discover the Whole Story, Build the Right Product: https://www.amazon.com/User-Story-Mapping-Discover-Product/dp/B08TZGKKF2 • Build with Maggie Crowley podcast: https://podcasts.apple.com/us/podcast/build-with-maggie-crowley/id1445050691 • One Knight in Product podcast: https://www.oneknightinproduct.com/index.html#page-top • Sunny Bunnies on Netflix: https://www.netflix.com/title/81286920 • Booba on Netflix: https://www.netflix.com/title/81011059 • Toast: https://pos.toasttab.com/ • Drift: https://www.drift.com/ John’s list of high-performing people worth following: • Dr. Cat Hicks (@grimalkina) https://www.linkedin.com/in/drcathicks/  • Stephanie Leue https://www.linkedin.com/in/stephanie-leue/ • Amy Edmondson (@AmyCEdmondson) https://www.linkedin.com/in/amedmondson/ • Dominica DeGrandis (@dominicad) https://www.linkedin.com/in/dominicadeg/ • Courtney Kissler https://www.linkedin.com/in/courtney-kissler-0930681/ • Christina Wodtke (@cwodtke) https://www.linkedin.com/in/christinawodtke/ • Matthew Skelton https://www.linkedin.com/in/matthewskelton/ • Heidi Helfand (@heidihelfand): https://www.linkedin.com/in/heidihelfand/ — In this episode, we cover: (00:00) What is a product evangelist? John’s unique role at Amplitude (05:50) John’s reflections and feelings on leaving Amplitude (17:28) What John’s doing next (18:52) John’s newsletter: The Beautiful Mess (27:49) What do the top 1% of product teams have in common? (40:08) Different ways companies are successful, and why anyone can improve (45:55) Investing in people vs. investing in processes (48:49) The importance of culture and values (49:59) Global company cultures: the individualist vs. the collectivist   (55:55) Why it’s hard to make changes in large companies (58:49) How to view frameworks (1:01:02) The spectrum of performance in big and small companies (1:05:27) Examples of high-performing people who work outside of Silicon Valley (1:09:02) The skill of product management (1:11:35) The value of learning a bit about everything (1:13:46) Why do people often underestimate the loops available at their company (1:16:20) Chronic vs. acute issues at companies (1:18:07) Unpacking the skills behind product sense and product mindset (1:20:44) A place for people without the traditional meritocracy mindset (1:22:38) John’s writing process and what he plans on writing about next (1:27:52) How to use ChatGPT for learning and levity (1:31:56) Lightning Round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

John Cutler

Product Evangelist and Newsletter Author

Toast