Grammarly

Today, I’m talking with Shishir Mehrotra, the CEO of Superhuman, the company formerly known as Grammarly, which is still its flagship product. Back in August, Grammarly shipped a feature called Expert Review, which allowed you to get writing suggestions from AI-cloned “experts,” and recently, reporters at The Verge and other outlets discovered that those experts included me, among many others.  No one ever asked permission to use our names this way, and a lot of reporters were outraged by this. To Shishir’s credit, he did not cancel our interview and he came on and stuck it out. This conversation got tense at times, and it’s clear we disagree about how extractive AI feels for people. There’s a lot in this one, and I’m excited to hear what you think. Read the full interview transcript on The Verge. Links: Why I’m suing Grammarly | New York Times Grammarly will stop using identities without permission | The Verge Grammarly to keep using writer identities unless they opt out | The Verge Grammarly turned me into an AI editor and I hate it | Platformer Grammarly is using our identities without permission | The Verge Grammarly is changing its name to Superhuman | The Verge Grammarly wants to become an ‘AI productivity platform’ | The Verge Viacom v. YouTube, 2007 | Electronic Frontier Foundation Subscribe to The Verge to access the ad-free version of Decoder! Credits: Decoder is a production of The Verge and part of the Vox Media Podcast Network. Decoder is produced by Kate Cox and Nick Statt. This episode was edited by Xander Adams. Our editorial director is Kevin McShane.  The Decoder music is by Breakmaster Cylinder. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Shishir Mehrotra

Founder and CEO

CodaSuperhumanGrammarly

Noam Lovinsky is the CPO @ Superhuman (formerly Grammarly). Prior to Superhuman he was a Senior Director of Product Management at Facebook. In his earlier years, he was CPO @ Thumbtack and spent 5 years as a Director of Product Management at Google where he was responsible for all of Youtube's applications. AGENDA: 03:43 What is Great Product Leadership in a World of AI 07:45 Does the Design Phase Die in a World of Vibe Coding 12:21 How AI Changes Product Development Most 22:23 Accelerating Product Development 29:32 AI's Impact on Product Building 34:19 Predictions for 2026 34:45 Quick Fire Round 38:41 Reflections and Future Plans

Noam Lovinsky

Chief Product Officer

GrammarlySuperhuman

Today’s show: *Why rebrand an app with 40 million daily active users? On TWiST, Grammarly CEO Shishir Mehrotra swings by to explain why he’s renaming his company after the mail app he just purchased, Superhuman. Plus he’s giving us a first look at the startup’s new AI assistant, Superhuman Go, digging into their new agent-centered strategy, looking ahead at the potential for AI job displacement, and more. Jason and Alex also talk about our new nuclear deal with Westinghouse and Japan, OpenAI’s conversion and what it means for Microsoft, 1x’s tele-operated Neo-bot for chores, and much more! Timestamps: (00:07:56) Jason is headed to Tokyo, and NOT just for skiing this time! (10:00) Uber AI Solutions**:** Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at Uber.com/twist (00:12:21) Untangling this US government-Japan-Westinghouse deal for nuclear power… and why nuclear power is SO important (20:00)DevStats translates complex engineering metrics into a shared language everyone at your company can understand. Get 20% off by going to https://www.DevStats.com/twist (00:20:04) Why Jason says sabbaticals and 4 day work weeks are for established brands, not startups (30:00) Perspective AI: Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/twist. (00:33:01) Will income inequality become a concern, even for the wealthy? Jason says YES. (00:37:29) Shishir Mehrotra from Gram— NO WAIT, Superhuman! joins us to talk name changes (00:38:16) Using Grammarly as a model for the new AI assistant, Superhuman Go. (01:08:39) Nvidia shot past $5 TRILLION in value… How is no one freaked out about this?! (01:14:52) OpenAI executed their conversion… but Jason says “public benefit corporation” status is pretty meaningless (01:25:02) Checking out the Neo robot from 1x… he wants to help you with chores and he’s for sale! (01:32:09) Uber’s speeding up its self-driving plans Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Thank you to our partners: Perspective AI - Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/twist. DevStats translates complex engineering metrics into a shared language everyone at your company can understand. Get 20% off by going to https://www.DevStats.com/twist Uber AI Solutions: Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at Uber.com/twist Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Check out Jason’s suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Shishir Mehrotra

Founder and CEO

CodaSuperhumanGrammarly

What if your tools shared context like your team does? This week on Grit, Shishir Mehrotra shares how the Coda and Grammarly collaboration unlocks context as a “superpower,” reflects on his early days at Google and YouTube, and hints at a future where tools anticipate intent and amplify how we work. He also shares how this paves the way for agent-based workflows and AI-native communication, beginning with Superhuman’s email experience. Guest: Shishir Mehrotra, co-founder of Coda and CEO of Grammarly Connect with Shishir X LinkedIn Chapters: 00:00 Trailer 01:24 Introduction 02:09 Zoo vs safari 12:02 A TV ahead of its time 21:25 Product decisions 31:25 The data behind the algorithm 37:26 The AI native productivity suite 48:06 Agents are digital humans 57:55 Pressure trade-off 1:12:50 Insulated from judgment 1:25:19 Who Grammarly is hiring 1:25:51 What “grit” means to Shishir 1:29:30 Outro Mentioned in this episode: YouTube, Ray William Johnson, Spotify, Twitch, MTV, Chris Cox, Facebook, TikTok, Google TV, Centrata, Google Chrome, Android, Gmail, Microsoft, Super Bowl, Mosaic, Panasonic, Sony, Susan Wojcicki, Rishi Chandra, Apple TV, Amazon Firestick, Comcast, LoudCloud (Opsware), Quest Communications, AT&T Southwestern Bell, Salar Kamangar, Patrick Pichette, Eric Schmidt, OpenAI ChatGPT, Google Gemini, Mark Zuckerberg, Meta Platforms, Sundar Pichai, Larry Page, Sergey Brin, Hamilton, Reid Hoffman, Sam Altman, Tesla, Waymo, Airtable, Notion, Max Lytvyn, Alex Shevchenko, Superhuman, Duolingo, Luis von Ahn, Khan Academy, MrBeast, Facebook Messenger, Snap (Snapchat), WhatsApp, Google+, Meta LLaMa, Satya Nadella, Tim Cook, Daniel Gross Connect with Joubin X LinkedIn Email: grit@kleinerperkins.com Learn more about Kleiner Perkins

Shishir Mehrotra

Founder and CEO

CodaSuperhumanGrammarly

AGNTCY - Unlock agents at scale with an open Internet of Agents. Visit https://agntcy.org/ and add your support. Grammarly is no longer just a writing assistant. It's building an AI productivity platform that could rival Microsoft Copilot. In this episode, Luke Behnke, VP of Enterprise Product at Grammarly, shares how the company is moving beyond grammar correction into intelligent agents, enterprise workflows, and real-time AI tools. We dive into Grammarly's new Authorship feature, why AI fluency is becoming essential at work, how Grammarly is integrating tools like Coda and Superhuman, and what the future of multi-agent systems looks like. If you're curious about where AI at work is really heading, this conversation will give you a clear and powerful glimpse. (00:00) Preview and Intro (03:37) Meet Luke Behnke(05:00) Grammarly's Origin Story and Early Vision(09:11) Grammarly's UX Advantage(13:30) Competing With Microsoft Copilot and Built-In Assistants(17:48) What Is "Authorship" and Why It Matters(20:31) AI Detection vs Authorship Tracking(25:05) The Future of AI Transparency(27:43) Why AI Fluency Will Be a Job Requirement(32:04) Grammarly's Agentic Vision(34:11) The Rise of Context-Aware Enterprise Agents(38:24) Use Cases: Automating Tasks Across Tools with AI(40:21) The Coda Acquisition & Building the Agent Platform(44:48) The Future of Interoperable AI Agents(47:43) Why Agent Oversight Is Crucial in Enterprise AI(55:57) Measuring Grammarly's ROI in the Enterprise

Luke Behnke

VP of Enterprise Product

Grammarly

Today’s show: Grammarly is acquiring the beloved email app Superhuman! In today’s extremely timely episode, @alex sits down with Grammarly CEO Shishir Mehrotra and Superhuman founder Rahul Vohra to unpack why they’re merging, how they plan to combine apps and AI agents, and what it means for the future of email and work. PLUS they reveal how Grammarly’s 40M+ daily users already rely on email—and why this deal is the key to building the ultimate communication assistant. Don’t miss this deep dive into one of the most exciting AI acquisitions yet! #AI #Startups #Productivity #Grammarly #Superhuman #VentureCapital #MergersAndAcquisitions Timestamps: (0:00) Introduction to the future of robotics and AI regulation(1:11) Introduction of hosts and overview of today's topics(4:19) Cloudflare's new pay per crawl product (09:37) Northwest Registered Agent. Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today!(10:41) Polymarket segment on Apple's acquisition prospects(14:29) Grammarly and Superhuman CEOs interviews (19:42) Retool - Visit https://www.retool.com/twist and try it out today.(24:09) AI in productivity tools and email agents discussion(29:23) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/credits(30:46) Grammarly's AI platform and the acquisition of Superhuman(41:16) Introduction of Manu Sharma from Labelbox(41:47) The role of data labeling in AI and Labelbox's data factory(53:44) Labelbox's market position and capital efficiency post-ChatGPT(1:03:00) Advances in humanoid robotics with Jeff Cardenas from Apptronik(1:07:09) Market readiness and capabilities of Apollo 2 robots(1:13:27) Humanoid robotics: Google DeepMind partnership and international competition(1:20:54) US federal support for R&D in robotics(1:22:10) The evolution of humanoid robotics and Apptronik's growth in Austin Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Thank you to our partners: (09:37) Northwest Registered Agent. Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today! (19:42) Retool - Visit https://www.retool.com/twist and try it out today. (29:23) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/credits Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Check out Jason’s suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Shishir Mehrotra

Founder and CEO

CodaSuperhumanGrammarly

Rahul Vohra

Founder & CEO, Superhuman

Superhuman

New AI products are rapidly changing the landscape for businesses. This is especially true for the writing tool Grammarly. The $13 billion dollar software company’s CEO Rahul Roy-Chowdhury has taken the helm in the midst of a profound disruption. Host Jeff Berman talks to Rahul about how his time at Google helped prepare him for this moment, why he’s doubling down on building trust with customers, and how he thinks AI will shape the future of work. Read a transcript of this episode: https://mastersofscale.com Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Rahul Roy-Chowdhury

CEO

Grammarly

SaaStr 742: The Top 5 Secrets for Building Great Products with Leaders at Slack, Rubrik, and Grammarly As Product leaders, you have to build trust with CEOs and founders, align on vision and strategy, stay focused on the customer's problem, and effectively navigate misalignment to ensure your product has the greatest chances of success right out of the gate. But how do you tactically achieve all of that? Tamar Yehoshua, former CPO at Slack and Partner at IVP, Anneka Gupta, CPO of Rubrik, and Noam Lovinsky, CPO of Grammarly, shared practical advice at SaaStr Annual from the trenches so you can build great products and great teams all at once. Follow along with the full write-up of this podcast here. -------------------------------------------------------------------------------------------- SaaStr hosts the largest SaaS community events on the planet. Join us in 2024 at: SaaStr Annual: Sept. 10-12 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Podcast listeners can grab a discount on tickets here: https://www.saastrannual2024.com/buy-tickets?promo=fave20 -------------- This episode is sponsored by: Northwest Registered Agent Get more when Northwest Registered Agent starts your business. They'll form your company fast and stand up your entire business identity in minutes. That means business free domain, business email, website, hosting, address, mail scanning, business phone app, all within minutes. Visit https://www.northwestregisteredagent.com/saastr to get a 60 percent discount on your next LLC. This episode is sponsored by: Remote.com Feeling stuck in your talent search? Remote Talent is the leading job board for remote-first companies and startups. Visit Remote.com/jobs today to start building your dream team, anywhere in the world. This episode is sponsored by Pendo, the all-in-one product experience platform. Pendo helps your users do the things you really want them to do. You can try Pendo for free at Pendo.io/saastr and check out Mind The Product, the community for product people like… us.

Tamar Yehoshua

President of Product and Technology

GleanIVPSlack

Anneka Gupta

Chief Product Officer

Rubrik

Noam Lovinsky

Chief Product Officer

GrammarlySuperhuman

Noam Lovinsky has had a distinguished career in product, leaving an indelible mark at Facebook, YouTube, Thumbtack, and currently as the chief product officer at Grammarly. At Facebook, Noam helped establish the New Product Experimentation team; at Thumbtack, he was chief product officer; and at YouTube, he was one of the early product leaders overseeing the consumer experience. In our conversation, we discuss: • Challenges and lessons from reviving growth at YouTube and Thumbtack • Lessons from building Facebook’s New Product Experimentation team • Insights into Grammarly’s success • Knowing when it’s time to kill your project • Why diversifying your growth channels is critical • The power of visioning and storytelling in shaping product strategy • How to create space for innovation at large companies • The resilience and motivation of Grammarly’s team in Ukraine — Brought to you by: • Whimsical—The iterative product workspace • Vanta—Automate compliance. Simplify security. • LinkedIn Ads—Reach professionals and drive results for your business — Where to find Noam Lovinsky: • X: https://twitter.com/noaml • LinkedIn: https://www.linkedin.com/in/noaml/ — 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) Noam’s background (04:18) Noam’s lack of online presence (08:06) Lessons from YouTube: advocating for what’s best for yourself and the team (14:31) Prioritizing what’s best for the business (19:37) Knowing when it’s time to kill a project (21:47) Lessons from Thumbtack: diversifying growth channels and overcoming challenges (26:24) How Thumbtack turned growth around (31:44) Building Airbnb’s instant booking feature (35:28) Lessons from Thumbtack: team collaboration and product strategy (38:38) Lessons from Facebook: building the New Product Experimentation team (40:43) The importance of starting small and building community density (46:07) Advice for building a startup within a startup (48:52) Having an incentive system (49:34) Lessons from Grammarly: adapting to changing user needs and building for the masses (54:20) The scrappiness and profitability of Grammarly (56:56) The resilience and motivation of the Grammarly team in Ukraine (59:08) General career advice (01:01:02) When to pull back (01:02:58) Closing thoughts (01:03:56) Lightning round — Referenced: • Substack: https://substack.com/ • Hunter Walk on LinkedIn: https://www.linkedin.com/in/hunterwalk/ • The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/ • Salar Kamangar on LinkedIn: https://www.linkedin.com/in/salar-kamangar-5a059712/ • Grammarly: https://www.grammarly.com/ • Thumbtack: https://www.thumbtack.com/ • FRED on YouTube: https://www.youtube.com/FRED • How Airbnb Proved That Storytelling Is the Most Important Skill in Design: https://www.inc.com/yazin-akkawi/the-surprising-technique-airbnb-uses-to-better-sell-an-experience.html • Google+: https://en.wikipedia.org/wiki/Google%2B • Marco Zappacosta on LinkedIn: https://www.linkedin.com/in/marcozappacosta/ • Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier/ • Whitney Steele on LinkedIn: https://www.linkedin.com/in/whitneydsteele/ • David Shein on LinkedIn: https://www.linkedin.com/in/davidshein/ • The magic of thinking big, by Lenny Rachitsky: https://www.mindtheproduct.com/the-magic-of-thinking-big-by-lenny-rachitsky/ • What Seven Years at Airbnb Taught Me About Building a Business: https://www.lennysnewsletter.com/p/what-seven-years-at-airbnb-taught • New apps, new experiences: NPE Team, from Facebook: https://tech.facebook.com/engineering/2019/7/npe-team-from-facebook/ • The Origin Story of the BRC Trash Fence: https://journal.burningman.org/2016/05/black-rock-city/leaving-no-trace/the-origin-story-of-the-brc-trash-fence/ • Nike opens high-tech research and innovation lab: https://www.just-style.com/news/nike-opens-high-tech-research-and-innovation-lab/ • ChatGPT: https://chat.openai.com/ • Microsoft Copilot: https://copilot.microsoft.com/ • How to grow a subscription business | Yuriy Timen (Grammarly, Canva, Airtable): https://www.lennyspodcast.com/how-to-grow-a-subscription-business-yuriy-timen-grammarly-canva-airtable/ • “The cave you fear to enter holds the treasure you seek”: https://gointothestory.blcklst.com/the-cave-you-fear-to-enter-holds-the-treasure-you-seek-d624e28c3848 • Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067 • For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7 • Fargo TV series on Hulu: https://www.fxnetworks.com/shows/fargo • Arc browser: https://arc.net/ • Competing with giants: An inside look at how The Browser Company builds product | Josh Miller (CEO): https://www.lennyspodcast.com/competing-with-giants-an-inside-look-at-how-the-browser-company-builds-product-josh-miller-ceo/ — 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

Noam Lovinsky

Chief Product Officer

GrammarlySuperhuman

Guest: Rahul Roy-Chowdhury, CEO of Grammarly Driven by generative tools like ChatGPT, artificial intelligence is hot — but Grammarly CEO Rahul Roy-Chowdhury wishes that “AI” stood for something else: “Augmented Intelligence.” A longtime Googler and lifelong believer in using technology to make peoples’ lives better at scale, Roy-Chowdhury now leads a company well-positioned to do exactly that. “In the early days, Grammarly was all about the rules of language,” he says. “Now, with generative AI, we can actually help people across a much broader swath of communication tasks.” In this episode, Rahul and Joubin discuss digital distraction, responsible AI, John Oliver, Ali Ghodsi, the hype cycle, fragmentation, being kind to yourself, Amp It Up, intentional strategy, candid dialogue, Google Chrome, and Dancing with the Butterfly. In this episode, we cover: Growing up in India (01:05) Meaningful, impactful work (07:12) The potential of AI (13:09) Invisible AI (19:53) Would Grammarly go public? (23:51) What drives the business (28:19) Too many emails (31:05) Being an introvert CEO (35:11) How Rahul got the top job (37:36) Insecurity (39:48) Snowflake CEO Frank Slootman (41:57) Rahul’s decision-making framework (45:40) “I deprecated the thing I built” (54:12) The dino game (56:28) The book on Rahul’s desk (59:49) Who Grammarly is hiring and what “grit” means to Rahul (01:01:06) Links: Connect with RahulLinkedIn Connect with JoubinTwitter LinkedIn Email: grit@kleinerperkins.com  Learn more about Kleiner Perkins This episode was edited by Eric Johnson from LightningPod.fm

Rahul Roy-Chowdhury

CEO

Grammarly

Matt Rosenberg is Grammarly's Chief Revenue Officer and Head of Grammarly Business. He leads all B2B revenue, operations, and growth for Grammarly Business, Grammarly for Education, and Grammarly for Developers. Previously, as CRO of Compass, he took the company into the Fortune 500 and contributed to a more than eightfold increase in business growth. Prior to Compass, Matt served as Eventbrite's CRO leading them to become the largest event platform in the world by event count. In Today's Episode with Matt Rosenberg We Discuss: 1. From Miserable Lawyer to World Beating Sales Leader: How did Matt make the transition from lawyer to sales leader? What does Matt know now that he wishes he had known when he started in sales? What are Matt's biggest pieces of advice for anyone who wants to make a career change and is lacking confidence? 2. The Playbook and Hiring The Team: How does Matt define the "sales playbook"? Should the founder be the one to create and execute V1 of the playbook? Should the first sales hire be a rep or a sales leader? When is the right time to make that all-important first sales hire? 3. Discounting, Champions and Urgency: What can sales team do to create urgency in deal cycles? What works? What does not? How does Matt approach discounting? When to do it vs when not to? What level is acceptable? What are the biggest secrets to creating champions within prospects? Why does Matt believe that deals are won and lost in prospecting? 4. Developing Great Sales Talent: How does Matt use sales call recordings to train teams? What is his 3x3 matrix for coaching calls? What is a good reason to lose a deal vs a bad reason? How does Matt do deal reviews? What are the single biggest elements sales leaders can do to nurture sales talent? What are the biggest mistakes sales leaders make when developing talent internally?

Matt Rosenberg

CRO

Grammarly

This Week in Startups is brought to you by… CLA. Innovation takes balance. CLA's CPAs, consultants, and wealth advisors can help you get from startup to where you want to end up. Get started now at https://CLAconnect.com/tech Codecademy. Build the future you want to see with Codecademy. Codecademy Pro helps you learn everything you’ll need to shape what comes next in the tech space. Try it free for 14 days. Visit https://Codecademy.com/TWiST LinkSquares. Life for in-house legal just got a whole lot easier. From contract creation to execution and more, LinkSquares is the go-to for all your legal needs. Learn more at https://linksquares.com/twist * Today’s show: Grammarly CEO Rahul Roy-Chowdhury joins Jason to discuss his journey to CEO (15:28), Grammarly’s product features (26:20), AI integrations (32:28), and much more! * Time stamps: (0:00) Grammarly CEO Rahul Roy-Chowdhury joins Jason (4:19) Rahul's start in tech and his time on the Google Chrome team. (8:57) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech (10:24) The Chrome team and Chrome OS (15:28) Journey to Grammarly CEO (19:29) Exploring applications and platforms for Grammarly (25:05) LinkSquares - The go-to for all your legal needs, learn more at https://linksquares.com/twist (26:20) The product roadmap and what draws people into Grammarly (35:04) Grammarly's business and enterprise offerings (37:32) Codecademy - Try Codecademy Pro FREE for 14 days at http://codecademy.com/TWiST (38:53) Product Features: Knowledge Share and Grammarly Goals (42:28) The addition of Grammarly Go and the LLM powering it (47:12) Controversial product features (54:17) When to use the native desktop application and extensions (57:13) Future integration of AI and the path ahead * Follow Rahul: https://twitter.com/rahulrc * Read LAUNCH Fund 4 Deal Memo: https://www.launch.co/four Apply for Funding: https://www.launch.co/apply Buy ANGEL: https://www.angelthebook.com Great recent interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland, PrayingForExits, Jenny Lefcourt Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow Jason: Twitter: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast

Rahul Roy-Chowdhury

CEO

Grammarly

The rapid proliferation of cloud services has added to overwhelm among enterprise workers. Over the years, Grammarly has learned effective strategies to stand apart with users and business decision-makers while channeling customers' needs, whether in customer support, sales, HR, and marketing. CEO Brad Hoover shares the customer-centric principles and lessons that he has learned in growing their user base to tens of millions of enterprise and individual customers, with teams from Accenture to Zoom. Full video: https://youtu.be/zoyxXSYeZhM Want to join the SaaStr community? We're the 🌎largest community for B2B software. Subscribe for weekly updates: https://www.saastr.com/subscribeform Twitter: https://twitter.com/saastr LinkedIn: https://www.linkedin.com/company/2724976 Quora Group: https://www.quora.com/q/cloud Facebook: https://www.facebook.com/SaaStr/ Instagram: https://www.instagram.com/saastr/ Our North American Event: https://bit.ly/2OXeAYh Our European Event: https://bit.ly/2OZTad8

Brad Hoover

CEO

Grammarly

Yuriy Timen was Global Head of Marketing and Growth at Grammarly, and is now a full-time growth advisor, having worked with more than a dozen companies, including Canva, Airtable, Whimsical, Otter.ai, Oyster, Flo Health, and Clay. In today’s episode, Yuriy discusses the ever-changing world of growth, emerging growth tactics, and how to find your growth engine. You’ll learn the most effective strategies for driving user acquisition, how to balance and diversify organic and paid channels, when it’s time to change plans, how to vet new growth channel opportunities, and much more.— Find the full transcript here: https://www.lennysnewsletter.com/p/transform-your-subscription-growth —Where to find Yuriy Timen:• LinkedIn: https://www.linkedin.com/in/yuriytimen/• Twitter: https://twitter.com/thetimenator—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—Thank you to our wonderful sponsors for making this episode possible:• Flatfile: https://www.flatfile.com/lenny• Modern Treasury: https://www.moderntreasury.com/• Eppo: https://www.geteppo.com/—Referenced:• Casey Winters: https://www.linkedin.com/in/caseywinters/• Elena Verna: https://www.linkedin.com/in/elenaverna/• Lyka Pet Food: https://lyka.com.au/• Ethan Smith’s LinkedIn:  https://www.linkedin.com/in/ethanls/• Graphite: https://www.graphitehq.com/• Recast: https://getrecast.com/• Measured: https://www.measured.com/• INCRMNTAL: https://www.incrmntal.com/• Essentialism: The Disciplined Pursuit of Less: https://www.amazon.com/Essentialism-Disciplined-Pursuit-Greg-McKeown/dp/0804137382/• Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl/dp/0807014273/• The Splendid and the Vile: A Saga of Churchill, Family, and Defiance During the Blitz: https://www.amazon.com/Splendid-Vile-Churchill-Family-Defiance/dp/0385348711/• The All-In Podcast: https://www.allinpodcast.co/• Hustle: https://www.netflix.com/title/80242342• Mark Fiske at H.I.G.: https://higgrowth.com/team/mark-fiske/—In this episode, we cover:[03:49] Yuriy’s background[09:46] Different paths to growth for subscription-based products[13:21] When to lean into virality[15:39] What are network effects?[16:32] SEO strategy and timeline: how long can it take to see results?[24:22] The shifting landscape of paid media[28:09] The return of media mix modeling[32:01] How can you tell if media spending equates to business results?[33:44] Don’t spread yourself too thin[36:01] How to tell if you’ve taken a strategy far enough[38:02] When to lean into a strategy that’s working vs. when to think about diversification[42:13] Is there a shift from growth to survival?[46:19] Two reasons to do paid media[56:45] Why you shouldn’t dismiss TikTok (and other channels you might be overlooking)[59:36] Lightning round!—Production and marketing: https://penname.co/ 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

Yuriy Timen

Growth Advisor

Grammarly

Shishir Mehrotra is the co-founder and CEO of Coda, and formerly head of product and engineering at YouTube. In this episode, he shares his insights on growth strategy, how he evaluates talent, a peek at his upcoming book The Rituals of Great Teams, why reference checks are the most important step in the interview process, and so much more. Join us. — Find the full transcript here: https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/#transcript — Where to find Shishir Mehrotra: • Twitter: https://twitter.com/shishirmehrotra • LinkedIn: https://www.linkedin.com/in/shishirmehrotra/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — Thank you to our wonderful sponsors for making this episode possible: • Coda: http://coda.io/lenny • Flatfile: https://www.flatfile.com/lenny • Eppo: https://www.geteppo.com/— Referenced: • The Rituals of Great Teams Braintrust: https://coda.io/@shishir/join-the-rituals-of-great-teams-braintrust • Bing Gordon: https://www.kleinerperkins.com/people/bing-gordon/ • Switch by Chip Heath and Dan Heath: https://www.amazon.com/Switch-Change-Things-When-Hard/dp/0385528752 • PSHE diagram: https://coda.io/@shishir/pshe • Understanding Comics by Scott McCloud: https://www.amazon.com/Understanding-Comics-Invisible-Scott-McCloud/dp/1627652736 • Only Murders in the Building: https://www.hulu.com/series/only-murders-in-the-building-ef31c7e1-cd0f-4e07-848d-1cbfedb50ddf • WandaVision: https://en.wikipedia.org/wiki/WandaVision • Fidji Simo: https://twitter.com/fidjissimo • Daniel Ek: https://twitter.com/eldsjal/ • Reid Hoffman: https://twitter.com/reidhoffman? • Mamoon Hamid: https://twitter.com/mamoonha • Quentin Clark: https://twitter.com/quentinclark • Sarah Guo: https://twitter.com/saranormous —In this episode, we cover:[4:13] Shishir’s background at Google and current role at Coda[7:53] How Shishir got on the board of Spotify[8:58] Black loops and blue loops and how Coda uses this internal diagram [9:52] The black loop is how a product is naturally shared[12:15] The blue loop is the emotional loop on why products are shared[14:55] Why you should think in loops instead of funnels[18:20] Mining for your business’s loops by looking at what you tell job candidates[24:37] Shishir’s upcoming book The Rituals of Great Teams [26:30] The 3 golden rituals of teams[27:10] Coda’s golden ritual: Dory and Pulse[31:29] Shishir’s most impactful rituals: Arianna Huffington’s reset, Gusto’s incredible hiring call, and Coinbase’s Rapids[40:38] How you find your own team’s rituals[42:50] How to change things when change is hard[45:01] Airbnb’s unique rituals[46:45] A backstory on YouTube, and valuing consistency over comprehensiveness[53:00] Eigenquestions: What they are, how to use them, and examples[59:05] One of Shishir’s favorite retired interview questions [1:03:11] How to evaluate talent, a story about YouTube, and breaking down PSHE[1:15:20] How to approach reference checks and what questions to ask[1:24:33] Favorite books[1:25:50] Favorite TV shows and movies[1:26:50] Favorite interview questions[1:28:44] Who in the industry Shishir respects as a thought leader[1:30:10] His go-to karaoke song[1:30:40] Where you can find Shishir— Production and marketing: https://penname.co/ 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

Shishir Mehrotra

Founder and CEO

CodaSuperhumanGrammarly

Sam Parr (@theSamParr) sits down with Max Lytvyn (@Max_lytvyn), co-founder and head of revenue at Grammarly, to talk about the founding story of the company, how he grew it from 0 to $13B in revenue, why he decided to hire an outside CEO, and much more. ----- Show Notes: (00:00) - Max's background (05:15) - Why people underestimate Grammarly (12:00) - Grammarly's breakthrough moment (24:40) - Business ideas that go with Grammarly ----- Links: * Do you love MFM and want to see Sam and Shaan's smiling faces? Subscribe to our Youtube channel. * Want more insights like MFM? Check out Shaan's newsletter. * Grammarly.com ----- Past guests on My First Million include Rob Dyrdek, Hasan Minhaj, Balaji Srinivasan, Jake Paul, Dr. Andrew Huberman, Gary Vee, Lance Armstrong, Sophia Amoruso, Ariel Helwani, Ramit Sethi, Stanley Druckenmiller, Peter Diamandis, Dharmesh Shah, Brian Halligan, Marc Lore, Jason Calacanis, Andrew Wilkinson, Julian Shapiro, Kat Cole, Codie Sanchez, Nader Al-Naji, Steph Smith, Trung Phan, Nick Huber, Anthony Pompliano, Ben Askren, Ramon Van Meer, Brianne Kimmel, Andrew Gazdecki, Scott Belsky, Moiz Ali, Dan Held, Elaine Zelby, Michael Saylor, Ryan Begelman, Jack Butcher, Reed Duchscher, Tai Lopez, Harley Finkelstein, Alexa von Tobel, Noah Kagan, Nick Bare, Greg Isenberg, James Altucher, Randy Hetrick and more. ----- Additional episodes you might enjoy: • #224 Rob Dyrdek - How Tracking Every Second of His Life Took Rob Drydek from 0 to $405M in Exits • #209 Gary Vaynerchuk - Why NFTS Are the Future • #178 Balaji Srinivasan - Balaji on How to Fix the Media, Cloud Cities & Crypto #169 - How One Man Started 5, Billion Dollar Companies, Dan Gilbert's Empire, & Talking With Warren Buffett • ​​​​#218 - Why You Should Take a Think Week Like Bill Gates • Dave Portnoy vs The World, Extreme Body Monitoring, The Future of Apparel Retail, "How Much is Anthony Pompliano Worth?", and More • How Mr Beast Got 100M Views in Less Than 4 Days, The $25M Chrome Extension, and More

Max Lytvyn

Co-Founder and Head of Revenue

Grammarly

Every high-growth organization inevitably reaches the point of pivoting its strategy and offerings to capture new audiences—a journey made more complex with the new demands emerging this past year. In this session, Dorian Stone will share lessons learned from Grammarly's evolution from consumer to SMB to enterprise, address common assumptions and pitfalls in the process of scaling, and reveal must-know strategies to drive efficient growth this year and beyond.

Dorian Stone

Head of Organizations Revenue

Grammarly

Featuring 3 prominent Founders - from Calendly, Coda and LaunchDarkly - that have achieved scale, at "Founder Confidential" you will hear about the highs and lows of fundraising, working with a VC board, and real talk about what it really is like to be a true Founder. Moderator: Lloyed Lobo, Co-Founder, Boast.AI Panelists: Shishir Mehrotra, Cofounder and CEO, Coda Edith Harbaugh, Cofounder and CEO, LaunchDarkly David Barrett, Founder and CEO, Expensify Jason Lemkin, Founder and CEO, SaaStr Blog post and video: https://www.saastr.com/founder-confidential-saas-fundraising-expensify-launchdarkly-coda-boast-saastr/ Sponsors: https://www.invoca.com/ https://stripe.com/ https://www.ontheclock.com/

Shishir Mehrotra

Founder and CEO

CodaSuperhumanGrammarly

Edith Harbaugh

Co-Founder and Executive Chair

LaunchDarkly

David Barrett

Founder & CEO

Expensify

Your board of directors can make or break you. In fact, Reid believes, the wrong board member can break your company faster than the right board member can make it. Learn the five vital mindset shifts that can help you create a better board, with insights from Mellody Hobson, the co-CEO of Ariel Investments and the chair of the Starbucks board, along with Lisa Shalett, co-founder of Extraordinary Women on Boards, and Shishir Mehrotra, founder and CEO of Coda (Reid's on their board). These universal lessons don’t only speak to founders assembling their very first board, or board directors looking for best practices – they also offer important advice for team-building across the board. Read a transcript of this episode: https://mastersofscale.com Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Mellody Hobson

President

Ariel Investments

Lisa Shalett

Co-Founder

EBExtraordinary Women on Boards

Shishir Mehrotra

Founder and CEO

CodaSuperhumanGrammarly

Check out Coda: https://coda.io FOLLOW Shishir: https://twitter.com/shishirmehrotra FOLLOW Jason: https://linktr.ee/calacanis

Shishir Mehrotra

Founder and CEO

CodaSuperhumanGrammarly

Shishir Mehrotra is the Founder & CEO @ Coda, the startup that brings all of your words and data into a flexible all-in-one doc. To date, Shishir has raised over $140M from some great names including Greylock, Kleiner Perkins, General Catalyst, NEA and Homebrew to name a few. Prior to founding Coda, Shishir spent an incredible 6 years at Google in a couple of different roles; first as Director of Product for Youtube Monetisation and then moving to Youtube VP of Engineering, Product and UX. Before Google, Shishir was with Microsoft for 6 years as a Director of Program Management. Shishir also serves on the board of Spotify. In Today's Episode You Will Learn: 1.) How Shishir made his way into the world of tech, came to be VP of Engineering, Product and UX @ Youtube and how it led to founding Coda? 2.) What is the No 1 quality of a good decision? How does Shishir think through reversible vs irreversible decisions? What are the 4 phases of decision-making? When should decisions be based on speed vs not? How can teams adjust questions to come to more productive outcomes? 3.) How does Shishir encourage debate and dissent within team discussions? How can leaders build deep trust with their teams? How can leaders create true democracy for idea sharing and meritocracy? Should ideas always be acted on immediately? What are the pros and cons? 4.) How does Shishir think about and evaluate his own operating cadence? How has this changed over time? How does Shishir approach time allocation? What have been his core learnings? How does Shishir divide his time between proactive and reactive tasks? 5.) How does Shishir approach OKR setting? What can leaders do to create aspirational and inspirational goals? How should goals be correctly communicated across orgs? How many OKRs should one team/person have? How should attribution across OKRs be given? Items Mentioned In Today's Show: Shishir's Fave Book: Switch: How to change things when change is hard As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Shishir Mehrotra

Founder and CEO

CodaSuperhumanGrammarly

You need more than a good product to scale – you need strong rituals. All companies have rituals, from holding all-hands meetings to measuring KPIs. The right rituals in the right places help build your culture, cohere your team, and home in on your targets. The wrong ones can lead you horribly astray. Shishir Mehrotra, former head of YouTube and co-founder of Coda, learned this when he scaled YouTube to a billion hours of watch time each day. He kept the team focused on that audacious goal by establishing fresh new rituals. And in his new role as CEO and founder of Coda, he's learned to constantly ask: What old rituals are holding us back? And what new rituals can we create together that will be inclusive, empowering — and keep us all moving forward? Cameo appearances: George Kembel (Stanford's d.School), Tobi Lütke (Shopify), and Dr. Akhila Cadet (Change Cadet). Read more about the rituals at Coda — and add your own here: https://coda.io/@shishir/masters-of-scale-rituals Read a transcript of this episode at https://mastersofscale.com Subscribe to the Masters of Scale weekly newsletter at https://mastersofscale.com/subscribe See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Shishir Mehrotra

Founder and CEO

CodaSuperhumanGrammarly

My guest today is Shishir Mehrotra and the topic of our conversation is the bundle: offering access to multiple products, services, or providers for a single bundled price. This topic is full of incorrect pre-conceived notions, and as it turns out, the bundle is one of the most powerful ideas in business. Properly harnessed it is good for everyone involved. Shishir explains the ins and outs of bundles in this conversation. Shishir ran product at YouTube for years and sits on the Spotify board of directors. He founded and now leads Coda (which is “A Doc” spelled backwards) in 2014, to bundle together productivity apps like docs, spreadsheets, databases, and applications. I love this wonky, detailed conversation which has me thinking differently about many businesses and business strategy. Please enjoy.   This episode is brought to by Koyfin.   For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (2:08) – (First question) – The arc of his career (3:32) – Why he has an interest in bundling (7:45) – The concepts of superfan, casualfan, and nonfan businesses (11:05) – Using Spotify as an example of bundles (13:24) – The first myth of bundling: Bundling is bad for consumers (17:53) – The second myth of bundling: 1st vs 3rd party providers and the bundlers (23:03) – Low usage but high Marginal Churn Contribution (MCC) business (24:26) – How insurance fits into these models   (26:37) – Myth 3 of bundling: How this impacts consumers (32:12) – How marginal costs play into the thinking of bundling (34:54) – Myth 4: Bundling things that have nothing to do with each other (39:51) – How bundling companies can apply this into their product development (43:21) – Strategic advice to companies building bundles (49:01) – How price and pricing power play into advantages for certain bundlers (54:16) – How does bundling play into his investing thesis (56:47) – Most interesting bundles he’s observed             (58:44) – Eigenquestions: The Art of Framing Problems (59:14) – What the future of this trend is (1:02:24) – What is an eigenquestion (1:06:29) – Kindest thing anyone has done for him   Learn More For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

Shishir Mehrotra

Founder and CEO

CodaSuperhumanGrammarly

Isn't having a vision just fluff? Doesn't every business need to start with the practical realities first? Max Lytvyn doesn't think so. In this episode he tells the story behind how he and his cofounder started with nothing but a vision, and used that to bootstrap Grammarly into a massively profitable business with hundreds of employees. Transcript, speaker information, and more: https://www.indiehackers.com/podcast/045-max-lytvyn-of-grammarly

Max Lytvyn

Co-Founder and Head of Revenue

Grammarly

Hiring a VP of Product -- especially as the founder of the company -- can almost feel like handing over your baby to someone else to hold, observes a16z executive talent team partner Caroline Horn, who hosted an event on this topic earlier this year (which this podcast is based on). Featuring Vijay Balasubramaniyan, founder/CEO of Pindrop; Shishir Mehrotra, founder and CEO of Coda; Gokul Rajaram, Production Engineering Lead at Square; and Alan Schaaf, founder/CEO of Imgur -- and moderated by general partner Martin Casado -- the discussion covers everything from what the VP of Product role really is to how to hire and integrate it into your company. Because if you're going to be handing your "baby" over... how can you avoid common pitfalls? And know that you pick the right person for the job? Stay Updated: Find a16z on YouTube: YouTube Find a16z on X Find a16z on LinkedIn Listen to the a16z Show on Spotify Listen to the a16z Show on Apple Podcasts Follow our host: https://twitter.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Vijay Balasubramaniyan

Co-founder and CEO

Pindrop

Shishir Mehrotra

Founder and CEO

CodaSuperhumanGrammarly

Gokul Rajaram

Production Engineering Lead

SquareDoorDashMAMarathonMMMarathon Management

Alan Schaaf

Founder and CEO

Imgur