$50M ARR With 3 sales reps, no CRO, and one PM | Michael Grinich (CEO, WorkOS)

Business used to be go karting. Now it's Formula 1.

Akshay Kothari has spent most of his time at Notion trying to put himself out of a job. His move, repeated for years, is to run at whatever the company's biggest unsolved problem is, build the system around it, hire someone great to own it, and then remove himself. In 2023 the approach left him, a co-founder of a multibillion-dollar company, with zero direct reports and a calendar wide open to think. That instinct fits the company he helps run. Notion built itself like an art project: profitable, still largely owned by its founders and employees, raising money only when there was a real reason to, and kept deliberately small, around 1,200 people running a business at public scale. For years its core was a system of record, a modern editor and database that people genuinely loved and built their work inside. Then AI changed what people expect software to do, and Notion decided to reinvent the product rather than wait to be replaced. In this conversation, Akshay walks through how Notion pulled that off: the stretch he calls the swamp of despair, when its AI agent failed four times before it worked; why the company stopped trying to make the model fit its product and started fitting the product to the model; and how it dissolved the line between its AI team and everyone else until there was nobody left who wasn't building with AI. The bet landed. AI moved from a defensive play to a real driver of growth, and Notion's growth rate has climbed for over a year, with the most recent quarter running about 50% above where it was a year earlier. As Akshay frames it, the business went from go-karting to Formula 1, and now the company has to rewire how it drives. Listen on... • Spotify: https://open.spotify.com/show/5KorHDryscDzLwPkWEgAH1 [https://open.spotify.com/show/5KorHDryscDzLwPkWEgAH1] • Apple Podcasts: https://podcasts.apple.com/us/podcast/knuckle-up-with-nakul/id1893213920 [https://podcasts.apple.com/us/podcast/knuckle-up-with-nakul/id1893213920] Akshay Kothari is the co-founder and chief operating officer of Notion, where he has built and scaled functions from support and sales to marketing and finance, alongside co-founders Ivan Zhao (CEO) and Simon Last. Before Notion, he co-founded Pulse, a news-reading app that won an Apple Design Award, reached 30 million users, and was acquired by LinkedIn for $90 million in 2013. Where to find Akshay Kothari... • Notion: https://www.notion.com/ [https://www.notion.com/] • X: https://x.com/akothari [https://x.com/akothari] • LinkedIn: https://www.linkedin.com/in/akothari [https://www.linkedin.com/in/akothari] Where to find Nakul... • Audacious Ventures: https://www.audacious.co/ [https://www.audacious.co/] • X: https://x.com/nakul [https://x.com/nakul] • LinkedIn: https://www.linkedin.com/in/nakulmandan/ [https://www.linkedin.com/in/nakulmandan/] Where to find Audacious Ventures... • Website: https://www.audacious.co/ [https://www.audacious.co/] • LinkedIn: https://www.linkedin.com/company/audaciousventures/ [https://www.linkedin.com/company/audaciousventures/] In this conversation with Akshay Kothari... 00:00 Who is Akshay Kothari? 01:27 What were Notion's core founding principles? 06:20 Which early cultural principles scaled, and which broke? 08:22 How did Notion hire its first employees, and where did they come from? 11:48 How does hiring work now that the founders can't meet everyone? 14:35 Why does Akshay, as COO, prefer to have zero direct reports? 19:05 How do Ivan, Simon, and Akshay divide the work? 21:07 Does Notion's intentionality ever conflict with speed? 25:25 What should other founders steal from Notion's culture? 28:11 When did AI become a reason to rethink the whole product? 30:44 Why were the early AI years a "swamp of despair"? 36:05 How do you push AI across a huge product without losing the user? 39:25 Does Notion buy its AI DNA or build it? 40:44 Should Notion be afraid of OpenAI, Anthropic, and fast copycats? 46:58 What's hardest about the reinvention, and what does "meet the LLM" mean? 52:42 Is Notion AI-native in every function yet? 54:36 Are Notion's engineers still writing code, and how has engineering changed? 1:01:07 Once building is cheap, what's the new bottleneck? 1:02:39 How is AI reshaping sales, marketing, and support? 1:09:07 How many agents run inside Notion, and who builds them? 1:11:28 How has recruiting changed for the AI era? 1:13:48 What still worries Akshay about Notion's future? 1:15:22 Quickfire: admired founders, books, overrated AI advice, and Akshay’s superpower 1:19:42 What should a $50M pre-AI company do in the next 90 days? Akshay's sharpest lines from this conversation... On putting himself out of a job: "Ivan calls me a stem cell. I go there and build something, then I get out of it." On meeting the model where it is: "You really have to stop trying to fit the LLM with what you have, and you have to fit what you have to the other." On what AI is really for: "The best companies are just raising their ambitions. It's less about efficiency and more about, can each person be way more productive?" On just how much AI changed business: "We cannot take the way we were go-karting and apply it to Formula One." On disrupting yourself before the market does: "You have to disrupt yourself to where the business is going. You can kind of do it to yourself before someone else does it to you." This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.knuckleup.co [https://www.knuckleup.co?utm_medium=podcast&utm_campaign=CTA_1]

Behind the curtain of a $4.5b AI-native powerhouse

Ashwin Sreenivas spent his childhood in India waking up at 5am and studying until 8:30 at night. History, geography, physics, chemistry, math. Every day, from 4th grade through 12th grade, through the Olympiads and the National Talent Search Exam. He says now, three years into building one of the more successful post-ChatGPT companies in the world, that all of that is precisely why what he does today feels almost easy. "I get to come in here and there's a lot of people and I'm having fun." That mode is what Decagon runs on. The company Ashwin co-founded with Jesse Zhang in 2023 is now valued at $4.5 billion, has crossed 450 employees in three years, and works with some of the largest enterprises on the planet. The path there has in some ways been simple: don't theorize about where AI is going, talk to customers until the pain is unmistakable, build for that, ship, repeat. Decagon went from zero to $1 million in ARR with two co-founders and no employees. In this conversation, Ashwin walks through what that means in practice. How Decagon operationalizes a single cultural priority: speed, even when it costs coordination. How they hire 450 people without breaking the bar. How AI has reshaped the IC engineer, the AE, and the VP of EPD. And why, after a year of running 6+ days a week, the thing he and Jesse would tell their earlier selves is: go faster. Ashwin Sreenivas is the co-founder and CTO of Decagon, the AI customer concierge platform founded in 2023 that serves enterprise customers including Substack, Eventbrite, Duolingo, and Notion and is valued at $4.5 billion. Decagon Labs, the company's in-house model development effort, now powers around 90% of Decagon's model traffic. Before Decagon, Sreenivas co-founded Helia in 2019, an AI startup acquired by Scale AI a year later. He started his career as a strategist at Palantir Technologies in New York. Sreenivas holds a Bachelor's degree (2017) and Master's degree (2019) in Computer Science from Stanford University. Decagon raised $35M in 2024 and has scaled to over 450 employees. Where to find Ashwin Sreenivas: • Decagon [https://decagon.ai/] • X [https://x.com/AshwinSreenivas] • LinkedIn [https://www.linkedin.com/in/sreenivasashwin/] Where to find Nakul: • Audacious Ventures [https://www.audacious.co/] • X [https://x.com/nakul] • LinkedIn [https://www.linkedin.com/in/nakulmandan/] Where to find Audacious Ventures: • Website [https://www.audacious.co/] • LinkedIn [https://www.linkedin.com/company/audaciousventures/] In this conversation with Ashwin Sreenivas: 00:00 Who is Ashwin Sreenivas? 02:10 How did Jesse and Ashwin decide what to work on at Decagon? 04:19 Why did they reject the top-down market-sizing approach? 13:16 What does Decagon give up to keep moving fast? 17:54 Does Decagon expect their team to be 6-days in-office? 23:33 Why didn't they hire a single employee until $1M in ARR? 27:12 How do you hire 450 people in three years without breaking the bar? 31:20 Are Decagon engineers even writing code anymore? 35:08 How does the IC engineer role change with Claude Code and Cursor? 36:32 Shipping in two days: how does EPD leadership change? 40:15 What are the two types of FDE, and which one do most AI companies actually need? 49:21 How will the human role at Decagon evolve over three years? 57:15 Why did Decagon build its own models in Decagon Labs? 1:00:50 What worries Ashwin most about Decagon today? 1:03:52 How does Ashwin manage his psyche while running this fast? 1:08:00 What hiccups has Decagon had that no one sees from the outside? 1:09:50 Quickfire: overrated advice, AI products, books, red flags 1:12:43 What would Ashwin tell his younger self about Decagon's journey? Ashwin's sharpest lines from this conversation... On what actually matters: "If you build a company doing something that your customers care about, you can mess up everything else in a way and it doesn't really matter." On founder market fit: "If you pick the right market, the market will pull the problem and product out of the founding team." On what Decagon traded for speed: "The pace of building has changed so quickly. With AI, there isn't that much time for coordination. You have to give somewhere, and we gave for speed." On packing desks tight: "I specifically asked our head of workplace to get smaller desks so that people are packed even closer together, so that you can lean over and talk to an exponentially larger number of people." On responsibility for AI-generated code: "Use all the tools you have available so that you can move faster, but at the end of the day, you are responsible for the code you push and you should be prepared to defend it rather than say, 'oh, the AI agent wrote it.'" On hiring red flags: "It's not a specific flag, but rather that gut feeling of something's a little off and I'm not sure I want to pull the trigger on this." On the normality of “fires”: "I guarantee you every fast-growing company, probably without a single exception, they've had a thousand fires internally. Just normal. That's just how it is." On the advice he’d give his younger self: "Go faster, hire faster, build faster, get out to the biggest customers faster because the need is real, the market pull is real. You just need to go capture as much of it as quickly as you can." This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.knuckleup.co [https://www.knuckleup.co?utm_medium=podcast&utm_campaign=CTA_1]

$50M ARR With 3 sales reps, no CRO, and one PM | Michael Grinich (CEO, WorkOS)

Michael Grinich is a design-obsessed engineer who once spent days in a recording studio with an electronic musician crafting the perfect email notification sound. He now runs WorkOS, the $50M (accelerating) ARR enterprise infrastructure business powering nearly every major AI company you can think of, OpenAI, xAI, Anthropic, Sierra, Cursor. Michael has scaled the seven-year-old company to 100 people with no CRO, no VP of sales, and just three sales reps. In an industry where most CEOs default to hiring more executives, Michael runs WorkOS with senior ICs and a weekly operating cycle. In this episode, he unpacks the philosophy behind it all. We also discuss: • Why a great startup idea has to look bad first • Why Michael subscribes to "Minimum awesome product" over MVP • Micro-leadership over micromanagement • How to "AI pill" your team • Why senior engineers are the most impactful with AI • The reverse Peter principle Referenced: • Billie Jean King [https://en.wikipedia.org/wiki/Billie_Jean_King] • Black Swan Farming [https://paulgraham.com/swan.html] • Brian Chesky [https://www.linkedin.com/in/brianchesky/] • Cursor [https://www.cursor.com/] • Founder Mode [https://paulgraham.com/foundermode.html] • Ivan Zhao [https://www.linkedin.com/in/ivanhzhao/] • Model Context Protocol [https://modelcontextprotocol.io/] (MCP) • Nat Friedman [https://nat.org/] • Paul Graham [https://paulgraham.com/] • Peter Principle [https://en.wikipedia.org/wiki/Peter_principle] • Seeing Like a State [https://yalebooks.yale.edu/book/9780300078152/seeing-like-a-state/] • Twilio [https://www.twilio.com/] Where to find Michael Grinich: • WorkOS [https://workos.com/] • X [https://x.com/grinich] • LinkedIn [https://www.linkedin.com/in/grinich/] Where to find Nakul Mandan: • Audacious Ventures [https://www.audacious.co/] • X [https://x.com/nakul] • LinkedIn [https://www.linkedin.com/in/nakulmandan/] Where to find Audacious: • Website [https://www.audacious.co/] • LinkedIn [https://www.linkedin.com/company/audaciousventures/] Timestamps: 00:00 Introduction 01:33 From design-obsessed founder to enterprise infrastructure 04:20 Michael’s year off and what made the WorkOS bet obvious 06:54 Why a great startup idea has to look bad first 09:46 Minimum awesome product beats MVP 11:09 The org with no CRO, no VP of sales, and one PM 13:29 Hiring for curiosity, not credentials 16:25 The "AI pilled" interview red flag 18:25 A week is 2% of the year 26:00 How WorkOS approaches brand 33:00 The future shape of engineering orgs 43:20 Why senior engineers benefit most from AI 44:45 Micro-leadership over micromanagement 49:10 Tough times in the early days 59:04 The reverse Peter principle 1:04:38 Quickfire: red flags, hires too early, and biggest fears 1:10:30 Michael's advice to their 25-year-old self This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.knuckleup.co [https://www.knuckleup.co?utm_medium=podcast&utm_campaign=CTA_1]

Nobody knows anything, product market fit is dead, and there's only one moat | Bipul Sinha

Bipul Sinha grew up in dire circumstances in India, made his way to IIT, and immigrated to the US in search of the American dream. By 40 he had become a successful VC at Lightspeed; he then founded Rubrik, today a $10 billion public company and one of the last decade's fastest-growing enterprise software businesses. Most founders look to mentors for guidance. Bipul's first principle is "nobody knows anything." In this conversation, he shares the mental models that got him here and how he's rebuilding Rubrik for the AI era. We also discuss: • The "state of intellect vs state of will" mindset shift • Why "recruiting is like starting a religion" • "Nobody knows anything" and how to use experts expertly • "Product market fit is dead" and the S-curve stack • "Adhogāmī": only work on what worries you most • Why time is the only real moat • The "Maximal thinking" framework for dealing with uncertainty Referenced: • Bhagavad Gita [https://en.wikipedia.org/wiki/Bhagavad_Gita] • Jiddu Krishnamurti [https://en.wikipedia.org/wiki/Jiddu_Krishnamurti] • Qasar Younis [https://www.linkedin.com/in/qasar/] • Upanishads [https://en.wikipedia.org/wiki/Upanishads] • Viktor Frankl [https://en.wikipedia.org/wiki/Viktor_Frankl] Where to find Bipul: • Rubrik [https://www.rubrik.com/] • X [https://x.com/bipulsinha] • LinkedIn [https://www.linkedin.com/in/bipulsinha/] Where to find Nakul: • Audacious Ventures [https://www.audacious.co/] • X [https://x.com/nakulmandan] • LinkedIn [https://www.linkedin.com/in/nakulmandan/] Where to find Audacious: • Website [https://www.audacious.co/] • X [https://x.com/audaciousVC] • LinkedIn [https://www.linkedin.com/company/audaciousventures/] Timestamps: 00:00 Intro 01:47 State of intellect vs state of will 03:09 Bipul’s maniacal recruiting philosophy 07:06 Recruiting is like starting a religion 11:44 Will vs skill: you can teach one but not the other 14:28 Adhogāmī: fighting mental downward slopes 16:03 Why Bipul thinks product market fit is dead 19:25 Nobody knows anything (and what that means for you) 23:06 Three questions that launched Rubrik’s AI transformation 32:04 “Either you go AI or you die” 33:42 There is only one moat 35:15 When Rubrik’s growth collapsed overnight 41:28 “Maximal Thinking”: How to succeed amidst uncertainty 45:12 Quickfire round: red flags, worst VC advice, more 47:29 Bipul’s advice to his 25-year-old self This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.knuckleup.co [https://www.knuckleup.co?utm_medium=podcast&utm_campaign=CTA_1]

Battle-tested playbooks for recuriting, reading the market, and adapting to AI

Qasar Younis grew up on a farm in Pakistan, moved to Detroit as a kid, and worked at General Motors before landing at Google and becoming COO of Y Combinator. He then founded Applied Intuition, today a $15 billion company building AI for the physical world. In an industry where most people look up to tech founders, Qasar looks up to Sam Walton and Warren Buffett. Qasar is an N of 1 founder, and in this conversation, he shares his contrarian approach to company building. We discuss: * What truly makes a founder * The “two exceptional indicators” recruiting bar * Why Qasar’s first 10 hires lived in a house together * A simple framework for monthly performance reviews * The “golden age of small companies” * How to operate with speed and intentionality Referenced: * Andrej Karpathy [https://karpathy.ai/] * Applied Intuition [https://www.appliedintuition.com/] * Immad Akhund [https://www.linkedin.com/in/iakhund/] * Kickstarter [https://www.kickstarter.com/] * Peter Ludwig [https://www.linkedin.com/in/peterwludwig/] * 18 Mistakes That Kill Startups [http://www.paulgraham.com/startupmistakes.html] Where to find Qasar: * Website [https://qy.co/] * Twitter / X [https://x.com/qasar] * LinkedIn [https://www.linkedin.com/in/qasar/] * Applied Intuition [https://www.appliedintuition.com/] Where to find Nakul: * Twitter / X [https://x.com/nakul] * LinkedIn [https://www.linkedin.com/in/nakulmandan/] Where to find Audacious Ventures: * Website [https://www.audacious.co/] * Twitter / X [https://x.com/AudaciousHQ] * LinkedIn [https://www.linkedin.com/company/audaciousventures/] Timestamps: 00:00 Intro 01:19 What really makes someone a founder 05:26 The company that almost became Kickstarter 08:12 The most common misread on feedback 13:40 Why most founders don’t end up with the best team 19:45 How to pick a co-founder 23:38 Your first 10 hires are really your first 100 28:21 The case for hiring slow and firing slow 33:22 Red, yellow, green: how Applied gives monthly feedback 35:00 The role that knows what’s actually going on in a company 40:01 How to operate with speed and intentionality 42:41 The three things Qasar spends time on 45:57 How Applied is driving AI adoption 52:06 The type of engineer Applied is now looking for 1:01:19 Why this could be the golden age of small companies 1:09:13 Quickfire: red flags, overrated advice, and superpowers 1:12:32 Qasar’s advice to his 25-year-old self This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.knuckleup.co [https://www.knuckleup.co?utm_medium=podcast&utm_campaign=CTA_1]