Knuckle Up with Nakul

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 principleReferenced:• Billie Jean King• Black Swan Farming• Brian Chesky• Cursor• Founder Mode• Ivan Zhao• Model Context Protocol (MCP)• Nat Friedman• Paul Graham• Peter Principle• Seeing Like a State• TwilioWhere to find Michael Grinich:• WorkOS• X• LinkedInWhere to find Nakul Mandan:• Audacious Ventures• X• LinkedInWhere to find Audacious:• Website• LinkedInTimestamps:00:00 Introduction01:33 From design-obsessed founder to enterprise infrastructure04:20 Michael’s year off and what made the WorkOS bet obvious06:54 Why a great startup idea has to look bad first09:46 Minimum awesome product beats MVP11:09 The org with no CRO, no VP of sales, and one PM13:29 Hiring for curiosity, not credentials16:25 The "AI pilled" interview red flag18:25 A week is 2% of the year26:00 How WorkOS approaches brand33:00 The future shape of engineering orgs43:20 Why senior engineers benefit most from AI44:45 Micro-leadership over micromanagement49:10 Tough times in the early days59:04 The reverse Peter principle1:04:38 Quickfire: red flags, hires too early, and biggest fears1:10:30 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

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 uncertaintyReferenced:• Bhagavad Gita• Jiddu Krishnamurti• Qasar Younis• Upanishads• Viktor FranklWhere to find Bipul:• Rubrik• X• LinkedInWhere to find Nakul:• Audacious Ventures• X• LinkedInWhere to find Audacious:• Website• X• LinkedInTimestamps:00:00 Intro01:47 State of intellect vs state of will03:09 Bipul’s maniacal recruiting philosophy07:06 Recruiting is like starting a religion11:44 Will vs skill: you can teach one but not the other14:28 Adhogāmī: fighting mental downward slopes16:03 Why Bipul thinks product market fit is dead19:25 Nobody knows anything (and what that means for you)23:06 Three questions that launched Rubrik’s AI transformation32:04 “Either you go AI or you die”33:42 There is only one moat35:15 When Rubrik’s growth collapsed overnight41:28 “Maximal Thinking”: How to succeed amidst uncertainty45:12 Quickfire round: red flags, worst VC advice, more47:29 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

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 intentionalityReferenced:* Andrej Karpathy* Applied Intuition* Immad Akhund* Kickstarter* Peter Ludwig* 18 Mistakes That Kill StartupsWhere to find Qasar:* Website* Twitter / X* LinkedIn* Applied IntuitionWhere to find Nakul:* Twitter / X* LinkedInWhere to find Audacious Ventures:* Website* Twitter / X* LinkedInTimestamps:00:00 Intro01:19 What really makes someone a founder05:26 The company that almost became Kickstarter08:12 The most common misread on feedback13:40 Why most founders don’t end up with the best team19:45 How to pick a co-founder23:38 Your first 10 hires are really your first 10028:21 The case for hiring slow and firing slow33:22 Red, yellow, green: how Applied gives monthly feedback35:00 The role that knows what’s actually going on in a company40:01 How to operate with speed and intentionality42:41 The three things Qasar spends time on45:57 How Applied is driving AI adoption52:06 The type of engineer Applied is now looking for1:01:19 Why this could be the golden age of small companies1:09:13 Quickfire: red flags, overrated advice, and superpowers1:12:32 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

Frank Slootman is the only CEO in history to take three enterprise companies public: Data Domain, ServiceNow, and Snowflake. At their peak, the companies he led were worth over $200 billion combined. His playbook for building high-performance organizations, captured in his book “Amp It Up”, has become required reading for CEOs. In this conversation, Frank opens up about the fear of failure that shaped his early career, why most CEOs tolerate mediocrity for far too long, and the moment he realized Snowflake needed a different kind of leader and chose to step aside.We discuss:• Why being a CEO is a confrontational job• The “drivers vs. passengers” framework• Why references matter more than interviews• Why culture isn’t about making people feel good• How Frank faces his demons “for breakfast”• How Data Domain survived year one on $3M and a product nobody believed in• Why AI is a dislocation on the scale of the Industrial RevolutionReferenced:• Amp It Up• Data Domain• Elon Musk• Google• Intel• Peter Thiel• Scott McNealy• ServiceNow• Snowflake• Sridhar Ramaswamy• Steve JobsWhere to find Frank:• LinkedInWhere to find Nakul:• Twitter / X• LinkedInWhere to find Audacious Ventures:• Website• Twitter / X• LinkedInTimestamps:00:49 Introduction01:21 Why being a CEO is a confrontational job03:51 Great people are hungry for hard feedback08:19 Psychographic profiling: how Frank builds compatible teams09:52 Drivers vs passengers: how to tell the difference12:39 Why back-channel references beat interviews every time16:19 “When there’s doubt, there’s no doubt”20:42 Inside Frank’s Tuesday operating cadence22:27 The “go direct” rule that breaks org chart politics26:19 Why bigger goals force better plans31:27 Standards are the real culture38:17 The email Frank wrote every Monday for years41:35 Advice for navigating today’s volatility47:25 Facing demons for breakfast at Data Domain54:19 Why Frank fired himself as Snowflake CEO1:05:19 Coming to Silicon Valley “10 years late”1:07:59 Why AI is an industrial-revolution-scale shift1:10:01 Frank’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