Grit

Joubin Mirzadegan

Go-to-market strategy from Kleiner Perkins.

14 episodesWeekly

clips found

episodes analyzed

2.5

clips / episode

Clip categories

founder story (3)Consequences (3)Bold/Contrarian (2)Business Mechanics (2)contrarian take (1)tactical advice (1)

Most discussed topics

ai adoption(1)senior engineers(1)coding tools(1)remote work(1)team building(1)office strategy(1)engineering talent(1)company culture(1)problem solving(1)crypto legislation(1)industry leaders(1)regulatory milestones(1)

Best clip

3:10· 18s· Jeremy Allairefounder story

Circle CEO recalls standing behind the president during historic crypto legislation signing

3:10 / 3:27

The Genius Act is being signed into law at that moment. By the president? By the president. And you're, like, standing right behind him with the with I it looks like Brian Armstrong. Yeah. Yeah. Yeah. Maybe both of the Winklevoss brothers. Yeah. Exactly. Still like now still like Mount Rushmore of Yeah. Yeah. Yeah. Folks in the industry. Yeah.

Full clip page →

Best guests

Dan O

Arvind Jain

James Cadwallader

Ping Wu

Jeremy Allaire

Top clips

Grit · Arvind Jain

tactical advice

Why Glean's CEO refused to split his team between offices

Glean CEO Arvind Jain explains his decision to avoid having a San Francisco office for an extended period. He emphasizes that keeping the entire team co-located was crucial, noting that even his technical leaders and managers who lived in SF opposed the idea of splitting the team across multiple locations.

6:18 - 6:4225s

remote-work team-building office-strategy

Grit · Arvind Jain

founder story

CEO panicked when his company hit 1,000 - here's why

Glean CEO Arvind Jain reveals his unexpected reaction to reaching a major company milestone - panic instead of celebration. He explains the counterintuitive mindset that drives successful entrepreneurs when hitting significant growth numbers.

7:48 - 8:0618s

founder-mindset growth-milestones startup-psychology

Grit

Bold/Contrarian

I don't think Google had any idea then. Otherwise, they probably wouldn't have given it away. Would it have blown up like this if it's been a secret? Would Google have created the ChatGPT moment?

This is a provocative counterfactual about one of tech's biggest strategic mistakes - Google giving away the Transformer architecture that enabled OpenAI's dominance. The hook questions whether AI would have exploded without open access, challenging the narrative of inevitable progress.

24:03 - 24:2219s

Grit · James Cadwallader

Business Mechanics

Building a demo and building a v one becomes really, really trivial, but the real value in these things isn't going deep. The real value is understanding where the nuances of the product and where kind of the nooks and crevices of what makes it truly exceptional are.

Explains a key business insight about AI development - demos are easy but depth is hard. The contrast between 'trivial' demos and 'nooks and crevices' of excellence provides actionable insight for builders and investors.

27:32 - 27:5422s

Grit · Ping Wu

founder story

Why great engineers join startups: it's not just about solving hard problems

Cresta CEO Ping Wu explains what attracts top engineering talent to his company. He argues that the best engineers are drawn to solving difficult technical challenges that also drive real customer value and ROI, rather than just building technology for technology's sake.

3:04 - 3:4238s

engineering-talent company-culture problem-solving

Grit · Arvind Jain

contrarian take

Why senior engineers aren't using AI as much as you think

Glean CEO Arvind Jain explains why many top engineers haven't fully adopted AI tools yet. He argues that while AI excels at writing new code, senior engineers spend most of their time on higher-level work that goes beyond just coding new lines.

43:25 - 43:4419s

ai-adoption senior-engineers coding-tools

Grit

Domain Expertise

Most of the data we produce, if you were to read it, you could lock me in jail for thirty days and ask me to solve one of these physics problems. I can't even barely read the type of data that we create because it's really experts in PhDs.

Vivid metaphor about the complexity of AI training data that makes technical concepts accessible. The 'lock me in jail for 30 days' imagery is memorable and the self-deprecating admission creates relatability while highlighting expertise gaps.

23:23 - 23:3917s

Grit · James Cadwallader

Consequences

You can imagine a world where, hey. Like, you just chat with a thing and the thing does it for you, and you don't really care what that software looks like on the back end. And then that opens up a really interesting playing field for, again, startups and incumbents to kinda reinvent themselves and then capture a broader opportunity.

Paints a vivid picture of the future of software interaction - conversational interfaces abstracting away complexity. The downstream implications for both startups and incumbents make this a compelling business insight that's easy to visualize.

30:12 - 30:3422s

Grit

Consequences

If the AI crawlers go crawl the web and get all the content, when you go to your Perplexity or ChatGPT, do you go back and look at the original source? No. You just read it right there. The original source isn't getting compensated.

Identifies a fundamental business model disruption in clear, accessible terms. The rhetorical question format engages viewers while highlighting an economic consequence most users haven't considered.

30:05 - 30:4035s

Grit · Dan O

Business Mechanics

Matilde and I catch up on a weekly basis, but trust me wholeheartedly and always tells me, like, make decisions that are gonna energize yourself. She constantly tells me that... It's actually a pretty small board.

Reveals the rare functional founder-CEO dynamic with specific advice ('make decisions that energize yourself') and concrete board structure (4 people total). Offers practical insight into how successful transitions actually work.

7:12 - 7:4230s

Grit · Dan O

Practical Framework

I go back to the deathbed conversation that I'm like, I'm gonna sit there and I'm gonna have, like, these parsing thoughts... what are all the things that I didn't get to do?

The 'deathbed conversation' framing provides a stark mental model for prioritizing life decisions. The philosophical approach to goal-setting and regret avoidance offers a framework others can apply to their own ambitious pursuits.

34:46 - 35:1023s

Grit

Bold/Contrarian

Would the academic community have created a different architecture under a different name that looked very similar and felt very similar? Maybe Google had its proprietary transformer model, which nobody could use because it was IP and it didn't become very popular.

Counterfactual speculation about alternative AI timelines that challenges the narrative of Google's mistake. The contrast between open vs proprietary development models resonates with current tech debates about open source AI.

24:25 - 24:4520s

Grit · Dan O

Origin Story

The last thing I wanna do is come across as a person that's, like, outsourcing the help as opposed to, like, being there... You're doing Anna was always, like, you're doing a great job. Like, you really think I'm doing a good job?

Vulnerable admission about parenting insecurity and seeking validation creates authentic human moment. The specific dialogue with his partner about performance anxiety resonates with anyone balancing demanding roles and personal relationships.

43:32 - 44:0634s

Grit

Consequences

We've never seen dollars spent like this. What if they're wrong? What if this is maybe not even enough investment? What if Microsoft decided not to do it, and Meta and Amazon did? They missed the whole thing.

Series of escalating 'what if' questions that capture the high-stakes nature of AI investment. The contrast between 'never seen dollars like this' and 'what if it's not enough' creates tension that drives engagement.

8:51 - 9:0716s

Most clip-worthy episode

The Grittiest Conversations of 2025: AI, Business & Beyond

Dec 29, 20255 clips

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Grit

Clip categories

Most discussed topics

Best clip

Circle CEO recalls standing behind the president during historic crypto legislation signing

Transcript

Best guests

Top clips

Why Glean's CEO refused to split his team between offices

CEO panicked when his company hit 1,000 - here's why

I don't think Google had any idea then. Otherwise, they probably wouldn't have given it away. Would it have blown up like this if it's been a secret? Would Google have created the ChatGPT moment?

Building a demo and building a v one becomes really, really trivial, but the real value in these things isn't going deep. The real value is understanding where the nuances of the product and where kind of the nooks and crevices of what makes it truly exceptional are.

Why great engineers join startups: it's not just about solving hard problems

Why senior engineers aren't using AI as much as you think

Most of the data we produce, if you were to read it, you could lock me in jail for thirty days and ask me to solve one of these physics problems. I can't even barely read the type of data that we create because it's really experts in PhDs.

If the AI crawlers go crawl the web and get all the content, when you go to your Perplexity or ChatGPT, do you go back and look at the original source? No. You just read it right there. The original source isn't getting compensated.

Matilde and I catch up on a weekly basis, but trust me wholeheartedly and always tells me, like, make decisions that are gonna energize yourself. She constantly tells me that... It's actually a pretty small board.

I go back to the deathbed conversation that I'm like, I'm gonna sit there and I'm gonna have, like, these parsing thoughts... what are all the things that I didn't get to do?

Would the academic community have created a different architecture under a different name that looked very similar and felt very similar? Maybe Google had its proprietary transformer model, which nobody could use because it was IP and it didn't become very popular.

The last thing I wanna do is come across as a person that's, like, outsourcing the help as opposed to, like, being there... You're doing Anna was always, like, you're doing a great job. Like, you really think I'm doing a good job?

We've never seen dollars spent like this. What if they're wrong? What if this is maybe not even enough investment? What if Microsoft decided not to do it, and Meta and Amazon did? They missed the whole thing.

Most clip-worthy episode

The Grittiest Conversations of 2025: AI, Business & Beyond

Recent episodes

How Sierra Is Pulling Ahead in the AI Race | Co-founder Bret Taylor

The AI Era of Cybercrime: How Malwarebytes Is Evolving Its Security Stack | Marcin Kleczynski

The Truth Behind Automation Claims in Customer Support | Cresta CEO Ping Wu

The Safest Dollar on the Internet | Circle CEO Jeremy Allaire

Why We’re Only Using 1% of AI | Glean CEO Arvind Jain

The Grittiest Conversations of 2025: AI, Business & Beyond

How Brands Stay Visible When AI Decides | Profound CEO James Cadwallader

How Snap Plans to Win the AR Race | Evan Spiegel on Spectacles

The Pull to Build: Joubin Mirzadegan on Grit and Starting Roadrunner

Building Cloudflare for the Next 50 Years | Co-founder Cloudfare Michelle Zatlyn

She Sold Her Startup for $500 Million, Here’s Her Next Idea

Synthetic Data and the Future of AI | Cohere CEO Aidan Gomez

From Yext to Roam: Howard Lerman’s Second Act

Rebuilding Front for the AI Era | CEO Dan O’Connell

From the blog