Grit

Inside the AI Startup Making Customer Support 65% Cheaper

How do you keep up when you go from 50 to 500 employees in a year? Jesse Zhang shares how Decagon scaled that quickly, from hiring ahead of demand to keeping the company connected as the team grows. He also explains why the zero-to-one phase is so different from scaling, and how Decagon found its way out of the idea maze in just three weeks. Guest: Jesse Zhang, Co-founder and CEO, Decagon Connect with Jesse Zhang X LinkedIn Connect with Joubin: X LinkedIn Email: grit@kleinerperkins.com Follow Grit on LinkedIn X ​Learn more about Kleiner Perkins

The AI Race Has a Leaderboard | Arena CEO Anastasios Angelopoulos

AI could be bigger than electricity. Anastasios Angelopoulos is seeing that shift firsthand, with Arena ranking 500+ models and tracking roughly 10 new releases every week. On Grit, he explains why there may never be one dominant AI model and why the API layer may be less sticky than people think. Guest: Anastasios Angelopoulos, Co-Founder and CEO of Arena Connect with Anastasios Angelopoulos X LinkedIn Connect with Mamoon X LinkedIn Connect with Joubin: X LinkedIn Email: grit@kleinerperkins.com Follow Grit: LinkedIn X ​Learn more about Kleiner Perkins

Data Centers in Orbit by 2028: Baiju Bhatt on His Plans After Robinhood

What kind of founder walks away from a multi-billion-dollar fintech company to start building rockets? Baiju Bhatt, co-founder of Robinhood, joins Joubin Mirzadegan to talk about life after one of the most consequential companies in modern finance, and why he's now betting on Cowboy Space Corporation, an orbital infrastructure company building AI data centers that ride to space inside its own rockets. "I still have that dog in me," he says. Baiju opens up about building alone for the first time in 15 years and what he learned about product-market fit while scaling Robinhood through its most chaotic years. Connect with Baiju: X LinkedIn Connect with Joubin: X LinkedIn ​ Email: grit@kleinerperkins.com Follow Grit on LinkedIn X ​Learn more about Kleiner Perkins

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Booking.com CEO on AI and the Future of Travel

"Our mission is to make it easier for everybody to experience the world." From the dot-com crash to AI, Glenn Fogel has spent nearly three decades helping Booking Holdings evolve through every major technology shift while staying true to that mission. He also shares with Joubin Mirzadegan why "you're always selling," and how Booking is using AI to amplify what every employee can accomplish. Guest: Glenn Fogel, CEO of Booking Holdings Connect with Glenn LinkedIn Connect with Joubin: X LinkedIn Email: grit@kleinerperkins.com Follow Grit LinkedIn X ​Learn more about Kleiner Perkins

Ex-Twitter CEO on Why AI Needs a New Internet | Parag Agrawal

"The answer to every problem is a model." Parag Agrawal shares the ideas behind Parallel: products that continuously learn, and teams designed around versatile problem solvers. He also shares why he built an AI agent for himself, and why AI's biggest opportunity is expanding what people can achieve. Guest: Parag Agrawal, founder and CEO of Parallel, and former CEO of Twitter Connect with Parag X LinkedIn Connect with Mamoon X LinkedIn Connect with Joubin X LinkedIn Email: grit@kleinerperkins.com Follow Grit on: LinkedIn X ​Learn more about Kleiner Perkins

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The Sales Framework Every Founder Needs | Mark Roberge

"There's 20 fires going on at every moment in the office and you have enough water to put out four." Mark Roberge shares what it takes to build and scale a company, from finding product-market fit to knowing when it's time to grow. He also shares the framework behind his new book, The Science of Selling, and why founders should scale based on their own data, not another company's success. Guest: Mark Roberge, Founding CRO of HubSpot, HBS Professor, and Co-Founder at Stage 2 Capital Connect with Mark: X LinkedIn Connect with Joubin: X LinkedIn Email: grit@kleinerperkins.com Follow Grit on: LinkedIn X ​Learn more about Kleiner Perkins

Airwallex's Jack Zhang on Fintech, Failure, and Growth

In 2020, Airwallex lost nearly half its revenue overnight. Today it's worth $11 billion. Jack Zhang reflects on the decisions that kept the company alive, raising capital during uncertainty, and leading through its toughest chapter. This episode is a candid look at why Jack chose to keep building, even when a $1.2 billion acquisition was on the table. Guest: Jack Zhang, founder and CEO, Airwallex Connect with Jack Zhang X LinkedIn Connect with Joubin X LinkedIn Email: grit@kleinerperkins.com Follow Grit on: LinkedIn X ​Learn more about Kleiner Perkins

Why 80% of the Fortune 100 Chose Qualtrics | Ryan Smith

AI may change software overnight, but company building still takes time. Ryan Smith explains why, despite the pace of AI, “the race is going to be way longer than anyone thinks.” He reflects on Qualtrics surviving multiple market cycles and ultimately being acquired by SAP for $8 billion days before going public. Guest: Ryan Smith, co-founder Qualtrics Connect with Ryan Smith X LinkedIn Connect with Joubin: X LinkedIn Email: grit@kleinerperkins.com Follow Grit: LinkedIn X ​Learn more about Kleiner Perkins

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What It Takes to Build Software for 171,000+ Restaurants | Aman Narang

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 Connect with Toast LinkedIn Instagram X Connect with Joubin: X LinkedIn Email: grit@kleinerperkins.com Follow on LinkedIn Follow on X ​Learn more about Kleiner Perkins

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What It Takes to Build a Generational Company | Anduril’s Trae Stephens

Founder quality becomes more important as startups become easier to build. Trae Stephens, co-founder of Anduril and partner at Founders Fund, has spent years backing founders with strong conviction, including most recently at Roadrunner. He shares why too much capital too early can hurt startups, and why the best companies are built by teams with complementary strengths. Guest: Trae Stephens, co-founder, Anduril and Partner, Founders Fund Connect with Trae Stephens X LinkedIn Connect with Joubin: X LinkedIn Email: grit@kleinerperkins.com Follow Grit on LinkedIn Follow Grit on X ​ Learn more about Kleiner Perkins

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How AIG Is Reinventing Insurance With AI | Peter Zaffino

What does it take to run a company where the business is risk itself? In conversation with Joubin Mirzadegan, Peter Zaffino shares what the role demands at AIG, including high stakes decisions, constant responsibility, and sacrifice. This episode looks at his journey as CEO ahead of his transition to Executive Chairman this June. Leading at a global scale across 200+ countries. Guest: Peter Zaffino Connect with Peter Zaffino LinkedIn Connect with Joubin: X LinkedIn Email: grit@kleinerperkins.com Follow on LinkedIn Follow on X ​Learn more about Kleiner Perkins

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From Airbnb to Linear: How Karri Saarinen Redefined Product Design

In a market that hadn’t changed in decades, Linear didn’t win by being faster. They won by being more thoughtful. Karri Saarinen helped shape design at Airbnb and Coinbase before building Linear around small teams and high standards. On Grit, he shares how Linear is building for a new era of software development. Guest: Karri Saarinen, co-founder and CEO of Linear Connect with Karri Saarinen X LinkedIn Connect with Josh Coyne: X LinkedIn Connect with Joubin: X LinkedIn Email: grit@kleinerperkins.com Follow on LinkedIn Follow on X ​Learn more about Kleiner Perkins

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How Kevin Mandia Built the Most Trusted Name in Cybersecurity

What does security look like when attackers use AI better than you do? Armadin recently raised $200M to build for the “attacker of the future,” where attacks are autonomous and harder to contain. On the Kleiner Perkins Grit podcast, Kevin Mandia joins Joubin Mirzadegan to share how he’s thinking about this shift, why cybersecurity has always been a calling, and why customer trust is what ultimately compounds into market leadership. Guest: Kevin Mandia, Founder and CEO, Armadin Connect with Kevin Mandia LinkedIn: https://www.linkedin.com/in/kevin-mandia-0a07173/ Connect with Josh Coyne: X LinkedIn Connect with Joubin: X LinkedIn Email: grit@kleinerperkins.com Follow on LinkedIn Follow on X ​Learn more about Kleiner Perkins

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The Silicon Valley Insider In The Pentagon | DoW Emil Michael

Emil Michael went from scaling Uber across 600 cities to rewiring the world's largest military. In the midst of the Pentagon-Silicon Valley debate, the now U.S. Under Secretary of Defense for Research and Engineering opens up about what a real partnership demands from both sides. He also shares how he's built three new entry points for defense tech companies, and why America's military is called the "Department of War" again. Guest: Emil Michael, U.S. Under Secretary of Defense for Research and Engineering Connect with Emil Michael X LinkedIn Connect with Joubin X LinkedIn 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

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

Few founders have seen Silicon Valley from every seat at the table. After co-creating Google Maps at Google, serving as CTO at Facebook, and later as co-CEO of Salesforce, Bret Taylor is now building AI agents at Sierra to redefine customer experience. On Grit, he explains why “competitive intensity” is a core value at their fast-growing company and why he believes AI won’t lead to a world where people stop working. Guest: Bret Taylor, co-founder of Sierra Connect with Bret X LinkedIn Connect with Joubin X LinkedIn Email: grit@kleinerperkins.com Follow Grit LinkedIn X ​Learn more about Kleiner Perkins:https://www.kleinerperkins.com/

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

What began as a 14 year old fixing infected computers became Malwarebytes, an 800 person cybersecurity company trusted by millions of customers. On Grit, Marcin Kleczynski joins Joubin Mirzadegan to explore AI driven cyber threats, strategic reinvention, and the discipline of evolving before the market forces you to. “We’ve exceeded. Now, what do we do to protect individuals against the next wave of threats, which are plentiful?” Guest: Marcin Kleczynski, CEO at Malwarebytes Connect with Marcin Kleczynski X: https://x.com/mkleczynski LinkedIn: https://www.linkedin.com/in/marcinkleczynski/ 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/

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

Can you scale customer support without burning out agents or frustrating customers? Ping Wu shares how Cresta combines AI and human intelligence into a single system that scales sustainably for companies like United Airlines and Porsche. In this episode, Ping also breaks down the three constraints that shape automation in the real world: conversation complexity, infrastructure debt, and customer demographics. Guest: Ping Wu, CEO of Cresta Connect with Ping Wu X: https://x.com/ping_wu LinkedIn: https://www.linkedin.com/in/pingwu/ 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/

The Safest Dollar on the Internet | Circle CEO Jeremy Allaire

USDC closed the gap between software and law in modern finance. On Grit, Jeremy Allaire discusses how fully reserved, dollar backed digital currency became part of the financial system after more than a decade of work. He also shares why for him grit is about sustaining belief through deep uncertainty, even when Circle faced the threat of bankruptcy in 2019. Guest: Jeremy Allaire, Co-Founder, Chairman and CEO at Circle ​ Connect with Jeremy Allaire X: https://x.com/jerallaire LinkedIn: https://www.linkedin.com/in/jeremyallaire/ 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/

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

Glean has grown into a $7.2B company by giving employees AI assistants and agents that extend their capabilities. CEO Arvind Jain is back on Grit alongside Joubin Mirzadegan. Here’s what stood out: “My mindset by default is that if you build something last year, that it's got to be obsolete. There has to be a new way to do that thing better today. If not, then it's just lack of imagination.” “I have no doubts that AI capabilities are just going to increase more and more over the next few years. But even more important is this concept of how much are we even leveraging what AI can do today? I would say that we've not even used 1% of current capabilities of these models” “If you're trying to be everything to everyone, then you just cannot compete with somebody who's focused on a smaller problem and going deep into that.” You can also listen to Arvind’s earlier episode here: https://www.youtube.com/watch?v=iIH0Qp6d6bg&list=PLRiWZFltuYPF8A6UGm74K2q29UwU-Kk9k&index=96 Guest: Arvind Jain, founder and CEO, Glean ​ Connect with Arvind Jain X: https://x.com/jainarvind LinkedIn: https://www.linkedin.com/in/jain-arvind/ 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/

The Grittiest Conversations of 2025: AI, Business & Beyond

In this recap episode, we highlight the best moments from our 2025 interviews and reflect on the ideas that defined the year. Featuring: David Rubenstein (co-founder of Carlyle) Yamini Rangan (CEO of HubSpot) Ben Chestnut (co-founder of Mailchimp) Winston Weinberg (co-founder and CEO of Harvey) Garrett Lord (co-founder of Handshake) Aidan Gomez (co-founder and CEO of Cohere) Michelle Zatlyn (co-founder of Cloudflare) Evan Spiegel (co-founder and CEO of Snap) 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/

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