All Episodes

EP 150: Bret Taylor (CEO, Sierra): A New Class of Software Winners

EP 149: Marc Benioff (CEO, Salesforce) Predicts Half of Conversations Will be With AI Agents Next Year

EP 148: Joe Hudson - The Leadership Coach Sam Altman and Top AI Teams Trust

EP 147: How Chris Degnan Built Snowflake's Sales Org From Scratch

EP 146: Bipul Sinha (CEO, Rubrik) on The New Rules of Silicon Valley

EP 145: Rick Smith (CEO, Axon): The Wild Ride From Near-Bankruptcy to $50B+

EP 144: Jeffrey Katzenberg & Sujay Jaswa (WndrCo) on What Startup Founders Can Steal From Hollywood

EP 143: Debunking Healthcare's Biggest Myths with Zach Weinberg and Derek Thompson

EP 142: Yotam Segev (CEO, Cyera) on Growing One of the Fastest Security Startups on the Planet

EP 141 Ben Lamm (Founder & CEO, Colossal Biosciences) On The Breakthroughs Making De-Extinction Actually Possible

EP 140: Blake Scholl (Founder and CEO, Boom Supersonic) on Why Supersonic Flight Failed & How Boom is Bringing it Back

EP 139: Matt Brown (NCAA Expert) on Athlete Pay Drama, Realignment of Power, and Transfer Portal Chaos

EP 138: Derek Thompson (Writer, The Atlantic) and Zach Weinberg (Co-founder & CEO, Curie.Bio) Discuss the Tariff Withdrawal and America’s Future

EP 137: Keith Rabois and Zach Weinberg Debate: Are Tariffs a Smart Economic Weapon?

EP 136: Zach Weinberg (Co-Founder & CEO, Curie.Bio) on The Tariff Trap, Self-Inflicted Recession Risk, and Open AI’s Fundraise

EP 135: Aaron Levie (CEO, Box) on Enterprise AI Trends No One is Talking About Yet

EP 134: Eric Yuan (CEO, Zoom): What Zoom’s AI Strategy Can Teach Every Operator

Ep 133: Flexport CEO Ryan Petersen Breaks Down the Global Impact of Trump’s New Tariffs

EP 132: Yamini Rangan (CEO, Hubspot) On Sales and Marketing Frameworks That Win in the Age of AI

EP 131: Andy Price (Artisanal): Executive Hiring Advice from the Founder of Tech’s Top Recruiting Firm

EP 130: Matt Mullenweg (Co-Founder WordPress): WordPress Controversy, Future of Open Source AI, and Navigating Backlash

EP 129: Tom Hale (CEO, Oura) Shares Health Habits That Will Make You a Better Leader

EP 128: Jay Chaudhry (CEO, Zscaler) On Picking The Best Markets, Risking Everything, & Scaling to $30B

EP 127: Marc Benioff (CEO, Salesforce): the Future of Digital Labor & the Agentic Era

EP 126: Eran Zinman (Co-Founder, monday.com) on The Efficiency Hacks That Drove monday.com to $14B

EP 125: Glenn Fogel (CEO, Booking Holdings) Building a $170B Travel Empire: On AI, Acquisitions, and Shaping Travel’s Future

EP 124: Databricks CEO Ali Ghodsi Breaks Down the AI Hype-Cycle

EP 123: Intercom CEO on Endorsing Trump, Reinventing The Company, and the Future of AI in Software

EP 122: Okta CEO Todd McKinnon on Scaling to $13B, High-Stakes Decisions, and Market Dynamics

EP 121: Snowflake CEO Sridhar Ramaswamy on the Future of AI and Data

EP 120: Evan Goldberg (Founder and EVP, Oracle NetSuite) on 26 Years of Operating Lessons Running NetSuite

EP 119: Drew Houston (CEO, Dropbox): Reflections on the 17+ Year Battle Against Big Tech

EP 118: Will Gaybrick (President of Product and Business, Stripe) on Capital Allocation, Org Design, AI, and Global Growth

EP 117: Parker Conrad (CEO, Rippling) His Opinion on Founder Mode, Fundraising, and VC Advice

EP 116: John Fieldly (CEO, Celsius) How He Saved Celsius From Near Bankruptcy to a $10B Company

EP 115: Josh Wolfe (Co-Founder, Lux Capital) On Uncovering Hidden Opportunities

EP 114: Emery Wells (CEO, Frame.io) on Selling to Adobe for $1.3B, Working with SNL and High Pain Tolerance

EP 113: Dara Khosrowshahi (CEO, Uber) Lays Out the Path to Autonomous Vehicles

EP 112: Mike Maples (Founding Partner, Floodgate): What Makes Startups Win & The Future of Venture Capital

EP 111: How Josh Reeves (CEO, Gusto) Built a $10B Company Serving Small Businesses

EP 110: How Eric Glyman (CEO, Ramp) Runs One of The Fastest Growing Startups

EP 109: Sebastian Siemiatkowski (CEO, Klarna) on the Future of Klarna, Valuation Changes and AI in Finance

EP 108: Olivier Pomel (CEO, Datadog) Shares Every Lesson From Scaling to $40B

EP 107: Steve Kaufer (Co-Founder, Tripadvisor) - Why He Left & What He’s Building Now

EP 106: How Bill Shufelt (CEO, Athletic Brewing) Built Athletic Brewing - Every Plot Twist Along The Way

EP 105: Vlad Tenev (CEO, Robinhood): The Meme Stock Crisis, The Future of Crypto, and AI Opportunities in Finance

EP 104: Sam Altman (CEO, OpenAI) talks GPT-4o and Predicts the Future of AI

EP 103: The Untold Story of Marcus Ryu (Co-Founder Guidewire & Partner at Battery Ventures) Scaling to $10B and Diving into VC

EP 102: Armon Dadgar (Co-Founder, HashiCorp) Reflects 48-Hours After Selling to IBM

EP 101: Andrew Bialecki (CEO, Klaviyo) on Building a $6B Software Company - Klaviyo’s Uncharted Path

EP 100: Jeremy Levine (Partner, Bessemer) Reflects on His Best and Worst Investments

EP 99: Garret Langley (CEO, Flock Safety) - The $4B Tech Startup Solving Crime with AI

EP 98: Sanjit Biswas (CEO, Samsara) on Building to $20B: The CEO Behind One of The Fastest Growing Startups Ever

EP 97: How Aravind Srinivas (CEO, Perplexity) is Disrupting Google Search with AI

EP 96: Tracy Young (CEO, TigerEye) Emerges from Stealth and Shares Every Mistake She Made As A First-Time CEO

Industry Episode with Zach Weinberg: Market Trends, Avoiding Hiring Bulls***ers, and Who Will Win In AI

EP 95: Tooey Courtemanche (CEO, Procore) Everything This Veteran CEO Would Tell Founders After Building To $11B

EP 94: Niraj Shah (CEO, Wayfair) Building To $10B in Home Decor Revenue

Parker Conrad (CEO, Rippling): The Zenefits Redemption Story That Led to Rippling ($11B)

EP 93: Filip Kaliszan (CEO, Verkada) AI Security Cameras to $3.5B Company

EP 92: Mike Volpi (Partner, Index Ventures) Top AI Investor Predicts How The AI Wave Will Play Out

EP 91: How George Kurtz (CEO, Crowdstrike) Built A $65B+ Company

EP 90: Eric Vishria (General Partner, Benchmark Capital) Behind The Scenes of Benchmark’s Boldest Bets

Best of 2023: 15 Untold Stories From Tech’s Inner Circle

EP 89: Jay Kreps (CEO, Confluent) on Confluent’s Resilient Rise to Software Behemoth

EP 88: Nikesh Arora (CEO, Palo Alto Networks): The CEO that Revolutionized Palo Alto Networks To ~$100B

EP 87: Luis von Ahn (CEO, Duolingo) on The Marketing Formula that Propelled Duolingo to 500M Users

EP 86: Christian Chabot (Co-Founder, Tableau) on Operating Lessons From Scaling Tableau to $15.7B

EP 85: Alexandr Wang (CEO, ScaleAI): The 26-Year-Old Powering the AI Industry

Behind The Scenes - Every Podcast Mistake We’ve Made In 85 Episodes

EP 84: Dev Ittycheria’s (CEO, MongoDB) Leadership Lessons From Scaling MongoDB to $25B

EP 83: Silicon Valley Legend Claire Hughes Johnson (Advisor, Stripe) Unveils Her Best Operating Advice

EP 82: Dario Amodei’s (CEO, Anthropic) AI Predictions Through 2030

EP 81: Matthew Prince (CEO, Cloudflare): Untold Stories Behind the $20B Business That Runs the Internet

EP 80: Jack Altman (CEO, Lattice) on Founding Lattice ($3B), Motivating Employees and Growing up with Sam

EP 79: Liz Zalman and Jerry Neumann (Co-authors, Founder VS Investor) debate startup experiences

EP 78: Vlad Magdalin (Co-Founder and CEO, Webflow): Finding Gratitude Amidst Business Chaos

EP 77: Ryan Smith (Utah Jazz Owner, Qualtrics Co-Founder): HS Dropout Turned Tech Founder Bought His Hometown NBA Team

EP 76: John McMahon (5x CRO and Enterprise Sales Expert) on The Startup Sales Playbook Every Founder Needs

Palmer Luckey (Founder, Oculus and Anduril): How He Got Fired For Making a $9,000 Donation in Support of Trump

EP 75: Wade Foster (Co-founder and CEO, Zapier) on Nearly Bootstrapping to $5B

EP 74: Laela Sturdy (Head of CapitalG) on Why Alphabet Invests in Startups

EP 73: Jyoti Bansal (Founder, AppDynamics): Life After Selling a $3.7B Company

Industry Episode: Zach Weinberg (Founder, Curie.Bio) on VC Predictions, Remote Work, and the AI Wave

Peter Fenton (Partner, Benchmark) on VC and Founder Mindsets, Inflation, and the Current Market State

EP 72: Jaan Tallinn (Co-Founder, Skype) on Lessons from Skype, Giving SBF $100M & Investing in AI

EP 71: TJ Parker (Founder, PillPack) on Selling to Amazon for $1B and Going to War with Big Pharma

EP 70: Tim Urban (Author, "Wait But Why") on Wokeness, AI Girlfriends and Humans Living to 150 Years Old

EP 69: Emmett Shear (Co-Founder, Twitch). Behind-The-Scenes stories from Twitch's growth to streaming leader

EP 68: Immad Akhund (CEO, Mercury) on How Mercury Added $2 Billion in Deposits After SVB Collapse

EP 67: Daniel Ek (CEO, Spotify) on the Creation of Wrapped, How Apple Blocks Innovation & Growing Up in the Projects

EP 66: George Boutros (CEO, Qatalyst) On Negotiating the Biggest Tech Acquisitions (LinkedIn, Slack, Figma) and Advising Steve Jobs in 1996

EP 65: Aaron Levie's (CEO/Cofounder, Box) AI Takes and Advice for First Time Founders

EP 64: Jay Simons (GP, BOND Capital) On How Product-Led Growth Turned Atlassian into a $40B Company

EP 63: Eliezer Yudkowsky (AI Safety Expert) Explains How AI Could Destroy Humanity

EP 62: Keith Rabois (Partner, Founders Fund) Lessons from Peter Thiel & Reid Hoffman, and Why He'd Never Invest in a Remote-First Company

EP 61: Dan Runcie (Founder, Trapital) on the Business of Music and What Founders Can Learn from the Top Artists

EP 60: Scott Raney and Satish Dharmaraj (Investors, Redpoint) Breakdown Venture Capital and Why AI Will Be Bigger Than Mobile

EP 59: Robin Hanson (Economist) -So AI Is Not Going to Kill Us All?

EP 58: Annie Lamont (Co-founder, Oak HC/FT) - The State of the Market and Being a VC in the 90s

EP 57: Brian Halligan (Co-founder, HubSpot) - The Path to Building a $20B Business

EP 56: Kevin Ryan (AlleyCorp, MongoDB, Business Insider, Zola) – The Rise of Psychedelics as Healthcare, Early Days of the Internet, State of the Market

Industry Episode (SVB): Dan Primack (Axios) + Eric Newcomer (Newcomer) - Where the Venture Industry Goes from Here

EP 55: Spenser Skates (Co-Founder/CEO, Amplitude) - Going Public, Exercise Windows and Why Sales is More Important Than Engineering

EP 54: Zach Weinberg (Founder, Curie.Bio) - Raising $520M to Fix Biotech

EP 53: Dr. Toyin Ajayi (Co-founder/CEO Cityblock Health) - Founding a $6.2B Business Focused on Providing Healthcare to the Impoverished

EP 52: Jason Warner & Jacob Effron (Redpoint Ventures) - Former GitHub CTO Explains AI for Dummies

EP 51: Matt Mochary (Founder, The Mochary Method) - The Coach Behind Sam Altman, Naval, Brian Armstrong Shares the Mistakes That All CEOs Make

EP 50: Alan Patricof (Founder, Apax/Greycroft/Primetime Partners ) - On Burning Man and a marathon at 87, early investments in Apple and AOL, plus, how he almost made it to Woodstock

EP 49: Elad Gil (Angel Investor) - Solo Capitalist and Early Airbnb Investor Shares Secrets of Silicon Valley & the Worst Advice That Founders Get

EP 48: Peter Reinhardt (Founder/CEO, Segment/Charm Industrial) - Quitting the Software Industry, Dropping out of College and Climate Change

EP 47: Kara Swisher (Founder, Recode) - Tech journalist and podcaster on the evolution of the tech industry, Propaganda vs Journalism, Elon & Who Should Run Twitter

EP 46: Emad Mostaque (Founder/CEO Stability.ai) - On The Future of Generative AI, Creating Real-Time Movies, Societal Impact of AI

Best of Cartoon Avatars 2022: Bonus Episode 45 – Our Favorite Interviews and Debates Featuring Mark Cuban, Parker Conrad, Will Hockey, Dick Costolo and More

EP 44: Sid Sijbrandij (Founder/CEO, GitLab) - Corporate Transparency, Open Source Philosophy, Remote Work and Global Talent Pools

EP 43: Semil Shah (Partner, Haystack) - The State of Venture, Investing in Figma, Hashicorp, Doordash and Almost Investing in Coinbase

EP 42: Zach Weinberg Returns, His Take on FTX, Venture’s Culpability and the Possible Death of Twitter

EP 41: FTX Part 2 and the Twitter Breakdown: Aztec’s Jon Wu joins to talk FTX then Former Twitter Director Ryan Sarver & Fintwit Poster Compound248 Break Down Elon’s Takeover, Paid Verification, Advertisers Fleeing and the FTC

EP 41 - Bonus Episode: Mike Burgersburg, Twitter Poster Who Helped Discover FTX’s Issues, Breaks Down How It All Happened

EP 40: Peter Fenton, VC and Founder Mindsets, Current Market State and Rashad’s New Podcast

EP 39: All-In’s Jason Calacanis Joins, Breaking Into Media, Tech in Journalism and the Kanye Controversy

EP 38: Anchor CEO/Founder, Spotify’s Former Head of Talk and Lightspeed Partner Mike Mignano talks the History/Future of Podcasting, Clubhouse and Web3 for creators

EP 37: Mark Cuban Talks with Us About How He Succeeded, Advice for Young Entrepreneurs, Buying the Mavericks & Cost Plus Drugs

EP 36: Fivetran CEO George Fraser and Young VCs Launching Funds

EP 35: NYT CEO Meredith Kopit Levien, Bankless’ David Hoffman and Zach Weinberg Crypto Debate, Live at Live at Primary's NYC Summit

EP 34: Interview w/ Oculus & Anduril Founder Palmer Luckey + Jon Sakoda Predicts Record VC Investments

EP 33: Maven Founder Kate Ryder, Zach’s Documentary, Adobe's Figma Acquisition and the State of Healthcare

EP 32: Former Twitter CEO Dick Costolo Talks About His Time at Second City, Running Twitter, and Missing Out on Instagram

EP 31: Anonymous Fintwit Personality Compound248 Joins to Talk LP Allocation Strategy, the Yale Model, Spotify and Twitter

EP 30: Conversation with Plaid & Column Founder William Hockey, Covering Adam Neumann with Author Maureen Farrell and Common Founder Brad Hargreaves

EP 29: Multicoin Capital’s Kyle Samani Joins the Crypto Debate and Chat Helium, Also Amazon-One Medical and Productivity at Big Tech

EP 28: Convo with Web3 is Going Just Great Creator Molly White, plus State of the Market, a Convo on Secondaries and Sam Lessin Recap

EP 27: Convo with Lux’s Josh Wolfe and Our Best/Worst Crypto Debate with Slow Venture’s Sam Lessin

Bonus Episode: Logan Bartlett’s Guest Appearance on Ordinary Astronauts: Talking the Why Behind Cartoon Avatars and the State of VC

EP 26: Chaos Monkey’s author Antonio García Martínez talks book, Facebook conspiracy theories, and a Web3 debate

EP 25: Braze’s Bill Magnuson talks the “aha moment” and advice for entrepreneurs, plus Rashad Assir’s path to Redpoint TikTok

Bonus Episode: The Elon Musk Twitter Saga w/ Axios' Dan Primack

EP 24: QED’s Frank Rotman Talks Crypto and Capital One Origins, Plus Redpoint’s Own TikTok Guy Revealed

Bonus Episode: Logan and Zach on the "Best Business Show w/ Anthony Pompliano - Episode: 239"

EP 23: Non-Crypto Talk with Zach Weinberg plus Interview with Acquired Podcast’s Ben Gilbert and David Rosenthal

EP 22: Crypto Debate with Shaun Maguire & Zach Weinberg + Interview with Papa Founder Andrew Parker

EP 21: Aztec’s Jon Wu Joins Zach’s Crypto Debate, Plus the Celsius Disaster & Crypto as Bird Talons

EP 20: Interview with Ramp’s Eric Glyman (+ explaining Cartoon Avatars’ origins) and a Crypto Debate with Mike Dudas and Zach Weinberg

EP 19: Matt Levine, Meme Stocks, Crypto Crash and Terrible Attempts at Crime

EP 18: Parker Conrad, Sequoia’s Leaked Deck, a Different Kind of Crisis and VCs vs. Hedge Funds

EP 17: Benedict Evans on State of Tech, and Alexis Gay on the Risk in Leaving it All Behind for Comedy

EP 16: CEO of Box Aaron Levie gives founder advice, Founder of Flatiron Zach Weinberg returns as guest host, and crypto expert Eric Golden joins to discuss UST-Luna!

EP 15 Pt 1: VC Meme King @prayingforexits Comes on to Discuss a Host of Topics, Then a Group of Apes Talk BAYC

EP 15 Pt 2: Packy McCormick and Ben Thompson Talk About Their Own Start, Finding Your Audience and The Creative Process

EP 14: Lux Capital’s Josh Wolfe Talks Musk, Adobe’s Scott Belsky Talks Twitter, Bolt and Breslow Again, and Entering The Golden Age of Fraud Lawyers

EP 13: An Interview with Keith Rabois on Why He Tweets and Miami Tech Week, Netflix Loses 200K Subscribers, and Even More Elon

EP 12: Dan Primack Talks Musk/Twitter, Zach Weinberg Explains Founding a $2.1B Co & Owning Nightclub

EP 11: Elon Musk Buys 9.2% of Twitter, A Deep Dive Into Twitter History, The End of Fast, and Nikita's Best Man Speech

EP 10: Interview with Ryan Breslow, The Silicon Valley Mob, Twilio Insider Trading and Why OnlyFans Can’t Find Investors

EP 9: Facebook Execs Go Extremely Remote, Bored Ape Yacht Club’s Gaming Era, Ethereum Regret and Nikita’s Back Once Again!

EP 8: AMC’s Gold Mine, The Business of Memes, Glossier Article, and We’re Joined by Packy McCormick and Roseanne Wincek

EP 7: Bain Capital Crypto, Bolt's Breslow back w/ Crypto Pharma, Alumni Ventures and Standard VC Fees, Tiger Partners Fund Seed Managers

EP 6: Super Pumped, BitConnect’s Possible Ponzi Scheme, Homebrew and Randi Zuckerberg’s Music Video

EP 5: Coinbase Tweet Storm, Truth Social, Death of the Five Day Work Week and the ClearCo Breakup

EP 4: State of Venture Market, Crypto Ads, ETHDenver, Razzlekhan Revisited and Nikita’s G-Wagon Disloyalty

EP 3: Razzlekhan and Crypto, Bored Ape Reveal, Binance and Forbes, and Peloton’s CEO

EP 2: Wordle, Wordcels & Shape Rotators, Miami Tech, and FB Earnings

EP 1: Bolt vs. Stripe, Calendly, Market Meltdown and Billionaires Tweeting