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"This Won't Last" with Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg

Turpentine, Keith Rabois, Logan Bartlett, Zach Weinberg, Kevin Ryan

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Sit in on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel where they unpack their hottest takes on the future of tech, business, venture, investing, and politics. This Won't Last is part of the Turpentine podcast network. Learn more: www.turpentine.co
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The Logan Bartlett Show

by Redpoint Ventures

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Startups grow faster and avoid costly mistakes when they learn from those who came before them. In each episode, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead o ...
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Bret Taylor is the CEO of Sierra and Chairman of the Board of OpenAI. He previously served as co-CEO of Salesforce. I sat down with Bret to explore how the AI revolution compares to previous platform shifts and what it means for both startups and incumbents navigating this transition. (00:00) Introduction and Recent Milestone (00:38) AI Market and …
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Logan is joined by Marc Benioff, the legendary co-founder and CEO of Salesforce, for a wide-ranging conversation on the rise of AI in enterprises. Marc explains how Salesforce has become the testing ground for its own “agentic” technology, using AI agents to handle customer support, boost sales, and transform marketing. He also shares his perspecti…
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Joe Hudson is the founder of The Art of Accomplishment and has worked with many top leaders in Silicon Valley, including Sam Altman and executives from Apple, Google, the NBA, and more. He coaches the research and compute teams at OpenAI and works with all the major AI companies. With a background in international stock lending and venture capital,…
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Chris Degnan is one of the most legendary CROs of this generation. He joined Snowflake as employee #13 and the 1st sales hire. He scaled the sales org from 0 to over $3B in ARR, spanned four CEOs, and retired as CRO after 11 years. In his first podcast post-retirement, Chris opened his CRO playbook, from early enablement to hiring rigor and fending…
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Logan sits down with Bipul Sinha, CEO and co-founder of Rubrik and former VC at Lightspeed and Blumberg Capital. Bipul shares what he learned transitioning from investor to founder, why intuition beats expertise, and how he built Rubrik into a category-defining business by betting on uncool ideas. They talk product-market fit in the AI era, what mo…
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Rick Smith (CEO, Axon) joined Logan to share the 30-year journey of building a nearly $50B public company behind the TASER, police body cameras, and now AI-powered tools like Draft One. He talks about taking Axon public in the early 2000s, navigating intense public scrutiny, and evolving from a controversial hardware startup into a software and AI …
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Logan sits down with Jeffrey Katzenberg, Hollywood legend and co-founder of DreamWorks, and Sujay Jaswa, former CFO of Dropbox - together, the duo behind WndrCo. They talk about building enduring companies, bridging tech and media, and what makes a great CEO partnership. The conversation also touches on storytelling as a business superpower and les…
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In this episode, Logan is joined by Zach Weinberg (Co-Founder/CEO @ Curie.Bio) and Derek Thompson (writer at The Atlantic) for a candid discussion on the state of U.S. healthcare and scientific progress. They unpack what went right, and wrong, with COVID vaccine policy, the public backlash against mRNA technology, and the ripple effects on trust in…
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Yotam Segev is the co-founder and CEO of Cyera, one of the fastest-growing cybersecurity startups in the world. In this episode, he joins Logan to talk about scaling Cyera from 100 to 550 employees in under two years, what it takes to operate at that speed, and why going slow can actually be riskier. They cover lessons from a tough go-to-market yea…
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This is the fourth episode of This Won’t Last. The show is a monthly conversation between Logan Bartlett of Redpoint, Keith Rabois at Khosla Ventures, Kevin Ryan at Alleycorp, and Zach Weinberg at Operator Partners. This episode covers tech’s relationship with DC, entitlement spending, auto tariffs, the future of American politics, and more. This W…
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Ben Lamm, founder and CEO of Colossal Biosciences, joined the show to talk about the science (and business) of bringing extinct species back to life. Backed by top scientists and investors, Colossal is using advanced gene editing and synthetic biology to recreate animals like the woolly mammoth and dire wolf. Ben walks us through the technology, et…
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Blake Scholl, founder and CEO of Boom Supersonic, is leading the boldest effort in decades to bring back commercial supersonic flight—this time with product-market fit. We talk about what went wrong with the world’s first try at supersonic commercial aircraft (launched in the 70s), why Boeing hasn’t introduced a new plane in over a decade, and how …
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College sports are going through massive changes—from athlete pay drama to superconference realignment and transfer portal chaos, not to mention the giant class action lawsuit playing out now. Matt Brown, the publisher behind Extra Points and one of the top experts on the business of college athletics, joined the show to break it all down. We walke…
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In this episode, Derek Thompson (Writer, The Atlantic) delves into the tumultuous nature of Trump’s trade policies, especially regarding tariffs, and how they impact American manufacturing and global markets. They discuss the constant changes in policy, the resulting uncertainty for industries like automotive and aerospace, and the mismatch between…
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Debate between Keith Rabois and Zach Weinberg on what tariffs are actually trying to accomplish. One core theme: Tariffs aren’t fully about “bringing back factories,” but rather a negotiation tool to eliminate foreign trade barriers - ultimately aiming to increase free trade, not restrict it. We also got into: - What each of them would do if they w…
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In this freeform episode, Logan sits down with Zach Weinberg (Co-Founder and CEO of Curie.Bio) to break down two of the biggest storylines in tech: tariffs and AI. They banter through the core arguments for and against tariffs, including national security, domestic employment, and negotiation power. Plus, they revisit what’s happened in past trade …
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Box CEO Aaron Levie joined the show to share his perspective on how AI is reshaping the enterprise landscape. He shared what his customers are actually thinking about when it comes to AI, the shift from closed to open-source models, and why the biggest opportunities might not be in flashy consumer tools but in workflow automation and data-rich ente…
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After unveiling 45 new product announcements this week, Zoom CEO Eric Yuan joined the show to share how he’s thinking about the future of work. He shared how he prioritizes which features to build, his approach to rebuilding company culture, what he’d do differently if he were starting Zoom today, and much more. (00:00) Intro (01:14) Eric Yuan on Z…
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As tariff drama continues to heat up, Ryan Petersen, CEO of Flexport (one of the hottest freight forwarders in the world) came on the show to unpack the impact. Ryan also dives deep into the hidden world of US shipping, opportunities for AI automation in logistics, reflections on building Flexport, and some supply chain conspiracy theories. (00:00)…
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Yamini Rangan, CEO of HubSpot (a $40 billion leader in the CRM space) shares how AI is transforming go-to-market strategies, the key lessons Yamini has learned as a first-time CEO, and the sales tactics she’s mastered. She also discusses the challenges of navigating major business pivots, including how companies can successfully transition into AI-…
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Andy is the founder of Artisanal Ventures and Artisanal Talent, one of Silicon Valley’s top search firms. He’s helped build leadership teams at companies like Databricks, Snowflake, Confluent, Abnormal Security, AcuityMD, and many more. In this episode, he shares… - How founders can differentiate in the talent war today - Maximizing the success rat…
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The recent controversy between WordPress and WP Engine put Matt Mullenweg (Co-Founder of WordPress, CEO of Automattic) under intense online scrutiny. In our conversation, he shared lessons from the controversy and managing through crisis, as well as this thoughts on the future of open source AI and more. (00:00) Intro (01:17) Controversy with WP En…
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Two weeks after Oura CEO Tom Hale started tracking and improving his sleep, he recalls, “It was like walking out of a black-and-white movie into a 4K technicolor movie… I’ve been missing this for 30 years.” The experience of feeling 20 again every day inspired him to apply for the Oura CEO role. Now, nearly 3 years into the job, he sat down to disc…
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This is the third episode of This Won’t Last. This episode covers Silicon Valley's unprecedented attendance at Trump's inauguration, tech's evolving stance on energy and regulation, and why America's economy struggles to achieve the growth rates it saw from 1950-2000. The show is a monthly conversation between Logan Bartlett of Redpoint, Keith Rabo…
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Jay Chaudhry is the definition of a self-starter. Born in the Himalayas with no running water or electricity until high school, Jay has now scaled Zscaler to a $30B public company. He and his wife went all in many times over—betting their life savings and quitting their jobs to launch their first venture, Secure IT, which became a huge success. Jay…
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In this episode, Marc Benioff (CEO, Salesforce) responds to Satya Nadella’s recent predictions and shares his thoughts on the current reality of Agi. He dives into the rise of digital labor, the multi-trillion-dollar potential of agentic technology, and what the future split between software and agentic revenue might look like. Marc also discusses …
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Eran Zinman entered a crowded category, out-executed everyone, and scaled monday.com into a $14B public company. In my latest conversation with him, he details their unique metric tracking system (dubbed Big Brain) that allows them to do the same amount of work with ½ the people, along with their relentless focus on cash over other metrics, and the…
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Glenn Fogel, CEO of Booking Holdings, has built a $170B travel empire that includes brands like http://Booking.com, Priceline, Kayak, and OpenTable. Glenn shares insights into how Booking has grown into a global powerhouse, weathering challenges like tsunamis, wars, 9/11, and the COVID-19 pandemic. We dive into the strategy behind the transformativ…
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Ali Ghodsi, CEO of Databricks (now a $61B company), has become one of the top minds in AI, evolving from researcher to leading one of the biggest AI-centered private companies. In our conversation, he broke down the AI hype cycle in detail and made bold predictions for the future. He also shared his biggest operating lessons from scaling Databricks…
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Eoghan McCabe returned to the CEO seat at Intercom with a mission to shake things up. Over the past two years, he's been reinventing the company’s culture, leading with zero apologies, and transforming Intercom into an AI-driven powerhouse. In my latest conversation, we dive into Eoghan’s journey back to Intercom after a two-year break, his bluepri…
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What does it take to scale a company from an idea to a $13B industry leader? In my latest episode, Okta CEO Todd McKinnon dives into the essential lessons he’s learned on high-stakes decision-making, managing up to the board, and competing against tech giants like Microsoft. Todd also reflects on his journey to founding Okta, his bold choice to tea…
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Nine months into his role as Snowflake’s CEO, Sridhar Ramaswamy sat down for a candid discussion on the journey so far & what’s ahead. He uncovered details about his transition to Snowflake CEO, the operational changes he’s put in place to accelerate product development, and his bold predictions for AI’s future—along with how he’s guiding a vision …
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Evan Goldberg has been leading NetSuite for 26 years and counting. In this episode, Evan reflects on the journey of building NetSuite—from launching it with Larry Ellison’s support, to scaling through its IPO, and eventually being acquired by Oracle for $9.3B. He shares his leadership philosophies around humor and empathy, lessons learned from Larr…
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Drew Houston has now been CEO of Dropbox for over 17 years. In my latest conversation, he opens up about the pivotal leadership lessons he's learned, the mistakes that shaped the company, and the true challenges of going head-to-head with big tech. We also dive into the highs and lows of fundraising, how valuations can make or break a company traje…
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This is the second episode of This Won’t Last. The show is a monthly conversation between Logan Bartlett of Redpoint, Keith Rabois at Khosla Ventures, Kevin Ryan at Alleycorp, and Zach Weinberg, biotech founder (Curie.Bio) and investor. This episode covers Khosla’s initial investment into OpenAI, runaway AI CapEx, long-term AI leaderboards, and reg…
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Will Gaybrick joined Stripe as CFO after investing in the company at Thrive Capital. Over the past 9 years, now as President, he's helped grow Stripe's into one of the world's largest private startups. In this episode, we explore his impressive career journey—from Harvard Math to software engineering, Yale Law, venture capital, and now his leadersh…
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Parker Conrad has spent the last 8 years building Rippling into a $13B company, marking his redemption after being ousted from Zenefits. In his second appearance on the podcast, Parker and I discussed Paul Graham's "founder mode" essay and how he operationalizes it at Rippling. He also reflected on the key lessons he's learned throughout his career…
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This is the debut episode of This Won’t Last, a monthly conversation between Logan Bartlett of Redpoint, Keith Rabois at Khosla Ventures, Kevin Ryan at Alleycorp, and Zach Weinberg, biotech founder (Curie.Bio) and investor. This episode covers Founder Mode, the state of VC fundraising, the potential for an unrealized gains tax, and Russia’s influen…
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Many know Celsius as a top energy drink brand today, but few are aware of the tumultuous journey CEO John Fieldly took to get it here. In the episode, John shared how the company nearly went bankrupt multiple times, lost 50% of its revenue overnight and even got delisted from the NASDAQ. Despite these challenges, John stepped up to rebuild the bran…
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Josh Wolfe, co-founder and managing partner at Lux Capital, is a master at quickly understanding complex, emerging technologies. In our conversation, Josh shared how he identifies the next big thing, his contrarian views on nuclear energy, biotech, and robotics, as well as his thoughts on the state of the venture capital market today. (00:00) Intro…
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Emery Wells is the co-founder and CEO of Frame.io, which he sold to Adobe in 2021 for nearly $1.3 billion. In our conversation, Emery shares his journey from NYC bartender to startup founder, including his agency work with Saturday Night Live that highlighted the pain points that led to Frame.io. We dive deep into his rejection of the lean startup …
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Dara Khosrowshahi runs one of the most complicated businesses in the world, Uber. Since taking over in 2017 Dara has led the company to profitability against all odds. In this episode, we touch on a number of things including Uber’s position on the future of Autonomous Vehicles (AVs), the challenges that were overcome in making Uber profitable, and…
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Mike Maples is an 8x Midas List investor and founding partner at Floodgate Fund. In our conversation, we dive into his latest book, "Pattern Breakers: Why Some Startups Change The Future." Mike shares his frameworks on how top startups beat incumbents by redefining categories, and he reflects on his worst and best decisions. We also discuss what th…
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Josh Reeves has built Gusto into a nearly $10B company with over $500M in ARR, serving small businesses. In our conversation, Josh delves into Gusto’s 13-year journey, sharing insights on how they achieved product-market fit by initially targeting a very narrow niche. He also highlights the tactics they’ve used to build an intentional culture of hu…
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Eric Glyman (CEO, Ramp) shared his operating playbook for leading one of the fastest-growing startups on his second appearance on the podcast. We also explored the unique ways Ramp leverages AI internally, strategies for startups to build moats in AI, and the concept of self-driving money. We concluded with one of the most profound and thoughtful d…
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Klarna CEO Sebastian Siemiatkowski led the rise from a profitable business to their peak $50 billion valuation, in which they were burning $150 million a month. In my latest episode, Sebastian shares how he turned Klarna back to profitability and discusses Klarna’s ongoing pursuit of creating a digital financial assistant. He also reflects on their…
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Olivier Pomel built Datadog into a $40B company while burning only $25M in capital. In our conversation, he shares the fundraising lessons, operating principles, and core insights that made this possible. He also discusses the pros and cons of building a tech company in NYC, how early-career professionals should approach learning AI tools, how Data…
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Steve Kaufer led Tripadvisor to multi-billion dollar success over a 20+ year run as CEO. He discusses getting acquired and spun out from IAC, becoming a public company CEO, and his biggest operating lessons from his decades-long journey. Steve also shares behind-the-scenes of his new venture, Give Freely, and reflects on his entrepreneurial path. (…
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Since 2017, Bill Shufelt (CEO, Athletic Brewing) went from hedge fund trader to the CEO of the leading producer of non-alcoholic craft beer. Unlike the typical tech-focused chats, this one centers around a product many have fallen in love with. In the conversation, Bill tells stories of the unscalable but crucial strategies he used to build a brand…
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In the midst of meme stock craziness, Robinhood CEO Vlad Tenev shared his most eye-opening insights from running the company that transformed the game for retail investors. He talks about Robinhood’s new Gold Card, his views on crypto, the media side, how artificial intelligence could change finance, and more. (00:00) Intro (03:27) The Origin of th…
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