On Unsupervised Learning, Redpoint Partners Jacob Effron, Patrick Chase, Jordan Segall and Erica Brescia explore the rapidly developing AI landscape and what it means for businesses and the world. With Redpoint’s history investing in companies such as Snowflake, Twilio, Stripe, Descript and hosts who have each been in both the builder and investor seat, subscribe now to make sure you don’t miss any of it.
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Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.
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The Sourcegraph Podcast is a new show about developer tools and their creators. It can sometimes feel like a full-time job just staying on top of the latest libraries, frameworks, plugins, extensions, CLI tools, and developer apps. We want to help you do that, by giving you a window into the minds of some of the best and brightest people working at the forefront of developer productivity. You'll hear from dev tool company founders, open-source authors, and developer efficiency leaders inside ...
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Ep 46: CEO of DeepL Jarek Kutylowski on Specialized vs. General Models, Beating Google and a Future with Synchronous Translation
56:10
I sat down with DeepL cofounder Jarek Kutylowski. DeepL is a comprehensive Language AI platform that enables organizations to communicate effectively across languages, cultures, and markets. Jarek shared a treasure trove of insights on the past, present, and future of AI translation. Here were some standout moments: [0:00] Intro [0:38] The Rise of …
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EP 120: Evan Goldberg (Founder and EVP, Oracle NetSuite) on 26 Years of Operating Lessons Running NetSuite
1:17:14
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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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EP 119: Drew Houston (CEO, Dropbox): Reflections on the 17+ Year Battle Against Big Tech
1:34:53
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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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Ep 45: Founder & CEO of HeyGen Josh Xu on TikTok’s GenAI Dilemma, Trust and Safety and the Path to Interactive Avatars
51:46
Joshua Xu is co-founder and CEO of HeyGen -- the fast-growing AI video creation and translation platform. You can upload a video, or create a new one from a script using an AI avatar as your star, and HeyGen will translate it into 175 languages. HeyGen now serves over 40,000 customers and is generating $35+ million in revenue. [0:00] Intro [0:37] H…
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Ep 44: Co-Founder of Together.AI Percy Liang on What’s Next in Research, Reaction to o1 and How AI will Change Simulation
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Percy Liang is a Stanford professor and co-founder of Together AI, driving some of the most critical advances in AI research. Percy is also a trained classical pianist, which clearly influences the way he thinks about technology. We explored the evolution of AI from simple token prediction to autonomous agents capable of long-term problem-solving, …
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EP 118: Will Gaybrick (President of Product and Business, Stripe) on Capital Allocation, Org Design, AI, and Global Growth
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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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Ep 43: CEO/Co-Founder of Contextual AI Douwe Kiela Reaction to o1, What’s Next in Reasoning and Innovations in Post-Training
57:23
Douwe’s contributions to AI are truly a part of its bedrock foundations. He wrote the first paper on retrieval-augmented generation (RAG) and has raised over $100 million to help enterprises build contextual language models that fit their use cases. Before Contextual he was the head of research at Hugging Face, worked on the Facebook AI research te…
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EP 117: Parker Conrad (CEO, Rippling) His Opinion on Founder Mode, Fundraising, and VC Advice
1:42:29
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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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Ep 42: CEO of Grammarly Rahul Roy-Chowdhury on the Future of Communication, Impact of LLMs and How Grammarly Does Eval
51:21
If you don’t know Grammarly, it’s a personalized AI assistant for writing that has over 30 Million Daily Active Users. Grammarly has been building AI productivity tooling long before the most recent GenAI wave and has raised over $400M, with a current valuation of $13B. Rahul believes AI will enable everyone to focus on more meaningful, creative in…
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Bonus Episode: Trunk Tools CEO Sarah Buchner is Building Trunk Tools to Simplify the $13T Construction Industry
21:11
Sarah Buchner is the Founder and CEO of Trunk Tools (https://trunktools.com/). She is a one-of-a-kind founder, having spent her young life as a carpenter in Austria and then working her way up the ranks of the construction industry. She’s also earned several graduate degrees including an MS in Civil Eng, a PHD in Data Science and an MBA from Stanfo…
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EP 116: John Fieldly (CEO, Celsius) How He Saved Celsius From Near Bankruptcy to a $10B Company
1:06:53
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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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Ep 41: Head of AI at Snowflake Baris Gultekin on Why They Built Their Own LLM, Governance as a Moat, and the Most Common Enterprise Use-Cases
46:51
Snowflake sits in a unique position in the AI landscape: They enable fast, secure, and scalable proprietary data access for thousands of customers, many of whom are building AI tools. They also maintain their own suite of AI products, increasing the utility of their platform and empowering customers who may not have the resources to build their own…
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EP 115: Josh Wolfe (Co-Founder, Lux Capital) On Uncovering Hidden Opportunities
1:54:27
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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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EP 114: Emery Wells (CEO, Frame.io) on Selling to Adobe for $1.3B, Working with SNL and High Pain Tolerance
1:41:57
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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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Ep 40: CEO of Speak.com Connor Zwick on How AI Will Change the Way we Learn
1:09:12
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We’re excited to bring you Connor Zwick, CEO and cofounder of Speak, on the podcast this week! Speak helps people learning a language have conversations with an AI speaking partner, which is critical to gaining fluency. It’s backed by OpenAI and most recently raised at a $500M valuation. Since launching in its inaugural market of South Korea in 201…
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EP 113: Dara Khosrowshahi (CEO, Uber) Lays Out the Path to Autonomous Vehicles
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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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EP 112: Mike Maples (Founding Partner, Floodgate): What Makes Startups Win & The Future of Venture Capital
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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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Ep 39: Github CEO Thomas Dohmke on Building Copilot, Scaling to 1.2M Users and the Future of Code
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It was very special to have Github CEO Thomas Dhomke on the pod for many reasons, not the least of which is that my partner Erica Brescia was COO at Gitlab just before joining Redpoint! Thomas has been at Github for almost 6 years, and has been CEO for almost 3 of those years. He has a pulse on what engineers around the world are looking for from t…
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EP 111: How Josh Reeves (CEO, Gusto) Built a $10B Company Serving Small Businesses
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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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Ep 38: Runway CEO Cristobal Valenzuela on the Next Frontiers for AI Media and The Role of Human Taste in AI Filmmaking
57:51
Cris is the co-founder and CEO of Runway, which builds breathtakingly real video AI tools, including the incredible Gen-3 Alpha foundation model. Cris sits right at the intersection of technology and creativity, and in 2023 was named to TIME’s 100 Most Influential People in AI. Runway is reported to be in talks to raise capital at a $4 Billion valu…
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EP 110: How Eric Glyman (CEO, Ramp) Runs One of The Fastest Growing Startups
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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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Ep 37: Co-Founder and CEO of Fireflies.ai Krish Ramineni on How AI Catalyzed Fireflies to 16M Users
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1:08:33
According to Ramp’s (ramp.com) quarterly spend report, Fireflies was the 4th highest AI platform by spend. With over 300,000 customers worldwide and 16M users, Fireflies.ai is operating at some of the largest scale amongst AI companies today. This week on Unsupervised Learning we had Krish Ramineni, Co-founder & CEO of Fireflies on to talk about ho…
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EP 109: Sebastian Siemiatkowski (CEO, Klarna) on the Future of Klarna, Valuation Changes and AI in Finance
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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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EP 108: Olivier Pomel (CEO, Datadog) Shares Every Lesson From Scaling to $40B
1:32:04
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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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Scott Belsky is the founder of Behance, a creative platform sold to Adobe in 2012. He’s since gone on to take on the role of Chief Product Officer at Adobe leading design for all products across Creative Cloud, Document Cloud and the Digital Experience business. This week on Unsupervised Learning Scott shares his thoughts on the future of creative …
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EP 107: Steve Kaufer (Co-Founder, Tripadvisor) - Why He Left & What He’s Building Now
1:39:55
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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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EP 106: How Bill Shufelt (CEO, Athletic Brewing) Built Athletic Brewing - Every Plot Twist Along The Way
1:15:20
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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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Ep 35: CEO of Suno Mikey Shulman on Future of Music with AI, Tactics for Model Eval and Solving the Blank Canvas Problem
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Last week, Suno announced $125M in funding, marking a significant milestone in their journey to reshape the music creation landscape. On this week's episode of Unsupervised Learning, we caught up with Suno's founder, Mikey Shulman, to dive into their approach to multiplayer music collaboration, how they got Suno to be so fast and the future of digi…
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EP 105: Vlad Tenev (CEO, Robinhood): The Meme Stock Crisis, The Future of Crypto, and AI Opportunities in Finance
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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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Ep 34: Eric Ries and Jeremy Howard (Answer.ai) on the Biggest Mistakes AI Founders are Making and Building the Bell Labs of AI
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1:00:00
In this week’s episode of Unsupervised Learning, we delve into the forefront of AI innovation with Eric Ries and Jeremy Howard. Eric Ries, renowned for pioneering the Lean Startup movement, has consistently influenced modern entrepreneurial strategies with his emphasis on agile, sustainable growth through innovation. Jeremy Howard is known for his …
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In this cross-over episode, Sam Altman sat down with Logan on the day of the ChatGPT-4o announcement to share behind-the-scenes details of the launch and offer his predictions for the future of AI. Altman delves into OpenAI’s vision, discusses the timeline for achieving AGI, and explores the societal impact of humanoid robots. He also expresses his…
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On the day of the ChatGPT-4o announcement, Sam Altman sat down to share behind-the-scenes details of the launch and offer his predictions for the future of AI. Altman delves into OpenAI's vision, discusses the timeline for achieving AGI, and explores the societal impact of humanoid robots. He also expresses his excitement and concerns about AI pers…
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EP 103: The Untold Story of Marcus Ryu (Co-Founder Guidewire & Partner at Battery Ventures) Scaling to $10B and Diving into VC
1:50:28
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After 18 years leading Guidewire (~$10B), Marcus Ryu made the transition from CEO to partner at Battery Ventures. In the episode, Marcus shares his journey of co-founding Guidewire in 2001, steering the company through its IPO in 2012, and building one of the largest vertical software businesses in the world. He shares his insights on how to build …
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EP 102: Armon Dadgar (Co-Founder, HashiCorp) Reflects 48-Hours After Selling to IBM
1:54:42
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After last week’s announcement that IBM is acquiring HashiCorp for $6.4B, HashiCorp co-founder Armon Dadgar discussed a few behind-the-scenes elements of the acquisition and HashiCorp’s full journey from the early days. Armon shares some of his biggest lessons from the journey, from fundraising to community building and more. (00:00) Intro (01:17) …
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Ep 33: CTO and Co-Founder of Sourcegraph on Current Landscape and Future of Software Development, How to Make RAG Better, and Building Towards the Agentic Future
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1:36:50
On this week’s Unsupervised Learning, Pat and I sat down with CTO and Co-Founder of Sourcegraph, Beyang Liu. Sourcegraph is a leader in the AI coding space, and recently launched AI coding assistant, Cody. Beyang shared with us his view on the current landscape of AI coding and the future of coding and software development. He also shared how Sourc…
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EP 101: Andrew Bialecki (CEO, Klaviyo) on Building a $6B Software Company - Klaviyo’s Uncharted Path
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1:52:44
Before Andrew Bialecki took Klaviyo public and scaled the company to $6B, he bootstrapped it to over $1M in ARR. In our discussion, Andrew reveals his philosophies around fundraising, finding the best talent, cultivating entrepreneurship inside Klaviyo, scaling culture, and more. (00:00) Intro (01:13) Klaviyo's Bootstrap Beginnings (09:37) The Stra…
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EP 100: Jeremy Levine (Partner, Bessemer) Reflects on His Best and Worst Investments
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2:44:43
After 23+ years in venture capital, Jeremy Levine has thrived in many eras, taking risks on now-iconic companies like LinkedIn, Shopify, Yelp, Pinterest, and more. In our discussion, Jeremy shared stories behind these investments and the mindsets he’s developed along the way. We also explored how the VC landscape has evolved over the last 20 years …
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Ep 32: CEO and Founder of Pinecone Edo Liberty on Pioneering Vector Databases, Barriers to Productionalizing Models and Why What’s Happening with GPUs is Not Sustainable
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1:01:12
Pinecone has raised over $130 million and was most recently valued at $750 million. On this week’s Unsupervised Learning, we sat down with CEO and Founder of Pinecone, Edo Liberty. Pinecone is arguably one of the most important elements in today's modern datastack. Edo shared with us the most common use cases of Pinecone, the evolving landscape of …
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EP 99: Garret Langley (CEO, Flock Safety) - The $4B Tech Startup Solving Crime with AI
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Garrett Langley is the CEO of Flock Safety, a $4B company helping solve 10% of US crimes with AI-powered tech. Garrett offers an in-depth look into Flock Safety’s ambitious vision to eliminate crime in America and all the operating lessons he’s learned along the way, including how to build a strong and motivated team, keep people accountable, and l…
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EP 98: Sanjit Biswas (CEO, Samsara) on Building to $20B: The CEO Behind One of The Fastest Growing Startups Ever
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In less than 8 years, Sanjit Biswas scaled Samsara from 0 to over $1B ARR. In our latest conversation, Sanjit shares all the lessons he’s learned about running a hyper-growth organization, including all the changes he’s made since growing and selling his first company Meraki to Cisco for $1.2B and going on to scale Samsara to $20B. A great episode …
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EP 97: How Aravind Srinivas (CEO, Perplexity) is Disrupting Google Search with AI
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One of the most preeminent AI founders, Aravind Srinivas (CEO, Perplexity), believes we could see 100+ AI startups valued over $10B in our future. In the episode, we discuss why Perplexity decided to compete with Google and Aravind shares predictions for the utopian future of artificial intelligence. He also discusses the differences between workin…
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Ep 31: CEO and Co-Founder of Mistral Arthur Mensch on the Next Frontiers for LLMs, Why Open Source Will Prevail and AI Safety
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Mistral AI is often seen as the startup challenging OpenAI and incumbents developing LLMs. On this week’s episode of Unsupervised Learning, we sat down with CEO and Co-Founder at Mistral AI, Arthur Mensch. Arthur shared with us his view on why open-source will prevail, how Mistral gets LLMs into the hands of enterprises, the build vs. partnership d…
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EP 96: Tracy Young (CEO, TigerEye) Emerges from Stealth and Shares Every Mistake She Made As A First-Time CEO
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1:35:35
This week, Tracy Young launched her second startup, TigerEye, from stealth mode. After selling PlanGrid to Autodesk for $875 million and working with YC for a couple of years, Tracy and her husband/co-founder decided to build the software they wished they’d had while building PlanGrid. In our conversation, Tracy unmasks her vision for TigerEye and …
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Ep 30: Superhuman CEO Rahul Vohra on the Future of Email with AI and the Role Agents Will Play
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Superhuman recently launched AI-powered Summarize and Instant Reply features, and has since processed 4 billion emails. On this week’s episode of Unsupervised Learning, we sat down with CEO and Founder at Superhuman, Rahul Vohra. Rahul shared with us what email will look like in the future, the internal product design decisions in building Summariz…
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Industry Episode with Zach Weinberg: Market Trends, Avoiding Hiring Bulls***ers, and Who Will Win In AI
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Zach Weinberg is the Co-Founder and CEO of Curie.Bio, which has raised over $500 million to combine early-stage investing in biotech and drug discovery copiloting. He is also the co-founder of Flatiron Health, which sold to Roche for $1.9B, and Invite Media, which sold to Google when he was 21. In the episode, Zach dives into the current venture ma…
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EP 95: Tooey Courtemanche (CEO, Procore) Everything This Veteran CEO Would Tell Founders After Building To $11B
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1:39:36
Tooey Courtemanche has been the CEO of Procore for over two decades, bringing the company from $0 to over $1B ARR and a $11B+ valuation today. In my latest episode, we explore how Tooey built the #1 Construction Management Software company, including his strategies for maintaining a talented team, his mindsets for tough times, lessons from mentors …
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Ep 29: Salesforce AI CEO Clara Shih on Future of Slack, How Gucci Uses AI and Working with Marc Benioff
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There’s an ongoing debate about where the most value will accrue in AI between incumbents and startups. Of the incumbents, few have shipped product faster than SalesforceAI. Today on Unsupervised Learning we had on Clara Shih, CEO of SalesforceAI and one of Time Magazine’s 100 Most Influential People in AI. (0:00) intro (0:50) work practices that w…
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EP 94: Niraj Shah (CEO, Wayfair) Building To $10B in Home Decor Revenue
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Niraj Shah is the Co-founder and CEO of Wayfair. In this episode, Niraj shares Wayfair’s journey from a collection of 250 sites generating $500 million in revenue to a single, unified brand achieving over $10 billion in online sales of home goods and furniture. He explains the challenges of overseeing a vast e-commerce platform with more than 10,00…
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Ep 28: LangChain CEO Harrison Chase on the Current State of Eval and Agents and The LLM Apps that Will Define 2024
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1:04:44
Last week LangChain announced a $20M Series A led by Sequoia and released the paid version of LangSmith, which has already been used by 1K+ teams and driven 80K signups. On this week’s episode of Unsupervised Learning, we sat down with LangChain Co-Founder and CEO Harrison Chase to talk about the current state of LLM evaluation, observability, and …
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Parker Conrad (CEO, Rippling): The Zenefits Redemption Story That Led to Rippling ($11B)
1:15:52
1:15:52
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1:15:52
In this memorable episode from our podcast archives, we revisit our conversation with Parker Conrad, Co-Founder of Rippling and former CEO of Zenefits. Parker opens up about his entrepreneurial path, detailing everything from fundraising challenges to his departure from Zenefits and the founding of Rippling. We also discuss the dynamics between VCs…
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