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The Ocean: Earth’s $2.5 Trillion Last Frontier | Will O’Brien, Co-founder of Ulysses
Will O’Brien is the Co-founder of Ulysses, building autonomous, low cost robots for the ocean. Will considers the ocean humanity’s next great frontier. It makes up over $2.5 trillion of economic activity, considering things like fishing, aq
How to Build a Content Strategy + CPG Brand Lessons | Isaac Medeiros (Mini Katana, Kanpai Foods)
Isaac Medeiros is the Founder of Mini Katana and Kanpai Foods. Isaac’s content gets over 1 billion views per month. Our conversation gets into content strategy from a high level down to tactical decisions, differences between the TikTok and
The Past, Present, and Future of AI, Robotics, Venture Capital, Crypto | Why Deep Tech Startups Mess up Value Capture | Michael Dempsey, Managing Partner, Compound
Michael Dempsey is the Managing Partner at Compound, a thesis-driven, research-centric investment firm. We spent two hours talking through the past, present, and future of a bunch of topics in technology and investing. Michael started inves
Ryan Hoover on Growth Flywheels, Building Communities, Helping Founders, LP Investing
Subscribe to my newsletter (https://www.thespl.it) to get every episode + the transcript in your inbox every week. Ryan Hoover is the Founder of Product Hunt and Weekend Fund. Ryan’s probably helped more founders launch their products than
PhD to $100M Revenue: Rebuilding SMB Lending with AI | Sahill Poddar, Co-founder and CEO of Parafin
Sahill Poddar is the Co-founder and CEO of Parafin, helping marketplaces, vertical SaaS, and point of sale providers offer financial services their merchants. Sahill and his team have quietly built Parafin to nearly a $100m GAAP revenue run
Sleeping in Parking Lots to $250M+ Revenue: How Handshake Built Gen Z's Career Platform, Inside its Fast Growing AI Data Labeling Business, Scaling a Three-Sided Marketplace, How AI Changes Hiring
Garrett Lord is the Co-founder and CEO of Handshake, the career and social network for Gen Z, connecting a million employers, 1,600 universities, and 18 million students and alumni. We talk through the explosive growth in Handshake’s human
Solving the Hardest Problems in Dev Tools | Jake Cooper, Founder of Railway
Jake Cooper is the Founder of Railway. This conversation explores how AI accelerates the need for strong backend infrastructure, when to build vs buy in AI software, and why there are only two moats: solving hard problems and doing hard thi
How WordPress Powers 43% of the Internet | Matt Mullenweg, Co-founder and CEO, Automattic
Today’s guest is Matt Mullenweg, Co-founder of WordPress, which powers over 43% of all websites on the internet, and founder of Automattic. Our conversation explores the 2000’s internet, the early days of Automattic, and the decisions and p
Gamma's Journey to $50M ARR with 30 Employees | Co-founder and CEO Grant Lee
Grant Lee is the Co-founder & CEO of Gamma, building instant PowerPoints, presentations, and websites with AI. As someone who’s made a lot of decks, its refreshing how Gamma thinks about slides starting with the words and narrative, using A
Inside the $2 Trillion Employee Benefits Market | Ryan Sachtjen, Threeflow
Ryan Sachtjen is the Co-founder and CEO of Threeflow, building software for employee benefits brokers and insurance carriers. We start with a deep dive into the nearly $2 trillion dollar employee benefits market, including the structural is
How to Raise a VC Fund Today, Traits of Top Emerging Managers, Why Everyone is Selling Secondaries, Triple-Layered SPVs | Samir Kaji, Co-founder and CEO of Allocate
Samir Kaji is the Co-founder and CEO of Allocate. This conversation is a deep dive into the private markets, the evolution of venture capital as an asset class, and how there are now 10x more private investment firms than public companies.
How to Skip Your Seed, Pre-Seed Lessons Building Afore to $500M+ AUM | Anamitra Banerji
Anamitra Banerji is the Co-founder of Afore Capital, an SF-based VC firm that specializes in investing in pre-seed stage companies. Our conversation gets into the evolution of Pre-Seed as a category, why Pre-Seed is more than option checks,
Benchmark’s Eric Vishria on Going Zero to $100M ARR in 12 Months, Archetypes of Top AI Founders, Why Storytelling is a Superpower, How Benchmark Makes New Investments
Eric Vishria is a General Partner at Benchmark Capital. Our conversation goes inside the new class of startups going zero to $100 million ARR in 12 months, the ways AI is changing company building, and how Eric and Benchmark make new invest
Samsara’s Journey to $26B Public Company | Sanjit Biswas, Co-founder and CEO
Sanjit Biswas is the Co-founder and CEO of Samsara, the fleet management and safety platform. At the time of publication, Samsara is a public company worth over $26 billion, and we unpack how exactly they went from zero to run rating at ove
Michael Kim @ Cendana | Lessons from the Top VCs, How Cendana Does Diligence, Portfolio Construction Best Practices, the 60x Rule, How Seed Funds Compete vs Multi-stage, Inside Cendana's Early Days
Michael Kim is the Founder of Cendana Capital, a fund of funds that makes anchor investments in very early stage VC funds. We talk characteristics of the best investors, how Cendana does diligence on fund managers, portfolio construction be
How AI Changes Governments & Business Models, From $11 to $187M Exit | Mike Vichich, Pursuit
Mike Vichich is the Co-founder and CEO of Pursuit, which helps companies generate more revenue from the public sector. We talk about how AI is changing Helmer’s 7 Powers, how it’s impacting the government, if DOGE is actually working, build
Ultimate Startup Growth Playbook, Using AI to Automate Operations | Sam Ross, Numeral
Sam Ross is the Co-founder and CEO of Numeral. This conversation is a master class on all things growth at the zero to one stage. We talk early growth lessons from Airbnb, and stories from being one of the largest, earliest Facebook adverti
Scaling Amplitude to $300M ARR with Co-founder and CEO Spenser Skates
Spenser Skates is the Co-founder and CEO of Amplitude. Our conversation gets into the importance of data in product design and company building, how Amplitude is thinking about AI, and the future of user responsive software. We also get int
Lessons Going Zero to $40M ARR in Two Years | Dan Lorenc, Chainguard
Dan Lorenc is the Co-founder and CEO of Chainguard, the safe source for open source. The internet runs on free, open source software. But as its risen in popularity, its become the latest attack point targeted by hackers and nation states.
Surviving Two Seed Extensions, Fixing Auth for AI Agents | Clerk Founder & CEO Colin Sidoti
Colin Sidoti is the Co-founder and CEO of Clerk, the best way to build authentication and user management. I loved this conversation, because Colin is currently in the arena building Clerk. It has not been easy, and he takes us inside some
Building Verkada, the $4.5B Physical Security Company | Filip Kaliszan, Founder and CEO
Filip Kaliszan is the Founder & CEO of Verkada, the physical security company. Verkada started in 2016 by building the best camera for physical security teams, and has since evolved into a full suite of security products for buildings. Fili
Forage: The Trillion Dollar Opportunity in Restricted Payments | Ofek Lavian
Ofek Lavian is the Co-founder and CEO of Forage, the mission driven payments company. This is a special episode, because I’m an investor in Forage, and Ofek shares everything he’s learned building the company. We go deep on food stamps, als
How the World’s Most Active Angel Investor Operates | Ed Lando, Founder of Pareto Holdings
Ed Lando is the Co-founder of Pareto, where he’s been an early investor in over 25 unicorns, started and incubated over 10 companies, and was recently named the most active angel investor in the world according to Crunchbase. We get into ho
Alloy’s Unconventional Path to $1.5B with Tommy Nicholas, Co-founder and CEO
Tommy Nicholas is the Co-founder and CEO of Alloy, the identity and fraud prevention platform trusted by over 700 financial service companies. Our conversation explores the early days of fintech, why more consumer financial protections actu
The $750 Billion AI Opportunity in Customer Service | Mike Murchison, Co-founder and CEO of Ada
Mike Murchison is the Co-founder and CEO of Ada, the AI-powered customer service automation platform. Ada’s product and scale puts Mike at the forefront at how AI is changing software and labor markets, and this conversation felt like both
Why Founders are Moving to Chattanooga, Tennessee to Lock-in | Cam Doody at Brickyard
Cam Doody is the Co-founder and General Partner of Brickyard, the venture capital firm moving founders to Chattanooga, Tennessee to lock-in with no distractions until they find product market fit. Brickyard is one of the most unique venture
Zero to $20m ARR in Two Months: Inside Bolt’s 7-Year Journey to Overnight Success | Eric Simons, Co-founder & CEO
Eric Simons is the Co-founder and CEO of StackBlitz, best known for its breakout product Bolt, letting anyone build full stack apps from text, in the browser. Bolt launched in October of 2024, quickly growing from zero to a $20 million reve
Rick Zullo on Building Equal Ventures, Why Traction is Overrated, Advice for Emerging Managers
Rick Zullo is the Founder of Equal Ventures. Our conversation gets into Equal’s unique approach to venture capital, thinking more like public market and private equity investors, and why they also think traction is overrated at Seed. We tal
Illegal Immigrant to $160m Fund 1: Inside Villi Iltchev’s Journey Building Category Ventures
Villi Iltchev is the founder of Category Ventures, where he invests early in enterprise software startups. And he’s done it longer than almost anyone, building Salesforce’s corporate venture arm and investing early in companies like Airtabl
Govtech + Drones Crash Course, Lessons From 2 Exits | Rahul Sidhu
Rahul Sidhu is the co-founder of SPIDRTech and Aerodome, two companies in the public safety space. He’s sold both of them, and our conversation unpacks all the lessons he learned, what he did differently with his second company Aerodome, an
