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 best practices, Michael’s “60x rule”, and why high ownership to fund size is the main driver of returns. We also…

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, building a startup in the Midwest, and how to disagree with your team. We also get into Mike’s prior company Wisely…

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 advertisers. We get into working backwards from pockets of strong demand to find business ideas, how to establish ear…

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 into the early days of building Amplitude, when to go multi-product, how to construct your board as a startup, hi…

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. This conversation with Dan gets into the history of open source software, cloud computing, Linux, the software…

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 of the harder moments of the past six years. We hit on three main themes: authentication; lessons raising mult…

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. Filip takes us inside Verkada’s rapid growth to almost a billion in annual revenue, over 2,000 employees, and rais…

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, also known as EBT or SNAP, the government program that provides over $200 billion dollars per year in benefits th…

Despite record cybersecurity spending and AI-driven defenses, 2025 has seen more breaches than ever. Discover why trust in automation is failing, which threats are truly evolving, and what tactical shifts forward-thinking security teams are making to stay resilient.By Science & Tech

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 how Ed first got started angel investing, how he built up deal flow, why he’s historically kept a low profile, a…

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 actually lead to more fraud, and gets into the weeds of various tactics he’s learned building a technical platform…

Shadow AI is transforming business productivity while creating unprecedented security risks. Learn how to govern AI responsibly without stifling innovation.By Science & Tech

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 a glimpse into the future, and a look into the past, at a story of pure grit and determination, working seven …

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 firms you’ll ever come across, and we get into how it how it was inspired by a 16x fund based in Chattanooga,…

Imagine this: A company spends millions on advanced AI-driven security systems, yet it falls victim to a cyberattack because a single unpatched vulnerability was exploited. Sound familiar? That’s because most security incidents stem from a small set of overlooked risks—a perfect example of the Pareto Principle in action.…

Cybercriminals don’t hack systems—they hack minds. Discover how social engineers use psychology to manipulate trust and urgency, and how to protect yourself.By Science & Tech

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 revenue run rate in two months, making it one of the fastest growing products ever. But Eric will be the first to …

Can AI truly be trusted, or should it adopt the cybersecurity principles of Zero Trust? This in-depth analysis explores the debate, revealing AI security risks, Zero Trust applications, and a strategic approach to protecting AI-driven systems.By Science & Tech

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 talk through Equal’s thesis-driven model, employing a team of product owners, only investing in only 3 to 5 theme…

Better sleep isn’t just a wellness perk—it’s a performance necessity. A well-rested CISO is sharper, more strategic, and less prone to burnout. This guide presents five actionable tips designed specifically for cybersecurity leaders to optimize their rest without compromising vigilance.By Science & Tech

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 Airtable, Zapier, GitLab, Remote, Hubspot, Gusto, and Box. Fresh off raising his $160m Fund 1, we get into the opport…

Risk is an unavoidable element of life. Throughout history, people have faced uncertainties, from the dangers of war to the volatility of financial markets. The ability to assess, manage, and mitigate risk has been crucial in shaping societies, businesses, and technological advancements.By Science & Tech

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, and why he sold only 17 months after starting it. If you tuned into last week’s episode, Paul told us to never t…

Artificial intelligence (AI) is rapidly transforming the cybersecurity landscape, especially in North America. As cyber threats grow more sophisticated, organizations are turning to AI-driven solutions to stay ahead of malicious actors. From detecting breaches in real-time to predicting attacks before they occur, AI has emerged as a critical tool f…

Paul Klein is the Founder and CEO of Browserbase, building infrastructure for AI browsers. Our conversation gets into the future of software and AI agents, why authentication is a huge problem in AI, how the best infrastructure companies become product companies, and the memo he wrote that convinced him to start Browserbase despite not wanting to b…

You’re probably familiar with Baiju Bhatt’s work as the co-founder of Robinhood. But he’s also obsessed with space, and recently started Aetherflux, a space solar power company. We get into the physics of using lasers to beam solar power to the Earth, Aetherflux’s early roadmap, and how he went from zero to one going from building software to physi…

Sheel Mohnot is the Co-founder of Better Tomorrow Ventures, an early stage fintech focused fund leading rounds in pre-seed and seed-stage companies. Our conversation weaves through Sheel’s two decades of building and investing in fintech, starting BTV, and why they started a fintech-focused accelerator, The Mint. Fun facts on Sheel, he was a contes…

Chris Hulls is the co-founder and CEO of Life360, the social network for families. At the time of recording, its the 15th largest app in the US, with over $330 million in annual revenue, and valued at over $3 billion in the public markets. We go inside the two decade journey building Life360, competing against Sam Altman and Woz, almost getting can…

Joseph Nelson is the Co-founder and CEO of Roboflow, making the world programmable by building computer vision tools for developers and enterprises. We talk about how computer vision creates a new paradigm to program the world, and how visual AI is the missing piece of AGI. Joseph also shares multiple live product examples, how computer vision unlo…

Austin Rief is the Co-founder & CEO of Morning Brew, building the Wall Street Journal for the next generation. They started the company in 2017, and grew it to 6 million subscribers and $70 million in revenue in six years. We talk through the journey starting Morning Brew with Co-founder Alex Lieberman while students at the University of Michigan, …

Niels Hoven is the founder of Mentava, building software to accelerate kids’ education, starting with teaching two year old’s to read. We talk about how public education isn’t designed for ambitious kids, the power of hater marketing, product design from zero to one, how too much data leads to Frankenstein products, Seed stage fundraising advice, p…

Nirav Tolia is the co-founder and two-time CEO of Nextdoor. He started the company in 2011, stepped down as CEO in 2018, watched the company go public in 2021, and re-joined as CEO the summer of 2024. He also founded Epinions which IPO’d in 2004, and before that was an early employee at Yahoo. We go inside the decision to re-join the company after …

Nakul Mandan is the founder of Audacious Ventures. Prior to Audacious, he was a partner at Lightspeed, joining from Battery, which he joined in ‘09 in the middle of the financial crisis while living in India. This conversation explores his journey immigrating to Silicon Valley and building an early stage venture firm from the ground up. We get into…

Jenny Fleiss is the Co-founder of Rent the Runway, and more recently started Roll Rider with her three kids. We get into the early insights that led to Rent the Runway, building the company with no fashion or tech background, fundraising advice, what she’s thinking about the future of AI and commerce, and the latest company she’s building with her …

Daryna Kulya is the Co-founder of OpenPhone, the world’s best business phone This episode is a masterclass on startup marketing, chronicling the first six years of OpenPhone, how they acquired their first customers, and inside all the different channels they used to scale the business to over 100k customers, including FB Groups, Reddit, SEO, and co…

Lisa Rapuano outperformed the market 15 years in a row in the 90’s and 2000’s. We go deep on how she did it, including early investments in AOL, Dell, and owning 24% of Amazon in 2002. She shares what she learned from Jeff Bezos and Michael Dell, what makes a good investor, plus her experience as a startup CFO and how it influenced how she thinks a…

Gokul Rajaram is an early stage technology investor. As a product leader, operator and board member, he’s helped build seven generational technology companies, including Alphabet, Block, Coinbase, DoorDash, Meta, Pinterest, and The Trade Desk. We talk about lessons learned from Zuck, Sergey Brin, and Jack Dorsey, when big acquisitions can go well, …

Guy Podjarny is the founder of Blaze, Snyk, and now Tessl. He’s spent decades building at the center of developers and security. His newest company Tessl is reimagining software development, helping shape a new paradigm he calls AI Native Development. We talk through his four quadrant framework for building and investing in AI, plus go into the ear…

Chris Hladczuk is the Co-founder and CEO of Hanover, where he’s building 1-click migration and 1-minute time to value fund administration for the $8 trillion in private market assets. Chris takes us through his story of building an audience online at nights while working at Goldman, breaking into tech and going from an IC to Chief Revenue Officer a…

Charley Ma and Mahdi Raza are the Co-founders of Pathlight Ventures, and were early employees at five unicorns, Plaid, Ramp, Alloy, Robinhood, and Stytch. They share tactical advice for early stage startup employees, lessons getting Plaid and Ramp their first customers, and deciding to build Pathlight together. Timestamps (00:00) Intro (02:30) Grow…

Building an enterprise-ready SaaS app? WorkOS has got you covered with easy-to-integrate APIs for SAML, SCIM, and more. Start now at https://bit.ly/WorkOS-Turpentine-Network. He’s had six near death experiences, and we talk about how those influenced him throughout life. We also talk about some of his early businesses, including one that had the FB…

Bobby DeSimone is the Founder and CEO of Pomerium, the best way to authenticate, authorize, monitor, and secure user access to any application without a VPN. Bobby explains why access control is so important, how it led to the biggest corporate hack ever, how its related to the day CrowdStrike took down the global economy, and how AI will change se…

Tyler Denk is the Co-founder and CEO of beehiiv, the newsletter platform built for growth. We go inside beehiiv’s early days, including joining MorningBrew as the second employee, lessons scaling to 3.5 million subscribers, the $75 million sale to Business Insider, and why I didn’t invest in beehiiv despite being an early customer. Tyler takes us i…

Michelle Valentine is the Co-founder and CEO of Anrok, the sales tax platform for software companies. We talked trends in software consolidation, lessons working with Anrok’s first customers, advice on fundraising, scaling a sales team, and early tricks for founders to avoid future tax-related headaches. Timestamps (00:00) Intro(02:19) The trend of…

Building an enterprise-ready SaaS app? WorkOS has got you covered with easy-to-integrate APIs for SAML, SCIM, and more. Start now at https://bit.ly/WorkOS-Turpentine-Network.Aaron Rubin is the Founder and CEO of ShipHero, a warehouse management system for brands and 3PL providers.We talk through Aaron’s journey building ShipHero, starting with what…

Logan Bartlett is a Managing Director at Redpoint. If you like startups and you listen to podcasts, you’re probably familiar with his podcast, the Logan Bartlett Show. We talk about how it first got started, plus all his tricks for growing the podcast, including his canonical episodes in 2022 that helped pop the web3 bubble. We also talk market cyc…

Ryan Denehy is the founder and CEO of Electric, software that helps businesses manage their IT and IT support. We talk through his first two startups from founding to exit, the early days of getting Electric off the ground, and Ryan’s frameworks for fundraising, recruiting, and sales. Timestamps:(00:00) Intro(03:05) Building an ad network for extre…

Get first-party targeting with Brave's private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign.Warp: Don’t let payroll and compliance hold your startup back: visit https://join…

Warp: Don’t let payroll and compliance hold your startup back: visit https://www.joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll. Get first-party targeting with Brave's private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to brave.com/brav…

Warp: Don’t let payroll and compliance hold your startup back: visit https://joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll. Get first-party targeting with Brave's private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/…