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/…

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/…

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeelWarp: 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.Melissa Cash is the Co-founder and CEO of Pok Pok, a montessori-inspired collection of digital toys that spark creat…

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Ed Sim is the Founder of boldstart ventures, which partners with bold founders reinventing the enterprise stack at the inception stage. Ed takes us inside the journey building boldstart, from its first $1m fund in 2010 up to $850m in AUM today. Timestamps:(00:00) Intro(03:48) Evolut…

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Nilam Ganenthiran is the founder and CEO of Beacon Software. Previously, he was the 12th employee and President at Instacart. We talk tactics for customer research, building customer relationships, balancing strategy and execution, how to serve on and manage a board, what happened w…

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Ankur Goyal is the Founder and CEO of Braintrust, the end to end developer platform for building the world's best AI products. Their customers include companies like Instacart, Zapier, Notion, Airtable, Replit, and more. We hit on the importance of LLM evals, advice for building AI …

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeelAlan Feld is the Founder and Managing Partner of Vintage Investment Partners. Vintage is one of the largest fund of funds in the world, managing over $4 billion across what is mostly investments into other venture funds, plus some secondary and direct startup investments at the growt…

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Anu Sharma is the Co-founder and CEO of Millie, building a better care system from the inside out. Our conversation covers the existing maternal health system, how Millie is reinventing it, and how to succeed building a healthcare company. Timestamps:(00:00) Intro(03:16) Problems in…

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Aaron Levie is a co-founder and the CEO of Box. This conversation covers opportunities in AI, the early days of Box, and lessons Aaron's learned on his founder journey. Timestamps(00:00) Intro(03:11) Why ChatGPT was an iPhone moment(04:37) Advice for large companies incorporating AI…

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 Attio, the next generation of CRM: https://bit.ly/AttioThePeelElad Gil is the founder of Color Genomics and Mixer Labs, which he sold to Twitter, and an early investor in iconic …

This episode is brought to you by Warp. Don’t let payroll and compliance hold your startup back: visit https://joinwarp.com/peel to get started and receive a $1000 gift card when you first run payroll. Celine Halioua is the founder and CEO of Loyal, a biotech company developing medicine to help dogs live longer and healthier lives. And dogs are jus…

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeelRahul Sonwalkar is the founder and CEO of Julius, an AI data scientist.He takes us inside his epic “Ligma Johnson” prank where he pretended to be fired from Twitter the day Elon acquired the company. He then goes inside his journey of building Julius, sharing lessons learned along th…

Brought to you by Attio, the next generation of CRM: https://bit.ly/AttioThePeelBill Shufelt is the Founder and CEO of Athletic Brewing, the craft brewer that created the non-alcohol beer market in the US.Bill takes us inside the early days of starting the company, including realizing there was an opportunity to make non-alcoholic beer, finding a c…

Dane Atkinson is the Founder and CEO of Odeko, the all-in-one operations partner for local businesses.Dane has spent his entire career helping small businesses. This episode is a masterclass on selling to SMBs. He shares all his lessons learned as a founder, and how Odeko survived zero revenue during COVID and hit $150 million in revenue two years …

Josh Miller is CEO and co-founder of The Browser Company, which is building a new internet browser. He explains why effective hiring requires caring a lot and trusting your taste and why Arc Search, a default mobile browser, could be The Browser Company’s next act. TIMESTAMPS: (00:00:00) Intro (00:02:35) Working for Obama (00:03:55) Giving up 8-fig…

Subscribe to my newsletter The Split for new episodes emailed every week: https://www.thespl.it/ Brought to you by Attio, the next generation of CRM: https://bit.ly/AttioThePeelPeter Walker is Head of Insights at Carta and writes a newsletter called “The Data Minute”, a weekly newsletter highlighting data from over 43,000 private tech companies tha…

Subscribe to my newsletter The Split for new episodes emailed every week: https://www.thespl.it/ Chris Bakke has founded and sold three companies for between $25-100 million to Zillow, Indeed, and most recently Twitter / X. He shares how he convinced Elon to buy his company, what it's like working for Elon, exactly how the Twitter algorithm works, …

Subscribe to my newsletter The Split for new episodes emailed every week: https://www.thespl.it/ Brought to you by Attio, the next generation of CRM: https://bit.ly/AttioThePeelMike is currently a partner at Lightspeed Venture Partners. Before Lightspeed, he spent five years building Anchor, which he sold to Spotify in 2020, and then led Spotify’s …

Eric Newcomer is the founder of Newcomer, a publication he launched in October of 2020 to cover the business of startups and venture capital. He had just left Bloomberg after nearly six years, and was previously the first employee at The Information. — — — — Timestamps: (00:00) Intro (02:46) The current state of media (05:59) Anchoring his 4th grad…

Siqi Chen is the Co-Founder and CEO of Runway, the modern and intuitive way to model, plan, and align your business for everyone on your team. Or, in Siqi’s words, “revolutionizing the $80 trillion business industry”. A few months ago, Runway’s new website went viral across the internet. Siqi takes us inside how that happened. He’s no stranger to g…

Shrav Mehta is the Founder and CEO of Secureframe, which empowers businesses to build trust with customers by automating information security and compliance. Shrav started the company in 2019 after being an early employee at Scale, Pilot, Lob, and Hired, and has since raised from investors like Kleiner Perkins, Backend Capital, Soma Capital, and Ba…

Kevin Espiritu is the founder and CEO of Epic Gardening, which is, by multiple measures, one of the largest brands in gardening on the planet.What started in 2013 as a blog has since evolved into a gardening empire spanning YouTube, TikTok, Instagram, Facebook, 4,500 gardening stores, and three gardening books. Epic raised a $17.5m Series A from Th…

Kirsten Green is the founder of Forerunner Ventures, a venture capital firm that focuses on understanding the mindset of the modern consumer. Kirsten started Forerunner in 2010, and was an early investor in companies like Faire, Chime, Warby Parker, Dollar Shave Club, Hims, Glossier, Jet, Bonobos, HotelTonight, and The Farmer’s Dog.This episode tak…

Craig Fuller is the Founder and CEO of FreightWaves, a media company and data provider for the global supply chain. He’s also the CEO of Flying Media Group, which he founded in 2021 to acquire Flying Magazine, the largest US-based print magazine for the aviation industry. This conversation is split into three parts: a crash course on logistics and …

Danielle Cohen-Shohet is the CEO and Founder of GlossGenius, the all-in-one booking, payments and POS solution that helps beauty and wellness professionals drive bookings and grow their business. Danielle started the company in 2016 and has since grown it to a $510 million valuation. This is while taking a disciplined approach to fundraising, raisi…

Cristina Junqueira is the co-founder of Nubank, the largest neobank in Latin America – and in the world – with more than 80 million customers. She is also the second self-made female billionaire in Brazil. Cristina and her co-founders David Vélez and Edward Wible launched Nubank in 2013, essentially building the fintech category in a market where i…

Sid Yadav is the Co-founder and CEO of Circle, the all-in-one community platform trusted by creators like Tiago Forte, David Perell, and Miles Snider. Sid started the tech blog Rev2 when he was a teenager in New Zealand, writing about the launch of YouTube and the iPhone. He was the founding engineer and designer of Teachable, which he helped scale…

Pim de Witte is the Co-founder and CEO of Medal, which enables millions of gamers to capture and share their favorite gaming moments with friends. Pim started the company in 2015 and has since raised over $72 million, supported by investors like OMERS Ventures, Makers Fund, Dune Ventures, and Horizon Ventures.Brought to you by Secureframe, the auto…

Itai Damti is the Co-founder and CEO of Unit, the platform that helps leading tech companies store, move, and lend money.Unit has raised over $170 million from investors like Better Tomorrow Ventures, Accel, Insight, and dozens of angels. — In this episode, we discuss: The first and second wave of fintech innovation How the second wave brings finan…

Kevin Liu is the Co-founder and CEO of Metronome, which enables software companies to launch, iterate, and scale their business models with billing infrastructure that works at any size and stage. Prior to Metronome, Kevin and his co-founder Scott Woody both sold their respective separate companies to Dropbox. Kevin and Scott started Metronome in 2…

Wade Foster is the Co-founder and CEO of Zapier, an automation platform that helps you work faster. Wade and his co-founders Mike and Bryan started the company in 2011, and have always done things a bit differently. From being a startup based in Missouri, working as a remote team since 2011, and raising very little outside capital despite being one…

Gaurab Chakrabarti and Sean Hunt are the Co-founders of Solugen, which replaces petroleum based products with plant-derived substitutes without sacrificing affordability or performance. They met playing poker in college, kickstarted the company with $10k from an MIT pitch competition, and have since scaled the business to over nine-figures in reven…