The Peel with Turner Novak

Eoghan McCabe is the Co-founder and CEO of Intercom, building Fin.ai, the AI customer service company.This was an extremely candid, two hour conversation going inside every detail of how Intercom was the first late stage software company to successfully re-architect itself to be AI-native.Intercom just announced they’ve built their own customer service-focused AI models, and Eoghan explains why most software companies will have to do the same.We also talk through the lessons he learned coming back to run Intercom in 2022 after stepping back in 2020, why many AI companies have strong negative gross margins despite the narrative, how Intercom designed AI’s first outcome-based pricing model, the challenges of buying AI software today, the importance of brand when building new products, and we get in the wayback machine, talking through the pain raising Intercom’s initial million dollar Seed round, and how venture capital has changed since then.Thank you to Eoghan’s Co-founder Des Traynor for helping me brainstorm topics for the conversation.Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeelTimestamps:(4:18) We’re at peak SaaS(9:11) Inside early days of Intercom’s turnaround(16:43) AI will beat humans at everything(21:17) Making trade-offs building AI products(24:25) Why Intercom trained their own AI models(28:33) Lessons from returning as CEO(34:19) Overcoming initial AI skepticism in 2022(40:02) Creating AI’s first outcome-based pricing(45:15) Intercom’s best-in-class gross margins(49:25) Why its so hard to buy AI software today(51:28) Unpacking AI’s negative gross margins(58:12) Being perfectly positioned for AI(1:09:47) Why AI products need their own brand(1:16:13) Founder CEOs vs Manager CEOs in AI(1:21:29) AI startup opportunities(1:24:57) Lessons running a team in Dublin and SF(1:28:25) How media has changed over time(1:37:32) Raising Intercom’s first $1 million Seed round(1:43:53) Why there are so many VC’s(1:47:38) Advice for investorsReferencedIntercom: https://www.intercom.com/Fin: https://fin.ai/Intercom Careers: https://www.intercom.com/careersEoghan’s website: https://eoghanmccabe.comIntercom’s first pitch deck: https://www.slideshare.net/slideshow/intercompitchdeckpdf/253317574Follow EoghanTwitter: https://x.com/eoghanLinkedIn: https://www.linkedin.com/in/eoghanmccabeFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

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 supply chain, how AI will impact it, and what the next big cyber attack will look like.Dan is an engineer, but he also loves sales and go-to-market. We unpack how Chainguard went from zero to 150 customers and a $40m ARR in two years.Chainguard just announced a $350 million Series D led by Kleiner and IVP, and Dan unpacks the round, plus shares his secret methodology for valuing the company.A big thank you to Dan’s Co-founder Kim Lewandowski, to Clay Fisher @ Spark, Bogomil Balkansky & Andrew Reed @ Sequoia, and Tom Loverro @ IVP for their help brainstorming topics for Dan.Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeelTimestamps:(3:26) A safe source for open source(4:57) The software supply chain(7:19) Can you trust open source code with contributors in Russia?(9:43) Malware attack that almost took down the entire internet(12:40) What the next big cyber attack will look like(15:12) How will AI impact the software supply chain(17:53) The history of cloud computing(21:42) Why all cloud computing runs on Linux(23:16) How Linux + Linux distros work(29:28) Automating open source security(32:43) Chainguard roadmap: Libraries and VMs(36:40) Focusing on FedRAMP(42:44) Impact of DOGE(44:06) Zero to $40m ARR in two years(45:40) Learning to love sales as a technical founder(47:24) Lessons from Frank Slootman(51:15) How to create urgency in sales(53:16) How to build a sales team(58:23) Hiring Ryan Carlson from Wiz & Okta(1:01:45) Inside Chainguard’s $350m Series D(1:07:41) Vibe coding + Dan’s software stack(1:09:51) Cutting his hair in front of the entire company(1:10:27) Wearing a different suit to each board meeting(1:12:32) Bogomil, world’s best SDRReferencedCheck out Chainguard: https://www.chainguard.dev/Jobs at Chainguard: https://www.chainguard.dev/careersPrior episode with Dan: https://www.youtube.com/watch?v=AC4cOJ9n_Z8Linux Origin Email: https://www.reddit.com/r/linux/comments/mmmlh3/linux_has_a_interested_history_this_is_one_of/The Qualified Sales Leader: https://www.amazon.com/Qualified-Sales-Leader-Proven-Lessons/dp/0578895064Julius, AI data analysis: https://julius.ai/Claude Code: https://www.anthropic.com/claude-codeWorld’s best SDR: https://x.com/BogieBalkansky/status/19132697148828143502025 Chainguard Assemble Keynote: https://www.youtube.com/watch?v=adfU9LJg3I0Follow DanTwitter: https://x.com/lorenc_danLinkedIn: https://www.linkedin.com/in/danlorenc/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Austin Petersmith is the Co-founder and CEO of Howie, the AI secretary.We talk about why AI assistants are so hard to build, why they decided to build Howie super narrow, and everything that went into their brand, name, and viral launch.Thank you to Adam D’Augelli, Sophia Amoruso and Alex Cohen for help brainstorming topics for the conversation.Thank you to Hanover Park for supporting this episode. Try the modern, AI-native fund admin at https://www.hanoverpark.com/TurnerTimestamps:(3:35) Howie: The AI Secretary(6:08) Why AI assistants are so hard to build(16:19) Why Howie started in email(20:49) Adding a human in the loop(30:48) AI software vs AI-powered humans(36:21) How a meme inspired Howie(39:29) Inside the making of Howie’s launch video(44:15) Howie’s viral launch video + Discussion(53:47) Designing the brand(1:01:37) Long-term opportunity and roadmap(1:07:53) Working for Jason Calacanis(1:12:00) Jason's media lessons(1:16:51) Getting Howie's first users(1:19:35) Pitch deck strategy that raised $6m(1:24:09) The mistake of optimizing for growth too soon(1:29:48) Building an AI company outside of SF(1:33:13) Being Superhuman’s 1st customer, Mercury’s 3rdReferencedTry Howie: https://howie.com/Jobs at Howie: https://app.dover.com/jobs/howieHowie Dewitt Meme: https://knowyourmeme.com/memes/howie-dewittNewKid: https://newkid.services/Follow AustinTwitter: https://x.com/awwstnLinkedIn: https://www.linkedin.com/in/awwstnFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Chris Frantz is the Co-founder and CEO of Loops, the email platform for software companies.We get into why sending emails is still a big problem, his hilariously simple framework for building products, getting in to YC with a last minute application, and why they skipped raising a Series A.We also talk through Chris decade of working in marketing, like when to lean into PLG vs Sales vs hype led growth, early stunts they did to get their first users, why they do no marketing now, and why Loops’ customer support team is all engineers.Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeelTry Hanover Park - the modern, AI-native fund admin https://www.hanoverpark.com/TurnerTimestamps:(4:37) Email for software companies(8:28) Why email is a big deal(14:05) The future of email(17:00) Product vs Sales vs Hype led growth(24:33) Coming up with the idea for Loops(29:36) Building one of the first GPT wrappers in 2020(34:34) Lessons selling his first company(37:13) Doing their YC app in 10 minutes(40:53) Avoiding VC’s who add value(46:58) Skipping a Series A(51:37) Building in stealth for 18 months(53:21) Marketing stunts to get the first waitlist sign-ups(58:44) Four step cadence of building Loops(1:01:58) Personally onboarding every new customer(1:04:03) Balancing 996 with family(1:11:11) Cleaning wasp nests with a shop vacReferencedLoops: https://loops.soCareers at Loops: https://loops.so/careersCuriosity: https://curiositystream.comSnazzy AI / Unbounce: https://unbounce.com/product/smart-copyAtlas customer support: https://atlas.soFollow ChrisTwitter: https://x.com/frantzfriesLinkedIn: https://www.linkedin.com/in/ctfrantzFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Dan Gray is the Head of Insights at Equidam.If you’re a tech and investing nerd like us, you’ll love this conversation. We cover everything Dan’s learned reading dozens of academic research papers on startups and venture capital, debunking many popular narratives of the industry.We talk about the dangers of pre-mature startup scaling, the importance of origination stage investing, the concept of startup catering and why so many startups look the same, and the role of mega funds play in the ecosystem.We also discuss what the data says about concentration vs diversification, what VC’s get wrong about pattern matching, and why pivoting is more valuable than you thinkThanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeelTry Harmonic - The startup discovery engine https://harmonic.ai/turnerTimestamps:(6:43) What’s the required rate of return in VC?(9:29) Venture capital needs new definitions(16:10) QSBS(18:23) Are we in an AI bubble?(24:07) Re-branding early and late stage venture(28:25) We need more origination stage capital(40:05) Survivorship bias in emerging manager outperformance(42:57) Incentives driving larger fund sizes(48:10) Raising overvalued rounds re-risks a startup(52:08) Startup catering: why all startups look alike(58:42) Are VC mega funds still an experiment?(1:08:06) Late stage VC is competing with PE(1:13:42) a16z’s Fund 1 strategy(1:18:18) How diversified should VC funds be?(1:25:06) Performance of Generalist vs Specialist firms(1:30:35) How to value a startup(1:40:58) Why VC firm location correlates to returns, but startup location does not(1:44:05) Founder background doesn’t predict success(1:48:27) Startups with one pivot are most successful(1:50:24) Premature scaling kills 70% of startups(1:54:47) Does mega fund model work for origination investing?(1:56:15) Value of Twitter and writing onlineReferenced Research PapersVenture Predation: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4437360Process Alpha: https://angelspan.com/process-alpha-how-to-construct-and-manage-optimized-venture-portfolios-joe-milam-journal-of-portfolio-management-august-2022/The Sunk Cost Fallacy in VC: https://www.sciencedirect.com/science/article/pii/S0929119924000518Predictably Bad Investments in VC: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4135861Startup Catering to Venture Capitalists: https://afajof.org/management/viewp.php?n=58968Premature Scaling: https://innovationfootprints.com/wp-content/uploads/2015/07/startup-genome-report-extra-on-premature-scaling.pdfReferenced BooksThe Otherland Tetrology: https://www.goodreads.com/series/43762-otherlandPermutation City: https://www.goodreads.com/book/show/156784.Permutation_City?from_search=true&from_srp=true&qid=lf7FuUR9se&rank=1Necromancer: https://www.goodreads.com/book/show/6088007-neuromancer?ref=nav_sb_ss_1_29Other Referenced ItemsQSBS changes: https://www.dwt.com/blogs/startup-law-blog/2025/07/qsbs-big-beautiful-bill-tax-code-upgradesMega funds and the great re-risking: https://nextview.vc/blog/megafunds-and-the-great-re-risking/Rex Woodbury’s post on hot companies: https://www.digitalnative.tech/p/the-taxi-cab-theory-of-venture-capitalThe VC Performance Paradox: https://www.linkedin.com/pulse/performance-paradox-venture-capital-dan-gray-2fqrePrior episodes mentionedDan Feder: https://youtu.be/_Ou6D9PLSBIMichael Dempsey: https://youtu.be/UzSbG6DL8CMSolugen: https://youtu.be/ofkNiB2nI3QFollow DanTwitter: https://x.com/credistickBlog: https://credistick.comFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Dan Feder is a Senior Managing Director of Investments at the University of Michigan’s $18 billion endowment.Our two hour conversation talks through the past, present, and future of all things venture capital, and investing more broadly.Dan lays out the case for why most institutional investors should change how they approach asset allocation, why risk and uncertainty are not the same, the importance of relevance and independent thinking, advice for fund managers raising from institutional LP’s, the trend of VC’s rolling up services businesses, and what he learned from beating Lance Armstrong in a race.Thanks to Chris Douvos @ Ahoy Capital and Adam Kurkiewicz at WashU for their brainstorming topics for Dan!Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeelTry Hanover Park - the modern, AI-native fund admin https://www.hanoverpark.com/TurnerTimestamps:(5:50) Beating Lance Armstrong in a race(8:05) “The will to win is nothing without the will to prepare”(10:39) Why investors need to re-think asset allocation(22:31) Difference between risk and uncertainty(29:26) How endowments work(33:12) Endowment portfolio construction(40:47) From law, to industrial buyouts, to venture(49:13) Narrowing scope to increase returns(54:54) Why career planning as an LP is hard(58:24) VC in the 00’s(1:08:18) Venture vs Adventure Capital(1:15:16) VC’s rolling up legacy industries(1:20:17) Importance of relevance(1:26:25) Traits of the top investors(1:28:25) Importance of trust in institutional LP fundraising(1:32:54) Venture is the most competitive ass class(1:35:37) Why venture firms do not persist over time(1:38:27) How venture will change going forward(1:43:37) The Newman CycleReferencedA Sense of Where You Are by John McPhee: https://www.amazon.com/Sense-Where-You-Are-Princeton/dp/0374526893Risk Uncertainty and Profit by Frank Knight: https://www.amazon.com/Risk-Uncertainty-Profit-Frank-Knight/dp/1614276390Follow DanTwitter: https://x.com/federdanLinkedIn: https://www.linkedin.com/in/danfederFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Albert Azout is the Co-founder and Managing Partner of Level Ventures, combining first-principles thinking with state-of-the-art data science to back and build top seed-stage firms and their breakout companies.Venture investing is hard, and this conversation covers all their research unpacking exactly how to generate alpha.We also talk about how Level picks and backs emerging venture managers to invest in, and Albert gives a demo of the custom internal software they’ve built.Thank you to Jake Kupperman, Sasha Kaletsky, Nathan Benaich, Amanda Robson, and Dave Fontenot for helping brainstorm topics for the conversation. Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeelTry Hanover Park - the modern, AI-native fund admin https://www.hanoverpark.com/TurnerTimestamps:(5:01) Top 3 forms of alpha in VC(10:11) Other ways to generate alpha(12:47) Avoiding false positives(17:11) Optimal fund size and portfolio construction(22:25) The role of Luck(23:55) Spin-out vs outsider funds(25:43) Level’s backchannel reference process(29:29) Finding alpha in Criticality Investing(34:45) Why capital flows drive all returns(43:53) Early, consensus investing has the most alpha(48:46) Networks are more persistent than performance(52:03) The strongest and weakest networks(58:41) Demo of Level’s internal software(1:04:48) Building a Fund of Funds around their data(1:10:01) Ideal LP GP relationship(1:12:39) Benchmarks are relative(1:15:39) VC funds using AI(1:17:43) How venture will change in the next 10 yearsReferencedLevel Ventures: https://levelvc.com/Level’s Research Papers: https://levelvc.com/research/Follow AlbertLinkedIn: https://www.linkedin.com/in/albertazout/Newsletter: https://albertazout.substack.com/ Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

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, aquaculture, shipping, mining, communications infrastructure, and defense. Yet we know more about the surface of the moon’s of Saturn than we do the bottom of our own ocean.We talk about Ulysses first product, restoring plant life in the ocean, their modular autonomous underwater robotics platform, advice for anyone selling to governments, crazy businesses that could eventually evolve in the ocean, and why the way we finance startups needs to change.Will also loves conspiracy theories, and we talk about some of our favorites, and why he thinks people who believe them could make good startup founders.Thank you to Will’s brother’s Harry and Jacob O’Brien, and to upcoming guest of the show Eoghan McCabe for helping brainstorm topics for Will.Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeelTimestamps:(4:03) Peace offering of Dubai Chocolate(5:30) Modern internet theory(7:40) The ocean is the last frontier(11:53) Ulysses: read/write layer of the ocean(13:35) The $2.5 trillion ocean economy(15:14) Current ocean unit economics(18:50) Starting with seagrass ecosystem restoration(24:13) Modular, underwater autonomous robots(27:31) Starting Ulysses with a group chat(29:51) Raising a Seed from Lowercarbon with no network off a cold calendar invite(32:24) Economic use cases for ocean robotics(36:07) Spiritual energy from the ocean(42:36) First Ramp podcast ad in Irish(43:21) Floating cities, sub tours, deep sea mining, iron fertilization(51:47) $10+ billion in shipwrecked treasure(53:18 Atlantis is real(59:46) Craziest alien conspiracy theories(1:01:28) Sinking the titanic to create the Fed(1:04:19) Conspiracy theory believers are good founders(1:07:55) How to sell to the government(1:13:28) Writing a letter to an Irish billionaire(1:16:00) Finding meaning after living with Monks in Nepal(1:27:10) Why financial innovation precludes economic dominance(1:44:01) The SPV peddler business model(1:46:35) Should we bring back SPAC’s?ReferencedUlysses: https://www.ulysses.eco/Careers at Ulysses: https://www.ulysses.eco/jobsThe Richat Structure: https://en.wikipedia.org/wiki/Richat_StructureJesse Michael’s YouTube: https://www.youtube.com/@JesseMichelsBrad Jacobs: https://en.wikipedia.org/wiki/Brad_Jacobs_(businessman)Follow WillTwitter: https://x.com/willobriLinkedIn: https://www.linkedin.com/in/will0brienFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

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 YouTube algorithms, and how AI will impact content creation.We also get into Isaac’s origin story building consumer brands, why TikTok made food an interesting category for new products, how to get a product into retail stores, and why you shouldn’t sell into retail.Isaac also shares how tariff’s impacted his company. They became unprofitable overnight, and he had to move his entire supply chain from the US to Mexico in 60 days.Thank you to Sean Frank @ Ridge and Kevin Espiritu @ Epic Gardening for their help brainstorming topics for Isaac.Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here.Timestamps:(3:46) 165 million views in two days(5:15) Followers don’t matter, build a binge bank(11:21) How to monetize an audience(14:36) Identify outliers for content ideas(17:13) Should founders make their own content?(19:34) Starting Mini Katana(23:39) $10m revenue in two years w/ $0 CAC(25:56) Difference between TikTok and YouTube algorithms(29:38) When to experiment with a second platform(32:20) Starting Kanpai, a freeze-dried candy company(36:54) Why freeze-dried candy wasn’t popular(38:22) Why you shouldn’t sell in retail(41:12) Why you should sell in retail(47:05) Downsides of selling to large retailers(49:52) Should CPG brands raise money?(57:59) Moving manufacturing from US to Mexico in 60 days due to tariffs(1:04:20) Why you don’t want to be first in a category(1:08:06) Other CPG creators Isaac follows(1:09:15) Elon Musk, Charlie Munger, Mark Cuban(1:11:55) Labubu’sReferencedMini KatanaKanpai FoodsPrevious episode with Kevin EspirituPrevious episode with Sean FrankPeachy BabiesThe Marshmellow CoFollow IsaacTwitterLinkedInFollow TurnerTwitter: LinkedIn: Subscribe to my newsletter to get every episode + the transcript in your inbox every week.

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 investing in AI in 2016. He was the first investor in now-unicorns Runway and Wayve. But he hasn’t done much AI investing over the past few years. We talk about why, how AI will intersect with robotics, the future of things like crypto and synthetic biology, and why so many deep tech companies mess up economic value capture.We also talk about what it means to be a thesis-driven venture firm, Compound’s research process and how to replicate it, what private and public market investors can learn from each other, advice for anyone starting in venture today, how to build a brand in VC, and why venture firms don’t compound and actually decay over time.Thank you to Kevin Kwok, Andy Weissman, Cristóbal Valenzuela, Blake Robbins, and Smac at Compound for their help brainstorming topics for this.Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here.Timestamps:(4:09) Leading Runway’s Seed in 2018(10:15) Short-term ARR vs long-term sustainability(16:20) Compound, a research-centric investment firm(18:41) Investing in bio, crypto, real-world AI, and healthcare(23:58) VC firms do not compound, they decay over time(29:27) How to build a research-focused investment firm(41:30) Current state of venture slop(45:43) Building a brand as a VC firm(52:31) Investing in Wayve in 2016(58:53) Why deep tech companies screw up economic value capture(1:04:57) How to approach massive funding rounds(1:08:36) Should VCs “play the game on the field”?(1:15:33) Compound is a forecasting firm(1:21:37) Advice for young people getting into VC(1:26:48) Public market investors underappreciate narratives(1:31:20) Michael’s crypto thesis + real use cases(1:40:07) Why crypto hasn’t seen mass adoption yet(1:49:00) Humanoid robots won’t work(1:54:42) Should you make a hyped launch video?ReferencedCompound RunwayWayveMichael’s BlogFollow MicahelTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

Subscribe to my newsletter 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 anyone else on Earth. We talk about starting Product Hunt as an email list, and he open sources the growth flywheel that propelled it to one of the most important places in technology.Ryan unpacks how he built and scaled a community around the product, how online communities have changed over time, how we’re thinking about software in the age of AI (tech will change, human behavior won’t), and how status has changed in Silicon Valley.We also talk about starting Weekend Fund to invest in other founders, his first 400x investment, investing in consumer health, and why he started investing in other funds.Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 signing-up here. Timestamps:(5:52) Helping founders with software(15:36) Early ideas for Product Hunt in 2013(19:14) Starting as a social email list(26:26) Product Hunt’s growth flywheel(31:15) AI won’t change human behavior(34:12) An audience is not a community(36:42) Why every community needs utility(38:52) Communities have shifted towards group chats(40:10) How AI changes building products(49:35) Importance of craft(52:30) Starting Weekend Fund, Ryan’s 400x investment(56:57) Weekend Fund’s software experiments(59:26) What makes Ryan’s investing unique(1:02:16) Why Ryan has a small fund(1:07:41) Peptides, GLP-1’s, Ketamine(1:18:57) Investing in funds(1:20:53) Ways LPs can add value for GPs(1:23:05) How status has changed in Silicon Valley(1:31:37) Backing founders with secrets, why failing is hardReferencedWeekend FundProduct HuntWayve self-driving carsThe community trapHooked: How to Build Habit Forming ProductsGet Your Wish - Porter RobinsonSocial UtilitiesSilicon Valley’s new status symbolsSelfish InvestingFollow RyanTwitterLinkedInPersonal WebsiteSignature BlockFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

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 rate in only four years, and they've done it in an industry that's become a Silicon Valley graveyard: SMB lending.Sahill talks about how they partnered with other marketplaces, vertical SaaS, and point of sale providers to offer financial services to SMBs at scale, landing DoorDash as their first customer before building the product, and advice for technical teams learning enterprise sales.Sahill's a fascinating founder, as he started his career getting a PhD discovering the Higgs boson particle at CERN’s Large Hadron Collider. We talk about physics, he explains how the Large Hadron Collider works, why physics is just real world machine learning, and all the lessons he learned on the growth teams at Facebook and Robinhood (including the way Robinhood acquired most of its userbase!)A thank you to Hans Tung at Notable Capital, Nick Shalek at Ribbit, and Mahdi Raza at Pathlight for their help brainstorming topics for the conversation.Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get your $250 here.Timestamps:(4:06) Lending to SMBs inside marketplaces and platforms(9:39) Why SMB lending is so hard(12:50) Three ways AI is changing Fintech(16:47) Silicon Valley’s graveyard of SMB lenders(22:44) Getting a PhD in Particle Physics(26:15) How CERN's Large Hadron Collider works(31:49) Discovering new dimensions(34:10) Building billion user data sets at Facebook(39:53) Working with other physicists at Robinhood(50:29) Growth lessons from FB + Robinhood(1:00:57) Starting Parafin, embedded, horizontal SMB lending(1:06:09) Why credit is the biggest problem for SMBs(1:10:53) Raising a Seed from Ribbit pre-product(1:13:25) Landing DoorDash as the first customer(1:16:51) Mastering B2B sales as a technical founder(1:22:58) Lessons from Vlad at RobinhoodReferencedParafin:Careers at ParafinEpisode with Charley & MahdiJuliusCERNLarge Hadron ColliderFollow SahillTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

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 AI data labeling business, how AI is changing the job market and careers, advice for scaling a three-sided marketplace, and Garrett’s approach to hiring executive-level talent.We also get into the early days of Handshake, tapping out his dad’s retirement account to fund the first years, driving across the US landing the first customers, sleeping in McDonald’s parking lots, sneaking into careers fairs, and inside Handshake’s first fundraise that took over seven months.Shoutout to Jeff Richards, James Alcorn, Ilir Sela, and Ben Christensen for helping brainstorm topics for Garrett.Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get your $250 here.Timestamps:(3:44) More Gen Z than LinkedIn(7:11) Helping frontier labs label AI data(14:43) Masters and PhD students flock to Handshake(16:52) Why Handshake will win in AI data labeling(19:24) Growing to $250m+ Revenue(21:56) KPIs in recruiting marketplace(24:45) How AI will change careers(33:57) How to build a Seal Team Six AI team(37:06) Interning at Los Alamos(40:00) Breaking into Silicon Valley from Michigan(44:19) Helping friends get jobs at Palantir(48:13) Driving across the US sleeping in McDonald’s parking lots(54:52) Funding early days with his dad’s retirement account(57:37) Handwriting letters to get the first six customers(1:03:06) Early product failures and iterations(1:11:01) Fundraising, crashing on couches for seven months(1:17:07) Finally closing a Seed round(1:20:05) Moving from Michigan to SF with no money(1:23:38) Importance of sequencing new features(1:29:10) Handshake’s exec recruiting process(1:32:01) Building a company with your best friendsReferencedTry HandshakeCareers at HandshakeGumloopPeter Thiel Startup SchoolPaul Graham’s blogFollow GarrettTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

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 things.We also unpack Railway’s bold product bets, like enabling creators to earn revenue with backend templates, building their own data centers, and not building their own AI models.Jake also talks about their four week new hire onboarding, how they build a problem roadmap, why operators should be managers, and why you should almost never work weekends.Thank you to Angelo Saraceno @ Railway and Erica Brescia Bacon @ Redpoint for help brainstorming topics for the conversation.Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get your $250 here.Timestamps:(3:33) Solving the hardest problems in dev tools(8:16) Starting with the hardest thing(11:18) How AI accelerated the need for Railway(12:50) Importance of backend in AI-native software(16:52) Jake’s angel fundraise strategy(20:51) Resisting AI for so long(25:32) Using AI to get leverage(29:57) Build vs buy in AI software(33:22) When Jake knew Railway was working(34:27) Creating infrastructure templates(38:04) Building data centers and a cloud service(40:27) Two moats: Hard problems and hard things(46:25) Hitting 8-figures in revenue(48:47) Railway’s four week onboarding(54:25) Building a problem roadmap(56:16) You can’t set your own culture(1:01:58) Railway’s viral “How We Work” post(1:08:39) Using Discord instead of Slack(1:11:25) How hypergrowth companies mess up org design(1:14:03) Why you shouldn’t work weekends(1:19:45) Not betting big on AI models(1:21:53) Lessons from Zuck, Martin ScorseseReferencedRailwayCareers at RailwayThe Inward Draw of CapitalismHow We Work Volume 1Volume 2Volume 3Volume 4Follow JakeTwitterLinkedInSubstackFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

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 philosophies that set them up for success 20 years later.We talk open source software, why Matt’s such a big proponent of it, how Automattic built its business model as one of the first SaaS companies (that now owns companies like Tumblr and WooCommerce), and how AI is changing engineering.Matt also shares how to build a community around your product, “Conscious Capitalism”, what he learned running one of the first distributed teams, and lessons on optimism from Walt Disney.Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp.Sign-up for Ramp and get $250 here.Timestamps:(3:48) WordPress: Powering 43% of the internet(8:30) Outcompeting Reid Hoffman’s startup in the early days(14:03) Why open source wins over the long-term(16:21) Business models in open source(21:12) Starting Automattic in 2005, one of the first SaaS companies(28:45) Spending most of Automattic’s Seed round on servers(33:36) How to use Community + Word of Mouth for early growth(38:38) Matt’s current situation with WP Engine(43:30) How to give back in open source(53:55) Best practices from 20 years of running a remote company(59:59) Lessons on optimism from Walt Disney(1:12:33) How AI is changing coding(1:16:09) Automattic's internal employee secondary market(1:23:51) How open source increases longevity (1:26:08) Matt’s favorite classical thinkersReferenced:AutomatticWordpressMatt’s BlogBay Lights in SFInnocence ProjectVesuvius ChallengePlastic ListThe Giving PledgeDAFFYPessimist ArchiveMatt's favorite quote from Rudy FranciscoMaintenance by Stuart BrandWe are as Gods by Stuart BrandMarginal Revolution by Tyler CohenFollow MattTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

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 AI to build the design around the story.Gamma has put up impressive metrics, growing from zero to $50 million in ARR and 50 million users with only 30 employees. They’ve also had zero employee attrition, and a negative lifetime burn rate, with more cash in the bank than they’ve raised.We talk about building a horizontal product instead of for a specific vertical, why Grant likes hiring generalist’s, how a quarter of the team is designers, why they’ve never raised large funding rounds, and how they run the company with an efficient team while not subscribing to 996 working hours.Grant also shares how Gamma rebuilt their entire product to be AI-native in the months after ChatGPT launched, and how every department at Gamma uses AI internally.Thanks to Anamitra and Gaurav at Afore, Shiyan @ Hustle Fund, Evan @ South Park Commons, and Vas @ Accel for helping brainstorm topics for Grant.Special thanks to presenting sponsor of The Peel, Ramp.Ramp: Time is money. Save both with Ramp. Join 40,000+ companies, go to https://ramp.com/ThePeelNumeral: The end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeelTimestamps:(3:46) Gamma: The anti-Powerpoint(5:56) How to be efficient with a small team(7:58) Importance of full-stack generalists(12:15) How to hire problem solvers(15:57) Changing slides from designs to narratives(20:13) Gamma’s freemium AI business model(22:36) Ignoring conventional wisdom with a horizontal product(28:47) Why Gamma started with Slides(32:21) Raising a Pre-Seed for a horizontal product(38:25) Why Gamma avoided hyped funding rounds(40:57) How fundraising impacts recruiting(43:40) Liquidation preferences and employee equity(47:08) Gamma’s zero employee attrition(49:54) Working in-person during COVID(52:15) Using waitlists to batch new user cohorts(56:08) Re-building the product to be AI-native(58:17) How to improve your onboarding(1:00:46) Benefitting from AI models getting better(1:05:10) Growing from 60k to 50 million users(1:07:30) How to stand out as an AI company(1:09:23) Creating a Gamma API(1:11:37) How Gamma uses AI internally(1:15:06) Why Gamma doesn’t do 996 working hours(1:19:54) 4-month product sprints(1:22:16) Parenting hacks: sleep, exercise, nutrition(1:24:26) Brand and community lessons from Nike and AppleReferencedGammaCareers at GammaOptimizelyNotebookLMFin / Intercom: Afore CapitalFollow GrantTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter here to get every episode + the transcript in your inbox every week.

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 issues that actually give the smallest companies the most leverage.We also talk about insurance more broadly, AI opportunities in insurance, lessons from kickstarting a marketplace doing nearly $3B in volume, when his wife got cancer two months after closing Threeflow's seed round, and how his co-founders adjusted to support him.Special thanks to Bolt for supporting this episode! Join the world’s largest hackathon - up to $1m in prizes. Sign-up here.Timestamps:(3:57) Threeflow: B2B benefits marketplace(5:50) How the benefits industry works(9:20) The importance of brokers in insurance(12:32) Benefits broker software stack(15:36) How to make money in employee benefits(21:11) Ways to compete in insurance(26:34) How AI is changing insurance(31:01) What its like to be an insurance broker(35:37) Starting ThreeFlow in 2016 pre-LLMs(40:13) The 128 day walk through Europe before Threeflow(44:47) When his wife was diagnosed with breast cancer(50:23) Advice for founders on surviving large personal events(52:46) Threeflow’s unorthodox Seed round(59:46) How to vet your investors(1:04:14) Why insurance brokers exist(1:05:08) How to build a marketplace on top of Vertical SaaS(1:10:53) Choosing a marketplace entry point(1:15:05) $2.5B in premium volume on Threeflow workflows(1:26:39) Importance of supply side volume in a marketplace(1:31:21) Fundraising without a formal process(1:33:03) Hiring for “just get stuff done”(1:36:22) AI opportunities in insurance(1:41:05) Building software in insurance(1:44:56) Tactics for running a distributed team(1:49:04) Creating your own playbooksReferencedTry ThreeflowCareers at ThreeflowFollow RyanLinkedIn: https://www.linkedin.com/in/ryansachtjen/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

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.We also unpack why 90% of venture funds simply can’t raise capital right now, advice for anyone raising a fund today, how to stand out as an emerging manager, why secondaries have become a primary driver of liquidity in venture, and how to navigate SPVs as a GP and LP.We also talk through the AI products they built to evaluate fund managers at Allocate, and how AI is changing venture and company building.A special thanks to Bolt and Warp for supporting this episode.Bolt: Join the world’s largest hackathon - up to $1m in prizes. Sign-up here.Warp: Automates payroll, handles multi-state tax compliance, and streamlines international contractor payments, so founders can focus on building, not busywork. Try it here.Timestamps:(5:31) Evolution of the private markets(17:55) VC markets post-2020(21:09) Risk / return profiles of various fund sizes(24:04) Secondaries will drive future venture returns(33:17) Creative ways to return capital(36:27) “Curiosity Revenue” in AI(41:52) Allocate’s Beyond Summit(43:42) Samir's AI fund analyzer(46:15) Fintech only 1% of financial services revenue(50:13) Triple-layered SPVs(54:50) Breaking down returns in venture(58:27) How to gauge a fund manager’s access(1:00:14) Determining appropriate fund size(1:05:02) 90% of venture funds cannot raise right now(1:09:50) How to raise a fund today(1:15:37) ChatGPT roasts Banana Capital(1:19:56) Traits of the best VCs(1:22:41) Vetting grit, hustle, and obsession(1:31:12) Why using AI is table stakes(1:36:49) Value of podcastsCheck out AllocateThe Peel episode with Eric Vishria Samir’s Venture Unlocked PodcastFollow SamirTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

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, what Afore looks for when backing founders before they even have a product, how to skip your Seed and go straight to a Series A, and how to run a fundraise process.We also get into Afore’s Founder in Residence program, why every VC started an accelerator, how AI is changing venture, joining Twitter as the first PM, and how Oprah helped create the legendary verified checkmark.Thanks to Gaurav Jain and Derrick Li at Afore for their help brainstorming topics for Anamitra.And special thanks to Bolt and Warp for supporting this episode.Bolt: Help them break a world record for the largest hackathon - up to $1m in prizes. Sign-up.Warp: Automates payroll, handles multi-state tax compliance, and streamlines international contractor payments, so founders can focus on building, not busywork. Try it here.Timestamps:(4:00) Afore: Starting in 2016 to build the pre-seed category(8:11) The unstructured data Afore underwrites at pre-seed(11:21) Pre-seed is determining bronze from gold(16:03) Why pre-seed is more than option checks(20:33) The secret to raising a Series A(23:20) Running a tight fundraise process(32:05) Skipping your Seed round(34:01) How to measure obsession in a founder(39:20) Knowing when to follow-on(40:54) Figuring out what really matters in a business(42:36) Afore’s Founder in Residence program(49:44) Pros / Cons of more access to capital for founders(52:27) Two reasons YC made every VC launch an accelerator(1:01:05) Why AI is forcing VCs to invest earlier(1:06:55) Will AI commoditize software?(1:08:29) Growing up in India, starting his first company(1:10:39) Coming to the US for school, joining Overture + Yahoo(1:14:05) Joining Twitter as first PM, creating the Verified check for Oprah(1:18:55) Building Twitter’s first ad product(1:20:28) Why non-founders can’t take foundational risks(1:23:02) Starting Afore for the Pre-Seed opportunity(1:27:47) Raising Afore Fund 1(1:31:14) How to raise your first fund(1:33:33) Was Turner the best Afore intern ever?ReferencedAfore CapitalK9 CapitalAfore’s Founder in Residence Program: SpeedrunPearXNeo AcceleratorGammaDevelop HealthFollow AnamitraTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

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 investments.We get into the risk rewards of Series As today, how Benchmark competes to work with founders, and and why the best storytellers win.We also talk about parallels between the 90’s, 2000’s, and today, and how the archetype of successful founders has changed in the age of AI.Thanks to Spenser Skates, Sajith Wickramasekara, Bobby DeSimone, and Semil Shah for help brainstorming topics for Eric!Special thanks to this episode’s sponsors:Bolt: Help them break a world record for the largest hackathon - up to $1m in prizes. Sign-up here. Numeral: The end-to-end platform for sales tax and compliance. Try it here.Timestamps:(5:17) What gets Eric excited about a new investment(7:48) Backing learning machines(12:34) Backing Cerebras at inception(16:20) Why the best storytellers win(21:17) How Eric works with founders(26:38) Companies going zero to $100m in 12 months(31:09) Revenue quality of AI products(32:41) Moats and business models in AI(38:41) AI margins and runway(41:14) Parallels between winners of the 90’s and today(44:54) Archetypes of the best AI founders(50:43) SaaS companies successfully pivoting to AI(53:43) LLMs are most comparable to transistors in the 1950s(56:19) Ways Eric uses AI personally(58:05) How VC has changed over the past decade(1:01:40) VC is a hustler’s business(1:03:20) Backing extraordinary companies is all that matters(1:09:36) What makes Benchmark unique(1:17:03) How Benchmark makes investment decisions(1:18:38) Skipping senior year of high school(1:20:21) Working with Ben Horowitz and Marc Andreessen ‘00-’08(1:24:42) Starting RockMelt, selling to Yahoo(1:26:28) Joining Benchmark in 2014(1:28:08) Investing in Confluent one month later(1:28:50) Lessons from Spenser at Amplitude(1:29:36) Fireworks AI’s hyper growth(1:30:49) Pricing in AI changing from tokens to outcomes(1:32:23) Ways Eric’s perception of VCs changed after becoming one(1:34:07) How to build a management team(1:38:21 )The best CEOs make new mistakes(1:39:50) Why there should be more public companies(1:44:03) “Even great companies can be overvalued”ReferencedBenchmarkCerebrasBenchlingBen Thompson + Mark Zuckerberg InterviewConfluentAmplitudeFireworks AIAndy Price at Artisinal TalentFollow EricX / TwitterLinkedInFollow TurnerX/ TwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week