The Peel with Turner Novak

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 why most VCs aren’t helpful with recruiting at the zero to one stage, his thesis on starting an early stage venture firm to help founders hire A+ teams, a crash course on early stage recruiting and building a sales team, and how COVID hit right after he left Lightspeed to raise Audacious Fund 1. Timestamps:(00:00) Intro(03:43) Evolution of VC platform teams(09:53) How Audacious runs in-house recruiting processes(15:16) The reason large firms can’t help with Seed stage recruiting(17:06) Immigrating from India to the US mid-financial crisis(21:59) Silicon Valley's secret weapon(25:59) The opportunity to start a recruiting-focused Seed firm(30:14) Raising Audacious $90m Fund 1 in April of 2020(36:58) The new guard of Seed firms(39:23) Why $50-75m is the minimum viable institutional fund size(41:48) How to work with the best founders(45:30) Navigating deal dynamics, term sheets, and valuations(52:24) The two hardest parts about starting your own fund(54:32) Lessons applied raising Audacious $125m Fund 2 in 2023(58:46) Evolving from a PMF-first to Founder-first investor(01:02:09) Five traits of force of nature founders(01:07:05) How to build an A+ team(01:11:46) The importance of backchanneling(01:13:54) Why everyone thinks they’re a good people reader(01:14:35) Two most common mistakes in recruiting(01:20:59) Determining urgency of a customer’s problem(01:22:55) Hiring and scaling your first sales team(01:25:55) Why marketing is the hardest role to hire for(01:31:59) What good sales people look like(01:35:43) How to move up market + how to do pilots(01:43:40) Why Nakul admires Rafael Nadal Referenced:Audacious: ⁠https://www.audacious.co/ ⁠ Nakul’s immigration journey: ⁠https://www.nakulmandan.com/blog/2024/an-immigrant-living-the-american-dream⁠ Force of nature founders: ⁠https://www.nakulmandan.com/blog/2024/traits-i-look-for-in-founders⁠ Early GTM hiring: ⁠https://www.nakulmandan.com/blog/2023/initial-gtm-hiring-for-saas-startups⁠ Follow Nakul:Twitter: ⁠https://x.com/nakul⁠ LinkedIn: ⁠https://www.linkedin.com/in/nakulmandan⁠ Follow Turner:Twitter: ⁠https://twitter.com/TurnerNovak⁠ LinkedIn: ⁠https://www.linkedin.com/in/turnernovak/Subscribe to my newsletter to get every episode + the transcript in your inbox every week: ⁠https://www.thespl.it⁠

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 kids, Roll Rider. For full show notes, visit: https://highlightai.com/share/9bc59c07-05ab-41aa-b37e-f35a7c92092d  Timestamps:(00:00) Intro(05:31) How social media was Rent the Runway’s first tailwind(07:21) Being early to sustainable fashion(09:21) Starting the company at HBS in 2008(12:36) Launching with no fashion or tech background(14:49) The three biggest early surprises(18:44) Using “show don’t tell” to fundraise(20:06) Why customer social proof was so important(23:04) Spending only 10% of revenue on marketing(25:12) Getting the NYT to cover their launch(29:43) Early mistakes(31:29) Re-building the product a few weeks before launch(33:11) Why building their own logistics was so important(38:59) Subscriptions, retail, and other key product decisions(45:15) How the internet makes it harder to shop(49:30) Building conversational commerce at Walmart(53:48) Lessons from starting a company with her kids(58:38) Favorite startups in AI and commerceReferenced:Rent the Runway: https://www.renttherunway.com/ NYT’s Launch Coverage: https://www.nytimes.com/2009/11/09/technology/09runway.htmlCheck out Roll Rider: https://rollrider.com/ Use code TURNER15 for 15% offFollow Jenny:Twitter: https://x.com/Jenny_RTR LinkedIn: https://www.linkedin.com/in/jennifer-fleiss-18577314Follow Turner:Twitter: https://x.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/ 

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 cold outbound.We also get into why founder-led content is so important today, and why design is a crucial core competency. For full show notes, visit: https://highlightai.com/share/28b95226-9936-4ae9-882d-6c68a1b578d5  Timestamps:(00:00) Intro(02:10) OpenPhone’s new API launch(06:41) Why a better business phone is a big deal(13:18) Immigrating from Ukraine to the US and building OpenPhone(15:39) Hacking a custom business phone(25:29) How OpenPhone got its first customers from Facebook Groups(33:02) Tricks for unlocking word of mouth(39:11) Transitioning from free to paid users(43:05) How OpenPhone cracked word of mouth on Reddit(46:29) OpenPhone’s YC experience(49:01) Why the Seed round was hard to raise(53:49) Using Slack to aggregate all customer feedback across the internet(57:38) How YC helped redefine their ICP(01:01:33) Tactics for sending cold emails(01:06:24) How to get and benefit from press(01:12:18) Daryna’s “behind the scenes” approach to founder-led content(01:16:26) Using long-tail keywords to kickstart an SEO strategy in 2020(01:23:05) When to do founder-led content vs SEO(01:28:38) How your customers should pull you up-market(01:30:18) Why OpenPhone cares about design Referenced: OpenPhone: https://openphone.com/ Ahrefs: https://ahrefs.com/ Follow Daryna: Twitter: https://twitter.com/darynakulya LinkedIn: https://www.linkedin.com/in/darynakulya Follow Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

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 about investing. For full show notes, visit: https://highlightai.com/share/883f2cc9-9771-4331-9a42-6ae236f50344 Timestamps: (00:00) Intro (03:18) Growing up middle class while dad worked at NASA (12:31) Moving to Baltimore to work for Bill Miller (18:12) What Lisa learned from Bill (19:41) How value investing changed over the last 30 years (26:40) Investing in internet stocks in the 90’s and 00’s (29:50) Thinking a 13x win on AOL in 1996 would be the biggest of her career (37:33) Teaching Barry Diller about the internet (41:30) How Dell reinvented PC manufacturing and created a negative cash conversion cycle (46:46) How Amazon survived the Dot Com Crash (51:53) Buying 24% of Amazon in 2002 (53:15) Why companies get the investors they deserve (57:22) What Lisa learned from Jeff Bezos (1:04:31) Lessons from raising too much money (1:07:57) Running her own fund from 2006-2016 (1:13:32) Why fees in asset management are too high (1:15:20) Joining Facet out of retirement 2017 (1:20:20) What she learned about investing from operating (1:23:47) Why women are better investors than men (1:26:43) How to hire outlier candidates (1:35:06) Why no one can be the next Warren Buffett (1:39:54) When to sell your winners Follow Lisa:LinkedIn: https://www.linkedin.com/in/lisa-rapuano/ Follow Turner:Twitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

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, how to define your ICP, why you should always size markets bottoms-up, having a fast response time, how seed investing has changed since 2007, and Gokul’s hot takes on titles at a startup. 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. Timestamps:(00:00) Intro(02:14) Common thread of success between the founders of Google, DoorDash, Facebook, and Square(05:50) Gokul’s first job in Silicon Valley(07:46) How Serendipity led to PMing Adsense, one of Google’s biggest products(12:20) Lesson from Sergey Brin on reducing friction before a products magic moment(18:50) How Zuck used founder mode to beat Google Plus in 2011(22:51) When big acquisitions can go well(24:47) How Gokul switches from startup helper to public company board member(28:09) The evolution of Seed investing since 2007(33:27) How to have a fast response time(37:40) Lessons from Jack Dorsey always selling(39:54) How to define your ICP(42:40) Using bottoms-up to size a market(44:05) Why Director and VP titles are bad for startups Referenced:Who’s Got the Monkey? https://hbr.org/1999/11/management-time-whos-got-the-monkey   Getting Things Done: The Art of Stress-Free Productivity https://www.amazon.com/Getting-Things-Done-Stress-Free-Productivity/dp/0142000280   How to Size a Market in 30 Minutes https://blog.blingcap.com/2023/02/13/How-to-Size-a-Market/ Follow Gokul:Twitter: https://x.com/gokulr  LinkedIn: https://www.linkedin.com/in/gokulrajaram1 Follow Turner:Twitter: https://twitter.com/TurnerNovak  LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/  

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 early days of Blaze and Snyk. He shares lessons on marketing to developers, hiring when no one wanted to work for him, overcoming multiple difficult funding rounds, and lessons from multiple M&A processes.Timestamps:(00:00) Intro(02:21) The four quadrants of building and investing in AI(14:59) Why AI startups are riskier than non-AI startups(19:42) When to sell your company vs keep building(24:57) Why hiring the early team is so hard(26:32) Early marketing tricks from Guy’s first company, Blaze(29:09) Strategies for using conferences to grow your brand(33:33) Getting three days of free PR(38:04) Moving to Ottawa(42:11) Why Sales Engineer is an underrated founder stepping stone(45:49) What he learned as CTO of Akamai(48:31) Starting his third company Tessel, and why there’s no satisfaction without struggle(50:41) How Snyk got started(54:10) Creating developer-first security(59:59) Secrets for developer marketing(01:02:31) Why podcasts work so well for marketing(01:06:26) Snyk’s failed Series AReferencedTessl: https://tessl.io/Snyk: https://snyk.io/Charting Your AI Native Journey: https://www.tessl.io/blog/charting-your-ai-native-journeySecure Developer Podcast: https://snyk.io/podcasts/the-secure-developer/AI Native Dev Podcast: https://www.tessl.io/podcastWe didn’t mention it in the podcast, but Guy just announced the AI Native Dev Conference, a virtual conference on Thurs, November 21st. Join him + many others here https://ai-native-devcon.heysummit.com/Follow GuyTwitter: https://x.com/guypodLinkedIn: https://uk.linkedin.com/in/guypoFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakNewsletter: https://www.thespl.it/

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 at a Series A startup in nine months. This episode is packed with advice on sales, getting your first startup role, and everything he’s up to at Hanover. Timestamps(00:00) Intro(02:11) Why B2B SaaS is dead(07:20) Competing against companies that have “IT departments”(11:37) Going from 0 to 100k on Twitter in one year(19:06) The ASS networking framework(25:17) Interviewing at 50 startups before quitting Goldman to join Meow(28:41) Lessons going from sales IC to Chief Revenue Officer in nine months(32:47) Using SSS to send good cold emails(35:51) Learnings as a first-time manager(40:46) How to make a good first impression(47:22) Why sales and copywriting are underrated(49:17) Navigating the startup idea maze to fund admin(56:47) 1-click fund admin migration, 1-minute time to value(59:46) Turning down Hanover’s first term sheet with no backup plan(01:03:28) Using polite persistence to get customers(01:08:41) Why the best companies are cults(01:11:01) John D Rockefeller and vertical integration(01:13:26) Doing culture fit questions at the beginning of the hiring process(01:15:34) Chris’ favorite AI tools(01:17:58) How to make founder-led content ReferencedCheck out Hanover: https://www.hanover.co/Brick: https://getbrick.app/Alex Hormozi’s Sales Podcast: https://open.spotify.com/show/6YNopzKDGDwf0auIpPTIIDSweetgreen: https://www.sweetgreen.com/Chipotle: https://www.chipotle.com/Eight Sleep: https://www.eightsleep.com/Turner’s episode with Jonathan Neman at Sweetgreen: https://open.spotify.com/episode/1Emm6VOq6MCEfQlXv05q6U?si=hJMc8LhBTeeonYJGza4gxQThe Hanover Manifesto: https://www.hanover.co/manifestoClaude Sonet: https://claude.ai/Cursor: https://www.cursor.com/Hemingway Editor: https://www.hemingwayapp.comFollow ChrisTwitter: https://twitter.com/chrishladLinkedIn: https://www.linkedin.com/in/chris-hladczuk-b09204153Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakNewsletter: https://www.thespl.it/

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) Growing up in basements(05:15) Charley’s journey to first biz hire at Plaid(15:01) Advice on being a good startup employee(19:34) Mahdi’s path to Robinhood(26:33) Deciding between joining an early or late stage startup(32:39) Why Charley joined Plaid despite VCs telling him not to(38:52) Benefits of case studies in hiring(39:58) Why every hyper growth company is a shit show(44:24) Startup comp: equity, QSBS, early exercise, vesting(49:59) Joining Ramp as the first Head of Growth(58:35) How Ramp got its first customers(01:02:06) Advice and common traps on early GTM strategies(01:05:04) Why $1M ARR does not mean you have PMF(01:06:51) Meeting when Robinhood bought, churned, then returned to Plaid(01:09:54) Deciding to build Pathlight together(01:23:06) Raising Fund 1 in 2021 and how bad timing almost killed it(01:29:55) Reasons founders work with Pathlight(01:32:04) Why most investors add no value and give bad advice(01:36:44) Founders Pathlight invests in + Artie case study(01:44:44) Competing with incumbent funds(01:53:57) Raising a $75m Fund 2 in 2023(02:02:22) Are Seed extensions good investments?(02:07:45) Discussing startup valuations(02:09:09) Mahdi’s 10-minute market outlook (as of 8/8/24) Referencedhttps://www.pathlight.vc/https://plaid.com/https://robinhood.com/us/en/https://ramp.com/https://stytch.com/https://www.alloy.com/https://www.artie.com/ Follow CharleyTwitter: https://twitter.com/charleymaLinkedIn: https://www.linkedin.com/in/charleyma Follow MahdiTwitter: https://twitter.com/mahdirazamrLinkedIn: https://www.linkedin.com/in/mahdirazany Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakNewsletter: https://www.thespl.it/  

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 FBI at his house when he was a kid, and lessons driving the monorail at Disney. We also get into the founding story of ClickUp, bootstrapping to $10m in ARR, hiring mistakes from scaling too fast, why Zeb likes hiring users, how ClickUp shipped generative AI features so fast, its new chat product launched earlier this week, and the trend of software convergence. Timestamps:(00:00) Intro(02:11) Zeb’s first near death experience(08:19) Childhood businesses that had the FBI at his house(18:23) Lessons from driving the monorail at Disney(25:19) Mistakes scaling from 100 to 800 employees in one year(31:04) Dropping out of college after being robbed at gunpoint(33:19) How building a CraigsList competitor led to ClickUp(35:32) Three waves of ClickUp’s product evolution(39:25) How the product slowly got worse over time(44:45) Hiring the guy who built Microsoft Teams to rebuild ClickUp(48:11) Zeb’s favorite interview question(49:59) Daily 5am standups in the first year(54:28) How ClickUp got its first customers(57:16) Bootstrapping to $10m in ARR with strong retention(58:13) Zeb’s best kept secret, user surveys (and how to run them)(1:02:42) The trend of software convergence(1:08:26) Reasons Zeb likes hiring users(1:12:19) Why VCs didn’t invest, and why it led to a better business(1:19:02) Raising from Craft, Georgian, and a16z(1:21:08) Peter Thiel: “I think you’re right”(1:24:35) How ClickUp was early to AI(1:28:03) Launching chat and video calls to hit ClickUp's original vision(1:32:02) What Zeb’s excited and cautious about in AI(1:37:24) Why Zeb journals every day Referenced:ClickUp: https://www.clickup.com ClickUp’s new chat feature: https://clickup.com/features/chat Follow ZebTwitter: https://x.com/dj_curfew LinkedIn: https://www.linkedin.com/in/zebevansclickup Follow TurnerTwitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Newsletter: https://www.thespl.it/ 

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 security. Pomerium has a unique open source approach, and Bobby takes us inside the early days of building the product, how he got the first customers, lessons learning enterprise sales as a technical founder, and inside his funding rounds, including a recent Series A led by Eric Vishria at Benchmark.  Timestamps(00:00) Intro(02:02) Access Control: a sneaky large problem(07:22) How an unsecure air conditioner led to the biggest credit card breach in history(10:23) Google’s internal security software inspiring Pomerium(16:41) Making his first money online selling a WoW bot(19:24) How CrowdStrike took down the global economy in July, 2024(22:29) Deep dive on access control and security(29:39) How access controls impacted Google vs Uber’s self-driving lawsuit(30:52) Why Zero Trust security is marketing bullshit(32:09) Advice for building access control(34:39) How open source built early trust with customers(41:39) Missing a 7-figure deal because he didn’t use LinkedIn(44:52) Everything he’s learned about sales as a technical founder(50:06) Inside Pomerium’s Series A(51:41) Advice on evaluating potential investors(56:06) How AI will change security(01:01:15) Getting in trouble at the first Pomerium board meeting(01:02:15) How to hire good engineers(01:04:00) When to scale back IC work as a founder(01:06:56) Favorite new AI tools(01:11:09) Why Meta’s open sourcing its AI models(01:12:32) Life lessons from Charlie MungerReferencedCheck out Pomerium: https://www.pomerium.com/ Crowdstrike outage post-mortem: https://www.crowdstrike.com/falcon-content-update-remediation-and-guidance-hub/ Pomerium on GitHub: https://github.com/pomerium/pomeriumFollow BobbyTwitter: https://x.com/bdd_io LinkedIn: https://www.linkedin.com/in/bobby-desimone/Follow TurnerTwitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Newsletter: https://www.thespl.it/ 

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 inside the playbook that grew to $1.5m in monthly revenue in less than three years, including how they first positioned the product in a crowded market, how beehiiv ships so fast, when a co-founder passing away less than one year into building the business, and the day GoDaddy took the entire beehiiv platform offline for 8 hours. Timestamps(00:00) Intro(01:36) Why Turner didn’t invest in beehiiv (twice)(03:04) Joining MorningBrew as the first employee(15:28) Why newsletters are so powerful(19:40) Scaling MorningBrew to 3.5 million subscribers and exiting to Business Insider(23:14) Difference between startups and big companies(26:26) Why beehiiv has two days of no meetings(27:53) The initial insight to start beehiiv(35:39) Building a programmatic newsletter ad marketplace(39:52) Dissecting beehiiv’s nearly $20m rev run rate business model(45:21) Inside beehiiv’s first funding round(46:58) Where Turner’s reference check went wrong(50:45) Litquidity and beehiiv’s initial product positioning(52:59) How beehiiv builds in public(57:41) Banning meetings two days per week(01:00:13) Why the best remote teams always beat in-person(01:06:19) The impact of a co-founder dying one year into the business(01:11:50) Raising a Series A despite operating at breakeven(01:16:14) Why Tyler writes public investor updates(01:21:04) Moving fast, and “why perfect kills all momentum”(01:26:03) When GoDaddy took beehiiv down for 8 hours(01:29:57) Why Tyler writes a newsletter(01:32:21) His Big Desk Energy Spotify playlist(01:36:08) Why you never regret firing bad hires(01:39:53) Looking up to Elon and Brian Chesky(01:41:34) Monk mode in Columbia ReferencedThe Power of Investor Updates: https://mail.bigdeskenergy.com/p/power-investor-updatesbeehiiv’s old investor updates: https://mail.bigdeskenergy.com/c/beehiiv-investor-journeyThe BDE Spotify Playlist: https://open.spotify.com/playlist/5s8443tfYUq3LLARJwGeYP Where to find TylerTwitter: https://twitter.com/denk_tweetsLinkedIn: https://www.linkedin.com/in/tyler-denkNewsletter: https://mail.bigdeskenergy.com Where to find TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakNewsletter: https://www.thespl.it

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 software consolidation (03:00) Why billings and payments isn’t consolidating (06:09) Early tricks for avoiding future tax headaches (08:42) Founder lessons from first being a VC (09:28) The two catalysts that led to Anrok (17:15) How software companies used to figure out sales tax (22:51) Raising Anrok’s Seed round in 48 hours (25:42) How to join a VC's scout program (28:24) Fundraising lessons from being an investor (34:24) Surprising results from the very first “easy file” product (38:30) Lessons getting the first customers from outbound (40:19) Why you should make your first two sales hires at the same time (41:50) Sales advice when scaling into enterprise customers (46:19) How your Seed round helps raise your A and B (47:24) The reason AI and LLMs are so hard to predict (50:58) Michelle’s favorite Claude use cases (53:51) Predicting market sizes, and why Figma’s seemed small (57:39) How to invest in AI right now (1:01:01) Advice on changing your opinion (1:04:10) Getting outside your comfort zone (1:05:04) Michelle’s go-to interview question (1:34:50) The most ridiculous SPACs (1:07:23) Lessons from Scott Cook, the founder of Intuit Referenced Check out Anrok: https://bit.ly/3YTb0ED Anrok’s Journal Entries Newsletter: https://bit.ly/3AxrtUV Anrok Mid-year SaaS Sales Tax Review: https://www.anrok.com/resources/mid-year-saas-sales-tax-review-2024 Michelle’s Article on AI, Part 1: https://www.linkedin.com/pulse/fog-ai-what-investors-missing-part-one-michelle-valentine Part 2: https://www.linkedin.com/pulse/fog-ai-what-investors-missing-part-two-michelle-valentine Part 3: https://www.linkedin.com/pulse/fog-ai-what-investors-missing-part-three-michelle-valentine Superintelligence: https://www.amazon.com/Superintelligence-Dangers-Strategies-Nick-Bostrom/dp/1501227742 Where to find Michelle: Twitter: https://twitter.com/_vltn LinkedIn: ⁠https://www.linkedin.com/in/michellevalentinehk/ Where to find Turner: Twitter: ⁠https://twitter.com/TurnerNovak⁠ LinkedIn: ⁠https://www.linkedin.com/in/turnernovak/⁠ Newsletter: ⁠https://www.thespl.it/

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 is now the largest Jiu Jitsu apparel brand in the US, which he almost went bankrupt running during the financial crisis. He shares how that business led to ShipHero, takes us inside the early days, explains why warehouse robotics and 4PL’s are overhyped, and discuss the rapid rise of TikTok Shop, Temu, and Shein. Timestamps (00:00) Intro (02:01) The USPS shipping label scam (07:10) Starting the largest Jiu-Jitsu apparel brand (09:46) Narrowly avoiding bankruptcy in 2008 (17:08) Why ecommerce is so hard (21:16) Starting ShipHero to manage their own warehouse (28:00) Powering Shopify’s early fulfillment network (30:59) How 3PL’s are still solving basic problems (34:02) Why warehouse robotics is overhyped (41:48) Where drones fit into logistics (44:55) Aaron argues why the 4PL model doesn’t work (55:40) TikTok Shop is the fastest growing US ecommerce channel ever (58:42) How Temu and Shein leverage the 321 program to avoid tariffs (1:02:49) Why Temu and Shein are slowing US ecom growth (1:04:17) Topgrading: The most boring, most valuable hiring strategy (1:11:29) Business lessons from playing poker Referenced ShipHero: https://shiphero.com/ Topgrading: https://www.amazon.com/Topgrading-Hire-Coach-Keep-Players/dp/094400234X Where to find Aaron Twitter: https://x.com/AaronandML LinkedIn: https://www.linkedin.com/in/aaronandml Where to find Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Newsletter: https://www.thespl.it

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 cycles and bubbles, and what Logan’s seeing in the data today, especially in AI, plus Logan’s philosophy’s on venture capital as an asset class, his favorite under the radar investors, and advice for his younger self. Timestamps: (00:00) Intro (01:33) Not getting invited to Michael Rubin’s white party (04:29) Meeting on Twitter during COVID (11:09) How Logan and I benefited from Twitter (16:55) Early days of the Logan Bartlett Show (22:10) Why podcasts are so hard to grow, and how Logan did it (24:50) Learning YouTube’s the best for podcast growth (29:51) Inside Logan’s web3 episodes with Zach Weinberg (32:07) Lessons from studying history and market cycles (33:15) Producer Ben fact checking Logan's historical railroad statistics (39:42) How to invest in and around bubbles (51:00) Market data from Redpoint’s 2024 AGM update (55:12) Differences between companies valued at 100x and 5x ARR (1:00:04) The Barbell Theory of asset management and why Logan disagrees it will happen in VC (1:09:40) Ways VCs can actually add value (1:12:27) Redpoint’s founding story + greatest hits (1:18:14) The most underrated investors and founders (1:21:35) Advice for young people: pick a niche, go deep, stay focused If you enjoy this conversation and you’re not already, make sure to like, comment, follow, and subscribe to my newsletter in the show notes to get future episodes in your inbox every week. Referenced: Clearspace https://www.getclearspace.com/ Acquired’s TikTok episode https://www.acquired.fm/episodes/tiktok Gorilla Game https://www.amazon.com/Gorilla-Game-Picking-Winners-Technology/dp/0887309577 Redpoint’s AGM Update https://docs.google.com/presentation/d/1T3kGf-n4cmd6_UqOQNb79ZXFL723b9HdZyTnk9sLOlM/edit Where to find Logan: Twitter: ⁠⁠⁠https://x.com/loganbartlett LinkedIn: ⁠https://www.linkedin.com/in/loganbartlett/ Where to find Turner: Twitter: ⁠⁠⁠https://twitter.com/TurnerNovak⁠⁠⁠ LinkedIn: ⁠⁠⁠https://www.linkedin.com/in/turnernovak/ Newsletter: ⁠⁠⁠https://www.thespl.it/⁠

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 extreme sports websites (11:07) Why a better pipeline solves all problems (13:24) Ryan’s trick for hiring executives (17:00) Selling the ad network to USA Today (18:11) Moving to SF to start a software company (21:33) Getting rid of his car to extend runway (24:23) Paying rent with credit cards (29:17) Struggling to raise a Series A (31:55) Using channel sales to grow the business (37:05) Almost running out of money before selling to Groupon (43:37) How cloud created the perfect timing to build Electric (48:33) Leveraging software and AI to automate manual human tasks (51:45) Why you should avoid buzzwords in marketing (53:57) Pros and cons of being a solo founder (56:14) Why Electric built a large initial board (01:02:41) Advice for picking lead investors (01:06:35) How VC fund dynamics have inflated Seed rounds (01:09:16) The downsides of high valuations (01:12:45) Almost wiring back the Seed round (01:16:37) Why every fundraise is a Pipeline problem (01:21:04) The reasons VCs actually pass on founders (01:26:42) Cutting the burn rate in 2022 Electric.ai: ⁠https://www.electric.ai/⁠ Where to find Ryan: Twitter: ⁠⁠⁠https://twitter.com/DenehyXXL⁠ LinkedIn: ⁠⁠⁠https://www.linkedin.com/in/ryandenehy/ Where to find Turner: Twitter: ⁠⁠https://twitter.com/TurnerNovak⁠⁠ LinkedIn: ⁠⁠https://www.linkedin.com/in/turnernovak/⁠⁠ Newsletter: ⁠⁠https://www.thespl.it/

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://joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll. Frank Rotman is the Co-Founder and CIO of QED Investors, and before that helped start Capital One. Frank and I go deep on their founding stories, as well as one of QEDs first big winners, Nubank. Frank also gives us a crash course on fintech, lending businesses, and crypto use cases; his hot takes on the venture asset class as a whole, with lots of advice for emerging managers; plus a case study on how high valuations too early on are bad for a startup. Timestamps: (00:00) Intro (04:22) Starting Capital One in 1988 (07:04) Spinning out as an IPO (10:42) Starting QED in 2008 before Fintech was a category (20:51) Raising their first outside fund (22:03) Investing early in Nubank (25:11) Fintech opportunities in India (27:45) De-risk investing in new markets (29:55) How financial services have changed over the past 30 years (31:33) Inside a new Capital One credit card in the 90’s (36:31) How most companies launched new cards in the 90’s (39:46) The most profitable types of credit card customers (42:00) Mistakes founders make building credit businesses (48:33) Frank’s “Three Body Framework” for VC (54:48) Losing strategies in VC (01:03:39) Unpacking why high valuations are bad for startups (01:16:20) Frank’s journey in and out of crypto (01:24:23) Actual use cases for stable coins and NFTs (01:34:09) Unpacking the lending supply chain (01:41:44) The difference between Fundamentalist and Revolutionary investors Referenced: VCs Three Body Framework: https://cdn.prod.website-files.com/605db59b78445cf5ae548e49/628b9d826f9af3217c9807a2_Three-Body%20Problem_%20Finding%20the%20New%20Stable%20Points%20in%20Venture%20Capital.pdf The House Money Effect: https://x.com/fintechjunkie/status/1466217991532650496 Fundamentalist vs Revolutionary Investors: https://www.linkedin.com/posts/frank-rotman_there-has-been-and-always-will-be-two-competing-activity-7128137991654445057-NuXf/ Where to find Frank: Twitter: https://twitter.com/fintechjunkie LinkedIn: https://www.linkedin.com/in/frank-rotman/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

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/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. Yossi Levi shares his incredible story: transforming a small family car lot into a $28 million dollar powerhouse, founding venture-backed Gettacar and growing it to $90 million in revenue, before returning the capital to investors and growing his anonymous Twitter account into Car Dealership Guy, a B2B automotive media empire. Yossi takes us inside his early marketing strategies, the hard earned lessons from chasing product-market fit, and the playbook to building a lean, scalable B2B media machine. Timestamps: (00:00) Intro (07:26) Helping at his dad’s used car lot (11:22) How car dealerships make money (14:32) $28m revenue with Facebook ads  (17:48) Putting gifts in customer trunks and filming it (22:58) Starting Gettacar to sell cars online (25:04) When a VC pulled his first term sheet (31:08) Recruiting full-time hires with part-time consulting gigs (34:45) Personally guaranteeing the debt used to finance vehicles (36:50) Helping subprime consumers buy cars online (39:24) How 2021 tricked them into thinking they had a sustainable business (41:57) Why you can’t rush Product Market Fit (42:23) Pivoting Gettacar to a profitable, PE-backed business before winding it down (47:22) Starting an anonymous Twitter to share insights from his day-to-day (50:08) Turning Car Dealership Guy into a media business  (53:38) Doxing himself with a 13-minute documentary  (58:29) Why you have to consume to be a good creator (1:00:04) Screensharing CDGs content schedule (1:02:59) Why every employee needs to generate content or revenue (1:09:27) Creating a car / auto influencer agency (1:11:34) Building a B2B automotive ad network (1:14:50) Evolving into a holding company (1:20:27) Importance of moving fast  (1:23:34) Why people actually like sponsored content (1:28:08) Wishing he pivoted to B2B faster More on Car Dealership Guy: ⁠https://www.dealershipguy.com/ Referenced Who the F*ck is Car Dealership Guy: ⁠https://www.youtube.com/watch?v=_wTsAez_nMs⁠ Russ Flips Whips: ⁠https://russ.dealershipguy.com/⁠ Freight Waves’ Craig Fuller on The Peel: ⁠⁠https://youtu.be/oPPqO8eBq2M⁠ Epic Gardening’s Kevin Espiritu on The Peel: ⁠https://youtu.be/FefGL-qPzDo⁠  Where to find Yossi: Twitter: ⁠https://twitter.com/GuyDealership⁠ YouTube: ⁠https://www.youtube.com/@CarDealershipGuy⁠ Where to find Turner: Twitter: ⁠https://twitter.com/TurnerNovak⁠ LinkedIn: ⁠https://www.linkedin.com/in/turnernovak/⁠ Newsletter: ⁠https://www.thespl.it/

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/ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. Edwin Dorsey is the author of The Bear Cave, a weekly newsletter exposing publicly traded companies that are misleading investors and harming customers. I’ve enjoyed Edwin’s writing since he launched his newsletter the Bear Cave in 2020, and he shares his best kept secret for doing customer research: FOIA requests. We also get into short selling more broadly, common corporate red flags, the economics of his media business, almost getting kicked out of Stanford for raising issues at Care.com his sophomore year, Planet Fitness’s illegal billing operation, Hershey’s Mr. Beast problem, and the creator economy more broadly. (00:00) Intro (05:11) How shorting works (07:20) How short sellers exposed Enron (10:51) Edwin’s process for finding bad companies (15:52) Root Insurance and aggressive pricing (20:14) FOIA: the best kept secret for company research (24:30) Biggest corporate red flags (28:17) Most common industries for bad actors (29:32) Why scammers target minorities and low income consumers (31:46) Edwin’s $1B to $10B market cap sweet spot (34:03) The challenges of mainstream media (38:15) Exposing Care.com as a student at Stanford (45:25) Why immediate board resignations are a red flag (49:45) Launching The Bear Cave in Feb 2020 (49:37) Using podcast appearances to grow (56:06) The newsletter's business model (1:00:00) Experimenting with side-newsletters, job boards, and consumer surveys (1:10:04) Planet Fitness: gym or illegal billing operation? (1:18:45) Herbalife the pyramid scheme (1:21:05) Hershey’s MrBeast problem (1:28:15) Marketing and social signaling in CPG products (1:30:47) AgEagle Aerial Systems: $4B market cap, zero revenue (1:34:50) The most ridiculous SPACs (1:41:06) How Edwin differentiates his research (1:47:07) Favorite short sellers (1:47:59) Companies that will lose to AI (01:49:29) Why creator-led business will steal share from incumbents Referenced The Bear Cave: https://thebearcave.substack.com/ FOIA Request Template (#13 here): https://www.readideabrunch.com/p/our-2023-hedge-fund-analyst-christmas SEC Full Text Search: https://www.sec.gov/edgar/search/ WSJ’s Care.com Story: https://www.wsj.com/articles/care-com-puts-onus-on-families-to-check-caregivers-backgroundswith-sometimes-tragic-outcomes-11552088138 Planet Fitness CEO resignation letter: https://x.com/StockJabber/status/1762220603715596460 Aurelius Value: https://x.com/AureliusValue Big River Capital: https://x.com/BigRiverCapita1 Marc Cahodes: https://x.com/AlderLaneEggs David Orr: https://x.com/orrdavid Citron Research: https://x.com/CitronResearch Where to find Edwin: Twitter: https://twitter.com/StockJabber LinkedIn: https://www.linkedin.com/in/edwin-dorsey-a9195273/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

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/ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. Lisa Wehden is the Founder and CEO of Plymouth Street, making fast and simple immigration for technologists. We go deep on the broken US immigration system, how its holding back US innovation, and the secret 0-1A Visa you can get in as fast as four weeks. Lisa lived in a sawmill while building her first climate tech startup, and we go inside that journey, giving the VC money she raised back to start Plymouth, raising grants to fund it, and how she broke into Silicon Valley as an outsider. Timestamps: (00:00) Intro (04:51) The state of US immigration (09:26) Why immigrants are good founders (11:43) The secret O-1A Visa (12:18) Why the O-1A is easier to get (16:54) Founders that have gotten their O-1A (20:00) Getting a Visa in four weeks with Plymouth (22:01) The 500-page, physical paper Visa application (25:57) Lisa’s US immigration COVID hobby (27:58) Living in a Sawmill building a climate tech startup (30:59) Giving VCs their money back (32:19) Joining Interact in SF (33:51) Raising grant money instead of VC (34:40) Becoming a paralegal to learn the industry (37:24) The Plymouth 100 community (39:20) How Lisa raised grant funding from Eric Schmidt and Tyler Cowen (43:55) Talent is the bottleneck to AI development (46:04) How to break into Silicon Valley as an outsider (52:43) Hiring on hopes and fears (55:31) "Write it down, make it happen" (56:45) Benefits of doing a calendar audit (1:01:54) Anyone can be an entrepreneur (1:04:53) Why Lisa doesn’t work from her phone (1:06:38) How to fix the US immigration system More on Plymouth Street: https://www.plymouthstreet.com/ Referenced: Interact: https://joininteract.com Lisa’s 0-1 Visa Guide: https://lisa-wehden.medium.com/a-guide-to-applying-for-the-o-1-visa-for-extraordinary-individuals-8ca5f22ff86b Writing a forwardable email intro: https://also.roybahat.com/introductions-and-the-forward-intro-email-14e2827716a1 Where to find Lisa: Twitter: https://twitter.com/lisawehden LinkedIn: https://www.linkedin.com/in/lisa-wehden-aa111385/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel 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. Melissa Cash is the Co-founder and CEO of Pok Pok, a montessori-inspired collection of digital toys that spark creativity and learning through open-ended play. Prior to Pok Pok, Melissa spent a decade working in marketing and design roles, helping Snowman drive 9-digits of downloads across its game portfolio and designing physical products at Disney. Timestamps: (00:00) Intro (05:46) Creating a Montessori inspired game (12:18) Why it's impossible to avoid screen time (15:35) Designing a non-addictive product (17:38) Monetizing a non-addictive game (21:47) How to price a subscription game (24:18) Using new features to drive retention (26:04) Marketing a kids game to parents (30:59) Why Pok Pok waited to launch Android (34:12) How getting pickpocketed in Germany led to a job designing products at Disney (39:23) How great products can define a childhood (43:21) Lessons from having a great idea while working at Disney (46:03) First coming up with the idea for Pok Pok (49:00) Advice for starting your first company (50:10) Fundraising tactics from Pre-Seed to Series A (54:08) How to build your network from zero (57:08) Getting the most out of Slack groups (59:07) Melissa’s hack for in-person events (01:01:33) Tactics for meeting people at events (01:03:39) Winning multiple Apple design awards (01:07:07) How to get press for your startup (01:13:17) Prioritizing getting women on Pok Pok’s cap table (01:18:38) Strategies for staying creative (01:21:58) Melissa’s influencer marketing hacks (01:24:24) Lessons from failed influencer campaigns (01:28:19) Growing 5x YoY, adding STEM content (01:30:28) What surprised her about starting a company Referenced: Try Pok Pok for 50% off an annual subscription with code POKPOK50: https://apple.co/3XAGSwT Snowman Studios: https://www.builtbysnowman.com/ Hampton Private Founder Group: https://joinhampton.com/ VC Backed Mom’s: https://www.vcbackedmoms.com/ The Peel Podcast episode with Eric Newcomer: https://www.youtube.com/watch?v=HXH_peQWtnc More on Pok Pok’s Series A: https://techcrunch.com/2024/06/18/now-a-series-a-startup-kids-app-and-digital-toy-pok-pok-is-coming-to-android/