Charley Ma and Mahdi Raza are the Co-founders of Pathlight Ventures, and were early employees at five unicorns, Plaid, Ramp, Alloy, Robinhood, and Styth. 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 in 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(01:58:32) 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/
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Ed Sim is the Founder of boldstart ventures, which partners with bold founders reinventing the enterprise stack at the inception stage. Ed takes us inside the journey building boldstart, from its first $1m fund in 2010 up to $850m in AUM today. Timestamps: (00:00) Intro (03:48) Evolution of early stage investing(05:11) Inception stage investing (10:32) Backing bold founders reinventing the enterprise stack(11:20) Repeatable ways to build enterprise businesses (12:04) The 5 P’s of early stage investing (14:12) Backing Guy Podjarny and Snyk (18:18) Knowing when to follow-on (19:18) The 3 Ch's of a good board member (22:01) How Ed’s board role changes over time (24:20) Balancing founder friendly with returns (27:20) How to build customer relationships (30:24) Advice for closing customers (33:47) Creating the Seed category in 2009/10 (37:31) boldstart’s $1m Fund 1 (39:00) Why Ed didn’t join a large firm in 2012 (39:55) boldstart’s $16.5m Fund 2 (40:26) Why LPs passed on the first funds (43:11) Leading rounds in Kustomer, Snyk, BigID, and Blockdaemon in Fund 3 (47:09) Why $112m Fund 4 was the hardest to raise(50:52) Ed’s approach to LP fundraising (55:12) Inside Meta’s acquisition of Kustomer and sale back to the founders (59:52) Backing Rahul from Superhuman a 2nd time (01:00:52) The different GTM playbooks (01:02:20) Importance of contract size and time to close (01:05:07) Why AI makes security more important (01:06:11) When to switch from founder-led sales(01:07:46) Backing ProtectAI after a conference (01:08:28) Balancing between inbound and outbound sales (01:09:55) Winners and losers in AI (01:15:26) Building the boldstart team (01:25:19) Lessons being an interim CEO (01:27:15) How ZIRP pulled revenue forward (01:29:08) The death of high growth software (01:32:58) Identifying startup opportunities incumbents won’t crush (01:35:00) Second order effects of AI (01:36:46) Using "Intuitive TAM" to size new markets (01:38:04) Investing before there’s a market map (01:38:57) Balancing family, fitness, and career Referenced: https://boldstart.vc/ Turning Down HBS: https://x.com/edsim/status/1315644287007240193 Ed’s tweet on raising Fund 4: https://x.com/edsim/status/1315644287007240193 Second Order Effects of AI: https://www.whatshotit.vc/p/whats-in-enterprise-itvc-379 Death of Hyper Growth: https://x.com/edsim/status/1797613384994623808 Where to find Ed: Twitter: https://twitter.com/edsim LinkedIn: https://www.linkedin.com/in/edsim/ Newsletter: https://www.whatshotit.vc/ 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 Nilam Ganenthiran is the founder and CEO of Beacon Software. Previously, he was the 12th employee and President at Instacart. We talk tactics for customer research, building customer relationships, balancing strategy and execution, how to serve on and manage a board, what happened when Amazon bought Instacart’s biggest customer Whole Foods, inside its COVID response, surviving eight months of runway in 2015, his new company Beacon Software, and more. Timestamps: (00:00) Intro (04:23) Inside Amazon acquiring Instacart’s biggest customer, Whole Foods (12:13) Lessons from quickly signing 8 of the top 10 grocers (13:06) Why grocers were slow to adopt ecommerce (15:29) Building “Shopify for grocers” (16:22) Sales = building relationships (19:05) Why Wegman’s is one of the best grocers in the world (20:43) Cold calling Wegman’s and signing them two years later (24:33) How to do customer research (26:59) Catching an Uber in suits on the highway (28:50) Why Instacart was possible back in 2013 (30:36) Launching Instacart’s advertising network (38:46) Growing 5x in 5 weeks during COVID (45:20) How Nilam started angel investing (47:56) Advice for sitting on boards (50:00) The roles and incentives of a board member (54:03) Deciding when to keep going and when to give up (56:02) Nilam’s framework around optionality (59:17) Seven years of weekly redeye flights (1:00:30) Almost running out of money 8 months after Instacart’s Series C (1:07:54) Why time is your scarcest resource & startups are default dead (1:10:00) Nilam’s new company, Beacon Software (1:11:28) Why he’s excited about AI (1:13:25) How AI makes human relationships more important (1:14:41) Turner’s investing lessons from family members Beacon Software: https://beaconsoftware.ca/ Where to find Nilam: Twitter: https://twitter.com/nilamg LinkedIn: https://www.linkedin.com/in/nilamganenthiran/ 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 Ankur Goyal is the Founder and CEO of Braintrust, the end to end developer platform for building the world's best AI products. Their customers include companies like Instacart, Zapier, Notion, Airtable, Replit, and more. We hit on the importance of LLM evals, advice for building AI products, why the best companies have two AI product roadmaps, and his non-conventional advice for founders. Timestamps: (00:00) Intro (04:04) Why everyone’s now an AI company (06:03) Reasons LLM evals are so important (08:10) Typescript becoming the language of AI (09:19) Replacing vibe checks with Braintrust (10:37) Making OpenAI’s protocols the standard (11:27) Why the best companies have two AI roadmaps (13:06) Building your product so each LLM release makes it better (14:54) Predicting AGI is impossible (15:54) Why people who work with LLMs aren’t worried about AI safety (16:52) The best developers are all-in on co-pilots (18:11) How AI is changing software development (21:09) Combining IDE, CIDC, and observability in one product (27:18) Are models more like CPU’s or relational databases? (30:14) How to pick an LLM (33:00) Advice for staying on top of new AI developments (34:30) Why tool calling is so important (38:02) Advice for young software engineers (40:25) Learning to code doing linear algebra homework (42:36) Lack of purpose interning in big tech (44:07) Working at MemSQL learning to be a founder (47:52) How to get a job at a startup (50:43) Building his first startups product on an international flight (52:39) Three lessons from his first failed startup (54:46) Don’t delegate what you’re good at (55:46) Why you should be careful listening to VCs advice (57:34) Tactics for successful delegation (59:36) Why Ankur doesn’t do any meetings (01:02:42) The importance of self-service in unlocking certain customer segments (01:05:14) How Braintrust got started (01:07:45) Advice on picking your target customers (01:10:35) How Braintrust hires with work trials (01:15:21) Balancing security with a modern UI (01:17:49) Why it’s hard to sell non-AI products right now (01:19:21) Advice for selling to large enterprises (01:23:10) Ankur’s favorite AI products Referenced: https://www.braintrustdata.com/ SICP Book PDF: https://web.mit.edu/6.001/6.037/sicp.pdf Hardcopy: https://www.amazon.com/Structure-Interpretation-Computer-Programs-Engineering/dp/0262510871 Linear’s guide to work trials: https://linear.app/blog/why-and-how-we-do-work-trials-at-linear Where to find Ankur: Twitter: https://twitter.com/ankrgyl LinkedIn: https://www.linkedin.com/in/ankrgyl/ 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/AttioThePeelAlan Feld is the Founder and Managing Partner of Vintage Investment Partners. Vintage is one of the largest fund of funds in the world, managing over $4 billion across what is mostly investments into other venture funds, plus some secondary and direct startup investments at the growth stage. Timestamps: 00:00 Intro 03:53 What is Vintage 05:40 Why VCs adding value can waste a founder’s time 09:01 VC, where the asset chooses the investor 10:14 Fund size is the enemy of returns in VC 14:57 What people get wrong about FoFs 16:01 The value FoFs bring to LPs 17:11 Why entrepreneurs drive VC returns 17:55 Vintage’s unique FoF model 19:05 Does replacing the founders with an outside CEO work? 21:39 Starting Vintage after the Dot Com Crash in 2002 23:41 Buying secondaries at 70-80% discounts 25:13 Biggest mistakes when buying secondaries 26:18 Research around what makes the best entrepreneurs 31:09 Lessons from six downturns 34:41 Comparisons between 2002 and 2022 37:07 Advice for raising your first VC fund 41:16 The importance of differentiation 45:57 Sustainable ways to differentiate 49:05 What Vintage looks for in new fund investments 49:57 Advice for scaling a VC firm 53:47 Succession planning 57:50 What Alan’s doing post-Vintage Vintage Investment Partners: https://www.vintage-ip.com/ Where to find Alan: Twitter: https://twitter.com/alanf_feld LinkedIn: https://www.linkedin.com/in/alan-feld-1744389/ 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 Anu Sharma is the Co-founder and CEO of Millie, building a better care system from the inside out. Our conversation covers the existing maternal health system, how Millie is reinventing it, and how to succeed building a healthcare company. Timestamps: (00:00) Intro (03:16) Problems in US maternity care (13:21) Why insurance reimbursement drives healthcare (16:11) How bundled care unlocks personalization (18:48) From fiction writer to 20 years in healthcare (24:22) Why consumers don’t act like consumers in healthcare (26:09) The reason scale matters (27:43) Bundled payments and new care design (32:16) What make Millie unique (35:58) Importance of picking regional markets in healthcare (37:08) The two paths for insurance reimbursement (41:08) Why distribution is the product in healthcare (44:25) Opportunities in cash pay care (48:28) How Anu fundraised without a product (51:06) The future of in-person, hybrid, and virtual healthcare (52:56) Building maternity clinics for $150k Check out Millie: https://www.millieclinic.com/ Where to find Anu: Twitter: https://twitter.com/anu_anusharma1 LinkedIn: https://www.linkedin.com/in/anu-sharma-b169b12 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 Aaron Levie is a co-founder and the CEO of Box. This conversation covers opportunities in AI, the early days of Box, and lessons Aaron's learned on his founder journey. Timestamps (00:00) Intro (03:11) Why ChatGPT was an iPhone moment (04:37) Advice for large companies incorporating AI (11:16) Why AI will add jobs, not steal them (16:13) How AI is supercharging Box’s products (19:03) AI agents: the $1 trillion opportunity (25:27)Estimating size of new markets(29:58) Starting Box with high school friends (33:18) Living out of their first office (34:52) Why early investors passed on Box (37:24) Pivoting from consumer to B2B (39:53) How Box got its first customers (41:57) Should founders talk to Associates at VC firms? (43:26) How Mamoon at Kleiner saved Box at its Series B (46:25) Turning down an acquisition before IPO (50:51) Why Box’s IPO was so hard (54:11) Fending off an activist investor during COVID Check out Box: https://www.box.com/ Where to find Aaron: Twitter: https://twitter.com/levie LinkedIn: https://www.linkedin.com/in/boxaaron/ 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 Attio, the next generation of CRM: https://bit.ly/AttioThePeel Elad Gil is the founder of Color Genomics and Mixer Labs, which he sold to Twitter, and an early investor in iconic companies like Airbnb and Stripe, plus upstarts like Perplexity and Anduril. This is a wide ranging conversation that covers education, AI, and advice for building a startup. Timestamps (00:00) Intro (03:46) Building cool monuments (09:12) Fixing education (16:38) Why AI is underhyped (19:02) Four trends to watch in AI (19:55) Why there aren’t large biotech companies (23:21) The current state of Elad Gill (24:32) How he incubates companies (26:32) Contemplating AI-driven buyouts (27:29) His investing strategy, from early to late stage (36:57) Why he remained solo for so long (40:19) How to get conviction in unpopular investments (42:53) What made Steve Jobs a good communicator (44:00) The importance of ambition and leadership (46:28) Why Elad puts so much weight in the market (47:45) The evolution of Google’s business model (49:17) How to monetize consumer products (50:06) Analyzing a potential startup market (51:23) How successful products eventually become distribution companies (56:30) Non-obvious startup advice (59:54) When its OK to give up (01:02:20) Advice on raising your first round (01:03:21) Picking board members (01:04:45) How to hire your first three employees (01:06:48) Avoiding bad hires (01:08:39) The importance of speed of execution (01:12:36) Why he’s adding to his team (01:14:31) Gardening Referenced: Elad’s Blog: https://blog.eladgil.com/ Elad’s Podcast: https://www.youtube.com/@NoPriorsPodcast/ Elad’s Book: https://growth.eladgil.com/ Where to find Elad: Twitter: https://twitter.com/eladgil LinkedIn: https://www.linkedin.com/in/eladgil Elad’s Website: https://eladgil.com/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/