Oren Zeev's $2.7B Solo GP Playbook

Emilie Choi is the President and COO of Coinbase, where she’s spent nearly a decade building the operating system Brian Armstrong runs the company on.She took a lateral move to join in 2018, the market crashed a few months later, and when the COO seat opened the board told Brian to go hire a big name. He promoted her instead.We get into why big company process makes you faster, the rule that makes starting a committee a fireable offense, why collaboration is a useless company value, the RAPID doc and the 48 hour clock, what happened when 15 outsider execs landed at once and tension erupted, why 1-on-1’s should be critical, what happened inside Coinbase during the rise and fall of FTX, and how Coinbase successfully sued the SEC.Thank you to Monaco, Flex, Clerk, and Numeral for supporting this episode.Monaco: The revenue engine for startups. https://monaco.comFlex: Premium banking, 60-day credit, 0% APR. https://home.flex.one/referral/bananacapitalClerk: Everything you need for authentication. https://clerk.comNumeral: Sales tax on autopilot. https://numeral.comTimestamps:(0:00) Process helps you move faster(5:14) Writing is thinking. Don't ship AI slop.(10:20) Agents are the next customer(13:50) Why starting a committee gets you fired(16:56) Tobi Lütke auto-deletes recurring meetings(19:48) How to roll back your recurring meetings(23:30) Collaboration is a useless company value(24:56) No politics at work(28:17) Shivers down her spine meeting Brian(31:43) What a great COO actually looks like(33:39) The weekly 1-on-1 where they criticize each other(36:14) Internal promos beat an outside COO(38:20) How to find candidates with grit(40:34) Talent density means managing people out(43:31) How to tell someone it isn't working(45:44) Coinbase: intelligence with humans around the edge(50:04) Regulators want AI 10x better than humans(52:46) TradFi embracing crypto made it boring(54:47) How Coinbase evolved beyond Bitcoin(58:32) Fred Wilson was the only Coinbase bull at YC Demo Day(1:00:36) Embracing capitalism when it's least popular(1:02:53) Gambling, prediction markets, and NFTs(1:06:29) Suing the SEC after FTX blew-up(1:09:30) Two choices: die quietly or go direct(1:13:06) Does going direct actually change outcomes?(1:17:28) Narrative whipsaws on Meta, Anthropic(1:18:52) How to operate throughout cycles(1:21:04) Off-sites are out, “Surges” are in(1:22:50) Why Coinbase stays remote-first(1:24:31) Jeff Weiner, the best operator she's seen(1:27:17) Sit at the fricking table(1:28:28) You don't have to talk in every meetingReferencedCoinbase: https://www.coinbase.com/Coinbase is a mission focused company: https://www.coinbase.com/blog/coinbase-is-a-mission-focused-companyRAPID decision framework: https://www.bain.com/insights/decision-insights-3-make-decisions-workFred Wilson’s Blog: https://avc.comWhat You Do Is Who You Are: https://www.amazon.com/What-You-Do-Who-Are/dp/0062871331Moneyball: https://www.amazon.com/Moneyball-Art-Winning-Unfair-Game/dp/0393324818Follow EmilieTwitter: https://x.com/emiliemcLinkedIn: https://www.linkedin.com/in/emiliechoiFollow 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/

Ivan Burazin is the Co-founder and CEO of Daytona, the cloud for AI agents.Daytona is fresh off hitting a $100M revenue run rate, up from $1M four quarters ago, and just announced a $60M round at a $1B valuation two weeks ago.We talk about why every company will get hacked by AI agents in the next 12 months, why the next bottleneck is CPUs and not GPUs, growing 51% per month after all their early customers died, the Series A that didn't happen, selling with no salespeople + 1,500 Slack Connect channels, and why your first act has to be a home run.Thank you to Monaco, Flex, Clerk, and Numeral for supporting this episode.Monaco: The revenue engine for startups https://monaco.comFlex: Sign-up for Flex Elite with code TURNER, get $1,000 https://home.flex.one/referral/bananacapitalClerk: Everything you need for authentication https://clerk.comNumeral: The end-to-end platform for sales tax and compliance https://numeral.comTimestamps:(0:00) Everyone will get hacked in the next 12 months(3:29) Agents find 10-year-old bugs daily(5:28) Daytona raises $60M at a $1B valuation(6:08) Every agent will need a computer(10:14) Agents use CPUs the way you use a calculator(13:16) Is a CPU shortage coming?(17:01) Why a new cloud provider can win today(19:55) Almost all of Daytona's first customers died(22:17) Growing 51% per month since launch(27:11) How to spot an opening in a crowded market(29:36) Competing on price commoditizes you(31:30) Why does everyone pay up for AWS?(33:26) Without attention and scale, product doesn't matter(38:12) Get attention from what you're best at(41:34) Drink-ups as early GTM(47:07) Why name it Daytona?(49:11) The original product: dev environments for humans(51:31) Agents need infra like Stripe, not AWS(54:00) When 50 customers ask for the same feature in days(57:35) No roadmap beyond six weeks(1:00:18) Growing 25x this year from tilts, not pivots(1:03:20) Every enterprise agent will need Windows(1:11:04) Croatian high school had no cliques or bullies(1:13:29) AI agent security is already solved(1:19:29) The Croatia price and perception discount(1:20:39) The Series A that didn't happen(1:23:11) Nobody believed agents need computers(1:25:43) Same pitch deck, new numbers(1:28:12) Moving the family to San Francisco(1:30:00) AI deployment has barely started(1:31:31) Daytona is in every lab's bring-your-own-sandbox(1:33:29) You don't learn much from failure(1:37:03) For an API company, the docs are the product(1:38:37) No salespeople, 1,500 Slack Connect channels(1:41:25) Write cold emails as short as a tweet(1:47:44) Get on the plane to SF(1:49:13) Borrow playbooks from musicians and athletes(1:52:16) Mario Kart and SoulcaliburReferencedDaytona: https://www.daytona.io/Careers at Daytona: https://www.daytona.io/careers$1M to $100M run rate in 4 quarters: https://www.daytona.io/dotfiles/1m-to-100m-run-rate-in-4-quartersFollow IvanTwitter: https://twitter.com/ivanburazinLinkedIn: https://www.linkedin.com/in/ivanburazin/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/

Aydin Senkut started Felicis 20 years ago with $4 million of his own money.After hearing "we don't back people like you" from every LP, he's now an early backer of iconic companies like Shopify, Canva, Adyen, Notion, and Supabase and investing out of a $900 million fund 10.We talk about why success is the downfall of a good investor, the 7 cold emails before he met Tobi, the endowment LP who grilled him like the CIA, why he hired a CFO at fund 3, if raising a 250x bigger fund causes you to lose your edge, Larry Page's 10x rule, and paying 700x revenue for Supabase.Thank you to Monaco, Flex, Clerk, and Numeral for supporting this episode.Monaco: The revenue engine for startups https://monaco.comFlex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapitalClerk: Everything you need for authentication https://clerk.comNumeral: Sales tax on autopilot https://numeral.comTimestamps:(0:00) Why success is the downfall of a good investor(2:04) Catching waves from YouTube to AI, chips, and defense(4:47) Is AI a bubble? How to tell what's real(6:17) Silicon Graphics: the company with no second act(7:33) Why AI infrastructure spend isn't hype(12:00) 7 emails, no reply: how he met Tobi at Shopify(15:30) On adding value: "Just ask the founder"(17:30) The founder pledge: vote with the founders(18:26) Fund 1 was $4M of his own money(21:01) Find LP's preconditioned to believe in you(22:07) Venture is a people business(23:05) Raising Fund 2: the endowment’s "CIA interview"(26:48) Why outsiders bet on outsiders(28:23) Turner's rejected podcast audition(30:46) LP pushback on Fund 2 and Fund 3(32:56) Why he hired a CFO at Fund 3(35:04) Feedback founders can't argue with(37:21) Founders forget the clock is ticking(40:43) Backing founders through the first bad quarter(42:34) Does a 250x bigger fund lose its edge?(45:53) a16z, OpenRouter, Cursor, and big fund returns(47:30) Why deep tech needs huge rounds(50:57) Trillion dollar markets, billion dollar contracts(53:36) Why SpaceX and Anduril alumni will crush it(56:34) From a $50k first exit to "off by three orders of magnitude"(58:17) The software mindset in hard tech(59:38) Google's duct-taped servers(1:00:56) Scanning every book in the world(1:02:37) Larry Page's 10x rule(1:04:54) Outsider founders: Shopify and Adyen(1:07:17) Why Silicon Valley VC's miss companies outside the Bay Area(1:08:16) Generalist vs. specialist: 55 unicorns, no subject experts(1:12:17) Category winners sit between sectors(1:14:59) Don't obsess over entry price(1:17:24) Paid 700x revenue for Supabase, it grew 1000x(1:18:33) Notion, Canva, and the one-button product(1:20:27) The "OpenAI is about to collapse" crowd(1:21:41) Inspiration from Benjamin Franklin(1:23:47) Funding the twinkle in a founder's eyeFollow Aydin:LinkedIn: https://www.linkedin.com/in/aydins/Twitter: https://x.com/asenkutFollow Turner:Twitter: 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/

Matt Murphy is a partner at Menlo Ventures and led Anthropic's Series D.Before Menlo, Matt sat in Google's board meetings at Kleiner Perkins from the first check to the IPO, and then backed Anthropic before it had a product or revenue.We talk about the similarities between early Google and Anthropic, bending all the rules to invest at a $4B pre-revenue valuation, raising a $500M+ SPV at an $18B valuation without being allowed to show LP's a single financial (and the 30 to 45 days he thought they might not pull it off), the three LP's who each made over $1B on the bet, the Anthology Fund check that became OpenRouter and four other unicorns, Menlo's barbell portfolio strategy, avoiding the messy middle of early growth rounds, and why most of the 70+ neolabs won't make it.Thank you to Monaco, Flex, Clerk, and Numeral for supporting this episode.Monaco: The revenue engine for startups https://monaco.comFlex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapitalClerk: Everything you need for authentication https://clerk.comNumeral: Sales tax on autopilot https://numeral.comTimestamps:(0:00) How to read Anthropic's S-1(1:21) Do AI companies actually make money?(2:23) Google didn't want ads. Anthropic didn't plan on enterprise.(4:51) Bending the rules to back Anthropic pre-revenue, pre-launch(9:50) You can't be a leading AI firm without a top model company(12:00) Leading the Series D at $18B six months later (14:22) Why the best researchers chose Dario(15:25) Menlo's first-ever SPV, nearly the size of the fund(16:44) The LP meeting that sparked a $500M SPV(19:18) Raising at $18B without showing financials(20:04) Three LP's made $1B+ each(24:23) Why Matt joined Menlo in 2015(26:00) Rebuilding Menlo over the past decade(32:49) Venture as a team sport(35:45) How to keep a challenger mentality(38:15) Why VC firms decay(41:31) The Anthology Fund: OpenRouter, Wispr, Goodfire(42:27) Ownership vs. backing the best(46:10) Why this isn't 1999(48:06) Frontier vs. open weight models(51:29) The barbell portfolio strategy(53:54) Avoiding the messy middle between early and growth(55:07) How to spot a category leader(57:18) Fortune 5000 AI adoption: "almost none"(59:06) Menlo is in 10 of 70+ neolabs: Skild, Chai, Axiom(1:02:13) Where $1B AI startup raises actually go(1:04:18) Phase 1 vs. Phase 2 of AI(1:06:26) What the AI IPOs mean for venture(1:09:11) What Matt does differently after 25 years(1:10:52) The Alex Smith lessonReferenced:Anthropic: https://www.anthropic.com/Menlo's Anthology Fund: https://menlovc.com/anthology-fund/Menlo's Modern AI Stack: https://menlovc.com/perspective/the-modern-ai-stack-design-principles-for-the-future-of-enterprise-ai-architectures/Follow MattTwitter: https://x.com/mmurphLinkedIn: https://www.linkedin.com/in/matt-murphy-0415543/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/

Oren Zeev runs one of the most successful venture firms in the world. The catch: he has no partners, no associates, holds no investment committee, writes no memos, and has no office.He's a solo GP managing $2.7 billion across 11 funds, an early backer of Audible, Houzz, Chegg, Tipalti, and Navan, where a relationship that started with a $50k check became a stake worth more than a billion dollars.We get into why most partners add negative value, the days his calendar is empty enough to surf on a Tuesday, why he's never shown an LP a single slide in 11 funds, why diversification is a lie, his fund that had only five companies, how Navan went from a $90M run rate to zero in a month (and survived), the cross-fund investing everyone tells him not to do, the DPI stand that cost him LP's, the Yozma Program that built Israel's startup economy, and the 30-minute meeting that turned into his first fund.Thank you to Monaco, Flex, Clerk, and Numeral for supporting this episode.Monaco: The revenue engine for startups https://monaco.comFlex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapitalClerk: Everything you need for authentication https://clerk.comNumeral: Sales tax on autopilot https://numeral.comTimestamps:(0:00) Running $2.7B with no team or partners(1:58) How one person can beat a team(4:43) Omission beats commission: why committees miss(7:13) What really fills a partnership's day(9:23) The returns business, not the production business(10:58) A week in his nearly empty calendar(16:49) The mistakes new solo GP's make(19:34) Eleven funds, zero slides(22:09) No thesis(24:28) Why diversification doesn't work(27:14) The fund with only five companies(30:44) TripActions insight: everyone hates their travel software(34:59) Paying employees to spend less(37:34) COVID: $90M run rate to zero(39:24) How Navan survived(41:34) A $100M round with no way to price it44:29) Keeping the team: the real test of leadership(46:04) What Oren looks for in founders(50:39) Cross-fund investing, and "trust me, bro"(53:59) Always his own biggest LP(55:14) The DPI stand that cost him LP's(58:54) Decart, and the Anthropic deal(1:03:54) Inside the 30-year rise of Israel's tech ecosystem(1:07:19) The Yozma program that built an industry(1:11:59) Why Israelis build now instead of selling early(1:14:39) Moving to the Valley in the 2002 nuclear winter(1:17:19) Audible, and why the first home run matters(1:19:29) Leaving Apax, and going solo(1:22:04) Peter Thiel and a fund raised in 30 minutes(1:24:24) The second fund: 48 hours, still no deck(1:25:49) ICON: helping Israeli founders crack the Valley(1:30:29) The leader he admires most: Anwar SadatReferenced:Zeev Ventures: https://www.zeevventures.com/Navan: https://navan.com/Mercury Interactive: https://en.wikipedia.org/wiki/Mercury_InteractiveICON: https://www.iconsv.org/Yozma: https://en.wikipedia.org/wiki/YozmaFollow OrenTwitter: https://x.com/orenzeevLinkedIn: https://www.linkedin.com/in/ozeevFollow 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/

Darragh Buckley was the first employee at Stripe. He’s since started Increase, the banking infrastructure that moves over $500 billion a year. And he just bought a bank.We talk about how to buy a bank, why putting an API on a bank is like "strapping a jet engine to a go-kart", operating with high-empowerment, the overnight sprint that turned on Stripe’s first dollar of revenue, why Patrick and John Collison would run across the office, and why you want your banker to be bored.Thanks to this episode’s sponsors:Monaco: The revenue engine for startups. https://monaco.comFlex: Premium banking, 60-day credit at 0% APR. https://home.flex.one/referral/bananacapitalClerk: Everything you need for authentication. https://clerk.comNumeral: Sales tax on autopilot. https://numeral.comTimestamps:(0:00) Stripe's 1st employee bought a bank(1:38) Fixing the stone in his shoe building Stripe(7:59) Banking looks like 2010 payments(11:11) Merging two layers into one, just like Stripe(14:52) Why he finally bought the bank(16:26) How do you actually buy a bank?(20:20) The first bank that got away(22:04) Why banks can’t chase new fads(25:26) Compliance as code, from day one(29:46) Talking straight to the Federal Reserve(32:19) The Fed migration that nobody noticed(33:50) The missing last mile of banking(35:44) Getting customers to switch(38:23) The challenger sales model(40:33) What customers use Increase for(41:48) How Ramp's bill pay works(42:37) $500B a year with 33 people(45:31) Hiring for a high-empowerment culture(47:08) Growing up with the Collisons(50:27) 150 test cases in one night(54:23) What really made early Stripe work(57:07) Why Patrick and John sprinted everywhere(1:00:00) “You're not in payments, you're in fraud”(1:02:31) Where AI hits a wall on fraud(1:05:08) Giving payment cards to AI agents(1:09:27) Use boring technology widely(1:11:37) You want your banker to be boredReferenced:Increase: https://increase.comCareers at Increase: https://increase.com/articles/how-we-workStripe: https://stripe.comLinks:NBA Player Harrison Barnes Buying a Bank: https://sports.yahoo.com/articles/nba-player-harrison-barnes-invests-155500816.htmlAcquire or Be Acquired Conference: https://www.bankdirector.com/event/acquire-or-be-acquired-2026/Choose Boring Technology Essay: https://mcfunley.com/choose-boring-technologyPrevious episode with Ron Gabrisko @ Databricks: https://www.youtube.com/watch?v=WYOO0DfeXu4Previous episode with Will Gaybrick @ Stripe: https://www.youtube.com/watch?v=AM1_NADNSgIPatrick Collison's "Fast": https://patrickcollison.com/fastAuthorize.net: https://www.authorize.netFollow DarraghX: https://x.com/darraghbuckleyLinkedIn: https://www.linkedin.com/in/darragh-increase/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/

Bilal Zuberi spent 18 years investing hard tech, most of it as a GP at Lux ($7B AUM), before starting @RedGlassVC in 2025 to bet on AI that touches the physical world.Bilal was making defense tech investments 15 years ago, and he led the Series A in Applied Intuition, now a $15 billion company.We hung out for a few hours and he shared everything he's learned investing in hardware, why hardware is still hard, why the deployment layer is the most attractive area of physical AI, taking a 90% pay cut to start Red Glass, "AUM as a moat", how to become a billionaire off management fees, and why consensus investing is mostly a circle jerk.Thanks to this episode's sponsors:Monaco: The revenue engine for startups https://monaco.comFlex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapitalClerk: Everything you need for authentication https://clerk.comNumeral: Sales tax on autopilot https://numeral.comTimestamps:(0:00) Leaving $7B to bet on physical AI(0:51) What most people get wrong in physical AI(4:17) Why a startup has to become a business(11:31) Hardware is still hard, so what changed?(15:40) How government went from SBIR mills to real customer(17:48) Robotics goes from hard-coded to probabilistic(23:34) Where value accrues: full stack, then wedges(25:24) How Applied Intuition became a $15B company(28:03) The deployment layer is the real prize(32:22) OpenAI and Anthropic hint what will happen in physical AI(36:14) Why customers have all the downside(37:56) The best founders paint a picture and execute(40:53) Why it's called Red Glass (founders chew glass)(42:17) Every founder hates fundraising, even Travis(44:29) Red Glass's four core values(50:49) Why founders really take your call (the $250k effect)(53:28) What Bilal looks for in a founder(58:44) Why technical founders underrate fundraising(1:00:26) The Tiger Global era(1:04:02) From $10B to $100B, the goalposts moved(1:06:21) Is this a bubble? Portfolio construction(1:08:55) Building a firm that outlasts him(1:12:13) From Nobel-lab chemist to Zero-to-One investor(1:13:45) Are small funds just outsourced associates?(1:16:35) When AUM becomes the moat(1:18:34) How big funds choke off SPV money(1:21:24) The risk of VCs backing competitors(1:23:31) Why fund economics push everyone bigger(1:26:20) Consensus investing is a circle jerk(1:29:51) You can be a billionaire on fees alone(1:33:09) Equal carry and the right to win(1:35:55) Why good ethics in VC matterCheck out Red Glass VC: https://www.redglass.vc/Follow BilalTwitter: https://x.com/bznotesLinkedIn: https://www.linkedin.com/in/bzuberiFollow 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/

Jamie Siminoff built the first WiFi video doorbell in his garage, got rejected on Shark Tank, and nearly went bankrupt "at least four times" while growing Ring into one of the largest consumer hardware businesses in the world.We talk about the $1.15B sale to Amazon, coming back to lead Ring after leaving post-exit, and what he learned having a fresh set of eyes on the business.We also get into the near death stories, like Christmas the company almost died from $1M of bricked doorbells, the $175k "F you, wire it" fight for the Ring.com domain, betting millions on TV ads when the board said no, landing Shaq as an early investor and celebrity endorser, the real backstage story of three dead demo units on Shark Tank, and why Jamie thinks AI can zero out crime in neighborhoods.Thanks to this episode's sponsors:Monaco: The revenue engine for startups https://monaco.comFlex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapitalNumeral: Sales tax on autopilot https://numeral.comAmplitude: AI analytics https://amplitude.comTimestamps:(0:00) Leaving Amazon, coming back with fresh eyes(7:49) Deleting every useless meeting(10:21) Zero-based time budgeting(15:31) Bubble, or the golden age of AI?(19:50) $480M to several billion in revenue(23:48) Lessons on obsession from MrBeast(30:17) The AI vision for Ring(34:05) The $10k feature he can't ship yet(38:50) Building apps on top of Ring(40:03) Building in his garage, the Kickstarter ban(44:45) The pre-sale, and the fear of getting copied(47:59) How he talked his way onto Shark Tank(49:24) Three dead units backstage(54:04) Threatening Shopify's CEO before air(55:23) The Christmas Ring almost died(58:59) The midnight fix that saved the company(1:01:22) Raising from True Ventures, the "ass hat" email(1:05:04) Hiring gritty “new to business” people(1:07:15) Missionaries, not mercenaries(1:10:13) Building an authentic brand people trust(1:12:49) Buying Ring.com with the last $175k of cash(1:18:11) “We were always on the verge of bankruptcy”(1:19:12) Betting $1M on TV ads when the board said no(1:22:43) Why TV ads actually work(1:25:26) Richard Branson, and doubling mid-raise(1:28:46) Closing Shaq, how to do authentic celebrity endorsements(1:33:27) Selling to Amazon for $1.15 billion(1:35:16) Being paranoid to lose people's money(1:36:38) Mentors, and never meeting your heroesReferenced:Ring: https://ring.comDyson: https://www.dyson.comTrue Ventures: https://www.trueventures.comOm Malik: https://om.coAdam D'Augelli: https://www.linkedin.com/in/adamdaugelli/Saar Gur: https://www.linkedin.com/in/saargur/Eoghan McCabe: https://www.linkedin.com/in/eoghanmccabe/Sky Dayton: https://www.skydayton.com/Tobi Lütke: https://www.linkedin.com/in/tobiaslutke/Follow JamieTwitter: https://x.com/JamieSiminoffLinkedIn: https://www.linkedin.com/in/jamiesiminoff/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/

Tomer London is the Co-founder and Chief Product Officer of Gusto.We go deep on how Gusto builds product, from obsessing over customers to shipping Gusto Cofounder with AI in eight weeks. We also get into what AI is doing to small businesses, surviving COVID, the manual world of payroll before software, what his dad's 40-year clothing store taught him, starting Gusto out of YC, and how Gusto thinks about making acquisitions now that it’s crossed $1B ARR.Thanks to this episode's sponsors:Numeral: Sales tax on autopilot https://numeral.comFlex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapitalAmplitude: AI analytics https://amplitude.comMonaco: The revenue engine for startups https://monaco.comTimestamps:(0:00) Obsessing over small businesses(10:09) Building Gusto Cofounder in 8 weeks(13:57) What AI is actually doing to small businesses(19:52) COVID and "the end of small business"(27:42) Why running a small business is so hard(32:21) SVB and why payroll can't be late(36:29) How GTM changes after 500,000 customers(39:27) Running payroll manually before Gusto(46:19) Why payroll and compliance are so hard(49:14) What his dad's clothing store taught him(54:00) Are we regulating small business out of existence?(58:04) Starting as ZenPayroll in 2012(1:05:02) Getting the first customers(1:07:28) Minimum Lovable Product vs MVP(1:11:28) How AI changed the way Gusto builds(1:15:58) Gusto's M&A playbook(1:22:52) Shimon Peres and "no room for small dreams"ReferencedGusto: https://gusto.comGuideline: https://www.guideline.comY Combinator: https://www.ycombinator.comSam Blond on The Peel: https://www.thespl.it/p/the-ai-native-gtm-playbook-sam-blondNo Room for Small Dreams, by Shimon Peres: https://www.amazon.com/No-Room-Small-Dreams-Imagination/dp/1538412209Follow TomerTwitter: https://x.com/tomerlondonLinkedIn: https://www.linkedin.com/in/tomerlondonFollow 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/

Jeff Morris Jr is the founder and Managing Partner of Chapter One. Previously, he was employee 50 at Tinder and started Chapter One from his desk before quitting to go full-time on investing.We talk about running a venture firm more like a product team, running 50 experiments every fund cycle, why Sequoia doing $60 million Seeds has killed round labels, why the best firms only pick right 4-7% percent of the time, running the world's smallest accelerator, branding a venture firm, when to pivot, the time he delivered Valentine's flowers himself in Kansas, why none of his Fund 1 winners were in the Bay Area, and why he never announced his $64m Fund 3.Thank you to Numeral, Flex, Amplitude, and Monaco for supporting this episode.Numeral: Sales tax on autopilot https://numeral.comFlex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapitalAmplitude: AI analytics https://amplitude.comMonaco: The revenue engine for startups https://monaco.comTimestamps:(0:00) Publishing IC notes every week(3:48) Do round names matter anymore?(8:20) Putting a big check into Erebor's $2B round(11:40) Why deep tech went from instant pass to preferred in 3 years(15:32) When deep tech companies should raise debt(19:03) Should this company raise $1M or $100M?(23:25) You have two days to say yes(25:58) Sourcing software he built at Tinder(28:05) Their crypto book hit 22x, then the market turned(30:58) Paradigm, SendCutSend, and re-founding a firm(33:35) If you're going to pivot, re-found the company(37:21) Flex's wedge was too illegible to fund(40:13) When should you actually pivot?(42:47) Zaarly, the Uber for everything(45:17) Moving to Kansas City with a bag of clothes(47:25) Delivering flowers door-to-door(51:31) Raising a $64M Fund 3 and not announcing it(56:33) Joining Tinder as employee 50(57:35) The push notification that took down Tinder(1:00:59) Why you shouldn’t start a dating app(1:04:18) Consumer got too predictable(1:09:00) Why consumer AI economics look worse than enterprise(1:13:02) Launching Chapter One from his Tinder desk(1:15:08) 50 experiments per fund cycle(1:16:11) Product Club, the world's smallest accelerator(1:19:05) Evolving portfolio construction between funds(1:21:25) Why picking rates have fallen(1:24:41) Smaller funds can invest in illegible categories(1:27:27) Zero Fund 1 returners were in the Bay Area(1:29:16) Don't compete with Sequoia at Seed(1:32:01) His grandfather built Mervyn'sReferencedChapter One: https://chapterone.comErebor: https://erebor.bankFlex: https://flex.oneSendCutSend: https://sendcutsend.comParadigm: https://www.paradigm.xyzSupabase: https://supabase.comPoke: https://poke.comFloodgate: https://www.floodgate.comSV Angel: https://svangel.comUnion Square Ventures: https://www.usv.comZaarly: https://www.crunchbase.com/organization/zaarlyMervyn's: https://en.wikipedia.org/wiki/Mervyn'sMervin Morris obituary: https://www.almanacnews.com/news/2021/09/10/mervin-morris-founder-of-mervyns-stores-atherton-resident-dies-at-101/People MentionedJamesin Seidel: https://www.linkedin.com/in/jamesin-seidel-5325b147/Palmer Luckey: https://x.com/PalmerLuckeyMike Maples Jr: https://www.linkedin.com/in/maples/Scott Belsky: https://www.linkedin.com/in/scottbelsky/Josh Elman: https://www.linkedin.com/in/joshe/David Lee: https://www.linkedin.com/in/davidlee10/Max Mullen: https://www.linkedin.com/in/maxmullen/Follow JeffTwitter: https://x.com/jmjLinkedIn: https://www.linkedin.com/in/jeffmorrisjrFollow 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/