The Peel

Samir Kaji is the Co-founder and CEO of Allocate.This conversation is a deep dive into the private markets, the evolution of venture capital as an asset class, and how there are now 10x more private investment firms than public companies.We also unpack why 90% of venture funds simply can't raise capital right now, advice for anyone raising a fund today, how to stand out as an emerging manager, why secondaries have become a primary driver of liquidity in venture, and how to navigate SPVs as a GP and LP.We also talk through the AI products they built to evaluate fund managers at Allocate, and how AI is changing venture and company building.A special thanks to Bolt and Warp for supporting this episode.Bolt: Join the world's largest hackathon - up to $1m in prizes. Sign-up here.Warp: Automates payroll, handles multi-state tax compliance, and streamlines international contractor payments, so founders can focus on building, not busywork. Try it here.Timestamps:(5:31) Evolution of the private markets(17:55) VC markets post-2020(21:09) Risk / return profiles of various fund sizes(24:04) Secondaries will drive future venture returns(33:17) Creative ways to return capital(36:27) “Curiosity Revenue” in AI(41:52) Allocate's Beyond Summit(43:42) Samir's AI fund analyzer(46:15) Fintech only 1% of financial services revenue(50:13) Triple-layered SPVs(54:50) Breaking down returns in venture(58:27) How to gauge a fund manager's access(1:00:14) Determining appropriate fund size(1:05:02) 90% of venture funds cannot raise right now(1:09:50) How to raise a fund today(1:15:37) ChatGPT roasts Banana Capital(1:19:56) Traits of the best VCs(1:22:41) Vetting grit, hustle, and obsession(1:31:12) Why using AI is table stakes(1:36:49) Value of podcastsCheck out AllocateThe Peel episode with Eric Vishria Samir's Venture Unlocked PodcastFollow SamirTwitterLinkedInFollow TurnerTwitterLinkedInSubscribe to my newsletter to get every episode + the transcript in your inbox every week.

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

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

Sanjit Biswas is the Co-founder and CEO of Samsara, the fleet management and safety platform.At the time of publication, Samsara is a public company worth over $26 billion, and we unpack how exactly they went from zero to run rating at over $1.5 billion in revenue in ten years.We get into using AI to impact the physical world, how Samsara uses AI internally, and how their products prevent over 200,000 deaths per year.Sanjit has built two unicorns, and he shares everything he's learned along the way, including what most founders and investors get wrong about hardware, thinking customer-first instead of product-first, how to know when you have product market fit, mastering sales as a technical founder, and how to spend more time with your customers.We also talk about getting his high school online in the 90's, and the research project that turned into Sanjit's first company, Meraki, and its $1.2 billion dollar sale to Cisco in 2012.Thanks to Bolt for supporting this episode. Help them break a world record for the largest hackathon (up to $1m in prizes): https://bit.ly/ThePeelBoltHackathonTimestamps:(4:26) Samsara: Helping the world of physical operations(8:44) Preventing 200,000 deaths per year(11:19) AI opportunities in transportation(14:43) Samsara's internal AI tools(16:58) What people get wrong when building hardware(19:04) Starting Samsara customer-first instead of product-first(22:23) Find adjacent products for your customers(26:28) How to know you have product market fit(34:52) How to spend more time with customers and build feedback loops(43:00) 70-20-10 framework for allocating capital(45:07) Importance of selling new products to existing customers(49:15) Revisiting the product roadmap based on new technology(50:38) Why Sanjit credits focus to hitting $1B revenue in nine years(53:41) Learning to love sales as a technical founder(57:06) Getting his high school online in the 90's(1:01:46) The research project that turned into Sanjit's first company, Meraki(1:04:01) Importance of asymmetric risk when starting a company(1:05:41) Early days of Meraki taking off(1:09:19) Surviving and doubling during the financial crisis(1:16:00) Cisco acquiring Meraki for $1.2B(1:18:15) Meraki's post-acquisition integration(1:20:48) Differences between 1st and 2nd company(1:24:19) Almost starting an renewable energy company(1:25:52) The power of small teams(1:28:49) One-shotting Bill Gates' biography at 10-years oldReferencedSamsara: https://samsara.com/Meraki: https://meraki.cisco.com/Arduino: https://www.arduino.cc/Raspberry Pi: https://www.raspberrypi.com/Hard Drive: Bill Gates and the Making of the Microsoft Empire: https://www.amazon.com/Hard-Drive-Making-Microsoft-Empire/dp/0887306292No Priors Podcast: https://www.youtube.com/@NoPriorsPodcastFollow SanjitLinkedIn: https://www.linkedin.com/in/sanjitbiswas/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/

Michael Kim is the Founder of Cendana Capital, a fund of funds that makes anchor investments in very early stage VC funds.We talk characteristics of the best investors, how Cendana does diligence on fund managers, portfolio construction best practices, Michael's “60x rule”, and why high ownership to fund size is the main driver of returns.We also get in to how VCs are using AI, the competition between Seed and multi-stage investors, why US endowments are under siege, and how secondaries are driving most early stage venture returns today.Michael also opens up about the early days of starting Cendana, the 18 month grind raising Cendana Fund 1, the day he almost died, and ranking in the top 2% globally in Call of Duty.Special thanks to Roger Ehrenberg, Kevin Hartz, Semil Shah, Jeff Claviar, Beezer Clarkson, Jack Altman, Jeff Morris Jr, Sheel Mohnot, Nichole Wischoff, Ted Alling, and Rick Zullo for their help putting this episode together.Thanks to Bolt for supporting this episode. Check out their world record largest (up to $1m in prizes) at: https://bit.ly/ThePeelBoltHackathonTimestamps:(4:24) The day Michael almost died(5:10) Call of Duty & video games(9:34) Hiring @ Cendana(10:31) How Cendana uses structured and unstructured data(16:51) How VCs are using AI(19:55) Why secondaries are driving most early stage venture returns(22:01) Deciding when to sell secondaries(24:28) Best performing venture funds ever(27:26) The best VCs have amazing access to the best founders(33:42) Why Cendana backs Solo GPs(35:57) How to invest over time and hype cycles(41:35) Why multi-stage firms are investing earlier(44:45) Cendana's current thesis: High ownership % to fund size(45:51) Why Cendana started backing non-lead VCs(48:41) How Cendana does diligence on fund managers(52:22) VC NPS Scores and Ron Conway's Silver Bullet(53:49) Good vs bad new VC firm strategies(56:36) Determining defensibility of a strategy(57:57) “Messy middle” software buyout fund(1:03:25) Portfolio construction best practice(1:08:11) Michael's 60x Rule(1:14:28) How Seed funds compete with multi-stage funds(1:20:05) Should you collect logos writing small checks?(1:21:07) Becoming an LP for the city of SF(1:24:42) Taking 18+ months to raise Cendana Fund 1 in the GFC(1:26:48) Warehousing the first Cendana Fund 1 investments(1:29:56) How to do a first close(1:34:29) Why it's hard to kill a VC firm(1:37:00) What happens to ZIRP tourist fund managers(1:40:22) How to raise a Fund 2 or 3 today(1:42:07) “US endowments are under siege”(1:44:55) What the best GP LP relationships look like(1:46:41) What Fund of Funds get wrong(1:50:43) The three most interesting trends in venture todayReferencedCheck out Cendana https://www.cendanacapital.com/Deep Checks https://www.deepchecks.vc/Prior episode with Eric at Bolt https://www.youtube.com/watch?v=7Q6n1vqUrF4Follow MichaelTwitter: https://x.com/MKRocksLinkedIn: https://www.linkedin.com/in/michael-kim-cendana-capital/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/

Mike Vichich is the Co-founder and CEO of Pursuit, which helps companies generate more revenue from the public sector.We talk about how AI is changing Helmer's 7 Powers, how it's impacting the government, if DOGE is actually working, building a startup in the Midwest, and how to disagree with your team.We also get into Mike's prior company Wisely, and how they went from $11 in the bank account and unable to pay payroll for six months, to over $10 million ARR and a $187 million exit to Olo, a public company.Thanks to Jack Altman and Blake Robbins for their help brainstorming topics for Mike!Timestamps:(3:21) How AI changes Helmer's 7 Powers(17:06) What becomes important in AI-first economy(21:02) How AI interfaces with the government(24:02) “The rules intended to save taxpayer money ironically cause taxpayer money to be wasted”(29:34) How change orders impact public sector costs(33:20) Why DOGE has not impacted US government spending yet(38:15) Three pieces of wisdom from 2nd-time founders(41:44) Starting Pursuit to make selling to the public sector as easy as the private sector(45:35) Why cities grow expenses 5x faster than tax revenue(51:42) Pros + Cons of building startups in Ann Arbor, MI(57:43) Hiring talent density in the Midwest(59:30) Starting his first company to fix consumer credit cards(1:08:50) Pivoting Wisely to restaurant loyalty(1:12:49) $11 in the bank, missing payroll for six months(1:15:21) Embarrassing demo at an Ann Arbor tech meetup(1:18:18) Why CEOs don't always have to be right(1:20:54) How to disagree(1:25:48) Hiring at Pursuit(1:28:30) “A bad day with customers is better than the best day in the office”(1:31:33) Crashing their first customer's PoS on Labor Day Weekend(1:35:55) Using “The Cadence” to hit $10M ARR(1:41:55) Selling Wisely to Olo for $187MReferencedCheck out Pursuit: https://www.pursuit.us/The Four Steps to the Epiphany by Steve Blank: https://www.amazon.com/Four-Steps-Epiphany-Steve-Blank/dp/0989200507Ann Arbor New Tech Meetup: https://www.meetup.com/a2newtech/How to Disagree: https://www.paulgraham.com/disagree.htmlThe Cadence by David Sacks: https://sacks.substack.com/p/the-cadence-how-to-operate-a-saas-startup-436aa8099e8Follow MikeTwitter: https://x.com/mikevichichLinkedIn: https://www.linkedin.com/in/mikevichichFollow 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/

Sam Ross is the Co-founder and CEO of Numeral.This conversation is a master class on all things growth at the zero to one stage. We talk early growth lessons from Airbnb, and stories from being one of the largest, earliest Facebook advertisers.We get into working backwards from pockets of strong demand to find business ideas, how to establish early social proof around your product, why you shouldn't hire a growth person as your first growth hire, how he raised Numeral's Series A in four days, and why sales tax is so complicated and how they're using AI to make it easy.Timestamps:(3:03) Why sales tax is so complicated(8:06) Running crazy Facebook ads in 2013(11:58) Why you need to be aggressive on new growth channels(16:55) How strong retention unlocks massive businesses (18:24) Using pockets of demand to find business ideas(21:34) Balancing performance vs brand marketing(25:45) How to build a brand from scratch(29:11) When cold outbound actually works(36:18) Building early social proof around your product(43:33) Don't hire career growth people for growth roles(49:31) Lessons building a jewelry business doing $30m in revenue(58:44) How the 2018 Wayfair v South Dakota decision led to Numeral(1:05:04) Hacking an early product together with spreadsheets(1:07:32) Automating the product(1:15:26) What happens if you don't pay sales tax(1:20:41) How Numeral uses AI and LLMs internally(1:26:41) How to compete against non-technical incumbents(1:32:57) Why they raised VC for Numeral(1:38:19) Raising a Series A in four days(1:45:43) How big can a sales tax company really be?(1:48:55) Creating a better global tax system(1:54:31) How San Francisco is losing its soulReferencedCheck out Numeral: https://www.numeralhq.com/South Dakota v Wayfair: https://en.wikipedia.org/wiki/South_Dakota_v._Wayfair,_Inc.Follow SamTwitter: https://x.com/SpamRossLinkedIn: https://www.linkedin.com/in/sambross/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/

Spenser Skates is the Co-founder and CEO of Amplitude.Our conversation gets into the importance of data in product design and company building, how Amplitude is thinking about AI, and the future of user responsive software.We also get into the early days of building Amplitude, when to go multi-product, how to construct your board as a startup, hiring executives at various company stages, lessons from closing three acquisitions, lessons scaling to $300 million in ARR, inside Amplitude's 2021 IPO, and what most people get wrong about Founder Mode.Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeelTimestamps:(4:45) Using data to build great products(8:31) Why data is existential to every business(13:14) How to go multi-product(15:48) Every startup becomes a distribution company(19:29) Lessons from three acquisitions(29:09) AI hasn't changed B2B SaaS yet(31:24) Challenges of incorporating AI in B2B SaaS(33:09) Amplitude's AI experiments(36:29) Navigating technology hype cycles as a public company(39:40) Amplitude's opportunity in LLMs(43:08) User responsive software(46:16) Surprising things that slow your speed of execution(51:27) What people get wrong about Founder Mode(59:48) Pivoting into Amplitude after YC(1:04:42) Nine months to raise Amplitude's first round(1:08:31) Surprises from closing the first customers(1:12:46) Two sales lessons for technical founders(1:13:44) Scaling to $300M+ ARR(1:17:14) How to choose board members(1:19:55) Inside Amplitude's IPO(1:21:56) “Stock price is an output of the business”(1:26:36) Evolving from startup founder to public company CEO(1:31:54) How hiring execs changes as you scale(1:34:32) Why DEI is important at Amplitude(1:39:46) Relevance of gaming and startupsReferencedTry Amplitude: https://amplitude.com/Careers at Amplitude: https://amplitude.com/careersMoxie Marlinspike's web3 article:https://moxie.org/2022/01/07/web3-first-impressions.htmlSheep Logic: https://www.epsilontheory.com/sheep-logic/Follow SpenserTwitter: https://x.com/spenserskatesLinkedIn: https://www.linkedin.com/in/spenserskatesFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

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

Colin Sidoti is the Co-founder and CEO of Clerk, the best way to build authentication and user management.I loved this conversation, because Colin is currently in the arena building Clerk. It has not been easy, and he takes us inside some of the harder moments of the past six years.We hit on three main themes: authentication; lessons raising multiple hard Seed extensions in the early days, including a recap before the A, and the demo that got a16z to invest; and things AI and MCP.We also talk founding a company with his brother, building a compound startup, why components are the new APIs, and what he learned about audacious goals from John Collison @ StripeA big thank you to Reid Christian @ CRV, Paul Klein @ Browserbase, and Joseph Nelson @ Roboflow for helping brainstorm topics for Colin.Timestamps:(3:39) The best developer tool for authentication and user management(5:45) The easiest way to set up billing(7:13) Building a compound startup(9:15) Lesson on audacious goals from John Collison(12:40) Developer tools are now trusted category experts(13:47) How auth impacts billing, CRM, marketing, analytics(19:44) Why auth is always changing(25:40) Coming up with the idea for Clerk(29:24) What its like starting a company with your brother(30:58) Living in a basement during Clerks early days(35:33) Getting early users narrowing focus in South Park Commons(40:10) Fundraising lessons from struggling to raise(43:46) The trick that raised Clerk's first round from S28(45:09) Launching + the first Seed extension(50:15) Sequoia's feedback that improved conversion rates(52:22) Why a16xz led Clerk's 2nd Seed extension(58:11) How to do a recap before Series A(1:03:34) Changing Clerk's pitch to scare investors(1:08:56) Fundraising advice “Why partner alignment is all that matters”(1:11:42) Fast Series A and breaking 7%/week growth(1:16:32) Negotiating Clerk's Series B at the bar(1:22:15) Investors in the arena vs in their mansions(1:27:57) The three ways AI is changing authentication(1:31:21) Why AI agents all try to steal free AI credits(1:33:09) Remember to have fun(1:36:24) Building a better product to compete in a crowded marketReferencedTry Clerk: https://clerk.com/Jobs at Clerk: https://clerk.com/careersMartin Casado's tweet https://x.com/martin_casado/status/1558134697753841664Try Inngest: https://www.inngest.com/Follow ColinTwitter: https://x.com/tweetsbycolinLinkedIn: https://www.linkedin.com/in/colin-sidoti-751a219Follow 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/

Filip Kaliszan is the Founder & CEO of Verkada, the physical security company.Verkada started in 2016 by building the best camera for physical security teams, and has since evolved into a full suite of security products for buildings. Filip takes us inside Verkada's rapid growth to almost a billion in annual revenue, over 2,000 employees, and raising capital from investors like Sequoia, Meritech, First Round, General Catalyst, and Next47.We get into how AI and LLMs are changing hardware, the power of customer therapy, how Filip iterated on early startup ideas, inside Verkada's very difficult first funding round, how signing their first big customers changed the trajectory of the business, and how to think about adding new products over time.We also talk through Verkada's commitment to in-person work in the summer of 2020, how you should evaluate joining a startup as an employee, Verkada's “software zero” employee bonus policy, and building a rooftop bar for the office.Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeelTimestamps:(4:20) Verkada, the physical security technology company + Demo!(11:02) Building software powered hardware(12:56) LLM opportunities in cameras(15:49) Filip's lifelong fascination with photography(17:57) Taking one year to come up with the idea for Verkada(22:27) Building his own home security system to learn the $16B market(27:14) Why hardware experimentation is cheaper and easier than you'd think(30:36) The importance of customer therapy(32:37) How to get your first customers, importance of quick time to demo(35:06) Why early fundraising was so hard(40:38) Verkada's first big customer(42:23) How to decide what startup to join(45:45) The opportunity in “smart building tech”(50:34) How to launch new product lines(58:07) Re-architecting the security industry to be software-native(1:02:31) How hiring and managing a team changes as you scale(1:08:55) Why each team at Verkada has its own recruiters(1:14:00) Adding senior leaders to the team as you scale(1:17:06) Evolving from introverted engineer to CEO of multi-thousand person company(1:21:59) Verkada's cool office and focus on in-person work during COVID(1:28:12) Building a rooftop bar on the office(1:32:20) Verkada's Software Zero employee bonus program with 40x ROI(1:36:00) How Filip thinks about IPO vs staying privateReferencedVerkada: https://www.verkada.com/Open roles at Verkada: https://www.verkada.com/careers/Follow FilipLinkedIn: https://www.linkedin.com/in/kaliszan/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/

Ofek Lavian is the Co-founder and CEO of Forage, the mission driven payments company.This is a special episode, because I'm an investor in Forage, and Ofek shares everything he's learned building the company. We go deep on food stamps, also known as EBT or SNAP, the government program that provides over $200 billion dollars per year in benefits that help 42 million low income Americans buy food.Our conversation gets into lessons from Ofek's time leading payments teams at Uber and Instacart, building Instacart's EBT program up to 40 employees and 10% of its total revenue, and why Ofek is so passionate about helping low income Americans.We get into the history of food stamps, market dynamics that led to low online adoption, the days Ofek thought Forage might not make it all the way to now working with the biggest players in online grocery, like Uber and DoorDash, and the long-term opportunity Forage has to build the rails the government uses to distribute trillions of dollars of restricted consumer benefits.Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeelTimestamps:(4:53) Forage: Helping 42m Americans buy food(5:24) History of food stamps & EBT(9:26) Growing up as an immigrant family with low food access(11:39) 90% of EBT recipients are elderly, disabled, or working parents(12:39) How Forage sells revenue to its customers(14:15) Building Instacart's EBT program during COVID(18:25) Why no one built an EBT payments product(22:13) Joining Forage as a Co-founder(25:01) Why government payments are so hard(30:25) Growing 15x in six months(33:52) Underdiscussed mental health challenges of startups(37:06) How the political environment impacts EBT(43:20) Why Forage charges more than competitors(45:58) Seasonality in EBT spend(46:59) Why early investors passed on Forage(48:10) The trillion dollar opportunity in restricted payments(50:56) “ There's no single idea that has destroyed more business value on planet Earth than the idea that micromanagement is bad.”(54:45) Why Forage doesn't care about job titles(58:51) Lessons backpacking across 28 countries after college(1:02:09) How to travel on a budget(1:04:24) Importance of health(1:06:15) Saving a friends life on Mount EverestReferencedForage: https://www.joinforage.com/Ofek's viral tweet: https://x.com/OfekLavian/status/1766950034581700697Follow OfekTwitter: https://x.com/OfekLavianLinkedIn: https://www.linkedin.com/in/ofeklavian/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/

Ed Lando is the Co-founder of Pareto, where he's been an early investor in over 25 unicorns, started and incubated over 10 companies, and was recently named the most active angel investor in the world according to Crunchbase.We get into how Ed first got started angel investing, how he built up deal flow, why he's historically kept a low profile, and why he hasn't raised outside capital.We also talk concentration vs diversification, why there's many ways to build successful companies, advice on hiring your first employees, and his playbook for incubating companies at Pareto, which is where he focuses most of his time. Timestamps:(0:00) Intro(2:51) Getting into angel investing(3:58) Debating high vs low PR strategies(8:27) How to start building deal flow when angel investing(10:00) Pareto: first investor in people leaving school or their job(12:05) Evolving from angel to fund(14:57) Why Ed didn't raise outside capital(20:33) Concentration vs diversification(28:29) Investing in non-sexy categories(32:50) There's no one right way to build a company(36:03) When to go against traditional wisdom(39:36) Lessons from his anti-portfolio(45:59) Ed's close relationship with his parents((49:04) How we're using AI(54:04) Incubating companies(58:38) Investing beyond spreadsheets and DCF models(1:05:49) How to trust your intuition investing (1:09:47) How to move fast(1:14:24) What most people get wrong when incubating companies(1:18:40) How to hire your first employees(1:26:27) Navigating hype when building and investing1:29:59 Venture math and the Power Law1:35:33 How Ed and Pareto's strategy might break1:38:45 Differences between the US and EuropeReferencedPareto: https://pareto20.com/Misfit Market: https://www.misfitsmarket.com/Catalina Crunch: https://catalinacrunch.com/Zamp: https://zamp.com/Magnus Carlsen on Joe Rogan: https://www.youtube.com/watch?v=ybuJ_nIXwGEFollow EdTwitter: https://x.com/edwardlandoLinkedIn: https://www.linkedin.com/in/edwardlando/Substack: https://edwardlando.substack.com/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Tommy Nicholas is the Co-founder and CEO of Alloy, the identity and fraud prevention platform trusted by over 700 financial service companies.Our conversation explores the early days of fintech, why more consumer financial protections actually lead to more fraud, and gets into the weeds of various tactics he's learned building a technical platform company like Alloy.We talk about embracing that the hard parts of company building are actually the best parts, why you're most likely to give up when things first start getting better, using hands-on sales implementations in the early days to gave Alloy product market fit on steroids, how hiring changes as you scale, getting 100's of no's over 20 months raising their Seed round, and why TAM doesn't matter.Thanks to Charley Ma for his help brainstorming topics for Tommy!Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try them here: https://bit.ly/NumeralThePeelTimestamps:(3:56) The platform to manage fraud(5:48) What fintech risk was like in the early 2010's(14:34) Why company building never gets easier(19:30) Reasons the hard stuff is actually the good stuff(24:00) You're most likely to give up when things start getting better(33:47) Doing hands-on sales implementation to get PMF on steroids(42:26) Deciding when PLG or hands-on sales will work best(52:33) Why more consumer financial protections leads to more fraud(58:14) 20 months to raise $2m vs $200m from a spreadsheet(1:06:32) “Make yourself look like a good investment”(1:10:14) Why TAM doesn't matter(1:14:35) How to hire collaborative problem solvers(1:24:38) Why Alloy didn't do much marketing early onReferencedTry Alloy: https://www.alloy.com/Charley Ma's Pod Episode: https://youtu.be/5cxgB1_q2lwTry Artie: https://www.artie.com/Follow TommyTwitter: https://x.com/tommyrvaLinkedIn: https://www.linkedin.com/in/tommynicholasFollow 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/

Mike Murchison is the Co-founder and CEO of Ada, the AI-powered customer service automation platform.Ada's product and scale puts Mike at the forefront at how AI is changing software and labor markets, and this conversation felt like both a glimpse into the future, and a look into the past, at a story of pure grit and determination, working seven customer service jobs at once.We talk about why management capabilities becomes even more important in AI-native companies, how customer service is changing from a cost center to a revenue driver, and how to talk to customers more as you scale.We also get into why AI is still underhyped, what truly AI native software looks like, the realities of selling enterprise AI software today, and advice for anyone building an AI agent from scratch.Thanks to Boris Wertz and Fahd Ananta for their help brainstorming topics for Mike!Timestamps:(00:00) Intro(03:49) Making customer service extraordinary for everyone(05:44) Management becomes more important in AI-first companies(12:13) From customer inquiry to solution in production, fully autonomously(16:01) Why companies talk to customers less as they grow(20:36) Creating new products from customer service data(22:45) Broken incentives in customer service(26:10) Working 7 customer service agent jobs at once for a year(37:19) Why pivoting to Ada felt like failure(46:11) How Mike would build an AI agent from scratch today(49:15) Ways AI will change how we build and manage companies(56:44) Why the best managers are great users of AI(1:00:27) How the top 1% of people are using LLMs(1:06:22) Realities of selling enterprise AI software today(1:11:02) Building a sales team from scratch(1:15:21) Reflecting on Ada's scale + doubling the last six months(1:16:41) Biggest software category of all-time ($750B)(1:19:51) Why AI is still under hyped(1:21:01) Ego is the biggest inhibitor to AI adoption(1:23:33) How AI will fuel explosion of creativity and productivity(1:25:20) Large companies will benefit the most from AI(1:27:41) Multi-modal language models and autonomous (computersReferencedTry Ada: https://www.ada.cx/Follow MikeTwitter: https://twitter.com/mimurchisonLinkedIn: https://www.linkedin.com/in/mikemurchisonFollow 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/

Cam Doody is the Co-founder and General Partner of Brickyard, the venture capital firm moving founders to Chattanooga, Tennessee to lock-in with no distractions until they find product market fit.Brickyard is one of the most unique venture firms you'll ever come across, and we get into how it how it was inspired by a 16x fund based in Chattanooga, why Cam and his co-founders started it during ZIRP, and why they hope everyone copies their model.We also get into Cam's startup Bellhops, which he started in 2011 and has since grown into the third largest moving company in the US. We talk running a local services business, why 5-star review systems don't work, and how U-Haul almost killed Bellhops overnight back in 2016.Thanks to Nader Khalil, Matt Harb, Austin Beveridge, and Spencer Levitt for their help brainstorming topics for Cam!Timestamps:(0:00) Intro(03:33) Chattanooga: Dirty manufacturing city to high tech(05:23) Brickyard's precursor, the Lamp Post Group (a 16x fund)(09:46) How ZIRP screwed up early stage investing(13:49) What is Brickayrd?(21:14) Getting Brickyard off the ground in 2021(26:25) 100+ year old rug warehouse + maintenance nightmares(33:13) Cam wants everyone to copy Brickyard(36:31) Why economic development startup programs don't work(38:59) YC teams doing Brickyard to escape the Trough of Sorrow(44:07) How Brickyard companies raise Series As(46:10) Nvidia acquiring Brev(52:18) How to deal with a co-founder breakup(55:45) Starting Bellhop to build a better moving company(1:02:27) How U-Haul almost killed them overnight(1:06:54) Marketing tactics for a local services business(1:12:05) Why 5-star review systems don't work(1:18:16) How Cam's view of VC's changed after becoming one(1:20:37) Ways VC's actually add value(1:25:05) The thesis for Bitcoin(1:39:21) Cam's annual remote desert island vacationReferencedCheck out Brickyard: https://www.justlaybrick.com/The Trough of Sorrow: https://andrewchen.com/after-the-techcrunch-bump-life-in-the-trough-of-sorrow/Bellhops: https://www.getbellhops.com/Follow CamTwitter: https://www.twitter.com/camdoodyLinkedIn: https://www.linkedin.com/in/cam-doody-b489a124Follow 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/

Eric Simons is the Co-founder and CEO of StackBlitz, best known for its breakout product Bolt, letting anyone build full stack apps from text, in the browser.Bolt launched in October of 2024, quickly growing from zero to a $20 million revenue run rate in two months, making it one of the fastest growing products ever. But Eric will be the first to tell you it wasn't an overnight success - the product didn't even work the first time they tried building it.We go behind the scenes of the seven year journey building the tech that eventually led to Bolt, how to avoid distractions, being capital efficient, living in a frat house for $100/month, and squatting in AOL's headquarters for $1/day when he was 19.Eric also takes us inside the weeks after Bolt's viral launch, figuring out a new business model on the fly, his strategy for fundraising and PR, why you should open source your code, Bolt's playbook for building a community around the product that enabled their viral launch, and how AI is changing software forever.Timestamps:(0:00) Intro(2:24) Building full stack apps from text, in your browser(4:19) Running an operating system in the browser(11:48) Why Bolt failed the first time, almost shutting down the company last summer(20:18) How Bolt went viral from one tweet(28:33) Differences between ChatGPT, Claude, Cursor(39:38) Why AI code gen changes the software world order(42:01) What happened inside Bolt going from zero to $20m ARR in two months(47:32) Not sharing fundraises publicly + his PR strategy(58:57) Why the team never gave up for seven years(1:01:07) Living in a frat house for $100/month(1:04:07) How to be capital efficient(1:09:00) Living on $1/day in AOL's HQ when he was 19(1:14:01) Inside Bolt's Series B(1:21:03) Bolt's hiring and product roadmap(1:32:58) Creating a new inference-based AI business model(1:38:07) Eric's playbook for building a community of users(1:44:05) Why you should open source your codeReferencedTry Bolt: https://bolt.new/Bolt on X: https://x.com/boltdotnewCheck out Webcontainers: https://webcontainers.io/$0 to $4m ARR case study with Anthropic: https://www.anthropic.com/customers/stackblitzBolt's open source code: https://www.bolt.diy/Bolt / StackBlitz is hiring! https://stackblitz.com/careersEric's favorite cafe, The Lighthouse SF: https://thelighthousessf.com/Lady Gaga's “one person” montage: https://www.youtube.com/watch?v=iRxsX_30tjsLiving inside AOL HQ at 19 years old: https://www.cnet.com/tech/tech-industry/meet-the-tireless-entrepreneur-who-squatted-at-aol/Bloomberg coverage of StackBlitz Series B: https://www.bloomberg.com/news/articles/2025-01-21/ai-speech-to-code-startup-stackblitz-is-in-talks-for-a-700-million-valuation?embedded-checkout=trueJoel Spolsky's blog: https://www.joelonsoftware.com/Follow EricTwitter: https://x.com/ericsimons40LinkedIn: https://www.linkedin.com/in/eric-simons-a464a664/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/

Rick Zullo is the Founder of Equal Ventures. Our conversation gets into Equal's unique approach to venture capital, thinking more like public market and private equity investors, and why they also think traction is overrated at Seed.We talk through Equal's thesis-driven model, employing a team of product owners, only investing in only 3 to 5 themes at once, and Rick's admiration of Charlie Munger.We also talk AI - who will benefit the most, what he does and doesn't like in terms of investing in the space, why venture capital is not really venture capital anymore, and why it sucks to be a Seed investor right now.Rick also runs the Emerging Manager Circle, a group for emerging fund managers. We get into the origin story of the group, his own struggles raising his first fund, and why talent is leaving the mega funds.Timestamps:(00:00) Intro(03:38) Why venture capital isn't venture capital anymore(11:33) How founders should approach raising a Seed round(14:13) The realities of downrounds(15:55) Rick's favorite founders that raised little capital(18:54) Biggest fundraising mistake founders make(21:21) Why we need to stop funding AI companies(28:34) How AI will benefit private equity the most(33:30) Three levels of opportunity in AI right now(38:36) Why traction is overrated at Seed(41:38) Investing in businesses with compounding returns on capital(52:07) VC lessons from PE firms(56:24) Why Seed investing sucks right now(1:04:15) The beauty of small exits(1:12:52) How failing to start a fund in college led to Equal Ventures(1:20:06) The struggle raising Equal's $55m Fund 1(1:23:23) Why the best talent is leaving mega VC firms(1:30:16) The Emerging Managers CircleReferenced* Equal Ventures: https://www.equal.vc/* EMC Summit: https://www.emcsummit.com/Follow RickTwitter: https://x.com/Rick_ZulloLinkedIn: https://www.linkedin.com/in/rickzullo/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/

Villi Iltchev is the founder of Category Ventures, where he invests early in enterprise software startups. And he's done it longer than almost anyone, building Salesforce's corporate venture arm and investing early in companies like Airtable, Zapier, GitLab, Remote, Hubspot, Gusto, and Box. Fresh off raising his $160m Fund 1, we get into the opportunity he saw to start Category, and how San Francisco and Silicon Valley have changed over the past 30 years. He also shares his story growing up as an illegal immigrant in Greece, moving to the US by himself in high school, the biggest mistake of his career, advice for founders selling their company, why unit economics and profitability always matters, how developer tools went from terrible to amazing businesses, the mistake that almost killed GitLab after he invested, and why you should raise your seed round from a seed fund. Timestamps: (00:00) Intro (03:22) Illegally immigrating from Bulgaria to Greece (05:14) Moving to the US by himself in high school (13:15) Moving to SF in the Dot Com Bubble (15:49) How SF changed over the last 25 years (22:27) Why HP fell from the top of Silicon Valley (25:36) Building Salesforce's corporate VC arm (30:29) Why SaaS was so transformative (34:35) Angel investing in Airtable (39:52) The biggest mistake of his career (42:13) Why unit economics always matter (47:20) Biggest mistake when selling a tech company (49:00) Almost starting a software PE firm and landing in VC (55:45) Lessons from August Capital + Evolution of venture (59:22) Early days of dev tools + Investing in GitLab (1:09:50) Why being contrarian is dumb (1:11:45) How GitLab almost died and emerged stronger (1:16:48) Villi's journey to starting Category (1:25:22) Category's thesis (1:30:48) Why startups always come in batches (1:31:57) The importance of track record in venture (1:35:32) Deciding a $160m fund size (1:39:26) Why you should raise seed rounds from seed firms (1:43:40) What Villi looks for in a startup Referenced Category VC: https://www.categoryvc.com/ Category's $160m Fund 1: https://www.forbes.com/sites/alexkonrad/2024/12/17/villi-iltchev-raises-160-million-debut-fund-category/ Aaron Levie (Box) on The Peel: https://youtu.be/cLn_tqPvNf4 GitLab's Recovery Stream: https://www.youtube.com/watch?v=v0TRHLvYGE0 Guy Podjarny (Snyk) on The Peel: https://youtu.be/BzKlZ_v4uCw Why SaaS won't consolidate: https://medium.com/@villispeaks/why-saas-consolidation-is-not-happening-2b9b722e0250 Follow Villi Twitter: https://x.com/villi LinkedIn: https://www.linkedin.com/in/villi04/ 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/

Rahul Sidhu is the co-founder of SPIDRTech and Aerodome, two companies in the public safety space.He's sold both of them, and our conversation unpacks all the lessons he learned, what he did differently with his second company Aerodome, and why he sold only 17 months after starting it.If you tuned into last week's episode, Paul told us to never talk to the cops. Rahul gives us the other side of the story, sharing his playbook for selling to police, the government, how he met Nikita Bier in high school, and why he's still bullish on drones, robotics, and AI in the physical world.Timestamps:(00:00) Intro(04:07) What its like testifying to Congress(08:06) Why 90% of what he knew about police was wrong(13:15) How to sell to police departments(15:24) His first business selling WoW accounts(19:00) Meeting Nikita Bier in high school(21:29) Starting SPIDRTech to improve police + community relationships(27:45) Two biggest mistakes building SPIDR(31:47) How startups break down when scaling(34:19) Selling SPIDR instead of raising a Series B(40:12) Why Aerodome was so much easier to start(42:55) Why Rahul loves unsexy markets with founder market fit(46:03) Starting Aerodome, drones as first responders(53:39) Building a capital efficient hardware startup(56:46) How regulatory changes made an opening for Aerodome(01:00:13) Inside Aerodome's Series A(01:03:57) Selling Aerodome to Flock Safety within 17 months(01:09:31) Saying “would I work for this team?” when getting acquired(01:14:35) Seeing a homeless guy in an Aerodome shirt(01:17:02) The massive Robotics + AI opportunity this decade(01:21:42) What's really happening with drones in New JerseyReferenced:SPIDRTech: https://www.spidrtech.com Aerodome: https://www.aerodome.com/ Nikita Bier's Ted Talk: https://www.youtube.com/watch?v=k9QTVII_lkg Follow Rahul:Twitter: https://x.com/rahoolsidoo LinkedIn: https://www.linkedin.com/in/rahulsidhu/ 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/ 

Paul Klein is the Founder and CEO of Browserbase, building infrastructure for AI browsers.Our conversation gets into the future of software and AI agents, why authentication is a huge problem in AI, how the best infrastructure companies become product companies, and the memo he wrote that convinced him to start Browserbase despite not wanting to build another company.A year ago, Paul was a relatively unknown commodity, and definitely did not want to raise venture capital again. He shares the playbook he used to go from zero to raising $27 million in nine months “as a non-famous person” (his words).He shares all his lessons learned in the arena as he's processing them, like what he thinks will unlock better AI agents, why you should like your own tweets, and how Browserbase competes with incumbents.Timestamps:(00:00) Intro(02:39) How LLMs unlock automation online(08:34) The future of software (AI agents)(11:21) Why AI agents need better authentication(12:59) Lessons from Twilio on building an infrastructure company(17:27) Learnings from his first startup(19:56) Bubbles, and how they drive innovation(20:37) Reasons this moment in AI is special(29:58) Why technical founders love post-PMF(31:55) The memo that started Browserbase(34:09) Why a startup should be a means of last resort(36:53) Being a solo founder(42:24) Importance of in-person culture(45:56) The best place to find engineers(48:34) How Paul hired a contractor army to build Browserbase(50:16) Why you can't hire mercenaries(54:28) The power of emojis in marketing(57:39) Browserbase's early growth playbook (3 videos)(01:04:00) Benefits of sharing an office with other startups(01:06:00) Sales lessons from his parents(01:08:07) Why startups are like video games(01:13:43) Successful founders work the hardest and are shameless(01:18:44) Customer support is a startups greatest differentiator(01:22:06) Paul's playbook that raised $27m in nine months as a non-famous person(01:29:03) How investors make decisions(01:33:10) Risks help startups avoid competition(01:36:37) Great infrastructure needs its own frameworks(01:39:05) Long-term thinking in LLMs will enable mass AI agents(01:42:21) Avoiding tech debt with AI moving so fast(01:43:48) Infrastructure companies need to become product companies(01:46:54) The Sine Wave philosophy to startupsReferenced:Browserbase: https://www.browserbase.com/ An Internet Browser for AI: https://memos.hawkhill.ventures/p/an-internet-browser-for-ai Rise of the Product Engineer: https://memos.hawkhill.ventures/p/rise-of-the-product-engineer Death to the Backend: https://memos.hawkhill.ventures/p/death-to-the-backend The three Browserbase marketing videosPre-Seed: https://x.com/pk_iv/status/1775183751800377344 Seed: https://x.com/pk_iv/status/1798731220005883935 Series A: https://x.com/pk_iv/status/1851270308701106383Follow Paul:Twitter: https://x.com/pk_iv LinkedIn: https://www.linkedin.com/in/paulkleiniv/Follow Turner:Twitter: https://x.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/ 

You're probably familiar with Baiju Bhatt's work as the co-founder of Robinhood. But he's also obsessed with space, and recently started Aetherflux, a space solar power company.We get into the physics of using lasers to beam solar power to the Earth, Aetherflux's early roadmap, and how he went from zero to one going from building software to physical products.We also talk through the early days of Robinhood, getting turned down by hundreds of early investors, the accidental launch, how to know if you really have product market fit, how Aaron Levie at Box helped get Robinhood.com, the value of creativity and design, Baiju's philosophies on combining qualitative and quantitative user research, and his favorite animal and classic car. He also tried to cut my hair.Timestamps:(00:00) Intro(02:31) Aetherflux: a space solar energy company(02:50) Origins of space solar power in the 40's & 70's(10:31) Safely beaming energy from space to Earth with lasers(13:46) Building floating space solar farms(21:27) Aetherflux's early roadmap(27:08) Growing up with dad as a Physics professor(32:18) Going zero to one building physical products(35:15) Baiju's favorite car, attempting a haircut, contemplating mustaches(38:27) Trying to prove Einstein wrong(41:42) Meeting Robinhood Co-founder Vlad at Stanford(44:10) Starting an algorithmic trading company(46:41) The beginnings of Robinhood(52:04) Getting turned down by hundreds of early investors(56:49) How they convinced Tim Draper to invest(59:39) Getting Robinhood.com because of Aaron Levie(01:01:28) Accidentally launching on a Friday afternoon(01:03:09) How to know if you have Product Market Fit(01:06:35) Combining qualitative and quantitative user research(01:14:23) Loving cats despite being allergicReferenced: Robinhood: https://www.robinhood.comAetherflux: https://www.aetherflux.com/TechCrunch coverage: https://techcrunch.com/2024/10/09/billionaire-robinhood-co-founder-launches-aetherflux-a-space-based-solar-power-startup/Seinfeld mustache scene: https://www.youtube.com/watch?v=DzZsLaLChRgThe Michelson–Morley experiment: https://en.wikipedia.org/wiki/Michelson%E2%80%93Morley_experimentEpisode with Aaron Levie @ Box: https://www.youtube.com/watch?v=cLn_tqPvNf4Follow Baiju:X/Twitter: https://x.com/BaijuBhatt LinkedIn: https://www.linkedin.com/in/bprafulkumar Follow Turner:X/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/   

Sheel Mohnot is the Co-founder of Better Tomorrow Ventures, an early stage fintech focused fund leading rounds in pre-seed and seed-stage companies.Our conversation weaves through Sheel's two decades of building and investing in fintech, starting BTV, and why they started a fintech-focused accelerator, The Mint.Fun facts on Sheel, he was a contestant on the Zoom Bachelor during COVID lockdowns, in a Justin Bieber music video, got married in the Taco Bell Metaverse, and was once banned from Uber.We talk lessons competing against Stripe before selling his first company, common fintech startup pitfalls, and the trick every VC should use when fundraising.Timestamps:(00:00) Intro(03:13) Why fintech makes disproportionate positive change(07:49) Most interesting opportunities in fintech today(09:09) The accountant shortage(12:59) Common early fintech startup pitfalls(16:09) Building Fee Fighters to cut payment processing fees(21:15) Lessons competing with Stripe(21:57) Getting acquired by Groupon and adding $600m in market cap(25:11) Biggest first-time startup mistakes(29:21) Getting $10k in Uber credit via paid Google ad(32:13) Investing in Flexport(36:19) Navigating hot vs underhyped rounds(43:39) Sheel's domain auction company(53:18) How he started angel investing(54:57) Spotify acquiring his podcast “The Pitch”(59:55) Why accelerators succeed and fail(01:06:07) The Mint, BTV's fintech-focused accelerator(01:09:56) Camp BTV in the Santa Cruz Mountains(01:11:41) Early days of NerdWallet(01:14:55) Raising $75m BTV Fund 1 with Jake to fill a gap in the market(01:18:36) Understanding Fund of Funds incentives(01:22:15) Importance of references in VC fundraising(01:24:02) $150m BTV Fund 2(01:27:13) Importance of following-on when leading roundsReferenced:BTV: https://www.btv.vc/ The Mint: https://www.themint.vc/ Fee Fighters: https://techcrunch.com/2011/09/23/feefighters-launches-payment-gateway-samurai/ Follow Sheel:Twitter: https://x.com/pitdesi LinkedIn: https://www.linkedin.com/in/smohnot/ 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/ 

Chris Hulls is the co-founder and CEO of Life360, the social network for families. At the time of recording, its the 15th largest app in the US, with over $330 million in annual revenue, and valued at over $3 billion in the public markets.We go inside the two decade journey building Life360, competing against Sam Altman and Woz, almost getting cancelled on TikTok, and going public twice - first in Australia, then again in the US.Timestamps:(00:00) Intro(02:04) Why CEO's are getting more authentic(04:59) Building a social network for family(08:14) Starting Life360 after Hurricane Katrina(12:23) $30k from mom and a professor(13:52) $300k grant from Google(16:13) Launching on the first Android phones(18:20) Competing against Sam Altman, Steve Wozniak(19:06) “If we trusted the data, we would've shut down”(24:22) Why doubters lead to less competition(25:49) Fundraising in an unsexy market(32:21) Almost getting cancelled on TikTok(41:42) Building a contextual advertising business(48:36) Acquiring Tile, launching hardware products(52:41) Defeating patent trolls(57:22) IPO'ing in Australia and the US(01:01:00) Why its hard to go public below a certain size(01:07:50) 70% drop in downloads during COVID(01:10:03) Get to know your competitors(01:15:05) Lean Startup philosophy went too far Referenced:Try Life360: https://www.life360.com/ Wheels of Zeus: https://en.wikipedia.org/wiki/Wheels_of_Zeus Chris' TikTok journey: https://www.entrepreneur.com/leadership/how-life360s-founder-dealt-with-teens-mocking-him-on-tiktok/457879 Chris' TikTok: https://www.tiktok.com/@life360ceo Follow Chris:Twitter: https://x.com/ChrisHulls LinkedIn: https://www.linkedin.com/in/chrishulls/ 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/ 

Joseph Nelson is the Co-founder and CEO of Roboflow, making the world programmable by building computer vision tools for developers and enterprises. We talk about how computer vision creates a new paradigm to program the world, and how visual AI is the missing piece of AGI. Joseph also shares multiple live product examples, how computer vision unlocks new data sources, lessons from Stripe and Palantir, building business models in developer tools, his experience working with David Sacks, and developer marketing tactics and how Roboflow consistently gets to the front page of Hacker News.Timestamps:(00:00) Intro(03:34) Computer vision is the missing piece for AGI(05:59) Vision as a new paradigm to collect data(10:55) Live examples of computer vision(13:45) How a Magic Sudoku solver app led to Roboflow(18:13) Using computer vision for automation(24:49) Computer vision in sports(27:02) How vision unlocks new data sources(28:24) Inside developer tool business models(33:32) The "Collison Install" and hands-on customer service(36:45) When to adopt Palantir's Forward Deployed Engineers(43:44) Why AI companies need to combine PLG and enterprise sales(50:12) Advice on developer marketing(52:30) Roboflow's greatest hits on Hacker News(01:02:19) Benefits of David Sacks as AI & Crypto Czar(01:05:32) Why all new technology has bad actors(01:07:07) Why over-regulation holds back innovation(01:12:01) How to get on the front page of Hacker News(01:19:43) Multi modality, time recognition, and agentic vision(01:28:36) Image-to-image prompting(01:30:42) Growing up in Iowa(01:32:20) Making TI-84 calculator games in high school(01:36:32) Pioneer: hunger games for startups(01:40:16) Why Roboflow does weekly Ship Lists + Ship and Tell(01:42:46) Hiring former founders and "full stack people"(01:45:16) Designing a bottoms-up organization while scaling(01:50:35) Why candidates build with Roboflow in hiring process(01:55:08) Hiring someone to help with the podcastReferenced:Robowflow: https://roboflow.com/ Roboflow Universe: https://universe.roboflow.com/ Paint.wtf: https://paint.wtf/ Roboflows NeurIPS Presentations: https://blog.roboflow.com/neurips-2023-papers-highlights/ Careers at Roboflow: https://roboflow.com/careers Follow Joseph:Twitter: https://x.com/josephofiowa/ LinkedIn: https://www.linkedin.com/in/josephofiowa 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/ 

Austin Rief is the Co-founder & CEO of Morning Brew, building the Wall Street Journal for the next generation. They started the company in 2017, and grew it to 6 million subscribers and $70 million in revenue in six years. We talk through the journey starting Morning Brew with Co-founder Alex Lieberman while students at the University of Michigan, and Austin's playbook for starting a new media company from scratch today. We get into the creator economy, early stage investing, ad based business models, being the first advertiser on Instagram Stories, advice for hiring, and his secret for sourcing remote talent in Sri Lanka. Timestamps:(00:00) Intro(03:42) How to start a media company from scratch today(13:01) Future of the creator economy is niche products(14:42) Opportunity in B2B media today(17:05) Reflecting on investing during ZIRP(21:30) Why its starting to feel like 2021 again(23:16) Talking VC portfolio math(27:09) Starting Morning Brew with Wall Street interview prep(33:35) Being so dumb that they never pivoted from being a newsletter(35:29) How newsletter business models works(38:32) Morning Brew's first viral Instagram post(40:37) Acquiring subscribers for two cents on Instagram Stories(42:29) Nik Sharma's poor mans paid ads strategy(44:32) Landing Discover as their first big sponsor(46:06) How agencies and ad buying works(49:49) Why sales roles are so hard to hire for(53:04) Importance of offsheet references(57:43) Sourcing talent in Sri Lanka with Oceans(01:04:23) Austin and Alex's unique co-founder dynamics(01:07:16) Dental plans, rotisserie chickens, and company laptops(01:10:00) Building WSJ for the next generation Referenced:Morning Brew: ⁠https://www.morningbrew.com  ⁠  Try Oceans: ⁠https://www.oceanstalent.com/ ⁠ Kevin Espiritu episode: ⁠https://www.youtube.com/watch?v=FefGL-qPzDo⁠ Craig Fuller episode: ⁠https://www.youtube.com/watch?v=oPPqO8eBq2M⁠ Forbes article: ⁠https://www.forbes.com/sites/hayleycuccinello/2019/02/07/morning-brew/⁠  Follow Austin:Twitter: ⁠https://x.com/austin_rief⁠ LinkedIn: ⁠https://www.linkedin.com/in/austin-rief/⁠ Newsletter: ⁠https://www.theaustinbrief.com/⁠  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/⁠ 

Niels Hoven is the founder of Mentava, building software to accelerate kids' education, starting with teaching two year old's to read. We talk about how public education isn't designed for ambitious kids, the power of hater marketing, product design from zero to one, how too much data leads to Frankenstein products, Seed stage fundraising advice, parenting hacks, why AI won't have a big impact on education, and the future of elite higher ed. For full show notes, visit: https://highlightai.com/share/0a0869a7-c345-4974-ba2b-726bacf7a534   Timestamps:(00:00) Intro(03:49) Why schools don't challenge overachievers(11:58) The hater that made Mentava go viral(18:14) The secret that teaches little kids to read(24:22) How people actually learn to read(27:35) 2/3 of 4th graders can't read proficiently(29:29) The downfall of one-size fits all education(33:44) How California almost banned middle school algebra(40:41) SF's lottery system and how it impacts low income families(42:41) How COVID changed education(47:41) Early prototypes and going all-in on Mentava(50:56) Best practices from gaming in education(55:10) Raising a party round from lots of angels(01:03:03) Designing business models in education(01:13:19) Being pro-tech + anti-screens for kids(01:18:04) Top parenting hacks(01:22:53) How data-driven product design leads to Frankenstein products(01:25:34) Why gaming's the best industry to learn how to build product(01:27:46) The trick Niels used to find startup ideas for 20 years(01:31:03) Why AI won't be that impactful in education(01:36:28) What happens to elite higher education over the next decade(01:43:15) Admiring Stripe Referenced:Mentava: https://www.mentava.com/ Ryan Delk podcast episode: https://open.spotify.com/show/3QqtxGHqsPnKTG4CS7NgX5  | https://youtu.be/GTfsMEOIIxQ  How Neils raised Mentava's Seed round: https://www.mentava.com/blog/how-i-got-50-high-profile-angel-investors-to-join-our-seed-round  Mentava's Alphabet Book: https://www.mentava.com/alphabet-sounds-book  | https://www.amazon.com/Mentavas-Alphabet-Sounds-Niels-Hoven/dp/B0DKTQ9FW4   Follow Niels:X / Twitter: https://x.com/NielsHoven  LinkedIn: https://www.linkedin.com/in/nielshoven   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/  

Nirav Tolia is the co-founder and two-time CEO of Nextdoor. He started the company in 2011, stepped down as CEO in 2018, watched the company go public in 2021, and re-joined as CEO the summer of 2024. He also founded Epinions which IPO'd in 2004, and before that was an early employee at Yahoo. We go inside the decision to re-join the company after he thought he'd never come back, and how Nextdoor's trying to act like a startup while running a public company. He also takes us back to the very early days of Nextdoor, the deliberate product decisions that made growth hard but led to 100M+ neighbors on the platform, the lessons learned operating his first company through the Dot Com Bubble, and what it was like being a guest shark on Shark Tank. For full show notes, visit: https://highlightai.com/share/d7bcd655-9b2f-47f7-a6e3-fdf3e109c97e  Recommended Podcast:

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, 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: Ahrefs: Follow Daryna: Twitter: LinkedIn: Follow Turner: Twitter: LinkedIn: Subscribe to my newsletter to get every episode + the transcript in your inbox every week:

Lisa Rapuano is a retired professional investor, known for outperforming the market 15 years in a row in the 90's and 2000's. We go deep on how she beat the market, including early investments in AOL, Dell, and Amazon, and lessons learned from Jeff Bezos and Michael Dell. We also talk about 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 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 (47:26) 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 (01:09:17) The downsides of high valuations (01:12:45) Almost wiring back the Seed round (01:16:37) Why every fundraise is a Pipeline problem (01:23:09) 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 Levy is the visionary behind the Twitter account Car Dealership Guy and media company. Yossi 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 then pivoting to build a thriving B2B automotive media empire. Yossi shares the innovative marketing strategies, the hard lessons learned 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 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 ultimately 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 Plymoth, 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. He takes us inside key moments from his 8+ year journey at Instacart scaling the company to over $10 billion. He also discusses strategies for customer research and building customer relationships, 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/