Episodes
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I just attended Allocate’s Beyond Summit in Deer Valley Utah. It was a peek into what the top VC's and LP’s are thinking about right now.
Allocate asked me to record an episode of the show, live from the conference.
So I asked everyone “What’s your hottest take on the VC market today?”
Thank you to Numeral, Flex, and Amplitude for supporting this episode
Numeral: The end-to-end platform for sales tax and compliance https://www.numeral.com
Flex: Get premium banking and a net 60 day credit card at 0% APY https://home.flex.one/referral/bananacapital
Amplitude: AI analytics, all you have to do is ask https://www.amplitude.com
Timestamps:
(1:22) Seed investing is dead (Tripp Jones, Uncork)
(5:56) Seed is not dead (Bryan Rosenblatt, Sandlot)
(13:19) Most consensus era of VC ever (Nate Williams, Union)
(18:02) Taking the Power Law Pill (Pratyush Buddiga, Susa Ventures)
(29:15) The 2nd-time founder premium is dead (Matt Cohen, Ripple Ventures)
(32:46) AI will crush intelligence labor (Clark Cheng, Merrimac)
(42:25) New deep tech investors will lose their shirts (Sunil Nagaraj, Ubiquity Ventures)
(46:39) ChatGPT for robotics is still 15 years away (Sungjoon Cho, Fortitude Ventures)
(52:07) The app layer ARR reckoning (Josh Christensen, Mercato)
(58:30) The AI bubble will pop in Q2/Q3 (Amias Gerety, QED)
(1:08:22) Most individuals do VC wrong (Jon Oberheide)
(1:15:25) Allocators have become too allocator-y (Dan Feder, University of Michigan)
(1:20:55) LP’s should value information, not just returns (Ben Ivey, Marshall Street)
(1:24:09) Upcoming litigation of Russian doll SPVs (Asher Siddiqui, Song United)
(1:30:13) Why retail needs private market access (Sarah Pinto Peyronel, Robinhood Ventures)
Referenced
https://beyondsummit.allocate.co/
Tripp Jones, Uncork Capital
Twitter: https://x.com/thistrippjones
Bryan Rosenblatt, Sandlot
Twitter: https://x.com/BRosenblatt4
Nate Williams, Union
Twitter: https://x.com/naywilliams
Pratyush Buddiga, Susa Ventures
Twitter: https://x.com/pratyushbuddiga
Matt Cohen, Ripple Ventures
Twitter: https://x.com/mattybcohen
Clark Cheng, Merrimac
LinkedIn: https://www.linkedin.com/in/clark-cheng-cfa-frm-caia-a411535
Sunil Nagaraj, Ubiquity Ventures
Twitter: https://x.com/sunilnagaraj
Sungjoon Cho, Fortitude Ventures
Twitter: https://x.com/josungjoon
Josh Christensen, Mercato
LinkedIn: https://www.linkedin.com/in/joshjdmba/
Amias Gerety, QED
Twitter: https://x.com/amiasmg
Jon Oberheide
Twitter: https://x.com/jonoberheide
Dan Feder, Michigan
LinkedIn: https://www.linkedin.com/in/danfeder
Ben Ivey, Marshall Street
LinkedIn: https://www.linkedin.com/in/benivey
Asher Siddiqui, Song United
LinkedIn: https://www.linkedin.com/in/ashersiddiqui
Sarah Pinto Peyronel, Robinhood Ventures
Twitter: https://x.com/SPintoPeyronel
*This podcast is produced by Allocate for informational and educational purposes only and is intended for institutional, accredited, and qualified investors. Nothing discussed constitutes an offer to sell or solicitation to purchase any security or advisory service, and nothing should be construed as legal, tax, or investment advice. Any offering will be made only pursuant to applicable confidential offering documents.
Views expressed by participants are their own and subject to change. Any discussion of target returns, projected outcomes, IRRs, MOICs, or other performance metrics is hypothetical and illustrative only and should not be relied upon as an indication of future performance.
Investments in private funds are speculative, illiquid, and involve substantial risk, including possible loss of the entire investment. Past performance is not indicative of future results.
Certain guests may have financial or other interests in the opportunities discussed. Allocate Management Company, LLC is an SEC-registered investment adviser. Registration does not imply any level of skill, training, or SEC endorsement. Please consult your own advisors before making any investment decision.*
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Alfred Wallforss is the Co-founder of Listen Labs, the AI customer research company.
Companies like Microsoft use Listen to run AI-powered customer interviews, and Alfred talks about how they first landed them as a customer at a pitch competition.
We talk why startups should pursue enterprise customers early on, why 85% of survey answers are random clicks, how AI is changing the $140B market research industry, leveraging VC’s for customer intros, how to stand out when recruiting as a startup, and hiring for obsession.
Thank you to Numeral, Flex, and Amplitude for supporting this episode
Numeral: The end-to-end platform for sales tax and compliance https://www.numeral.com
Flex: Get premium banking and a net 60 day credit card at 0% APY https://home.flex.one/referral/bananacapital
Amplitude: AI analytics, all you have to do is ask https://www.amplitude.com
Timestamps:
(0:14) Listen: AI customer research tool
(7:30) Fraud is a big problem in customer research
(9:06) The $140B customer survey industry
(12:08) Why running customer surveys is so hard
(16:03) AGI will never replace humans
(18:25) Surveys vs interviews
(21:13) Importance of emotion in data collection
(22:54) Using AI interviews to get product feedback
(26:15) Building digital twins creates better data
(32:22) Outperforming generic AI tools
(34:17) Sweetgreen’s Max Protein Bowl
(36:09) Jevon’s Paradox in customer research
(40:37) Quantitative vs qualitative
(42:38) Landing Microsoft as an early customer
(44:50) Targeting enterprise customers from day 1
(48:05) Building a VC customer intro leaderboard
(51:53) Recruiting with billboard games
(57:20) Hiring for obsession
(1:02:07) Alfred’s favorite movies
(1:03:53) Listen’s custom agent harness
(1:06:24) Velocity Fellowship for Swedes moving to SF
(1:08:34) Growing up with entrepreneurial older brother
(1:09:46) No shoes in the office
Referenced
Try Listen: https://listenlabs.ai/
Careers at Listen: https://listenlabs.ai/careers
Sweetgreen protein bowls: https://listenlabs.ai/case-studies/sweetgreen
Toni Erdmann: https://www.imdb.com/title/tt4048272/
Episode with Erik @ Modal: https://www.thespl.it/p/building-ai-native-infrastructure
Follow Alfred
Twitter: https://x.com/itsalfredw
LinkedIn: https://www.linkedin.com/in/wahlforss
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/
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Episodes manquant?
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Tomasz Tunguz is the Founder and General Partner of Theory Ventures.
We talk about today’s “all out sprint” in AI, Anthropic’s strategy, the three layers of AI business models, how AI compares to prior technologies, where to invest in AI today, and what Theory looks for in new investments.
Thank you to Numeral, Flex, and Amplitude for supporting this episode
Numeral: The end-to-end platform for sales tax and compliance https://www.numeral.com
Flex: Get premium banking and a net 60 day credit card at 0% APY https://home.flex.one/referral/bananacapital
Amplitude: AI analytics, all you have to do is ask https://www.amplitude.com
Timestamps:
(0:42) The “all out sprint” in AI today
(1:40) Why GPU prices are up 116% in six weeks
(6:34) AI infra end-state: “We’ll over build”
(9:12) Tokenmaxxing, and why AI needs to get more efficient
(15:48) AI models will resemble pharma more than software
(19:52) Why Anthropic still trades at a discount
(25:42) Anthropic’s strategy: commoditize the compliments
(30:29) Why OpenClaw is so strategic for OpenAI
(34:08) The three layers of AI business models
(38:18) Where to invest in AI today
(45:49) Who will survive SaaSpocalypse?
(52:15) Comparing AI’s impact to historical technology cycles
(57:34) How new technology historically impacts jobs
(1:05:58) Where AI is underrated today
(1:10:41) How people are actually buying AI products
(1:14:06) Why Theory’s investing in ads, inference, and email
(1:16:24) 2026 IPO pipeline, how VC has changed over 20 years
(1:20:56) What Theory looks for in new investments
(1:22:32) Starting Theory Ventures in 2022
(1:25:39) Running a monte carlo analysis to determine portfolio construction
(1:27:54) Tomasz personal AI projects
Referenced
Theory Ventures: https://theoryvc.com/
Tomasz Blog: https://tomtunguz.com/
Follow Tomasz
Twitter: https://x.com/ttunguz
LinkedIn: https://www.linkedin.com/in/tomasztunguz
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/
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Ali Partovi is the Co-founder and CEO of Neo.
Neo started in 2017 as a network for the top college students. Neo is a “people-first” investor, a thesis it developed missing out on early investments in PayPal and Google at three employees.
Neo has since invested in the Seed rounds of Cursor and Kalshi, and Ali shares everything he’s learned about spotting outlier talent, how to hire the best people, how computer science is the best business education, and why the best entrepreneurs start young.
Special thanks to Hadi Partovi, Fuzzy Khosrowshahi, Alan Shusterman, and Claire Shorall for their help brainstorming topics for Ali.
Thank you to Numeral, Flex, and Amplitude for supporting this episode
Numeral: The end-to-end platform for sales tax and compliance https://www.numeral.com
Flex: Get premium banking and a net 60 day credit card at 0% APY https://home.flex.one/referral/bananacapital
Amplitude: AI analytics, all you have to do is ask https://www.amplitude.com
Timestamps:
(0:09) Neo’s two 10x funds
(2:19) Missing PayPal led to Neo
(9:32) Not investing in Google at 3 employees
(11:31) Backing Facebook despite the idea
(13:01) Starting Neo to help top college students
(17:21) How to identify outlier talent
(24:38) Neo’s coding test
(27:41) Bootstrapping the first cohort of Neo Scholars
(34:58) How Cognition President Russel Kaplan changed Neo forever
(39:21) Starting Neo after talking to Steph Curry
(46:42) Launching [Code.org](http://Code.org) to teach 20M kids to code
(59:38) Is coding still relevant in 2026?
(1:03:43) How to hire outlier talent
(1:07:25) Why you should aggressively apply for one job
(1:11:09) Neo Residency: $750k uncapped
(1:19:51) Growing up in Iran during the revolution
(1:26:03) Impact of the immigrant mentality
(1:29:15) Most entrepreneurial roots start very young
(1:39:18) Lessons investing in Cursor + Kalshi seed rounds
(1:50:27) Confession: a podcast about failure
(1:52:36) Fucking up a $50m deal by lying to Steve Jobs
Referenced
Neo: https://neo.com/
Neo Scholars Application: https://neo.com/scholars
Neo Residency: https://neo.com/residency
Code.org: https://code.org/
Lying to Steve Jobs: https://x.com/apartovi/status/1447251334814523392
Losing a deal with Yahoo: https://x.com/apartovi/status/1449856639331340289
Follow Ali
Twitter: https://x.com/apartovi
LinkedIn: https://www.linkedin.com/in/apartovi/
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/
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Jim Belosic is the Co-founder and CEO of SendCutSend, a sheet metal manufacturing business he bootstrapped to a $140 million revenue run rate in eight years.
We talk building a manufacturing business in the US, creative ways he financed the company early on, using speed and trust to compete with overseas competitors, lessons from restaurants, and why you can’t run a factory from a spreadsheet.
Thank you to Numeral, Flex, and Amplitude for supporting this episode
Numeral: The end-to-end platform for sales tax and compliance https://www.numeral.com
Flex: Sign-up for Flex Elite with code TURNER, get $1,000 https://form.typeform.com/to/Rx9rTjFz
Amplitude: AI analytics, all you have to do is ask https://www.amplitude.com
Timestamps:
(0:16) Automating sheet metal manufacturing
(5:59) Zero to $140 million ARR in 8 years
(7:58) Acquiring a $750k laser with $0
(13:38) Automating factories is like baking cookies
(15:17) Being legible to capital
(17:31) Unlocking custom, low order manufacturing with software
(20:00) Building more factories instead of selling the software
(24:50) Run your company like a lemonade stand
(28:30) Raising an angel round in 2021 as a safety net
(33:21) SendCutSend’s unique bottoms-up GTM
(38:24) Fun coupons
(40:12) Building a moat with speed and trust
45:55) How US factories can beat China
(47:40) Gaslight product launches
(52:05) Lessons from non-manufacturing businesses
(55:19) You can’t run a factory from a spreadsheet
(58:10) Using data in manufacturing
(59:50) Lessons from Factorio
(1:03:17) Unlocking a negative cash conversion cycle
(1:06:14) You need to resist automating everything
(1:13:51) Surviving COVID with six weeks of cash
(1:15:47) Solving the US skilled labor shortage
(1:26:17) Teaching kids about manufacturing
Referenced
SendCutSend: https://sendcutsend.com/
Careers at SendCutSend: https://sendcutsend.com/careers
Sandy Kory: https://www.linkedin.com/in/sandykory
Horizon VC: https://www.horizon.vc/
Concrete Canoe Competitions: https://www.asce.org/communities/student-members/conferences/asce-concrete-canoe-competition
Follow Jim
Twitter: https://x.com/jimbelosic
LinkedIn: https://www.linkedin.com/in/belosic
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/
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Alex Israel is the Co-founder and CEO of Metropolis.He unpacks the unique strategy they used as a tech startup to rollup parking lots and become the largest parking operator in the world.Thank you to Will Quist, Yoni Rechtman, Adam Bain, and Jamie Siminoff for their help brainstorming topics for the conversation.Thank you to Numeral, Flex, and Amplitude for supporting this episodeNumeral: The end-to-end platform for sales tax and compliance https://www.numeral.comFlex: Sign-up for Flex Elite with code TURNER, get $1,000 https://form.typeform.com/to/Rx9rTjFzAmplitude: AI analytics, all you have to do is ask https://www.amplitude.comTimestamps:(1:10) Helping 50m Americans park(4:00) Building “Buy Now” for the physical world(9:02) Real-world checkout technology that works(16:07) Why parking never institutionalized as an asset class(18:34) Using tech to make parking assets more valuable(21:53) Parking lots as autonomous robotics hubs(29:07) Going to film school, working at MTV(30:55) Starting his first parking data company(33:47) Culture of pranking each other(36:27) A Fortune 500 CEO convinced him to start a 2nd parking company(42:55) Realizing they couldn’t sell to real estate operators(46:09) Acquiring a company 10x their size to jumpstart GTM(50:20) How to do a successful AI growth buyout(54:48) Revenue growth must be driven by technology(1:00:33) Why companies should do growth buyouts(1:03:55) Being legible to capital(1:09:16) You need creativity to take risks(1:13:30) AI is the first ever disruption to skilled labor(1:19:14) CEO challenges growing zero to 23,000 employees(1:24:31) Alex’ personal AI stackReferencedMetropolis: https://www.metropolis.io/Careers at Metropolis: https://www.metropolis.io/careersRoy Amara: https://en.wikipedia.org/wiki/Roy_AmaraFollow AlexTwitter: https://x.com/Alex__IsraelLinkedIn: https://www.linkedin.com/in/alex-israelFollow 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/
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Karthik Duraisamy is a professor at the University of Michigan.
He is co-leading U of M's newly created Institute of Agentic Computing, the first of its kind. The institute will serve researchers and developers building agentic AI infrastructure to advance scientific discovery, engineering, and the knowledge economy. It will also be a central node for managing developers and maintainers of the OpenClaw platform.
Karthik's research spans a broad spectrum of computational science and engineering, including new modeling approaches for complex physical systems, numerical methods, algorithms and uncertainty quantification.
This is the first conversation Karthik’s had going deep on the institute. We talk about using AI to advance scientific research, two new discoveries announced yesterday, how universities work, how AI is impacting students and education, and his advice for young people.
Thank you to Numeral, Flex, and Amplitude for supporting this episode
Numeral: The end-to-end platform for sales tax and compliance https://www.numeral.com](https://www.numeral.com/
Flex: Sign-up for Flex Elite with code TURNER, get $1,000 https://form.typeform.com/to/Rx9rTjFz
Amplitude: AI analytics, all you have to do is ask https://www.amplitude.com
Timestamps:
(0:25) The Institute for Agentic Computing
(4:27) OpenClaw Foundation and Lobster Compute Company
(8:19) How Universities actually work
(12:33) ClawCon in Ann Arbor
(15:24) Two scientific discoveries made with ScienceClaw
(20:06) How AI is speeding up scientific discovery
(25:42) Supporting AI and OpenClaw development
(29:55) Why universities function like VC funds
(34:29) How Universities get money from the government
(40:55) Why some academics believe AI is a fad
(46:17) Biggest bottlenecks in AI today
(49:26) How AI will change the world
(53:10) Karthik's Code Red advice for students
(59:19) Separating learning and doing
(1:03:10) Ways COVID and AI impacted college students
(1:14:53) How the role of universities is changing
(1:23:21) Why college classes suffered from grade inflation
(1:26:05) How AI is actually impacting the job market
(1:32:49) Karthik’s advice for students
(1:39:16) Winning two NCAA basketball national championships
(1:43:04) Almost dying in the Grand Teton National Park
Referenced
More on Karthik: https://aero.engin.umich.edu/people/duraisamy-karthik/
Institute for Agentic Computing: https://record.umich.edu/articles/u-m-launches-institute-for-agentic-computing/
ClawCon Announcement:
OpenClaw: https://openclaw.ai/
ScienceClaw: http://scienceclaw.science/
MIT OpenCourseWare: https://ocw.mit.edu/
ASU iPhone video: https://www.youtube.com/watch?v=qqfk7-3iN-U
Follow Karthik
LinkedIn: https://www.linkedin.com/in/karthik-duraisamy-66705025
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/
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Nikhil Krishnan is the Founder of Out of Pocket, a media company that makes understanding healthcare more entertaining and accessible.
We spend 100 minutes talking about how the US healthcare system actually works, how World War II changed it forever, all the ways AI is seeing real adoption across the industry, and most common bad startup ideas in healthcare.
Thank you to Numeral, Flex, and Amplitude for supporting this episode
Numeral: The end-to-end platform for sales tax and compliance [https://www.numeral.com](https://www.numeral.com/)
Flex: Sign-up for Flex Elite with code TURNER, get $1,000 https://form.typeform.com/to/Rx9rTjFz
Amplitude: AI analytics, all you have to do is ask [https://www.amplitude.com](https://www.amplitude.com/)
Timestamps:
(1:23) How the US healthcare system works
(4:26) Why US healthcare is different from the rest of the world
(12:01) Why healthcare costs keep going up
(15:58) Core problem: is healthcare a marketplace or not?
(21:04) How money flows + Two-way price negotiation
(27:34) Why payments are seeing early AI adoption
(30:08) How AI could change healthcare delivery
(35:40) Doctor’s are trapped on a productivity hamster wheel
(39:28) How incentives shape healthcare delivery
(43:53) Healthcare is an implicit jobs program in the US
(48:45) Areas AI is overhyped, worst healthcare startups
(55:30) Consumerization of healthcare
(1:01:58) Rise of Peptides, understanding risks and downsides
(1:09:35) Why all medical software is so bad
(1:11:58) How to do enterprise sales in healthcare
(1:14:51) The battle forming between Scribes, Search, and EMRs
(1:18:33) Why we need more physician independence
(1:26:51) Starting Out of Pocket in February of 2020
(1:2912) Write to meet your audience
(1:37:54) Using AI as a content creator
(1:42:13) How to get started writing on the internet
Referenced
Out of Pocket: https://www.outofpocket.health/
Doctronic: https://www.doctronic.ai/
Follow Nikhil
Twitter: https://x.com/nikillinit
LinkedIn: https://www.linkedin.com/in/thinkboi/
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/
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Sophia Amoruso is the Founder of Nasty Gal and Trust Fund, an early stage venture capital firm.
We talk through her journey of starting Nasty Gal as an Ebay store in 2006 to sell vintage clothing, bootstrapping it to $28 million in revenue, raising $50 million, scaling it to $120 million and a massive team, turning down a $400 million acquisition offer, and ultimately declaring bankruptcy.
She takes us inside what it was like to fail so publicly, what she’d do differently next time around, lessons from building the brand, and why she started her VC firm Trust Fund to back the next generation of founders building consequential companies.
Thank you to Numeral, Flex, Amplitude, and Merge for supporting this episode
Numeral: The end-to-end platform for sales tax and compliance https://www.numeral.com
Flex: Sign-up for Flex Elite with code TURNER, get $1,000 https://form.typeform.com/to/Rx9rTjFz
Amplitude: AI analytics, all you have to do is ask https://www.amplitude.com
Merge: Every modal. One API. Total control. Check out Merge Gateway https://www.merge.dev/gateway
Timestamps:
(0:59) Selling vintage on Ebay while working at an art school
(04:31) Lessons in marketing and perceived value
(12:38) Knowing when to make your first hire
(18:31) Borrowing from others to build a unique brand
(25:17) Growing to $120m revenue in seven years
(27:24) Sharing the pitch deck that raised $50m
(30:17) Mistakes scaling to 100’s of employees too fast
(34:48) Downsides of raising at too high of a valuation
(39:56) Why being a CEO is fun
(42:57) Declaring bankruptcy
(50:38) How it feels to fail publicly
(54:41) Writing a book, Netflix series, starting the Girlboss movement
(59:13) How to create a new brand in 2026
(1:05:34) Starting Trust Fund to invest and help founders
(1:13:45) Raising $5m from a poker game
(1:18:47) Sophia asks for Turner’s LP pitch
(1:26:53) Traits of the best founders
Trust Fund: https://www.trustfund.vc/
Pitch Trust Fund: https://www.trustfund.vc/pitches
Nasty Gal: https://www.nastygal.com/
Follow Sophia
Instagram: https://www.instagram.com/sophiaamoruso
Twitter: https://x.com/sophiaamoruso
LinkedIn: https://www.linkedin.com/in/sophiaamoruso
Website: https://www.sophiaamoruso.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/
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Nikhil Basu Trivedi and Mike Smith are the Co-founders of Footwork where they invest up to $15 million in Seed and Series A rounds. This is the first time they've ever sat down to record a conversation together on video.
We talk about starting the firm in 2020, their secret sauce for working with founders, lessons investing in Canva’s Seed round, scaling Stitch Fix from $0 to $1B revenue in five years with $17m in capital, why AI will enable a new wave of entrepreneurship, and how public company boards are discussing AI today.
Thank you to Tony Staehelin, Andrew Riesen, and Hunter Walk for helping brainstorming topics for the conversation.
Thank you to Flex for supporting this episode.
Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz
Timestamps:
(0:24) Starting Footwork from a tweet in 2021
(3:11) Difference between startup and public company boards
(4:52) 20-40% of board meetings are now about AI
(7:48) How Footwork’s investing in AI today
(10:37) AI will enable millions of new entrepreneurs
(15:04) 37 questions to ask when starting a VC firm
(17:40) Importance of differences
(23:08) The pace of VC is faster than operating
(26:26) Footwork’s secret sauce (2x board seats, 1-pager)
(31:59) Investors should talk to and help employees
(37:05) Building an equal-carry partnership
(39:33) How Footwork makes decisions
(43:21) Navigating short-termism and politics in VC firms
(51:18) “You’re only as good as your next investment”
(53:30) Characteristics of great founders
(58:13) Canva’s Seed pitch in 2014
(1:02:54) Joining Stitch Fix as 4th employee
(1:06:40) Scaling Stitch Fix $0 to $1B revenue in five years with $17m in capital
(1:16:48) Raising from Bill Gurley after a failed Series A
(1:19:40) Footwork’s office near YC
(1:22:10) Opportunities in consumer health
(1:25:20) Using flash mobs to win deals
(1:26:15) Dad life
Referenced
Footwork: https://www.footwork.vc/
Anything: https://www.anything.com/
Table22: https://www.table22.com/
Canva: https://www.canva.com/
Stitch Fix: https://www.stitchfix.com/
Honeydew: https://www.honeydew.com/
Follow Mike
Twitter: https://x.com/msmith492
LinkedIn: https://www.linkedin.com/in/michaelcsmith1
Follow Nikhil
Twitter: https://x.com/nbt
LinkedIn: https://www.linkedin.com/in/nikhilbt
Substack: https://nbt.substack.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/
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Chris Hladczuk is the Co-founder and CEO of Hanover Park, the AI-native fund administrator, vertically integrating fund administration, portfolio management, and LP experience for finance and investment teams.
Chris is the 2nd ever returning guest of the show, and is fresh off announcing Hanover’s $27m Series A. We go inside the round, their explosive growth, why they built their own general ledger from scratch, and how that enabled them to build incredible AI products for investment firms that touch over $100 trillion in assets.
Thanks to Sahil Bloom, and Chad + Pratyush at Susa for help brainstorming topics for this conversation.
Thank you to Numeral and Flex for supporting this episode.
Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com
Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz
Timestamps:
(0:37) Financial infrastructure for investment firms
(1:35) Hanover Park’s $27m Series A
(5:30) AI-enabled services businesses
(9:07) Productizing the service layer
(11:30) Helping CFO’s and investors use AI
(13:46) Building a general ledger from scratch
(18:03) Compete against companies with IT departments
(19:55) Hiring in an unsexy industry
(21:30) Live in constant paranoia of your customers
(25:19) Gongs, music in the office, blizzard commutes
(28:54) Friday night hackathons
(30:54) Automating onboarding and manual admin work
(35:05) Real-time visibility on all data
(38:07) Always get on the plane
(40:36) Turning customers into raving fans
(43:45) Using polite persistence in sales
(47:36) How to master founder-led content
(51:29) 99% of advice is wrong in AI era
(54:21) Importance of one-way vs two-way doors
(56:11) Growing from VC into PE and Private Credit
(1:00:36) When to turn down new customers
(1:02:22) Becoming a customers most important vendor
(1:04:00) Chris’ personal AI stack
(1:07:41) Hanover Park’s MCP
Referenced
Try Hanover Park: https://www.hanoverpark.com/
Careers at Hanover Park: https://jobs.ashbyhq.com/hanover-park
First episode with Chris: https://www.youtube.com/watch?v=7lomqcrFNv8
Artie: https://www.artie.com/
Episode with Jacqueline @ Artie: https://www.youtube.com/watch?v=6fd1YKsBaq0
Granola: https://www.granola.ai/
Claude Cowork: https://claude.com/product/cowork
HubSpot: https://www.hubspot.com/
Attio: https://attio.com/
Monaco: https://www.monaco.com/
Follow Chris
Twitter: https://x.com/chrishlad
LinkedIn: https://www.linkedin.com/in/chris-hladczuk-b09204153
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/
-
Scott Stevenson is the Co-founder and CEO of Spellbook.
Spellbook is an AI copilot for contract review and drafting, essentially “Cursor for lawyers.” They have 4,000 customers in 80 countries, and to my knowledge is the fastest growing AI company in Canada, and the largest company in the world built on a Microsoft Word plugin.
Scott has been building in legal AI longer than almost anyone. We talk about why legal software was essentially untouched before LLM’s, why the market is so hot right now, if it’s sustainable, and how Spellbook navigates product differentiation compared to horizontal AI products like ChatGPT.
We talk about why fine-tuning your own models was one of the biggest mistakes early AI companies made, how to build a network effect as a vertical AI product, and Spellbook’s philosophy of “Don’t sharpen your axe when the chainsaw is coming out tomorrow”.
Spellbook spent a few years finding PMF before really taking off in 2022, and Scott shares their playbook for launching over 100 product experiments in three years, how to know when to lean in, and what it’s been like scaling Spellbook post-PMF.
Thank you to Numeral and Flex for supporting this episode.
Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com
Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz
Timestamps:
(0:30) Spellbook: “Cursor for Contracts”
(3:08) Building the world’s largest Microsoft Word plugin
(14:06) Why legal software was untouched before LLMs
(18:32) $30 trillion moves through contracts annually
(20:51) Why ChatGPT won’t replace vertical tools
(25:15) Fine-tuning was the biggest mistake in AI
(30:00) Differences between pro and amateur gamers
(37:38) Top-down vs. bottoms-up in legal AI
(42:27) The long-tail of legal AI software
(47:24) Building for models that don’t exist yet
(51:20) Skating where the puck is going
(1:01:35) The legal bill that cost 50% of his bank account
(1:09:33) Testing 100 landing pages in 3 years
(1:14:06) The moment Spellbook hit PMF
(1:19:17) Building new brands for each product experiment
(1:23:10) Raising a Series B with a tweet
(1:27:41) What Scott learned from Keith Rabois
(1:31:16) Scott's favorite new AI tool
Referenced
Spellbook: https://www.spellbook.legal/
Careers at Spellbook: https://www.spellbook.legal/careers
Playing to Win by David Sirlin: https://www.amazon.com/Playing-Win-becoming-David-Sirlin/dp/1413498817
Find the Fast Moving Water by NFX: https://www.nfx.com/post/find-the-fast-moving-water
Spellbook’s case study with Replit: https://replit.com/customers/spellbook
Twin: https://twin.so/
Follow Scott
Twitter: https://x.com/scottastevenson
LinkedIn: https://www.linkedin.com/in/scottas
Blog: https://blog.scottstevenson.net/
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/
-
Chetan Puttagunta is a General Partner at Benchmark.
We talk about investing in Manus, the AI company that went from zero to $100M ARR in eight months and was recently acquired by Meta.
We also talk through the full history of application software, from mainframes to client-server, to the internet to cloud, why each wave reduced the barrier to entry and created an explosion in the number of new software, why legacy SaaS companies are making the same mistake on-prem vendors made at the dawn of the cloud, why software companies should be making big AI acquisitions, and how public market investors are begging private AI companies to go public.
We also talk about what Benchmark actually looks for in founders, how they make decisions, and why his last two investments were consumer AI and crypto.
Thanks to Sam Ross and Everett Randle for helping brainstorm topics for this conversation.
Thanks you to Numeral and Flex for supporting this episode.
Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com
Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz
Timestamps:
(0:08) Inside the $2.5B Manus acquisition
(6:24) Manus' three main use cases
(11:08) Taking heat on Twitter
(15:10) Starting to tweet about software in 2018
(22:50) The history of application software
(29:15) Benchmark’s 25x Fund 7
(31:33) SaaS incumbents got too dominant by 2020
(31:48) Going all-in on AI software in 2022
(39:31) Benchmark didn’t invest in the big AI labs
(40:48) How cloud companies beat on-prem competitors
(44:33) Why AI companies will beat legacy cloud competitors
(50:04) Software incumbents should make big AI acquisitions
(57:35) Why incumbents have not bought more AI companies
(1:04:43) Public markets are starving for AI companies
(1:10:14) Inside Benchmark’s fund strategy
(1:14:14) Benchmark’s history of non-traditional VC rounds
(1:17:56) Is the 20% ownership model outdated?
(1:19:20) Chetan’s rebirth as a consumer investor
(1:22:39) What Benchmark looks for in founders
(1:25:01) AI coding and gross margins
Referenced
Benchmark: https://benchmark.com/
Eric Vishria’s podcast episode: https://www.youtube.com/watch?v=I-5IsqFgrZM
Workday S-1: https://www.sec.gov/Archives/edgar/data/1327811/000119312512375787/d385110ds1.htm
Innovator's Dilemma: https://www.amazon.com/Innovators-Dilemma-Revolutionary-Business-Essentials/dp/0060521996
Try FOMO: https://apps.apple.com/us/app/fomo-never-miss-out/id6741115427
Follow Chetan
Twitter: https://x.com/chetanp
LinkedIn: https://www.linkedin.com/in/chetanputtagunta
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/
-
Jake Stauch is the Co-founder and CEO of Serval. Serval automates IT with AI.
We talk taking on incumbents with an AI-native product, why IT departments haven’t had much automation historically, the 12+ month journey of landing their first customer, and how teams can increase talent density as they scale.
Try Numeral, the end-to-end platform for sales tax and compliance: [https://www.numeral.com](https://www.numeral.xn--com-xw0a/)
Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz
Timestamps:
(0:14) AI-native employee support
(5:15) How an early work trial almost ended the entire company
(9:05) Why IT hasn’t had much automation
(13:09) Vibe coding for IT professionals
(15:31) Competing against publicly traded incumbents
(23:32) Having less than three months of runway for seven years building his first hardware consumer health startup
(33:15) Lessons from five years at Verkada
(39:11) The single question that led birthed the idea for Serval
(44:19) Navigating 12+ months of zero revenue
(52:05) Knowing when not to pivot
(55:15) Finally landing the first three customers
(58:07) Getting pre-empted for a Series A
(1:01:04) Getting a Series B term sheet the next day
(1:05:54) How to structure design partnerships that convert
(1:08:48) Building a mirror instead of system of record
(1:13:49) Make the implementation part of the product
(1:15:24) How to increase talent density as you scale
(1:21:32) Why every new hire should help you recruit
Referenced
Try Serval: https://www.serval.com/
Careers at Serval: https://www.serval.com/careers
Episode with Filip @ Verkada: https://www.youtube.com/watch?v=fXI3GdicIHw
Follow Jake
Twitter: https://x.com/jakeserval
LinkedIn: https://www.linkedin.com/in/jakestauch
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/
-
Gary Tan is the President and CEO of Y Combinator.
YC is the startup accelerator behind companies like Airbnb, Stripe, Coinbase, Reddit, Twitch, and thousands more. According to Garry, they’ve invested in 20% of all startups worth $5B or more started since 2012.
Gary has lived every side of the YC ecosystem. He went through YC as a founder, later became a partner, started Initialized Capital where he backed companies like Coinbase and Instacart, and then returned to lead YC.
We walk through the different “eras” of YC, from the early Paul Graham and Jessica Livingston days in Cambridge, to scaling in San Francisco, to today’s push back toward in person community and what Gary calls “founder mode” for the organization itself.
We also talk about why the Bay Area still matters so much for startups, what’s happening with California taxes and policy, and why Gary has gotten more involved in local politics to keep it the best place for founders to build companies.
Then we go deep on the parts of startups people don’t talk about enough. Co-founder conflict, rage quitting, therapy and coaching, and why companies inevitably take on the personality and emotional patterns of their founders.
We also cover what YC looks for in applications, how the 13 week batch is structured, how Demo Day really works, how to choose the right investors, and what Gary thinks the next phase of YC looks like, including helping founders even after Series A.
At the end, Gary shares his personal AI workflow, including meta prompting, comparing outputs across models, and the tools he uses every day to think and build faster.
Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com
Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz
Timestamps:
(0:05) Moving from Winnipeg to California as a kid
(1:35) How YC interviews work
(2:55) The first batch in 2005
(6:46) Why YC moved from Boston to SF
(8:17) California’s Billionaire Tax
(11:00) Tech should care about public policies
(17:01) Going direct to your audience
(20:28) The 2nd Era of YC
(24:01) Rage quitting Palantir, learning to understand himself
(32:41) Co-founder conflict kills most startups
(35:15) Joining YC as a group partner
(37:22) Initialized Fund 1 (55x DPI)
(39:44) Why Garry went back to lead YC
(42:44) YC funds 20% of all $5B+ companies
(44:30) Lessons from Brian Chesky
(48:01) Garry’s thoughts on YC rejection
(51:41) How to get into YC
(58:03) What it’s like inside a 13-week YC batch
(1:02:23) 20% of YC is hard tech
(1:05:55) YC's 3rd era: founder mode, re-batching
(1:07:56) Escaping the matrix
(1:11:26) Garry's personal AI stack
(1:20:25) Tech optimism
Referenced
Y Combinator: https://www.ycombinator.com/
Initialized Capital: https://initialized.com/
Torch: https://torch.io/
Perplexity: https://www.perplexity.ai/
Anthropic: https://www.anthropic.com/
OpenAI: https://openai.com/
Airbnb: https://www.airbnb.com/
Kyle Vogt on his new startup: https://www.youtube.com/watch?v=XQoFbvyWEy8
Follow Aaron Levie on X: https://x.com/levie
Follow Gary
Twitter: https://x.com/garytan
LinkedIn: https://www.linkedin.com/in/garytan/
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/
-
Miranda Nover is the Co-founder and CEO of Fort Health. Fort builds wearables that automatically track strength training for people who care about longevity.
This is a new format I’m experimenting with. It’s the first time I’ve had a Banana portfolio company founder on the show while they’re still at the pre-seed stage. When I surveyed my subscribers a few weeks ago, you were most interested in more early stage VC-backed founders, and I’d love your feedback on what you think of this.
Miranda is still very much working through the idea maze and iterating on the Fort product. We talk about the megatrends driving consumer health, why she’s building a company that helps people get stronger, and everything she’s learned getting a hardware company off the ground.
She’s also in the middle of the current YC batch, and gives an inside look at what it’s been like and if she’d recommend it to other founders.
Thank you to Numeral and Flex for supporting this episode.
Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com
Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz
Timestamps:
(3:37) Importance of strength training
(6:34) Benefits of being strong
(10:37) Evolution of Fort’s hardware
(15:58) Automating workout tracking
(19:29) Two types of strength trainers
(25:30) Building the strength company
(27:26) How healthcare is consumerizing
(40:43) Lessons building batteries at Tesla
(44:56) Hardest parts about building a hardware startup
(51:01) Adventures in vibe coding
(57:54) How to use Twitter as a founder
(1:02:09) The launch video industrial complex
(1:08:03) What it’s like doing YC
(1:10:19) Selling crayons in 3rd grade, Lemonade stands
(1:14:41) Miranda’s best vintage finds
(1:16:44) How Turner evolved as a VC
(1:22:22) Turner’s early social media PMF
(1:28:53) Inventing shitposting
Referenced
Try Fort: https://www.fort.cx/
Follow Miranda
Twitter: https://x.com/mirandanover
LinkedIn: https://www.linkedin.com/in/mirandanover
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/
-
Dug Song and Jon Oberheide are the co-founders of Duo Security.
If you’ve never heard of Duo, it might be one of the most underrated software stories of all-time.
Starting in 2010, they burned only $14 million to hit $100m in ARR, were acquired by Cisco for $2.35 billion in 2018, and now rumored to be doing over $1 billion in ARR inside Cisco 16 years later.
We talk about how they built one of the most capital efficient SaaS companies ever from Ann Arbor, Michigan, and how their focus on the customer and company culture helped them win in a crowded cybersecurity market.
We talk growing up in the early hacking culture of the 90s, why most security tools are painful to use, sizing their market, solving for non-consumption of a product, and how Duo flipped the model by designing for end users instead of security teams.
We talk about staying in Michigan instead of moving to Silicon Valley, and why staying out of the tech bubble helped them execute.
We break down the mechanics of scaling from zero to $100 million in ARR, everything they learned integrating with Cisco, and why more founders should build outside of San Francisco.
A quick thank you ex-Duo employees Zack Urlocker, Ash Devata, and Katie Kilroy for their help brainstorming topics for the conversation.
Try Numeral, the end-to-end platform for sales tax and compliance: [https://www.numeral.com](https://www.numeral.com/)
Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz
Timestamps:
(4:49) Meeting from Dug’s Wi-Fi honeypot
(7:33) 90’s hacking culture and cybersecurity’s wild west
(14:49) How the internet was born in Ann Arbor
(18:58) Staying in Michigan instead of moving to Silicon Valley
(31:20) Philosophy on leadership and team building
(39:48) What makes a good engineering leader
(44:01) Starting Duo to make security easier
(45:22) Why most security products suck
(48:36) How fixing account takeover became a $1B ARR company
(59:10) TAM, competition, fixing the non-consumption of security
(1:04:04) Being a radical advocate for the customer
(1:08:35) Duo’s pizza sales play
(1:12:45) Branding lessons from Anthropic, Tesla, Cliff Bar
(1:17:47) When to say no to customers
(1:21:27) Importance of culture when scaling
(1:27:56) Duo’s role in uncovering the SolarWinds breach
(1:31:29) Scaling to $100M ARR on $14M burned
(1:39:30) Inside the $2.35B Cisco acquisition
(1:44:02) What big companies get wrong about customers
(1:51:53) Building Michigan’s startup ecosystem
Referenced
Duo Security: [https://duo.com](https://duo.com/)
Cisco: [https://www.cisco.com](https://www.cisco.com/)
University of Michigan: [https://umich.edu](https://umich.edu/)
Follow Dug
Twitter: https://x.com/dugsong
LinkedIn: https://www.linkedin.com/in/dugsong
Follow Jon
Twitter: https://x.com/jonoberheide
LinkedIn: https://www.linkedin.com/in/jono
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/
-
Jacqueline Cheong is the Co-founder and CEO of Artie.
Artie moves data across your systems in real-time, and we talk about why that’s so important in the age of AI.
It’s a lot harder than you’d think, as less than 5% of real-time data streaming projects are successful.
I talked to a dozen people to prepare for this conversation, including Jared Friedman who worked with Jacqueline during YC, her sales coach Ras, and numerous Artie employees like A-nee-rud, Ryan, Sarah, Shangbing and Jacqueline’s co-founder Robin.
We talk through how Robin built real-time data streaming at OpenDoor and Zendesk before they started Artie, and Jacqueline shares the sales playbook she learned going from hedge fund analyst to software CEO, including asking customers for their hardest problem and then solving it with the product.
Artie just announced a $12 million Series A a few weeks before we published this episode. We talk about how they landed all of their early enterprise customers through cold outbound, how they structure and automate their prospecting with AI so they have no BDRs, and why they’re seeing customers switch to Artie even after building their own multi-million dollar real-time streaming projects in-house.
I also asked Jacqueline what it’s like working with Standard Capital. They’re a new fund started by a group of YC partners, and it was fascinating to hear about the things they’ve borrowed from YC when investing at the Series A stage.
Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com
Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz
Timestamps:
(4:08) Artie: Real-time data streaming
(5:13) Why moving data is so hard
(9:14) Evolution of data warehouses
(12:47) AI needs real-time data
(18:44) Build vs buy in data streaming
(22:51) How to build in a crowded market
(26:26) Early focus on a specific hard problem
(30:33) Acquiring enterprise customers from cold emails
(32:51) Onboarding their first customer with no UI
(35:46) Solving compliance and implementation
(38:50) How to automate internal engineering, marketing, and ops
(44:01) Building an AI-powered GTM pipeline and motion
(46:52) Add your customers on iMessage, Slack, Teams
(53:00) Starting Artie to solve their own problem
(59:25) Discovering YC through a friend
(1:02:20) Everything Jacqueline learned about sales
(1:06:29) How to improve your sales discovery calls
(1:10:08) Inside Artie’s $12m Series A
(1:16:44) What its like working with Standard Capital
(1:22:59) Jacqueline’s favorite book
Referenced
Try Artie: https://artie.com
Careers at Artie: https://www.artie.com/careers
Clay: https://www.clay.com
Podcast with Tommy @ Alloy: https://www.youtube.com/watch?v=e7i8Wxklu-Y
YCombinator: https://www.ycombinator.com
Standard Capital: https://www.standardcap.com
Founding Sales: https://www.foundingsales.com
The Score Takes Care of Itself: https://www.amazon.com/Score-Takes-Care-Itself-Philosophy/dp/1591843472
Follow Jacqueline
Twitter: https://x.com/JacquelineSYC19
LinkedIn: https://www.linkedin.com/in/jacqueline-cheong
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/
-
Nathan Benaich is the founder of Air Street Capital and author of the State of AI report. On its eighth year, the report is a year-long effort on the biggest things happening in AI, across research, industry, politics, and safety.
This episode covers the biggest takeaways from the latest report, like the rise in reasoning, the surge in China’s open source models, where AI is working in practice, the rise of sovereign AI, where he thinks value will actually accrue over the long-term, if we’re in an AI bubble, and how he’s investing in AI today at Air Street.
Thanks to Nico at Adjacent and Dan at Michigan for helping brainstorm topics for Nathan.
Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com
Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz
Timestamps:
(3:39) State of AI 2025
(6:22) Takeaway #1: Reasoning & tool calling
(13:01) Takeaway #2: Rise of Chinese open source
(15:25) Open vs closed source models
(26:46) Takeaway #3: AI revenue is real
(27:51) Takeaway #4: Sovereign AI
(36:44) Are we in an AI bubble?
(59:23) Starting Air Street Capital
(1:05:18) Raising Fund 1
(1:16:20) Air Street portfolio strategy
(1:25:15) When and who Nathan decides to invest
(1:35:04) How important are AI benchmarks?
(1:39:31) When to train your own models
(1:45:56) Rise of European defense tech
(2:01:43) Nathan’s personal AI stack
(2:07:32) Is niching down too risky?
(2:16:12) Nadal vs Federer
Referenced
State of AI Report: https://www.stateof.ai
The Thinking Game Documentary: https://www.youtube.com/watch?v=d95J8yzvjbQ
V7: https://www.v7labs.com
Follow NathanTwitter: https://x.com/nathanbenaichLinkedIn: https://www.linkedin.com/in/nathanbenaich
Follow TurnerTwitter: 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/
-
Marcelo Lebre is the Co-founder and President of Remote, the payroll and international employment company.
Remote is one of today's most underrated software companies. We get into why payroll is such a hard problem, why most of the industry still runs on spreadsheets, the edge cases of software meeting government, and a diagnosis of Europe’s regulation problem.
We also talk through the journey trying 8 different startup ideas before Remote, how COVID changed the business overnight, and what he’s learned about building culture and running remote teams.
Thanks to Gillian O’Brien, Villi Iltchev, Andreas Klinger, Masha Bucher, and Marcelo’s co-founder Job for helping brainstorm topics for this.
Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com
Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz
Timestamps:
(3:22) Gaming with kids
(6:05) Hundreds of millions in revenue in the most boring market
(8:22) Payroll corporate spies
(14:54) Why payroll tax is such a hard problem
(19:46) Why tax is even more complicated outside the US
(23:08) Legacy payroll still runs on manual spreadsheets
(29:14) Remote’s unfair advantage in AI
(31:40) Building the global payroll API that didn’t exist
(38:06) Meeting his co-founder on a double date
(42:04) Seven years of failed products before Remote
(49:25) Launching Remote in 2019
(52:39) Each year felt like a new apocalypse
(59:25) Distributed teams must master async, document everything
(1:02:42) Culture is what you tolerate
(1:13:05) Europe's regulation problem and why it can't innovate
(1:21:18) Why fundraising is so hard in Europe
(1:28:23) Deleting spreadsheets to force automation
(1:40:25) Burnout, health, fixing the system instead of grinding harder
(1:47:57) Writing honestly about the hard parts of building companies
Referenced
Try Remote: https://remote.com/
Careers at Remote: https://remote.com/careers
Remote Handbook: https://remotecom.notion.site/a3439c6ccaac4d5f8c7515c357345c11?v=8bb7f9be662f45da87ef4ab14a42be37
The Toyota Way: https://www.amazon.com/Toyota-Way-Management-Principles-Manufacturer/dp/0071392319
The Book of Five Rings: https://www.amazon.com/Book-Five-Rings-Miyamoto-Musashi/dp/1590309847
Follow Marcelo
Twitter: https://x.com/marcelolebre
LinkedIn: https://www.linkedin.com/in/marcelolebre
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/
- Montre plus
