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Copyright: © Turner Novak
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
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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(1:17:56) Is the 20% ownership model outdated?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/)
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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
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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
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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
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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
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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/)
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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.
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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
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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.
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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
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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
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Kevin Hartz, Co-founder of A*, Eventbrite, Xoom, and Sauron.
Kevin has been building and investing in technology companies for 30 years, and we talk about how the industry’s evolved, why he calls AI the Mother of All Bubbles, why we’re still early, and lessons today’s breakout AI companies can learn from those that survived the Dot Com Crash.
Kevin is a big proponent of backing young founders. A significant percentage of his latest fund at A* is invested in teenagers, and he shares how he identifies outlier talent so early, from Seed investments in Airbnb, PayPal, and Pinterest, to many of today’s hottest AI companies.
He also shares the insane story of investing 100% of the proceeds from his first startup into PayPal’s Seed round, how PayPal’s early fraud systems inspired Palantir, what he learned from the PayPal Mafia, from Peter Thiel, and what makes Founders Fund special.
We also talk about how he and his wife recently had two babies, five months apart, using genome screening and surrogates.
Thanks to Ramtin Naimi, Navya Gudimetla, and Bennett Siegel for helping brainstorm topics for the conversation.
Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com
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Timestamps:
(4:25) Power shift from VC’s to founders since the 90’s
(9:08) AI is the mother of all bubbles
(12:40) Why AI is still underhyped
(14:10) What Kevin and A* are investing in today
(16:02) Investing 100% of his first startups proceeds in PayPal’s Seed round
(21:21) What made the PayPal Mafia special
(23:37) Parallels between the 90’s and today
(26:40) What makes Founders Fund special
(35:07) How Palantir evolved from PayPal’s fraud models
(39:06) Building Xoom on the PayPal API
(43:38) Lessons between Kevin’s 1st and 2nd startups
(46:52) Starting Eventbrite off early PayPal API app
(51:51) Eventbrite’s hidden TAM challenge
(53:49) Selling Eventbrite to Bending Spoons
(54:59) Investing 20% of A* in teenage founders
(1:02:33) Incubating Sauron, the home security company
(1:08:44) Making breakfast for our kids
(1:13:33) Having kids with genome screening and surrogates
(1:20:31) Collecting art, how to get started
Referenced
https://www.a-star.co/
https://www.eventbrite.com/
https://www.xoom.com/
https://www.sauron.systems/
https://www.orchidhealth.com/
Setting the Table by Danny Meyer: https://www.amazon.com/Setting-Table-Transforming-Hospitality-Business/dp/0060742763
20% of fund in teenage founders: https://techcrunch.com/2025/10/18/this-top-vc-bet-close-to-20-of-his-fund-on-teenagers-heres-why/
https://nypost.com/2025/12/14/us-news/xu-bo-chinese-billionaire-reportedly-sires-more-than-100-kids/
Follow Kevin
Twitter: https://x.com/kevinhartz
LinkedIn: https://www.linkedin.com/in/hartz
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
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Jason Calacanis is the host of the All-In Podcast, This Week in Startups, co-founder of the Launch Accelerator, and the “3rd or 4th investor in uber”.
We go inside the origins of All-In, how they decide what to talk about each week, and if Jason thinks it helped swing the election.
We also talk lesson from starting 7 media companies over the past three decades, what he's learned from studying the world's best interviewers, joining Sequoia’s first scout program, his investing strategy at Launch, the story of being the “3rd or 4th investor in Uber", what people underestimate about Elon, and what it was like inside the Twitter buyout in 2022.
Thank you to Austin Petersmith for helping brainstorming topics for the conversation.
Thanks to Numeral for supporting this episode. It’s the end-to-end platform for sales tax and compliance. Try it here: https://www.numeral.com
Timestamps:
(3:34) Interviewing lessons from Oprah, Charlie Rose
(6:48) How to ask good questions
(12:20) Jason’s favorite upcoming podcasters
(17:57) Starting 7 media companies
(22:50) How he'd start a new media company today
(27:56) In-person experiences, “Bang Bang” in Japan
(32:44) Vinyl bars, smartphones, mental health
(38:41) Origin of the All-In Podcast
(42:58) All-In’s influence on the 2024 Election
(46:58) Why All-In got so political
(52:35) Media lessons from Trump
(55:01) Joining Sequoia’s very first scout program
(57:55) Jason’s VC investing strategy
(1:03:55) How Launch competes with other accelerators
(1:08:46) Fundraising is a numbers game
(1:13:06) Investing in Uber and Robinhood Seed rounds
(1:18:31) Origin of “3rd or 4th investor in Uber” meme
(1:20:57) How Jason got the first Model S
(1:26:19) What people underestimate about Elon
(1:27:37) Inside the Twitter takeover
(1:31:44) Career advice for young people
(1:35:22) Jason’s experience taking GLP-1’s
(1:40:05) How All-in picks topics each week
Referenced
Howie: https://howie.com/
All-In Podcast: https://allin.com/
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Adam Friedland Show: https://www.youtube.com/c/TheAdamFriedlandShow
The Insider (Movie): https://www.imdb.com/title/tt0140352/
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