Stay ConnectedExploring the world’s greatest startup stories.
Get a behind the scenes look into the founding stories of your favorite companies. Learn how the industries they operate in actually work, and learn playbooks and tactics you can use to launch and scale your own business.
Copyright: © Turner Novak
Chris Frantz is the Co-founder and CEO of Loops, the email platform for software companies.
We get into why sending emails is still a big problem, his hilariously simple framework for building products, getting in to YC with a last minute application, and why they skipped raising a Series A.
We also talk through Chris decade of working in marketing, like when to lean into PLG vs Sales vs hype led growth, early stunts they did to get their first users, why they do no marketing now, and why Loops’ customer support team is all engineers.
Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeel
Try Hanover Park - the modern, AI-native fund admin https://www.hanoverpark.com/Turner
Timestamps:
(4:37) Email for software companies
(8:28) Why email is a big deal
(14:05) The future of email
(17:00) Product vs Sales vs Hype led growth
(24:33) Coming up with the idea for Loops
(29:36) Building one of the first GPT wrappers in 2020
(34:34) Lessons selling his first company
(37:13) Doing their YC app in 10 minutes
(40:53) Avoiding VC’s who add value
(46:58) Skipping a Series A
(51:37) Building in stealth for 18 months
(53:21) Marketing stunts to get the first waitlist sign-ups
(58:44) Four step cadence of building Loops
(1:01:58) Personally onboarding every new customer
(1:04:03) Balancing 996 with family
(1:11:11) Cleaning wasp nests with a shop vac
Referenced
Loops: https://loops.so
Careers at Loops: https://loops.so/careers
Curiosity: https://curiositystream.com
Snazzy AI / Unbounce: https://unbounce.com/product/smart-copy
Atlas customer support: https://atlas.so
Follow Chris
Twitter: https://x.com/frantzfries
LinkedIn: https://www.linkedin.com/in/ctfrantz
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/
Dan Gray is the Head of Insights at Equidam.
If you’re a tech and investing nerd like us, you’ll love this conversation. We cover everything Dan’s learned reading dozens of academic research papers on startups and venture capital, debunking many popular narratives of the industry.
We talk about the dangers of pre-mature startup scaling, the importance of origination stage investing, the concept of startup catering and why so many startups look the same, and the role of mega funds play in the ecosystem.
We also discuss what the data says about concentration vs diversification, what VC’s get wrong about pattern matching, and why pivoting is more valuable than you think
Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeel
Try Harmonic - The startup discovery engine https://harmonic.ai/turner
Timestamps:
(6:43) What’s the required rate of return in VC?
(9:29) Venture capital needs new definitions
(16:10) QSBS
(18:23) Are we in an AI bubble?
(24:07) Re-branding early and late stage venture
(28:25) We need more origination stage capital
(40:05) Survivorship bias in emerging manager outperformance
(42:57) Incentives driving larger fund sizes
(48:10) Raising overvalued rounds re-risks a startup
(52:08) Startup catering: why all startups look alike
(58:42) Are VC mega funds still an experiment?
(1:08:06) Late stage VC is competing with PE
(1:13:42) a16z’s Fund 1 strategy
(1:18:18) How diversified should VC funds be?
(1:25:06) Performance of Generalist vs Specialist firms
(1:30:35) How to value a startup
(1:40:58) Why VC firm location correlates to returns, but startup location does not
(1:44:05) Founder background doesn’t predict success
(1:48:27) Startups with one pivot are most successful
(1:50:24) Premature scaling kills 70% of startups
(1:54:47) Does mega fund model work for origination investing?
(1:56:15) Value of Twitter and writing online
Referenced Research Papers
Venture Predation: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4437360
Process Alpha: https://angelspan.com/process-alpha-how-to-construct-and-manage-optimized-venture-portfolios-joe-milam-journal-of-portfolio-management-august-2022/
The Sunk Cost Fallacy in VC: https://www.sciencedirect.com/science/article/pii/S0929119924000518
Predictably Bad Investments in VC: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4135861
Startup Catering to Venture Capitalists: https://afajof.org/management/viewp.php?n=58968
Premature Scaling: https://innovationfootprints.com/wp-content/uploads/2015/07/startup-genome-report-extra-on-premature-scaling.pdf
Referenced Books
The Otherland Tetrology: https://www.goodreads.com/series/43762-otherland
Permutation City: https://www.goodreads.com/book/show/156784.Permutation_City?from_search=true&from_srp=true&qid=lf7FuUR9se&rank=1
Necromancer: https://www.goodreads.com/book/show/6088007-neuromancer?ref=nav_sb_ss_1_29
Other Referenced Items
QSBS changes: https://www.dwt.com/blogs/startup-law-blog/2025/07/qsbs-big-beautiful-bill-tax-code-upgrades
Mega funds and the great re-risking: https://nextview.vc/blog/megafunds-and-the-great-re-risking/
Rex Woodbury’s post on hot companies: https://www.digitalnative.tech/p/the-taxi-cab-theory-of-venture-capital
The VC Performance Paradox: https://www.linkedin.com/pulse/performance-paradox-venture-capital-dan-gray-2fqre
Prior episodes mentioned
Dan Feder: https://youtu.be/_Ou6D9PLSBI
Michael Dempsey: https://youtu.be/UzSbG6DL8CM
Solugen: https://youtu.be/ofkNiB2nI3Q
Follow Dan
Twitter: https://x.com/credistick
Blog: https://credistick.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/
Dan Feder is a Senior Managing Director of Investments at the University of Michigan’s $18 billion endowment.
Our two hour conversation talks through the past, present, and future of all things venture capital, and investing more broadly.
Dan lays out the case for why most institutional investors should change how they approach asset allocation, why risk and uncertainty are not the same, the importance of relevance and independent thinking, advice for fund managers raising from institutional LP’s, the trend of VC’s rolling up services businesses, and what he learned from beating Lance Armstrong in a race.
Thanks to Chris Douvos @ Ahoy Capital and Adam Kurkiewicz at WashU for their brainstorming topics for Dan!
Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeel
Try Hanover Park - the modern, AI-native fund admin https://www.hanoverpark.com/Turner
Timestamps:
(5:50) Beating Lance Armstrong in a race
(8:05) “The will to win is nothing without the will to prepare”
(10:39) Why investors need to re-think asset allocation
(22:31) Difference between risk and uncertainty
(29:26) How endowments work
(33:12) Endowment portfolio construction
(40:47) From law, to industrial buyouts, to venture
(49:13) Narrowing scope to increase returns
(54:54) Why career planning as an LP is hard
(58:24) VC in the 00’s
(1:08:18) Venture vs Adventure Capital
(1:15:16) VC’s rolling up legacy industries
(1:20:17) Importance of relevance
(1:26:25) Traits of the top investors
(1:28:25) Importance of trust in institutional LP fundraising
(1:32:54) Venture is the most competitive ass class
(1:35:37) Why venture firms do not persist over time
(1:38:27) How venture will change going forward
(1:43:37) The Newman Cycle
Referenced
A Sense of Where You Are by John McPhee: https://www.amazon.com/Sense-Where-You-Are-Princeton/dp/0374526893
Risk Uncertainty and Profit by Frank Knight: https://www.amazon.com/Risk-Uncertainty-Profit-Frank-Knight/dp/1614276390
Follow Dan
Twitter: https://x.com/federdan
LinkedIn: https://www.linkedin.com/in/danfeder
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/
Eoghan McCabe is the Co-founder and CEO of Intercom, building Fin.ai, the AI customer service company.
This was an extremely candid, two hour conversation going inside every detail of how Intercom was the first late stage software company to successfully re-architect itself to be AI-native.
Intercom just announced they’ve built their own customer service-focused AI models, and Eoghan explains why most software companies will have to do the same.
We also talk through the lessons he learned coming back to run Intercom in 2022 after stepping back in 2020, why many AI companies have strong negative gross margins despite the narrative, how Intercom designed AI’s first outcome-based pricing model, the challenges of buying AI software today, the importance of brand when building new products, and we get in the wayback machine, talking through the pain raising Intercom’s initial million dollar Seed round, and how venture capital has changed since then.
Thank you to Eoghan’s Co-founder Des Traynor for helping me brainstorm topics for the conversation.
Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeel
Timestamps:
(4:18) We’re at peak SaaS
(9:11) Inside early days of Intercom’s turnaround
(16:43) AI will beat humans at everything
(21:17) Making trade-offs building AI products
(24:25) Why Intercom trained their own AI models
(28:33) Lessons from returning as CEO
(34:19) Overcoming initial AI skepticism in 2022
(40:02) Creating AI’s first outcome-based pricing
(45:15) Intercom’s best-in-class gross margins
(49:25) Why its so hard to buy AI software today
(51:28) Unpacking AI’s negative gross margins
(58:12) Being perfectly positioned for AI
(1:09:47) Why AI products need their own brand
(1:16:13) Founder CEOs vs Manager CEOs in AI
(1:21:29) AI startup opportunities
(1:24:57) Lessons running a team in Dublin and SF
(1:28:25) How media has changed over time
(1:37:32) Raising Intercom’s first $1 million Seed round
(1:43:53) Why there are so many VC’s
(1:47:38) Advice for investors
Referenced
Intercom: https://www.intercom.com/
Fin: https://fin.ai/
Intercom Careers: https://www.intercom.com/careers
Eoghan’s website: https://eoghanmccabe.com
Intercom’s first pitch deck: https://www.slideshare.net/slideshow/intercompitchdeckpdf/253317574
Follow Eoghan
Twitter: https://x.com/eoghan
LinkedIn: https://www.linkedin.com/in/eoghanmccabe
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/
Albert Azout is the Co-founder and Managing Partner of Level Ventures, combining first-principles thinking with state-of-the-art data science to back and build top seed-stage firms and their breakout companies.
Venture investing is hard, and this conversation covers all their research unpacking exactly how to generate alpha.
We also talk about how Level picks and backs emerging venture managers to invest in, and Albert gives a demo of the custom internal software they’ve built.
Thank you to Jake Kupperman, Sasha Kaletsky, Nathan Benaich, Amanda Robson, and Dave Fontenot for helping brainstorm topics for the conversation.
Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeel
Try Hanover Park - the modern, AI-native fund admin https://www.hanoverpark.com/Turner
Timestamps:
(5:01) Top 3 forms of alpha in VC
(10:11) Other ways to generate alpha
(12:47) Avoiding false positives
(17:11) Optimal fund size and portfolio construction
(22:25) The role of Luck
(23:55) Spin-out vs outsider funds
(25:43) Level’s backchannel reference process
(29:29) Finding alpha in Criticality Investing
(34:45) Why capital flows drive all returns
(43:53) Early, consensus investing has the most alpha
(48:46) Networks are more persistent than performance
(52:03) The strongest and weakest networks
(58:41) Demo of Level’s internal software
(1:04:48) Building a Fund of Funds around their data
(1:10:01) Ideal LP GP relationship
(1:12:39) Benchmarks are relative
(1:15:39) VC funds using AI
(1:17:43) How venture will change in the next 10 years
Referenced
Level Ventures: https://levelvc.com/
Level’s Research Papers: https://levelvc.com/research/
Follow Albert
LinkedIn: https://www.linkedin.com/in/albertazout/
Newsletter: https://albertazout.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/
Will O’Brien is the Co-founder of Ulysses, building autonomous, low cost robots for the ocean.
Will considers the ocean humanity’s next great frontier. It makes up over $2.5 trillion of economic activity, considering things like fishing, aquaculture, shipping, mining, communications infrastructure, and defense. Yet we know more about the surface of the moon’s of Saturn than we do the bottom of our own ocean.
We talk about Ulysses first product, restoring plant life in the ocean, their modular autonomous underwater robotics platform, advice for anyone selling to governments, crazy businesses that could eventually evolve in the ocean, and why the way we finance startups needs to change.
Will also loves conspiracy theories, and we talk about some of our favorites, and why he thinks people who believe them could make good startup founders.
Thank you to Will’s brother’s Harry and Jacob O’Brien, and to upcoming guest of the show Eoghan McCabe for helping brainstorm topics for Will.
Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeel
Timestamps:
(4:03) Peace offering of Dubai Chocolate
(5:30) Modern internet theory
(7:40) The ocean is the last frontier
(11:53) Ulysses: read/write layer of the ocean
(13:35) The $2.5 trillion ocean economy
(15:14) Current ocean unit economics
(18:50) Starting with seagrass ecosystem restoration
(24:13) Modular, underwater autonomous robots
(27:31) Starting Ulysses with a group chat
(29:51) Raising a Seed from Lowercarbon with no network off a cold calendar invite
(32:24) Economic use cases for ocean robotics
(36:07) Spiritual energy from the ocean
(42:36) First Ramp podcast ad in Irish
(43:21) Floating cities, sub tours, deep sea mining, iron fertilization
(51:47) $10+ billion in shipwrecked treasure
(53:18 Atlantis is real
(59:46) Craziest alien conspiracy theories
(1:01:28) Sinking the titanic to create the Fed
(1:04:19) Conspiracy theory believers are good founders
(1:07:55) How to sell to the government
(1:13:28) Writing a letter to an Irish billionaire
(1:16:00) Finding meaning after living with Monks in Nepal
(1:27:10) Why financial innovation precludes economic dominance
(1:44:01) The SPV peddler business model
(1:46:35) Should we bring back SPAC’s?
Referenced
Ulysses: https://www.ulysses.eco/
Careers at Ulysses: https://www.ulysses.eco/jobs
The Richat Structure: https://en.wikipedia.org/wiki/Richat_Structure
Jesse Michael’s YouTube: https://www.youtube.com/@JesseMichels
Brad Jacobs: https://en.wikipedia.org/wiki/Brad_Jacobs_(businessman)
Follow Will
Twitter: https://x.com/willobri
LinkedIn: https://www.linkedin.com/in/will0brien
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/
Isaac Medeiros is the Founder of Mini Katana and Kanpai Foods.
Isaac’s content gets over 1 billion views per month. Our conversation gets into content strategy from a high level down to tactical decisions, differences between the TikTok and YouTube algorithms, and how AI will impact content creation.
We also get into Isaac’s origin story building consumer brands, why TikTok made food an interesting category for new products, how to get a product into retail stores, and why you shouldn’t sell into retail.
Isaac also shares how tariff’s impacted his company. They became unprofitable overnight, and he had to move his entire supply chain from the US to Mexico in 60 days.
Thank you to Sean Frank @ Ridge and Kevin Espiritu @ Epic Gardening for their help brainstorming topics for Isaac.
Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here.
Timestamps:
(3:46) 165 million views in two days
(5:15) Followers don’t matter, build a binge bank
(11:21) How to monetize an audience
(14:36) Identify outliers for content ideas
(17:13) Should founders make their own content?
(19:34) Starting Mini Katana
(23:39) $10m revenue in two years w/ $0 CAC
(25:56) Difference between TikTok and YouTube algorithms
(29:38) When to experiment with a second platform
(32:20) Starting Kanpai, a freeze-dried candy company
(36:54) Why freeze-dried candy wasn’t popular
(38:22) Why you shouldn’t sell in retail
(41:12) Why you should sell in retail
(47:05) Downsides of selling to large retailers
(49:52) Should CPG brands raise money?
(57:59) Moving manufacturing from US to Mexico in 60 days due to tariffs
(1:04:20) Why you don’t want to be first in a category
(1:08:06) Other CPG creators Isaac follows
(1:09:15) Elon Musk, Charlie Munger, Mark Cuban
(1:11:55) Labubu’s
Referenced
Previous episode with Kevin Espiritu
Previous episode with Sean Frank
Follow Isaac
Follow Turner
Subscribe to my newsletter to get every episode + the transcript in your inbox every week.
Michael Dempsey is the Managing Partner at Compound, a thesis-driven, research-centric investment firm.
We spent two hours talking through the past, present, and future of a bunch of topics in technology and investing.
Michael started investing in AI in 2016. He was the first investor in now-unicorns Runway and Wayve. But he hasn’t done much AI investing over the past few years. We talk about why, how AI will intersect with robotics, the future of things like crypto and synthetic biology, and why so many deep tech companies mess up economic value capture.
We also talk about what it means to be a thesis-driven venture firm, Compound’s research process and how to replicate it, what private and public market investors can learn from each other, advice for anyone starting in venture today, how to build a brand in VC, and why venture firms don’t compound and actually decay over time.
Thank you to Kevin Kwok, Andy Weissman, Cristóbal Valenzuela, Blake Robbins, and Smac at Compound for their help brainstorming topics for this.
Special thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here.
Timestamps:
(4:09) Leading Runway’s Seed in 2018
(10:15) Short-term ARR vs long-term sustainability
(16:20) Compound, a research-centric investment firm
(18:41) Investing in bio, crypto, real-world AI, and healthcare
(23:58) VC firms do not compound, they decay over time
(29:27) How to build a research-focused investment firm
(41:30) Current state of venture slop
(45:43) Building a brand as a VC firm
(52:31) Investing in Wayve in 2016
(58:53) Why deep tech companies screw up economic value capture
(1:04:57) How to approach massive funding rounds
(1:08:36) Should VCs “play the game on the field”?
(1:15:33) Compound is a forecasting firm
(1:21:37) Advice for young people getting into VC
(1:26:48) Public market investors underappreciate narratives
(1:31:20) Michael’s crypto thesis + real use cases
(1:40:07) Why crypto hasn’t seen mass adoption yet
(1:49:00) Humanoid robots won’t work
(1:54:42) Should you make a hyped launch video?
Referenced
Follow Micahel
Follow Turner
Subscribe to my newsletter to get every episode + the transcript in your inbox every week.
Subscribe to my newsletter to get every episode + the transcript in your inbox every week.
Ryan Hoover is the Founder of Product Hunt and Weekend Fund.
Ryan’s probably helped more founders launch their products than anyone else on Earth. We talk about starting Product Hunt as an email list, and he open sources the growth flywheel that propelled it to one of the most important places in technology.
Ryan unpacks how he built and scaled a community around the product, how online communities have changed over time, how we’re thinking about software in the age of AI (tech will change, human behavior won’t), and how status has changed in Silicon Valley.
We also talk about starting Weekend Fund to invest in other founders, his first 400x investment, investing in consumer health, and why he started investing in other funds.
Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 signing-up here.
Timestamps:
(5:52) Helping founders with software
(15:36) Early ideas for Product Hunt in 2013
(19:14) Starting as a social email list
(26:26) Product Hunt’s growth flywheel
(31:15) AI won’t change human behavior
(34:12) An audience is not a community
(36:42) Why every community needs utility
(38:52) Communities have shifted towards group chats
(40:10) How AI changes building products
(49:35) Importance of craft
(52:30) Starting Weekend Fund, Ryan’s 400x investment
(56:57) Weekend Fund’s software experiments
(59:26) What makes Ryan’s investing unique
(1:02:16) Why Ryan has a small fund
(1:07:41) Peptides, GLP-1’s, Ketamine
(1:18:57) Investing in funds
(1:20:53) Ways LPs can add value for GPs
(1:23:05) How status has changed in Silicon Valley
(1:31:37) Backing founders with secrets, why failing is hard
Referenced
Hooked: How to Build Habit Forming Products
Get Your Wish - Porter Robinson
Silicon Valley’s new status symbols
Follow Ryan
Follow Turner
Subscribe to my newsletter to get every episode + the transcript in your inbox every week.
Sahill Poddar is the Co-founder and CEO of Parafin, helping marketplaces, vertical SaaS, and point of sale providers offer financial services their merchants.
Sahill and his team have quietly built Parafin to nearly a $100m GAAP revenue run rate in only four years, and they've done it in an industry that's become a Silicon Valley graveyard: SMB lending.
Sahill talks about how they partnered with other marketplaces, vertical SaaS, and point of sale providers to offer financial services to SMBs at scale, landing DoorDash as their first customer before building the product, and advice for technical teams learning enterprise sales.
Sahill's a fascinating founder, as he started his career getting a PhD discovering the Higgs boson particle at CERN’s Large Hadron Collider. We talk about physics, he explains how the Large Hadron Collider works, why physics is just real world machine learning, and all the lessons he learned on the growth teams at Facebook and Robinhood (including the way Robinhood acquired most of its userbase!)
A thank you to Hans Tung at Notable Capital, Nick Shalek at Ribbit, and Mahdi Raza at Pathlight for their help brainstorming topics for the conversation.
Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get your $250 here.
Timestamps:
(4:06) Lending to SMBs inside marketplaces and platforms
(9:39) Why SMB lending is so hard
(12:50) Three ways AI is changing Fintech
(16:47) Silicon Valley’s graveyard of SMB lenders
(22:44) Getting a PhD in Particle Physics
(26:15) How CERN's Large Hadron Collider works
(31:49) Discovering new dimensions
(34:10) Building billion user data sets at Facebook
(39:53) Working with other physicists at Robinhood
(50:29) Growth lessons from FB + Robinhood
(1:00:57) Starting Parafin, embedded, horizontal SMB lending
(1:06:09) Why credit is the biggest problem for SMBs
(1:10:53) Raising a Seed from Ribbit pre-product
(1:13:25) Landing DoorDash as the first customer
(1:16:51) Mastering B2B sales as a technical founder
(1:22:58) Lessons from Vlad at Robinhood
Referenced
Follow Sahill
Follow Turner
Subscribe to my newsletter to get every episode + the transcript in your inbox every week.
Our TOPPODCAST Picks 
