The Peel with Turner Novak

Turner Novak
  • 4.6 (10)
  • TECHNOLOGY
  • UPDATED WEEKLY
The Peel with Turner Novak

Exploring 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.

  1. Solving the Hardest Problems in Dev Tools | Jake Cooper, Founder of Railway

    1D AGO

    Solving the Hardest Problems in Dev Tools | Jake Cooper, Founder of Railway

    Jake Cooper is the Founder of Railway. This conversation explores how AI accelerates the need for strong backend infrastructure, when to build vs buy in AI software, and why there are only two moats: solving hard problems and doing hard things. We also unpack Railway’s bold product bets, like enabling creators to earn revenue with backend templates, building their own data centers, and not building their own AI models. Jake also talks about their four week new hire onboarding, how they build a problem roadmap, why operators should be managers, and why you should almost never work weekends. Thank you to Angelo Saraceno @ Railway and Erica Brescia Bacon @ Redpoint for 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: (3:33) Solving the hardest problems in dev tools (8:16) Starting with the hardest thing (11:18) How AI accelerated the need for Railway (12:50) Importance of backend in AI-native software (16:52) Jake’s angel fundraise strategy (20:51) Resisting AI for so long (25:32) Using AI to get leverage (29:57) Build vs buy in AI software (33:22) When Jake knew Railway was working (34:27) Creating infrastructure templates (38:04) Building data centers and a cloud service (40:27) Two moats: Hard problems and hard things (46:25) Hitting 8-figures in revenue (48:47) Railway’s four week onboarding (54:25) Building a problem roadmap (56:16) You can’t set your own culture (1:01:58) Railway’s viral “How We Work” post (1:08:39) Using Discord instead of Slack (1:11:25) How hypergrowth companies mess up org design (1:14:03) Why you shouldn’t work weekends (1:19:45) Not betting big on AI models (1:21:53) Lessons from Zuck, Martin Scorsese Referenced Railway Careers at Railway The Inward Draw of Capitalism How We Work Volume 1 Volume 2 Volume 3 Volume 4 Follow Jake Twitter LinkedIn Substack Follow Turner Twitter LinkedIn Subscribe to my newsletter to get every episode + the transcript in your inbox every week.

    1h 28m
  2. How WordPress Powers 43% of the Internet | Matt Mullenweg, Co-founder and CEO, Automattic

    JUL 11

    How WordPress Powers 43% of the Internet | Matt Mullenweg, Co-founder and CEO, Automattic

    Today’s guest is Matt Mullenweg, Co-founder of WordPress, which powers over 43% of all websites on the internet, and founder of Automattic. Our conversation explores the 2000’s internet, the early days of Automattic, and the decisions and philosophies that set them up for success 20 years later. We talk open source software, why Matt’s such a big proponent of it, how Automattic built its business model as one of the first SaaS companies (that now owns companies like Tumblr and WooCommerce), and how AI is changing engineering. Matt also shares how to build a community around your product, “Conscious Capitalism”, what he learned running one of the first distributed teams, and lessons on optimism from Walt Disney. 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. Sign-up for Ramp and get $250 here. Timestamps: (3:48) WordPress: Powering 43% of the internet (8:30) Outcompeting Reid Hoffman’s startup in the early days (14:03) Why open source wins over the long-term (16:21) Business models in open source (21:12) Starting Automattic in 2005, one of the first SaaS companies (28:45) Spending most of Automattic’s Seed round on servers (33:36) How to use Community + Word of Mouth for early growth (38:38) Matt’s current situation with WP Engine (43:30) How to give back in open source (53:55) Best practices from 20 years of running a remote company (59:59) Lessons on optimism from Walt Disney (1:12:33) How AI is changing coding (1:16:09) Automattic's internal employee secondary market (1:23:51) How open source increases longevity (1:26:08) Matt’s favorite classical thinkers Referenced: Automattic Wordpress Matt’s Blog Bay Lights in SF Innocence Project Vesuvius Challenge Plastic List The Giving Pledge DAFFY Pessimist Archive Matt's favorite quote from Rudy Francisco Maintenance by Stuart Brand We are as Gods by Stuart Brand Marginal Revolution by Tyler Cohen Follow Matt Twitter LinkedIn Follow Turner Twitter LinkedIn Subscribe to my newsletter to get every episode + the transcript in your inbox every week.

    1h 29m
  3. Gamma's Journey to $50M ARR with 30 Employees | Co-founder and CEO Grant Lee

    JUL 3

    Gamma's Journey to $50M ARR with 30 Employees | Co-founder and CEO Grant Lee

    Grant Lee is the Co-founder & CEO of Gamma, building instant PowerPoints, presentations, and websites with AI. As someone who’s made a lot of decks, its refreshing how Gamma thinks about slides starting with the words and narrative, using AI to build the design around the story. Gamma has put up impressive metrics, growing from zero to $50 million in ARR and 50 million users with only 30 employees. They’ve also had zero employee attrition, and a negative lifetime burn rate, with more cash in the bank than they’ve raised. We talk about building a horizontal product instead of for a specific vertical, why Grant likes hiring generalist’s, how a quarter of the team is designers, why they’ve never raised large funding rounds, and how they run the company with an efficient team while not subscribing to 996 working hours. Grant also shares how Gamma rebuilt their entire product to be AI-native in the months after ChatGPT launched, and how every department at Gamma uses AI internally. Thanks to Anamitra and Gaurav at Afore, Shiyan @ Hustle Fund, Evan @ South Park Commons, and Vas @ Accel for helping brainstorm topics for Grant. Special thanks to presenting sponsor of The Peel, Ramp. Ramp: Time is money. Save both with Ramp. Join 40,000+ companies, go to https://ramp.com/ThePeel Numeral: The end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel Timestamps: (3:46) Gamma: The anti-Powerpoint (5:56) How to be efficient with a small team (7:58) Importance of full-stack generalists (12:15) How to hire problem solvers (15:57) Changing slides from designs to narratives (20:13) Gamma’s freemium AI business model (22:36) Ignoring conventional wisdom with a horizontal product (28:47) Why Gamma started with Slides (32:21) Raising a Pre-Seed for a horizontal product (38:25) Why Gamma avoided hyped funding rounds (40:57) How fundraising impacts recruiting (43:40) Liquidation preferences and employee equity (47:08) Gamma’s zero employee attrition (49:54) Working in-person during COVID (52:15) Using waitlists to batch new user cohorts (56:08) Re-building the product to be AI-native (58:17) How to improve your onboarding (1:00:46) Benefitting from AI models getting better (1:05:10) Growing from 60k to 50 million users (1:07:30) How to stand out as an AI company (1:09:23) Creating a Gamma API (1:11:37) How Gamma uses AI internally (1:15:06) Why Gamma doesn’t do 996 working hours (1:19:54) 4-month product sprints (1:22:16) Parenting hacks: sleep, exercise, nutrition (1:24:26) Brand and community lessons from Nike and Apple Referenced Gamma Careers at Gamma Optimizely NotebookLM Fin / Intercom: Afore Capital Follow Grant Twitter LinkedIn Follow Turner Twitter LinkedIn Subscribe to my newsletter here to get every episode + the transcript in your inbox every week.

    1h 31m
  4. Inside the $2 Trillion Employee Benefits Market | Ryan Sachtjen, Threeflow

    JUN 26

    Inside the $2 Trillion Employee Benefits Market | Ryan Sachtjen, Threeflow

    Ryan Sachtjen is the Co-founder and CEO of Threeflow, building software for employee benefits brokers and insurance carriers. We start with a deep dive into the nearly $2 trillion dollar employee benefits market, including the structural issues that actually give the smallest companies the most leverage. We also talk about insurance more broadly, AI opportunities in insurance, lessons from kickstarting a marketplace doing nearly $3B in volume, when his wife got cancer two months after closing Threeflow's seed round, and how his co-founders adjusted to support him. Special thanks to Bolt for supporting this episode! Join the world’s largest hackathon - up to $1m in prizes. Sign-up here. Timestamps: (3:57) Threeflow: B2B benefits marketplace (5:50) How the benefits industry works (9:20) The importance of brokers in insurance (12:32) Benefits broker software stack (15:36) How to make money in employee benefits (21:11) Ways to compete in insurance (26:34) How AI is changing insurance (31:01) What its like to be an insurance broker (35:37) Starting ThreeFlow in 2016 pre-LLMs (40:13) The 128 day walk through Europe before Threeflow (44:47) When his wife was diagnosed with breast cancer (50:23) Advice for founders on surviving large personal events (52:46) Threeflow’s unorthodox Seed round (59:46) How to vet your investors (1:04:14) Why insurance brokers exist (1:05:08) How to build a marketplace on top of Vertical SaaS (1:10:53) Choosing a marketplace entry point (1:15:05) $2.5B in premium volume on Threeflow workflows (1:26:39) Importance of supply side volume in a marketplace (1:31:21) Fundraising without a formal process (1:33:03) Hiring for “just get stuff done” (1:36:22) AI opportunities in insurance (1:41:05) Building software in insurance (1:44:56) Tactics for running a distributed team (1:49:04) Creating your own playbooks Referenced Try Threeflow Careers at Threeflow Follow Ryan LinkedIn: https://www.linkedin.com/in/ryansachtjen/ 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/

    1h 54m
  5. How to Raise a VC Fund Today, How AI is Changing Fintech, Traits of Top Emerging Managers, Why Everyone is Selling Secondaries, Triple-Layered SPVs | Samir Kaji, Co-founder and CEO of Allocate

    JUN 19

    How to Raise a VC Fund Today, How AI is Changing Fintech, Traits of Top Emerging Managers, Why Everyone is Selling Secondaries, Triple-Layered SPVs | Samir Kaji, Co-founder and CEO of Allocate

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

    1h 42m
  6. How to Skip Your Seed, Pre-Seed Lessons Building Afore to $500M+ AUM | Anamitra Banerji

    JUN 12

    How to Skip Your Seed, Pre-Seed Lessons Building Afore to $500M+ AUM | Anamitra Banerji

    Anamitra Banerji is the Co-founder of Afore Capital, an SF-based VC firm that specializes in investing in pre-seed stage companies. Our conversation gets into the evolution of Pre-Seed as a category, why Pre-Seed is more than option checks, what Afore looks for when backing founders before they even have a product, how to skip your Seed and go straight to a Series A, and how to run a fundraise process. We also get into Afore’s Founder in Residence program, why every VC started an accelerator, how AI is changing venture, joining Twitter as the first PM, and how Oprah helped create the legendary verified checkmark. Thanks to Gaurav Jain and Derrick Li at Afore for their help brainstorming topics for Anamitra. And special thanks to Bolt and Warp for supporting this episode. Bolt: Help them break a world record for the largest hackathon - up to $1m in prizes. Sign-up. Warp: Automates payroll, handles multi-state tax compliance, and streamlines international contractor payments, so founders can focus on building, not busywork. Try it here. Timestamps: (4:00) Afore: Starting in 2016 to build the pre-seed category (8:11) The unstructured data Afore underwrites at pre-seed (11:21) Pre-seed is determining bronze from gold (16:03) Why pre-seed is more than option checks (20:33) The secret to raising a Series A (23:20) Running a tight fundraise process (32:05) Skipping your Seed round (34:01) How to measure obsession in a founder (39:20) Knowing when to follow-on (40:54) Figuring out what really matters in a business (42:36) Afore’s Founder in Residence program (49:44) Pros / Cons of more access to capital for founders (52:27) Two reasons YC made every VC launch an accelerator (1:01:05) Why AI is forcing VCs to invest earlier (1:06:55) Will AI commoditize software? (1:08:29) Growing up in India, starting his first company (1:10:39) Coming to the US for school, joining Overture + Yahoo (1:14:05) Joining Twitter as first PM, creating the Verified check for Oprah (1:18:55) Building Twitter’s first ad product (1:20:28) Why non-founders can’t take foundational risks (1:23:02) Starting Afore for the Pre-Seed opportunity (1:27:47) Raising Afore Fund 1 (1:31:14) How to raise your first fund (1:33:33) Was Turner the best Afore intern ever? Referenced Afore Capital K9 Capital Afore’s Founder in Residence Program: Speedrun PearX Neo Accelerator Gamma Develop Health Follow Anamitra Twitter LinkedIn Follow Turner Twitter LinkedIn Subscribe to my newsletter to get every episode + the transcript in your inbox every week.

    1h 36m
  7. Benchmark’s Eric Vishria on Going Zero to $100M ARR in 12 Months, Archetypes of Top AI Founders, Why Storytelling is a Superpower, How Benchmark Makes New Investments

    JUN 5

    Benchmark’s Eric Vishria on Going Zero to $100M ARR in 12 Months, Archetypes of Top AI Founders, Why Storytelling is a Superpower, How Benchmark Makes New Investments

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

    1h 46m
  8. Samsara’s Journey to $26B Public Company | Sanjit Biswas, Co-founder and CEO

    MAY 29

    Samsara’s Journey to $26B Public Company | Sanjit Biswas, Co-founder and CEO

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

    1h 32m
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4.6
out of 5
10 Ratings

About

Exploring 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.

Information

  • Creator
    Turner Novak
  • Years Active
    2023 - 2025
  • Episodes
    101
  • Rating
    Explicit
  • Copyright
    © Turner Novak
  • Show Website
    The Peel with Turner Novak

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