The Peel with Turner Novak

Turner Novak
  • 4.6 (11)
  • TECHNOLOGY
  • UPDATED WEEKLY

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. Footwork’s Secret Sauce | Mike Smith and Nikhil Basu Trivedi

    3D AGO

    Footwork’s Secret Sauce | Mike Smith and Nikhil Basu Trivedi

    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/

    1h 32m
  2. Inside Hanover Park: Building an AI-Native Service Business, Growing to $15B in Assets

    MAR 18

    Inside Hanover Park: Building an AI-Native Service Business, Growing to $15B in Assets

    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/

    1h 12m
  3. Inside Canada’s Fastest Growing AI Company | Spellbook, Scott Stevenson

    MAR 12

    Inside Canada’s Fastest Growing AI Company | Spellbook, Scott Stevenson

    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/

    1h 36m
  4. Benchmark’s Chetan Puttagunta on the Past, Present, & Future of Software

    MAR 4

    Benchmark’s Chetan Puttagunta on the Past, Present, & Future of Software

    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/

    1h 30m
  5. Inside Serval: Building the System of Intelligence for IT | Jake Stauch

    FEB 27

    Inside Serval: Building the System of Intelligence for IT | Jake Stauch

    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/

    1h 25m
  6. Garry Tan on the Past, Present, and Future of YC

    FEB 19

    Garry Tan on the Past, Present, and Future of YC

    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/

    1h 24m
  7. Building the Wearable That Gets You Stronger | Miranda Nover, Co-founder of Fort Health

    FEB 13

    Building the Wearable That Gets You Stronger | Miranda Nover, Co-founder of Fort Health

    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/

    1h 35m
  8. How Duo Security went Zero to $1B ARR in Ann Arbor | Dug Song, Jon Oberheide

    FEB 5

    How Duo Security went Zero to $1B ARR in Ann Arbor | Dug Song, Jon Oberheide

    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/

    2h 9m
See All (134)

4.6
out of 5
11 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 - 2026
  • Episodes
    134
  • Rating
    Explicit
  • Copyright
    © Turner Novak
  • Show Website
    The Peel with Turner Novak

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