The Peel with Turner Novak – Details, episodes & analysis

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The Peel with Turner Novak

Turner Novak

Technology

Frequency: 1 episode/8d. Total Eps: 139

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.

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Apple Podcasts

🇨🇦 Canada - technology
04/05/2026
#87
🇬🇧 Great Britain - technology
21/11/2024
#89
🇺🇸 USA - technology
21/11/2024
#86
🇺🇸 USA - technology
20/11/2024
#67

Spotify

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https://www.linkedin.com/in/turnernovak
106 shares
https://www.linkedin.com/in/turnernovak/
44 shares
https://www.linkedin.com/in/jonathan-neman-9a28aa8/
8 shares

https://twitter.com/TurnerNovak
182 shares
https://twitter.com/StockJabber
3 shares
https://twitter.com/DenehyXXL
2 shares

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Score global : 38%

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Recruiting From Zero to One with Nakul Mandan, Co-founder of Audacious Ventures

Episode 1

Thursday, November 14, 2024 • Duration 01:46:21

Nakul Mandan is the founder of Audacious Ventures. Prior to Audacious, he was a partner at Lightspeed, joining from Battery, which he joined in ‘09 in the middle of the financial crisis while living in India.

This conversation explores his journey immigrating to Silicon Valley and building an early stage venture firm from the ground up.

We get into why most VCs aren’t helpful with recruiting at the zero to one stage, his thesis on starting an early stage venture firm to help founders hire A+ teams, a crash course on early stage recruiting and building a sales team, and how COVID hit right after he left Lightspeed to raise Audacious Fund 1.

Timestamps:
(00:00) Intro
(03:43) Evolution of VC platform teams
(09:53) How Audacious runs in-house recruiting processes
(15:16) The reason large firms can’t help with Seed stage recruiting
(17:06) Immigrating from India to the US mid-financial crisis
(21:59) Silicon Valley's secret weapon
(25:59) The opportunity to start a recruiting-focused Seed firm
(30:14) Raising Audacious $90m Fund 1 in April of 2020
(36:58) The new guard of Seed firms
(39:23) Why $50-75m is the minimum viable institutional fund size
(41:48) How to work with the best founders
(45:30) Navigating deal dynamics, term sheets, and valuations
(52:24) The two hardest parts about starting your own fund
(54:32) Lessons applied raising Audacious $125m Fund 2 in 2023
(58:46) Evolving from a PMF-first to Founder-first investor
(01:02:09) Five traits of force of nature founders
(01:07:05) How to build an A+ team
(01:11:46) The importance of backchanneling
(01:13:54) Why everyone thinks they’re a good people reader
(01:14:35) Two most common mistakes in recruiting
(01:20:59) Determining urgency of a customer’s problem
(01:22:55) Hiring and scaling your first sales team
(01:25:55) Why marketing is the hardest role to hire for
(01:31:59) What good sales people look like
(01:35:43) How to move up market + how to do pilots
(01:43:40) Why Nakul admires Rafael Nadal

Referenced:
Audacious: ⁠https://www.audacious.co/ ⁠
Nakul’s immigration journey: ⁠https://www.nakulmandan.com/blog/2024/an-immigrant-living-the-american-dream⁠
Force of nature founders: ⁠https://www.nakulmandan.com/blog/2024/traits-i-look-for-in-founders⁠
Early GTM hiring: ⁠https://www.nakulmandan.com/blog/2023/initial-gtm-hiring-for-saas-startups⁠
Follow Nakul:
Twitter: ⁠https://x.com/nakul⁠
LinkedIn: ⁠https://www.linkedin.com/in/nakulmandan⁠
Follow Turner:
Twitter: ⁠https://twitter.com/TurnerNovak⁠
LinkedIn: ⁠https://www.linkedin.com/in/turnernovak/
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: ⁠https://www.thespl.it⁠

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Inside Rent the Runway’s Early Days and the Future of Commerce with Co-founder Jenny Fleiss

Season 1 · Episode 68

Thursday, November 7, 2024 • Duration 01:04:45

Jenny Fleiss is the Co-founder of Rent the Runway, and more recently started Roll Rider with her three kids.

We get into the early insights that led to Rent the Runway, building the company with no fashion or tech background, fundraising advice, what she’s thinking about the future of AI and commerce, and the latest company she’s building with her kids, Roll Rider.

For full show notes, visit: https://highlightai.com/share/9bc59c07-05ab-41aa-b37e-f35a7c92092d

Timestamps:
(00:00) Intro
(05:31) How social media was Rent the Runway’s first tailwind
(07:21) Being early to sustainable fashion
(09:21) Starting the company at HBS in 2008
(12:36) Launching with no fashion or tech background
(14:49) The three biggest early surprises
(18:44) Using “show don’t tell” to fundraise
(20:06) Why customer social proof was so important
(23:04) Spending only 10% of revenue on marketing
(25:12) Getting the NYT to cover their launch
(29:43) Early mistakes
(31:29) Re-building the product a few weeks before launch
(33:11) Why building their own logistics was so important
(38:59) Subscriptions, retail, and other key product decisions
(45:15) How the internet makes it harder to shop
(49:30) Building conversational commerce at Walmart
(53:48) Lessons from starting a company with her kids
(58:38) Favorite startups in AI and commerce
Referenced:
Rent the Runway: https://www.renttherunway.com/
NYT’s Launch Coverage: https://www.nytimes.com/2009/11/09/technology/09runway.html
Check out Roll Rider: https://rollrider.com/ Use code TURNER15 for 15% offFollow Jenny:Twitter: LinkedIn: Follow Turner:Twitter: LinkedIn: Subscribe to my newsletter to get every episode + the transcript in your inbox every week:

Inside the beehiiv Playbook with Tyler Denk, Co-founder and CEO

Thursday, September 5, 2024 • Duration 01:46:36

Tyler Denk is the Co-founder and CEO of beehiiv, the newsletter platform built for growth.

We go inside beehiiv’s early days, including joining MorningBrew as the second employee, lessons scaling to 3.5 million subscribers, the $75 million sale to Business Insider, and why I didn’t invest in beehiiv despite being an early customer.

Tyler takes us inside the playbook that grew to $1.5m in monthly revenue in less than three years, including how they first positioned the product in a crowded market, how beehiiv ships so fast, when a co-founder passing away less than one year into building the business, and the day GoDaddy took the entire beehiiv platform offline for 8 hours.

Timestamps
(00:00) Intro
(01:36) Why Turner didn’t invest in beehiiv (twice)
(03:04) Joining MorningBrew as the first employee
(15:28) Why newsletters are so powerful
(19:40) Scaling MorningBrew to 3.5 million subscribers and exiting to Business Insider
(23:14) Difference between startups and big companies
(26:26) Why beehiiv has two days of no meetings
(27:53) The initial insight to start beehiiv
(35:39) Building a programmatic newsletter ad marketplace
(39:52) Dissecting beehiiv’s nearly $20m rev run rate business model
(45:21) Inside beehiiv’s first funding round
(46:58) Where Turner’s reference check went wrong
(50:45) Litquidity and beehiiv’s initial product positioning
(52:59) How beehiiv builds in public
(57:41) Banning meetings two days per week
(01:00:13) Why the best remote teams always beat in-person
(01:06:19) The impact of a co-founder dying one year into the business
(01:11:50) Raising a Series A despite operating at breakeven
(01:16:14) Why Tyler writes public investor updates
(01:21:04) Moving fast, and “why perfect kills all momentum”
(01:26:03) When GoDaddy took beehiiv down for 8 hours
(01:29:57) Why Tyler writes a newsletter
(01:32:21) His Big Desk Energy Spotify playlist
(01:36:08) Why you never regret firing bad hires
(01:39:53) Looking up to Elon and Brian Chesky(01:41:34) Monk mode in Columbia

The Future of Software, AI, and Tax, Lessons Scaling Zero to One | Michelle Valentine, CEO of Anrok

Thursday, August 29, 2024 • Duration 01:10:49

Michelle Valentine is the Co-founder and CEO of Anrok, the sales tax platform for software companies.

We talked trends in software consolidation, lessons working with Anrok’s first customers, advice on fundraising, scaling a sales team, and early tricks for founders to avoid future tax-related headaches.

Timestamps

(00:00) Intro (02:19) The trend of software consolidation (03:00) Why billings and payments isn’t consolidating (06:09) Early tricks for avoiding future tax headaches (08:42) Founder lessons from first being a VC (09:28) The two catalysts that led to Anrok (17:15) How software companies used to figure out sales tax (22:51) Raising Anrok’s Seed round in 48 hours (25:42) How to join a VC's scout program (28:24) Fundraising lessons from being an investor (34:24) Surprising results from the very first “easy file” product (38:30) Lessons getting the first customers from outbound (40:19) Why you should make your first two sales hires at the same time (41:50) Sales advice when scaling into enterprise customers (46:19) How your Seed round helps raise your A and B (47:24) The reason AI and LLMs are so hard to predict (50:58) Michelle’s favorite Claude use cases (53:51) Predicting market sizes, and why Figma’s seemed small (57:39) How to invest in AI right now (1:01:01) Advice on changing your opinion (1:04:10) Getting outside your comfort zone (1:05:04) Michelle’s go-to interview question (1:34:50) The most ridiculous SPACs (1:07:23) Lessons from Scott Cook, the founder of Intuit

Referenced Check out Anrok: https://bit.ly/3YTb0ED Anrok’s Journal Entries Newsletter: https://bit.ly/3AxrtUV Anrok Mid-year SaaS Sales Tax Review: https://www.anrok.com/resources/mid-year-saas-sales-tax-review-2024 Michelle’s Article on AI, Part 1: https://www.linkedin.com/pulse/fog-ai-what-investors-missing-part-one-michelle-valentine Part 2: https://www.linkedin.com/pulse/fog-ai-what-investors-missing-part-two-michelle-valentine Part 3: Superintelligence:

ShipHero’s Journey to $12B | Aaron Rubin, Founder and CEO

Season 1 · Episode 57

Thursday, August 22, 2024 • Duration 01:16:52

Building an enterprise-ready SaaS app? WorkOS has got you covered with easy-to-integrate APIs for SAML, SCIM, and more. Start now at https://bit.ly/WorkOS-Turpentine-Network. Aaron Rubin is the Founder and CEO of ShipHero, a warehouse management system for brands and 3PL providers. We talk through Aaron’s journey building ShipHero, starting with what is now the largest Jiu Jitsu apparel brand in the US, which he almost went bankrupt running during the financial crisis. He shares how that business led to ShipHero, takes us inside the early days, explains why warehouse robotics and 4PL’s are overhyped, and discuss the rapid rise of TikTok Shop, Temu, and Shein. Timestamps (00:00) Intro (02:01) The USPS shipping label scam (07:10) Starting the largest Jiu-Jitsu apparel brand (09:46) Narrowly avoiding bankruptcy in 2008 (17:08) Why ecommerce is so hard (21:16) Starting ShipHero to manage their own warehouse (28:00) Powering Shopify’s early fulfillment network (30:59) How 3PL’s are still solving basic problems (34:02) Why warehouse robotics is overhyped (41:48) Where drones fit into logistics (44:55) Aaron argues why the 4PL model doesn’t work (55:40) TikTok Shop is the fastest growing US ecommerce channel ever (58:42) How Temu and Shein leverage the 321 program to avoid tariffs (1:02:49) Why Temu and Shein are slowing US ecom growth (1:04:17) Topgrading: The most boring, most valuable hiring strategy (1:11:29) Business lessons from playing poker Referenced ShipHero: https://shiphero.com/ Topgrading: https://www.amazon.com/Topgrading-Hire-Coach-Keep-Players/dp/094400234X Where to find Aaron Twitter: https://x.com/AaronandML LinkedIn: https://www.linkedin.com/in/aaronandml Where to find Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Newsletter: https://www.thespl.it

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Inside the Logan Bartlett Show, Investing Through Market Cycles + Bubbles, Dissecting VC Frameworks

Season 1 · Episode 56

Thursday, August 15, 2024 • Duration 01:32:06

Logan Bartlett is a Managing Director at Redpoint.

If you like startups and you listen to podcasts, you’re probably familiar with his podcast, the Logan Bartlett Show. We talk about how it first got started, plus all his tricks for growing the podcast, including his canonical episodes in 2022 that helped pop the web3 bubble.

We also talk market cycles and bubbles, and what Logan’s seeing in the data today, especially in AI, plus Logan’s philosophy’s on venture capital as an asset class, his favorite under the radar investors, and advice for his younger self.

Timestamps: (00:00) Intro (01:33) Not getting invited to Michael Rubin’s white party (04:29) Meeting on Twitter during COVID (11:09) How Logan and I benefited from Twitter (16:55) Early days of the Logan Bartlett Show (22:10) Why podcasts are so hard to grow, and how Logan did it (24:50) Learning YouTube’s the best for podcast growth (29:51) Inside Logan’s web3 episodes with Zach Weinberg (32:07) Lessons from studying history and market cycles (33:15) Producer Ben fact checking Logan's historical railroad statistics (39:42) How to invest in and around bubbles (51:00) Market data from Redpoint’s 2024 AGM update (55:12) Differences between companies valued at 100x and 5x ARR (1:00:04) The Barbell Theory of asset management and why Logan disagrees it will happen in VC (1:09:40) Ways VCs can actually add value (1:12:27) Redpoint’s founding story + greatest hits (1:18:14) The most underrated investors and founders (1:21:35) Advice for young people: pick a niche, go deep, stay focused

If you enjoy this conversation and you’re not already, make sure to like, comment, follow, and subscribe to my newsletter in the show notes to get future episodes in your inbox every week.

Referenced: Clearspace https://www.getclearspace.com/ Acquired’s TikTok episode https://www.acquired.fm/episodes/tiktok Gorilla Game https://www.amazon.com/Gorilla-Game-Picking-Winners-Technology/dp/0887309577 Redpoint’s AGM Update

Lessons From Two Exits + Building Electric to Automate IT Management | Ryan Denehy

Season 1 · Episode 55

Friday, August 9, 2024 • Duration 01:33:53

Ryan Denehy is the founder and CEO of Electric, software that helps businesses manage their IT and IT support.

We talk through his first two startups from founding to exit, the early days of getting Electric off the ground, and Ryan’s frameworks for fundraising, recruiting, and sales.

Timestamps: (00:00) Intro (03:05) Building an ad network for extreme sports websites (11:07) Why a better pipeline solves all problems (13:24) Ryan’s trick for hiring executives (17:00) Selling the ad network to USA Today (18:11) Moving to SF to start a software company (21:33) Getting rid of his car to extend runway (24:23) Paying rent with credit cards (29:17) Struggling to raise a Series A (31:55) Using channel sales to grow the business (37:05) Almost running out of money before selling to Groupon (43:37) How cloud created the perfect timing to build Electric (48:33) Leveraging software and AI to automate manual human tasks (51:45) Why you should avoid buzzwords in marketing (53:57) Pros and cons of being a solo founder (56:14) Why Electric built a large initial board (01:02:41) Advice for picking lead investors (01:06:35) How VC fund dynamics have inflated Seed rounds (01:09:16) The downsides of high valuations (01:12:45) Almost wiring back the Seed round (01:16:37) Why every fundraise is a Pipeline problem (01:21:04) The reasons VCs actually pass on founders (01:26:42) Cutting the burn rate in 2022

Electric.ai: ⁠https://www.electric.ai/⁠

Where to find Ryan: Twitter: ⁠⁠⁠https://twitter.com/DenehyXXL⁠ LinkedIn: ⁠⁠⁠https://www.linkedin.com/in/ryandenehy/

Where to find Turner: Twitter: ⁠⁠https://twitter.com/TurnerNovak⁠⁠ LinkedIn: ⁠⁠https://www.linkedin.com/in/turnernovak/⁠⁠ Newsletter:

Frank Rotman | Building Capital One ($58B) and QED Investors ($4B AUM)

Season 1 · Episode 56

Thursday, August 1, 2024 • Duration 01:48:55

Get first-party targeting with Brave's private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. Warp: Don’t let payroll and compliance hold your startup back: visit https://joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll. Frank Rotman is the Co-Founder and CIO of QED Investors, and before that helped start Capital One. Frank and I go deep on their founding stories, as well as one of QEDs first big winners, Nubank. Frank also gives us a crash course on fintech, lending businesses, and crypto use cases; his hot takes on the venture asset class as a whole, with lots of advice for emerging managers; plus a case study on how high valuations too early on are bad for a startup. Timestamps: (00:00) Intro (04:22) Starting Capital One in 1988 (07:04) Spinning out as an IPO (10:42) Starting QED in 2008 before Fintech was a category (20:51) Raising their first outside fund (22:03) Investing early in Nubank (25:11) Fintech opportunities in India (27:45) De-risk investing in new markets (29:55) How financial services have changed over the past 30 years (31:33) Inside a new Capital One credit card in the 90’s (36:31) How most companies launched new cards in the 90’s (39:46) The most profitable types of credit card customers (42:00) Mistakes founders make building credit businesses (48:33) Frank’s “Three Body Framework” for VC (54:48) Losing strategies in VC (01:03:39) Unpacking why high valuations are bad for startups (01:16:20) Frank’s journey in and out of crypto (01:24:23) Actual use cases for stable coins and NFTs (01:34:09) Unpacking the lending supply chain (01:41:44) The difference between Fundamentalist and Revolutionary investors Referenced: VCs Three Body Framework: https://cdn.prod.website-files.com/605db59b78445cf5ae548e49/628b9d826f9af3217c9807a2_Three-Body%20Problem_%20Finding%20the%20New%20Stable%20Points%20in%20Venture%20Capital.pdf The House Money Effect: https://x.com/fintechjunkie/status/1466217991532650496 Fundamentalist vs Revolutionary Investors: https://www.linkedin.com/posts/frank-rotman_there-has-been-and-always-will-be-two-competing-activity-7128137991654445057-NuXf/ Where to find Frank: Twitter: https://twitter.com/fintechjunkie LinkedIn: https://www.linkedin.com/in/frank-rotman/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/

Car Dealership Guy: From Anonymous VC-Backed CEO to B2B Media with Yossi Levi

Season 1 · Episode 56

Thursday, July 25, 2024 • Duration 01:31:35

Warp: Don’t let payroll and compliance hold your startup back: visit https://www.joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll.

Get first-party targeting with Brave's private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign.

Yossi Levi shares his incredible story: transforming a small family car lot into a $28 million dollar powerhouse, founding venture-backed Gettacar and growing it to $90 million in revenue, before returning the capital to investors and growing his anonymous Twitter account into Car Dealership Guy, a B2B automotive media empire.

Yossi takes us inside his early marketing strategies, the hard earned lessons from chasing product-market fit, and the playbook to building a lean, scalable B2B media machine.

Timestamps: (00:00) Intro (07:26) Helping at his dad’s used car lot (11:22) How car dealerships make money (14:32) $28m revenue with Facebook ads (17:48) Putting gifts in customer trunks and filming it (22:58) Starting Gettacar to sell cars online (25:04) When a VC pulled his first term sheet (31:08) Recruiting full-time hires with part-time consulting gigs (34:45) Personally guaranteeing the debt used to finance vehicles (36:50) Helping subprime consumers buy cars online (39:24) How 2021 tricked them into thinking they had a sustainable business (41:57) Why you can’t rush Product Market Fit (42:23) Pivoting Gettacar to a profitable, PE-backed business before winding it down (47:22) Starting an anonymous Twitter to share insights from his day-to-day (50:08) Turning Car Dealership Guy into a media business (53:38) Doxing himself with a 13-minute documentary (58:29) Why you have to consume to be a good creator (1:00:04) Screensharing CDGs content schedule (1:02:59) Why every employee needs to generate content or revenue (1:09:27) Creating a car / auto influencer agency (1:11:34) Building a B2B automotive ad network (1:14:50) Evolving into a holding company (1:20:27) Importance of moving fast (1:23:34) Why people actually like sponsored content (1:28:08) Wishing he pivoted to B2B faster

The 26-Year Old Exposing $10B Public Companies | Edwin Dorsey, The Bear Cave

Season 1 · Episode 52

Thursday, July 18, 2024 • Duration 01:53:27

Warp: Don’t let payroll and compliance hold your startup back: visit https://joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll.

Edwin Dorsey is the author of The Bear Cave, a weekly newsletter exposing publicly traded companies that are misleading investors and harming customers.

I’ve enjoyed Edwin’s writing since he launched his newsletter the Bear Cave in 2020, and he shares his best kept secret for doing customer research: FOIA requests. We also get into short selling more broadly, common corporate red flags, the economics of his media business, almost getting kicked out of Stanford for raising issues at Care.com his sophomore year, Planet Fitness’s illegal billing operation, Hershey’s Mr. Beast problem, and the creator economy more broadly.

(00:00) Intro (05:11) How shorting works (07:20) How short sellers exposed Enron (10:51) Edwin’s process for finding bad companies (15:52) Root Insurance and aggressive pricing (20:14) FOIA: the best kept secret for company research (24:30) Biggest corporate red flags (28:17) Most common industries for bad actors (29:32) Why scammers target minorities and low income consumers (31:46) Edwin’s $1B to $10B market cap sweet spot (34:03) The challenges of mainstream media (38:15) Exposing Care.com as a student at Stanford (45:25) Why immediate board resignations are a red flag (49:45) Launching The Bear Cave in Feb 2020 (49:37) Using podcast appearances to grow (56:06) The newsletter's business model (1:00:00) Experimenting with side-newsletters, job boards, and consumer surveys (1:10:04) Planet Fitness: gym or illegal billing operation? (1:18:45) Herbalife the pyramid scheme (1:21:05) Hershey’s MrBeast problem (1:28:15) Marketing and social signaling in CPG products (1:30:47) AgEagle Aerial Systems: $4B market cap, zero revenue (1:34:50) The most ridiculous SPACs (1:41:06) How Edwin differentiates his research (1:47:07) Favorite short sellers (1:47:59) Companies that will lose to AI (01:49:29) Why creator-led business will steal share from incumbents

The Peel with Turner Novak – Details, episodes & analysis

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The Peel with Turner Novak – Details, episodes & analysis

Podcast details

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