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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
Charley Ma and Mahdi Raza are the Co-founders of Pathlight Ventures, and were early employees at five unicorns, Plaid, Ramp, Alloy, Robinhood, and Stytch.
They share tactical advice for early stage startup employees, lessons getting Plaid and Ramp their first customers, and deciding to build Pathlight together.
Timestamps
(00:00) Intro
(02:30) Growing up in basements
(05:15) Charley’s journey to first biz hire at Plaid
(15:01) Advice on being a good startup employee
(19:34) Mahdi’s path to Robinhood
(26:33) Deciding between joining an early or late stage startup
(32:39) Why Charley joined Plaid despite VCs telling him not to
(38:52) Benefits of case studies in hiring
(39:58) Why every hyper growth company is a shit show
(44:24) Startup comp: equity, QSBS, early exercise, vesting
(49:59) Joining Ramp as the first Head of Growth
(58:35) How Ramp got its first customers
(01:02:06) Advice and common traps on early GTM strategies
(01:05:04) Why $1M ARR does not mean you have PMF
(01:06:51) Meeting when Robinhood bought, churned, then returned to Plaid
(01:09:54) Deciding to build Pathlight together
(01:23:06) Raising Fund 1 in 2021 and how bad timing almost killed it
(01:29:55) Reasons founders work with Pathlight
(01:32:04) Why most investors add no value and give bad advice
(01:36:44) Founders Pathlight invests in + Artie case study
(01:44:44) Competing with incumbent funds
(01:53:57) Raising a $75m Fund 2 in 2023
(02:02:22) Are Seed extensions good investments?
(02:07:45) Discussing startup valuations
(02:09:09) Mahdi’s 10-minute market outlook (as of 8/8/24)
Referenced
https://www.pathlight.vc/
https://plaid.com/
https://robinhood.com/us/en/
https://ramp.com/
https://stytch.com/
https://www.alloy.com/
https://www.artie.com/
Follow Charley
Twitter: https://twitter.com/charleyma
LinkedIn: https://www.linkedin.com/in/charleyma
Follow Mahdi
Twitter: https://twitter.com/mahdirazamr
LinkedIn: https://www.linkedin.com/in/mahdirazany
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it/
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.
He’s had six near death experiences, and we talk about how those influenced him throughout life. We also talk about some of his early businesses, including one that had the FBI at his house when he was a kid, and lessons driving the monorail at Disney.
We also get into the founding story of ClickUp, bootstrapping to $10m in ARR, hiring mistakes from scaling too fast, why Zeb likes hiring users, how ClickUp shipped generative AI features so fast, its new chat product launched earlier this week, and the trend of software convergence.
Timestamps:
(00:00) Intro
(02:11) Zeb’s first near death experience
(08:19) Childhood businesses that had the FBI at his house
(18:23) Lessons from driving the monorail at Disney
(25:19) Mistakes scaling from 100 to 800 employees in one year
(31:04) Dropping out of college after being robbed at gunpoint
(33:19) How building a CraigsList competitor led to ClickUp
(35:32) Three waves of ClickUp’s product evolution
(39:25) How the product slowly got worse over time
(44:45) Hiring the guy who built Microsoft Teams to rebuild ClickUp
(48:11) Zeb’s favorite interview question
(49:59) Daily 5am standups in the first year
(54:28) How ClickUp got its first customers
(57:16) Bootstrapping to $10m in ARR with strong retention
(58:13) Zeb’s best kept secret, user surveys (and how to run them)
(1:02:42) The trend of software convergence
(1:08:26) Reasons Zeb likes hiring users
(1:12:19) Why VCs didn’t invest, and why it led to a better business
(1:19:02) Raising from Craft, Georgian, and a16z
(1:21:08) Peter Thiel: “I think you’re right”
(1:24:35) How ClickUp was early to AI
(1:28:03) Launching chat and video calls to hit ClickUp's original vision
(1:32:02) What Zeb’s excited and cautious about in AI
(1:37:24) Why Zeb journals every day
Referenced:
ClickUp: https://www.clickup.com
ClickUp’s new chat feature: https://clickup.com/features/chat
Follow Zeb
Twitter: https://x.com/dj_curfew
LinkedIn: https://www.linkedin.com/in/zebevansclickup
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it/
Bobby DeSimone is the Founder and CEO of Pomerium, the best way to authenticate, authorize, monitor, and secure user access to any application without a VPN.
Bobby explains why access control is so important, how it led to the biggest corporate hack ever, how its related to the day CrowdStrike took down the global economy, and how AI will change security.
Pomerium has a unique open source approach, and Bobby takes us inside the early days of building the product, how he got the first customers, lessons learning enterprise sales as a technical founder, and inside his funding rounds, including a recent Series A led by Eric Vishria at Benchmark.
Timestamps
(00:00) Intro
(02:02) Access Control: a sneaky large problem
(07:22) How an unsecure air conditioner led to the biggest credit card breach in history
(10:23) Google’s internal security software inspiring Pomerium
(16:41) Making his first money online selling a WoW bot
(19:24) How CrowdStrike took down the global economy in July, 2024
(22:29) Deep dive on access control and security
(29:39) How access controls impacted Google vs Uber’s self-driving lawsuit
(30:52) Why Zero Trust security is marketing bullshit
(32:09) Advice for building access control
(34:39) How open source built early trust with customers
(41:39) Missing a 7-figure deal because he didn’t use LinkedIn
(44:52) Everything he’s learned about sales as a technical founder
(50:06) Inside Pomerium’s Series A
(51:41) Advice on evaluating potential investors
(56:06) How AI will change security
(01:01:15) Getting in trouble at the first Pomerium board meeting
(01:02:15) How to hire good engineers
(01:04:00) When to scale back IC work as a founder
(01:06:56) Favorite new AI tools
(01:11:09) Why Meta’s open sourcing its AI models
(01:12:32) Life lessons from Charlie Munger
Referenced
Check out Pomerium: https://www.pomerium.com/
Crowdstrike outage post-mortem: https://www.crowdstrike.com/falcon-content-update-remediation-and-guidance-hub/
Pomerium on GitHub: https://github.com/pomerium/pomerium
Follow Bobby
Twitter: https://x.com/bdd_io
LinkedIn: https://www.linkedin.com/in/bobby-desimone/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it/
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
Referenced
The Power of Investor Updates: https://mail.bigdeskenergy.com/p/power-investor-updates
beehiiv’s old investor updates: https://mail.bigdeskenergy.com/c/beehiiv-investor-journey
The BDE Spotify Playlist: https://open.spotify.com/playlist/5s8443tfYUq3LLARJwGeYP
Where to find Tyler
Twitter: https://twitter.com/denk_tweets
LinkedIn: https://www.linkedin.com/in/tyler-denk
Newsletter: https://mail.bigdeskenergy.com
Where to find Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it
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: https://www.linkedin.com/pulse/fog-ai-what-investors-missing-part-three-michelle-valentine Superintelligence: https://www.amazon.com/Superintelligence-Dangers-Strategies-Nick-Bostrom/dp/1501227742
Where to find Michelle: Twitter: https://twitter.com/_vltn LinkedIn: https://www.linkedin.com/in/michellevalentinehk/
Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
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
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 https://docs.google.com/presentation/d/1T3kGf-n4cmd6_UqOQNb79ZXFL723b9HdZyTnk9sLOlM/edit
Where to find Logan: Twitter: https://x.com/loganbartlett LinkedIn: https://www.linkedin.com/in/loganbartlett/
Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
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: https://www.thespl.it/
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/
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
More on Car Dealership Guy: https://www.dealershipguy.com/
Referenced Who the F*ck is Car Dealership Guy: https://www.youtube.com/watch?v=_wTsAez_nMs Russ Flips Whips: https://russ.dealershipguy.com/ Freight Waves’ Craig Fuller on The Peel: https://youtu.be/oPPqO8eBq2M Epic Gardening’s Kevin Espiritu on The Peel: https://youtu.be/FefGL-qPzDo
Where to find Yossi: Twitter: https://twitter.com/GuyDealership YouTube: https://www.youtube.com/@CarDealershipGuy
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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