The Peel with 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

Referenced

Where to find Michelle:

Where to find Turner:

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.

Referenced:

Where to find Logan:

Where to find Turner:

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:

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

Where to find Ryan:

Where to find Turner:

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:

More on Car Dealership Guy: ⁠https://www.dealershipguy.com/

Referenced

Where to find Yossi:

Where to find Turner: