Stay ConnectedExploring 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.
Copyright: © Turner Novak
Daryna Kulya is the Co-founder of OpenPhone, the world’s best business phone
This episode is a masterclass on startup marketing, chronicling the first six years of OpenPhone, how they acquired their first customers, and inside all the different channels they used to scale the business to over 100k customers, including FB Groups, Reddit, SEO, cold outbound.
We also get into why founder-led content is so important today, and why design is a crucial core competency.
For full show notes, visit: https://highlightai.com/share/28b95226-9936-4ae9-882d-6c68a1b578d5
Timestamps:
(00:00) Intro
(02:10) OpenPhone’s new API launch
(06:41) Why a better business phone is a big deal
(13:18) Immigrating from Ukraine to the US and building OpenPhone
(15:39) Hacking a custom business phone
(25:29) How OpenPhone got its first customers from Facebook Groups
(33:02) Tricks for unlocking word of mouth
(39:11) Transitioning from free to paid users
(43:05) How OpenPhone cracked word of mouth on Reddit
(46:29) OpenPhone’s YC experience
(49:01) Why the Seed round was hard to raise
(53:49) Using Slack to aggregate all customer feedback across the internet
(57:38) How YC helped redefine their ICP
(01:01:33) Tactics for sending cold emails
(01:06:24) How to get and benefit from press
(01:12:18) Daryna’s “behind the scenes” approach to founder-led content
(01:16:26) Using long-tail keywords to kickstart an SEO strategy in 2020
(01:23:05) When to do founder-led content vs SEO
(01:28:38) How your customers should pull you up-market
(01:30:18) Why OpenPhone cares about design
Referenced:
OpenPhone:
Ahrefs:
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Lisa Rapuano outperformed the market 15 years in a row in the 90’s and 2000’s. We go deep on how she did it, including early investments in AOL, Dell, and owning 24% of Amazon in 2002.
She shares what she learned from Jeff Bezos and Michael Dell, what makes a good investor, plus her experience as a startup CFO and how it influenced how she thinks about investing.
For full show notes, visit: https://highlightai.com/share/883f2cc9-9771-4331-9a42-6ae236f50344
Timestamps: (00:00) Intro (03:18) Growing up middle class while dad worked at NASA (12:31) Moving to Baltimore to work for Bill Miller (18:12) What Lisa learned from Bill (19:41) How value investing changed over the last 30 years (26:40) Investing in internet stocks in the 90’s and 00’s (29:50) Thinking a 13x win on AOL in 1996 would be the biggest of her career (37:33) Teaching Barry Diller about the internet (41:30) How Dell reinvented PC manufacturing and created a negative cash conversion cycle (46:46) How Amazon survived the Dot Com Crash (51:53) Buying 24% of Amazon in 2002 (53:15) Why companies get the investors they deserve (57:22) What Lisa learned from Jeff Bezos (1:04:31) Lessons from raising too much money (1:07:57) Running her own fund from 2006-2016 (1:13:32) Why fees in asset management are too high (1:15:20) Joining Facet out of retirement 2017 (1:20:20) What she learned about investing from operating (1:23:47) Why women are better investors than men (1:26:43) How to hire outlier candidates (1:35:06) Why no one can be the next Warren Buffett (1:39:54) When to sell your winners
Follow Lisa:
LinkedIn: https://www.linkedin.com/in/lisa-rapuano/
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/
Gokul Rajaram is an early stage technology investor. As a product leader, operator and board member, he’s helped build seven generational technology companies, including Alphabet, Block, Coinbase, DoorDash, Meta, Pinterest, and The Trade Desk.
We talk about lessons learned from Zuck, Sergey Brin, and Jack Dorsey, when big acquisitions can go well, how to define your ICP, why you should always size markets bottoms-up, having a fast response time, how seed investing has changed since 2007, and Gokul’s hot takes on titles at a startup.
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.
Timestamps:
(00:00) Intro
(02:14) Common thread of success between the founders of Google, DoorDash, Facebook, and Square
(05:50) Gokul’s first job in Silicon Valley
(07:46) How Serendipity led to PMing Adsense, one of Google’s biggest products
(12:20) Lesson from Sergey Brin on reducing friction before a products magic moment
(18:50) How Zuck used founder mode to beat Google Plus in 2011
(22:51) When big acquisitions can go well
(24:47) How Gokul switches from startup helper to public company board member
(28:09) The evolution of Seed investing since 2007
(33:27) How to have a fast response time
(37:40) Lessons from Jack Dorsey always selling
(39:54) How to define your ICP
(42:40) Using bottoms-up to size a market
(44:05) Why Director and VP titles are bad for startups
Referenced:
Who’s Got the Monkey? https://hbr.org/1999/11/management-time-whos-got-the-monkey
Getting Things Done: The Art of Stress-Free Productivity https://www.amazon.com/Getting-Things-Done-Stress-Free-Productivity/dp/0142000280
How to Size a Market in 30 Minutes https://blog.blingcap.com/2023/02/13/How-to-Size-a-Market/
Follow Gokul:
Twitter: https://x.com/gokulr
LinkedIn: https://www.linkedin.com/in/gokulrajaram1
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/
Guy Podjarny is the founder of Blaze, Snyk, and now Tessl. He’s spent decades building at the center of developers and security. His newest company Tessl is reimagining software development, helping shape a new paradigm he calls AI Native Development.
We talk through his four quadrant framework for building and investing in AI, plus go into the early days of Blaze and Snyk. He shares lessons on marketing to developers, hiring when no one wanted to work for him, overcoming multiple difficult funding rounds, and lessons from multiple M&A processes.
Timestamps:
(00:00) Intro
(02:21) The four quadrants of building and investing in AI
(14:59) Why AI startups are riskier than non-AI startups
(19:42) When to sell your company vs keep building
(24:57) Why hiring the early team is so hard
(26:32) Early marketing tricks from Guy’s first company, Blaze
(29:09) Strategies for using conferences to grow your brand
(33:33) Getting three days of free PR
(38:04) Moving to Ottawa
(42:11) Why Sales Engineer is an underrated founder stepping stone
(45:49) What he learned as CTO of Akamai
(48:31) Starting his third company Tessel, and why there’s no satisfaction without struggle
(50:41) How Snyk got started
(54:10) Creating developer-first security
(59:59) Secrets for developer marketing
(01:02:31) Why podcasts work so well for marketing
(01:06:26) Snyk’s failed Series A
Referenced
Tessl: https://tessl.io/
Snyk: https://snyk.io/
Charting Your AI Native Journey: https://www.tessl.io/blog/charting-your-ai-native-journey
Secure Developer Podcast: https://snyk.io/podcasts/the-secure-developer/
AI Native Dev Podcast: https://www.tessl.io/podcast
We didn’t mention it in the podcast, but Guy just announced the AI Native Dev Conference, a virtual conference on Thurs, November 21st. Join him + many others here https://ai-native-devcon.heysummit.com/
Follow Guy
Twitter: https://x.com/guypod
LinkedIn: https://uk.linkedin.com/in/guypo
Follow Turner
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LinkedIn: https://www.linkedin.com/in/turnernovak
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Chris Hladczuk is the Co-founder and CEO of Hanover, where he’s building 1-click migration and 1-minute time to value fund administration for the $8 trillion in private market assets.
Chris takes us through his story of building an audience online at nights while working at Goldman, breaking into tech and going from an IC to Chief Revenue Officer at a Series A startup in nine months.
This episode is packed with advice on sales, getting your first startup role, and everything he’s up to at Hanover.
Timestamps
(00:00) Intro
(02:11) Why B2B SaaS is dead
(07:20) Competing against companies that have “IT departments”
(11:37) Going from 0 to 100k on Twitter in one year
(19:06) The ASS networking framework
(25:17) Interviewing at 50 startups before quitting Goldman to join Meow
(28:41) Lessons going from sales IC to Chief Revenue Officer in nine months
(32:47) Using SSS to send good cold emails
(35:51) Learnings as a first-time manager
(40:46) How to make a good first impression
(47:22) Why sales and copywriting are underrated
(49:17) Navigating the startup idea maze to fund admin
(56:47) 1-click fund admin migration, 1-minute time to value
(59:46) Turning down Hanover’s first term sheet with no backup plan
(01:03:28) Using polite persistence to get customers
(01:08:41) Why the best companies are cults
(01:11:01) John D Rockefeller and vertical integration
(01:13:26) Doing culture fit questions at the beginning of the hiring process
(01:15:34) Chris’ favorite AI tools
(01:17:58) How to make founder-led content
Referenced
Check out Hanover: https://www.hanover.co/
Brick: https://getbrick.app/
Alex Hormozi’s Sales Podcast: https://open.spotify.com/show/6YNopzKDGDwf0auIpPTIID
Sweetgreen: https://www.sweetgreen.com/
Chipotle: https://www.chipotle.com/
Eight Sleep: https://www.eightsleep.com/
Turner’s episode with Jonathan Neman at Sweetgreen: https://open.spotify.com/episode/1Emm6VOq6MCEfQlXv05q6U?si=hJMc8LhBTeeonYJGza4gxQ
The Hanover Manifesto: https://www.hanover.co/manifesto
Claude Sonet: https://claude.ai/
Cursor: https://www.cursor.com/
Hemingway Editor: https://www.hemingwayapp.com
Follow Chris
Twitter: https://twitter.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
Newsletter: https://www.thespl.it/
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
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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/
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.
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.
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
Referenced The Bear Cave: https://thebearcave.substack.com/ FOIA Request Template (#13 here): https://www.readideabrunch.com/p/our-2023-hedge-fund-analyst-christmas SEC Full Text Search: https://www.sec.gov/edgar/search/ WSJ’s Care.com Story: https://www.wsj.com/articles/care-com-puts-onus-on-families-to-check-caregivers-backgroundswith-sometimes-tragic-outcomes-11552088138 Planet Fitness CEO resignation letter: https://x.com/StockJabber/status/1762220603715596460 Aurelius Value: https://x.com/AureliusValue Big River Capital: https://x.com/BigRiverCapita1 Marc Cahodes: https://x.com/AlderLaneEggs David Orr: https://x.com/orrdavid Citron Research: https://x.com/CitronResearch
Where to find Edwin: Twitter: https://twitter.com/StockJabber LinkedIn: https://www.linkedin.com/in/edwin-dorsey-a9195273/
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://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 https://brave.com/ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign.
Lisa Wehden is the Founder and CEO of Plymouth Street, making fast and simple immigration for technologists. We go deep on the broken US immigration system, how its holding back US innovation, and the secret 0-1A Visa you can get in as fast as four weeks.
Lisa lived in a sawmill while building her first climate tech startup, and we go inside that journey, giving the VC money she raised back to start Plymouth, raising grants to fund it, and how she broke into Silicon Valley as an outsider.
Timestamps:
(00:00) Intro (04:51) The state of US immigration (09:26) Why immigrants are good founders (11:43) The secret O-1A Visa (12:18) Why the O-1A is easier to get (16:54) Founders that have gotten their O-1A (20:00) Getting a Visa in four weeks with Plymouth (22:01) The 500-page, physical paper Visa application (25:57) Lisa’s US immigration COVID hobby (27:58) Living in a Sawmill building a climate tech startup (30:59) Giving VCs their money back (32:19) Joining Interact in SF (33:51) Raising grant money instead of VC (34:40) Becoming a paralegal to learn the industry (37:24) The Plymouth 100 community (39:20) How Lisa raised grant funding from Eric Schmidt and Tyler Cowen (43:55) Talent is the bottleneck to AI development (46:04) How to break into Silicon Valley as an outsider (52:43) Hiring on hopes and fears (55:31) "Write it down, make it happen" (56:45) Benefits of doing a calendar audit (1:01:54) Anyone can be an entrepreneur (1:04:53) Why Lisa doesn’t work from her phone (1:06:38) How to fix the US immigration system
More on Plymouth Street: https://www.plymouthstreet.com/
Referenced:
Interact: https://joininteract.com
Lisa’s 0-1 Visa Guide: https://lisa-wehden.medium.com/a-guide-to-applying-for-the-o-1-visa-for-extraordinary-individuals-8ca5f22ff86b
Writing a forwardable email intro: https://also.roybahat.com/introductions-and-the-forward-intro-email-14e2827716a1
Where to find Lisa:
Twitter: https://twitter.com/lisawehden
LinkedIn: https://www.linkedin.com/in/lisa-wehden-aa111385/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel 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. Melissa Cash is the Co-founder and CEO of Pok Pok, a montessori-inspired collection of digital toys that spark creativity and learning through open-ended play. Prior to Pok Pok, Melissa spent a decade working in marketing and design roles, helping Snowman drive 9-digits of downloads across its game portfolio and designing physical products at Disney. Timestamps: (00:00) Intro (05:46) Creating a Montessori inspired game (12:18) Why it's impossible to avoid screen time (15:35) Designing a non-addictive product (17:38) Monetizing a non-addictive game (21:47) How to price a subscription game (24:18) Using new features to drive retention (26:04) Marketing a kids game to parents (30:59) Why Pok Pok waited to launch Android (34:12) How getting pickpocketed in Germany led to a job designing products at Disney (39:23) How great products can define a childhood (43:21) Lessons from having a great idea while working at Disney (46:03) First coming up with the idea for Pok Pok (49:00) Advice for starting your first company (50:10) Fundraising tactics from Pre-Seed to Series A (54:08) How to build your network from zero (57:08) Getting the most out of Slack groups (59:07) Melissa’s hack for in-person events (01:01:33) Tactics for meeting people at events (01:03:39) Winning multiple Apple design awards (01:07:07) How to get press for your startup (01:13:17) Prioritizing getting women on Pok Pok’s cap table (01:18:38) Strategies for staying creative (01:21:58) Melissa’s influencer marketing hacks (01:24:24) Lessons from failed influencer campaigns (01:28:19) Growing 5x YoY, adding STEM content (01:30:28) What surprised her about starting a company Referenced: Try Pok Pok for 50% off an annual subscription with code POKPOK50: https://apple.co/3XAGSwT Snowman Studios: https://www.builtbysnowman.com/ Hampton Private Founder Group: https://joinhampton.com/ VC Backed Mom’s: https://www.vcbackedmoms.com/ The Peel Podcast episode with Eric Newcomer: https://www.youtube.com/watch?v=HXH_peQWtnc More on Pok Pok’s Series A: https://techcrunch.com/2024/06/18/now-a-series-a-startup-kids-app-and-digital-toy-pok-pok-is-coming-to-android/
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel
Ed Sim is the Founder of boldstart ventures, which partners with bold founders reinventing the enterprise stack at the inception stage. Ed takes us inside the journey building boldstart, from its first $1m fund in 2010 up to $850m in AUM today.
Timestamps: (00:00) Intro (03:48) Evolution of early stage investing(05:11) Inception stage investing (10:32) Backing bold founders reinventing the enterprise stack(11:20) Repeatable ways to build enterprise businesses (12:04) The 5 P’s of early stage investing (14:12) Backing Guy Podjarny and Snyk (18:18) Knowing when to follow-on (19:18) The 3 Ch's of a good board member (22:01) How Ed’s board role changes over time (24:20) Balancing founder friendly with returns (27:20) How to build customer relationships (30:24) Advice for closing customers (33:47) Creating the Seed category in 2009/10 (37:31) boldstart’s $1m Fund 1 (39:00) Why Ed didn’t join a large firm in 2012 (39:55) boldstart’s $16.5m Fund 2 (40:26) Why LPs passed on the first funds (43:11) Leading rounds in Kustomer, Snyk, BigID, and Blockdaemon in Fund 3 (47:09) Why $112m Fund 4 was the hardest to raise(50:52) Ed’s approach to LP fundraising (55:12) Inside Meta’s acquisition of Kustomer and sale back to the founders (59:52) Backing Rahul from Superhuman a 2nd time (01:00:52) The different GTM playbooks (01:02:20) Importance of contract size and time to close (01:05:07) Why AI makes security more important (01:06:11) When to switch from founder-led sales(01:07:46) Backing ProtectAI after a conference (01:08:28) Balancing between inbound and outbound sales (01:09:55) Winners and losers in AI (01:15:26) Building the boldstart team (01:25:19) Lessons being an interim CEO (01:27:15) How ZIRP pulled revenue forward (01:29:08) The death of high growth software (01:32:58) Identifying startup opportunities incumbents won’t crush (01:35:00) Second order effects of AI (01:36:46) Using "Intuitive TAM" to size new markets (01:38:04) Investing before there’s a market map (01:38:57) Balancing family, fitness, and career
Referenced:
https://boldstart.vc/
Turning Down HBS: https://x.com/edsim/status/1315644287007240193
Ed’s tweet on raising Fund 4: https://x.com/edsim/status/1315644287007240193
Second Order Effects of AI: https://www.whatshotit.vc/p/whats-in-enterprise-itvc-379
Death of Hyper Growth: https://x.com/edsim/status/1797613384994623808
Where to find Ed:
Twitter: https://twitter.com/edsim
LinkedIn: https://www.linkedin.com/in/edsim/
Newsletter: https://www.whatshotit.vc/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel
Nilam Ganenthiran is the founder and CEO of Beacon Software. Previously, he was the 12th employee and President at Instacart.
We talk tactics for customer research, building customer relationships, balancing strategy and execution, how to serve on and manage a board, what happened when Amazon bought Instacart’s biggest customer Whole Foods, inside its COVID response, surviving eight months of runway in 2015, his new company Beacon Software, and more.
Timestamps:
(00:00) Intro (04:23) Inside Amazon acquiring Instacart’s biggest customer, Whole Foods (12:13) Lessons from quickly signing 8 of the top 10 grocers (13:06) Why grocers were slow to adopt ecommerce (15:29) Building “Shopify for grocers” (16:22) Sales = building relationships (19:05) Why Wegman’s is one of the best grocers in the world (20:43) Cold calling Wegman’s and signing them two years later (24:33) How to do customer research (26:59) Catching an Uber in suits on the highway (28:50) Why Instacart was possible back in 2013 (30:36) Launching Instacart’s advertising network (38:46) Growing 5x in 5 weeks during COVID (45:20) How Nilam started angel investing (47:56) Advice for sitting on boards (50:00) The roles and incentives of a board member (54:03) Deciding when to keep going and when to give up (56:02) Nilam’s framework around optionality (59:17) Seven years of weekly redeye flights (1:00:30) Almost running out of money 8 months after Instacart’s Series C (1:07:54) Why time is your scarcest resource & startups are default dead (1:10:00) Nilam’s new company, Beacon Software (1:11:28) Why he’s excited about AI (1:13:25) How AI makes human relationships more important (1:14:41) Turner’s investing lessons from family members
Beacon Software: https://beaconsoftware.ca/
Where to find Nilam:
Twitter: https://twitter.com/nilamg
LinkedIn: https://www.linkedin.com/in/nilamganenthiran/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel
Ankur Goyal is the Founder and CEO of Braintrust, the end to end developer platform for building the world's best AI products. Their customers include companies like Instacart, Zapier, Notion, Airtable, Replit, and more.
We hit on the importance of LLM evals, advice for building AI products, why the best companies have two AI product roadmaps, and his non-conventional advice for founders.
Timestamps:
(00:00) Intro (04:04) Why everyone’s now an AI company (06:03) Reasons LLM evals are so important (08:10) Typescript becoming the language of AI (09:19) Replacing vibe checks with Braintrust (10:37) Making OpenAI’s protocols the standard (11:27) Why the best companies have two AI roadmaps (13:06) Building your product so each LLM release makes it better (14:54) Predicting AGI is impossible (15:54) Why people who work with LLMs aren’t worried about AI safety (16:52) The best developers are all-in on co-pilots (18:11) How AI is changing software development (21:09) Combining IDE, CIDC, and observability in one product (27:18) Are models more like CPU’s or relational databases? (30:14) How to pick an LLM (33:00) Advice for staying on top of new AI developments (34:30) Why tool calling is so important (38:02) Advice for young software engineers (40:25) Learning to code doing linear algebra homework (42:36) Lack of purpose interning in big tech (44:07) Working at MemSQL learning to be a founder (47:52) How to get a job at a startup (50:43) Building his first startups product on an international flight (52:39) Three lessons from his first failed startup (54:46) Don’t delegate what you’re good at (55:46) Why you should be careful listening to VCs advice (57:34) Tactics for successful delegation (59:36) Why Ankur doesn’t do any meetings (01:02:42) The importance of self-service in unlocking certain customer segments (01:05:14) How Braintrust got started (01:07:45) Advice on picking your target customers (01:10:35) How Braintrust hires with work trials (01:15:21) Balancing security with a modern UI (01:17:49) Why it’s hard to sell non-AI products right now (01:19:21) Advice for selling to large enterprises (01:23:10) Ankur’s favorite AI products
Referenced:
https://www.braintrustdata.com/
SICP Book
PDF: https://web.mit.edu/6.001/6.037/sicp.pdf
Hardcopy: https://www.amazon.com/Structure-Interpretation-Computer-Programs-Engineering/dp/0262510871
Linear’s guide to work trials: https://linear.app/blog/why-and-how-we-do-work-trials-at-linear
Where to find Ankur:
Twitter: https://twitter.com/ankrgyl
LinkedIn: https://www.linkedin.com/in/ankrgyl/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeelAlan
Feld is the Founder and Managing Partner of Vintage Investment Partners. Vintage is one of the largest fund of funds in the world, managing over $4 billion across what is mostly investments into other venture funds, plus some secondary and direct startup investments at the growth stage.
Timestamps:
00:00 Intro 03:53 What is Vintage 05:40 Why VCs adding value can waste a founder’s time 09:01 VC, where the asset chooses the investor 10:14 Fund size is the enemy of returns in VC 14:57 What people get wrong about FoFs 16:01 The value FoFs bring to LPs 17:11 Why entrepreneurs drive VC returns 17:55 Vintage’s unique FoF model 19:05 Does replacing the founders with an outside CEO work? 21:39 Starting Vintage after the Dot Com Crash in 2002 23:41 Buying secondaries at 70-80% discounts 25:13 Biggest mistakes when buying secondaries 26:18 Research around what makes the best entrepreneurs 31:09 Lessons from six downturns 34:41 Comparisons between 2002 and 2022 37:07 Advice for raising your first VC fund 41:16 The importance of differentiation 45:57 Sustainable ways to differentiate 49:05 What Vintage looks for in new fund investments 49:57 Advice for scaling a VC firm 53:47 Succession planning 57:50 What Alan’s doing post-Vintage
Vintage Investment Partners: https://www.vintage-ip.com/
Where to find Alan:
Twitter: https://twitter.com/alanf_feld
LinkedIn: https://www.linkedin.com/in/alan-feld-1744389/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel
Anu Sharma is the Co-founder and CEO of Millie, building a better care system from the inside out. Our conversation covers the existing maternal health system, how Millie is reinventing it, and how to succeed building a healthcare company.
Timestamps: (00:00) Intro (03:16) Problems in US maternity care (13:21) Why insurance reimbursement drives healthcare (16:11) How bundled care unlocks personalization (18:48) From fiction writer to 20 years in healthcare (24:22) Why consumers don’t act like consumers in healthcare (26:09) The reason scale matters (27:43) Bundled payments and new care design (32:16) What make Millie unique (35:58) Importance of picking regional markets in healthcare (37:08) The two paths for insurance reimbursement (41:08) Why distribution is the product in healthcare (44:25) Opportunities in cash pay care (48:28) How Anu fundraised without a product (51:06) The future of in-person, hybrid, and virtual healthcare (52:56) Building maternity clinics for $150k
Check out Millie: https://www.millieclinic.com/
Where to find Anu: Twitter: https://twitter.com/anu_anusharma1 LinkedIn: https://www.linkedin.com/in/anu-sharma-b169b12
Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel
Aaron Levie is a co-founder and the CEO of Box. This conversation covers opportunities in AI, the early days of Box, and lessons Aaron's learned on his founder journey.
Timestamps (00:00) Intro (03:11) Why ChatGPT was an iPhone moment (04:37) Advice for large companies incorporating AI (11:16) Why AI will add jobs, not steal them (16:13) How AI is supercharging Box’s products (19:03) AI agents: the $1 trillion opportunity (25:27)Estimating size of new markets(29:58) Starting Box with high school friends (33:18) Living out of their first office (34:52) Why early investors passed on Box (37:24) Pivoting from consumer to B2B (39:53) How Box got its first customers (41:57) Should founders talk to Associates at VC firms? (43:26) How Mamoon at Kleiner saved Box at its Series B (46:25) Turning down an acquisition before IPO (50:51) Why Box’s IPO was so hard (54:11) Fending off an activist investor during COVID
Check out Box: https://www.box.com/
Where to find Aaron:
Twitter: https://twitter.com/levie
LinkedIn: https://www.linkedin.com/in/boxaaron/
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://joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll. Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Elad Gil is the founder of Color Genomics and Mixer Labs, which he sold to Twitter, and an early investor in iconic companies like Airbnb and Stripe, plus upstarts like Perplexity and Anduril. This is a wide ranging conversation that covers education, AI, and advice for building a startup. Timestamps (00:00) Intro (03:46) Building cool monuments (09:12) Fixing education (16:38) Why AI is underhyped (19:02) Four trends to watch in AI (19:55) Why there aren’t large biotech companies (23:21) The current state of Elad Gill (24:32) How he incubates companies (26:32) Contemplating AI-driven buyouts (27:29) His investing strategy, from early to late stage (36:57) Why he remained solo for so long (40:19) How to get conviction in unpopular investments (42:53) What made Steve Jobs a good communicator (44:00) The importance of ambition and leadership (46:28) Why Elad puts so much weight in the market (47:45) The evolution of Google’s business model (49:17) How to monetize consumer products (50:06) Analyzing a potential startup market (51:23) How successful products eventually become distribution companies (56:30) Non-obvious startup advice (59:54) When its OK to give up (01:02:20) Advice on raising your first round (01:03:21) Picking board members (01:04:45) How to hire your first three employees (01:06:48) Avoiding bad hires (01:08:39) The importance of speed of execution (01:12:36) Why he’s adding to his team (01:14:31) Gardening Referenced: Elad’s Blog: https://blog.eladgil.com/ Elad’s Podcast: https://www.youtube.com/@NoPriorsPodcast/ Elad’s Book: https://growth.eladgil.com/ Where to find Elad: Twitter: https://twitter.com/eladgil LinkedIn: https://www.linkedin.com/in/eladgil Elad’s Website: https://eladgil.com/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
This episode is brought to you by Warp. Don’t let payroll and compliance hold your startup back: visit https://joinwarp.com/peel to get started and receive a $1000 gift card when you first run payroll.
Celine Halioua is the founder and CEO of Loyal, a biotech company developing medicine to help dogs live longer and healthier lives. And dogs are just the start - Celine thinks Loyal could one day do the same for humans.
She takes us inside what it’s like to build a biotech company from scratch. We talk through how Loyal’s longevity drugs work, the process of getting FDA approval, her biggest mistakes as a founder, how to approach building in a new market, lessons learned failing to raise her Series B, why rate of growth is all that matters in hiring, and almost not starting the company in the first place.
Timestamps: (00:00) Preview (03:30) How a longevity drug works (06:08) Predictions around longevity (08:26) Why Celine cares so much about not failing (12:05) Differences between biotech and software startups (14:15) Sizing a new market (16:53) Why biotech startups are more dilutive early on (20:22) Getting FDA approval (22:57) Why its hard to prove longevity drugs actually work (24:48) The reason Loyal started with dogs (25:27) How Loyal’s drug slows aging (33:42) Working on longevity to increase free will (34:25) Culture shock at Oxford and dropping out of her PhD (37:22) What makes Josh Koppelman a good VC (39:44) Celine’s two biggest mistakes as a founder (42:39) Why rate of growth is the best indicator of success but the hardest to predict (45:33) Self awareness & how being a CEO is both fun and miserable (48:11) How Laura Deming convinced her to start Loyal (50:18) Finding the science behind Loyal (54:21) Deciding it was the right path to start a company (56:30) Lessons from failing to raise a Series B initially (1:02:18) Why Silicon Valley can build 10x more deep tech startups (1:04:05) Doing big things that improve the world (1:04:50) What Celine looks for in startups Where to find Celine:
Twitter: https://twitter.com/celinehalioua
LinkedIn: https://www.linkedin.com/in/celinehh/
Celine's Website: https://www.celinehh.com/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Rahul Sonwalkar is the founder and CEO of Julius, an AI data scientist. He takes us inside his epic “Ligma Johnson” prank where he pretended to be fired from Twitter the day Elon acquired the company. He then goes inside his journey of building Julius, sharing lessons learned along the way and his vision for the product. Timestamps: (00:00) Preview
(04:16) The "Ligma Johnson" prank
(09:02) Meeting Elon
(13:10) Doing hackathons in college
(14:30) Scraping emails from Hacker News to get internships
(16:25) Using Twitter to learn and meet people
(22:26) Lessons from his first failed startup
(26:19) Taking too long to quit Big Tech & his failed startup idea in trucking
(32:12) Convincing Guillermo Rauch to invest with speed of execution
(34:48) How to avoid analysis paralysis
(36:15) Building Julius, the AI data scientist
(39:25) How COO of a hot tub company uses Julius
(40:40) Professor embracing AI, using Julius to teach his class
(42:47) Iterating on early versions of the product
(44:42) PMF is as much about the market as the product
(45:08) Building dozens of ChatGPT plugins to acquire Julius’ first users
(45:41) Using dev API keys and missing the first paying customers
(49:22) Talking to hundreds of early customers
(50:10) Why customers love when you ship new features every week
(52:14) The power of Julius’ small team
(54:38) Why Rahul gives his number to customers
(57:47) How to avoid idea backlogs
(59:27) Why Julius tests so many models
(01:01:44) Why it feels great when people love your product
(01:03:43) AI will write more code than humans
(01:06:33) Giving an AI a computer
(01:11:05) What happens to all the AI startups?
(01:12:36) Why you have to Ride the Tiger
(01:16:43) How NVIDIA beat 89 other graphics card startups
(01:20:14) Building a moat as a startup
(01:22:50) Rahul’s favorite AI companies
(01:25:11) Why Julius’ changes UI components based on the use case
(01:27:42) Benefits of lifting
(01:29:54) Why Rahul loves SF
(01:31:38) The early days of Microsoft
Referenced: https://julius.ai/ Guillermo’s tweet: https://x.com/rauchg/status/1773168477957919055 Where to find Rahul: Twitter: https://twitter.com/0interestrates LinkedIn: https://www.linkedin.com/in/rahulsonwalkar23 Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
Brought to you by Attio, the next generation of CRM: https://bit.ly/AttioThePeel
Bill Shufelt is the Founder and CEO of Athletic Brewing, the craft brewer that created the non-alcohol beer market in the US.
Bill takes us inside the early days of starting the company, including realizing there was an opportunity to make non-alcoholic beer, finding a co-founder, struggling to find early investors, building multiple breweries, and getting into Whole Foods before launching. Our conversation is a case study on creating a new market - I hope you enjoy.
Timestamps:
(00:00) Preview
(04:10) Becoming the #1 beer in Whole Foods
(05:54) The history of non-alcoholic beer
(10:41) Why an outsider had to create this new category
(15:34) Health benefits of avoiding alcohol
(17:51) Turner tries the beer
(22:49) Bill’s wife pushing him to start Athletic Brewing
(26:38) Writing a 96 page white paper on non-alcoholic beer
(28:42) Quitting his job to start six months of research and networking
(30:21) Meeting the perfect co-founder after 100’s of meetings
(32:34) Putting his life savings into a warehouse and brewing equipment
(33:04) The importance of setting company values early on
(34:23) Brewing the first beer in Gatorade jugs
(36:16) Selling the first bottles to retailers
(37:42) Explosive growth in 2019
(39:39) Why new products and D2C helped them scale so fast
(40:39) Using TikTok to sell-out new product launches in 30 seconds
(42:00) The value of doing early customer service himself
(44:45) Getting to 61% market share in non-alcoholic beer
(46:10) Struggling to raise the first angel round
(48:34) Using consistent investor updates to easily raise the Seed, Series A, and Series B
(50:47) Transitioning to institutional capital for its Series C
(52:33) Betting on a new category to expand market size
(55:44) Information access is enabling healthier consumer behavior
(58:11) Bill’s early strategy for marketing the product
(1:01:43) The importance of over communicating with your investors
(1:03:44) Why retailers like Athletic Brewing’s unique omni channel approach
(1:06:16) How building its own breweries and supply chain enabled its unique strategy and better margins at scale
(1:09:04) Getting into Whole Foods before launching
(1:11:31) Doing unscaleable things over and over again
(1:13:50) Why entrepreneurship is a long game
(1:14:22) Most of Athletic’s new products come from the team
Check out Athletic Brewing: https://athleticbrewing.com/
Where to find Bill:
LinkedIn: https://www.linkedin.com/in/bill-shufelt-650059138
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Dane Atkinson is the Founder and CEO of Odeko, the all-in-one operations partner for local businesses. Dane has spent his entire career helping small businesses. This episode is a masterclass on selling to SMBs. He shares all his lessons learned as a founder, and how Odeko survived zero revenue during COVID and hit $150 million in revenue two years later. Timestamps (00:00) Intro (03:33) The magic formula to sell to SMBs (04:06) Why every small business starts as a dream (21:57) The reasons you shouldn’t listen to customers (25:16) Lessons running Squarespace for four years (27:12) Why simplicity is better for SMBs (28:58) How Squarespace ran the very first podcast ads (35:35) Lessons messing up his second company (37:46) How to demote an employee (50:29) Coming up with the idea for Odecco (52:05) Why VCs screw their portfolio companies (55:16) How to navigate pivots with your board (01:04:27) Growing revenue from zero to $100m+ in two years (01:12:10) Advice for first-time founders (01:14:18) How Dane would re-design the food system (01:15:39) Why our food is so bad for our health (01:16:17) How Odeko empowers local makers Check out Odeko: https://odeko.com/ Where to find Dane: Twitter: https://twitter.com/daneatkinson LinkedIn: https://www.linkedin.com/in/daneatkinson Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
Josh Miller is CEO and co-founder of The Browser Company, which is building a new internet browser. He explains why effective hiring requires caring a lot and trusting your taste and why Arc Search, a default mobile browser, could be The Browser Company’s next act.
TIMESTAMPS:
(00:00:00) Intro
(00:02:35) Working for Obama
(00:03:55) Giving up 8-figures in Meta stock
(00:08:19) Barack Obama’s favorite web browser
(00:09:02) Why Arc released a mobile browser
(00:10:03) How Josh met Josh Kushner
(00:11:26) Becoming an EIR at Thrive Capital
(00:12:09) How The Browser Company got started
(00:15:51) Why they named it The Browser Company
(00:18:49) Pivoting to consumer when COVID hit
(00:20:37) Leaving Thrive to join as a Co-founder in February 2020
(00:21:05) Why COVID made browsers relevant
(00:22:42) How to hire a great team
(00:25:02) Hiring Josh Lee to edit their videos
(00:26:52) The biggest difference between Josh as a first-time and second-time founder
(00:28:46) Learning to delegate
(00:34:03) Why Thrive gave up double-digit equity back to the founders
(00:40:18) Launching
(00:40:52) Why build a web browser
(00:42:17) This history of browsers
(00:43:36) Why they’ve gotten worse over time
(00:50:26) The reasons people use Arc
(00:53:23) How Arc will make money
(00:56:45) Why Arc’s existential question is getting people to care about their browser
(00:59:47) The story behind Arc Search
(01:00:45) Arc’s potential growth flywheel
(01:09:17) Why Arc bet big on building in public on YouTube
(01:10:16) The publisher backlash to Arc Search
(01:11:33) Why praising your team publicly is so important
(01:13:39) How Josh hired Nate Parrott
More on The Browser Company:
www.youtube.com/c/TheBrowserCompany
Where to find Josh:
Twitter: https://twitter.com/joshm
LinkedIn: https://www.linkedin.com/in/josh-miller-b31259106
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Subscribe to my newsletter The Split for new episodes emailed every week: https://www.thespl.it/ Brought to you by Attio, the next generation of CRM: https://bit.ly/AttioThePeel Peter Walker is Head of Insights at Carta and writes a newsletter called “The Data Minute”, a weekly newsletter highlighting data from over 43,000 private tech companies that use Carta’s platform to manage their cap table. He gives us into a deep dive on VC valuation trends, the fundraising landscape, and startup strategies. Timestamps:
(00:00) Intro
(04:50) Valuation trends in 2023
(08:10) Why Seed valuations went up over the past two years
(12:27) AI startups are getting higher valuations
(17:40) Why Biotech might be the next big bubble
(19:15) Boston as the 2nd largest VC ecosystem
(21:15) How SAFE’s work
(24:06) The impending SAFE reckoning
(26:13) Why startups don’t pay dividends
(28:31) Downrounds were 2x more common in 2023
(32:11) Almost half of all 2023 Series As were extensions
(35:34) Is there really a lot of dry powder?
(40:43) The emerging manager fundraising landscape
(48:19) Exit environment
(51:45) Why pre-Series B is the most common acquisition stage
(52:47) Liquidation preference & why an acquisition at Seed might make a founder more money than at a Series B
(55:59) Compensation market data
(56:38) Why the number of total startup employees shrank in 2023
(57:38) Why startup employees aren’t exercising their options
(1:00:57) Health of the secondary markets
(1:04:51) Most co-founder splits aren’t 50/50
(1:06:47) Why you should always vest co-founder equity
(1:09:30) 2023 record year for startup shutdowns
(1:17:19) Will other startup ecosystems ever catch Silicon Valley? Links: Carta’s Q4 ‘23 Private Market Report: https://carta.com/blog/state-of-private-markets-q4-2023/ Peter’s Newsletter: https://carta.com/subscribe/data-newsletter-sign-up/ Where to find Peter: Twitter: https://twitter.com/PeterJ_Walker LinkedIn: https://www.linkedin.com/in/peterjameswalker/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
Subscribe to my newsletter The Split for new episodes emailed every week: https://www.thespl.it/
Chris Bakke has founded and sold three companies for between $25-100 million to Zillow, Indeed, and most recently Twitter / X. He shares how he convinced Elon to buy his company, what it's like working for Elon, exactly how the Twitter algorithm works, and all his meme making secrets.
— — — —
Timestamps:
(00:00) Intro
(02:52) Inside Twitter’s acquisition of Laskie
(05:38) Why Twitter / X works so well for recruiting
(08:11) A sneak peek at upcoming Premium features
(13:58) How the X algorithm works
(20:48) Why “dwell time” is the most important metric
(24:07) What it’s like reporting to Elon
(27:40) Elon’s crazy ability to context-switch
(29:16) Why you should consider selling your company for $25-100 million
(35:39) The reasons large M&A deals are so rare
(42:07) Surviving inside Big Tech as a founder
(46:23) Chris's philosophy on company building
(51:23) Why “Time in Market” is so underrated
(53:44) YC’s “sandwich incident”
(55:44) How to use memes for marketing
(58:55) Chris’ 100+ page Google Slide meme library
(1:01:46) His top three favorite meme templates
(1:03:48) His favorite proprietary trade secret at X
(1:05:03) Turning down jobs at Coinbase and WhatsApp
— — — —
Twitter jobs: https://twitter.com/jobs
— — — —
Where to find Chris
Twitter: https://twitter.com/ChrisJBakke
LinkedIn: https://www.linkedin.com/in/bakk3/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Subscribe to my newsletter The Split for new episodes emailed every week: https://www.thespl.it/ Brought to you by Attio, the next generation of CRM: https://bit.ly/AttioThePeel Mike is currently a partner at Lightspeed Venture Partners. Before Lightspeed, he spent five years building Anchor, which he sold to Spotify in 2020, and then led Spotify’s podcast, video, and live products for three years. It's probably safe to assume every podcast you listen to uses Mike’s product, and we go way back to the very beginning and talk through how the team at Anchor pulled it all off.Mike also shares his frameworks of “Doing the Dumb Thing” and "Super Goals," which are high-stakes, focusing goals with a clear and urgent time frame, open-ended method of achievement, and a single measure of success. Chapters: (00:00) Intro (4:22) Why AI makes consumer investing interesting again (8:05) Podcasting in the early 2010’s (14:03) The benefits and drawbacks of RSS (21:50) Building v1 “Instagram for audio” (25:53) Advice for building a close-knit community (29:28) Raising their first small round (31:38) Inside their splashy launch at SXSW (39:17) Why the first product failed, but allowed them to raise money to build Anchor (45:26) What makes a good product founder (47:39) Re-launching v2 a year later (53:51) What is a Super Goal (56:32) Finding Product Market Fit with months of runway left (59:02) Getting to a million podcast creators (01:02:09) Launching the first podcast ad network (01:04:10) Why anchor started sponsoring its own ad network (01:08:13) Spotify’s acquisition of Anchor (01:14:22) How Spotify won in podcast market share (01:16:34) Why the future of podcasts is video Referenced: Mike’s Podcast “Generative Now”: https://www.youtube.com/playlist?list=PLXW6zY9x-gk1oPyjZ_qBCDEYKTbPpGa8S Mike’s blog posts: https://mignano.substack.com/p/the-standards-innovation-paradox https://mignano.substack.com/p/the-power-of-supergoals https://mignano.substack.com/p/startups-vs-incumbents-the-battle https://mignano.substack.com/p/all-podcast-roads-lead-to-video Where to find Mike: Twitter: https://twitter.com/mignano LinkedIn: https://www.linkedin.com/in/mignano Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
Eric Newcomer is the founder of Newcomer, a publication he launched in October of 2020 to cover the business of startups and venture capital. He had just left Bloomberg after nearly six years, and was previously the first employee at The Information.
— — — —
Timestamps:
(00:00) Intro
(02:46) The current state of media
(05:59) Anchoring his 4th grade newscast
(07:21) Becoming the 1st employee at The Information
(09:34) How reporters get stories
(21:12) The moment he quit Bloomberg to start Newcomer
(26:02) Why he writes for VC insiders
(32:19) The VC top fund survey
(34:01) The Founders Choice VC leaderboard
(35:51) Why leaked documents grow his newsletter the fastest
(39:45) When Eric knew Newcomer was going to work
(43:31) How events become Newcomers most profitable business
(51:56) Why Eric invested in Substack
(57:42) Why its harder to cover tech’s downturn than boom times
(59:10) How to pitch a story to a reporter
(01:02:59) Why the internet incentivizes negative media coverage
(01:06:06) Advice for starting a media company
(01:10:33) Why media works so well to sell adjacent products
(01:12:55) Newcomer Banking Summit
(01:14:27) The $1.3B acquisition that happened at his first conference
(01:20:05) New products Eric’s thinking about
— — — —
Referenced:
Newcomer Passes $1m in Revenue: https://www.axios.com/2024/01/04/substack-writer-eric-newcomer-says-his-revenue-surpassed-1m-in-2023
Pragmatic Engineer Newsletter: https://blog.pragmaticengineer.com/
Lenny’s Newsletter: https://www.lennysnewsletter.com/
Mike Solana’s Pirate Wires: https://www.piratewires.com/
Mentioned Newcomer Articles:
VC Survey: https://www.newcomer.co/p/sequoia-founders-fund-usv-elad-gil
Founder's Choice: https://www.newcomer.co/p/founders-choice-vc-rankings-revealed
Paywalled Bill Gurley Interview: https://www.newcomer.co/p/above-the-crowd
SBF’s Leaked FTX Email: https://www.newcomer.co/p/exclusive-read-sam-bankman-frieds
Eric’s first article on Sequoia: https://www.newcomer.co/p/sequoias-political-paradox
— — — —
Where to find Eric:
Twitter: https://twitter.com/EricNewcomer
LinkedIn: https://www.linkedin.com/in/ericpnewcomer/
Newsletter: https://www.twitter.com/newcomer
Email: newcomer@newcomer.co
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Siqi Chen is the Co-Founder and CEO of Runway, the modern and intuitive way to model, plan, and align your business for everyone on your team. Or, in Siqi’s words, “revolutionizing the $80 trillion business industry”.
A few months ago, Runway’s new website went viral across the internet. Siqi takes us inside how that happened. He’s no stranger to going viral, having previously built multiple companies that went from zero to millions of users within weeks, including the fastest growing product ever before ChatGPT took the crown in late 2022.
— — — —
Brought to you by Attio, the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioThePeel
— — — —
Timestamps:
(00:00) Intro
(02:00) Sponsor: Attio
(02:59) How Siqi goes viral
(06:13) Why conversion doesn’t always matter
(11:23) How to make B2B software more fun
(14:31) Working on the Curiosity and Spirit rovers at NASA
(16:50) Re-designing at the entire codebase and product at his first startup job
(21:13) Earning the nickname “FB Millz” making a million dollars building Facebook games
(25:11) Selling to Zynga and building the fastest growing product before ChatGPT
(28:36) Building a game with 90% Day 1 retention
(30:09) Being played by Kim Kardashian, Jack Dorsey, and shut down by Tim Cook
(32:10) Almost getting fired building a growth team at Postmates
(35:04) Building Sandbox VR: “escape rooms in VR”
(40:35) Meeting Kanye
(44:38) Getting the idea for Runway when COVID hit
(47:32) Why spreadsheets run every business
(54:40) Disrupting the $80 trillion business industry
(57:55) Making formulas 50x easier than Excel
(01:02:32) Why Runway’s building a painkiller
(01:06:32) How to fundraise
(01:08:32) Why the first question from an investor is the reason they won’t invest
(01:11:28) How to tell a company’s story
(01:15:23) The three layers of a story
(01:17:28) The importance of positioning in storytelling
(01:18:56) Runway’s flexible remote work strategy
(01:21:34) Why their hiring strategy changed over time
(01:22:39) Siqi’s single interview question & the three traits he looks for when hiring
(01:26:10) Unlearning consumer to learn B2B
(01:30:26) Navigating the first three years of no customers
(01:31:45) What surprised Dylan Field the most about building Figma
— — — —
Referenced:
Runway’s website: https://runway.com/
Reform Collective Design Agency: https://www.reformcollective.com/
Amplitude: https://amplitude.com/
SandboxVR: https://sandboxvr.com/
Lulu Cheng’s Android Playbook: https://www.piratewires.com/p/anduril-comms-strategy-early-days
— — — —
Where to find Siqi:
Twitter: https://twitter.com/blader
LinkedIn: https://www.linkedin.com/in/siqic/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Shrav Mehta is the Founder and CEO of Secureframe, which empowers businesses to build trust with customers by automating information security and compliance. Shrav started the company in 2019 after being an early employee at Scale, Pilot, Lob, and Hired, and has since raised from investors like Kleiner Perkins, Backend Capital, Soma Capital, and Banana Capital.
Shrav takes us inside how Secureframe’s automating the compliance market, lessons learned on recruiting and scaling teams, and his contrarian take on finding product market fit.
— — — —
Timestamps: (00:00) Intro (2:10) Automating the $80 billion compliance market (15:49) Learning to program building Android apps (22:50) Joining Lob, Hired, and Scale early (27:25) Joining Pilot to learn marketing and growth (33:31) Shrav’s secret discount furniture supplier (35:04) Finishing three years of college in one year (39:06) Getting 30-40 customers before starting Secureframe (44:24) Non-intuitive fundraising advice from pre-product to IPO (50:08) Why the IPO isn't the ultimate goal (54:40) How Shrav approaches hiring (58:04) Tactics for effective reference checks (1:01:01) Why warm intros are so helpful (1:02:32) How to send good cold emails (1:05:31) Why you should not use LinkedIn “open to work” (1:06:54) Lessons learned scaling teams (1:13:45) Why finding PMF is a 24/7 job and never ends
— — — —
Referenced:
Secureframe: https://secureframe.com/
Lob: https://www.lob.com/
Hired: https://hired.com/
Scale: https://scale.com/
Zapier’s Secrets to PMF: https://www.youtube.com/watch?v=NJMjuYt9jEc
What it took to raise a Series A in 2023: https://news.crunchbase.com/venture/seed-to-series-a-funding-2023-jones-kruze — — — — Where to find Shrav:
Twitter: https://twitter.com/shravvmehtaa/
LinkedIn:https://www.linkedin.com/in/shravmehta/
Where to find Turner:
Twitter: https://twitter.com/turnernovak/
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Kevin Espiritu is the founder and CEO of Epic Gardening, which is, by multiple measures, one of the largest brands in gardening on the planet.What started in 2013 as a blog has since evolved into a gardening empire spanning YouTube, TikTok, Instagram, Facebook, 4,500 gardening stores, and three gardening books.
Epic raised a $17.5m Series A from The Chernin Group in 2021, and according to external sources did $27 million in revenue in 2022.
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Timestamps:
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Where to find Kevin / Epic Gardening
Twitter: https://twitter.com/KevinEspiritu
YouTube 1: https://www.youtube.com/user/kevinmespiritu
YouTube 2: https://www.youtube.com/@epicgardening
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it/
Kirsten Green is the founder of Forerunner Ventures, a venture capital firm that focuses on understanding the mindset of the modern consumer. Kirsten started Forerunner in 2010, and was an early investor in companies like Faire, Chime, Warby Parker, Dollar Shave Club, Hims, Glossier, Jet, Bonobos, HotelTonight, and The Farmer’s Dog. This episode takes us behind the scenes of Kirsten’s two decade journey building Forerunner from scratch. She talks about her biggest mistakes, wins, and lessons learned along the way. Timestamps: (00:00) Intro (02:50) Doing market research at the mall (08:00) Her journey from public markets to venture (18:30) Lessons from her first investment going to $0 (28:51) How she raised her first $5m angel fund (31:11) Transitioning to a $41.7m institutional fund (43:20) Why she almost didn’t invest in Dollar Shave Club (sold for $1.1 billion) (51:05) How Forerunner thinks about fund size (57:05) How she led Faire’s Series A with a small fund (58:46) How Kirsten builds relationships with LPs (01:02:10) Is consumer investing dead? (01:15:00) Her unfair advantage as an investor Where to find Kirsten Twitter: https://twitter.com/kirstenagreen LinkedIn: https://www.linkedin.com/in/kirstengreen Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Newsletter: https://www.thespl.it/
Craig Fuller is the Founder and CEO of FreightWaves, a media company and data provider for the global supply chain. He’s also the CEO of Flying Media Group, which he founded in 2021 to acquire Flying Magazine, the largest US-based print magazine for the aviation industry. This conversation is split into three parts: a crash course on logistics and supply chains, how to build and run a media company, and finally all things print magazines.
Topics discussed include:
Referenced:
Where to find Craig:
Twitter: https://twitter.com/FreightAlley
LinkedIn: https://www.linkedin.com/in/incab
Where to find Turner:
Newsletter: https://www.thespl.it
Twitter: https://twitter.com/TurnerNovak
Banana Capital: https://bananacapital.vc
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Danielle Cohen-Shohet is the CEO and Founder of GlossGenius, the all-in-one booking, payments and POS solution that helps beauty and wellness professionals drive bookings and grow their business.
Danielle started the company in 2016 and has since grown it to a $510 million valuation. This is while taking a disciplined approach to fundraising, raising roughly $70 million throughout the life of the company.
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Topics include:
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Where to find Danielle:
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Where to find Turner:
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Cristina Junqueira is the co-founder of Nubank, the largest neobank in Latin America – and in the world – with more than 80 million customers. She is also the second self-made female billionaire in Brazil. Cristina and her co-founders David Vélez and Edward Wible launched Nubank in 2013, essentially building the fintech category in a market where it was nonexistent, and went on to release a no-fee credit card, app, and other banking products across Brazil, Mexico, and Colombia. Cristina takes us through the rise of Nubank, from the scrappiest days building in a house in Sao Paulo to being backed by investors like Sequoia, Founders Fund, DST, TCV, Tiger Global, and Warren Buffett, and then on to their IPO in December 2021. We also touch on the impact of Nubank’s distinctive brand choices, how they navigated government regulations that nearly shut them down, and how they were able to spend $0 on marketing throughout most of their history.
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TIMESTAMPS:
(00:00) Preview
(02:38) Fintech and the preconditions for disrupting financial services in LatAm
(05:38) Educating investors on the opportunity for fintech in LatAm
(07:35) The scale of unbanked and underbanked populations in Brazil, Mexico, and other countries; and why expanding access to these products increases NuBank's market share
(08:21) Expanding the pie and just how profitable banks can be in LatAm
(15:37) Starting NuBank and the lessons Cristina learned from incumbent banks
(18:11) The biggest hurdle to starting NuBank
(19:33) Navigating Nubank’s first product from inception to successful credit card
(21:08) Spending $0 CAC in an industry with hugely expensive marketing pushes
(22:32) $0 on marketing and scrappy ethics
(26:40) The crazy circumstances around Nubank’s Series A fundraise
(36:54) Cristina’s reflections on the IPO in December 2021
(39:31) How Nubank navigates a changing macro environment
(40:40) The importance of Nubank’s distinctive brand
(42:57) Surviving an existential threat from Brazil’s government
(46:28) Scaling from a small scrappy team to a multinational global publicly traded company
(49:02) Personal growth and maintaining strong co-founder relationships
Referenced:
Nubank: https://nubank.com.br/en/
Nubank's IPO mints Cristina as a billionaire: https://www.forbes.com/sites/jeffkauflin/2021/12/09/
Where to find Cristina:
Twitter: https://twitter.com/junqueira_cris
LinkedIn: https://www.linkedin.com/in/crisjunqueira/
Where to find Turner:
Newsletter:https://www.thespl.it
Twitter: https://twitter.com/TurnerNovak
Banana Capital: https://bananacapital.vc
Sid Yadav is the Co-founder and CEO of Circle, the all-in-one community platform trusted by creators like Tiago Forte, David Perell, and Miles Snider. Sid started the tech blog Rev2 when he was a teenager in New Zealand, writing about the launch of YouTube and the iPhone. He was the founding engineer and designer of Teachable, which he helped scale to +25m+ in ARR before it was acquired in 2020. He started Circle in 2019 with co-founders Rudy Santino and Andrew Guttormsen, which they scaled to $16m in ARR by December of 2023.
Circle has since raised $31m from Investors like Tiger Global, Notation Capital, Bungalow, Todd Goldberg, Rahul Vohra, Scott Belsky, Josh Buckley, Ankur Nagpal, Wade Foster, and Dharmesh Shah.
Sid immigrated with his family from India to New Zealand as a teenager and to the US after college. His story is a perfect encapsulation of the American Dream, and I’m excited to share this conversation.
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Topics discussed include:
(03:53) Why the creator economy is booming despite negative sentiment
(13:22) Writing a popular tech blog as a teen in the mid 00’s
(23:16) Joining Teachable as the 2nd employee
(40:30) Why Teachable CEO Ankur Nagpal invested 90% of his liquid net worth in Circle’s $1.7m Pre-seed round
(48:44) Sid’s inside view at the creator economy before, during, and after COVID
(52:50) The magic of Lenny Rachitsky’s creator flywheel
(56:10) The reason Sid raised a Seed from lots of investors instead of one large check
(01:14:30) Inside raising a Series A from Tiger Global in 2021
(01:22:19) Why Sid writes an investor update every month
(01:25:15) Going from Zero to $16m ARR in four years
(01:27:28) How Circle approaches its product roadmap
(01:29:20) Building a community around your product
(01:37:03) Advice for running a remote-first team
(01:46:54) How Sid convinced the founder of Zapier to be his CEO coach
(01:54:20) Why founders need to deal with reality
Referenced:
“Cost of a meeting” tweet: https://twitter.com/0xgaut/status/1620815168921038850
Tiago Forte Building a Second Brain: https://www.buildingasecondbrain.com/foundation
PARA Method: https://fortelabs.com/blog/para/
Lenny’s interview with Brian Chesky: https://www.youtube.com/watch?v=4ef0juAMqoE
Turner’s interview with Wade Foster, Co-founder and CEO of Zapier: https://youtu.be/NJMjuYt9jEc
Myles Snyder: https://mylessnider.com/
Where to find Sid:
Where to find Turner:
Pim de Witte is the Co-founder and CEO of Medal, which enables millions of gamers to capture and share their favorite gaming moments with friends. Pim started the company in 2015 and has since raised over $72 million, supported by investors like OMERS Ventures, Makers Fund, Dune Ventures, and Horizon Ventures. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://bit.ly/3OwGdGC Read the transcript: https://www.thespl.it/p/growing-medal-to-tens-of-millions In this episode, we discuss: Why we play video games Why 200 million gamers play Roblox Learning to code at 13 to build a private Runescape server that did $1.5 million in revenue Why paid acquisition is so important in mobile gaming Why consumer platforms need a social inflection point How Medal blew up during COVID Why multiplayer platforms die when network effects unravel Why Medal’s Seed round was so hard to raise Pim’s biggest mistake building Medal His three favorite interview questions Medal’s unique hybrid in-person / remote work environment Why it’s a mistake to focus on competitors instead of customers Why rapid iteration is everything How to acquire another startup Why building product is the ultimate game How Elon’s changes at Twitter caused a great reset in tech Where to find Pim: Twitter: https://www.twitter.com/PimDeWitte LinkedIn: https://www.linkedin.com/in/pimdw/ Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Read the transcript: https://www.thespl.it/p/growing-medal-to-tens-of-millions Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Itai Damti is the Co-founder and CEO of Unit, the platform that helps leading tech companies store, move, and lend money.Unit has raised over $170 million from investors like Better Tomorrow Ventures, Accel, Insight, and dozens of angels.
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In this episode, we discuss:
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Kevin Liu is the Co-founder and CEO of Metronome, which enables software companies to launch, iterate, and scale their business models with billing infrastructure that works at any size and stage. Prior to Metronome, Kevin and his co-founder Scott Woody both sold their respective separate companies to Dropbox.
Kevin and Scott started Metronome in 2019, and have since raised over $30 million from investors like a16z, General Catalyst, Elad Gil, Lachy Groom, and dozens of other angels.
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In this episode, we discuss:
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Referenced:
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Wade Foster is the Co-founder and CEO of Zapier, an automation platform that helps you work faster. Wade and his co-founders Mike and Bryan started the company in 2011, and have always done things a bit differently. From being a startup based in Missouri, working as a remote team since 2011, and raising very little outside capital despite being one of the fastest growing startups in the world. — Brought to you by Secureframe, the automated compliance platform built by compliance experts. Get compliant with security and privacy frameworks like SOC 2, ISO 27001, HIPAA, GDPR, and more. Sign-up here: https://bit.ly/3QOr2eo — Topics discussed include: The founding story of Zapier Wade’s contrarian take on Product Market Fit Why new products are usually built on emerging distribution channels How Wade deals with imposter syndrome Never raising more money after a $1.3 million Seed during YC How Zapier thinks about it’s product roadmap Shutting the company down for a weeklong AI hackathon Why Wade thinks LLMs will unlock new types of product interfaces How he delegates work without losing track of the details — Referenced: https://zapier.com — Where to find Wade: Twitter: https://twitter.com/wadefoster LinkedIn: https://www.linkedin.com/in/wadefoster — Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Banana Capital: https://bananacapital.vc — Production and distribution by: https://www.supermix.io — Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Gaurab Chakrabarti and Sean Hunt are the Co-founders of Solugen, which replaces petroleum based products with plant-derived substitutes without sacrificing affordability or performance. They met playing poker in college, kickstarted the company with $10k from an MIT pitch competition, and have since scaled the business to over nine-figures in revenue.
Solugen has raised over $642 million from investors like Fifty Years, Lowercarbon Capital, Founders Fund, Refactor Capital, and Cantos Ventures.
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Topics discussed:
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Referenced:
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Where to find Sean:
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Where to find Turner:
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Jonathon Barkl is the Co-founder and CEO of AirGarage, a full-stack parking management company that helps real estate owners increase their income.
Jonathon and his co-founders Chelsea and Scott started the company in 2017. They’ve since raised roughly $15 million from investors including Founders Fund, Floodgate, a16z, Abstract, and prior guest of the show Ryan Delk.
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Topics discussed:
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Referenced:
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Dan Lorenc is the Co-founder and CEO of Chainguard, the best way to secure your open source software. Dan and his co-founders Kim, Matt, and Ville started the company in 2021 after spending a decade working together at Google on all things open source and software security. They’ve since raised $116 million from investors including Spark (led Series B), Sequoia (led Series A), Amplify (led Seed), The Chainsmoker’s Mantis VC, Banana Capital, and dozens of angels in the cyber security and open source communities. — Topics discussed: What is the “software supply chain”? How the SolarWinds breach created the software supply chain security market The history of open source software Why open source software makes software supply chains even less secure The moment Dan and his co-founders decided to start Chainguard Why they started selling consulting services before even building a product The reason their first two products solved completely different problems (top-down and bottoms-up), and why the one that didn’t work at first is now their main business Why Chainguard decided to focus on a broad communications and marketing strategy so early on How Dan gets quoted in major media publications as an early stage startup founder Why Chainguard uses memes for marketing Why Dan thinks startups should “make content optimized for the group chat” How they raised their Seed round from Amplify a week after leaving Google Raising a Series A from Sequoia as the market started collapsing in Spring of 2022 Dan’s advice for founders on dealing with investor inbound when not fundraising Why he wish he hired sales reps sooner Raising a Series B from Spark Capital to accelerate their enterprise sales process — Referenced: https://www.chainguard.dev https://www.sigstore.dev/ Battling the Trojan Horse in Open Source: https://www.sequoiacap.com/article/dan-lorenc-chainguard-spotlight/ Chainguard Series B Announcement: https://www.chainguard.dev/unchained/series-b-funding Dan’s favorite open source project: https://github.com/jqlang/jq Reflections on Trusting Trust: https://www.cs.cmu.edu/~rdriley/487/papers/Thompson_1984_ReflectionsonTrustingTrust.pdf — Where to find Dan: Twitter: https://twitter.com/lorenc_dan LinkedIn: https://www.linkedin.com/in/danlorenc — Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Banana Capital: https://bananacapital.vc — Production and distribution by: https://www.supermix.io — Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Nichole Wischoff is the founder of Wischoff Ventures, a Pre-Seed and Seed firm that invests up to $1 million in non sexy industries. Nichole closed her first fund in 2021, and previously was an early employee at Blend (NYSE:BLND), One (acquired by Walmart in 2022), and Built.
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Topics discussed include:
• Growing up on food stamps in Arkansas
• How studying abroad in Belgium changed Nichole’s life
• How falling in love with running got her into college and her first job
• Why Taylor Swift could be the first female President
• Opening a bakery to pay rent while teaching English in Spain
• Getting her first job at Citi’s non-profit housing financing team
• Leveraging that experience to get a job in fintech
• Making her first angel investment in Vesta
• How Nichole got One Financial its first 25k users
• Helping sell One Financial to Walmart
• How Lee Fixel and Chad Byers helped raise her first $5m fund
• Lessons learned going from a $5m to $20m fund in 2022
• Nichole’s advice for anyone raising their first fund
• Behind the scenes of her viral “Third Tier VC” moment
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Referenced:
•Taylor Swift (Acquired’s Version): https://www.acquired.fm/episodes/taylor-swift-acquireds-version
• Nichole’s $20m Fund Announcement https://techcrunch.com/2022/12/16/solo-gp-nichole-wischoff-raises-20m-fund-backed-by-peter-thiel-to-invest-in-unsexy-businesses/
• J Cal’s “3rd or 4th Investor in Uber” Montage: https://www.youtube.com/watch?v=OK4Mku_s4H4
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Where to find Nichole:
• Twitter: https://twitter.com/NWischoff
• LinkedIn: https://www.linkedin.com/in/nicholewischoff
• Wischoff Ventures: https://www.wischoff.com/
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Where to find Turner:
• Newsletter: https://www.thespl.it
• Twitter: https://twitter.com/TurnerNovak
• Banana Capital: https://bananacapital.vc
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Waseem Daher is the Co-founder and CEO of Pilot, the bookkeeping, CFO, and tax provider for startups and fast growing businesses. Prior to Pilot, Waseem and his co-founders Jeff and Jessica sold companies to Oracle and Dropbox.
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Waseem, Jeff, and Jessica started Pilot in 2017, and have since raised over $160 million from investors like Index Ventures, Stripe, Sequoia, Whale Rock, Jeff Bezos, and over 40+ angel investors.
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In this episode, we discuss:
• Why Waseem’s building a startup that does your accounting
• The reason he first started doing his own bookkeeping, and why he doesn’t recommend it to other founders
• When startups should build something themselves and when to outsource
• All the mistakes Waseem made building and selling his first two startups to Oracle and Dropbox
• How to avoid “fake work”
• How to get ROI from conferences
• His disastrous first ever meeting with a VC
• Why the best fundraising advice is to build a business that doesn’t need to raise money
• “Companies are bought, not sold” and his framework for startup M&A
• Why it’s a mistake to build your startup just to be acquired
• Why consensus startup ideas rarely work, and the best startups need some secret or structural change that no one else has noticed yet
• Why tech-enabled service businesses are so hard to scale
• How Pilot got its first customers
• Pilot’s unique approach to raising its Seed round
• The initial scare when raising their Series A
• Why its Series B was half of what they could have raised
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Where to find Waseem:
• Twitter: https://twitter.com/waseem
• LinkedIn: https://www.linkedin.com/in/wdaher
• Newsletter: https://waseem.substack.com/
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Where to find Turner:
• Newsletter: https://www.thespl.it
• Twitter: https://twitter.com/TurnerNovak
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Vlad Magdalin is the Co-founder and CEO of Webflow, software that empowers designers to build websites without code. Vlad started the company with his co-founders Sergie Magdalin and Bryant Chou in 2013, and has since raised roughly $335 million supported by investors like Accel, Khosla Ventures, YCombinator, Capital G, and Eric Bahn.
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Disclaimer: Mercury is a financial technology company, not a bank. Banking services are provided by Choice Financial Group and Evolve Bank & Trust; Members FDIC.
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Topics discussed include:
• The history of web browsers, websites, and web design
• Why websites are the ultimate economic enablers
• How Webflow empowers anyone to design websites without code
• Why website design is a gateway into programming
• How the movement to CSS and web standards in the 2000’s and 2010’s created the opportunity for Webflow to build a product around responsive design
• Moving to the US with his parents and five siblings as refugees from the USSR at nine years old
• How losing half of their luggage and immigration documents in the move enabled his dad to buy the family’s first computer
• The first website Vlad ever designed for a Brad Pitt movie
• How his experience dropping out of a computer science degree to work in 3D animation at Pixar, then going back to school gave him the idea for Webflow
• Failing to build Webflow three times between 2005 and 2008
• Why the spouses and partners of founders are the unsung heroes of startups
• The moment he immediately quit his job and attempted Webflow for the fourth time
• Burning three months of runway on a Kickstarter that never went live
• Liquidating his retirement account, paying rent with credit cards, and selling and leasing back the family car’s to keep the business running
• Vlad’s exuberant optimism that kept him going for 10 years
• Failing to get into YC, and the crazy story behind getting accepted the second time
• The trajectory-altering customer and fundraising advice they got from Paul Graham
• The “Investing on Principle” contract they signed with Accel who led Webflow’s Series A
• Why Vlad thinks every startup founder should operate with the assumption they’ll never be able to raise money again
Referenced:
• Inventing on Principle (Video): https://www.youtube.com/watch?v=PUv66718DII
• Inventing on Principle (Transcript): https://jamesclear.com/great-speeches/inventing-on-principle-by-bret-victor
• The Infinite Game: https://simonsinek.com/books/the-infinite-game/
Where to find Vlad:
• Twitter: https://twitter.com/callmevlad
• LinkedIn: https://www.linkedin.com/in/vladmagdalin
Where to find Turner:
• Newsletter: https://www.thespl.it
• Twitter: https://twitter.com/TurnerNovak
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Keith is the Co-founder and CEO of OpenStore, a portfolio of brands building its own shopping destination. Before starting OpenStore, Keith was an early executive at companies like PayPal, eBay, LinkedIn, and Square, a co-founder of OpenDoor, and an early investor in companies like DoorDash, Faire, Affirm, Webflow, Ramp, and Stripe, and is also currently a General Partner at Founders Fund Keith started the company in 2021 with co-founders Jack Abraham, Matt Lanter, and Jeremy Wood, and has since raised over $150 million supported by investors like Atomic, Founders Fund, General Catalyst, Khosla Ventures, Lux Capital, and Vine Ventures. — Brought to you by Packsmith, better fulfillment for growing brands. Sign-up here https://bit.ly/PacksmithBanana — In this episode, we discuss: • The 3-minute conversation that started OpenStore • All the problems that still exist in ecommerce • Why Instagram Shopping failed • What Keith and team are building at OpenStore • Why Wish failed • The margin profile of most consumer brands • A crash course on contribution margin and profitability for startup founders • How OpenStore gets 3x higher contribution margin than other consumer brands • As a VC, the one thing Keith looks for in the founders he backs • A framework for founders and investors to consider when incubating companies • Why Keith thinks no great SF-based startups has been founded since March of 2020 • The reasons he moved to Miami • Why he’s bearish on most AI startups • His favorite interview questions for candidates Referenced: • Email Keith - keith@foundersfund.com Where to find Keith: • Twitter: https://twitter.com/rabois • LinkedIn: https://www.linkedin.com/in/keith Where to find Turner: • Newsletter: https://www.thespl.it • Twitter: https://twitter.com/TurnerNovak Production and distribution by: https://www.supermix.io Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Natasha Vernier is the Co-founder and CEO of Cable, the all-in-one effectiveness testing platform for financial services. Prior to Cable, Natasha joined UK neobank Monzo when it had less than 100 customers. She built and led their financial crime team for five years, and is one of the most knowledgeable individuals in the world on financial crime, which amounts to over $4 trillion per year, or 4% of global GDP.
Natasha started Cable in 2020 with her co-founder Katie Savitz, and has since raised over $16 million supported by investors like LocalGlobe, CRV, Stage 2, and Jump Capital.
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Topics discussed:
• How crime is a $4 trillion market
• Why 80% of crime is carried out for financial gains
• Why the UN estimates we only catch 0.2% of financial crime
• The reason banks are incentivized to stop fraud, but not crime
• Why it's so hard to stop financial crimes
• How $20B in financial crime was committed on crypto rails in 2022
• What “Synthetic ID Fraud” is, and why it's the fastest growing type of fraud in the US
• What Natasha thinks are the new frontiers of fraud
• Joining Monzo as one of the first employees and staying through a $4B valuation
• What it’s like to be fully invested in a startup when you’re not a founder
• Building Cable to enable regulatory and financial crime teams
• Raising a Pre-Seed round and signing the first customer without a product built
• Why compliance officers want to buy complicated products
• How Natasha diversified her cap table, raising a Seed round from CRV and a group of angels with broad skill sets, ethnicity, race, and sexuality
• How she got two funds to pre-empt her Series A
• Why founding a startup means getting punched in the face every day, and her biggest mistake is not enjoying the little things sooner
• The two founders she most looks up to
• The one interview question she asks every candidate at Cable
Referenced:
• Cable’s site: https://cable.tech
• Cable’s Seed round: https://community.cable.tech/weve-raised-5-3m-from-crv-localglobe-and-a-diverse-group-of-exceptional-angels/
• How They Built the Hoover Dam (Part 1): https://www.youtube.com/watch?v=rXFjLaUxpaw
• How Vegas Became VEGAS (Part 2): https://www.youtube.com/watch?v=3QNuYHEzS2o
Where to find Natasha:
• Twitter: https://twitter.com/natashavernier
• LinkedIn: https://www.linkedin.com/in/natashavernier
Where to find Turner:
• Newsletter: https://www.thespl.it
• Twitter: https://twitter.com/TurnerNovak
Production and distribution by: https://www.supermix.io
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Alex Bouaziz is the Co-founder and CEO of Deel, a full stack global HR and payroll platform. But the company didn’t start that way, and we’ll talk through Alex and his co-founder Shuo’s journey from zero to one, starting with a product that helped startups hire international employees.
Alex and Shuo launched the company one week before YC Demo day in 2019, and have since scaled to 20,000+ customers and raised over $685 million. They’re supported by investors like YC, a16z, Spark Capital, Weekend Fund, Coatue, SV Angel, Soma Capital, Quiet Capital, and angels like Lachy Groom, Nat Friedman, Ryan Petersen, Alexis Ohanian, John Zimmer, Dara Khosrowshahi, Rex Salisbury, Justin Mateen, and more.
—
In this episode, we discuss:
• The initial insight around remote work that started Deel in 2019
• How they initially built the wrong solution
• Pivoting one week before YC demo day
• Listening to customers to build a better product
• Growing 20% every month for a year
• Being a default optimist
• Dealing with the emotional ups and downs of building a startup
• Moving at “Deel Speed”, and how the team operates so fast
• Deel’s remote-first approach and its “WeWork Squads”
• His advice to other leaders building remote teams
• Why founders shouldn’t share too much information with early investors
• How Alex’s approach to fundraising changed through his Seed to Series D rounds
• Why founders should always be selling their product
• How picking board members is a form of marriage, and what founders should prioritize when picking them
• Why Deel raised a Series A and B in a three month span despite only burning $300k since closing its Seed round
• How deep pocketed investors unlock optionality as a company scales
• The benefits to taking on lots of angel investors
• How Deel prioritized international expansion as it grew
• Deel’s new Visa / immigration and HR AI products
• Two things Alex would do differently if he could start over
• The founders he most looks up to
—
Read the transcript: https://www.thespl.it/p/growing-deel-to-300m-arr-in-four
Where to find Alex:
Twitter: https://twitter.com/Bouazizalex
LinkedIn: https://www.linkedin.com/in/alexbouaziz/
Where to find Turner:
Newsletter: https://www.thespl.it
Twitter: https://twitter.com/TurnerNovak
Production and distribution by: https://www.supermix.io
For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Semil Shah is the Founder of Haystack, an institutional venture capital firm that backs outlier founders at the earliest stages. Semil started Haystack in 2013, and has since invested in X unicorns like DoorDash, Instacart, Figma, HashiCorp, Ironclad, Carta, Applied Intuition, and Opendoor.
This episode takes us behind the scenes of Semil’s two decade journey building Haystack from scratch. We’ll dive into how he raised and deployed each of the first six Haystack funds, including all the mistakes made along the way, plus the details around Haystack’s new $75 million and $25 million funds announced the date this episode was published.
Read Haystack's announcement here: https://semilshah.com/2023/09/10/announcing-haystack-vii-same-model-fresh-funds-and-new-era/
—
Brought to you by Mercury, the bank built for startups. Join more than 100,000 startups and venture capital firms on Mercury, the powerful and intuitive way for ambitious companies to bank.
Sign-up now: https://bit.ly/3sQRzOw
Listen to my conversation with Immad, the Co-founder and CEO of Mercury:
Disclaimer: Mercury is a financial technology company, not a bank. Banking services are provided by Choice Financial Group and Evolve Bank & Trust; Members FDIC.
—
Topics discussed include:
Where to find Semil:
Where to find Turner:
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Sean Frank is the CEO of Ridge Wallet, a men’s wallet and accessories brand that does over 9-figures in annual revenue. The company started in 2012 and raised $266,000 in a Kickstarter campaign to sell the first 5,200 wallets. Ridge hasn’t raised a single dollar of outside capital since, and has also expanded into new categories like rings, knives, watches, backpacks, and keys, with dozens of more products coming soon. Sean is known in some circles as the “Einstein of Ecommerce”, and he gives us an inside look at running a consumer brand in 2023.
Brought to you by Packsmith, better fulfillment for growing brands: https://bit.ly/PacksmithBanana
In this episode, we discuss:
Where to find Sean:
Twitter: https://twitter.com/SeanEcom
Substack: http://seanecom.substack.com/
Podcast: https://9operators.com/
Where to find Turner:
Newsletter: https://www.thespl.it
Twitter: https://twitter.com/TurnerNovak
Referenced:
https://www.amazon.com/Great-CEO-Within-Tactical-Building-ebook/dp/B07ZLGQZYC
https://www.theloganbartlettshow.com/
https://www.maryruthorganics.com/
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Dimitri Dadiomov is the Co-founder and CEO of Modern Treasury, an operating system for the new era of payments. Dimitri and his co-founders Matt and Sam started the company in 2018 after running into the same problem working together at their previous startup. Modern Treasury has since raised over $183 million, supported by investors like YCombinator, Benchmark, Altimeter, Salesforce Ventures, Quiet Capital, WndrCo, TQ Ventures, and Edward Lando. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://bit.ly/3OwGdGC Sign-up for Ramp and get $500: https://bit.ly/3KSqfFV Read the transcript: https://www.thespl.it/p/how-to-move-quadrillions-of-dollars In this episode, we discuss: How the global banking system moves over $1 quadrillion per year Why B2B products should be easy to use with broad use cases What makes a good API business Why the YC application is a great forcing function for founders How it took them six months to get their first customer, but never pivoted Why the first customers of a B2B business should get more credit How PLG helped build a better product Finding holes in the market for an initial go-to-market strategy The depth of Modern Treasury’s product Why they should have built a sales team sooner How deep customer relationships across many industries helped them raise a Series A Why it’s important to go slow to go fast How Dimitri set an intentional culture around studying other businesses When distribution can be more important than product What happened inside Modern Treasury during the collapse of SVB and Signature Bank Why Dimitri sends Saturday update emails to entire company The founders Dimitri really admires Where to find Dimitri: Twitter: https://twitter.com/dadiomov LinkedIn: https://www.linkedin.com/in/dadiomov/ Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Read the transcript: https://www.thespl.it/p/how-to-move-quadrillions-of-dollars Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Kendall Baker currently leads Yahoo’s sports newsletter business. In 2017 he launched the first daily sports newsletter called Sports Internet, which he sold to Axios in 2019. Before Sports Internet, he convinced the founders of The Hustle to focus their online tech blog on a daily newsletter, which he wrote for a year and a half. And before The Hustle, he produced SportsCenter at ESPN. He’s spent nearly a decade at the intersection of daily news and sports, and this episode is packed with insights on both.
Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://bit.ly/3OwGdGC
Read the transcript: https://www.thespl.it/p/the-business-of-newsletters
In this episode, we discuss:
Listen on other platforms:
Apple: https://podcasts.apple.com/us/podcast/the-business-of-newsletters-kendall-baker/id1694440669?i=1000624033211
YouTube: https://youtu.be/4es4p7sFMf0
Where to find Kendall:
Twitter https://twitter.com/kendallbaker
Where to find Turner:
Newsletter: https://www.thespl.it
Twitter: https://twitter.com/TurnerNovak
Read the transcript: https://www.thespl.it/p/the-business-of-newsletters
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Dan Porter is the Co-founder and CEO of Overtime, a sports network for the next generation of fans. OT reaches 85 million fans per month and runs a basketball league (Overtime Elite, OTE), a flag football league (OT7), and is launching a boxing league (OTX) the week this episode airs.
Dan started Overtime with his co-founder Zack Weiner in 2016, and has since raised over $215 million. OT is supported by investors like the late ex-NBA Commissioner David Stern, Jeff Bezos, Drake, Carmelo Anthony, Trae Young, over 25 other NBA players, Spark Capital, Redpoint, a16z, Greycroft, Afore Capital, and Banana Capital. [Turner Novak and Banana Capital are investors in Overtime].
Brought to you by Secureframe, the automated compliance platform built by compliance experts: http://bit.ly/3Qk4RNd
In this episode, we discuss:
Read the transcript: https://www.thespl.it/p/how-overtime-grew-to-85-million-fans
Where to find Dan: Twitter: https://twitter.com/tfadp LinkedIn: https://www.linkedin.com/in/danporter/
Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/TurnerNovak
Where to find The Peel: YouTube: https://www.youtube.com/@ThePeelPod Instagram: https://www.instagram.com/ThePeelPod TikTok: https://www.tiktok.com/@ThePeelPodcast
Read the full transcript: https://www.thespl.it/p/how-overtime-grew-to-85-million-fans
Production and distribution by: https://www.supermix.io
For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Nick Saltarelli is the Co-founder of Mid-Day Squares, a healthy, functional chocolate bar. Nick, his wife Lezlie, and her brother Jake started the company in 2018 from their kitchen in Montreal, and have since built their own factory with $70 million in capacity, and grown the company to a $26 million revenue run rate. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit Read the transcript: https://www.thespl.it/p/building-a-70-million-chocolate-factory In this episode, we discuss: The history of the $200 billion chocolate market Competing against 100+ year-old monopolies Finding a huge opportunity in healthier chocolate The dirty secrets of contract manufacturing Why no one knows how to make a Snickers bar, and Coca-Cola doesn't have a patent How to build a moat in CPG Why Mid-Day Squares had to build their own factory Making chocolate like Tesla makes cars Copying Facebook’s launch strategy Measuring product market fit in CPG Almost running out of money during COVID Why every founding team should go to therapy Surviving an 85% drop in revenue How to raise a bridge round Building an enduring brand Why marketers should study the music industry Timestamps [00:00:00] Intro [00:03:07] The insane politics of chocolate [00:04:53] The history of chocolate [00:07:11] The enormous market for chocolate [00:10:24] The nutrition of chocolate [00:15:00] The Mid-Day Squares origin story [00:20:05] Creating the first product [00:25:53] Why Coca-Cola never filed a patent on their formula [00:29:08] Why they built their own manufacturing plant [00:31:35] A crazy and creative fundraising strategy [00:39:26] Taking over an island and finding PMF [00:46:32] Raising $2m to prove 2 things [00:47:15] Automating production and navigating manufacturing chaos [00:51:11] Why he had to "plead with the government on public TV” [00:53:51] On "eating shit sandwiches” [00:57:30] The COVID mistake that dropped revenue by 85% [01:03:02] Advice for raising a bridge round [01:04:55] How to build fans not customers [01:07:12] How to build in public [01:12:23] Rapid fire questions Where to find Nick Twitter: https://twitter.com/nickywonka Where to find Turner LinkedIn: https://www.linkedin.com/in/turnernovak Newsletter: https://www.thespl.it/ Twitter: https://twitter.com/TurnerNovak Where to follow The Peel podcast YouTube: https://www.youtube.com/@ThePeelPod Instagram: https://www.instagram.com/ThePeelPod TikTok: https://www.tiktok.com/@ThePeelPodcast Read the transcript: https://www.thespl.it/p/building-a-70-million-chocolate-factory Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Ilir Sela is the Founder & CEO of Slice, the online ordering and all-in-one software platform that helps pizzeria’s manage their business. Ilir started the company in 2010 as MyPizza, rebranded to Slice in 2015, and has since raised over $125 million and supports over 20,000 independent pizza shops. Slice is supported by investors like GGV, KKR, 01 Advisors, Primary Ventures, FJ Labs, and RiverPark Ventures. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit Read the transcript: https://www.thespl.it/p/arming-the-pizza-rebels-ilir-sela In this episode we cover - The three reasons small pizza shops are growing 24x faster than big chains - How franchising and "reverse franchising" works - Ilir's biggest mistakes building a franchise business before starting Slice - How to explain a new business model to investors - The customer acquisition benefits of a multi-product model - Bootstrapping Slice to $3 million in profit - Turning down two acquisition offers, one that would have made him nine figures personally - Why MrBeast Burger failed - Why we don't need more cloud kitchens - Empowering entrepreneurs to open their own pizza shops - Building a strong board - Advice for founders selling to small businesses Referenced Cloud Kitchens: https://www.thefoodcorridor.com/blog/everything-you-need-to-know-about-cloud-kitchens-ghost-kitchens/ Frank Slootman from Snowflake, who Illir said inspires him: https://www.linkedin.com/in/frankslootman/ Growth in independent pizzerias vs big chains in 2022: https://www.pmq.com/pizza-power-report-2023/ Jeff Richards from GGV Capital, who invested in Slice and gave Illir some advice mentioned in the podcast: https://www.linkedin.com/in/jeffrichards/ Michelle Obama on whether pizza is a vegetable: https://www.youtube.com/watch?v=G14qNHPE4qo&t=21s MrBeast’s MrBeast Burger: https://www.mrbeastburger.com/ The growth of Domino’s stock since 2010: https://www.cnbc.com/2020/02/25/dominos-stock-yields-higher-returns-than-google-since-ipos.html Slice’s website: https://slicelife.com/ Where to find Turner Newsletter: https://www.thespl.it/ Twitter: https://twitter.com/TurnerNovak Where to find Ilir: LinkedIn: https://www.linkedin.com/in/ilirsela Twitter: https://twitter.com/ilirsela Timestamps [00:03:34]: The enormous and fascinating pizza industry [00:04:30]: Why there are so many independent pizza shops [00:07:33]: Illir's deep family history with pizza [00:10:43]: What Slice provides independent pizzerias [00:14:21]: The origins of Slice (mypizza.com) [00:16:55]: Building "Nerd Force" before Slice [00:18:22]: How franchises like “Nerd Force” work [00:22:15]: Selling his first company: Nerd Force [00:23:46]: Forming the idea for Slice [00:27:19]: The very first customers [00:32:37]: Turning down $18 million to double down on Slice [00:33:41]: Raising money and starting Slice phase 2.0 [00:39:27]: An acquisition offer that was “tough to say no to” [00:41:55]: Slice's focus now and in the near future [00:45:01]: Why there are so many pizza shops [00:46:46]: Hot takes on Cloud Kitchen and Beast Burgers [00:51:55]: Why online customers are worth 4x more than offline ones [00:53:32]: Why some investors doubted Slice [00:57:58]: The underrated value of a good board [01:00:57]: Advice for founders serving small businesses [01:03:29]: Hitting $500m annual revenue with Slice 3.0 [01:04:31]: Other categories Slice could go after [01:06:25]: Rapid fire questions Read the transcript: https://www.thespl.it/p/arming-the-pizza-rebels-ilir-sela Production and distribution by: https://supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Adrian Aoun is the Founder and CEO of Forward Health, which is rebuilding healthcare as a product, not a service. Forward is supported by investors like Founders Fund, Khosla Ventures, Softbank, Expa, Marc Beinoff, Ashton Kutcher, The Weeknd, Lee Linden, Josh Kushner, First Round Capital, Eric Schmidt, DCVC, and more, Before starting Forward, Adrian worked with Larry Page at Google to setup and launch new companies inside of Alphabet. He joined Google through the acquisition of his AI startup Wavii, and spent his first year at Google helping create and build its AI division. Adrian was on the President's Council of Advisors on Science and Technology, and is an angel investor in companies including Stripe, Uber, Anduril, and more. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit In this episode, we discuss: Rad the transcript: https://www.thespl.it/p/making-healthcare-a-product-not-a - How the healthcare industry actually works - Why poor incentives make technology in the industry ROI-negative - The founding story of Forward - Why healthcare should be a product, not a service - Building doctor's offices like Tesla builds cars - Being Larry Page’s right hand man at Google - Building a “healthcare operating system” like Apple builds the app store - Adrian’s contrarian views on the food industry - Why animal farming is a bigger climate issue than you might think - Zuck: the man in the arena Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Where to find Adrian: Twitter: https://twitter.com/adrianaoun LinkedIn: https://www.linkedin.com/in/adrianaoun Read the transcript: https://www.thespl.it/p/making-healthcare-a-product-not-a Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Immad Akhund is the Co-founder and CEO of Mercury, a digitally native bank for startups. Mercury is supported by investors like a16z, Coatue, CRV, Chapter One, Ryan Peterson, Scott Belsky, Serena Williams, Terrence Rohan, Zach Coelius, Todd Goldberg, and more. Before Mercury, Immad was a part-time partner at YC, co-founded Heyzap which sold for $45 million, and co-founded and scaled Clickpass to millions of users.
Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit
Read the transcript: https://www.thespl.it/p/the-future-of-banking-remote-work
In this episode, we discuss:
- The future of banking
- Why Mercury’s beautiful onboarding was an accident
- Cultural mistakes most startups make
- Two lessons from selling his first company for $45 million
- How to get free legal advice
- Why it’s better to build a network of entrepreneurs than investors
- How to fundraise
- Why its contrarian to start a non-AI company right now
- How Mercury is thinking about AI
- Why each operational team has its own engineering team
- The embarrassing pitch meeting that raised his Series A from a16z
- How crypto used up all its goodwill
- The hiring advice he gives every founder
Where to find Immad:
Twitter: https://twitter.com/immad
LinkedIn: https://www.linkedin.com/in/iakhund
Podcast: https://curiositypodcast.substack.com/
Where to find Turner:
Newsletter: https://www.thespl.it
Twitter: https://twitter.com/TurnerNovak
Mentioned in this episode:
Mercury https://www.mercury.com
The Logan Bartlett Show: https://www.youtube.com/watch?v=QcL_cjZDeFU
Timestamps:
(0:00) Intro
(5:58) Mercury's "accidentally great" onboarding experience
(8:13) The fundamental banking business model
(9:34) The basics of banking regulation
(11:07) How Mercury works with banks
(13:27) The future of banking
(19:34) Immad's previous startups
(22:30) What culture actually means
(27:06) Importance of ideas vs execution
(32:03) Learning banking from scratch
(35:54) Why the first banking partnership failed
(37:56) Why the second banking partnership worked
(39:24) The difference between compliance and risk teams
(42:08) Why compliance is so relevant for better banking
(50:13) The biggest mistake for doing remote work
(51:21) Mercury Raise
(53:33) The game theory of fundraising
(54:54) Playbook for generating fundraising momentum
(60:45) Common fundraising mistakes
(63:12) Hilarious fundraising mishap in front of a16z
(68:16) Companies that aren't like this shouldn't touch AI
(70:57) Who will win big from AI?
(72:10) Immad's take on crypto
(86:14) Outro
Read the transcript: https://www.thespl.it/p/the-future-of-banking-remote-work Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Ryan Delk is the Co-Founder and CEO of Primer, a startup helping ambitious kids unlock their potential by empowering teachers to launch and run their own micro-schools. Primer’s supported by investors like Founders Fund, Khosla Ventures, Village Global, Susa Ventures, Sam Altman, Naval, Ryan Peterson, Amjad Masad, Julie Zhuo, Tobias Lutke, Lachy Groom, Howie Liu, Dylan Field, Packy McCormick, and many more. Before Primer, Ryan was the COO at peer-to-peer rental marketplace Omni (sold to Coinbase), and prior to that led Growth and Partnerships at Gumroad from $10,000 to $50 million in GMV. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit
Read the transcript: https://www.thespl.it/p/turning-techers-into-superheroes In this episode, we discuss: - How the $1 trillion US K-12 education system works - The broken incentive structures in education - Why teachers are superheroes - How to double a teacher’s income - Primer’s origin story - How to open a school - If online school works - Why founders make the best employees - How the US government wastes billions of dollars - Why everyone should care more about local politics Where to find Ryan: Twitter https://twitter.com/delk LinkedIn: https://www.linkedin.com/in/delk/
Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Timestamps: (3:42) The state of K-12 education in the US (6:35) The structural problem causing a radical misallocation of resources (8:00) The importance of teachers (9:34) The “totally flipped” incentive structure for teachers (12:22) The problem of bureaucracy in education (13:38) Primer’s thesis (14:52) How to start a school (16:00) How Primer helps teachers start their own schools (18:20) Using underutilized real estate to host micro-schools (20:05) Ryan’s take on digital vs in-person learning (21:59) How Primer supports teachers (23:21) Inspirational stories from Primer users (28:00) The underestimated entrepreneurship of teachers (29:12) How Primer stays affordable for all users (30:26) How Primer gets teachers on board (32:04) The role of after-school activities (33:07) How Primer sets its Curriculum (35:14) Ryan’s unique education and how it inspired Primer (38:39) Why someone hadn’t solved this problem yet (40:24) Primer’s initial strategy (41:30) The breakfast that changed everything (42:09) The concept of “Barrels” from Keith Rabois (42:36) Finding and recruiting Ian Bravo (43:31) How Primer recruits ex-founders (44:52) The 3 things Primer screens for in teachers (46:27) What Primer messed up when launching (48:19) Re-thinking school admissions from first principles (51:03) How they convinced the very first teachers to try Primer (51:59) The ineffective usage of education spending (53:28) Policymakers prioritizing “signal over outcomes” (57:21) The worst public schools are worse than you think (59:08) How the Government wastes billions of dollars and Ryan’s idea for solving this (61:31) The importance of increasing engagement with local politics (63:37) The vision for Primer
Read the transcript: https://www.thespl.it/p/turning-techers-into-superheroes
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Ken Ehrman is the co-founder and Managing Partner of Halo Collar, a smart dog collar that tracks your dog with GPS. Halo Collar uses patented technology that allows customers to instantly create up to 20 unique virtual dog fences from their phone using GPS.
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Read the transcript: https://www.thespl.it/p/the-iphone-for-your-dog-ken-ehrman
In this episode, we discuss: - Working for Mike Markkula, the first investor in Apple - Building hardware and the importance of patents - Listening to customers, solving their problems, and sizing a market - Qualifying enterprise customers and selling with "calm confidence." - Early investors trying to buy 95% of his first company - Getting the US Post Office and Army to fund $15 million in R&D - Taking a company public in 1999 with $3 million in revenue - Using AI to train dog movements and make "the Apple Watch" for dogs - The crazy story of how he met his celebrity co-founder, Cesar Millan the Dog Whisperer - What happened when they met famous TikToker Charli D'Amelio Where to find Ken: LinkedIn: https://www.linkedin.com/in/ken-ehrman
Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak
Referenced: Buy the Halo Collar: https://www.halocollar.com/ Cesar Millan, 'the Dog Whisperer': https://www.cesarsway.com/ More on RFID tags: https://www.youtube.com/watch?v=Ukfpq71BoMo&ab_channel=ALLABOUTELECTRONICS Read the transcript: https://www.thespl.it/p/the-iphone-for-your-dog-ken-ehrman
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Jonathan Neman is Co-Founder & CEO of Sweetgreen, an American fast casual restaurant chain that serves salads. Jonathan and his co-founders started the company in 2007, opening their first restaurant just three months out of college. Sweetgreen opened its second and third locations in the middle of the 2008 Global Financial Crisis, and went public in 2021 in the middle of the COVID-19 pandemic. Sweetgreen’s focus on locally sourced quality ingredients has built it into a national brand with more than 200 restaurants across the US. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit Read the transcript: https://www.thespl.it/p/the-peel-episode-1-building-mcdonalds In this episode, we discuss: - How the restaurant industry actually works - How the US food system leads to over $2 trillion in indirect healthcare and environmental costs - Sweetgreen’s origin story - The early constraints that led to Sweetgreen’s ingenious business model - Launching a music festival headlined by Kendrick Lamar, The Weeknd, and The Strokes - Killing a major product line to double down on online ordering in 2015 - How to build an enduring brand - Sweetgreen’s new salad subscription and gamified loyalty program - The surprising benefits of Sweetgreen’s new automated Infinite Kitchen - How the best entrepreneurs never give up Where to find Jonathan: Twitter https://twitter.com/jonnynemo LinkedIn: https://www.linkedin.com/in/jonathan-neman-9a28aa8/ Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Timestamps: (2:35) The state of the restaurant industry since 2007 (6:03) How COVID-19 changed the restaurant industry (9:05) The bad incentives holding back the US health system (10:58) How Sweetgreen built a local AND national brand (13:07) How he made $40,000 a year in high school (15:30) How a stint in Australia inspired Sweetgreen (17:45) Sweetgreen’s 50-person friends & family round (20:14) Challenges of opening the first restaurant (21:58) How a tiny 500-square-foot restaurant unlocked Sweetgreen's success (22:50) When sales suddenly dropped 70% (23:40) The moment he realized he wanted to start his own business (26:23) Opening early restaurants during the Global Financial Crisis (27:35) Using a farmer's market to start a music festival and promote Sweetgreen (29:49) Landing Kendrick Lamar, The Weeknd and The Strokes as festival headliners (32:41) Why they shut down their second-largest product line (35:16) Launching Sweetpass (a gamified loyalty program) (38:19) Launching Infinite Kitchen (a fully automated restaurant) (42:05) Online ordering trends (44:13) The challenge with customizable food (45:36) Using automation to reduce preparation error rates (46:50) Acquiring a startup built by MIT grad students (49:04) The surprising benefits of Infinite Kitchen (52:25) The key to making healthy food accessible (53:30) Unfortunate facts of the US food system (57:25) How to “do the right thing” AND maximize profits (59:58) His favorite board game is... (60:52) We need to stop glamorizing overnight success Read the full transcript: https://www.thespl.it/p/the-peel-episode-1-building-mcdonalds Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
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