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
Austin Rief is the Co-founder & CEO of Morning Brew, building the Wall Street Journal for the next generation. They started the company in 2017, and grew it to 6 million subscribers and $70 million in revenue in six years.
We talk through the journey starting Morning Brew with Co-founder Alex Lieberman while students at the University of Michigan, and Austin's playbook for starting a new media company from scratch today. We get into the creator economy, early stage investing, ad based business models, being the first advertiser on Instagram Stories, advice for hiring, and his secret for sourcing remote talent in Sri Lanka.
Timestamps:
(00:00) Intro
(03:42) How to start a media company from scratch today
(13:01) Future of the creator economy is niche products
(14:42) Opportunity in B2B media today
(17:05) Reflecting on investing during ZIRP
(21:30) Why its starting to feel like 2021 again
(23:16) Talking VC portfolio math
(27:09) Starting Morning Brew with Wall Street interview prep
(33:35) Being so dumb that they never pivoted from being a newsletter
(35:29) How newsletter business models works
(38:32) Morning Brew’s first viral Instagram post
(40:37) Acquiring subscribers for two cents on Instagram Stories
(42:29) Nik Sharma’s poor mans paid ads strategy
(44:32) Landing Discover as their first big sponsor
(46:06) How agencies and ad buying works
(49:49) Why sales roles are so hard to hire for
(53:04) Importance of offsheet references
(57:43) Sourcing talent in Sri Lanka with Oceans
(01:04:23) Austin and Alex’s unique co-founder dynamics
(01:07:16) Dental plans, rotisserie chickens, and company laptops
(01:10:00) Building WSJ for the next generation
Referenced:
Morning Brew: https://www.morningbrew.com
Try Oceans: https://www.oceanstalent.com/
Kevin Espiritu episode: https://www.youtube.com/watch?v=FefGL-qPzDo
Craig Fuller episode: https://www.youtube.com/watch?v=oPPqO8eBq2M
Forbes article: https://www.forbes.com/sites/hayleycuccinello/2019/02/07/morning-brew/
Follow Austin:
Twitter: https://x.com/austin_rief
LinkedIn: https://www.linkedin.com/in/austin-rief/
Newsletter: https://www.theaustinbrief.com/
Follow Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Niels Hoven is the founder of Mentava, building software to accelerate kids’ education, starting with teaching two year old’s to read.
We talk about how public education isn’t designed for ambitious kids, the power of hater marketing, product design from zero to one, how too much data leads to Frankenstein products, Seed stage fundraising advice, parenting hacks, why AI won’t have a big impact on education, and the future of elite higher ed.
For full show notes, visit: https://highlightai.com/share/0a0869a7-c345-4974-ba2b-726bacf7a534
Timestamps:
(00:00) Intro
(03:49) Why schools don’t challenge overachievers
(11:58) How a hater made Mentava go viral
(18:14) The secret that teaches little kids to read
(24:22) How people actually learn to read
(27:35) 2/3 of 4th graders can’t read proficiently
(29:29) The downfall of one-size fits all education
(33:44) How California almost banned middle school algebra
(40:41) SF’s lottery system and how it impacts low income families
(42:41) How COVID changed education
(47:41) Early prototypes and going all-in on Mentava
(50:56) Best practices from gaming in education
(55:10) Raising a party round from lots of angels
(01:03:03) Designing business models in education
(01:13:19) Being pro-tech + anti-screens for kids
(01:18:04) Top parenting hacks
(01:22:53) How data-driven product design leads to Frankenstein products
(01:25:34) Why gaming’s the best industry to learn how to build product
(01:27:46) The trick Niels used to find startup ideas for 20 years
(01:31:03) Why AI won’t be that impactful in education
(01:36:28) What happens to elite higher education over the next decade
(01:43:15) Admiring Stripe
Referenced:
Mentava: https://www.mentava.com/
Ryan Delk podcast episode: https://open.spotify.com/show/3QqtxGHqsPnKTG4CS7NgX5 | https://youtu.be/GTfsMEOIIxQ
How Neils raised Mentava’s Seed round: https://www.mentava.com/blog/how-i-got-50-high-profile-angel-investors-to-join-our-seed-round
Mentava’s Alphabet Book: https://www.mentava.com/alphabet-sounds-book | https://www.amazon.com/Mentavas-Alphabet-Sounds-Niels-Hoven/dp/B0DKTQ9FW4
Follow Niels:
X / Twitter: https://x.com/NielsHoven
LinkedIn: https://www.linkedin.com/in/nielshoven
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/
Nirav Tolia is the co-founder and two-time CEO of Nextdoor. He started the company in 2011, stepped down as CEO in 2018, watched the company go public in 2021, and re-joined as CEO the summer of 2024. He also founded Epinions which IPO’d in 2004, and before that was an early employee at Yahoo.
We go inside the decision to re-join the company after he thought he’d never come back, and how Nextdoor’s trying to act like a startup while running a public company. He also takes us back to the very early days of Nextdoor, the deliberate product decisions that made growth hard but led to 100M+ neighbors on the platform, the lessons learned operating his first company through the Dot Com Bubble, and what it was like being a guest shark on Shark Tank.
For full show notes, visit: https://highlightai.com/share/d7bcd655-9b2f-47f7-a6e3-fdf3e109c97e
Recommended Podcast:
🎙️Unpack Pricing
Dive into the dark arts of SaaS pricing with Metronome CEO Scott Woody and tech leaders. Learn how strategic pricing drives explosive revenue growth in today's biggest companies like Snowflake, Cockroach Labs, Dropbox and more.
Apple: https://podcasts.apple.com/us/podcast/id1765716600
Spotify: https://open.spotify.com/show/38DK3W1Fq1xxQalhDSueFg
Timestamps:
(00:00) Intro
(02:39) Leaving Nextdoor in 2018
(07:30) Coming back in 2024
(10:31) The importance of family in career decisions
(17:37) Why you have to listen to learn
(24:47) The Founders Mentality
(26:45) “Develop and Deliver”
(32:03) Local, the last remaining consumer opportunity
(36:58) Why being a founder is so hard
(39:21) Going to the high school from Friday Night Lights
(42:07) What Nirav learned at Stanford
(46:22) Working at Yahoo from $500m to $100B
(49:37) Starting Epinions with Naval in 1999
(51:11) Operating through the Dot Com Bubble
(56:34) How Bill Gurley’s challenge led to Nextdoor
(58:16) Early product experimentation
(01:05:19) Why early growth was so hard, and scaling to 100 million neighbors
(01:10:10) The opportunity in local news
(01:12:14) Being a Shark on Shark Tank
Referenced:
Nextdoor: https://nextdoor.com/
The Founder’s Mentality: https://www.amazon.com/Founders-Mentality-Overcome-Predictable-Crises/dp/1633691160
Follow Nirav:
Twitter: https://x.com/niravtolia
LinkedIn: https://www.linkedin.com/in/niravtolia
Follow Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to get new episodes + transcript in your inbox every week: https://www.thespl.it/
Nakul Mandan is the founder of Audacious Ventures. Prior to Audacious, he was a partner at Lightspeed, joining from Battery, which he joined in ‘09 in the middle of the financial crisis while living in India.
This conversation explores his journey immigrating to Silicon Valley and building an early stage venture firm from the ground up.
We get into why most VCs aren’t helpful with recruiting at the zero to one stage, his thesis on starting an early stage venture firm to help founders hire A+ teams, a crash course on early stage recruiting and building a sales team, and how COVID hit right after he left Lightspeed to raise Audacious Fund 1.
Timestamps:
(00:00) Intro
(03:43) Evolution of VC platform teams
(09:53) How Audacious runs in-house recruiting processes
(15:16) The reason large firms can’t help with Seed stage recruiting
(17:06) Immigrating from India to the US mid-financial crisis
(21:59) Silicon Valley's secret weapon
(25:59) The opportunity to start a recruiting-focused Seed firm
(30:14) Raising Audacious $90m Fund 1 in April of 2020
(36:58) The new guard of Seed firms
(39:23) Why $50-75m is the minimum viable institutional fund size
(41:48) How to work with the best founders
(45:30) Navigating deal dynamics, term sheets, and valuations
(52:24) The two hardest parts about starting your own fund
(54:32) Lessons applied raising Audacious $125m Fund 2 in 2023
(58:46) Evolving from a PMF-first to Founder-first investor
(01:02:09) Five traits of force of nature founders
(01:07:05) How to build an A+ team
(01:11:46) The importance of backchanneling
(01:13:54) Why everyone thinks they’re a good people reader
(01:14:35) Two most common mistakes in recruiting
(01:20:59) Determining urgency of a customer’s problem
(01:22:55) Hiring and scaling your first sales team
(01:25:55) Why marketing is the hardest role to hire for
(01:31:59) What good sales people look like
(01:35:43) How to move up market + how to do pilots
(01:43:40) Why Nakul admires Rafael Nadal
Referenced:
Audacious: https://www.audacious.co/
Nakul’s immigration journey: https://www.nakulmandan.com/blog/2024/an-immigrant-living-the-american-dream
Force of nature founders: https://www.nakulmandan.com/blog/2024/traits-i-look-for-in-founders
Early GTM hiring: https://www.nakulmandan.com/blog/2023/initial-gtm-hiring-for-saas-startups
Follow Nakul:
Twitter: https://x.com/nakul
LinkedIn: https://www.linkedin.com/in/nakulmandan
Follow Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it
Jenny Fleiss is the Co-founder of Rent the Runway, and more recently started Roll Rider with her three kids.
We get into the early insights that led to Rent the Runway, building the company with no fashion or tech background, fundraising advice, what she’s thinking about the future of AI and commerce, and the latest company she’s building with her kids, Roll Rider.
For full show notes, visit: https://highlightai.com/share/9bc59c07-05ab-41aa-b37e-f35a7c92092d
Timestamps:
(00:00) Intro
(05:31) How social media was Rent the Runway’s first tailwind
(07:21) Being early to sustainable fashion
(09:21) Starting the company at HBS in 2008
(12:36) Launching with no fashion or tech background
(14:49) The three biggest early surprises
(18:44) Using “show don’t tell” to fundraise
(20:06) Why customer social proof was so important
(23:04) Spending only 10% of revenue on marketing
(25:12) Getting the NYT to cover their launch
(29:43) Early mistakes
(31:29) Re-building the product a few weeks before launch
(33:11) Why building their own logistics was so important
(38:59) Subscriptions, retail, and other key product decisions
(45:15) How the internet makes it harder to shop
(49:30) Building conversational commerce at Walmart
(53:48) Lessons from starting a company with her kids
(58:38) Favorite startups in AI and commerce
Referenced:
Rent the Runway: https://www.renttherunway.com/
NYT’s Launch Coverage: https://www.nytimes.com/2009/11/09/technology/09runway.html
Check out Roll Rider: https://rollrider.com/
Use code TURNER15 for 15% off
Follow Jenny:
Twitter: https://x.com/Jenny_RTR
LinkedIn: https://www.linkedin.com/in/jennifer-fleiss-18577314
Follow Turner:
Twitter: https://x.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/
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, and 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: https://openphone.com/ Ahrefs: https://ahrefs.com/
Follow Daryna: Twitter: https://twitter.com/darynakulya LinkedIn: https://www.linkedin.com/in/darynakulya
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/
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
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it/
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/
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