Sheel Mohnot is the Co-founder of Better Tomorrow Ventures, an early stage fintech focused fund leading rounds in pre-seed and seed-stage companies.
Our conversation weaves through Sheel’s two decades of building and investing in fintech, starting BTV, and why they started a fintech-focused accelerator, The Mint.
Fun facts on Sheel, he was a contestant on the Zoom Bachelor during COVID lockdowns, in a Justin Bieber music video, got married in the Taco Bell Metaverse, and was once banned from Uber.
We talk lessons competing against Stripe before selling his first company, common fintech startup pitfalls, and the trick every VC should use when fundraising.
Timestamps:
(00:00) Intro
(03:13) Why fintech makes disproportionate positive change
(07:49) Most interesting opportunities in fintech today
(09:09) The accountant shortage
(12:59) Common early fintech startup pitfalls
(16:09) Building Fee Fighters to cut payment processing fees
(21:15) Lessons competing with Stripe
(21:57) Getting acquired by Groupon and adding $600m in market cap
(25:11) Biggest first-time startup mistakes
(29:21) Getting $10k in Uber credit via paid Google ads
(32:13) Investing in Flexport
(36:19) Navigating hot vs underhyped rounds
(43:39) Sheel’s domain auction company
(53:18) How he started angel investing
(54:57) Spotify acquiring his podcast “The Pitch”
(59:55) Why accelerators succeed and fail
(01:06:07) The Mint, BTV’s fintech-focused accelerator
(01:09:56) Camp BTV in the Santa Cruz Mountains
(01:11:41) Early days of NerdWallet
(01:14:55) Raising $75m BTV Fund 1 with Jake to fill a gap in the market
(01:18:36) Understanding Fund of Funds incentives
(01:22:15) References in VC fundraising
(01:24:02) $150m BTV Fund 2
(01:27:13) Importance of following-on when leading rounds
Referenced:
BTV: https://www.btv.vc/ 
The Mint: https://www.themint.vc/ 
Fee Fighters: https://techcrunch.com/2011/09/23/feefighters-launches-payment-gateway-samurai/ 
Follow Sheel:
Twitter: https://x.com/pitdesi 
LinkedIn: https://www.linkedin.com/in/smohnot/ 
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/ 

Chris Hulls is the co-founder and CEO of Life360, the social network for families. At the time of recording, its the 15th largest app in the US, with over $330 million in annual revenue, and valued at over $3 billion in the public markets.

We go inside the two decade journey building Life360, competing against Sam Altman and Woz, almost getting cancelled on TikTok, and going public twice - first in Australia, then again in the US.

Timestamps:
(00:00) Intro
(02:04) Why CEO’s are getting more authentic
(04:59) Building a social network for family
(08:14) Starting Life360 after Hurricane Katrina
(12:23) $30k from mom and a professor
(13:52) $300k grant from Google
(16:13) Launching on the first Android phones
(18:20) Competing against Sam Altman, Steve Wozniak
(19:06) “If we trusted the data, we would’ve shut down”
(24:22) Why doubters lead to less competition
(25:49) Fundraising in an unsexy market
(32:21) Almost getting cancelled on TikTok
(41:42) Building a contextual advertising business
(48:36) Acquiring Tile, launching hardware products
(52:41) Defeating patent trolls
(57:22) IPO’ing in Australia and the US
(01:01:00) Why its hard to go public below a certain size
(01:07:50) 70% drop in downloads during COVID
(01:10:03) Get to know your competitors
(01:15:05) Lean Startup philosophy went too far

Referenced:
Try Life360: https://www.life360.com/ 
Wheels of Zeus: https://en.wikipedia.org/wiki/Wheels_of_Zeus 
Chris’ TikTok journey: https://www.entrepreneur.com/leadership/how-life360s-founder-dealt-with-teens-mocking-him-on-tiktok/457879 
Chris’ TikTok: https://www.tiktok.com/@life360ceo 

Follow Chris:
Twitter: https://x.com/ChrisHulls 
LinkedIn: https://www.linkedin.com/in/chrishulls/ 

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/ 

Joseph Nelson is the Co-founder and CEO of Roboflow, making the world programmable by building computer vision tools for developers and enterprises.

We talk about how computer vision creates a new paradigm to program the world, and how visual AI is the missing piece of AGI.

Joseph also shares multiple live product examples, how computer vision unlocks new data sources, lessons from Stripe and Palantir, building business models in developer tools, his experience working with David Sacks, and developer marketing tactics and how Roboflow consistently gets to the front page of Hacker News.

Timestamps:
(00:00) Intro
(03:34) Computer vision is the missing piece for AGI
(05:59) Vision as a new paradigm to collect data
(10:55) Live examples of computer vision
(13:45) How a Magic Sudoku solver app led to Roboflow
(18:13) Using computer vision for automation
(24:49) Computer vision in sports
(27:02) How vision unlocks new data sources
(28:24) Inside developer tool business models
(33:32) The "Collison Install" and hands-on customer service
(36:45) When to adopt Palantir's Forward Deployed Engineers
(43:44) Why AI companies need to combine PLG and enterprise sales
(50:12) Advice on developer marketing
(52:30) Roboflow's greatest hits on Hacker News
(01:02:19) Benefits of David Sacks as AI & Crypto Czar
(01:05:32) Why all new technology has bad actors
(01:07:07) Why over-regulation holds back innovation
(01:12:01) How to get on the front page of Hacker News
(01:19:43) Multi modality, time recognition, and agentic vision
(01:28:36) Image-to-image prompting
(01:30:42) Growing up in Iowa
(01:32:20) Making TI-84 calculator games in high school
(01:36:32) Pioneer: hunger games for startups
(01:40:16) Why Roboflow does weekly Ship Lists + Ship and Tell
(01:42:46) Hiring former founders and "full stack people"
(01:45:16) Designing a bottoms-up organization while scaling
(01:50:35) Why candidates build with Roboflow in hiring process
(01:55:08) Hiring someone to help with the podcast

Referenced:
Robowflow: https://roboflow.com/ 
Roboflow Universe: https://universe.roboflow.com/ 
Paint.wtf: https://paint.wtf/ 
Roboflows NeurIPS Presentations: https://blog.roboflow.com/neurips-2023-papers-highlights/ 
Careers at Roboflow: https://roboflow.com/careers 

Follow Joseph:
Twitter: https://x.com/josephofiowa/ 
LinkedIn: https://www.linkedin.com/in/josephofiowa 

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/ 

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

OpenPhone: https://openphone.com/

Follow Daryna:

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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:

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/