Episoder
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Sam Ross is the Co-founder and CEO of Numeral.
This conversation is a master class on all things growth at the zero to one stage. We talk early growth lessons from Airbnb, and stories from being one of the largest, earliest Facebook advertisers.
We get into working backwards from pockets of strong demand to find business ideas, how to establish early social proof around your product, why you shouldnât hire a growth person as your first growth hire, how he raised Numeralâs Series A in four days, and why sales tax is so complicated and how theyâre using AI to make it easy.
Timestamps:
(3:03) Why sales tax is so complicated
(8:06) Running crazy Facebook ads in 2013
(11:58) Why you need to be aggressive on new growth channels
(16:55) How strong retention unlocks massive businesses
(18:24) Using pockets of demand to find business ideas
(21:34) Balancing performance vs brand marketing
(25:45) How to build a brand from scratch
(29:11) When cold outbound actually works
(36:18) Building early social proof around your product
(43:33) Donât hire career growth people for growth roles
(49:31) Lessons building a jewelry business doing $30m in revenue
(58:44) How the 2018 Wayfair v South Dakota decision led to Numeral
(1:05:04) Hacking an early product together with spreadsheets
(1:07:32) Automating the product
(1:15:26) What happens if you donât pay sales tax
(1:20:41) How Numeral uses AI and LLMs internally
(1:26:41) How to compete against non-technical incumbents
(1:32:57) Why they raised VC for Numeral
(1:38:19) Raising a Series A in four days
(1:45:43) How big can a sales tax company really be?
(1:48:55) Creating a better global tax system
(1:54:31) How San Francisco is losing its soul
Referenced
Check out Numeral: https://www.numeralhq.com/
South Dakota v Wayfair: https://en.wikipedia.org/wiki/South_Dakota_v._Wayfair,_Inc.
Follow Sam
Twitter: https://x.com/SpamRoss
LinkedIn: https://www.linkedin.com/in/sambross/
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/
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Spenser Skates is the Co-founder and CEO of Amplitude.
Our conversation gets into the importance of data in product design and company building, how Amplitude is thinking about AI, and the future of user responsive software.
We also get into the early days of building Amplitude, when to go multi-product, how to construct your board as a startup, hiring executives at various company stages, lessons from closing three acquisitions, lessons scaling to $300 million in ARR, inside Amplitudeâs 2021 IPO, and what most people get wrong about Founder Mode.
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel
Timestamps:
(4:45) Using data to build great products
(8:31) Why data is existential to every business
(13:14) How to go multi-product
(15:48) Every startup becomes a distribution company
(19:29) Lessons from three acquisitions
(29:09) AI hasnât changed B2B SaaS yet
(31:24) Challenges of incorporating AI in B2B SaaS
(33:09) Amplitudeâs AI experiments
(36:29) Navigating technology hype cycles as a public company
(39:40) Amplitudeâs opportunity in LLMs
(43:08) User responsive software
(46:16) Surprising things that slow your speed of execution
(51:27) What people get wrong about Founder Mode
(59:48) Pivoting into Amplitude after YC
(1:04:42) Nine months to raise Amplitudeâs first round
(1:08:31) Surprises from closing the first customers
(1:12:46) Two sales lessons for technical founders
(1:13:44) Scaling to $300M+ ARR
(1:17:14) How to choose board members
(1:19:55) Inside Amplitudeâs IPO
(1:21:56) âStock price is an output of the businessâ
(1:26:36) Evolving from startup founder to public company CEO
(1:31:54) How hiring execs changes as you scale
(1:34:32) Why DEI is important at Amplitude
(1:39:46) Relevance of gaming and startups
Referenced
Try Amplitude: https://amplitude.com/
Careers at Amplitude: https://amplitude.com/careers
Moxie Marlinspikeâs web3 article:https://moxie.org/2022/01/07/web3-first-impressions.html
Sheep Logic: https://www.epsilontheory.com/sheep-logic/
Follow Spenser
Twitter: https://x.com/spenserskates
LinkedIn: https://www.linkedin.com/in/spenserskates
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/
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Manglende episoder?
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Dan Lorenc is the Co-founder and CEO of Chainguard, the safe source for open source.
The internet runs on free, open source software. But as its risen in popularity, its become the latest attack point targeted by hackers and nation states.
This conversation with Dan gets into the history of open source software, cloud computing, Linux, the software supply chain, how AI will impact it, and what the next big cyber attack will look like.
Dan is an engineer, but he also loves sales and go-to-market. We unpack how Chainguard went from zero to 150 customers and a $40m ARR in two years.
Chainguard just announced a $350 million Series D led by Kleiner and IVP, and Dan unpacks the round, plus shares his secret methodology for valuing the company.
A big thank you to Danâs Co-founder Kim Lewandowski, to Clay Fischer @ Spark, Bogomil Balkansky & Andrew Reed @ Sequoia, and Tom Loverro @ IVP for their help brainstorming topics for Dan.
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel
Timestamps:
(3:26) A safe source for open source
(4:57) The software supply chain
(7:19) Can you trust open source code with contributors in Russia?
(9:43) Malware attack that almost took down the entire internet
(12:40) What the next big cyber attack will look like
(15:12) How will AI impact the software supply chain
(17:53) The history of cloud computing
(21:42) Why all cloud computing runs on Linux
(23:16) How Linux + Linux distros work
(29:28) Automating open source security
(32:43) Chainguard roadmap: Libraries and VMs
(36:40) Focusing on FedRAMP
(42:44) Impact of DOGE
(44:06) Zero to $40m ARR in two years
(45:40) Learning to love sales as a technical founder
(47:24) Lessons from Frank Slootman
(51:15) How to create urgency in sales
(53:16) How to build a sales team
(58:23) Hiring Ryan Carlson from Wiz & Okta
(1:01:45) Inside Chainguardâs $350m Series D
(1:07:41) Vibe coding + Danâs software stack
(1:09:51) Cutting his hair in front of the entire company
(1:10:27) Wearing a different suit to each board meeting
(1:12:32) Bogomil, worldâs best SDR
Referenced
Check out Chainguard: https://www.chainguard.dev/
Jobs at Chainguard: https://www.chainguard.dev/careers
Prior episode with Dan: https://www.youtube.com/watch?v=AC4cOJ9n_Z8
Linux Origin Email: https://www.reddit.com/r/linux/comments/mmmlh3/linux_has_a_interested_history_this_is_one_of/
The Qualified Sales Leader: https://www.amazon.com/Qualified-Sales-Leader-Proven-Lessons/dp/0578895064
Julius, AI data analysis: https://julius.ai/
Claude Code: https://www.anthropic.com/claude-code
Worldâs best SDR: https://x.com/BogieBalkansky/status/1913269714882814350
2025 Chainguard Assemble Keynote: https://www.youtube.com/watch?v=adfU9LJg3I0
Follow Dan
Twitter: https://x.com/lorenc_dan
LinkedIn: https://www.linkedin.com/in/danlorenc/
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/
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Colin Sidoti is the Co-founder and CEO of Clerk, the best way to build authentication and user management.
I loved this conversation, because Colin is currently in the arena building Clerk. It has not been easy, and he takes us inside some of the harder moments of the past six years.
We hit on three main themes: authentication; lessons raising multiple hard Seed extensions in the early days, including a recap before the A, and the demo that got a16z to invest; and things AI and MCP.
We also talk founding a company with his brother, building a compound startup, why components are the new APIs, and what he learned about audacious goals from John Collison @ Stripe
A big thank you to Reid Christian @ CRV, Paul Klein @ Browserbase, and Joseph Nelson @ Roboflow for helping brainstorm topics for Colin.
Timestamps:
(3:39) The best developer tool for authentication and user management
(5:45) The easiest way to set up billing
(7:13) Building a compound startup
(9:15) Lesson on audacious goals from John Collison
(12:40) Developer tools are now trusted category experts
(13:47) How auth impacts billing, CRM, marketing, analytics
(19:44) Why auth is always changing
(25:40) Coming up with the idea for Clerk
(29:24) What its like starting a company with your brother
(30:58) Living in a basement during Clerks early days
(35:33) Getting early users narrowing focus in South Park Commons
(40:10) Fundraising lessons from struggling to raise
(43:46) The trick that raised Clerkâs first round from S28
(45:09) Launching + the first Seed extension
(50:15) Sequoiaâs feedback that improved conversion rates
(52:22) Why a16z led Clerkâs 2nd Seed extension
(58:11) How to do a recap before Series A
(1:03:34) Changing Clerkâs pitch to scare investors
(1:08:56) Fundraising advice âWhy partner alignment is all that mattersâ
(1:11:42) Fast Series A and breaking 7%/week growth
(1:16:32) Negotiating Clerkâs Series B at the bar
(1:22:15) Investors in the arena vs in their mansions
(1:27:57) The three ways AI is changing authentication
(1:31:21) Why AI agents all try to steal free AI credits
(1:33:09) Remember to have fun
(1:36:24) Building a better product to compete in a crowded market
Referenced
Try Clerk: https://clerk.com/
Jobs at Clerk: https://clerk.com/careers
Martin Casadoâs tweet https://x.com/martin_casado/status/1558134697753841664
Try Inngest: https://www.inngest.com/
Follow Colin
Twitter: https://x.com/tweetsbycolin
LinkedIn: https://www.linkedin.com/in/colin-sidoti-751a219
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/
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Filip Kaliszan is the Founder & CEO of Verkada, the physical security company.
Verkada started in 2016 by building the best camera for physical security teams, and has since evolved into a full suite of security products for buildings. Filip takes us inside Verkadaâs rapid growth to almost a billion in annual revenue, over 2,000 employees, and raising capital from investors like Sequoia, Meritech, First Round, General Catalyst, and Next47.
We get into how AI and LLMs are changing hardware, the power of customer therapy, how Filip iterated on early startup ideas, inside Verkadaâs very difficult first funding round, how signing their first big customers changed the trajectory of the business, and how to think about adding new products over time.
We also talk through Verkadaâs commitment to in-person work in the summer of 2020, how you should evaluate joining a startup as an employee, Verkadaâs âsoftware zeroâ employee bonus policy, and building a rooftop bar for the office.
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel
Timestamps:
(4:20) Verkada, the physical security technology company + Demo!
(11:02) Building software powered hardware
(12:56) LLM opportunities in cameras
(15:49) Filipâs lifelong fascination with photography
(17:57) Taking one year to come up with the idea for Verkada
(22:27) Building his own home security system to learn the $16B market
(27:14) Why hardware experimentation is cheaper and easier than youâd think
(30:36) The importance of customer therapy
(32:37) How to get your first customers, importance of quick time to demo
(35:06) Why early fundraising was so hard
(40:38) Verkadaâs first big customer
(42:23) How to decide what startup to join
(45:45) The opportunity in âsmart building techâ
(50:34) How to launch new product lines
(58:07) Re-architecting the security industry to be software-native
(1:02:31) How hiring and managing a team changes as you scale
(1:08:55) Why each team at Verkada has its own recruiters
(1:14:00) Adding senior leaders to the team as you scale
(1:17:06) Evolving from introverted engineer to CEO of multi-thousand person company
(1:21:59) Verkadaâs cool office and focus on in-person work during COVID
(1:28:12) Building a rooftop bar on the office
(1:32:20) Verkadaâs Software Zero employee bonus program with 40x ROI
(1:36:00) How Filip thinks about IPO vs staying private
Referenced
Verkada: https://www.verkada.com/
Open roles at Verkada: https://www.verkada.com/careers/
Follow Filip
LinkedIn: https://www.linkedin.com/in/kaliszan/
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/
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Ofek Lavian is the Co-founder and CEO of Forage, the mission driven payments company.
This is a special episode, because Iâm an investor in Forage, and Ofek shares everything heâs learned building the company. We go deep on food stamps, also known as EBT or SNAP, the government program that provides over $200 billion dollars per year in benefits that help 42 million low income Americans buy food.
Our conversation gets into lessons from Ofekâs time leading payments teams at Uber and Instacart, building Instacartâs EBT program up to 40 employees and 10% of its total revenue, and why Ofek is so passionate about helping low income Americans.
We get into the history of food stamps, market dynamics that led to low online adoption, the days Ofek thought Forage might not make it all the way to now working with the biggest players in online grocery, like Uber and DoorDash, and the long-term opportunity Forage has to build the rails the government uses to distribute trillions of dollars of restricted consumer benefits.
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel
Timestamps:
(4:53) Forage: Helping 42m Americans buy food
(5:24) History of food stamps & EBT
(9:26) Growing up as an immigrant family with low food access
(11:39) 90% of EBT recipients are elderly, disabled, or working parents
(12:39) How Forage sells revenue to its customers
(14:15) Building Instacartâs EBT program during COVID
(18:25) Why no one built an EBT payments product
(22:13) Joining Forage as a Co-founder
(25:01) Why government payments are so hard
(30:25) Growing 15x in six months
(33:52) Underdiscussed mental health challenges of startups
(37:06) How the political environment impacts EBT
(43:20) Why Forage charges more than competitors
(45:58) Seasonality in EBT spend
(46:59) Why early investors passed on Forage
(48:10) The trillion dollar opportunity in restricted payments
(50:56) ââThere's no single idea that has destroyed more business value on planet Earth than the idea that micromanagement is bad.â
(54:45) Why Forage doesnât care about job titles
(58:51) Lessons backpacking across 28 countries after college
(1:02:09) How to travel on a budget
(1:04:24) Importance of health
(1:06:15) Saving a friends life on Mount Everest
Referenced
Forage: https://www.joinforage.com/
Ofekâs viral tweet: https://x.com/OfekLavian/status/1766950034581700697
Follow Ofek
Twitter: https://x.com/OfekLavian
LinkedIn: https://www.linkedin.com/in/ofeklavian/
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/
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Ed Lando is the Co-founder of Pareto, where heâs been an early investor in over 25 unicorns, started and incubated over 10 companies, and was recently named the most active angel investor in the world according to Crunchbase.
We get into how Ed first got started angel investing, how he built up deal flow, why heâs historically kept a low profile, and why he hasnât raised outside capital.
We also talk concentration vs diversification, why thereâs many ways to build successful companies, advice on hiring your first employees, and his playbook for incubating companies at Pareto, which is where he focuses most of his time.
Timestamps:
(0:00) Intro
(2:51) Getting into angel investing
(3:58) Debating high vs low PR strategies
(8:27) How to start building deal flow when angel investing
(10:00) Pareto: first investor in people leaving school or their job
(12:05) Evolving from angel to fund
(14:57) Why Ed didnât raise outside capital
(20:33) Concentration vs diversification
(28:29) Investing in non-sexy categories
(32:50) Thereâs no one right way to build a company
(36:03) When to go against traditional wisdom
(39:36) Lessons from his anti-portfolio
(45:59) Edâs close relationship with his parents(
(49:04) How weâre using AI
(54:04) Incubating companies
(58:38) Investing beyond spreadsheets and DCF models
(1:05:49) How to trust your intuition investing
â(1:09:47) How to move fast
(1:14:24) What most people get wrong when incubating companies
(1:18:40) How to hire your first employees
(1:26:27) Navigating hype when building and investing
1:29:59 Venture math and the Power Law
1:35:33 How Ed and Paretoâs strategy might break
1:38:45 Differences between the US and Europe
Referenced
Pareto: https://pareto20.com/
Misfit Market: https://www.misfitsmarket.com/
Catalina Crunch: https://catalinacrunch.com/
Zamp: https://zamp.com/
Magnus Carlsen on Joe Rogan: https://www.youtube.com/watch?v=ybuJ_nIXwGE
Follow Ed
Twitter: https://x.com/edwardlando
LinkedIn: https://www.linkedin.com/in/edwardlando/
Substack: https://edwardlando.substack.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/
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Tommy Nicholas is the Co-founder and CEO of Alloy, the identity and fraud prevention platform trusted by over 700 financial service companies.
Our conversation explores the early days of fintech, why more consumer financial protections actually lead to more fraud, and gets into the weeds of various tactics heâs learned building a technical platform company like Alloy.
We talk about embracing that the hard parts of company building are actually the best parts, why youâre most likely to give up when things first start getting better, using hands-on sales implementations in the early days to gave Alloy product market fit on steroids, how hiring changes as you scale, getting 100âs of noâs over 20 months raising their Seed round, and why TAM doesnât matter.
Thanks to Charley Ma for his help brainstorming topics for Tommy!
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try them here: https://bit.ly/NumeralThePeel
Timestamps:
(3:56) The platform to manage fraud
(5:48) What fintech risk was like in the early 2010âs
(14:34) Why company building never gets easier
(19:30) Reasons the hard stuff is actually the good stuff
(24:00) Youâre most likely to give up when things start getting better
(33:47) Doing hands-on sales implementation to get PMF on steroids
(42:26) Deciding when PLG or hands-on sales will work best
(52:33) Why more consumer financial protections leads to more fraud
(58:14) 20 months to raise $2m vs $200m from a spreadsheet
(1:06:32) âMake yourself look like a good investmentâ
(1:10:14) Why TAM doesnât matter
(1:14:35) How to hire collaborative problem solvers
(1:24:38) Why Alloy didnât do much marketing early on
Referenced
Try Alloy: https://www.alloy.com/
Charley Maâs Pod Episode: https://youtu.be/5cxgB1_q2lw
Try Artie: https://www.artie.com/
Follow Tommy
Twitter: https://x.com/tommyrva
LinkedIn: https://www.linkedin.com/in/tommynicholas
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/
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Mike Murchison is the Co-founder and CEO of Ada, the AI-powered customer service automation platform.
Adaâs product and scale puts Mike at the forefront at how AI is changing software and labor markets, and this conversation felt like both a glimpse into the future, and a look into the past, at a story of pure grit and determination, working seven customer service jobs at once.
We talk about why management capabilities becomes even more important in AI-native companies, how customer service is changing from a cost center to a revenue driver, and how to talk to customers more as you scale.
We also get into why AI is still underhyped, what truly AI native software looks like, the realities of selling enterprise AI software today, and advice for anyone building an AI agent from scratch.
Thanks to Boris Wertz and Fahd Ananta for their help brainstorming topics for Mike!
Timestamps:
(00:00) Intro
(03:49) Making customer service extraordinary for everyone
(05:44) Management becomes more important in AI-first companies
(12:13) From customer inquiry to solution in production, fully autonomously
(16:01) Why companies talk to customers less as they grow
(20:36) Creating new products from customer service data
(22:45) Broken incentives in customer service
(26:10) Working 7 customer service agent jobs at once for a year
(37:19) Why pivoting to Ada felt like failure
(46:11) How Mike would build an AI agent from scratch today
(49:15) Ways AI will change how we build and manage companies
(56:44) Why the best managers are great users of AI
(1:00:27) How the top 1% of people are using LLMs
(1:06:22) Realities of selling enterprise AI software today
(1:11:02) Building a sales team from scratch
(1:15:21) Reflecting on Adaâs scale + doubling the last six months
(1:16:41) Biggest software category of all-time ($750B)
(1:19:51) Why AI is still under hyped
(1:21:01) Ego is the biggest inhibitor to AI adoption
(1:23:33) How AI will fuel explosion of creativity and productivity
(1:25:20) Large companies will benefit the most from AI
(1:27:41) Multi-modal language models and autonomous (computers
Referenced
Try Ada: https://www.ada.cx/
Follow Mike
Twitter: https://twitter.com/mimurchison
LinkedIn: https://www.linkedin.com/in/mikemurchison
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/
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Cam Doody is the Co-founder and General Partner of Brickyard, the venture capital firm moving founders to Chattanooga, Tennessee to lock-in with no distractions until they find product market fit.
Brickyard is one of the most unique venture firms youâll ever come across, and we get into how it how it was inspired by a 16x fund based in Chattanooga, why Cam and his co-founders started it during ZIRP, and why they hope everyone copies their model.
We also get into Camâs startup Bellhops, which he started in 2011 and has since grown into the third largest moving company in the US. We talk running a local services business, why 5-star review systems donât work, and how U-Haul almost killed Bellhops overnight back in 2016.
Thanks to Nader Khalil, Matt Harb, Austin Beveridge, and Spencer Levitt for their help brainstorming topics for Cam!
Timestamps:
(0:00) Intro
(03:33) Chattanooga: Dirty manufacturing city to high tech
(05:23) Brickyardâs precursor, the Lamp Post Group (a 16x fund)
(09:46) How ZIRP screwed up early stage investing
(13:49) What is Brickayrd?
(21:14) Getting Brickyard off the ground in 2021
(26:25) 100+ year old rug warehouse + maintenance nightmares
(33:13) Cam wants everyone to copy Brickyard
(36:31) Why economic development startup programs donât work
(38:59) YC teams doing Brickyard to escape the Trough of Sorrow
(44:07) How Brickyard companies raise Series As
(46:10) Nvidia acquiring Brev
(52:18) How to deal with a co-founder breakup
(55:45) Starting Bellhop to build a better moving company
(1:02:27) How U-Haul almost killed them overnight
(1:06:54) Marketing tactics for a local services business
(1:12:05) Why 5-star review systems donât work
(1:18:16) How Camâs view of VCâs changed after becoming one
(1:20:37) Ways VCâs actually add value
(1:25:05) The thesis for Bitcoin
(1:39:21) Camâs annual remote desert island vacation
Referenced
Check out Brickyard: https://www.justlaybrick.com/
The Trough of Sorrow: https://andrewchen.com/after-the-techcrunch-bump-life-in-the-trough-of-sorrow/
Bellhops: https://www.getbellhops.com/
Follow Cam
Twitter: https://www.twitter.com/camdoody
LinkedIn: https://www.linkedin.com/in/cam-doody-b489a124
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/
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Eric Simons is the Co-founder and CEO of StackBlitz, best known for its breakout product Bolt, letting anyone build full stack apps from text, in the browser.
Bolt launched in October of 2024, quickly growing from zero to a $20 million revenue run rate in two months, making it one of the fastest growing products ever. But Eric will be the first to tell you it wasnât an overnight success - the product didnât even work the first time they tried building it.
We go behind the scenes of the seven year journey building the tech that eventually led to Bolt, how to avoid distractions, being capital efficient, living in a frat house for $100/month, and squatting in AOLâs headquarters for $1/day when he was 19.
Eric also takes us inside the weeks after Boltâs viral launch, figuring out a new business model on the fly, his strategy for fundraising and PR, why you should open source your code, Boltâs playbook for building a community around the product that enabled their viral launch, and how AI is changing software forever.
Timestamps:
(0:00) Intro
(2:24) Building full stack apps from text, in your browser
(4:19) Running an operating system in the browser
(11:48) Why Bolt failed the first time, almost shutting down the company last summer
(20:18) How Bolt went viral from one tweet
(28:33) Differences between ChatGPT, Claude, Cursor
(39:38) Why AI code gen changes the software world order
(42:01) What happened inside Bolt going from zero to $20m ARR in two months
(47:32) Not sharing fundraises publicly + his PR strategy
(58:57) Why the team never gave up for seven years
(1:01:07) Living in a frat house for $100/month
(1:04:07) How to be capital efficient
(1:09:00) Living on $1/day in AOLâs HQ when he was 19
(1:14:01) Inside Boltâs Series B
(1:21:03) Boltâs hiring and product roadmap
(1:32:58) Creating a new inference-based AI business model
(1:38:07) Eric's playbook for building a community of users
(1:44:05) Why you should open source your code
Referenced
Try Bolt: https://bolt.new/
Bolt on X: https://x.com/boltdotnew
Check out Webcontainers: https://webcontainers.io/
$0 to $4m ARR case study with Anthropic: https://www.anthropic.com/customers/stackblitz
Boltâs open source code: https://www.bolt.diy/
Bolt / StackBlitz is hiring! https://stackblitz.com/careers
Ericâs favorite cafe, The Lighthouse SF: https://thelighthousessf.com/
Lady Gagaâs âone personâ montage: https://www.youtube.com/watch?v=iRxsX_30tjs
Living inside AOL HQ at 19 years old: https://www.cnet.com/tech/tech-industry/meet-the-tireless-entrepreneur-who-squatted-at-aol/
Bloomberg coverage of StackBlitz Series B: https://www.bloomberg.com/news/articles/2025-01-21/ai-speech-to-code-startup-stackblitz-is-in-talks-for-a-700-million-valuation?embedded-checkout=true
Joel Spolskyâs blog: https://www.joelonsoftware.com/
Follow Eric
Twitter: https://x.com/ericsimons40
LinkedIn: https://www.linkedin.com/in/eric-simons-a464a664/
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/
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Rick Zullo is the Founder of Equal Ventures. Our conversation gets into Equalâs unique approach to venture capital, thinking more like public market and private equity investors, and why they also think traction is overrated at Seed.
We talk through Equalâs thesis-driven model, employing a team of product owners, only investing in only 3 to 5 themes at once, and Rickâs admiration of Charlie Munger.
We also talk AI - who will benefit the most, what he does and doesnât like in terms of investing in the space, why venture capital is not really venture capital anymore, and why it sucks to be a Seed investor right now.
Rick also runs the Emerging Manager Circle, a group for emerging fund managers. We get into the origin story of the group, his own struggles raising his first fund, and why talent is leaving the mega funds.
Timestamps:
(00:00) Intro
(03:38) Why venture capital isnât venture capital anymore
(11:33) How founders should approach raising a Seed round
(14:13) The realities of downrounds
(15:55) Rickâs favorite founders that raised little capital
(18:54) Biggest fundraising mistake founders make
(21:21) Why we need to stop funding AI companies
(28:34) How AI will benefit private equity the most
(33:30) Three levels of opportunity in AI right now
(38:36) Why traction is overrated at Seed
(41:38) Investing in businesses with compounding returns on capital
(52:07) VC lessons from PE firms
(56:24) Why Seed investing sucks right now
(1:04:15) The beauty of small exits
(1:12:52) How failing to start a fund in college led to Equal Ventures
(1:20:06) The struggle raising Equalâs $55m Fund 1
(1:23:23) Why the best talent is leaving mega VC firms
(1:30:16) The Emerging Managers Circle
Referenced
* Equal Ventures: https://www.equal.vc/
* EMC Summit: https://www.emcsummit.com/
Follow Rick
Twitter: https://x.com/Rick_Zullo
LinkedIn: https://www.linkedin.com/in/rickzullo/
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/
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Villi Iltchev is the founder of Category Ventures, where he invests early in enterprise software startups. And heâs done it longer than almost anyone, building Salesforceâs corporate venture arm and investing early in companies like Airtable, Zapier, GitLab, Remote, Hubspot, Gusto, and Box.
Fresh off raising his $160m Fund 1, we get into the opportunity he saw to start Category, and how San Francisco and Silicon Valley have changed over the past 30 years.
He also shares his story growing up as an illegal immigrant in Greece, moving to the US by himself in high school, the biggest mistake of his career, advice for founders selling their company, why unit economics and profitability always matters, how developer tools went from terrible to amazing businesses, the mistake that almost killed GitLab after he invested, and why you should raise your seed round from a seed fund.
Timestamps:
(00:00) Intro
(03:22) Illegally immigrating from Bulgaria to Greece
(05:14) Moving to the US by himself in high school
(13:15) Moving to SF in the Dot Com Bubble
(15:49) How SF changed over the last 25 years
(22:27) Why HP fell from the top of Silicon Valley
(25:36) Building Salesforceâs corporate VC arm
(30:29) Why SaaS was so transformative
(34:35) Angel investing in Airtable
(39:52) The biggest mistake of his career
(42:13) Why unit economics always matter
(47:20) Biggest mistake when selling a tech company
(49:00) Almost starting a software PE firm and landing in VC
(55:45) Lessons from August Capital + Evolution of venture
(59:22) Early days of dev tools + Investing in GitLab
(1:09:50) Why being contrarian is dumb
(1:11:45) How GitLab almost died and emerged stronger
(1:16:48) Villiâs journey to starting Category
(1:25:22) Categoryâs thesis
(1:30:48) Why startups always come in batches
(1:31:57) The importance of track record in venture
(1:35:32) Deciding a $160m fund size
(1:39:26) Why you should raise seed rounds from seed firms
(1:43:40) What Villi looks for in a startup
Referenced
Category VC: https://www.categoryvc.com/
Categoryâs $160m Fund 1: https://www.forbes.com/sites/alexkonrad/2024/12/17/villi-iltchev-raises-160-million-debut-fund-category/
Aaron Levie (Box) on The Peel: https://youtu.be/cLn_tqPvNf4
GitLabâs Recovery Stream: https://www.youtube.com/watch?v=v0TRHLvYGE0
Guy Podjarny (Snyk) on The Peel: https://youtu.be/BzKlZ_v4uCw
Why SaaS wonât consolidate: https://medium.com/@villispeaks/why-saas-consolidation-is-not-happening-2b9b722e0250
Follow Villi
Twitter: https://x.com/villi
LinkedIn: https://www.linkedin.com/in/villi04/
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/
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Rahul Sidhu is the co-founder of SPIDRTech and Aerodome, two companies in the public safety space.
Heâs sold both of them, and our conversation unpacks all the lessons he learned, what he did differently with his second company Aerodome, and why he sold only 17 months after starting it.
If you tuned into last weekâs episode, Paul told us to never talk to the cops. Rahul gives us the other side of the story, sharing his playbook for selling to police, the government, how he met Nikita Bier in high school, and why heâs still bullish on drones, robotics, and AI in the physical world.
Timestamps:
(00:00) Intro
(04:07) What its like testifying to Congress
(08:06) Why 90% of what he knew about police was wrong
(13:15) How to sell to police departments
(15:24) His first business selling WoW accounts
(19:00) Meeting Nikita Bier in high school
(21:29) Starting SPIDRTech to improve police + community relationships
(27:45) Two biggest mistakes building SPIDR
(31:47) How startups break down when scaling
(34:19) Selling SPIDR instead of raising a Series B
(40:12) Why Aerodome was so much easier to start
(42:55) Why Rahul loves unsexy markets with founder market fit
(46:03) Starting Aerodome, drones as first responders
(53:39) Building a capital efficient hardware startup
(56:46) How regulatory changes made an opening for Aerodome
(01:00:13) Inside Aerodomeâs Series A
(01:03:57) Selling Aerodome to Flock Safety within 17 months
(01:09:31) Saying âwould I work for this team?â when getting acquired
(01:14:35) Seeing a homeless guy in an Aerodome shirt
(01:17:02) The massive Robotics + AI opportunity this decade
(01:21:42) Whatâs really happening with drones in New Jersey
Referenced:
SPIDRTech: https://www.spidrtech.com
Aerodome: https://www.aerodome.com/
Nikita Bierâs Ted Talk: https://www.youtube.com/watch?v=k9QTVII_lkg
Follow Rahul:
Twitter: https://x.com/rahoolsidoo
LinkedIn: https://www.linkedin.com/in/rahulsidhu/Follow Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
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Paul Klein is the Founder and CEO of Browserbase, building infrastructure for AI browsers.
Our conversation gets into the future of software and AI agents, why authentication is a huge problem in AI, how the best infrastructure companies become product companies, and the memo he wrote that convinced him to start Browserbase despite not wanting to build another company.
A year ago, Paul was a relatively unknown commodity, and definitely did not want to raise venture capital again. He shares the playbook he used to go from zero to raising $27 million in nine months âas a non-famous personâ (his words).
He shares all his lessons learned in the arena as heâs processing them, like what he thinks will unlock better AI agents, why you should like your own tweets, and how Browserbase competes with incumbents.
Timestamps:
(00:00) Intro
(02:39) How LLMs unlock automation online
(08:34) The future of software (AI agents)
(11:21) Why AI agents need better authentication
(12:59) Lessons from Twilio on building an infrastructure company
(17:27) Learnings from his first startup
(19:56) Bubbles, and how they drive innovation
(20:37) Reasons this moment in AI is special
(29:58) Why technical founders love post-PMF
(31:55) The memo that started Browserbase
(34:09) Why a startup should be a means of last resort
(36:53) Being a solo founder
(42:24) Importance of in-person culture
(45:56) The best place to find engineers
(48:34) How Paul hired a contractor army to build Browserbase
(50:16) Why you canât hire mercenaries
(54:28) The power of emojis in marketing
(57:39) Browserbase's early growth playbook (3 videos)
(01:04:00) Benefits of sharing an office with other startups
(01:06:00) Sales lessons from his parents
(01:08:07) Why startups are like video games
(01:13:43) Successful founders work the hardest and are shameless
(01:18:44) Customer support is a startups greatest differentiator
(01:22:06) Paulâs playbook that raised $27m in nine months as a non-famous person
(01:29:03) How investors make decisions
(01:33:10) Risks help startups avoid competition
(01:36:37) Great infrastructure needs its own frameworks
(01:39:05) Long-term thinking in LLMs will enable mass AI agents
(01:42:21) Avoiding tech debt with AI moving so fast
(01:43:48) Infrastructure companies need to become product companies
(01:46:54) The Sine Wave philosophy to startups
Referenced:
Browserbase: https://www.browserbase.com/
An Internet Browser for AI: https://memos.hawkhill.ventures/p/an-internet-browser-for-ai
Rise of the Product Engineer: https://memos.hawkhill.ventures/p/rise-of-the-product-engineer
Death to the Backend: https://memos.hawkhill.ventures/p/death-to-the-backend
The three Browserbase marketing videos
Pre-Seed: https://x.com/pk_iv/status/1775183751800377344
Seed: https://x.com/pk_iv/status/1798731220005883935
Series A: https://x.com/pk_iv/status/1851270308701106383
Follow Paul:
Twitter: https://x.com/pk_iv
LinkedIn: https://www.linkedin.com/in/paulkleiniv/
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/ -
Youâre probably familiar with Baiju Bhattâs work as the co-founder of Robinhood. But heâs also obsessed with space, and recently started Aetherflux, a space solar power company.
We get into the physics of using lasers to beam solar power to the Earth, Aetherfluxâs early roadmap, and how he went from zero to one going from building software to physical products.
We also talk through the early days of Robinhood, getting turned down by hundreds of early investors, the accidental launch, how to know if you really have product market fit, how Aaron Levie at Box helped get Robinhood.com, the value of creativity and design, Baijuâs philosophies on combining qualitative and quantitative user research, and his favorite animal and classic car. He also tried to cut my hair.
Timestamps:
(00:00) Intro
(02:31) Aetherflux: a space solar energy company
(02:50) Origins of space solar power in the 40's & 70's
(10:31) Safely beaming energy from space to Earth with lasers
(13:46) Building floating space solar farms
(21:27) Aetherflux's early roadmap
(27:08) Growing up with dad as a Physics professor
(32:18) Going zero to one building physical products
(35:15) Baiju's favorite car, attempting a haircut, contemplating mustaches
(38:27) Trying to prove Einstein wrong
(41:42) Meeting Robinhood Co-founder Vlad at Stanford
(44:10) Starting an algorithmic trading company
(46:41) The beginnings of Robinhood
(52:04) Getting turned down by hundreds of early investors
(56:49) How they convinced Tim Draper to invest
(59:39) Getting Robinhood.com because of Aaron Levie
(01:01:28) Accidentally launching on a Friday afternoon
(01:03:09) How to know if you have Product Market Fit
(01:06:35) Combining qualitative and quantitative user research
(01:14:23) Loving cats despite being allergic
Referenced:
Robinhood: https://www.robinhood.com
Aetherflux: https://www.aetherflux.com/
TechCrunch coverage: https://techcrunch.com/2024/10/09/billionaire-robinhood-co-founder-launches-aetherflux-a-space-based-solar-power-startup/
Seinfeld mustache scene: https://www.youtube.com/watch?v=DzZsLaLChRg
The MichelsonâMorley experiment: https://en.wikipedia.org/wiki/Michelson%E2%80%93Morley_experiment
Episode with Aaron Levie @ Box: https://www.youtube.com/watch?v=cLn_tqPvNf4
Follow Baiju:
X/Twitter: https://x.com/BaijuBhatt
LinkedIn: https://www.linkedin.com/in/bprafulkumar
Follow Turner:
X/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/ -
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 Sheelâs 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) Sheelâs domain auction company
(53:18) How he started angel investing
(54:57) Spotify acquiring his podcast âThe Pitchâ
(59:55) Why accelerators succeed and fail
(01:06:07) The Mint, BTVâs 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 CEOâs 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) âIf we trusted the data, we wouldâve shut downâ
(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) IPOâing 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 farReferenced:
Try Life360: https://www.life360.com/
Wheels of Zeus: https://en.wikipedia.org/wiki/Wheels_of_Zeus
Chrisâ TikTok journey: https://www.entrepreneur.com/leadership/how-life360s-founder-dealt-with-teens-mocking-him-on-tiktok/457879
Chrisâ 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 Brewâs first viral Instagram post
(40:37) Acquiring subscribers for two cents on Instagram Stories
(42:29) Nik Sharmaâs 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 Alexâs 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: â https://www.morningbrew.com â
Try Oceans: â https://www.oceanstalent.com/ â
Kevin Espiritu episode: â https://www.youtube.com/watch?v=FefGL-qPzDoâ
Craig Fuller episode: â https://www.youtube.com/watch?v=oPPqO8eBq2Mâ
Forbes article: â https://www.forbes.com/sites/hayleycuccinello/2019/02/07/morning-brew/â
Follow Austin:
Twitter: â https://x.com/austin_riefâ
LinkedIn: â https://www.linkedin.com/in/austin-rief/â
Newsletter: â https://www.theaustinbrief.com/â
Follow Turner:
Twitter: â https://twitter.com/TurnerNovakâ
LinkedIn: â https://www.linkedin.com/in/turnernovakâ
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: â https://www.thespl.it/â - Vis mere
