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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
Garrett Lord is the Co-founder and CEO of Handshake, the career and social network for Gen Z, connecting a million employers, 1,600 universities, and 18 million students and alumni.
We talk through the explosive growth in Handshake’s human AI data labeling business, how AI is changing the job market and careers, advice for scaling a three-sided marketplace, and Garrett’s approach to hiring executive-level talent.
We also get into the early days of Handshake, tapping out his dad’s retirement account to fund the first years, driving across the US landing the first customers, sleeping in McDonald’s parking lots, sneaking into careers fairs, and inside Handshake’s first fundraise that took over seven months.
Shoutout to Jeff Richards, James Alcorn, Ilir Sela, and Ben Christensen for helping brainstorm topics for Garrett.
Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get your $250 here.
Timestamps:
(3:44) More Gen Z than LinkedIn
(7:11) Helping frontier labs label AI data
(14:43) Masters and PhD students flock to Handshake
(16:52) Why Handshake will win in AI data labeling
(19:24) Growing to $250m+ Revenue
(21:56) KPIs in recruiting marketplace
(24:45) How AI will change careers
(33:57) How to build a Seal Team Six AI team
(37:06) Interning at Los Alamos
(40:00) Breaking into Silicon Valley from Michigan
(44:19) Helping friends get jobs at Palantir
(48:13) Driving across the US sleeping in McDonald’s parking lots
(54:52) Funding early days with his dad’s retirement account
(57:37) Handwriting letters to get the first six customers
(1:03:06) Early product failures and iterations
(1:11:01) Fundraising, crashing on couches for seven months
(1:17:07) Finally closing a Seed round
(1:20:05) Moving from Michigan to SF with no money
(1:23:38) Importance of sequencing new features
(1:29:10) Handshake’s exec recruiting process
(1:32:01) Building a company with your best friends
Referenced
Try Handshake
Careers at Handshake
Peter Thiel Startup School
Paul Graham’s blog
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Jake Cooper is the Founder of Railway.
This conversation explores how AI accelerates the need for strong backend infrastructure, when to build vs buy in AI software, and why there are only two moats: solving hard problems and doing hard things.
We also unpack Railway’s bold product bets, like enabling creators to earn revenue with backend templates, building their own data centers, and not building their own AI models.
Jake also talks about their four week new hire onboarding, how they build a problem roadmap, why operators should be managers, and why you should almost never work weekends.
Thank you to Angelo Saraceno @ Railway and Erica Brescia Bacon @ Redpoint for help brainstorming topics for the conversation.
Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get your $250 here.
Timestamps:
(3:33) Solving the hardest problems in dev tools
(8:16) Starting with the hardest thing
(11:18) How AI accelerated the need for Railway
(12:50) Importance of backend in AI-native software
(16:52) Jake’s angel fundraise strategy
(20:51) Resisting AI for so long
(25:32) Using AI to get leverage
(29:57) Build vs buy in AI software
(33:22) When Jake knew Railway was working
(34:27) Creating infrastructure templates
(38:04) Building data centers and a cloud service
(40:27) Two moats: Hard problems and hard things
(46:25) Hitting 8-figures in revenue
(48:47) Railway’s four week onboarding
(54:25) Building a problem roadmap
(56:16) You can’t set your own culture
(1:01:58) Railway’s viral “How We Work” post
(1:08:39) Using Discord instead of Slack
(1:11:25) How hypergrowth companies mess up org design
(1:14:03) Why you shouldn’t work weekends
(1:19:45) Not betting big on AI models
(1:21:53) Lessons from Zuck, Martin Scorsese
Referenced
Careers at Railway
How We Work Volume 1
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Today’s guest is Matt Mullenweg, Co-founder of WordPress, which powers over 43% of all websites on the internet, and founder of Automattic.
Our conversation explores the 2000’s internet, the early days of Automattic, and the decisions and philosophies that set them up for success 20 years later.
We talk open source software, why Matt’s such a big proponent of it, how Automattic built its business model as one of the first SaaS companies (that now owns companies like Tumblr and WooCommerce), and how AI is changing engineering.
Matt also shares how to build a community around your product, “Conscious Capitalism”, what he learned running one of the first distributed teams, and lessons on optimism from Walt Disney.
Thanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp.
Sign-up for Ramp and get $250 here.
Timestamps:
(3:48) WordPress: Powering 43% of the internet
(8:30) Outcompeting Reid Hoffman’s startup in the early days
(14:03) Why open source wins over the long-term
(16:21) Business models in open source
(21:12) Starting Automattic in 2005, one of the first SaaS companies
(28:45) Spending most of Automattic’s Seed round on servers
(33:36) How to use Community + Word of Mouth for early growth
(38:38) Matt’s current situation with WP Engine
(43:30) How to give back in open source
(53:55) Best practices from 20 years of running a remote company
(59:59) Lessons on optimism from Walt Disney
(1:12:33) How AI is changing coding
(1:16:09) Automattic's internal employee secondary market
(1:23:51) How open source increases longevity
(1:26:08) Matt’s favorite classical thinkers
Referenced:
Matt’s Blog
Bay Lights in SF
Matt's favorite quote from Rudy Francisco
Maintenance by Stuart Brand
We are as Gods by Stuart Brand
Marginal Revolution by Tyler Cohen
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Grant Lee is the Co-founder & CEO of Gamma, building instant PowerPoints, presentations, and websites with AI.
As someone who’s made a lot of decks, its refreshing how Gamma thinks about slides starting with the words and narrative, using AI to build the design around the story.
Gamma has put up impressive metrics, growing from zero to $50 million in ARR and 50 million users with only 30 employees. They’ve also had zero employee attrition, and a negative lifetime burn rate, with more cash in the bank than they’ve raised.
We talk about building a horizontal product instead of for a specific vertical, why Grant likes hiring generalist’s, how a quarter of the team is designers, why they’ve never raised large funding rounds, and how they run the company with an efficient team while not subscribing to 996 working hours.
Grant also shares how Gamma rebuilt their entire product to be AI-native in the months after ChatGPT launched, and how every department at Gamma uses AI internally.
Thanks to Anamitra and Gaurav at Afore, Shiyan @ Hustle Fund, Evan @ South Park Commons, and Vas @ Accel for helping brainstorm topics for Grant.
Special thanks to presenting sponsor of The Peel, Ramp.
Ramp: Time is money. Save both with Ramp. Join 40,000+ companies, go to https://ramp.com/ThePeel
Numeral: The end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel
Timestamps:
(3:46) Gamma: The anti-Powerpoint
(5:56) How to be efficient with a small team
(7:58) Importance of full-stack generalists
(12:15) How to hire problem solvers
(15:57) Changing slides from designs to narratives
(20:13) Gamma’s freemium AI business model
(22:36) Ignoring conventional wisdom with a horizontal product
(28:47) Why Gamma started with Slides
(32:21) Raising a Pre-Seed for a horizontal product
(38:25) Why Gamma avoided hyped funding rounds
(40:57) How fundraising impacts recruiting
(43:40) Liquidation preferences and employee equity
(47:08) Gamma’s zero employee attrition
(49:54) Working in-person during COVID
(52:15) Using waitlists to batch new user cohorts
(56:08) Re-building the product to be AI-native
(58:17) How to improve your onboarding
(1:00:46) Benefitting from AI models getting better
(1:05:10) Growing from 60k to 50 million users
(1:07:30) How to stand out as an AI company
(1:09:23) Creating a Gamma API
(1:11:37) How Gamma uses AI internally
(1:15:06) Why Gamma doesn’t do 996 working hours
(1:19:54) 4-month product sprints
(1:22:16) Parenting hacks: sleep, exercise, nutrition
(1:24:26) Brand and community lessons from Nike and Apple
Referenced
Careers at Gamma
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Ryan Sachtjen is the Co-founder and CEO of Threeflow, building software for employee benefits brokers and insurance carriers.
We start with a deep dive into the nearly $2 trillion dollar employee benefits market, including the structural issues that actually give the smallest companies the most leverage.
We also talk about insurance more broadly, AI opportunities in insurance, lessons from kickstarting a marketplace doing nearly $3B in volume, when his wife got cancer two months after closing Threeflow's seed round, and how his co-founders adjusted to support him.
Special thanks to Bolt for supporting this episode! Join the world’s largest hackathon - up to $1m in prizes. Sign-up here.
Timestamps:
(3:57) Threeflow: B2B benefits marketplace
(5:50) How the benefits industry works
(9:20) The importance of brokers in insurance
(12:32) Benefits broker software stack
(15:36) How to make money in employee benefits
(21:11) Ways to compete in insurance
(26:34) How AI is changing insurance
(31:01) What its like to be an insurance broker
(35:37) Starting ThreeFlow in 2016 pre-LLMs
(40:13) The 128 day walk through Europe before Threeflow
(44:47) When his wife was diagnosed with breast cancer
(50:23) Advice for founders on surviving large personal events
(52:46) Threeflow’s unorthodox Seed round
(59:46) How to vet your investors
(1:04:14) Why insurance brokers exist
(1:05:08) How to build a marketplace on top of Vertical SaaS
(1:10:53) Choosing a marketplace entry point
(1:15:05) $2.5B in premium volume on Threeflow workflows
(1:26:39) Importance of supply side volume in a marketplace
(1:31:21) Fundraising without a formal process
(1:33:03) Hiring for “just get stuff done”
(1:36:22) AI opportunities in insurance
(1:41:05) Building software in insurance
(1:44:56) Tactics for running a distributed team
(1:49:04) Creating your own playbooks
Referenced
Try Threeflow
Careers at Threeflow
Follow Ryan
LinkedIn: https://www.linkedin.com/in/ryansachtjen/
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Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
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Samir Kaji is the Co-founder and CEO of Allocate.
This conversation is a deep dive into the private markets, the evolution of venture capital as an asset class, and how there are now 10x more private investment firms than public companies.
We also unpack why 90% of venture funds simply can’t raise capital right now, advice for anyone raising a fund today, how to stand out as an emerging manager, why secondaries have become a primary driver of liquidity in venture, and how to navigate SPVs as a GP and LP.
We also talk through the AI products they built to evaluate fund managers at Allocate, and how AI is changing venture and company building.
A special thanks to Bolt and Warp for supporting this episode.
Bolt: Join the world’s largest hackathon - up to $1m in prizes. Sign-up here.
Warp: Automates payroll, handles multi-state tax compliance, and streamlines international contractor payments, so founders can focus on building, not busywork. Try it here.
Timestamps:
(5:31) Evolution of the private markets
(17:55) VC markets post-2020
(21:09) Risk / return profiles of various fund sizes
(24:04) Secondaries will drive future venture returns
(33:17) Creative ways to return capital
(36:27) “Curiosity Revenue” in AI
(41:52) Allocate’s Beyond Summit
(43:42) Samir's AI fund analyzer
(46:15) Fintech only 1% of financial services revenue
(50:13) Triple-layered SPVs
(54:50) Breaking down returns in venture
(58:27) How to gauge a fund manager’s access
(1:00:14) Determining appropriate fund size
(1:05:02) 90% of venture funds cannot raise right now
(1:09:50) How to raise a fund today
(1:15:37) ChatGPT roasts Banana Capital
(1:19:56) Traits of the best VCs
(1:22:41) Vetting grit, hustle, and obsession
(1:31:12) Why using AI is table stakes
(1:36:49) Value of podcasts
Check out Allocate
The Peel episode with Eric Vishria
Samir’s Venture Unlocked Podcast
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Anamitra Banerji is the Co-founder of Afore Capital, an SF-based VC firm that specializes in investing in pre-seed stage companies.
Our conversation gets into the evolution of Pre-Seed as a category, why Pre-Seed is more than option checks, what Afore looks for when backing founders before they even have a product, how to skip your Seed and go straight to a Series A, and how to run a fundraise process.
We also get into Afore’s Founder in Residence program, why every VC started an accelerator, how AI is changing venture, joining Twitter as the first PM, and how Oprah helped create the legendary verified checkmark.
Thanks to Gaurav Jain and Derrick Li at Afore for their help brainstorming topics for Anamitra.
And special thanks to Bolt and Warp for supporting this episode.
Bolt: Help them break a world record for the largest hackathon - up to $1m in prizes. Sign-up.
Warp: Automates payroll, handles multi-state tax compliance, and streamlines international contractor payments, so founders can focus on building, not busywork. Try it here.
Timestamps:
(4:00) Afore: Starting in 2016 to build the pre-seed category
(8:11) The unstructured data Afore underwrites at pre-seed
(11:21) Pre-seed is determining bronze from gold
(16:03) Why pre-seed is more than option checks
(20:33) The secret to raising a Series A
(23:20) Running a tight fundraise process
(32:05) Skipping your Seed round
(34:01) How to measure obsession in a founder
(39:20) Knowing when to follow-on
(40:54) Figuring out what really matters in a business
(42:36) Afore’s Founder in Residence program
(49:44) Pros / Cons of more access to capital for founders
(52:27) Two reasons YC made every VC launch an accelerator
(1:01:05) Why AI is forcing VCs to invest earlier
(1:06:55) Will AI commoditize software?
(1:08:29) Growing up in India, starting his first company
(1:10:39) Coming to the US for school, joining Overture + Yahoo
(1:14:05) Joining Twitter as first PM, creating the Verified check for Oprah
(1:18:55) Building Twitter’s first ad product
(1:20:28) Why non-founders can’t take foundational risks
(1:23:02) Starting Afore for the Pre-Seed opportunity
(1:27:47) Raising Afore Fund 1
(1:31:14) How to raise your first fund
(1:33:33) Was Turner the best Afore intern ever?
Referenced
Afore’s Founder in Residence Program:
Follow Anamitra
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Eric Vishria is a General Partner at Benchmark Capital.
Our conversation goes inside the new class of startups going zero to $100 million ARR in 12 months, the ways AI is changing company building, and how Eric and Benchmark make new investments.
We get into the risk rewards of Series As today, how Benchmark competes to work with founders, and and why the best storytellers win.
We also talk about parallels between the 90’s, 2000’s, and today, and how the archetype of successful founders has changed in the age of AI.
Thanks to Spenser Skates, Sajith Wickramasekara, Bobby DeSimone, and Semil Shah for help brainstorming topics for Eric!
Special thanks to this episode’s sponsors:
Timestamps:
(5:17) What gets Eric excited about a new investment
(7:48) Backing learning machines
(12:34) Backing Cerebras at inception
(16:20) Why the best storytellers win
(21:17) How Eric works with founders
(26:38) Companies going zero to $100m in 12 months
(31:09) Revenue quality of AI products
(32:41) Moats and business models in AI
(38:41) AI margins and runway
(41:14) Parallels between winners of the 90’s and today
(44:54) Archetypes of the best AI founders
(50:43) SaaS companies successfully pivoting to AI
(53:43) LLMs are most comparable to transistors in the 1950s
(56:19) Ways Eric uses AI personally
(58:05) How VC has changed over the past decade
(1:01:40) VC is a hustler’s business
(1:03:20) Backing extraordinary companies is all that matters
(1:09:36) What makes Benchmark unique
(1:17:03) How Benchmark makes investment decisions
(1:18:38) Skipping senior year of high school
(1:20:21) Working with Ben Horowitz and Marc Andreessen ‘00-’08
(1:24:42) Starting RockMelt, selling to Yahoo
(1:26:28) Joining Benchmark in 2014
(1:28:08) Investing in Confluent one month later
(1:28:50) Lessons from Spenser at Amplitude
(1:29:36) Fireworks AI’s hyper growth
(1:30:49) Pricing in AI changing from tokens to outcomes
(1:32:23) Ways Eric’s perception of VCs changed after becoming one
(1:34:07) How to build a management team
(1:38:21 )The best CEOs make new mistakes
(1:39:50) Why there should be more public companies
(1:44:03) “Even great companies can be overvalued”
Referenced
Ben Thompson + Mark Zuckerberg Interview
Andy Price at Artisinal Talent
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Sanjit Biswas is the Co-founder and CEO of Samsara, the fleet management and safety platform.
At the time of publication, Samsara is a public company worth over $26 billion, and we unpack how exactly they went from zero to run rating at over $1.5 billion in revenue in ten years.
We get into using AI to impact the physical world, how Samsara uses AI internally, and how their products prevent over 200,000 deaths per year.
Sanjit has built two unicorns, and he shares everything he’s learned along the way, including what most founders and investors get wrong about hardware, thinking customer-first instead of product-first, how to know when you have product market fit, mastering sales as a technical founder, and how to spend more time with your customers.
We also talk about getting his high school online in the 90’s, and the research project that turned into Sanjit’s first company, Meraki, and its $1.2 billion dollar sale to Cisco in 2012.
Thanks to Bolt for supporting this episode. Help them break a world record for the largest hackathon (up to $1m in prizes): https://bit.ly/ThePeelBoltHackathon
Timestamps:
(4:26) Samsara: Helping the world of physical operations
(8:44) Preventing 200,000 deaths per year
(11:19) AI opportunities in transportation
(14:43) Samsara’s internal AI tools
(16:58) What people get wrong when building hardware
(19:04) Starting Samsara customer-first instead of product-first
(22:23) Find adjacent products for your customers
(26:28) How to know you have product market fit
(34:52) How to spend more time with customers and build feedback loops
(43:00) 70-20-10 framework for allocating capital
(45:07) Importance of selling new products to existing customers
(49:15) Revisiting the product roadmap based on new technology
(50:38) Why Sanjit credits focus to hitting $1B revenue in nine years
(53:41) Learning to love sales as a technical founder
(57:06) Getting his high school online in the 90’s
(1:01:46) The research project that turned into Sanjit’s first company, Meraki
(1:04:01) Importance of asymmetric risk when starting a company
(1:05:41) Early days of Meraki taking off
(1:09:19) Surviving and doubling during the financial crisis
(1:16:00) Cisco acquiring Meraki for $1.2B
(1:18:15) Meraki’s post-acquisition integration
(1:20:48) Differences between 1st and 2nd company
(1:24:19) Almost starting an renewable energy company
(1:25:52) The power of small teams
(1:28:49) One-shotting Bill Gates’ biography at 10-years old
Referenced
Samsara: https://samsara.com/
Meraki: https://meraki.cisco.com/
Arduino: https://www.arduino.cc/
Raspberry Pi: https://www.raspberrypi.com/
Hard Drive: Bill Gates and the Making of the Microsoft Empire: https://www.amazon.com/Hard-Drive-Making-Microsoft-Empire/dp/0887306292
No Priors Podcast: https://www.youtube.com/@NoPriorsPodcast
Follow Sanjit
LinkedIn: https://www.linkedin.com/in/sanjitbiswas/
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LinkedIn: https://www.linkedin.com/in/turnernovak
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Michael Kim is the Founder of Cendana Capital, a fund of funds that makes anchor investments in very early stage VC funds.
We talk characteristics of the best investors, how Cendana does diligence on fund managers, portfolio construction best practices, Michael’s “60x rule”, and why high ownership to fund size is the main driver of returns.
We also get in to how VCs are using AI, the competition between Seed and multi-stage investors, why US endowments are under siege, and how secondaries are driving most early stage venture returns today.
Michael also opens up about the early days of starting Cendana, the 18 month grind raising Cendana Fund 1, the day he almost died, and ranking in the top 2% globally in Call of Duty.
Special thanks to Roger Ehrenberg, Kevin Hartz, Semil Shah, Jeff Claviar, Beezer Clarkson, Jack Altman, Jeff Morris Jr, Sheel Mohnot, Nichole Wischoff, Ted Alling, and Rick Zullo for their help putting this episode together.
Thanks to Bolt for supporting this episode. Help them break a world record for the largest hackathon (up to $1m in prizes): https://bit.ly/ThePeelBoltHackathon
Timestamps:
(4:24) The day Michael almost died
(5:10) Call of Duty & video games
(9:34) Hiring @ Cendana
(10:31) How Cendana uses structured and unstructured data
(16:51) How VCs are using AI
(19:55) Why secondaries are driving most early stage venture returns
(22:01) Deciding when to sell secondaries
(24:28) Best performing venture funds ever
(27:26) The best VCs have amazing access to the best founders
(33:42) Why Cendana backs Solo GPs
(35:57) How to invest over time and hype cycles
(41:35) Why multi-stage firms are investing earlier
(44:45) Cendana’s current thesis: High ownership % to fund size
(45:51) Why Cendana started backing non-lead VCs
(48:41) How Cendana does diligence on fund managers
(52:22) VC NPS Scores and Ron Conway’s Silver Bullet
(53:49) Good vs bad new VC firm strategies
(56:36) Determining defensibility of a strategy
(57:57) “Messy middle” software buyout fund
(1:03:25) Portfolio construction best practice
(1:08:11) Michael’s 60x Rule
(1:14:28) How Seed funds compete with multi-stage funds
(1:20:05) Should you collect logos writing small checks?
(1:21:07) Becoming an LP for the city of SF
(1:24:42) Taking 18+ months to raise Cendana Fund 1 in the GFC
(1:26:48) Warehousing the first Cendana Fund 1 investments
(1:29:56) How to do a first close
(1:34:29) Why it’s hard to kill a VC firm
(1:37:00) What happens to ZIRP tourist fund managers
(1:40:22) How to raise a Fund 2 or 3 today
(1:42:07) “US endowments are under siege”
(1:44:55) What the best GP LP relationships look like
(1:46:41) What Fund of Funds get wrong
(1:50:43) The three most interesting trends in venture today
Referenced
Check out Cendana https://www.cendanacapital.com/
Deep Checks https://www.deepchecks.vc/
Prior episode with Eric at Bolt https://www.youtube.com/watch?v=7Q6n1vqUrF4
Follow Michael
Twitter: https://x.com/MKRocks
LinkedIn: https://www.linkedin.com/in/michael-kim-cendana-capital/
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LinkedIn: https://www.linkedin.com/in/turnernovak
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