The Peel with Turner Novak

Jamie Siminoff built the first WiFi video doorbell in his garage, got rejected on Shark Tank, and nearly went bankrupt "at least four times" while growing Ring into one of the largest consumer hardware businesses in the world.

We talk about the $1.15B sale to Amazon, coming back to lead Ring after leaving post-exit, and what he learned having a fresh set of eyes on the business.

We also get into the near death stories, like Christmas the company almost died from $1M of bricked doorbells, the $175k "F you, wire it" fight for the Ring.com domain, betting millions on TV ads when the board said no, landing Shaq as an early investor and celebrity endorser, the real backstage story of three dead demo units on Shark Tank, and why Jamie thinks AI can zero out crime in neighborhoods.

Thanks to this episode's sponsors:

Monaco: The revenue engine for startups https://monaco.com

Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital

Numeral: Sales tax on autopilot https://numeral.com

Amplitude: AI analytics https://amplitude.com

Timestamps:

(0:00) Leaving Amazon, coming back with fresh eyes

(7:49) Deleting every useless meeting

(10:21) Zero-based time budgeting

(15:31) Bubble, or the golden age of AI?

(19:50) $480M to several billion in revenue

(23:48) Lessons on obsession from MrBeast

(30:17) The AI vision for Ring

(34:05) The $10k feature he can't ship yet

(38:50) Building apps on top of Ring

(40:03) Building in his garage, the Kickstarter ban

(44:45) The pre-sale, and the fear of getting copied

(47:59) How he talked his way onto Shark Tank

(49:24) Three dead units backstage

(54:04) Threatening Shopify's CEO before air

(55:23) The Christmas Ring almost died

(58:59) The midnight fix that saved the company

(1:01:22) Raising from True Ventures, the "ass hat" email

(1:05:04) Hiring gritty “new to business” people

(1:07:15) Missionaries, not mercenaries

(1:10:13) Building an authentic brand people trust

(1:12:49) Buying Ring.com with the last $175k of cash

(1:18:11) “We were always on the verge of bankruptcy”

(1:19:12) Betting $1M on TV ads when the board said no

(1:22:43) Why TV ads actually work

(1:25:26) Richard Branson, and doubling mid-raise

(1:28:46) Closing Shaq, how to do authentic celebrity endorsements

(1:33:27) Selling to Amazon for $1.15 billion

(1:35:16) Being paranoid to lose people's money

(1:36:38) Mentors, and never meeting your heroes

Referenced:

Ring: https://ring.com

Dyson: https://www.dyson.com

True Ventures: https://www.trueventures.com

Om Malik: https://om.co

Adam D'Augelli: https://www.linkedin.com/in/adamdaugelli/

Saar Gur: https://www.linkedin.com/in/saargur/

Eoghan McCabe: https://www.linkedin.com/in/eoghanmccabe/

Sky Dayton: https://www.skydayton.com/

Tobi Lütke: https://www.linkedin.com/in/tobiaslutke/

Follow Jamie

Twitter: https://x.com/JamieSiminoff

LinkedIn: https://www.linkedin.com/in/jamiesiminoff/

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/

Tomer London is the Co-founder and Chief Product Officer of Gusto.

We go deep on how Gusto builds product, from obsessing over customers to shipping Gusto Cofounder with AI in eight weeks. We also get into what AI is doing to small businesses, surviving COVID, the manual world of payroll before software, what his dad's 40-year clothing store taught him, starting Gusto out of YC, and how Gusto thinks about making acquisitions now that it’s crossed $1B ARR.

Thanks to this episode's sponsors:

Numeral: Sales tax on autopilot https://numeral.com

Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital

Amplitude: AI analytics https://amplitude.com

Monaco: The revenue engine for startups https://monaco.com

Timestamps:

(0:00) Obsessing over small businesses

(10:09) Building Gusto Cofounder in 8 weeks

(13:57) What AI is actually doing to small businesses

(19:52) COVID and "the end of small business"

(27:42) Why running a small business is so hard

(32:21) SVB and why payroll can't be late

(36:29) How GTM changes after 500,000 customers

(39:27) Running payroll manually before Gusto

(46:19) Why payroll and compliance are so hard

(49:14) What his dad's clothing store taught him

(54:00) Are we regulating small business out of existence?

(58:04) Starting as ZenPayroll in 2012

(1:05:02) Getting the first customers

(1:07:28) Minimum Lovable Product vs MVP

(1:11:28) How AI changed the way Gusto builds

(1:15:58) Gusto's M&A playbook

(1:22:52) Shimon Peres and "no room for small dreams"

Referenced

Gusto: https://gusto.com

Guideline: https://www.guideline.com

Y Combinator: https://www.ycombinator.com

Sam Blond on The Peel: https://www.thespl.it/p/the-ai-native-gtm-playbook-sam-blond

No Room for Small Dreams, by Shimon Peres: https://www.amazon.com/No-Room-Small-Dreams-Imagination/dp/1538412209

Follow Tomer

Twitter: https://x.com/tomerlondon

LinkedIn: https://www.linkedin.com/in/tomerlondon

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/

Jeff Morris Jr is the founder and Managing Partner of Chapter One. Previously, he was employee 50 at Tinder and started Chapter One from his desk before quitting to go full-time on investing.

We talk about running a venture firm more like a product team, running 50 experiments every fund cycle, why Sequoia doing $60 million Seeds has killed round labels, why the best firms only pick right 4-7% percent of the time, running the world's smallest accelerator, branding a venture firm, when to pivot, the time he delivered Valentine's flowers himself in Kansas, why none of his Fund 1 winners were in the Bay Area, and why he never announced his $64m Fund 3.

Thank you to Numeral, Flex, Amplitude, and Monaco for supporting this episode.

Numeral: Sales tax on autopilot https://numeral.com

Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital

Amplitude: AI analytics https://amplitude.com

Monaco: The revenue engine for startups https://monaco.com

Timestamps:

(0:00) Publishing IC notes every week

(3:48) Do round names matter anymore?

(8:20) Putting a big check into Erebor's $2B round

(11:40) Why deep tech went from instant pass to preferred in 3 years

(15:32) When deep tech companies should raise debt

(19:03) Should this company raise $1M or $100M?

(23:25) You have two days to say yes

(25:58) Sourcing software he built at Tinder

(28:05) Their crypto book hit 22x, then the market turned

(30:58) Paradigm, SendCutSend, and re-founding a firm

(33:35) If you're going to pivot, re-found the company

(37:21) Flex's wedge was too illegible to fund

(40:13) When should you actually pivot?

(42:47) Zaarly, the Uber for everything

(45:17) Moving to Kansas City with a bag of clothes

(47:25) Delivering flowers door-to-door

(51:31) Raising a $64M Fund 3 and not announcing it

(56:33) Joining Tinder as employee 50

(57:35) The push notification that took down Tinder

(1:00:59) Why you shouldn’t start a dating app

(1:04:18) Consumer got too predictable

(1:09:00) Why consumer AI economics look worse than enterprise

(1:13:02) Launching Chapter One from his Tinder desk

(1:15:08) 50 experiments per fund cycle

(1:16:11) Product Club, the world's smallest accelerator

(1:19:05) Evolving portfolio construction between funds

(1:21:25) Why picking rates have fallen

(1:24:41) Smaller funds can invest in illegible categories

(1:27:27) Zero Fund 1 returners were in the Bay Area

(1:29:16) Don't compete with Sequoia at Seed

(1:32:01) His grandfather built Mervyn's

Referenced

Chapter One: https://chapterone.com

Erebor: https://erebor.bank

Flex: https://flex.one

SendCutSend: https://sendcutsend.com

Paradigm: https://www.paradigm.xyz

Supabase: https://supabase.com

Poke: https://poke.com

Floodgate: https://www.floodgate.com

SV Angel: https://svangel.com

Union Square Ventures: https://www.usv.com

Zaarly: https://www.crunchbase.com/organization/zaarly

Mervyn's: https://en.wikipedia.org/wiki/Mervyn's

Mervin Morris obituary: https://www.almanacnews.com/news/2021/09/10/mervin-morris-founder-of-mervyns-stores-atherton-resident-dies-at-101/

People Mentioned

Jamesin Seidel: https://www.linkedin.com/in/jamesin-seidel-5325b147/

Palmer Luckey: https://x.com/PalmerLuckey

Mike Maples Jr: https://www.linkedin.com/in/maples/

Scott Belsky: https://www.linkedin.com/in/scottbelsky/

Josh Elman: https://www.linkedin.com/in/joshe/

David Lee: https://www.linkedin.com/in/davidlee10/

Max Mullen: https://www.linkedin.com/in/maxmullen/

Follow Jeff

Twitter: https://x.com/jmj

LinkedIn: https://www.linkedin.com/in/jeffmorrisjr

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/

Ron Gabrisko might have the best sales seat in software. He joined Databricks as CRO at less than $1M in revenue, and built it into a $7B+ ARR business over the next decade.

Almost no one has built a revenue engine this big this fast, so he's the right person to walk through how you actually do it, from the first 40 reps to selling AI into the enterprise today.

We talk through Databricks' early decisions, like killing seat-based pricing as usage took off, using a16z to land the first big logos, the four C's every enterprise now weighs on AI, how Ben Horowitz recruited him to seven PhDs who were giving away their software for free, why he only hires sellers who can demo the product themselves, and how he runs his entire sales org on his own product, Databricks' Genie.

Thank you to this episode’s sponsors!

Numeral: Sales tax on autopilot https://www.numeral.com

Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital

Amplitude: AI analytics https://www.amplitude.com

Merge: Every model, one API https://www.merge.dev/turner

Monaco: The revenue engine for startups https://www.monaco.com/

Timestamps:

(0:00) From under $1M to $7B+ in revenue

(1:07) Seven founders and three big bets

(2:49) Why going cloud-only was contrarian

(5:14) Monetizing open source: "what will they pay for?"

(11:40) What Databricks actually is

(14:17) Genie, the AI he runs the business on

(19:20) It's the data context, not the model

(21:36) The early AI bet, before LLM's

(26:32) Why enterprise AI beats consumer AI

(30:00) Automating his own sales org

(32:18) How Ben Horowitz pitched him

(33:48) Why seven co-founders is an advantage

(35:54) Teaching the CEO sales: org charts and MEDDIC

(42:08) Biggest sales mistakes and four growth stages

(45:14) Why technical products need technical sellers

(47:21) The seller profile: technical, gritty, no short stints

(50:45) Back-channeling references that don't BS you

(53:32) Hiring 40 reps and why PLG didn't convert

(58:07) How a16z opened enterprise doors

(1:05:47) Why he gives POC's away for free

(1:08:50) Raising prices to match value

(1:11:34) Why he killed seat-based pricing

(1:14:37) Build for enterprise requirements early

(1:16:46) Consumption selling and the six-month planning cycle

(1:19:54) Expanding internationally without breaking it

(1:23:38) The four C's of enterprise AI

(1:26:54) Why messy data blocks AI adoption

(1:29:07) Forward deployed engineers: what makes them win

(1:31:56) When does Databricks go public?

(1:33:36) LL Cool J, Michael Jordan, and never losing a game

Referenced

Databricks: https://www.databricks.com

Careers at Databricks: https://www.databricks.com/company/careers

Apache Spark: https://spark.apache.org

MosaicML: https://www.mosaicml.com

Relentless Book: https://www.amazon.com/dp/1797121782?lv=shuf&channelId=500&plpRedirect=mhFallback

Follow Ron

LinkedIn: https://www.linkedin.com/in/ron-gabrisko-4a21a

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/

Ryan Nece runs Next Legacy, a $4 billion fund of funds that connects athletes and philanthropists with the top venture capital firms in the world.

Ryan is the only player in NFL history to win a Super Bowl as a rookie and go 0-16 in his final season. His dad, Hall of Famer Ronnie Lott, started one of the first athlete-backed venture funds with Joe Montana in the late '90s.

Ryan rebuilt that playbook a generation later, so almost nobody is better positioned to explain the similarities between pro athletes and the top founders / investors, how athletes actually break into Silicon Valley, the biggest mistakes they usually make, .

Thanks to this episodes sponsors!

Numeral: Sales tax on autopilot https://www.numeral.com

Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital

Amplitude: AI analytics https://www.amplitude.com

Merge: Every model, one API https://www.merge.dev/turner

Monaco: The revenue engine for startups https://www.monaco.com/

Timestamps:

(0:00) How a football family broke into Silicon Valley

(4:33) A Super Bowl rookie year with four Hall of Famers

(8:09) What separates the top 0.1% of athletes?

(12:18) The mistake of having "a guy"

(18:41) Vetting who to trust

(20:18) The dumbest investments athletes make

(22:45) How athletes can help founders

(29:44) VC Power Law is just like sports

(34:24) How to break in without connections

(38:05) Building Next Legacy to $4B AUM

(40:44) Why they give away all the profits

(43:20) Early firm building mistakes

(48:19) Learning to pitch institutional LP's

(53:03) The emerging-manager barbell

(55:45) “Your starting five tells me who you are”

(57:47) The other AI: Authentic Interaction

(59:55) Getting LP attention with the rule of three

(1:03:40) Working the whisper network

(1:06:03) Pick the kid who gets picked last

(1:12:26) The Lions 0-16 season

(1:14:43) The “Next Play” mindset

(1:19:28) Mental toughness

(1:21:32) What it’s like commentating an NFL game

(1:27:14) Getting cussed out by Warren Sapp

(1:31:13) His favorite athlete: Jerry Rice

(1:35:15) Abe Lincoln and his grandfather's restaurants

Referenced

Next Legacy: https://www.nextlegacy.com/

Give and Take: https://www.amazon.com/Give-Take-Helping-Others-Success/dp/0143124986

Three Feet From from Gold: https://www.amazon.com/Three-Feet-Gold-Obstacles-Opportunities/dp/1402784791

Team of Rivals: https://www.amazon.com/Team-Rivals-Political-Abraham-Lincoln/dp/0743270754

Follow Ryan

Twitter: https://x.com/ryannece

LinkedIn: https://www.linkedin.com/in/ryan-nece-abb07b8

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 is the Co-Founder and CEO of Drive Capital. Prior to Drive, Chris was a Partner at Sequoia Capital where he helped launch the firm’s first growth fund.

Chris left Sequoia in 2012 to start Drive in Ohio on a single bet: the best companies in America are getting built outside Silicon Valley (and almost nobody's funding them). Thirteen years later, Drive has handed back over $1 billion to its investors in a market where most funds can't return a dollar.

We talk chasing $2B outcomes instead of $50B, when his lead investor pulled out the day he moved from SF to Columbus, why only 100 of 3,500 firms can raise right now, the welders quitting to drive DoorDash, and why America is the best emerging market on earth.

Thanks to this episodes sponsors!

Numeral: Sales tax on autopilot https://www.numeral.com

Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital

Amplitude: AI analytics https://www.amplitude.com

Merge: Every model, one API https://www.merge.dev/turner

Monaco: The revenue engine for startups https://www.monaco.com/

Timestamps:

(0:00) America is the best emerging market

(8:13) Why this couldn't have happened pre-2006

(10:48) Top lessons from 10 years at Sequoia

(14:17) Why the "meeting factory" model fails

(21:42) Searching for vacuums

(24:51) Sequoia passed on a company 10 miles too far

(29:37) Greece's GDP equals Detroit's

(34:34) The biggest tech companies aren't in SF

(40:28) 223 meetings to raise Fund 1

(44:27) Turning one fund into a product catalog

(48:47) The day his biggest LP pulled out

(52:08) Fundraising is a persistence game

(57:36) Returning $500M in a single week

(59:56) Only 12 companies hit $50B in 20 years

(1:01:29) Why Drive owns 30%, not 10%

(1:05:03) Returns over logos, the carry math

(1:10:00) Mindset of VC's outside SF

(1:15:54) How AI unlocks boring, giant markets

(1:19:22) Investing in catalysts, not sectors or geo

(1:25:35) 3,500 firms raised, 100 survived

(1:31:33) OpenAI won't eat every other company

(1:37:46) Compete with yesterday's version of yourself

(1:40:19) Small changes, compounding results

Referenced

Drive Capital: http://drivecapital.com/

Follow Chris

Twitter: https://x.com/ChrisOlsenCMH

LinkedIn: https://www.linkedin.com/in/cholsen

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/

Michael Tannenbaum is the CEO of Figure, the blockchain lending company he took public in 2025.

He was employee #1 at Brex, and before that ran the mortgage business at SoFi. Mike Cagney, who founded both SoFi and Figure, pulled him back to take Figure public in 2025.

This is a conversation on how to think and act like a founder, the framework he uses to run Figure, plus a look at how a lending business works under the hood, why he ran the broken mortgage business at SoFi to prove himself, the time Masa offered him a billion dollars, how he nearly walking away from Brex right before they launched, inside the SVB collapse, how Figure originates loans for $1,000 instead of $12,000, their recent Kiavi acquisition, and the gas station test his dad taught him.

Thank you to Mike Cagney, Art Levy, and Sam Blond for helping brainstorm topics for the conversation!

Thanks to this episodes sponsors!

Numeral: Sales tax on autopilot https://www.numeral.com

Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital

Amplitude: AI analytics https://www.amplitude.com

Merge: Every model, one API https://www.merge.dev/turner

Monaco: The revenue engine for startups https://www.monaco.com/

Timestamps:

(0:00) From Brex employee #1 to public-company CEO

(1:28) Operating vs managing a career

(3:23) Why he took the worst business at SoFi

(9:33) The Big Rock framework

(11:02) How to get real customer feedback

(14:58) The best nose for value in fintech

(17:49) Why banking the affluent beats down-market

(21:12) Figure: cutting mortgage cost from $12k to $1k

(25:41) Do you actually need to use blockchain?

(28:03) Why memecoins took over crypto

(32:17) Masa's billion-dollar offer

(36:29) Leaving SoFi for two kids in a kitchen

(39:05) Six months from almost quitting to a unicorn

(44:09) The finance guy who ran Brex's marketing

(47:03) Inside Brex during the SVB collapse

(51:09) The two SoFi insights behind Figure

(54:40) From direct-to-consumer to B2B marketplace

(56:41) AI can’t get you better credit ratings

(58:50) Figure is a modern Fannie Mae

(1:01:28) Buyers who commit before the loan exists

(1:03:59) Following customers into new products

(1:06:35) Buying Kiavi, the fix-and-flip leader

(1:12:15) Why more fintech’s don't become marketplaces

(1:14:46) The AI risk in outsourcing customer acquisition

(1:18:23) What going public actually takes

(1:20:14) Life as a public-company CEO

(1:22:38) Getting shorted

(1:24:12) The gas station test

(1:25:42) The reverse pyramid of big corporates

Referenced

Figure: https://www.figure.com/

Careers at Figure: https://www.figure.com/careers/

Kiavi: https://www.kiavi.com/

Follow Michael

Twitter: https://x.com/MBTannenbaum

LinkedIn: https://www.linkedin.com/in/michaeltannenbaum/

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/

Shensi Ding is the co-founder and CEO of Merge, the connective infrastructure that plugs into every tool.

Merge started in 2020 building integrations, watched its first customers die off, then rebuilt itself twice for the AI era. Not many founders talk this honestly about tearing up their company. A lot of lessons for others trying to do the same.

We get into why integrations turned out to be so important in AI, the night-shift 5-11pm build of their AI transformation, almost hiring a foreign spy, why Shensi thinks founders with an EA are moving too slow, the Embarrassment Framework, why 60% of public MCP servers quietly fail, vibe coding a dinner bot that 10x'd their customer events, and why 6% of Merge employees get married.

Thanks to this episodes sponsors!

Numeral: Sales tax on autopilot https://www.numeral.com

Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital

Amplitude: AI analytics https://www.amplitude.com

Merge: Every model, one API https://www.merge.dev/turner

Monaco: The revenue engine for startups https://www.monaco.com/

Timestamps:

(0:00) Something broke every year since 2020

(2:22) How Merge went all-in on AI on nights and weekends

(5:40) New launches got faster

(8:32) Building connective infrastructure for AI

(10:51) The dinner where Merge started

(13:11) Six months of research before a line of code

(19:00) Almost hiring a foreign spy

(20:48) Merge’s 6% marriage rate

(22:50) Hiring enthusiastic, nice, smart people

(28:02) Early stage founders don’t need an EA

(31:27) Shortcuts are a mentality

(33:01) The AI tool that 10x'd their customer dinners

(38:33) Marketing became an engineering function

(40:51) Starting with SMB and climbing the logo ladder

(42:07) How the product went cross-category

(44:16) Launching Agent Handler and a new pricing model

(46:47) Every product should be multi-model

(49:58) Why most MCP servers don’t work

(53:31) Startups should go all-in on enterprise

(57:00) The hardest things are most defensible

(1:00:26) Say "psycho shit" to be memorable

(1:05:47) The Embarrassment Framework

(1:10:23) Frank Slootman and being okay with being disliked

(1:12:48) Giving feedback got scarier at 100 people

(1:14:01) What only the CEO can do

(1:19:44) The best marketing is not doing what everyone else does

Referenced

Try Merge: https://merge.dev/turner

Careers at Merge: https://www.merge.dev/careers

Follow Shesi

Twitter: https://x.com/shensi

LinkedIn: https://www.linkedin.com/in/shensiding

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/

Navin Chaddha is the Managing Partner at Mayfield. He’s made the Forbes Midas List 18 times, and thinks a lot of the AI revenue everyone's chasing right now is fake.

Mayfield is a 56-year-old firm that backs founders at the paper-and-pencil stage. They’re investing $3 billion into AI, but Navin warns the market is overcapitalized by a factor of 10x.

We get into what’s actually going on with the $1B+ funding rounds, the $25 trillion of value AI has to justify, the dangers of FOMO, how he separates vibe revenue from real revenue, backing vertical models instead of horizontal ones, why inference will dwarf training, how a startup actually beats a $100 billion incumbent, the people x-ray behind his founder bets, what cricket taught him about running a company, lessons being the last founder to IPO before the Dot Com Crash, what he learned working with Satya Nadella, and the unfinished business still driving him.

Thanks to this episodes sponsors!

Numeral: Sales tax on autopilot https://www.numeral.com

Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital

Amplitude: AI analytics https://www.amplitude.com

Merge: Every model, one API https://www.merge.dev/turner

Monaco: The revenue engine for startups https://www.monaco.com/

Timestamps:

0:00 Lumilens: Zero to $3B revenue in 14 months

0:50 Connecting GPU's is AI's next bottleneck

5:07 Mayfield: investing $3B in AI and semiconductors

9:39 Where a $1B round actually gets spent

12:51 The six-layer AI stack, and who needs mega-rounds

15:00 Why AI is overcapitalized by 10x

17:47 FOMO is for sheep

21:13 Vibe revenue vs real revenue

22:45 Backing vertical models

24:22 The best firms have one North Star

27:18 Are semiconductors still cyclical?

29:10 Why inference will dwarf training

31:19 What happens after every infra build-out

36:27 2 billion Gemini users isn't real AI adoption

38:21 What a correction does to AI stocks

40:46 How FOMO pulls VC's into hot categories

44:13 What Navin looks for in founders

50:23 Why "everyone hates this category" can be a buy signal

54:12 The argument against the cloud everyone got wrong

57:20 What white-collar work AI teammates will take

1:01:45 How AI startups beat incumbents

1:06:54 Why startups die of indigestion

1:11:49 Mayfield’s secret formula: people-first

1:19:18 What cricket taught Navin about building companies

1:23:17 Dropping out of Stanford to start VXtreme

1:29:22 Blitzscaling to blitz-failing: the last IPO before the Dot-Com Crash

1:31:25 Joining Mayfield instead of starting a 4th company

1:33:29 Unfinished business (backing a $1T company)

1:35:54 Could you tell Satya would run Microsoft?

1:38:58 Investors he respects, founders he missed

Referenced

Mayfield: https://www.mayfield.com/

Lumilens: https://lumilens.com/

Lumilens Raises $700M: https://www.wsj.com/tech/startup-raises-700-million-to-replace-data-center-wires-with-light-adc74358?mod=e2twd

Built to Last by Jim Collins: https://www.amazon.com/s?k=built+to+last+-+jim+collins&adgrpid=186020621003&hvadid=779535177756&hvdev=c&hvexpln=0&hvlocphy=9218885&hvnetw=g&hvocijid=9037174021105194159--&hvqmt=e&hvrand=9037174021105194159&hvtargid=kwd-362242264527&hydadcr=21907_13365950_10662&mcid=f1dd2c5deb5539b7afc6bcdfee5613c8&tag=googhydr-20&ref=pd_sl_4b3f3t1l23_e

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Alamin Uddin is the co-founder and CEO of NexHealth.

Today, NexHealth’s healthcare infrastructure serves 89 million patients. But at one point, the company had $4,000 in the bank and a maxed-out Amex card.

We talk about why 75% of dentists still keep a server in the closet, how healthcare skipped the internet, cloud, and mobile and went straight to AI, why most healthcare systems have no API, funding the company with side hustles, the $36k customer pre-pay that saved the business, how 81% of new AI healthcare startups are built on NexHealth, where he thinks AI value actually accrues, and outlasting OpenAI.

Thanks to this episodes sponsors!

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Timestamps:

(0:00) Healthcare skipped 3 platform shifts and went straight to AI

(4:10) 75% of dentists still have on-prem servers

(10:05) How data interoperability holds back healthcare innovation

(16:02) Why everyone blames Epic

(20:15) Building the developer platform for healthcare

(24:36) Why everyone fails to fix the problem

(29:11) Fragmented markets enabled developer platforms

(32:32) Working as a receptionist at a doctor’s office

(36:13) Building a prototype on Twilio

(39:15) How incumbents went from blocking to partnering

(46:05) Canvassing Soho dentists door-to-door

(53:47) Reverse-engineering 40-year old databases

(56:21) Funding NexHealth with side hustles for two years

(57:30) The scheduling wedge no one could match

(1:02:20) Raising $391k from professors and customers

(1:03:46) Running out of cash, why customers kept churning

(1:07:45) $4,000 in the bank and a maxed-out Amex

(1:11:12) The $36k pre-pay that saved the company

(1:13:24) NexHealth’s three businesses today

(1:20:18) Payments and the “admin-day” problem

(1:26:15) 72% sales win rate

(1:28:27) The term sheet signed the week before COVID

(1:30:26) Spending half the Series A on an acquisition

(1:33:47) Raising $176M they didn't need

(1:37:28) Why starting before 2022 is an advantage

(1:42:22) Where AI value accrues: chips, models, the action layer

(1:44:55) 81% of AI products are built on NexHealth

(1:48:24) Staying patient for three years after ChatGPT

(1:51:25) Competitors building on their API

(1:54:02) “We’re a tech company, not healthcare company”

(1:56:09) Hiring from outside healthcare

(1:58:34) Shoes, email over Slack

(2:01:21) What AI changed inside the company

(2:04:16) Inspiration from Microsoft in 1977 - 1990

Referenced

NexHealth: https://www.nexhealth.com/

Build on NexHealth: https://docs.nexhealth.com/

Careers at NexHealth: https://www.nexhealth.com/careers

The Secret 3-Step Master Plan to Cure Healthcare: https://www.notboring.co/p/the-secret-3-step-master-plan-to

Follow Alamin

Twitter: https://x.com/alfromnexhealth

LinkedIn: https://www.linkedin.com/in/alamin-uddin-95284889

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