The Peel with Turner Novak

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.

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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

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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!

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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

Follow Navin
LinkedIn: https://www.linkedin.com/in/navinchaddha

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/

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!

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) 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

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/