The Peel with Turner Novak

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/