The Peel with Turner Novak

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/