The Luba Show

Today I walk with Shishir Mehrotra, CEO of Superhuman, the company formerly known as Grammarly. Shishir co-founded Coda and sold it to Grammarly, built skippable ads at YouTube into a product that went from $0 to $1 billion in 18 months, and sits on the boards of Spotify and Walmart, and now he runs a company with over $700 million in revenue. He talks about why most people should not start a company, and why he gave up ownership of Coda without any startup pride.

We get into:

- Why the right startup idea should feel like a curse, and why he tells students not to keep a list of startup ideas

- The misspelled Vinod Khosla email that made $500,000 land in his account and moved his company to Silicon Valley in a week

- Joining YouTube when it lost money on every single view, and board meetings with Eric Schmidt about shutting it down

- The skip button every salesperson said would kill revenue, and how it went from $0 to $1 billion in 18 months

- Selling Coda to Grammarly, and why he needs a sense of purpose more than a sense of ownership

so much more!

𝐓𝐈𝐌𝐄𝐒𝐓𝐀𝐌𝐏𝐒

(00:00) Trailer

(01:07) Shishir Mehrotra, CEO, Superhuman

(01:32) Making the Lego robotics world championships four times with his daughters

(08:59) His dad only paid for majors where the books are 50 years old

(12:18) Why most people should not start a company

(14:47) The Vinod Khosla email that moved $500,000 in one afternoon

(20:15) Joining YouTube when it lost money on every view

(25:50) Board meetings with Eric Schmidt about shutting YouTube down

(35:20) The skip button that went from $0 to $1B in 18 months

(40:30) Susan Wojcicki and the 55/45 creator revenue split

(45:54) Sketching Coda on a notepad by his bed

(53:52) Why he sold Coda to Grammarly

(59:30) Purpose over ownership and zero startup pride

(1:01:45) The bundling theory he built with Daniel Ek at Spotify

(1:04:49) Superhuman's AI agents and 60% of auto-drafted emails sent

(1:09:37) Why AI will make teams bigger

(1:15:32) Outro

Follow Shishir

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X: https://x.com/shishirmehrotra

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Today I walk with Noor Siddiqui, founder and CEO of Orchid. Noor was a Thiel Fellow at 17, studied CS at Stanford, and has raised $16.5M for Orchid from Vitalik Buterin, Brian Armstrong, Balaji Srinivasan, and Elad Gil, and now she's out to end what she calls the genetic lottery. She gets into why she thinks people won't have sex for babies anymore, and what she'd pick for her own kid if the tech existed today.

We get into:

- Why she calls the genetic lottery "super evil and unfair"

- The 5–10% chance of genetic disease if you conceive the old-fashioned way

- Her most controversial take: people aren't going to have sex for babies anymore

- Why Michael Phelps is only Michael Phelps because of a genetic lottery

- Tetrachromats, 100 million colors, and what "leveling the playing field" actually means

so much more!

Timestamps

(00:00) Trailer
(00:53) Noor Siddiqui, Founder and CEO, Orchid
(01:04) The flashmob dance proposal
(11:15) Applying to the Thiel Fellowship at 17
(24:22) Founders raising $50M and losing $100M
(31:48) Taking advice from the 500 IQ nerd
(35:36) Why genetics shape everything
(51:03) What is a super baby
(54:55) Sequencing 3 billion letters and why the genetic lottery is evil
(1:01:16) People aren't going to have sex for babies
(1:02:43) Michael Phelps and the genetic lottery
(1:07:21) Escaping the code we were stuck with 
(1:20:21) Upgrading all humans would make her cool
(1:22:20) Outro

Follow Noor

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

X: https://x.com/noor_siddiqui_

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

Today I walk with Gagan Biyani, founder and CEO of the Horowitz Andreessen Academy. Gagan co-founded Udemy, which grew into a multibillion-dollar public company, built Sprig, co-founded Maven, and started his first profitable business at 13, and now he's building a16z's new school for young builders, backed by $42 million. He gets into the $60M company he had to shut down, why his investors backed him again anyway, and why a Harvard dropout means nothing to him.

We get into:

-Starting a debate camp at 13 that ran 50% EBITDA margins, and landing in the principal's office for it

-Sprig: $60M raised, 1,300 employees, a shutdown, and investors who backed his next company anyway

-Why the Academy flips college around, with students building instead of attending class

-The call from Andrew Chen and ten meetings with Marc Andreessen and Ben Horowitz that became the Academy

-Why he tells 18-year-olds that raising VC is a ten-year commitment

so much more!

𝐓𝐈𝐌𝐄𝐒𝐓𝐀𝐌𝐏𝐒
(00:00) Trailer
(01:01) Gagan Biyani, Founder & CEO, Horowitz Andreessen Academy
(02:23) A one-year fellowship built around building, not class
(03:55) The three skills that are AI proof
(08:16) Grandparents from Rajasthan who never finished high school
(09:31) Starting a debate camp at 13 with 50% margins
(12:59) Why schools are afraid of student agency
(18:33) Seven jobs, three years, and rarely going to class
(18:46) Why most professors don't care about teaching
(25:41) What Udemy and Maven taught him
(33:32) Raising $60M at Sprig, shutting down, and getting backed again
(38:16) Why raising VC at 18 is a ten-year commitment
(39:21) The call from Andrew Chen that started the Academy
(41:18) Why the best builders will pick a16z over MIT or Harvard
(43:17) 50 founding students, tuition-free
(45:46) Why a Harvard dropout means nothing to him
(51:42) Outro

Follow Gagan
LinkedIn: https://www.linkedin.com/in/gaganbiyani/
X: https://x.com/gaganbiyani

Follow Luba
Instagram: https://www.instagram.com/lifeoflubaa/
LinkedIn: https://www.linkedin.com/in/yudasinal/

Today I walk with Edward Kim, co-founder and CTO of Gusto. Edward built Gusto with two Stanford classmates into a $9.5B payroll platform running 300,000 small businesses, made over $1M selling Android apps on the side, and after a decade managing engineers, he's writing code again to ship an AI co-founder for the back office his mom used to run when he was a kid. He gets into why his doctor dad handed him a Paul Graham essay in the car, and the unfairness technical co-founders feel while business co-founders raise the money.

We get into:

-Making $700K a year selling Android apps after his first startup shut down

-Why his doctor dad handing him a Paul Graham essay changed his career

-His mom running the entire back office of his dad's medical practice while raising three kids

-The unfairness technical co-founders feel while business co-founders get wined and dined by investors

-Going back to code after 10 years managing engineers to ship an AI co-founder for small businesses

so much more!

(00:00) Trailer
(00:51) Edward Kim, Co-Founder and CTO, Gusto
(00:57) The elaborate escape rooms he builds for his wife Yuna
(03:04) The San Francisco half marathon on a bet that reconnected him with Josh
(05:32) Making $700,000 a year selling Android apps
(10:25) Screenshot It, the $7 app for a feature Android didn't have
(18:31) His mom running the entire back office of his dad's medical practice
(26:22) The Paul Graham essay his doctor dad handed him in the car
(29:51) Getting into Y Combinator with Gary as a partner
(32:49) The unfairness technical co-founders feel while business co-founders raise money
(36:51) After 15 years of co-founding, why the workload evens out
(56:07) Building Gusto Co-Founder for the small business back office
(1:15:01) His life philosophy in one sentence
(1:15:08) Outro

Follow Edward

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

X: https://x.com/edawerd

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Instagram: https://www.instagram.com/lifeoflubaa/

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

X: https://x.com/LubaYudasina

Today I walk with Julian Weisser, founder of Solo Founders and co-founder of On Deck. Julian has run 27 ODF cohorts, helped more than 1,000 founders collectively raise over $2 billion, and spent eight years matching people with co-founders, and now he believes AI has made the co-founder optional. He gets into the $400,000 payout demand from a co-founder who did two months of work, and why he compares co-founders to car phones now that solo founders have the cell phone.

We get into:

- Calling his own teenage taste in jazz "musical masturbation," and the moment that actually taught him to love it

- The $400,000 payout a co-founder demanded for two months of work, and why there was no mechanism to force them out

- His run co-founding On Deck, where 27 cohorts helped over 1,000 founders raise $2B+, and why he thinks the co-founder problem is basically already solved

- The Hacker News post that got almost no response except one email from Dropbox's first employee

so much more!

Timestamps

(00:00) Trailer
(00:51) Julian Weisser, Founder, Solo Founders
(02:06) Calling his old jazz taste "musical masturbation"
(20:17) 27 cohorts, thousands of founders, more reps than any VC
(35:50) The $400K co-founder payout demand
(39:45) The Hacker News post that led to Dropbox's first employee
(44:45) Golden Gate Park was built from sand dunes
(54:50) Why co-founders have seasons, not forever contracts
(58:53) The "oddballs" who never wanted co-founders, including Loyal's Celine Halioua
(1:00:59) Co-founders are the car phone. Solo founders are the cell phone.
(1:06:47) Why owning less equity can mean more freedom
(1:16:18) His two-word life philosophy: keep going
(1:16:34) Outro

Follow Julian
X: https://x.com/julianweisser
LinkedIn: https://www.linkedin.com/in/julianweisser/

Follow Luba
Instagram: https://www.instagram.com/lifeoflubaa/
LinkedIn: https://www.linkedin.com/in/yudasinal/
X: https://x.com/LubaYudasina

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Today I walk with Spenser Skates, co-founder and CEO of Amplitude. Spenser shut down his first startup, a voice-to-text texting app called Sonalight, a year after it got into Y Combinator, spent years going through what he calls an identity crisis moving from founder to CEO, and has grown Amplitude into a public company of roughly 800 people, and now he's rebuilding it around Wave, an AI engine that rewrites products using their own data.

We get into:

• Why he and his co-founder Curtis intentionally shut down Sonalight a year after Y Combinator, even after a Demo Day that got them press and tens of thousands of downloads

• The customer research rule he now enforces at Amplitude: talk to 30 teams before writing a line of the original product, and only build if a real chunk of them say yes

• Wave, Amplitude's new AI engine that scans a product's own data and rewrites its features, including one fix that tripled a customer's AI usage overnight

• Why he thinks the most ambitious operators, including a SaaS "legend" he looked up to, are driven by insecurity rather than confidence

• The Norman Borlaug story that convinced a 20-something Spenser to bet his entire career on tech instead of academic research

So much more!

TIMESTAMPS

(00:00) Trailer

(01:08) Spenser Skates, Co-Founder & CEO, Amplitude

(01:36) Why video games stopped feeling like real achievement

(08:50) Growing up in Cambridge and hating a life scripted by other people

(15:04) The Norman Borlaug story that convinced him to bet on tech

(20:14) Convincing Curtis to leave Google and co-found a company

(24:55) Playing StarCraft until 2am while pretending to build the startup

(29:04) The exact test for knowing when to kill a startup

(32:30) Why half a founding team's time should go to customers, not code

(35:02) The identity crisis of going from founder to CEO of 800 people

(40:35) Burning the boats on the old Amplitude to go all in on AI

(42:33) Wave: the AI engine that rewrites products using their own data

(48:49) Why insecurity, not confidence, drives the most ambitious operators

(56:01) Betting on his partner Anne and being "single until Series B"

(1:05:00) Outro

Follow Spenser

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

X: https://x.com/spenserskates

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

Automate Compliance (and get $1,000 off!!) - https://vanta.com/luba

Today I walk with Coco Mao, CEO and co-founder of OpenArt, an AI visual storytelling platform. Coco spent years as an engineer at Google, ran her own startup inside Google's internal startup incubator, and built OpenArt through six months of weekly pivots until a prototype built in under three days went viral on Hacker News, and now she's betting the entire company on a new category she calls vibe directing.

We get into:

• Why she quit her Google side-hustles, including the Amazon fidget-toy business she overstocked right before founding OpenArt
• The six-month stretch of weekly pivots that ended with a three-day prototype going viral on Hacker News
• OpenArt's bet on "vibe directing," the video-agent category she compares directly to vibe coding
• What actually separates good AI-generated work from "total slop": idea and taste, not the tools
• Launching the AI Personality Awards with Fanvue, and why she thinks AI influencers will make human creators more valuable, not less

So much more!

Timestamps

(00:00) Trailer 
(00:54) Coco Mao, CEO & Co-Founder, OpenArt 
(03:11) Selling fidget toys on Amazon before quitting Google 
(04:56) Meeting co-founder Jon inside Google's startup incubator 
(08:01) Betting on AI art in 2022, a non-consensus space 
(08:18) The weekly pivot that led to a Hacker News-viral prototype 
(14:09) Naming OpenArt and getting mistaken for OpenAI 
(14:56) Raising a seed round on speed, not metrics 
(19:11) Hire fast, fire very fast 
(20:01) Why OpenArt survived while image-gen rivals disappeared 
(23:00) Vibe directing: the next category after vibe coding 
(28:08) What separates good AI work from total slop 
(39:40) Launching the AI Personality Awards with Fanvue 
(43:46) The hardest part of scaling: reinventing yourself 
(50:22) The one founder belief she now thinks is wrong 
(51:20) Outro

Follow Coco

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

X: https://x.com/cocokechun

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X: https://x.com/LubaYudasina

Today I walk with Packy McCormick, founder of Not Boring and Not Boring Capital. Packy built Not Boring into a top newsletter on Substack, spent years in finance before leaving to write full time, and now invests in the same kinds of companies he writes about through Not Boring Capital. He gets into the moment his growth flatlined during the 2022 market crash and what it freed him to do, and why he considers Not Boring's founding mission basically complete.

We get into:

• Why he passed on investing in the friend who now runs a robotics company valued at $1 billion
• The real "nobody gives a s***" moment that came after Not Boring's meteoric growth crashed in 2022
• The clay pot experiment behind why he still writes 30 imperfect essays a year instead of a few polished ones
• Why he thinks Anthropic's careful, downside-focused posture on AI is a little too pessimistic
• Why he doubles down on his strengths instead of trying to fix a below-average memory

So much more!

Automate Compliance (and get $1,000 off!!) - https://vanta.com/luba

TIMESTAMPS

(00:00) Packy McCormick, Founder, Not Boring & Not Boring Capital

(01:02) Weekly business coaching calls with his mom

(06:15) Passing on the friend who built a $1 billion robotics company

(20:19) The moment nobody gave a s*** anymore

(31:02) Being scared of infinity as a kid

(34:50) Why Anthropic's pessimism wears him out

(36:19) Retiring Not Boring's founding mission

(41:09) Telling his pregnant wife he was starting over

(45:27) The clay pot experiment behind his writing process

(56:00) Double down on strengths, not weaknesses

(58:52) What made Colossus's writer profiles so good

(1:03:18) $470 million for micro nuclear reactors

(1:04:19) The GLP-1 side effect nobody saw coming

(1:07:58) What brought him joy this week

Follow Packy

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

X: https://x.com/packyM

Website: https://www.notboring.co

Follow Luba

Instagram: https://www.instagram.com/lifeoflubaa/

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

X: https://x.com/LubaYudasina

Automate Compliance (and get $1,000 off!!) - https://vanta.com/luba

Today I walk with Zach Lloyd, founder and CEO of Warp. Zach is a former Principal Engineer at Google, where he led the Google Sheets team. Zach scaled his first startup, SelfMade, to 150 employees before it fell apart, and now he’s raised over $73 million for Warp from Sequoia and Google Ventures. He's betting the whole company on AI. He talks about the AI feature Warp built before Claude Code and ChatGPT existed, why not going harder at it is one of his biggest regrets as a founder, and what it's like having Marc Benioff as his cousin.

We get into:

• The AI feature Warp shipped before ChatGPT even existed, and why building something like Claude Code six months early still turned into one of his biggest regrets
• His first startup, SelfMade, scaling to 150 employees and multiple millions in revenue without ever finding real product market fit
• Why he calls hiring "just sales," and why he'd rather hand over equity than compete on salary
• Why he barely opens a spreadsheet anymore, and which AI-era tools he thinks actually survive

so much more!

Timestamps

(00:00) Trailer

(00:59) Zach Lloyd, Founder & CEO, Warp

(01:03) Grandfather Lloyd K Lloyd, San Francisco's original salesman

(04:42) Marc Benioff is his cousin

(21:33) The humility lesson from Google Sheets' original creator

(27:07) SelfMade: 150 employees, still not a real business

(34:04) Why hiring is really just sales

(39:32) Nearing a million terminal users

(41:18) Building AI before Claude Code and Codex existed

(42:52) Only going halfway in on AI

(1:03:09) Why he barely opens a spreadsheet anymore

(1:10:10) Warp is automating 30% of its own engineering work

(1:11:12) Building automated cloud factories

(1:14:49) Almost naming the company Cursor

(1:15:48) Never living on Saint Mark's again

Follow Zach

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

X: https://x.com/zachlloydtweets

Website: https://warp.dev

Follow Luba

Instagram: https://www.instagram.com/lifeoflubaa/

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

X: https://x.com/LubaYudasina

Automate Compliance (and get $1,000 off!!) - https://vanta.com/luba

Today I walk with Michelle Lim, CEO of Flint, an autonomous web and ads building platform. Michelle interned at Meta, Slack, and Robinhood, grew Warp from employee number two to 500,000 developers over four years across engineering, marketing, and sales, and now she's building Flint to charge by outcome instead of software. She gets into her origin story that pushed her to fix marketing after four years at Warp, and why she thinks the market VCs have valued at $10 billion is actually worth $100 billion.

We get into:

-Why turning down medical school made her "a family disappointment," and the villain origin story that pushed her to build Flint after four years fixing marketing at Warp

-Her "five Infinity Stones" framework: engineering, product, marketing, customer success, and sales, for knowing exactly when she was ready to leave Warp and start her own company

-Why VCs have historically stayed away from funding marketing startups, and her bet that AI turns a market capped at HubSpot's $10 billion into a $100 billion opportunity

-Her framework for writing LinkedIn hooks that lead with credibility and actually convert strangers into customers and hires

So much more!

Timestamps

(00:00) Trailer

(00:32) Intro

(01:21) Singapore's definition of success: doctor, lawyer, or government scholar

(02:31) Applying to Yale on a whim, thanks to a one-school early action rule

(06:16) Why a startup was "one of the lowest prestige things" she could do at Yale

(10:48) Discovering computer science through a Yale entrepreneurship club

(16:21) What she took, and left behind, from Meta, Slack, Robinhood, and Warp

(19:48) Winning an hour alone with Mark Zuckerberg on her best internship project

(22:12) Sheryl Sandberg's leadership lesson: repeat the same story until it lands

(27:59) Her framework for writing LinkedIn hooks that actually convert

(35:53) Bodies "piling up" in Covid-era New York, and the push to join Warp

(40:53) Telling Warp's CEO upfront that she wanted to be a founder

(47:47) The "five Infinity Stones" framework for knowing when to start Flint

(54:47) Why VCs avoid funding marketing startups, and her bet on a $100 billion market

(1:00:23) Meeting her co-founder through a 200-question questionnaire, and his parents' interview

(1:09:14) Never try to save money on a lawyer

Follow Michelle

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

X: https://x.com/michlimlim

Follow Luba

Instagram: https://www.instagram.com/lifeoflubaa/

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

X: https://x.com/LubaYudasina