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

Follow Luba

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

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

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

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

Today I walk with Blake Scholl, founder and CEO of Boom Supersonic. Blake was roughly Amazon's 200th engineer, spent more than a decade building XB-1 into the first supersonic jet made outside a government or military, and got the US ban on supersonic flight repealed after breaking the sound barrier, and now he's scaling Boom toward carrying passengers in 2030. He gets into the six years Boom spent waiting on Rolls-Royce for an engine, and why that breakup turned out to be the best gift the company ever got.

We get into:

• Why he'd rather be a "dark matter entrepreneur" who tried and failed than spend his life asking what if
• The six years Boom spent trying to get Rolls-Royce to build a custom engine, and why losing that deal is what made the business financially viable
• Why "work on something you know about" is terrible advice, since what you know is far easier to change than what you love
• How a parenting lesson turned into the practice that built candor inside Boom's staff meetings

So much more!

𝐓𝐈𝐌𝐄𝐒𝐓𝐀𝐌𝐏𝐒

(00:00) Trailer

(00:41) Intro

(01:39) The day XB-1 broke the sound barrier

(05:40) 2,000 pounds overweight and called the Theranos of aviation

(09:15) How big a dent can we make in the universe

(12:01) Bill Gates and the dark matter entrepreneur

(14:55) Mom's advice: work on something you already know

(17:12) The flying lesson at 19 that decided everything

(23:17) Starting Boom with three kids under two

(24:39) The mistake dinner that became a staff meeting

(27:22) Why the Rolls-Royce breakup was the best gift Boom got

(30:37) Brian Chesky and permission to make the big swing

(34:29) Amazon at engineer 200 and automating ads at 22

(37:58) Congestion price the entire road network

(40:12) "I'd be proud of you for trying"

(43:58) The $750K prize to fly supersonic

(44:33) Outro

Follow Blake

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

X: https://x.com/bscholl

Website: https://boomsupersonic.com/

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 Ann Miura-Ko, co-founding partner of Floodgate. Ann has spent almost 18 years building Floodgate around a deliberately small, non-consensus fund model, made early bets on companies like Lyft and TaskRabbit, and teaches entrepreneurship at Stanford, and now she's watching AI rewrite the lean startup playbook in real time. She gets into the AI agent inside one portfolio company that quietly caught millions of dollars in missed credit, and why she believes not losing is not the same as winning.

We get into:

• Why she waited nearly 18 years to grow Floodgate's fund size, and how staying small means a $1 billion exit still moves the needle for her investors
• Making debate opponents cry for a slice of pizza, and the permission that gave her to be disagreeable for the rest of her career
• SmarterDx, the company she couldn't get other investors to take seriously at Series A, that went on to exit for over $1 billion
• The math behind "founder friendly" investing, and why a $100M exit barely registers against a $1 billion fund

So much more!

TIMESTAMPS

(00:00) Ann Miura-Ko, Co-Founding Partner, Floodgate

(01:35) Making debate opponents cry for a slice of pizza

(05:41) Truth-seeking VS defending your ego

(11:12) How Mike Maples treated her as an intellectual equal from day one

(18:04) Being told she was "average" before finding her calling

(26:07) How AI is rewriting the lean startup playbook

(36:35) Floodgate's bet to stay small while other firms scale up

(39:53) The AI agent that caught millions in missed credits

(46:43) SmarterDx: the $1B exit no other investor wanted

(48:49) The real math behind a "founder friendly" investor

(53:55) Category design and why Lyft had to break the law to launch

(1:08:39) The Toyota Corolla he drove for 25 years to buy her a piano

(1:11:53) Being the only woman in her electrical engineering class

(1:16:37) Turning 50 and her year of saying yes

Follow Ann

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

X: https://x.com/annimaniac

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 Jean-Denis Greze, co-founder and CEO of Town, an AI on-ramp platform for individuals and businesses. Jean-Denis is the former CTO of Plaid, led engineering through a blocked $5.3B Visa acquisition, and walked away from the C-suite at 45 to start over from zero, and now he's turned a scrapped AI tax-prep startup into a $55M Series A company backed by Andreessen Horowitz. He gets into the week he decided to kill a business that was actually working, and why he refuses to call Town an "AI assistant."

We get into:

• Why he waited until 45, after seven years as Plaid's CTO, to become a founder for the first time
• The week he and his co-founder killed a working, revenue-generating tax-prep startup because it wasn't going to be a rocket ship
• Town's real bet: not a smarter AI assistant, but an onboarding layer that gets normal people leverage from AI without writing a single prompt
• His "accelerators, table stakes, foundations" framework for staying ahead of OpenAI, Gemini, and Google
• Why turning "uncool" work into cult culture, from Dropbox's Team Cash to Plaid's colorful tights, built teams that stuck around

so much more!

Timestamps

[00:00:00] Trailer

[00:00:43] Intro

[00:01:41] Leaving Plaid at 45 to become a founder

[00:06:01] Redefining success beyond IPOs and revenue

[00:11:56] The YC prodigy myth VS two decades of hard-earned instinct

[00:19:47] The stress gap between being an exec and being the founder

[00:25:35] Time-boxing family, health, and friends at Series A

[00:32:11] Betting on AI tax prep and grinding for a year

[00:38:13] The week they decided to shut down a profitable business

[00:41:53] The worst three weeks: telling the team and winding down right

[00:57:47] The accidental prototype that became Town

[01:04:15] Why Town calls itself an on-ramp, not an AI assistant

[01:12:29] Beating OpenAI, Gemini, and Google's home-field advantage

[01:20:31] Team Cash: making "uncool" work fun at Dropbox and Plaid

[01:32:02] Landing Andreessen Horowitz and Forerunner for the Series A

[01:37:41] Outro

Follow Jean-Denis

LinkedIn: linkedin.com/in/jeandenisgreze

X: https://x.com/jgreze

Website: https://town.com

Follow Luba

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

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

X: https://x.com/LubaYudasina

Today I walk with Laura Deming, co-founder of Until, a reverse cryopreservation company in San Francisco. Laura got interested in longevity at eight, started working in Cynthia Kenyon's lab at UCSF at 12, and spent years backing the field as an investor through the Longevity Fund. She now builds technology to pause biological time, starting with donor organs and building toward whole-body medical hibernation. 

We get into:

-The conference talk she was not supposed to give, and how it ended her VC chapter

-What "transcend death" actually means once you press on it, tested with a teleporter to Mars

-Why San Francisco kills intuition, and the breakdown in her mid-20s that made her protect hers

-The big magnet, and rewarming an organ in about a minute

-Why transplant patients live inside a two-hour radius with a pager on them at all times

so much more!

Timestamps

00:00:00 Trailer 
00:00:48 Intro 
00:01:35 "I love science" and the things that have stayed constant 
00:05:13 A childhood without rules and reconstructing what normal means 
00:07:03 What is actually worth preserving when a person dies 
00:13:00 The Dreaming Machine and the film that never got made 
00:19:02 When you could not say the word aging out loud in the lab 
00:22:55 Emailing Cynthia Kenyon at 12 and the day her life started 
00:28:49 The talk that made her leave VC for cryo 
00:32:39 San Francisco as an intuition killer
00:35:04 Molecules in clockwork synchrony and feeling loved by the universe 
00:44:39 The big magnet and rewarming an organ in about a minute
00:46:19 The two-hour radius and the pager that runs a transplant patient's life 
00:53:50 Her best arguments against her own work 
00:58:44 The teleporter to Mars and what dies in the process 
01:01:42 Outro

Follow Laura
X: https://x.com/LauraDeming?lang=en
LinkedIn: https://www.linkedin.com/in/laura-deming-b255362a/
Website: https://www.untillabs.com/

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

Today I sit down with Avichal Garg, co-founder and General Partner at Electric Capital. Avichal has built and sold companies, worked inside early Google and Facebook, served as a visiting partner at Y Combinator, and now backs founders across crypto and frontier tech.

We get into:

-Why founders are more like artists than operators

-What actually compounds a person's trajectory

-His "software eating money" thesis behind Electric Capital

-Why honesty ends up being the real edge in venture

so much more!

Timestamps

00:00:00 Trailer

00:00:44 Intro

00:01:00 Watches, luxury markets, and the AI parallel

00:12:48 Opportunity is a luxury

00:14:43 Founders as artists, not just operators

00:18:26 Authenticity and cutting through market noise

00:24:38 Betting on outliers as a life philosophy

00:37:58 Storytelling as a founder superpower

00:55:41 How Elad Gil helped launch Electric

01:07:55 Why crypto was the wedge for Electric

01:19:28 Why he prefers market corrections

01:31:00 The firms Electric was modeled after

01:36:21 Honesty as the core operating principle

01:42:15 Over-committing resources to founders

01:51:03 Dodging SBF and reading fake authenticity

02:01:40 Outro

Follow Avichal
LinkedIn - https://www.linkedin.com/in/avichalgarg/

X: https://x.com/avichal?lang=en

Follow Luba

Instagram: https://www.instagram.com/lifeoflubaa/
Linkedin:https://www.linkedin.com/in/yudasinal/

X: https://x.com/LubaYudasina

Today I'm talking to Ben Rudolph, co-founder and CTO of Peregrine Technologies, to trace his path from Stanford gymnastics to building one of the fastest-growing companies in government technology. They discuss his time at the UN working with refugees, the 18 months he and co-founder Nick Noone spent embedded inside a police department, surviving the early "wilderness" of company building, and how Peregrine grew into a multi-billion dollar business. The conversation also covers leadership lessons, company values, and balancing fatherhood with running a fast-scaling company.

Timestamps:
00:00:00 Trailer
00:01:18 Intro
00:01:21 Stanford gymnastics and meeting Nick
00:09:06 Working with refugees at the UN
00:16:20 Deciding to start the company
00:19:10 Moving into a police department for 18 months
00:26:44 Where the Peregrine name comes from
00:31:23 Winning the California RFP
00:41:47 Growth from wilderness to product-market fit
00:44:58 Biggest mistake and hardest lessons as a leader
00:48:39 Becoming a father while scaling the company
00:48:52 How Peregrine uses AI internally and externally
00:56:01 Life philosophy and closing thoughts
00:57:00 Outro

Links:

Ben Rudolph
Website: https://www.benrudolph.info/
Instagram: https://www.instagram.com/__benrudolph/?hl=en
LinkedIn: https://www.linkedin.com/in/brudolph

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