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My First MillionI Sold A Company For $800M At 29... What I’m Doing Now | Jack Smith Interview (#470)
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CHAPTERS
- 0:00 – 2:44
Meet Jack: The Amazon Spreadsheet and Return Hacks
Sam Parr introduces Jack Smith, who sold his company for around $800M at 29, and the hosts joke about his product-testing obsession. Jack describes getting banned from Amazon and returning a whole Bonobos wardrobe each year.
- •Jack sold his company for about $800M at 29
- •He tracks purchases in a spreadsheet and tests dozens of versions of products
- •He has been banned from Amazon several times
- •He exploited Bonobos' 365-day return policy to refresh his wardrobe yearly
- 2:44 – 7:26
The Vungle Story and What AppLovin Did Differently
Sam recaps how Vungle began as a mocked-up pitch to developers and grew into a video ad network. Jack and Shaan discuss why AppLovin, which launched later, became far bigger, and Jack shares a lead-gen hack using people in Pakistan to play games.
- •Vungle was built after developers committed spend to a mocked-up concept
- •Jack says you don't have to be first to market to be the biggest
- •AppLovin offered every ad format, not only video, and had a more technical founding team
- •Vungle had a team in Pakistan play mobile games and log which ad networks served each ad
- 7:26 – 11:37
Why Jack Isn't Starting Another Company
Sam asks whether Jack will ever return to business. Jack explains that his early drive came from a chip on his shoulder, which is gone, and that he now wants impact, including a digital detox retreat in Portugal.
- •Jack says he isn't retired but isn't chasing another billion-dollar company
- •His early success was fueled by having something to prove
- •Many founders in their group chat struggle after selling their first company
- •He is setting up charities and a digital detox place in Portugal where money isn't the core metric
- 11:37 – 16:32
Silent Retreats, Vipassana, and a Gentler Alternative
Sam notes Jack was into ayahuasca and silent retreats long before they became popular. Jack describes how extreme Vipassana is and explains the gentler Indonesian retreat he prefers, which he wants to expand to other continents.
- •Sam recalls Jack doing ayahuasca and a three-week silent retreat years before they became trendy
- •Vipassana involves concrete pillows, no eye contact, and 3–5 AM wake-ups
- •Jack's alternative, inspired by Bill Gates' Think Week, has only a no-talking rule
- •He wants to expand the concept, starting with Portugal then America
- 16:32 – 24:32
Business Idea: Reseller Layers Like Nomad Capitalist
Jack describes Nomad Capitalist as a marketing-led reseller for tax lawyers who are bad at marketing. Shaan connects it to the Rich Dad and Dave Ramsey models, which he calls router businesses that funnel trust and traffic to service providers.
- •Nomad Capitalist charges a $25,000 retainer for a report and takes referral fees from lawyers
- •Jack suggests building branded reseller layers for other industries that communicate poorly
- •Shaan says a Rich Dad-linked service marked up a tax strategy about 3x
- •Shaan describes Dave Ramsey's certified advisor network as lead gen, estimating a $300M+ a year empire
- 24:32 – 32:35
RTFM: Learn the AI Tools Others Won't
Jack explains that reading the manual for tools like Midjourney solved a problem that hired experts couldn't, and that most people are too lazy to do it. The group discusses AI consultants, the Casetext acquisition, and Mark Cuban's identical RTFM approach.
- •Reading the Midjourney guide solved in 15 minutes what hired experts failed at
- •Jack suggests becoming an expert in new AI tools and selling workshops or vertical-specific books
- •He cites LexisNexis's Casetext acquisition and its mention of eight prompts, which Shaan says oversimplifies it
- •Sam and Shaan cite Mark Cuban reading software manuals nightly to build Micro Solutions
- 32:35 – 38:58
Hacking New Products: Recording the iPhone Screen
Jack explains that brand-new products have exploitable gaps, using Vungle's iPhone screen-recording hack as an example. He applies it to the Apple Vision Pro, suggesting someone buy, hack, and return it within 14 days.
- •Early on, the iPhone screen couldn't be recorded, so an intern jailbroke a returnable device in 48 hours
- •Proprietary videos let Vungle offer them free for advertisers spending over $25,000
- •Competitors had to use cameras or agencies
- •Jack says he'd try to hack the Vision Pro on day one to find a proprietary edge
- 38:58 – 45:08
Law of Attraction in Practice: Conviction and Fundraising
Jack explains why he believes in a practical version of the law of attraction, using his roommate's fundraising turnaround and his own confidence with investors. Sam recalls Jack staying calm when his money was nearly gone, and Jack describes his secondary sale and day trading.
- •Jack favors a practical version: define what you want, feel it, and act
- •His roommate raised a seed round after going all in with conviction
- •Conviction projects through micro signals and changes how rejection is interpreted
- •Sam recalls Jack being calm with only single-digit thousands left
- •Jack sold a secondary of about $500K and lost money day trading
- 45:08 – 56:07
Belief Cycles and Personas: Tony Robbins and Sasha Fierce
Shaan lays out a vicious versus virtuous cycle of belief, action, and results. Jack discusses feeling versus saying it and adopting personas like Beyoncé's Sasha Fierce, and Shaan shares Tony Robbins' idea of choosing which version of yourself drives.
- •Low belief leads to weak action and bad results, reinforcing low belief
- •High belief leads to massive action and results
- •Action is required alongside belief
- •Beyoncé adopts a fierce persona before going on stage
- •Shaan says we hold multiple versions of ourselves and can practice calling the best one on command
- 56:07 – 1:00:10
Humility and Remembering How People Treat You
Sam praises Jack's humble, mild-mannered nature. Jack explains why he stays humble and talks to everyone, including the man who collects his recycling, and recalls a London VC who dismissed him early on.
- •Sam says Jack is successful across many areas yet never brags
- •Jack has in-depth conversations with a trash collector in Portugal
- •Where people are now isn't where they'll be in 10 years
- •Jack still remembers a VC who ended a meeting abruptly and wouldn't share deal flow with him
- 1:00:10 – 1:09:35
Being Interested: First-Principles Thinking and the Baby Named Baby
Shaan calls Jack the most interesting man in the world because he is interested in so many things. Jack explains how first-principles research led Vungle to charge per install, and Sam brings up Jack naming his daughter Baby for a year.
- •Jack's team researched ad networks for a week and reached different conclusions from industry veterans
- •Vungle bet on charging by installs rather than video views
- •Jack didn't want to rush a name before leaving the hospital and found he could change it within 12 months
- •His daughter was named Baby on the birth certificate and the idea of letting her pick her own name came from a ritual he described
- 1:09:35 – 1:15:22
Baby Hacks: Product Testing and the Digital Night Nanny
Sam describes Jack's elaborate gift boxes, and Jack talks about researching baby products. He also explains his remote night monitoring setup, which only wakes the parents if the baby cries for over seven minutes.
- •Jack sends gift boxes with detailed notes explaining why each product is best
- •He may turn his baby product research into an e-book and shares favorites on Twitter
- •A virtual assistant in India watches the baby cam overnight with specific instructions
- •Jack says he sleeps better than before the baby, with the baby needing him about once every two months
- 1:15:22 – 1:26:16
Unschooling and Rethinking Education
Jack explains why he doubts universities will exist in 20 years, using the book Don't Tell Me I Can't about an unschooled boy. He describes forest school, his plans for a self-directed program, and responds to Shaan and Sam's concerns about unmotivated kids and credentials.
- •Unschooling has no curriculum and the child learns what is useful to them
- •The book's author built businesses and managed land by 13
- •Jack's daughter currently attends forest school and he wants to create a similar program for older kids
- •Shaan shares his sister's nature school observation that kids have more energy and curiosity
- •Jack acknowledges unmotivated kids and credentialed careers as open questions
- 1:26:16 – 1:33:23
Wrap-Up: Book Pick, Buckwheat Pillows, and Supplement Closet
Shaan praises Jack's independent mind, and Jack recommends Don't Tell Me I Can't. The conversation shifts to Jack's buckwheat pillow, Nick Gray shipping pillows to hotels, and Jack's supplement closet with its one standout, shilajit.
- •Shaan says Jack is independent-minded, curious, and not needlessly competitive
- •Jack recommends Don't Tell Me I Can't, a short book that challenges assumptions about education
- •Jack says an adjustable buckwheat pillow cured his neck pain
- •Sam says Nick Gray has pillows shipped to hotels
- •Sam recalls Jack's supplement closet where only shilajit stood out
