Jack Smith — who co-founded Vungle, a mobile video ad network that sold for roughly $800 million when he was 29 — talks through why he has no desire to start another company, his plan to build a digital detox retreat in Portugal, and a handful of business ideas he’s noticed but isn’t pursuing. The conversation covers practical Law of Attraction, the RTFM business strategy, hacking the iPhone screen to create Vungle’s moat, and unconventional parenting choices — including naming his daughter “Baby” for her first year of life.
Speakers: Jack Smith (guest, Vungle founder, sold for ~$800M), Sam Parr (host), Shaan Puri (host)
Who Jack Smith Is [00:00:00]
Sam: We have Jack Smith — one of my best friends, in my wedding, one of the more interesting people I know. The top line: you started a company that you sold for about $800 million when you were 29. But you’re not here to brag. You’re here because you’re just a fascinating person.
Shaan: Before that, let me give context. Jack is maybe the most product-obsessed person I’ve ever met. His wife made him a birthday cake shaped like an Amazon box because he had an entire room in his house full of Amazon boxes — things he’d ordered to test. He had a spreadsheet tracking the purchase date of every item of clothing he owned, and he would return it all to Bonobos at day 340 of a 365-day return window to get a new wardrobe for free.
Jack: I got banned from Amazon a few times.
Sam: You’d think you have more in common with Shaan than you think — he’s planning his bowel movements, you’re planning your clothing returns in a giant spreadsheet.
Jack: I was also working 40 hours a week at Rogers Video — Canadian Blockbuster — in the summers. Paying for university at Manitoba. Supporting my parents. I wasn’t rich. I was just working. Actually, I’m maybe the exact opposite of a human optimizer. I’m human procrastination.
Building Vungle [00:06:00]
Sam: Tell the Vungle story. You had one idea in an accelerator that wasn’t working, and you mocked up a PowerPoint for a mobile ad network, got commitments from developers, hired a developer — Bryant, who’s now the co-founder of Webflow — and built the business. Seven years later you were doing a million dollars a day in revenue and sold for around $800 million.
Jack: Roughly. The core insight was: before Vungle, mobile ads were banner ads — the same crappy format that had failed on the desktop web. We were like: obviously these suck. Let’s do video ads instead. Ten times better. It seemed obvious.
What we didn’t account for: AppLovin launched about six to twelve months after us. They ended up at a peak market cap of $20-25 billion. Much bigger outcome than ours. One reason: they didn’t restrict themselves to video ads. They said “we don’t care what format you want to run — banner, video, whatever — we’ll take your money.” That breadth captured more market share.
The other factor was technical depth. I’m a crappy engineer. I could not build Vungle from scratch. AppLovin’s founding team was more technical and could do things we couldn’t.
Shaan: You also had a creative lead generation hack.
Jack: We hired about ten people in Pakistan. Their job was to play mobile games all day on iPhones and write down what ads they saw and which ad networks were running them. That was our lead gen database. They built it by playing games. AppLovin built the equivalent by scraping SDK source code. We did it manually. Works either way.
Why He Never Started Another Company [00:16:00]
Sam: You’re the only person I know who was incredibly successful at a very young age and has genuinely not started another company since. Everyone I know who exits eventually starts something else. You’ve resisted that for years.
Jack: When I look back, I think the reason I succeeded early was a chip on my shoulder. Doing a startup in London was hard, and I felt like people didn’t take me seriously. I wanted to prove something. After Vungle sold, I sat with it and realized: I don’t have that chip anymore. I don’t need more money. I don’t have something to prove.
We have a group chat of founders who sold their first companies and most of them describe the same crisis — they’re good at building companies, they don’t really need more money, but they do it because that’s what they’re good at and they can’t think of anything else.
For me, the conclusion I came to was: where can I have real impact? Not impact on a million people, but deeply impacting a few people. That’s more meaningful to me now than another company. So I’ve been setting up charities and working on a project I’m genuinely excited about.
The Portugal Retreat [00:22:00]
Jack: The project: I moved to Portugal to build a digital detox retreat — a place for people to switch off from technology and be in nature.
My inspiration was a place I found in Indonesia. Bill Gates has this “Think Week” concept where he goes to a cabin in the middle of nowhere and just reads for a week. I found this place in Indonesia that gave me all the benefits people talk about from Vipassana — ten-day silent meditation retreats — but without the extreme suffering. The Indonesian place has no rules except don’t talk to each other. You can make eye contact, read, do whatever you want. The food is amazing, grown on the farm attached to the property.
I came out of it every time feeling re-energized, mood off the charts. Meanwhile people who do proper Vipassana tell me it was the hardest experience of their life and they’d never do it again. Same benefits, completely different experience.
I’ve never found a place like that in the Western world. So I’m building one. Success for me isn’t necessarily making money — it’s people saying “that changed my life.” If it breaks even, fine.
Business Idea: The Marketing Layer [00:30:00]
Jack: I came across a company called Nomad Capitalist — this guy has made himself the thought leader for rich people who want to optimize their taxes and residency internationally. He has a podcast, a book, a great brand. You can pay $25,000 for a report recommending your tax strategy, or $75,000 to hang out with him on an island.
What he actually is: a reseller for tax lawyers. Tax lawyers are brilliant and terrible at marketing. He’s great at marketing. He takes a cut.
Dave Ramsey does the same thing at massive scale — his whole media empire, the books, the call-in show, it’s all lead generation. Go to his website and you’re routed to “Ramsey Trusted Advisors” — vetted local financial planners, mortgage brokers, insurance agents. They pay to be listed and pay for leads. His site gets 10 million visits a month. The Ramsey Trusted Advisor business alone is probably generating hundreds of millions.
Shaan: It’s a routing business.
Jack: Exactly. And the opportunity I see: there are probably twenty other industries where the actual service providers are great at their work and terrible at marketing. You build an amazing brand, write a book, go on every podcast, and become the trusted name. Then route customers to the underlying providers and take a cut.
RTFM as Business Strategy [00:38:00]
Jack: The other thing I’ve been thinking about: RTFM. Read the [expletive] manual.
I was working with someone on Midjourney — we were trying to get it to create mock-ups for the retreat property, blending images of the land with images of cabins. We even hired Fiverr experts. The results were terrible. Eventually I just sat down and read Midjourney’s own documentation. Within fifteen minutes I found the commands that did exactly what we’d been trying to do for days.
Mark Cuban wrote about this in an old blog post. He got his first few million building a company called MicroSolutions — essentially an IT services agency. His entire competitive advantage was that he stayed up late reading the manuals for every piece of software he installed. Nobody else read the manuals. He became an expert not because he was naturally smarter but because he did the thing that seemed too boring.
His exact words: “It turns out not a lot of people ever bother to RTFM. So people really started thinking I knew my stuff, and that’s all I was doing.”
The opportunity today: AI tools. Everyone is trying to use ChatGPT and Midjourney but nobody reads the documentation. You could spend nine days actually learning how these tools work, apply that to a specific vertical — lawyers, accountants, e-commerce — and charge businesses a premium because you know things they don’t.
Case in point: a company called Casetext was acquired by LexisNexis for $750 million. In the investor report, LexisNexis essentially said they were buying it because Casetext had developed eight proprietary prompts for legal queries in OpenAI. Eight prompts. That’s the asset.
Hacking Non-Obvious Barriers to Entry [00:48:00]
Jack: One of Vungle’s key advantages came from a hack. In 2010, you couldn’t record the iPhone screen. There was no built-in feature. My co-founder thought it was a waste of time, but I had a hunch that if you combined certain hardware with a jailbroken iPhone, it might work.
We had about a thousand dollars in the bank. I told our intern on his first day to take the company credit card, go to the Apple Store, buy the latest iPhone and iPad, and try to jailbreak it. I gave him 48 hours — and Apple’s 14-day return policy as our buffer, because we couldn’t actually afford to keep the devices.
We got it working. We could record the iPhone screen when nobody else could.
At the time, we didn’t know what to do with this. But when we built the video ad network, it became our moat. Every other ad network had to pay expensive agencies to produce video ads, or get developers to send all their assets over. We could just record the screen of the app and make a perfect video in-house.
We used that to create a licensing deal: we would make you the best-converting video ad in the industry, for free, if you committed $25,000 in ad spend with us. And you couldn’t use that video anywhere else. It locked clients in and gave us creative quality no one could match.
The broader lesson: when a brand new platform launches, there are always hacks and non-obvious capabilities that no one has explored yet. The people who explore them first build weird advantages. If I were 20 today, I’d go to the Apple Store on day one of the Vision Pro launch and spend two weeks trying to hack it.
Law of Attraction (Practical Version) [00:58:00]
Sam: You believe in the Law of Attraction. That surprises me — I’d have pegged you as a logical, empirical person.
Jack: Not the crystals version. There’s a book called “Practical Law of Attraction” and what it actually describes is something more grounded: clarity about what you want, and then massive action toward it.
I had a roommate who was trying to raise a seed round. He was stuck in this loop — he’d read about 18-year-olds getting into YC and feel sorry for himself, convinced investors didn’t respect him. He was projecting failure in every interaction and investors could sense it.
One day something shifted. He told me: “I’ve decided this is my one shot. I’m never going to try to raise money for a company ever again. I’m going all in.” He contacted every single person in his network asking for intros. Completely dropped the fear of looking stupid. Within a month he raised an amazing seed round. The business has since raised over $25 million.
What changed? His belief changed, which changed his action, which changed the results he got. That’s the Tony Robbins formulation: belief drives action, action drives results, results reinforce belief. It’s either a vicious cycle or a virtuous one, and the entry point is belief.
The reason I think this works is micro-signals. We project so much through body language and energy that we can’t consciously control. If you walk into a fundraising meeting already convinced it won’t work, investors feel that. If you walk in absolutely certain you’re going to succeed — not arrogantly, but genuinely — they feel that too.
When a VC asked how our fundraising was going and we had zero investors, I told him: “It’s going amazing. We have several top-tier people interested, we’re just deciding who’s the best fit.” He gave us a term sheet.
Shaan: That’s related to what Sam was saying earlier — when you were down to almost nothing in your bank account before Vungle sold. You were completely calm.
Jack: I had done a secondary, sold maybe $500,000 worth of shares. After taxes, California — maybe $250,000 left. I was advising startups, but they were paying me in equity, not cash. My money was running out and I was day-trading options to try to generate income — which, in retrospect, was idiotic. I would have done much better just putting it all in the S&P 500. Wasted hours and lost money.
But I was not freaking out. Something was telling me it was going to be okay. I don’t have a logical explanation for that. I just felt it.
Naming His Daughter “Baby” [01:10:00]
Sam: Tell the baby-naming story.
Jack: When you’re at the hospital after birth, they tell you that you have to pick a name before you leave so they can put it on the birth certificate. I didn’t like being told to do something with a completely arbitrary deadline. We just went through the most intense experience of our lives and now we have hours to pick a name we’ll use forever?
I researched it. In Hawaii, as long as both parents consent, you can change a baby’s name without going to court at any point within the first twelve months. So we just named her “Baby” on the birth certificate.
A week later, the Department of Health called to confirm the name. The guy said, “Just to confirm — Baby. The name of your baby is Baby.” I said yes. He said, “Actually, I’ve worked here ten years and a couple other people have done this.”
Then when she was about a year old, we did a naming ceremony. We put several names on the floor and let her crawl toward them and pick her name. Two reasons: it meant she’d always have an interesting story — “I picked my own name.” And we got to know her first before picking something permanent.
Sam: This is so you. You also had someone remotely watch her on a baby monitor in real time to avoid being woken up unnecessarily.
Jack: The “digital night nanny.” Jonathan Swanson, the founder of Thumbtack, told me about this concept. I have a virtual assistant in India who watches the baby cam all night. His instructions: if she wakes up and cries, start a timer. If she cries for less than seven minutes and goes back to sleep, do nothing. If she cries for more than seven minutes, call me.
She’s now two years and three months. We get woken up maybe once every two months. The VA works 365 days a year — I genuinely don’t know what he does on holidays. He probably has the baby monitor on loudspeaker with his family.
Unschooling [01:22:00]
Jack: I read a book called “Don’t Tell Me I Can’t” — written by a teenager who was unschooled. Not homeschooled — unschooled. There’s no curriculum. The kid learns whatever they want to learn whenever it’s useful to them.
This kid grew up poor, father was a disabled veteran. The local school was terrible. They started homeschooling, which still tries to replicate the school curriculum at home. Then his father told him one day, basically: figure it out yourself. He started watching Warren Buffett interviews and then spiraled from there. By 13 he was managing hundreds of acres of land and had flipped a house. He actually loaned money to his parents.
When he was twelve, some kids from school asked him what he was learning. He said he’d been looking into how rich people use pass-through LLCs and C Corps for tax purposes. The school kids had no idea what he was talking about. They were memorizing the planets.
I think exams ruin the curiosity of learning. You associate learning with boredom, with being forced. Self-driven learning is the opposite. I’m not going to send my daughter to school.
Shaan: What if she just wants to sit around and doesn’t have that drive?
Jack: Fair concern. I’m planning to create something myself — bring kids together, let them pick topics, and ping actual experts to come teach them. I think if a ten-year-old emailed me and said “I want to learn business, would you come talk to my class?” I’d do it. That’s more interesting than a standardized curriculum.
Sam: What if she wants to be a doctor?
Jack: Then I guess we hire tutors and she learns the material faster to make up for lost time. I don’t know. I’m figuring it out.
Shaan: The kid in the book — what happened to him?
Jack: He drowned and died right after the book was published. Pretty devastating ending. But the book is short — two to three hours — and genuinely challenges your assumptions about education.
Products and What’s Next [01:30:00]
Shaan: You’ve always been a product obsessive. What’s on your recommended list right now?
Jack: Buckwheat pillow. You can adjust how much buckwheat is in it. The reason it’s great for neck pain: a normal rectangle pillow puts your head at a slightly wrong angle. With buckwheat, you pull the filling to one end so it gives more support to your neck while your head rests lower. You’re completely flat. No crinking.
Our friend Nick Gray ships his buckwheat pillow to every hotel he stays at in advance. If he’s staying somewhere for more than four days, he reportedly ships his mattress too.
Sam: What’s the shilajit situation?
Jack: I had a closet once that probably had $30,000 of supplements in it. I would try something and then sort of forget whether it was working. The only thing I consistently found actually did something remarkable was shilajit — this black tar extracted from Himalayan rock. Looks like heroin in a Ziploc bag. It genuinely gives me something I can feel. I can’t explain it. Everything else in the closet — mostly didn’t feel anything.
Sam: Jack, I call you the most interesting man in the world. The reason you’re interesting is because you’re interested — at great depth, in a huge variety of things.
Jack: Thanks for having me again. I genuinely only listen to this podcast in the car. I don’t listen to anything else.