Jack Smith is a recovering entrepreneur, now building “rehab for technology addiction” with Silent Break. He co-founded Vungle, which was a performance marketing platform specializing in in-app video advertisements for mobile devices. It sold to Blackstone for close to $800M in 2019. Jack was kind enough to spend some time to share his insights with the HackerNoon community. Pictured above at a recent silent retreat.

David Smooke: On Andrew Wilkinson’s new podcast, Sam Parr described you as someone worth learning about: “He started a company when he was 22 called Vungle and he sold it for $800 million when he was 28. He made a lot of money. And he still dresses like a bum. He's the only guy who I've ever met who made a nice amount of money through, self made, and was like this is enough, I don't need anymore. So he spends all of his time writing prisoners. His thing that he loves is making sure when you get out of prison that you've got a skillset so you don't go back to prison. He spends most of his days writing prisoners. He’s got a charity (Prison Math Project) where he buys them any type of book that they want, a lot of math books, things like that. He also is very logical where he doesn't get caught up in certain things, almost like Charlie Munger, where they're like borderline autistic, where they don't experience certain human emotions in a good way…” A lot to unpack there. But firstly, let’s fact check, do you dress like a bum? What is your daily wear? And what is the most valuable piece of clothing you own?

You started Vungle in London, and moved to San Francisco to join the AngelPad incubator (story told to Valley Girl TV) in 2011. I also moved to San Francisco around that time. And have also since moved elsewhere (Colorado ftw!). I used to think and still kinda do think that San Francisco is the best place for young professionals to start something new. Do you think Vungle would have grown to such a sizable company/exit if the company HQ was elsewhere? Is the Bay Area still the place to start a company?

1/ No, I don’t think that Vungle would have gotten as big if it had been launched anywhere else. I think that a core part of how Vungle was able to succeed is that we’d tried (and failed) to launch the business in London and had such huge challenges trying to raise funding or making any progress. Then, when we moved to San Francisco, it felt like the streets were paved with gold! Any person that I wanted to meet was a short walk away, and meeting amazing people, they opened their rolodex to me and offered to introduce me to anyone they knew. So many resources were available to us.

2/ Nowadays, things are more remote accessible and I haven’t been in the Bay Area for a few years, so I’m not sure to what degree it still has extreme benefits. I think its value has certainly decreased a lot, but many VC firms are still based there.

If visiting the Bay Area, what is one under the radar experience you recommend to people? Mine is to eat Molinaris.

I like Fish in Sausalito. Nice trip.

Today, in what ways is mobile app user acquisition and app monetization drastically different and remarkably similar than it was during the rise of Vungle?

When we were starting Vungle, the predominant way of monetizing mobile apps and acquiring users was through banner ads. Nowadays Video is much more prevalent. So that’s the main change; also that user data is much more restricted as Apple has clamped down on privacy. But analytics and things that apps and games consider have remained similar.

Re: how marketing works - what do you think startups commonly misunderstand?

I highly recommend this book, “The Burned-Out Blogger's Guide to PR.” I think too many startups give marketing a bad image. It’s fashionable to say “we have spent $0 on marketing!” Instead, they think that they can just be lazy, put out a press release and tech blogs/news will cover them. Marketing can be work and can be approached thoughtfully, which is what we did.

How does being on the board of a public company compare to being on the board of a startup company? On which boards have you made the most notable contributions?

The public company boards that I’ve been a part of were things like SPACs, so I don’t have the true experience of being on a high growth company board. But typically what I see is that public companies are much more about compliance and committees than adding value. For startups, a board can often provide more hands on help, help with recruiting etc. Nowadays, the board I’m most involved with is a charity: The Prison Math Project and there I help develop the technology aspects of the charity.

As someone who’s created and exited a successful startup - it seems like you have beat the capitalism game -  and yet Sam Parr described you as someone who “was like this is enough, I don't need anymore.” What is the role of money in your life today? How does it impact your decision making? Do you advise others to think about money less? Is it even possible to think about money less - won’t capitalism leave us behind?!

Money is a complicated subject. For me, now that I don’t need to worry about rent/accommodation and food, I am good above that I feel like.

I also think that you can think about money without thinking about getting rich. Starting Vungle, I didn’t aspire to get rich, I aspired to build a big company - it just happens that that is judged through the lens of revenue and shareholder value.

So in entrepreneurship, I view myself as a sprinter; it just happens that in the game I chose, how fast you run the 100 meters is the scoreboard of success. But running 0.1 seconds faster than someone else wouldn’t make me feel complete. Similarly getting more money won’t make me ‘complete’, it’s just a scorecard.

You also make angel investments via The Tribe (syndicate details). Last I checked, the point of investing was to make more money. Do you invest to make more money?

I haven’t actively made any startup investments over the past few years. It’s a dopamine rush that I’m trying to move away from. But to answer your question: theoretically it would be to diversify and make money, in reality it’s because of FOMO and dopamine.

I saw your recent tweet about the inherent difficulty in spelling “bureaucracy.” I’ve run into a similar problem learning to pronounce “bureaucracy.” Bureaucracy is a part of society. To the next founder who is starting a business because they must fight back against what they see as unjust bureaucracy, what advice do you have for navigating the existing bureaucracy for the sake of their business?

I think the main lens that I view things through is ‘what is the punishment’ for violating some piece of bureaucracy. Many people in places say something is “illegal”, but when you delve into it, the punishment is a $5 fine. Uber pioneered “ask for forgiveness, not permission”, but nowadays I think that the climate is quite different. I think you need to assess what rules you’re looking at and also think if there’s ways to play within the rules, but achieve what you want.

Did Blackstone approach Vungle or did Vungle approach Blackstone? What were some of the tangible and intangible signs that indicated to you that it was the time to sell and this was the right buyer?

Given the size of the company, doing hundreds of millions a year in revenue; it’s not the stage that Vungle would could email Blackstone or something :) Vungle had a banker for a while exploring a sale and then Blackstone’s fund seemed a strategic fit. At the time the company sold; I was no longer at the company. My cofounder and I would have been interested to keep growing the company; but one thing that’s not super clear is when you take VC funding, the clock often starts ticking for you to generate an exit. So many of Vungle’s investors were putting a lot of pressure and hoping and praying for the company to exit, so they could generate some returns for their investors.

This week, what is the most interesting project you are working on? And how do you decide which projects are worth working on and which projects are not worth working on?

Over the last year, what is something you’ve done that was unexpected fun?

I did the Hoffman Process a few months ago. I did not expect that to be as fun as it was :) They have locations in California and London, I did it in London. It was much more experiential than I had envisaged it would be.

If an entrepreneur is experiencing burnout, what should they do?

Currently: go to Bali Silent Retreat; in the future, visit Silent Break :)

Going to Bali Silent Retreat for ~10 days with a suitcase full of books was extremely healing and energizing for me.

If a stranger on the internet asks for a book to improve their life, what do you recommend?

I like the book The Burned Out Bloggers Guide; it’s structured like a compendium of blog posts. So it gives a glimpse into different thought provoking productivity concepts, so I found it quite a unique book.

Why does prison reform matter to you? And if you could, make the case that it’s one of the most impactful ways to donate money?

I was inspired to learn more about, and to help, the prison system especially in America after viewing the documentary: 13th.

Many people in prison and jails in America are treated like animals. I’ve spoken to some who volunteered in a prison kitchen, serving meat that was labeled as “not for human consumption.”

I was also inspired after volunteering as a mentor with the charity Defy Ventures; there, I saw super built men break down crying, because for the first time in years, someone had gone out of their way to help them and make time for them.

Also, many innocent people end up in prison; they can’t afford a lawyer and get appointed a public lawyer 15 minutes before they’re due to go before a judge. The stories are crazy.

If you could change one thing about how the internet works for everyone, what would it be?

I think that the internet is addictive, like alcohol. I hope that in the future things are not just about gamification and making us even more addicted; but that thoughtful consumption/usage of the internet can continue to evolve.

To learn more About Jack Smith:

• JackSmith.eu
• LinkedIn
• Crunchbase