Learn From Entrepreneur Jack Smith, Founder of Two $100 Million Businesses

Serial entrepreneur Jack Smith shares his advice for aspiring founders and his personal take on startups today.

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Every month, Ambassadors of The Hustle get to quiz superstar entrepreneurs about their successes and failures. Serial entrepreneur and startup advisor Jack Smith (26) takes the mic for February’s conversation.

Learn From Entrepreneur Jack Smith, Founder of Two $100 Million Businesses

Jack is famously known for his “LinkedIn Hack” that helped him raise $120,000 in seed funding for Vungle, his first startup. Since then, Vungle has raised over $25 million from investors and now has hundreds of employees and offices around the globe.

After leaving Vungle in 2013, Jack started advising a few different startups like Survios, Coin, and OnFleet. Four out of the five companies that Jack Smith was involved with are now worth over $100 million… all before he was 25-years-old.

Here’s what we learned in the Q&A with Jack. Answers have been edited for clarity.

Why do you do what you do? Do you have an internal motivation or do you make businesses because you’re good at it and it pays the bills?Vanessa Mitchell

Jack Smith: I don’t think that starting a startup is a good path if your objective is just to get rich as the odds aren’t great. You’d probably be better off just being a banker/trader. The truth is that I actually really don’t like money or the concept of money.

I started startups because I wanted to be independent from a young age and didn’t do good at working for other people.

Now I’m helping some different startups, as I just like helping people.

What was it like going from managing a few people on your team to 20 people?Tam Pham

Jack: As the team grew to over 20 people, I really sucked at managing.

After I left Vungle I spoke to some of the people that I’d worked closely with and asked them for feedback as to how I could have improved. The main advice they gave me is that I micro-managed too much towards the end. They said, “If you’re hiring people, you’ve got to trust them to do work without micromanaging them.”

The best CEO founders that I’ve seen are able to quickly scale themselves and how they work away from doing, towards just coaching others, as the company grows.

What has been your biggest challenge through this journey of yours so far?Sid Thatham

Jack: When I was starting Vungle in England, we had a really tough time fundraising and just keeping the company alive. At one point I had to let go of all my employees. It was a tough situation to go through.

What’s one of your favorite companies right now that not many people know about? Why do you like them?John Havel

Jack: I was talking to a founder the other day and he has plans to run electric trains on the existing Caltrain tracks; and the trains would have WiFi, be more reliable, etc.

Apparently if a private company wants to run trains on the existing Caltrain public infrastructure, they have to be allowed.

It seemed pretty genius, as I was really surprised arriving in SF how much the public transport sucks for the “tech center of the world” – having diesel trains, etc.

How does someone stay in (or opened) to ideas that become $100 million projects?Frank Schwarz

Jack: I like this article.

The main crux is that you don’t have to think of a huge hundred million dollar idea up front. Just start by solving a small problem, that is a big problem, and you can expand your ideas from there.

The key is making sure that initially you’re solving one BIG problem for your customer. Originally I was building stuff that just cured problems they didn’t really care about.

Talk to me about Coin. Those guys had a great idea and totally botched the execution. I know, I am a Coin cardholder. What are some of the behind-the-scenes lessons future product makers can take away from this flop?Jorge Alejandro Leal

Jack: It’s a fair question. I wouldn’t define it as a ‘flop’ personally, as I originally met the founder when he was just at idea stage. So actually bringing a real product to life is somewhat of a success to me. They also sold $20 million of units last year. It is very popular.

But yes, I have a Coin as well, and it doesn’t work everywhere 100% of the time, which is embarrassing and invalidates the core value that it adds (as you need to carry a backup card).

The main thing that other hardware projects might want to do differently is under promise, over deliver. You don’t want to promise too much. Coin had challenges as their launch video was so good, that they had the most pre-orders of a product of all time. But if they’d sold a lot less, it would have been much easier for them to produce without production challenges that come with making tens of thousands of units.

The challenge for hardware startups is that VCs don’t want to give you any money until you can show some sort of pre-sales/interest. But you don’t want to get too many pre-sales, as then you have a more difficult challenge keeping your promise.

What is your view about creating content specifically targeted to another part of the world that you are not physically present in? How would you overcome initial growth of audience since they are not in your primary social circle?Željko Crnjaković

Jack: One example would be a VC fund called Ludlow Ventures. They’re based in Detroit, away from all the startups, but they put out content that startup people find interesting.

Johnathan & Brett work at Ludlow Ventures. They carpool to work every day & started recording their in-car conversations amongst themselves & other entrepreneurs/VCs. Upcoming episodes feature calls with: Eric Ries, Jason Calacanis, & more.

Do you think it’s better to wait for building the perfect team for your startup idea, or just get a couple of talented friends together (even if they don’t have complementary skill sets) and just try to start something?Aman Agarwal

Jack: If you try and get the ‘perfect team’ on paper, those might not be people that you have a strong relationship with, so it might fall apart anyway. It may be better to start with closer friends, as hopefully your strong relationships will pull you through.

I read about the LinkedIn hack, it was pretty clever. Any other digital marketing related tactics you’ve used since?Craig J. Mount

Jack: I also had one for hiring an office manager.

I didn’t have too many other big needs beyond that. Today it’s more important for me to reach people through networking, than pulling stunts (like I had to when I didn’t have a network).

How do you stay focused?Manish Bhattacharya

Jack: I’m not productive or focused. I actually think there are some benefits in having a short attention span, as you can jump on new opportunities when they come up.

I am not a pharmacist and wouldn’t want to prescribe anything. But if I am looking to do a specific project – like make a presentation, or write something; then modafinil/modvigil (a drug generally prescribed for people working night shifts) helps me focus massively.

What advice do you really wish you had received (and needed) before you started your journey in startups?Aman Agarwal

Jack: That as the company gets bigger, you need to stop doing everything yourself and start to trust other people to do the work. And coach them how to do it.

What’s something you’ve learned in the past year that has shocked you?Sam Parr

Jack: I visited Chile and learned that the government is investing a lot of money into startups there; and that with the ‘Startup Chile’ program, a startup can hang out there for a few months and get $40k-$120k for 0% equity. Pretty good deal if you don’t care where you’re based.

I am a marketing guy and want to work on Augmented Reality because I know it’s gonna be BIG. I’m in India, and currently learn programming in my spare time. What advice would you give me? I’m thinking of doing a masters degree in a related field, or even of getting a job as a developer…Aman Agarwal

Jack: I’m not sure how much getting a master’s degree would help you, in terms of I’m not sure how valuable the skillset would be. But maybe the best thing that could come out of it would be that you’d meet other like-minded people.

Probably the best thing for you to do would be to hang out with people who are interested in the same stuff. As then you’ll come up with the best project ideas by brainstorming; and maybe one of them might be a developer.

How do you manage to keep yourself constantly motivated while working on something? After I get a (personal) project idea, I tend to lose motivation while implementing it. How do I sustain that momentum of excitement? Akshay Kashyap

Jack: I suffer from this problem a lot as well. I think that the key is to evaluate before you set out on a project, how motivated you actually are to get it done. As with every project, they’ll be ups and downs.

A key idea is probably saying NO before starting out. So that you only focus on what you actually really care about completing.

Have you had a mentor and do you hope to mentor others?Sid Thatham

I haven’t had one set mentor throughout the past few years. But certain people have definitely been available to me to given great advice. The benefit of Silicon Valley is that people are generally very open to helping one another.

Yes, in my day-to-day life, I try to help a lot of people; I wouldn’t say that I’m a “mentor” to any specific person at the moment, as I think that I don’t necessarily have a lot more experience than too many people yet (still young) and the term would suggest to me that I’d have one person who I invest a huge amount of time helping. Instead, I try and help many different people.

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