SaaS Interviews with CEOs, Startups, Founders
How YoShirt App Went from $0-$1m Fast with Ben Williamson of YoShirt Episode 23
01 Mar 2016
Chapter 1: What is the main topic discussed in this episode?
This is The Top, where I interview entrepreneurs who are number one or number two in their industry in terms of revenue or customer base. You'll learn how much revenue they're making, what their marketing funnel looks like, and how many customers they have. I'm now at $20,000 per top. Five and six million. He is hell-bent on global domination. We just broke our 100,000 unit sold mark.
And I'm your host, Nathan Latka. In the last episode, number 22, you heard from Jamie Turner, who went from freelance college speaking to charging 100,000 bucks a year in brand new speaking fees. Okay, our guest today is Ben Williamson. Now, Ben worked under Steve Jobs at Apple for almost 10 years and helped craft Apple's retail strategy.
He's since founded YoShirt, where he's growing the company super fast and landed funding from KPCB, a leading VC firm in the whole world, quite honestly. The dude also knows how to save the lives of 15 men at 5 a.m. in the morning as ocean waves threaten to smash a sailboat along a cliff. in the Catalina Islands. We'll get to that in a second. But Ben, are you ready to take us to the top?
I'm ready, Nathan. Dude, awesome. So first, people are wondering, what? This dude worked, you know, he saw Steve Jobs in action. Tell us about that. What did you do at Apple?
So I was really fortunate at Apple. I was there for nearly a decade, actually over that all in, and then got different key points of exposure. So I worked in retail during the kind of rapid retail growth and was a lead business consultant there and got to see the strategy and really see... What happened when Apple went out to the front lines and decided they wanted to own this experience?
I remember when we took out the Wall Street Journal ad talking about how we wanted to move the dial and we wanted it to get to the point where when you bought an Apple product, people didn't think you were crazy. And at the time, Gateway Country was happening. There was all kinds of negative press about what Apple was doing. And it was a very different time. It was a very different company.
As we grew and as we scaled and actually demonstrated that we could make a meaningful move in the dial and actually take back market share, things obviously changed a lot. But I was fortunate to work in hardware engineering. When Doug Fields was heading up the organization, he created a little thing called the Segway, you may remember.
And then was also a senior software engineer for a couple of years and then left after that. So I got to kind of get the full 360 and CE experience. what made Apple unique and what made Apple successful from a lot of different angles and was fortunate to be able to take that knowledge into what I'm doing now.
So I remember when we met, I think it was at a New York mastermind and we got to spend some time. I'd kind of watched you throughout the night and I would watch you
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Chapter 2: How did Ben Williamson's experience at Apple shape his entrepreneurial journey?
So let's just, you know, well, you told me, I think, look, what surprised me a lot was how you said you watched Steve create SWAT teams for like groundbreaking products. So help me understand, like maybe tell a story about when you saw Steve do that.
It was, you know, an interesting thing about Steve that I don't think a lot of people recognize is that he was a visionary leader. You know, he was a lot of things.
And one thing that people don't necessarily understand is his ability to know exactly what you needed to achieve your very best and his ability to intuit whether or not you were capable of it and you just needed a kick in the ass or you were capable of it and you just needed some help.
approaching the problem from a different perspective whatever it was he you know I kind of observed him his impact really more than working directly with him but just his ability to make sure that the best people were in the right room headed in the right direction and also knowing that
And helping you believe that you could do 20 times more than you thought you were capable of and showing you that it could be done. If you look at a lot of the products that are early on in Apple's history, it was only a couple of people working on it. If you look at the original iTunes application, that was two guys.
And when you think about two people creating an entire application, it just boggles the mind. It's completely different in the way Apple was run back then. It was completely different than anything else out there that a typical software project would have 40 or 50 people on it, four or five project managers, lots of different releases and milestones.
And at Apple, it was just a couple of guys grinding really hard, making it happen in isolation and secrecy until the covers came off and the curtain lifted and The entire world was waiting to rush into the vacuum and see what they traded next.
And Ben, what would Steve say to say these two people working on iTunes when these two maybe developers said, Steve, there's no way we're going to get this released on June 1st?
Well, he would say, you're going to get it released by June 1st. You're no longer going to be here. People didn't say no to Steve often. There was one product I worked on that was a black project. I'm not going to say exactly what it was, but something changed. Frequently, people would work on projects for a really long time. And Steve didn't mention it on stage at the keynote.
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