How to Escape Your Velvet Prison Tech Job — and Work for Yourself.
Michael Kors Director of Innovation quit after 7 years to work for the best company in the world — “my own.”
Eric Mogil rose the ranks at Michael Kors, eventually championing their move into wearables as Director of Digital innovation, spearheading the go-to-market launch of their smartwatch in partnership with Google.
And after 7 years, he did the thing that no one does. He quit. And became a co-founder at a wearable tech company, only to leave it and begin advising early stage startups and venture funds. Check out our top 4 insights from our Modern Independent interview with A.Team member, Eric Mogil.
#1 Velvet prisons are still prisons. Break free.
“After 7 years of driving digital innovation & growth at Michael Kors I got bored. I called it a velvet prison. It was the best job in the world, flying around on private jets — working with global teams, getting to travel, getting mentored by brilliant human beings.
I had never been on a plane. I’d never really traveled at all. So this job got me to see the entire world. I learned everything about social media, digital media, growth, e-commerce, direct to consumer, and more. But it came to a point where I thought, “You’ve built the team, you’ve seen the company grow, and you’ve learned everything you can about a business.” And I think it’s just human nature — if you’re doing anything for seven years, you’d want a change.
So I did the number one thing a millennial shouldn’t do when going to talk to a baby boomer CEO, and I walked into his office. And said, “I think my time here is done.” He asked, “Well, what are you gonna go do?” And I said, “I’m gonna go travel and find myself.” So he’s like, “I’m not gonna let you leave — I’ll give you a sabbatical. Take all the time you need and when you find a job that you think is good enough, you’ll bring it to me. I’ll give your feedback and if I think it’s good enough, you can leave.”
And that’s why it’s a velvet prison. You get paid really well. You get to travel. You get to meet interesting people who want to meet with you because you’re a big fish in a big company. But then you get bored.
I looked at big tech companies like Facebook and Google, I looked at some of the startups I had worked with that’d become middle-sized companies. I looked at a bunch of the agencies because I’d worked with over a hundred agencies — from the big creative ones like RGA, Razorfish and Nitro to small creative shops. And I couldn’t really have found something that was a fit because I had never really taken the time to ask myself, “What do I want to do?” and “What kind of culture and what kind of projects and what kind of work-life balance do I want?”
And that’s why it’s a velvet prison. You get paid really well. You get to travel. You get to meet interesting people who want to meet with you because you’re a big fish in a big company. And it was one of those meetings there I met my next jump. It was a company that shared investors with Michael Kors. They combined fashion and wearable technology in a genius way.
Once I heard the idea, I was obsessed. And they ended up offering me to be their third co-founder, the CMO, and the head of product. And so I finally made the jump to go from a 13,000 person company to a 20-person company.
#2 Become obsessed with your input, not your output.
“You should be obsessed with your inputs, not the outputs. And what I mean by that is you shouldn’t tie yourself to the success of a brand name or a company. Instead, you should tie yourself to the skills that contribute to your collaboration and tie yourself to the kind of team member you are. And that’s because you’re gonna be serving on tons of teams in your life — and if you get obsessed with tying your name to a startup, it’ll create a lot of anxiety because even to the outside world, you rise and fall with your startup.
I think it’s extremely important to be committed to your output, but don’t let it be everything. For example, I made so many mistakes with the company I became co-founder of after Michael Kors — basic mistakes from hardware to early stage startup planning, risk mitigation to roadmapping to engineer optimization.
So long story short was that it was a blessing because even after all that, I wasn’t turned off from startups. I took what I learned from my own failures and helped other companies with their inputs. I ended up working for two VCs and being an operating partner and strategic advisor to both their portfolios of 30+ companies — one in the crypto space, one in the retail tech space. And instead of learning from one company, I got to work with over 50 founders and founding teams on product growth marketing.
I saw them making some of the same mistakes that I was making, so I was able to help them and then I saw some of the challenges in mass that early stage startups create when you’re building something from zero to one hundred. And what you realize is, there’s a pattern of early stage companies — you need a great product, a really clear role definition, a really clear product definition, and a great brand story that gets repeated repeated over and over again.
The other tough situation is you have to get very comfortable with what I said about the inputs and focus on them more than the outputs because from an outside point of view, your parents and your friends won’t understand what the hell you do or be able to measure your success unless you are at a funded company or you’re at a big brand name tech company or brand. They don’t understand what you’re doing and you don’t have a proxy for success.
It’s like an artist, so to speak, painting on their own. They have to get really happy with their inputs and think, “My technique is really good and getting better” rather than “Am I creating the best art everyday?”
And working in freelance means you can’t reach the most beautiful places on earth with a direct flight. Like there’s plenty of stopovers to get to the best places. So if you want to be like everyone else, and take the direct flight, you can go to the major cities. But if you want to go wander lands remote, you’ve got to kind of take a small plane here and a boat or ferry there.
#3 Ego death is a necessary step to finding your own life roadmap
“The most important lesson for startups if not in life, is ego death. When a startup is crashing and burning your ego will not help you or save you from the inevitable. You also learn that there’s wartime CEOs and peace time CEOs. Almost anyone can be a great peacetime founder — money is coming in and the economy is good. And you have the luxury of saying, “If this doesn’t work, I’ll pivot and try something else.
What makes startups that become great and change people’s lives and ultimately make it to their mission and vision, is they have to go through a bunch of hardships. I say it’s like chewing glass and getting punched in the face every day. But you have to be used to investors being concerned and you have to be used to potentially wasting money on development or hardware or the wrong hire — or going the wrong direction to find out on your own.
You learn two things from a post-mortem. The first is what you could have done the first time around like certain activities that can focus your company. And the second is you you learn how to be adaptive — and you also learn to expect, so you’re ready for things that come up in the future. So yeah, avoid individual ego, build a thick skin and habit of self-awareness and reflection; if anything, build a team ego where you are confident in your team and partners to work through any future challenge together.
#4 Find the “get shit done” community.
“I started learning about different business models, hardware manufacturing, brand design, you name it. I’m working and learning from the most talented people you’ve never heard of — people who would never work at a single big company, but have quietly been doing brands or app work or working for the likes of Steve Jobs or Kanye West as a creative director.
I would have never met these people unless I joined the “get shit done entrepreneur and freelancer community” — people always asking, “How do we build shit? And who are the best people doing that?” And I felt like Aquaman reaching Atlantis, and it’s like, “Holy shit, there’s this vibrant world here that’s better than anything I’ve ever seen — like when you get the golden ticket to Wonka’s factory.”
I’ve just found there’s so many people to learn from. And I realized that I actually know nothing and I have so much growing to do in terms of skill and in terms of types of projects I have experience working on and thinking outside of the box. So yeah, I mean, I’ve gone to a place now, where it doesn’t matter what anyone else thinks. What matters is continuing to collaborate with the best creators and minds and missions focused on bringing something cool to life.
Communities like A.Team are amazing because you get to meet people who have a similar drive to be autonomous. There’s Zoom talks, there’s meetups, there’s Slack channels and groups dedicated to interesting people who want to help other people. They want to collaborate with others when it makes sense. There’s hundreds of opportunities to do that — even if the one in front of you doesn’t immediately work out. And so yeah, that’s my biggest piece of advice: join a community — even if you look at the Slack once or twice a day or you join an event once every few weeks.
About A.Team
We’re A.Team, a company founded to empower the most skilled, independent pros in tech — where product managers, designers, developers, data scientists, and marketers can team up to build tech that matters with on their own terms. Sound like it’s for you? Join us! Apply here.
