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Jim interviews Nate Cooper, a former Apple employee that is now teaching technology in New York, and his use of kickstarter to fund his webcomic, skillshare and meetup classes, coworking spaces, and the startup bus.

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The following are some excerpts from my awesome interview with Nate Cooper. Check out the entire podcast to hear the whole interview.

Nate’s background
After moving to New York City from California without a job, this ‘independent academic’ worked his way up from being a seasonal hire at Apple, to full time employee to event trainer. Jim asks what is it really like to work at Apple, and what was his greatest experience there. Nate talks about the fact that since the Apple brand can attract such a quality, creative workforce, the type of people he got to work with were really amazing. Many went on to some really high profile jobs.

The conversation moves to how Nate made the transition from working the floor at Apple to running their events and training, and the reason he decided to leave.

Nate credit’s meetup.com as the online tool that inspired him to take the next step in his career. Because he was excited about teaching, here was a way for anyone to get online and easily organize people into classes around a given topic.


Jim wonders, “Are we spoiled in New York City?” The stats would seem to indicate so. A search for internet and technology meetup groups numbers 276 in the New York area, vs just 14 in Phoenix. Even major cities like Boston (47) and Chicago (55) have fewer than a quarter of the number of available groups. Ironically, it was our mutual friend John Murch (from Episode 146) — who I met at a meetup — who introduced us.

Our connection worked as successful ones often do… both parties benefitted.

– Nate contacted me because he was looking to turn his course into a book. As he spoke to his network about this, my name came up in 2 different conversations based on my experience with technology and publishing.
– Meanwhile, after getting laid off just days before, I was firing “what do I do now” questions at Nate, since he had been working independently for almost a year.

Freelance advice
The one thing Nate kept hearing over and over as advice for those trying to go freelance… You just have to do it.

In his first year, he has seen projects take off and others fail, but he has learned to adapt. A site like Meetup makes it easy to try something out and see how it goes. The downside of too many meet ups might be that there is TOO much going on for people to focus.

Key advice
I realized that Nate had hit on the very thing that this new direction of my blog was going to be about.

Between Wired and Apple, we were at some pretty great companies… names that people would die to work for. Living and working independently sounded like a dream, right? Everything you hear about working remotely, hanging out at home, and controlling your own hours. The only little problem is, how do you make money? We bonded because we were both teachers at heart with the same problems…

– Meetup and Skillshare were great, but how do you best leverage them?
– How do you find the sweet spot when charging for a class?
– How do you market it to get the word out?

Reboot Workshop
We start to talk about why and how do we decided on the Reboot Conference. Advice he got was to learn by doing, so we figured maybe we just get a bunch of people together that we like and see how they do it. We handpicked things like accounting, storytelling, social good, got all these people together, and just went for it. See the next episode for a full analysis.

Startup bus
Our thoughts then turn to the Startup bus. Like SXSW, some people are like hmmmm, what’s that? While others are speechless with excitement.

For those not in the know Startup Bus is a “hackathon” on a bus. It’s a 72 hour trip from various cities (NY, DC, Boston, etc) to the SXSW Interactive conference in Austin, TX.

During the trip, the riders put together a company, completing as best they can by the time they pull into Texas. What was surprising was that it wasn’t just a bunch of website geeks, but actually hackers, designers, programmers, and even [gasp] business people!

Startup Bus

Nate’s flagship course is “website bootcamp for creative professionals,” a course that is not really HTML, not really servers, but weaves in and out of the themes. There are a lot of people that need help and know certain terminology, but don’t know what other things mean or how they work, like FTP or whatnot.

His Issue?
The class has been successful here in New York, but he had no way to reach people outside of the city.

He had already been writing a book, and since he wanted to get it across to a non-technical audience, he had a seminal moment: make it into a comic book. He teamed with talented illustrator Kim Gee and is funding the project through Kickstarter as a way to teach a technical subject to a broader audience.

What is Kickstarter?
It’s a new social media way to raise money, sort of a grassroots way to fund a passion project. If you don’t need ton of venture capital, just some help starting, pitch your project to the crowd and they will tell you if it is good or not.

Key takeaway and advice
In a microcosm, Nate had illustrated the exact steps that someone can take to lead a better career lifestyle:
1) Experiment with your core skills. Nate knew he wanted to be a teacher and was good at it, so he used free services like Skillshare and Meetup to rapidly test his ideas.
2) By doing so, he knew what was successful and what wasn’t within days and weeks, not years.
3) Once he knew what resonated, he was able to hone it with each successive class
4) Finally, once he had a great product in person, he could then reach people outside New York by creating a digital product

The other huge piece of advice was building relationships. We know someone at almost every co-working space in the city, yet have remained “workplace agnostic” with our business ventures. Coworking functions as the modern day coffee shop – with the difference being that people go there because they WANT to run into others.

Jim says, in a major corporation, you’ve got your collection of management, low level employees, slackers, new people, and old farts.

But in a coworking space, every single person is outgoing and exciting and working on 17 projects at once. Amazing connections continually happen.

Wrapping up, we discuss:
– As a newbie, what is Nate expecting at SXSW and what are his goals?
– What would he do other than his current profession?
– How do you maintain a worklife alance?
– What websites do you visit every day?
Answer: Reddit and Jason Kottke
– What is the first thing he thinks about when he wakes up in the morning?
Hint – his phone is his alarm clock
– What book he puts out to impress visitors
Answer: Book he is reading right now: Where do good ideas come from? by Steven Johnson
– What advice do you have for those looking to start own company, or make the transition

Find out more about Nate at NateCooper.co and @natecooper

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