Here’s what I like about the interviews I’ve been doing over the past few weeks; I’m asking people I find interesting questions I want to hear the answers to. I guess it’s a little self-indulgent, but I think it works and hopefully you guys are enjoying the interviews as much as I am. In the tee world, if there’s anyone that doesn’t need an introduction I think it’s Jake Nickell, he’s one of the founders of design competition giant Threadless, and therefore probably responsible in one way or another for part of your wardrobe.

1. Jake, I’m no businessman, what does a CSO do all day?

Jack Nickell: I’m CSO because I’m not businessman either! A couple years back, I finally hired our CEO, Tom Ryan, to help take over the ‘business’ stuff. Not my specialty and kind of stumbled into becoming a ‘entrepreneur’ after Threadless, my hobby, turned into a business. I took the title CSO (Chief Strategy Officer) because I love working on the community side of Threadless. I thought that since what differentiates ourself (our strategy) is our community – the title made sense. Maybe I should just cut to the chase and call myself Chief Community Collaborator or something. Titles are lame anyway.

What do I do all day? Well – a huge variety of stuff. I work closely with Tom to ensure that all the ‘business’ stuff we do makes sense for our community. I also work a lot on keeping the company innovative – making sure all our employees are empowered to make change and helping them to make their ideas happen. I work on Threadless projects of my own a lot too and still do a fair amount of coding on

2. Am I right in thinking that you live permanently in Colorado now? And if so do you get back to Chicago much and do you miss the buzz of being in Threadless HQ on a regular basis?

Jack Nickell: Yep – in Boulder, CO. I get back every month or so. I do miss it, I miss everyone in Chicago, it was a tough decision. I knew I wanted to live here and raise my family here. I lived in Denver a bit growing up and always loved Colorado. The decision was personal and maybe staying in Chicago would’ve been better for the company but sometimes you gotta make sacrifices to balance your work/personal lives. I absolutely love it out here!

3. Do you ever just wake up and think “I’m the coolest dude on earth”?

Jack Nickell: Haha no! I usually wake up and think “Damnit why can’t my daughter sleep in past 6 just ONCE.” I do have an ongoing quest to be #1 on Google for the search “coolest dude on earth” and I have been there for like 5 years now! Fun.

4. A few years back I almost had an internship with a company in Boulder, so when I was researching the place everything I found said “best place to live in America,” do you agree?

Jack Nickell: Absolutely. Every day I see more about how great this town is. I had no idea before moving here that there was such a strong tech & startup scene. Apparently, we have the most startups per capita here than anywhere else in the US. And I love getting involved with it all. It’s impossible to walk downtown here without seeing someone you know who is doing something amazing. Very inspiring place to be. And that’s not even taking into consideration the terrain… It is so beautiful here, and so many outdoor activities to do.

5. A few years ago I read an interview with someone from Threadless (I think it was either you or Jacob) saying that because of the way the company was growing it wouldn’t need VC investment, and then Insight became a partner of yours, what changed?

Jack Nickell: What really got us thinking about this is that Amazon actually wanted to buy us around this time. Although we knew we didn’t want to do that – it did get us to start thinking about these types of things. We didn’t need investment when we did our deal with Insight. We’ve been highly profitable since our first month when we earned back the $500 we each put in to get started and that’s never changed. There were two main reasons for us to do this. First, it was a way for Jacob and I to sell a minority of our shares to make some money for ourselves for what we built up until then. Second, we needed help (not money) in running the business. It was growing so fast underneath us and we are both college drop outs doing this for fun. We were unable to manage the growth… for example, sometimes it would take us over a month to ship an order out because we were so overwhelmed with orders. What we liked so much about Insight was that they had a team called “Insight On Site” that came in and helped us with our problems. They weren’t just a faceless VC firm.

That’s not all of it, Read the rest of the Jack Nickell interview at hide your arms

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