Category Archives: Entrepreneurs in Focus

Entrepreneur in Focus: Jake Nickell

For this round of Entrepreneur in Focus I was ready and willing to write about one of my favorite hip and fun Chicago businesses, threadless, but I didn’t have to. So many people love theadless that my job was already done for me. In fact, I’ve probably had more trouble choosing what awesome video to show you that best portrays this plugged-in, Generation Y company, than writing a blog post. But let me indulge in a short who-is-threadless-intro. 

Who Is threadless?

Threadless is a community-centered online apparel store run by skinnyCorp of Chicago, Illinois. Co-founders Jake Nickell and Jacob DeHart started the company in 2000 with $1,000 in seed money after entering an Internet t-shirt design contest. How does it work? Members and artists of the threadless community submit t-shirt designs online and are open to the public vote on. A small percentage of submitted designs are selected for printing and sold through an online store. Creators of the winning designs receive a prize of cash and store credit. It’s a company the relies heavily on crowdsourcing and web 2.0 to connect to the public, and it’s this open connection and two-way communication that laid the foundation for this company’s success.

This is a great documentary that explains the history of the company.

And in case you can’t watch this video at the moment, here’s a great blog post that Jake Nickell wrote about the history of his company. You can find the post on the threadless blog, here.
The History of threadless.“Hi everyone! [I’ve been] inspired to recap the non-stop insanitythat has been running Threadless since Jacob and I officially started it in November of 2000.

2000-2002 – Threadless, The Hobby. Jacob and I met on an online design forum called Dreamless (it doesn’t exist anymore) that was run by Joshua Davis. There was a tee shirt design competition that took place on a thread on Dreamless to design the official tee for an event to take place in London. Jacob and I and about 100 other people all entered and I actually ended up winning it with the design below. (It’s a crappy design, I know, but it would make sense if you were a member of Dreamless b/c that’s what the forum looked like)

So then Jacob and I started talking online about how awesome it was to participate in the competition. Dreamless was all about art and design and a lot of artists on there had ‘battles’ and shared/critiqued their work with each other. It was all around a very creative environment for hobbyists and professionals alike to unleash some creativity in their free time. We thought Threadless would be a fun project that would ‘give back’ to the community by actually creating goods out of the work created by these artists. We started it as a hobby, just a way to enhance the Dreamless community.

We held the first design competition directly on Dreamless. We started a thread on there asking people to make tee shirt designs and stated that we would print the winning designs, put them up for sale and use the profits to hold another competition and print more winning designs.

Jacob and I each invested $500, spent $200 of it on a lawyer to start skinnyCorp as a Sole Proprietorship under my name with the intention of doing web development work as well and the other $800 was spent on printing 2 dozen of 5 different designs submitted on the Dreamless thread that we liked. For the first few rounds, the winning designers received a few free copies of their winning tee and that was it. By 2002 though, winning designers also received $100 cash.

For the next TWO YEARS, Jacob and I worked full time jobs WHILE going to college AND running Threadless. For the 1st year, we actually got our tee shirt printer to ship our orders for us. The 2nd year, We stocked all the tees in my apartment meeting once a week to package all of that week’s orders and then ship them out on our lunch break the following day. Shondi was already living with me at the time and she also helped package orders from the very beginning!

For those first two years, every dime we earned from selling tees just went right back into printing more of them.

2003-2004 – Threadless Gets ‘Real.’ Eventually Threadless snowballed to the point that Jacob and I needed to decide whether we should quit our jobs and work on it full time or stop doing it. I quit my job and set up an office right away, and Jacob followed a few months later. We rented about 900 sq ft and shared it with Chuck Forman of setpixel (who now runs i’m in like with you.) We converted skinnyCorp into an S Corp, finally started paying ourselves, hired our first employee (Good ‘ol Craig Shimala) and made a go of it!

I was still in college when I made this decision and made a last ditch effort to finish up quickly by submitting a proposal to my Dean to let me test out of my remaining classes. I ended up getting credit for 7 classes I hadn’t yet took but still had 3 to go. It became too stressful to continue to go to school while beginning to run my business full time and manage new employees so I dropped out.

At this point, even though Threadless was doing OK, it wasn’t really enough to pay the bills and our main focus was our web development business. We basically used Threadless as proof that we knew how to build e-commerce websites. Craig handled the day-to-day order fulfillment and customer service while Jacob and I worked on programming boring websites and working on Threadless whenever we had a free moment.

This is also around the time Jeffrey (iFDL) started working with us. We were basically partnering with him to design the websites that we were programming and ended up hiring him when we discovered just how well we worked together.

By the end of 2004 we outgrew our space and had to move. Oh, and we were paying winning designers a bit more with $400 cash and a $100 gift certificate.

A special about Threadless on MSNBC

2004-2006 – The Big Growth Spurt. We moved from our 900 sq ft shared office space into a 3,700 sq ft space. We basically just sat in the corner of it when we first moved in and wondered, “WTF, why do we need this much space!?” Well, by the next year we ended up taking up the rest of the 1st floor, expanding to about 8,000 sq ft. And by October, 2006 we moved again into our current 25,000 sq ft main facility.

During these years I watched Threadless grow by leaps and bounds. In number of employees, warehouse space, tees being sold, designs being chosen per week, prizes being awarded to designers, etc, etc. Things were growing a lot in the first few years too, but going from 2 to 6 employees is a lot easier to take in than from 6 to 18 employees.

By the beginning of 2006 we decided we would need some help maintaining the growth. So, by late 2006 we took on an investor (Insight Venture Partners) that could help us figure out our fulfillment logistics and such. They’ve been a huge help so far. It’s been a huge relief to me having some help in that area because I’m much more interested in the creative, fun side of the business. It’s nice to have someone with expertise that is invested in the business to help us figure out all the boring stuff.

2007 and beyond – Now & Later (Too Legit to Quit). So far 2007 has been pretty rockin’ … it’s always fun putting together our sales, it seems like every time we have one we out-do the previous one. We already added another 10,000 sq ft for pallet storage. The prize for a winning design is up to $2,000 in cash and prizes and will only get bigger.

Right now we’re continuing to have fun rolling with the punches and opportunities that Threadless brings. It’s always been about just doing what feels right and what we think would be cool to do. So right now, that consists of creating our very own private label tee shirt, setting up crazy retail stores starting in Chicago (we like to call them community centers), trying to do more for our international customers by getting shipping time and costs down and some other fun stuff, furthering Threadless Kids and a bunch of other random things.

Threadless is such a huge part of my life. Everyone in my condo building I’m sitting in here calls me the t-shirt king, it’s hard to put on anything but a Threadless tee in the morning, I get to work with most of my best friends, I see new amazing artwork every day, communicate with people all around the world, am faced with new challenges every day and here I am blogging about it at 2 in the morning on a Tuesday o_O.

I love every minute of it 🙂


10 Years of Awesome!!!


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Entrepreneur in Focus: Geoffrey Canada

In the spirit of expanding our blog to spotlight a successful entrepreneur, it’s fitting that our first Entrepreneur in Focus be one who has been the subject of our previous blog posts on education reform. His name is Geoffry Canada. As the CEO of the Harlem Children’s Zone he’s helped to revolutionize the way a nonprofit enterprise can “change the trajectory of a poor child’s future in an inner-city neighborhood.”


Geoffry Canada was raised by his mother, Mary,  in Harlem, New York.  Finances were tight. In the early years Mary struggled to support her four sons, and as a result Canada’s early life was marked by poverty. She loved and cared for her boys, working hard to raise them with values.  Limiting their television intake, tutoring them herself and taking them to civil rights rallies, she instilled in them the importance of education and concepts of social equality.  Living in a poor, unsafe neighborhood Canada had to learn street smarts to stay safe.

In his teens he went to live with his grandparents in Freeport, Long Island where he excelled in school and won a scholarship. He continued his education at Bowdoin College where he earned a Bachelor of Arts degree in psychology and sociology in 1974.  He also holds a Master’s degree in education from the Harvard Graduate School of Education.


After graduation Canada joined the faculty of Robert White School, an alternative school for troubled youth in Boston, Massachusettes. His ability reaching these students, especially the most violent ones, was a reason for his quick rise to the director position of Robert White.

In 1983 he returned to Harlem determined to make a difference in his old neighborhood. He wanted to help others succeed as he had. He got a job working for the Rheedlen Centers for Children and Families as a program director in the Truancy Prevention Program, and by 1990 had risen to President of the organization. Canada was unsatisfied with the scope of Rheedlen, and he began to make changes. The Rheedlen Center was renamed the Harlem Children’s Zone and Canada shifted the entire makeup of the organization.


In an interview for the documentary film, Waiting for Superman, Geoffry Canada explains that he decided to go study what was wrong with the public education system so he “could fix it.” After earning a master’s degree from Harvard, he figured this would take “two, maybe three years.” That was over  35 years ago. NPR’s This American Life did a segment on him for their “Going Big” show. Going big was what Canada realized needed to be done to reform education.

The idea came to him when he and his wife had a son. As the narrator on Going Big” explains, Canada was in his 40’s and things had changed for him. “He was no longer trying to make ends meet. He was now a well-educated, upper middle class guy living in a big home in the suburbs surrounded by trees and lawns and golf courses.”  As a dad he found out there was a ton of new research on the benefits of stimulating your child’s brain at a young age, and it surprised him that everyone in the suburbs seemed to know about it. “They were obsessed with preparing their children,” he explains. People in the suburbs were buying up every Baby Einstein product  or other brain building toys for kids in sight. Canada said he felt “overwhelmed” by all this new information and wondered how the parents they were working with in his organization were fairing in the “parenting revolution.” He asked his staff to canvass the neighborhood and what they found was there was nothing. Abolutely no one was teaching anything – no best practices, no parental education, nothing – for moms and dads of 0-3 year olds. It dawned on him that places like Harlem “are often left out of the science of developmental education.”

At the same time Canada began rethinking his approach to social work. After so many years of frustration saving one child and having 10 more slip through the cracks he wondered if there was a tipping point, a point at which the the entire culture, the cycle of teen pregnancy and dropping out of high school could be altered. Could he reach 40 or 50% of these kids? He went to his board with these thoughts and the conclusion: we’ve been going about this the wrong way.

It was this revelation that led to the complete re-thinking of how they were approaching urban poverty and education reform. The two were intertwined. Middle class and upper middle class families had access to this information and talked about it openly. It completely passed over lower-income families. Kids in middle to upper middle class families have opportunities to continue to grow and develop after school with programs, clubs, sports and more. Kids from lower-income families are too often left unsupervised, because their parents, or parent, are working. Single parents in the neighborhood had little access, or knowledge, of support systems. What Harlem Children’s zone aimed to do was provide a quality education for the children of Harlem as well as design a support network that is “designed to mimic the often-invisible cocoon of support and nurturance that follows middle class and upper middle class kids through their childhood” until they graduate college.


Quoting from the HCZ Project web page: “The HCZ Project began as a one-block pilot in the 1990s, then following a 10-year business plan, it expanded to 24 blocks and then 60 blocks. The goal is to serve 15,000 children and 7,000 adults by 2011. The budget for the HCZ Project for fiscal year 2009 is over $40 million, costing an average of $3,500 per child.”

The ambitious Harlem Children’s Zone Project has expanded the comprehensive system of programs to nearly 100 blocks of Central Harlem and aims to keep children on track through and beyond college, as former students enter the job market. So, what programs and services are included in HCZ?

  • Baby College, a series of workshops for parents of children ages 0-3
  • Gems, an all-day pre-kindergarten program
  • Harlem Peacemakers, reducing violence through negotiation skills and self defense classes
  • Promise Academy, extended-day charter schools from kinder to 12th grade
  • TRUCE Arts & Media, fostering career readiness through media literacy and artistic ability
  • Employment & Technology, teaching computer and job-related skills to teens and adults
  • College Success, an office that supports HCZ graduates throughout the college admission experience and during their college education
  • Community Pride, organizes tenant and block associations
  • Family Support, provides crisis intervention services, advocacy, groups on parenting and anger management training
  • Asthma & Obesity Initiatives, educating families and providing management counciling

And there are many more. Read more about these programs and their success. This is significant because HCZ is now helping $1,200 students, 90% of which go on to attend college. The odds are in favor of college grads for breaking that cycle of poverty.


Geoffry Canada’s Harlem Children’s Zone has been extraordinarily inspirational. president Obama launching promise neighborhoods program, 20 cities across US to mimic HCZ. Read more about promis neighborhoods here.

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Filed under Education Reform, Entrepreneurs in Focus, Young Entrepreneurs Program