We can’t believe it. Although it started with a small summer camp in 2009, this week we are celebrating our company’s one-year anniversary. One full year gone by, one full year since we made the jump, one full year since we started 220.

One full year working in the career of our dreams.


We want to thank each and every one of you, our 220 Community, for your instrumental role in the success and growth we experienced in our first year. To the people who encouraged us to go for it, those who doubted us, the old relationships we’ve strengthened and the new ones we’ve made, we cannot thank you enough, as none of this would be possible without you.


We thought it would be fun to share our year in review with our 220 Community.

Below are some things we did not expect to happen, some interesting lessons and takeaways, and what we’ve learned about each other.

We hope you have as much fun reading this post as we had reflecting on and writing about Year One.



August 2015

  • We leave our jobs in finance and healthcare to start our leadership company and become full time Co-Founders of 220 Youth Leadership.
  • The journey of building the 220 website ourselves begins. We never imagined how much time it would actually take, how many changes we would make throughout the year, and how many complete overhauls (three) would be necessary to grow with our company and our message.

September 2015

  • We have our first and worst meeting ever with a prospective customer. It was a pretty warm introduction so we thought we were going to have a friendly and open discussion, but they asked for our pitch and we were taken way off guard. This was an incredible learning opportunity that we were lucky to have early on.

October 2015

  • We get 12 free consultations scheduled with parents for our 1-on-1 Program after just one marketing event! Only two parents showed up to their consultation, and none enrolled in a program.
  • We get our first group program scheduled with an afterschool program in Chicago.

November 2015

  • We get invited to be an exhibitor at a Chicago School Fair, which turns out to be our largest source of clients for the year!
  • We sign up 50 people in two days for our free webinar designed to get families interested in our online program, which ends up having a 3% attendance rate and no program enrollments.
  • We find out we are going to be featured as a reference and resource in a book called Self-Determination in Higher Education, which is about creating a comprehensive culture of self-determination at higher education institutions. The book was published in July 2016!

December 2015

  • We find out we are going to be featured in a second book called Fire Starters, as two of six people throughout that overcame their fears to pursue and live their passions.

January 2016

  • We meet our small business advisor, joined our first board of advisors, and became expert contributors for our first media outlet!
  • We got three families enrolled in our 1-on-1 Program in one day!

February 2016

  • We say no to a revenue opportunity for the first time, based on the program not aligning with our long-term vision.

March 2016

  • We decide as Co-Founders that, because (1) our mission and our programs have a much larger scope than we anticipated, and (2) we have a strong appreciation for culture and love to travel, we will become an international company. Then we have a call that led to an invitation for us to speak at a life skills conference in India.

April 2016

  • We get asked to help start a new community leadership program for middle school students in Indiana.

May 2016

  • We led a workshop at a state-wide afterschool conference for the first time. We met one of our most interested prospective clients ever, but failed to collect her contact information. If you are out there reading this, we’d still love to work with you!

June 2016

  • We met with Stedman Graham to talk about working together on his Building Community Learning Initiative.

July 2016

  • We were featured on our first magazine cover!

August 2016

  • We signed our first comprehensive, yearlong group leadership program!



  • However long you think a task or project will take, multiply it by three.
  • Telling a story is the most powerful way to get your message across and connect with your community (thanks, Shannon!).
  • Thinking big + appreciating small wins = Success
  • Gratitude practiced regularly is one of the most invaluable skills a person can learn.
  • Continuous learning has helped us as much as anything else this year.
  • Never underestimate what investing in yourself can do for your goals and your performance.
  • The balance between open-mindedness and sticking to your guns is absolutely critical to productive progress.
  • There's incredible value in getting away (walks, working out, clocking out) from work
  • The more you fail and step out of your comfort zone, the closer you are to success. All of our failures have been instrumental to the success we’ve experienced in our first year.



  • Matthew must believe he is the Flash, because he vastly underestimates the time it takes to complete any task.
  • Joseph doesn’t ever believe I know what time zone we’re in when I tell him the time of an appointment.
  • Matthew’s ability to do math in his head, despite being pretty good at finance, is horrendous.
  • I like coffee. Joseph loves coffee. Like… LOVES coffee…
  • Matthew only has one enemy in the entire world: himself.
  • The only thing that really bothers me about Joseph is the sound I hear when he is picking his nails.
  • Matthew’s thinking can be described as follows: If he had to build a bridge, he would have the vision to know exactly where the bridge should end, and the precision to know exactly where the bridge should start. But he would have no idea how to build the actual bridge. That is my role in our personal and professional relationship.

Here's to Year 2, filled with triumph, failure, growth, and gratitude!