Seeing the Future: A DI Alumna’s Journey to Entrepreneurship

By: Angela Wright, DI Alumni Ambassador

Destination Imagination (DI) alumna and CEO of Wondermile, Anna Palmer, talks emergency retrofitting, rapid problem solving and her journey to entrepreneurship.


How did you first become involved with Destination Imagination?
I was recruited through school in fourth grade and participated through eighth grade.

What was your favorite challenge to participate in?
Generally, my team liked to do the Technical Challenge; we liked to build cars.

What is your favorite memory from your time as a participant?
I have two! My first is from my fifth grade season. We made it to the Global Finals tournament and we were seated at the awards ceremony. We didn’t expect much — the room was full of competitors much older and more experienced than us. All of a sudden, our name was called. We had won the DaVinci Award. Walking across the stage and being recognized for our creativity, because of the culmination of our hard work, was so formative for me later in life.

My second memory is from my first season. One lesson you learn early on in DI is to always read the Challenge fully, and that was not something we had done. We accidentally built our props to fit through a double-wide door instead of a standard size door. So, we showed up, and they did not fit. We expected the worst, but our Appraisers pulled us aside and said that they were not going to disqualify us. They gave us until the end of the performances to adjust our sets to make it fit. In two hours, we cut all our props in half, hinged them back together, lowered the chassis of our car by three inches and managed to get out and perform. We won the Central Challenge that day but lost the Instant Challenge, so we didn’t move on. Those two hours taught me what real-time problem solving looked like.

What do you do now?
I have two major roles. My first role is CEO and co-founder of Wondermile, a company which is simplifying online shopping. If you’re looking for a couch in your neighborhood, we make it easy to find that couch and have it in your home in under an hour. My second role is a founder and investing partner in XFactor Ventures. We give up to $100,000 to seed-stage startups that have at least one female founder.

Your resume has you going from law to politics to fashion — and then entrepreneurship. Were you chasing a specific goal or dream at each stage?
Not at all. I knew I liked to build and create things. I went into politics on the campaign side, where I would oversee rallying people behind a cause. What I loved about that were all the mechanics it took to set up a rally, the creativity it required to involve my target audience, and how quickly those groups would then rally behind a cause. So, I went to Harvard Law thinking that politics was the place I wanted to end up. But while I was there, I missed the creative element I had when working on campaigns. Campaigning is about rallying people around a cause to help solve problems in your community.

That’s what lead me to my first company, The Fashion Project. I realized that when you dropped off high-value items for donation at a Goodwill, Boys and Girls Club or other donation center, they did not have the systems in place to accurately get the item’s full value. The Fashion Project was a unique donation drop-off where you could bring in your designer item, we could accurately get the value and then provide the full value to the charity of your choice. This is where my love for fashion and entrepreneurship started. And if you had told my high-school-class-president, khaki and polo-wearing self, that that project would land me on the cover of fashion magazines, I would not have believed you.

Why is Destination Imagination important, especially for girls?
It’s vital. You can find any information you want on Google, but in everyday life, a lot of the issues you deal with require problem solving. I think this program is so important because it taught me that the solution almost always comes from outside the box — and it gave me the confidence to build and create my solution. DI once taught me how to build a working car out of an old lawnmower motor.

The skills I learned from DI were most formative and have influenced my daily life more than anything. I use my problem-solving skills every day at Wondermile, trying to figure out the best way to take a photo of an item so that it gets sold, or how to get it delivered in time.

Bonus Story: I have a picture of my first costume. I was a Tooty Fruity Fish. We fourth graders were going to make a costume out of construction paper, a leotard and hot glue. We realized quickly that we couldn’t glue the construction paper to the leotard by itself because the material would stretch. So, I put on the leotard, and we started to hot-glue on our construction paper “scales.” I didn’t talk to some of my team members for a week after that. The parents freaked out about “Who wasn’t watching while they were using the hot glue?!” I still have the scars, but that story always makes me laugh.