After 4 Years with Funsize, I’m Leaving to Start My Own Adventure.

Rick Messer
6 min readJul 29, 2016

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A gushy story about how I got started with Funsize, why I loved my time there, and why I’m moving on.

My Funsize Story

4 years ago, I was working at a startup called SceneTap. In the face of designing my first mobile app I reached out for local help in Austin. I found a company called 39 Argyle that Anthony (now owner of Funsize) was running at the time. They specialized in mobile and I was excited to work with them. Right as we were finalizing the project, I learned that Anthony was no longer going to be part of the company, that he was moving on to work at Evernote. Since working with him was the main thing I was excited about, I decided not to go through with it. Instead I designed SceneTap’s iPhone and Android apps myself, learning as I went.

But Anthony and I kept in touch. Being new to Austin, my wife Jenny and I didn’t really know anyone. Anthony and I had beers regularly, eventually hanging out together with our wives. We talked about music, design, travel and our personal goals. We had become good friends.

After some time, I learned that Anthony was thinking about leaving Evernote to start freelancing. Hungry for collaboration, I jumped at the chance to interview him. He blew my team away with his answers to our questions. I remember asking him about salary. I will never forget how he responded…

“I don’t give a fuck what it pays! I design products, so that’s what I’m going to do regardless.” –Anthony Armendariz

I worked with Anthony for a little here and there showing him what I was working on and we would critique each-others work. But he never ended up working for me. Instead, he was excited about starting his own company again, but this time, with his wife Natalie.

I remember playing pool with him one night at Barfly’s when he told me his plan. But I didn’t think it was a good idea…

“Man, I’m sorry that just will not work. You should keep your business life and personal life separate so you don’t blur the lines. It’s just not a good idea to start a company with your wife.” –Me, giving what I thought was sound advice

It takes a very special type of person, to be able to run a business, let alone run one with your spouse. Turns out though, Anthony and Natalie had an unusually complimentary dynamic. They worked very well together and I was pretty surprised how well-suited they were to run their company.

Fast forward a few months, Anthony was asking me if I could help with a big project he had landed with Groupon. I was already freelancing and had done one project with him for a Windows Phone app. I was excited to work on a big iPad project. So, we jumped on a plane to SF (the first of so many), and kicked off the project. I believe that’s when Funsize was starting to become a real company. I worked with them for about a year as a contractor until joining officially in December of 2013.

We started hiring designer friends we admired in Austin, keeping things close-knit and focused on building a culture that we were proud of. Offering a unique experience as a product design team that operated directly with clients’ existing teams.

Things I’m Proud of From My Time Here

Funsize continued to grow, and so did I, as a designer. While working here, I ran projects for Groupon, PayPal, Honeywell, Open Table, and something like 30 start ups. Because we were able to keep client work off of our Fridays, I used the time to try some new things:

My role grew into the design director position, and I learned how to run a bad-ass team capable of assigning pleasant usability to complex ideas.

Some memories of my time with Funsize…

A week-long workshop with a client in Finland.
That one time we went to Utah and played at Arches National Park.
How we spent so many days, sketching, working together. Me with Danielle Moser.
Motorboating at epicurrence Montues
Our Finnish Client, Ōura presenting their product at Launch showing our work in their demo video.
Funsize crew + friends representing at Halloween 2014
Google visit 2014
Me and Natalie Armendariz posing for an action-shot.
Me and Phi Hoang working on the app-in-a-day project.
My kid, Caleb, sportin’ a Funsize Onesie at 2-weeks old.
Reviewing some UI with Ulf Schwekendiek on an SF visit in 2014.
Slopes of Tahoe at Epicurrence 2016
Elevator Selfies in Chicago 2014
Most of the team saying good-bye to Andre Jurgensen as he moved to Bend, Oregon.

So why am I leaving?

I’ll try to keep this part short and sweet…

There’s not a lot of negatives to working at Funsize. It has been really fun and rewarding. I feel like I’ve been helping Anthony and Natalie create their dream company. Now that I have learned what it takes, and what I think that really is for me, I need to find my own dream… I think this was a big part of the post I wrote a year or 2 ago about taking my career too seriously.

I did not aspire to start my own agency but, in seeking for my true North, I took interviews and had a lot of soul-searching lunches with my friends (you know who you are ;-) and thanks). Talking to them about how I feel sort of “incomplete” in my work and that I want there to be more meaning.

Opportunities seemed to be coming up, but they just weren’t right for me. Some would take me out of Austin (which I don’t want to do at this stage, but honestly that’s another post), others were cool companies here in ATX but I just couldn’t quite get excited about their products (except one, but they didn’t call me back).

Then Something Came Up That I Didn’t Expect

Recently, I got an opportunity to start my own business up with a partner whom I truly respect and admire (sorry, can’t say who it is for now 🤐).

Considering this, I realized that what I truly want is to work with incredible people who I admire. We all spend so much time working and trying to accomplish something, but lately I’ve been really concerned with making that time meaningful and enjoyable. Because this particular opportunity would partner me with this individual, I just couldn’t pass it up. The thought of not taking the chance sounded far worse than the thought of it not working out.

I’m Excited To Live a Story Worth Telling.

So with that, I bid Funsize adieu. I’m a better designer for having worked there with these people, and these clients. The passed few weeks have been a toss-up of freaking-the-hell-out, fist-pumping as I drive down the highway in self-convincing fits of flail to the most fist-pumpingest tracks, and pure surreality. With support from a lot of great friends and mentors, I’m confidently marching into this next chapter. I can’t wait to announce the full details but for now, I leave you with this…

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