Side Show

A Side Project for Side Projects

What do you do when you run out of ideas for new side projects? You create a side project that aggregates and rewards other side projects. A simple idea thrown out during a phone conversation with one person grew to a 14 person team, a crap ton of social media likes and an outpouring of support from the advertising community.


Amazing Judges


Total Raised


Total Entries


Month from Concept to Launch


Paid Media


Creative Week Programs


Prize Per Category

Idea to Execution

My co-founder, Sunita Deshpande, and I came up with the idea at the very end of July. Over the course of a month we planned out the entire contest, grew our team to 14 people, booked 61 judges, 15 programs for Creative Week, built a website and oversaw mountains of social content.

We joke that if we'd known how much work it would be when we had the idea, we may not have done it, but naivety has it's benefits. Instead of worrying about the mountain we were about to climb we were able to focus 100 ft at a time which is way more managable.


Working with Camilla Ciappina, we built out a framework for our website then used Squarespace to develop it. Once the general structure was in place we had Grettel Aguirre create single line illustrations to bring it all together. You can view the full website here.

Website Stats

Sept. 1 - Oct. 31, 2020



Avg. Site Visit

Unique Visitors


Paid Media

Judging Platform

In order to keep our judging process organized, I built a custom platform using Wordpress. Judges were given access to specific categories via a welcome page.

We then created an entry for each submission that included a write-up and any photos, videos and audio that was to be considered. Everything the judges needed at their fingertips.


To cap our season, we put together a Creativity week filled with 15 programs that would appeal to people in the advertising and design communities.

Every day we hosted three programs and our hosts and guests included Jeff Greenspan (Former CCO, Buzzfeed), Lauren Ranke (Recruiter, W+K Portland), Xanthe Wells (ECD, Google), Kirsten Rutherford (GCD, TBWA\Chiat\Day LA), Mt. Freelance, and the Bag of Lies podcast.

We even capped the week off with a pre-recorded award show to reveal all of our winners.

All told we raised over $1,500 from the tickets that all went back towards our awards. You can see the whole lineup here.

Social Media

We made our Instagram account the hub our social media. We brought over the design language established on our website and used the grid to play with content in a way that showcased our judges, contests and programming in a natural, seamless way. Below are some of the posts.



When we launched the show, Sunita and I had committed to a minimum $500 prize for the Best in Show winner and $100 for each Best in Category winner. Not only did we hit our initial goal of $2,250 to cover all our estimated expenses, we blew it away ending up right around $6,000. This allowed us to raise each Best in Category prize to $450.

We also designed social graphics with a custom trophy thanks to my friend Alec Lewis. Every winner from Best in Show to Silver recieved one in addition to a mailed certificate to make the win more tangible.


Media Partnership

As we were launching, we were presented with an opportunity. Advertising News website AgencySpy wanted to partner up. They created a new section on their site dedicated to Side Hustles and used entries into our contest to source their content.


Co-Founder/CCO - Art
Josh D. Weiss

Co-Founder/CCO - Copy
Sunita Deshpande

Board of Directors/Website
Camilla Ciappina

Board of Directors/Student Contest
Bre Fernandez

Board of Directors/Student Contest
Laura Canzano

Board of Directors
Maddy Kramer

Contributor/Art Director
Grettel Aguirre

Contributor/Art Director
Jelly Marasigan

Dillon Hansen

Andrew Thompson

Contrbutor/Product Design
Yanci Wu

Contributor/Project Manager
Isaac Lee

Contributor/Social Strategist
Nico Rud

Contribtuor/Community Manager
J.L. Perez