The Side Show


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.

Quick Stats


Amazing Judges


Prize Money Given


Total Entries


Month from Concept to Launch


Live Events

Prize Per Category


Paid Media


My co-founder, Sunita Deshpande, and I came up with the idea at the very end of July. 2020. 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.


After the first two years of The Side Show, we decided to change formats to be more of a gallery. This required rebuilding the entire site from the ground up. We brought on Serra Semi to help us redesign the site with an eye towards how we could grow our offerings.

You can view the full site here.



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.



Reflective of current team

President  // Josh D. Weiss (Me)
VP, Creative // Sunita Deshpande
VP, Website // Serra Sem
VP, Live Events // Jessica Urgo

Co-Founder & CCO - Art // Josh D. Weiss (Me)
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

Contributor - Copywriter // Dillon Hansen
Contributor - Artist // Andrew Thompson

Contrbutor - Product Design // Yanci Wu
Contributor - Project Manager // Isaac Lee
Contributor - Social Strategist // Nico Rud
Contributor - Community Manager // J.L. Perez

Co-Founder & CCO // Josh D. Weiss (Me)
Co-Founder & CCO // Sunita Deshpande
BoD - Website // Camilla Ciappina
BoD - Student Contest // Bre Fernandez
BoD - Student Contest // Laura Canzano
BoD // Maddy Kramer
Art Director // Grettel Aguirre
Art Director // Jelly Marasigan

Copywriter // Dillon Hansen
Artist // Andrew Thompson

Product Design // Yanci Wu
Project Manager // Isaac Lee
Social Strategist // Nico Rud
Community Manager // J.L. Perez


ebay motors' Between 2 RidesTwin-turbocharged fun for the whole family.

Toyota Super BowlFeatured in AdWeek, AdAge & Creativity Online - A Rabbi, Priest & Imam walk into a football game...

The Amanda FoundationFeatured in AdAge & LeBook - Everyone is worthy of the love of a dog, even people in advertising.

Georgia LotteryReally bums me out that these hands had a better fashion sense than I do.

Trump Rio GrandeFeatured in AdWeek - Introducing the World's First .5 Star Resort.

Back to the Future1.21 Gigawatts of fan service

Toys'R'UsPlaytime is WAR

Toyota 4RunnerBears, Bison and MOTHs. Oh my.

Energy Upgrade CaliforniaWe were told this could sink or save Gavin Newsom from his recall election.

Demosthenian Literary SocietyGo Viral for Something You Can be Proud Of

The Side ShowFeatured in AdWeek - The side project that rules over all other side projects.

Weird, Strange, Bizarrely 100% Real AnimalsMy wife thought all the fake animals would confuse my nephew, I said "good."

Assorted SocialSocial, Photography, Video

Additional ToyotaProject type

Design & TypographyProject type

PhotographyI once had an NBA Center land on me at a game, he was the one who had to get checked by a doctor.