How Letting off Steam Led to a Lucrative Side Hustle and Multiple Brand Collaborations

Play is often wasted on the young. It’s only once kids become adults that they forget how to flex this creative muscle. Don’t believe me? Walk by any school playground and measure the decibel level of kids at play. Now walk by an office building. The sterility and quiet are library-level even when studies show just how beneficial play is for overall health and productivity. 

But how do we get adults to play? Handstand is here to make play fun again with large-scale events and team-building activities that pop. Here’s how this accidental business found profitability and success to the tune of $150,000 ARR.

Handstand started as a happy accident. All of the founders held down corporate day jobs and got together on the weekends to rejuvenate. Josh Zipin, one of the founders, explains: “Our company began as an accident, to be honest. We were a group of friends that met at a workout group in San Francisco. We started going on a lot of adventures together, running and biking and backpacking and doing lots of crazy things outdoors. We were trying new things and building much closer relationships.”

This is what fun looks like.

Replicating Success

Josh credits the combination of “trying new things” and “great friends” as the reason the group had so much fun. Could they replicate that experience on a much larger scale? Josh says, “We wanted to build an experience that had all of those elements but was also challenging and tough – something that you’ve never done before – with people you like, and ultimately build much closer relationships. In 2014, we decided to build a city-wide scavenger hunt through San Francisco.”

Smartphones not included.

At the time, all of the founders were in their mid-twenties and working at various startups and businesses in the Bay Area. Josh says, “We all had a similar mindset that we were capable of more than our companies were letting us do. We realized that if no one was going to give us those projects that matched our ambitions, it was a great chance to prove to ourselves that we could do more. We were 20-something and a little arrogant,” Josh admits with a smile.

The first year, Handstand launched a massive public event, a city-wide scavenger hunt through San Francisco called The SF Hunt. They spread the word organically, and every person they met became a potential customer. Josh explains, “We were telling everyone we knew, and that includes every Uber pool we were in. It was super scrappy and homegrown.”

Capes are optional but positivity is a must.

A Friends-Based Business

Handstand also got a bump from a now-defunct events-discovery platform called Sosh. Josh and his team watched the number of signees grow exponentially. “We were shocked by the number of people who signed up and participated. We thought that if we got 75 or 100 people, even if 80 percent were our friends, we would be ecstatic.” Josh and his team had no idea how popular their idea would be.

The initial cost to fellow scavengers was low, and this was on purpose. Handstand didn’t want people to use cost as a reason for not participating. They sold tickets at $100 for teams of four. The first game launched entirely on Instagram. One of the founders, Gil Levy, a software engineer, built a web app to support the hunt. He did this entirely on his own, fueled by coffee and sleepless nights. As Josh describes it, “Our first product was built by a one-man team.”

The app contained a series of riddles that were all graded as “hella easy, medium, and impossible.” 

Each riddle led to a different location in San Francisco and the game rules explicitly forbid using cars and ride shares to get there. Walking, biking and public transit were all fair game, though. Josh said that this was intentional. “Everything is human-powered and city-powered.” There was no specific order, but each riddle was only deemed solved when it was uploaded to Instagram, had the appropriate photographic proof, and corresponding hashtags. 

The web app would then grab the location data from Instagram and verify that the submission was correct. The numbers were astounding. “With 400 people playing, and roughly 100 teams, there were something like 5,000 or 6,000 photos uploaded in a single day to Instagram. It was nuts.”

There were lots of rest stops along the way, and all of them were sponsored. This allowed Handstand to offer goodies to their patrons and involve local businesses in the fun. It was truly a win-win. The day ended with a food truck party and every participant got their first beer on the house. 

Camaraderie Meets Cash

The camaraderie and fun were apparent in every photo uploaded that day. The immediate response from nearly all of the participants was, “Wow! This is incredible – when can we do it again?”

Everyone involved still had day jobs. This was not yet a full-time business, but they began to see serious value in what they’d created. But maybe it was a fluke? They decided to test this theory by running another event. This one was a little different. Whereas the first event was a hunt, the second was a relay race and the phone served as the baton. The element that both events had in common was “pure unadulterated fun.” Play is the core of everything Handstand produces.

The second event took place over two days and involved costumes, a campout, and catered food. But it was not without its hiccups. There were checkpoints and teammates had to get from point A to point B in the fastest way possible. As you can imagine, people were googling routes which led to “really crazy stuff happening that in hindsight is pretty reckless or on the edge.” People were running through backyards and hedges, and it was mayhem.

When participants got back to the campground after cycling and running and moving all day, they were ravenous. This is where it gets interesting. The caterer was preparing small amuse bouche suitable for a wedding reception. Josh told her, “Lady, these people are dying.” Thankfully, this was sorted out and the event was a roaring success. 

Handstand had 120 people participate, which was no small feat considering they were asking for people’s entire weekends, including transportation with bike racks, and enough friends for teams. As Josh explains “there were so many hurdles we placed in front of you, and people still signed up!”

The group evaluated their second event and compared it to the first. They launched two successful events, spaced them several months apart, and received only positive feedback. But realistically, this was an enormous time commitment for a group of people with full-time jobs. It was then that the group decided to turn their play into a commercial venture. They pivoted to their first event as a model since it was easier to replicate on a larger scale. The “vision” as Josh describes it is “a tech-enabled Tough Mudder race.”

One Part Tech Wizard, One Part Ninja Warrior

The technology was impressive from day one. One player, Sam Goldstein, was so impressed with it, he insisted on “meeting the team.” Josh says, “There’s no team. There’s just this one guy. You can go meet him right now.” Fast forward to the player joining the venture and becoming best friends with the original developer, Gil. Sam brings pizzaz to the table as a former American Ninja Warrior contestant.

Around the time that the team was planning their next move, Josh was debating whether to leave his full-time job at a startup. Fate ended up deciding for him when the startup was purchased and all of the employees were laid off. If Josh was waiting for a sign from the universe, this was a pretty strong one and hard to ignore.

He talked to the rest of his team and they were mostly all onboard. They would launch Handstand. It would take a while for them to be profitable, and so they were leaning on their savings quite heavily at this time. Some of the team members kept their jobs and worked on Handstand at night. Luckily, they were able to pare their expenses way down and work out of Sam’s house for the first two years of the venture.

Every event they hosted enjoyed greater success than the one before it. An amazing 800 people signed up for the third event, which is astronomical when you realize that there was barely any advertising. In the spirit of conserving money, Handstand only dedicated $500 to Facebook ads and convinced local businesses to sponsor events. They viewed potential partnerships as “shifting from ‘they have something of value’ to ‘we have something of value.’” 

Here’s an example of what Josh is talking about: “Whenever there’s something that we should pay for, how do we get someone to pay us for that instead?” Josh takes this a step further: “Let’s get this running brand to supply us with shoes and pay us to participate.” It worked.

Handstand began to scale outside of San Francisco to six different cities: San Francisco, Seattle, Washington DC, Boston, Oakland, and Los Angeles. The team built iOS and Android apps since everything is played through a smartphone. The sponsorship deals scaled as well to include big brands like Sweetgreen and Lonely Planet.

Beloved Goofballs

This group of beloved goofballs still can’t believe their success. Josh peppers his conversations with sheer astonishment – “it’s crazy.” Other races and events in this space (see Color Run and Tough Mudder) rely on the ability to scale with advertising revenue. One competitor told Josh that they routinely put in millions of dollars in Facebook advertising. Since Handstand had a limited budget, they needed to figure out their next move, and quickly. 

Coincidentally, the Global Pandemic entered Stage Right. As companies were shifting to remote work, many were looking for team-building events on a virtual scale. Handstand found its sweet spot and moved right into the space of corporate team-building. It’s a great niche because running big events and scaling them involves weighing many factors that Handstand has no control over, including weather and “hangry” participants. A virtual funnel with a built-in audience is a completely different set of rules but the same amount of fun.

The best part is that Handstand evolved out of “a bunch of guys doing stupid stuff on the weekend.” They just finished hosting an event for all of the employees of LinkedIn, North America, so it’s clear that the friends are very much laughing their way through all of their successes.

Want to share your bootstrapping story with the world? Enter your details in this Typeform and we’ll be in touch.

Andrew Gazdecki
Andrew Gazdecki
Andrew is an award-winning serial entrepreneur with three exits. He’s the founder and CEO of MicroAcquire, the world’s most founder-friendly startup marketplace, and its rebellious child, Bootstrappers, which gives voice to the entrepreneurial underdog. When not building businesses, he writes for Forbes, Entrepreneur, and now, Bootstrappers.

Stay in the Loop

Get our weekly newsletter wrap-up with all the latest news in the Bootstrappers community.

Latest stories

You might also like...