Screen Shot 2013-07-19 at 1.09.10 AMIn perhaps the biggest battle to hit Silicon Valley, startup Square put more than 40 other companies to shame on Wednesday, including Google, LinkedIn, Uber, and Palantir. It won a 7-week tech competition to see who could own everyone else at sports ranging from soccer to Duck Duck Goose. For its prowess in the first ever Silicon Valley Sports League, Square will get a billboard on the 101 proclaiming the awesomeness of the company and its employees.

The competitions happened every weekend from June 1st till July 17th, and culminated in the finales at Candlestick Park where the San Francisco 49ers play home games. The crowning of the champion coincided with a giant carnival for techies who wanted to watch.

As you might imagine, the event was an excuse for everyone in the startup world to party like a kid, bouncy-box on astrojumps, blend smoothies by riding on bikes (don’t ask), fight over stuffed animal prizes, and ogle stilt-walkers. In other words, it was kind of like Google’s offices. Randi Zuckerberg’s band Feedbomb headlined alongside musical founder ensemble Coverflow. About 3,500 people showed up from 48 companies, paying $15, on average, for the privilege. I couldn’t make the event, but the HR Director of matchmaking startup Zoosk — Kimberly Saunders – filled me in on the details. Zoosk didn’t compete, but they sponsored the astro-boxing event and brought employees out to the carnival to help raise money. 

The proceeds of the carnival went to the Special Olympics. “I think that – and I can only speak for me personally – I find myself constantly feeling a little shame that I don’t do more,” league co-founder Misha Chellam said. The Silicon Valley Sports League creators recognize that launching a business takes laser focus, and there’s no time for “cognitive distraction” or spare capital. They see their sports league as a potential way to more easily integrate charity opportunities with the startup world — but that wasn’t their original plan.

Chellam and his fellow serial entrepreneur Russ Klusas started the Silicon Valley Sports League in April 2013, when they were expecting a slow summer. They are entrepreneurs-in-residence at Blumberg Capital and The Founder Institute, respectively, and have been bouncing around the startup world since the early 2000′s. 

In April, they emailed a few friends to see if they’d want to represent their companies in a small summer competition. But in classic viral fashion, those friends emailed their friends, and before Chellam and Klusas knew it they were fielding requests from the likes of Facebook and Linked-In. In all, 115 companies wound up expressing interest.

Like many successful startups in Silicon Valley, their idea gained traction and they soon had to scale up or risk failure. “We basically had a couple sleepless weeks of — oh wow, I kind of unintentionally got all these companies we respect and admire…excited about this,” Chellam says.

He and Klusas started scrambling, and spent a month pulling all-nighters, ordering equipment, booking fields, and cobbling together 40 staff to get things going. “We were totally unprepared… massively unprepared,” Klusas says. “So we were only able to let 44 teams in, but we were specific about picking cross sections of the Internet.” They chose bigger players like Evernote, and Yahoo, earlier stage startups like ApartmentList, incubators/accelerators like Y-Combinator, co-working facilities like Runway (Disclosure: that’s where Pando’s office is located) and even investment firms like Draper Fisher Jurvetson.

Employees of companies who wanted to join circulated lists and got other people to sign up. Then, they went to the CEO’s or HR directors to ask permission to fight under their startups’ name, Game-of-Thrones style. All summer, 2,000 people played a variety of games, ranging from ultimate frisbee to decidedly weirder ones. Turns out, lots of people in tech, “don’t play sports, but they do like covering their coworkers’ head with shaving cream to see how many Cheetos stick to it,” Klusas says. The finale Wednesday included around 12 teams, and Klusas and Chellam says Square wasn’t the original favorite to win — it was 7th or 8th in the SF team rankings.

Matchmaking startup Zoosk didn’t compete, but employees came to the festivities anyways. HR Directior Kimberly Saunders was manning the carnival astro-boxing and couldn’t watch the finals, but everyone coming off the field told her their teams were getting killed by Silicon Valley Bank (SVB). “They’re up against 6’7” investment bankers. What do they expect?” Saunders says.

Winning company Square poses with their trophy at Candlestick Park

Winning company Square poses with their trophy at Candlestick Park

Square went head-to-head with the bankers in their final game of flag football. Its quarterback kicked ass (“the MVP of the league in my opinion,” Chellam says), and Square ended up beating SVB, 40 to 24. “It was totally epic,” Chellam adds.

Klusas and Chellam didn’t want the massive event to just be about crowning a sports champion (“not to diminish the winners”), so when they booked Candlestick Park and realized how big the Tech Carnival was getting, they reached out to the Special Olympics as a charity partner. “Their message of sports uplifting people, regardless of who they are, resonated with what we were doing,” Klusas says.

They don’t have the numbers yet on how much they will be donating, but they said it’s a pittance (in the five-figure range) compared to how much their corporate partners could donate. “The true impact would be that [the Special Olympics] will form relationships with companies that can give them volunteers or write checks bigger than we can,” Klusas says. Zoosk’s Saunders says the startup is interested in partnering with the Special Olympics and got her business card before leaving the festival.

“I will say this — when you’re a startup or bootstrapping it, you cannot justify donating money,” Saunders says. “Your board is going to say, “No, that’s not how you do it.” Instead, Zoosk gives prizes and accolades to employees who volunteer together at the Tenderloin Community Garden, Glide food shelter, and animal group PAWS. Saunders believes that volunteering is a way for startups to bridge the gap between the capital they can’t give, but the causes they want to support.

“I think it’s easy to bet behind the idea of, ‘Oh we’re working at a tech startup so we’re changing the world,’” says the Sports League’s Chellam. “Startups in the community are reducing friction in people’s lives, but that’s not necessarily making the world a more just place.”