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How A Two-Person Startup Won Chicago Tech Madness

David stoned Goliath, American revolutionaries sent home the British kingdom, #16 UMBC took down #1 Virginia in the NCAA tournament, and Choobs won Chicago Tech Madness.

How did Choobs, a two-person startup that nobody’s heard of, get enough votes to beat billion-dollar startups with hundreds of employees? How did a #16 seed go all the way?

On an afternoon in early February, Chicago Inno, the top publication for local startup news, sent me their daily newsletter which I’ve subscribed to for three years. It said to nominate startups for this year’s Tech Madness bracket, a March-Madness-like competition where people vote for which startup they’d invest in, and the company with more votes moves on to the next round. I’ve followed and voted in this competition for years.

I quickly nominated Choobs, a tech startup that I launched 7 months prior, and went on with my day. Choobs is a bootstrapped company that had zero publicity and few followers. I didn’t expect to make it in.

A month later, on March 9, the newsletter hit my inbox again. This one announced the bracket, and I opened it with little hope. Like your own name popping out at you, the very first thing I saw on the bracket filled with 64 companies was my company, Choobs.

I assume the team at Chicago Inno had more than 64 nominations, so some companies had to be cut. How did we get in? Maybe Choobs made the cut because we already had launched a product and were doing business. Maybe it was because they liked our mission or website. Or maybe they just picked out of a hat to decide which company would get the final spot…

All I know is my feeling of excitement lasted for less than one second because the next thing I noticed was Choobs got the #16 seed. Anyone who follows March Madness knows that a #16 seed is the lowest seed in the bracket.

Considering my expectations, I should have been happy just to be in the competition. My company was on the same page as popular Chicago startups – Foxtrot, Cameo, SpotHero, Farmer’s Fridge. That’s pretty cool! But competitors like me can be irrational, and a little fire lit inside of me when I saw that #16 next to Choobs.

We would face a #1 seed, Avant, in the first round, and I felt a burn to win. To prove Choobs worthy of Tech Madness and get revenge for being a #16.

My love for sports taught me something about human nature – everyone loves an underdog. I’ve always cheered for underdogs in March Madness, World Cups, and Olympics. The country cheered when Loyola-Chicago made the Final Four, people went crazy when Leicester City won the Premier League, and we never forgot when U.S.A beat Russia in hockey. I figured I could rally people behind #16 Choobs beating #1 Avant. All we had to do was get more votes than them.

With an attention-grabbing tweet and a post on LinkedIn, we were off to the races. The posts racked up likes, shares, and comments from friends and random people alike. Human nature was in full force… Beat Goliath!!

I added fuel to the fire with memes. You know what they say… tell a man to vote and he’ll vote once, rile him up with memes and he’ll vote every day. Honestly, I made these memes for my own entertainment…

Even with this traction on social media, I didn’t expect to beat Avant. Any random person passing through the bracket would vote for the company they recognized, Avant, over Choobs. That meant we would need more votes than Avant employees AND neutral voters. How could we work smarter?

I found a link to make voting much easier, figured out that the site would allow me to vote every 24 hours, and found that each device and browser let me vote additional times each day. While they voted once per day, we were voting 5 times. That’s working smart.

As a result, the #16 seed no-name startup with 2 employees beat the 1.5 billion dollar, 500-person startup. Mission accomplished!

Chicago Inno wrote about how Choobs won, our site got a little traffic bump from the news, and I was satisfied with pulling off the best upset in Chicago Tech Madness history.

The story could’ve very well ended here. Choobs was to face another well-known startup, The Mom Project, in the next round (and I figured a name like that would beat Choobs easily). I didn’t make memes and hardly posted about voting, but somehow the voters kept voting, and we won again! We were going to the Sweet 16, and now I felt motivated to make a push.

The memes were flying, and Choobs kept winning.

We rolled past #5 Chowbus ($68M raised) to get to the Elite 8.

The rounds would last 3-4 days and the winner was always shown at 11:00 pm on the last day. My mind juggled between “we got this” and “no chance we win again.” I rarely stayed up to see if we won, opting to find out in the morning instead.

We knocked off #7 HealthJoy ($48M raised) to make the Final Four.

We danced past #7 PerkSpot ($50M raised) to stake our spot in the Championship.

I saw friends and family feverishly voting every day. Each time we won, people wanted to know what I’d get if Choobs won the championship, and the answer was always… “nothing.” The lack of reward didn’t stop the voters, though. People I haven’t talked to in years told me they were voting every day. Secondary connections were sharing the voting link with their extended families. Someone I knew well was confused when he got told to vote from someone who didn’t know me. A Barstool Sports personality tweeted to vote for Choobs. Gies College Of Business tweeted to vote for Choobs. My high school teachers joined in too. How could something so meaningless spread so fast? Everyone just wanted to see a good old Cinderella story.

And so we faced a #5 seed, M1 Finance, in the Championship. M1 is a startup with 150 employees and $170 million in funding, but I no longer feared that they had the employees, the publicity, and the flashy name. Choobs had become an unstoppable force in Tech Madness.

I sat with a few friends at a live music bar on April 1, just three weeks after I made those first posts about voting for Choobs in Tech Madness. With a refresh of the voting page at 11:00 pm, while the musician played an acoustic version of The Rolling Stones’ You Can’t Always Get What You Want, I got what I then wanted. Choobs won 2021 Chicago Tech Madness! It turns out that we got over 75% of the vote in that championship round.

I never dreamed of winning the whole thing. I badly wanted to win that first round against the #1 seed and I was satisfied after that. But when an underdog picks up steam, and people have an opportunity to feel part of a movement, they join in. It’s human nature.

I’m very grateful that Choobs was the vehicle for excitement this March. Winning the competition doesn’t mean that Choobs is the favorite startup in Chicago or anything like that, but it does signify the strength of my community. A damn good community!