Kids Launch the Darnedest Companies

Last year at a Startup Weekend, I was introduced to the most amazing six-year-old entrepreneur, Ashwin. We worked together on his product, Gap Tooth Stickers. After I wrote about it here on the blog, the story blew up, and Ashwin became a bit of a celebrity-news appearances, and calls from Shark Tank and national talk shows. Personally, I got emails from folks inside of Google, all the way to entrepreneurs from the UK and China. It was pretty incredible.

So when Ashwin's mother reached out to ask me to be a mentor at the first-ever Startup Weekend: Youth Edition, I jumped at the chance.

On Saturday, I headed down to City Hall, not really knowing what to expect. Circumstances had kept me from catching up with the organizers of the event, so I was going in blind. I had a rough idea of the day's format, but I figured my job was to show up, drink some coffee, and watch some kids bounce around some wacky ideas for a few hours.

Boy, was I wrong.

My Boss, the Six-Year-Old

On the first night of Startup Weekend, one of our initial activities is an icebreaking session. Last time, we had an epic rock/paper/scissors competition. This time around, we had to take two random words, and formulate a one-minute business idea around it. I don’t remember what the group I was paired with came up with. Although I know one of the words was bacon, and the business opportunities for that are limitless. I mean, tell me you’re not intrigued by the idea of Oompa Loompa bacon. Seriously. 

Anyway, we’re making our way around the room, and I’m already kind of tuning out. I found the rock/paper/scissors competition more compelling, to be honest. But one group pitched their idea–Oompa Loompa something or other-and at the end of it, a pipsqueak voice grabs the mic and says, “and we have ALL of the patents!”

Little Ashwin. 

Later, as we were settling in for pitches, I noticed a mother and her son in line. I thought it was cute, bringing her kid to something like this, and letting him run around with a lanyard to feel important for the evening. But we were in for a big surprise. 

Tara, his mother, pitched an idea about a social network for kids to use. But Ashwin stole the show. 

“Hi my name is Ashwin and I’m 6. And I am an entrepreneur. My idea is Wash Off Stickers. One day Mommy went to an event and put a name tag on. But when she came home she forgot to take it off and then threw it in the wash - but the sticker never came off and ruined her favorite shirt! 

My idea is Wash Off Stickers! With just a little water our stickers will disappear! And the stickers could go on walls, toys, even fruit!”


Not only did this little six-year-old identify a business problem, find a market, and propose a solution, he did it better than half of the grown-ass adults in the room. I felt terrible for whoever had to follow that kid. 

After the pitches, voting begins. At the beginning of the evening, we’re given three Post-its, which we use to vote for what we think are the best ideas. I walked around and chatted with a few people, and I noticed that Wash Off Stickers was sadly empty. This was an injustice that could not stand. 

“Oh, COME ON people,” I pleaded. “How is nobody voting for Wash Off Stickers?! That was an awesome idea!” I proudly placed my Post-It under his sign, and walked over to him. 

“Hi, my name is Dwight, and I just wanted to let you know I voted for your idea!” 

Now, I am not a small man. I’m 6’4”, and built like a lineman. It’s not that kids are scared of me, but most of them get real shy around me. Not Ashwin. He slowly looked up at me, smiled a toothy smile, stuck out his hand and said, “Hi!” 

I turned to Tara and told her that I know everyone else was voting for other stuff, but that if she decided she really wanted to do something with this, to let me know, and I’d be glad to help. She asked me for my business card, and said to Ashwin, “did you hear that? Dwight said he’d help you with your stickers! Isn’t that awesome?” 

“Yes!” Ashwin grinned. I gave him my business card too, which he stared at in awe, and proudly stuck in his pocket. 

“And if you have trouble at school,” Tara added, “Dwight will come protect you!”


“Of course!”


Eventually, everyone made their way onto teams, and I started working with a couple different teams on their projects (more on that later). And eventually, Tara and Ashwin headed home. On Saturday, Tara caught my eye and came over to me, and asked if I was still willing to help. Of course, I said. 

Turns out, I wasn’t the only one impressed with little Ashwin. Kyle Kesterson, one of the Startup Weekend gurus, founder of Freak’n Genius, and an awesome illustrator, had drawn up a logo and sticker for Ashwin, and she wanted to know if I’d help with the presentation. I told to take some pictures around the studio, send them to me, and I’d mockup some stuff for her. Between Kyle, Tara and myself, we managed to put together a presentation, complete with a business model and everything! 

Sunday rolls around, and Tara and Ashwin were nowhere to be found. I was starting to get concerned. With all of the teams I had designed work for, and consulted with, THIS was the one I was looking forward to the most. At some point during the day, the powers that be decided to let him go first, because “he wasn’t really competing or anything”. Knowing what I know now, I’m fairly certain Ashwin would object to that. 

They made it in with minutes to spare, and I walked over to him. This time, he looked a little more shy. 

“Hey Ashwin! You ready to go?” He shook his head. Turns out, he had his pitch memorized, but he was having trouble pronouncing a certain Black Art Director’s name. 

“De…Duh…Dwight?” he asked.

“Perfect. High five?” 

He grinned. “High five!”

I’m not going to try and do his presentation justice. I’ll just let you watch for yourself. 

The room burst out in applause. He handed out stickers to the judges (and anyone else in the room), and went on his way. Because of time, the judges didn’t get to ask Ashwin any questions about his business model or revenue streams, but I have it on good authority that he had answers ready to go .

Afterward, Ashwin won an award for being “the next Mark Zuckerberg”. So I guess that’s your notice, Silicon Valley. To paraphrase the great Jack Donaghy, in thirty years, we’ll all either be working for Ashwin, or dead by his sword.

Of all of the projects I worked on this week, my proudest contribution was to GapTooth Stickers. He’s the reason I do what I do, and I couldn’t ask for a better co-founder. 

Follow Ashwin on Twitter: @GapToothKid . For reasons unknown to us, Twitter suspended Ashwin’s Twitter account. We’re waiting to get answers, but for now, follow him @GapToothKid1.

UPDATE 5/22: Twitter has restored the original @GapToothKid account. Go forth and retweet!