Brooklyn tech founders and CEOs spill their Valentine’s Day stories

We asked some of the Brooklyn tech scene's finest about awkward dates and nerdy romantic gestures — and they did not disappoint.

Winners of Technical.ly's 2016 Brooklyn Innovation Awards. (Photo by Brian James Kirk)

Here at Technical.ly we thought Valentine’s Day would be a good opportunity to step outside of StartupWorld for a minute and remember that, for now at least, we’re all still human beings with feelings and real lives.

So with that in mind we sent out a questionnaire to some of the movers and shakers of the tech scene asking them about their best Valentine’s Day memories. They came back with some wisdom, some passion and some snappy answers. Enjoy.


What was your weirdest Valentine’s Day? If none, your weirdest date, generally?

“I met someone through a now defunct online dating site around 2006 and was pretty excited for the first date. I showed up at the movie theatre and noticed someone who resembled my date’s profile photo only with the addition of two young kids in tow. I love kids, just didn’t know that she had any or that they would be joining us. I did my best to be a good sport about it and embrace the situation. After the upbeat Disney movie, we grabbed dinner at McDonalds while her little ones got wild in the ball pit.” Dave Cascino, founder and CEO of Thunderclap.

“I once went on a first date—to dinner: spaghetti, wine, the whole thing—on Valentine’s Day. We thought it’d be funny. It wasn’t. It was cringe-worthy.” Molly Erman, Director of Communications at New Lab.

What would you write in a valentine to a mentor or someone who has helped you along the way?

“To just about any grad school professor: You were always telling me to slow down and be patient and look where I am now, SUCKAAAAA!  (PS thanks for putting up with my nonsense.)” Isis Shiffer, inventor of the EcoHelmet.

“Thank you for helping me to be my best self ?” April Joyner, Technical.ly Brooklyn Contributing Reporter.

I just watched the movie Whiplash, about a jazz drummer who commits totally to becoming the next great drummer, and he decides to break up with this girl he’s been seeing so that he can devote all his time and energy to working on drumming. Have you ever had to do something similar?

“I think most people have experienced this dilemma in some shape or form. I’m originally from the UK and when I had the chance to move to New York it was a tough decision between a wonderful life in London, and all the exciting possibilities of moving to NYC. You can’t always let dreams get in the way of love, but sometimes your heart has other plans. Sidenote: Such a good movie!” Stephen Tracy, cofounder at Keap.

“My boyfriend, who’s a restaurant guy, works long, opposite hours from me. This has actually been beneficial to us professionally: we’ve got ample space to hustle without anyone feeling neglected.” Molly Erman, Director of Communications at New Lab.

“I’ve had to uninstall League of Legends. Does that count?” Nisha Garigarn, cofounder at Croissant.

“It’s tough to commit to someone while dedicating your time and energy to building a company. You’re both emotionally and physically unavailable most of the time. I feel pretty lucky to be dating someone who understands the startup world and still supports me in this journey.” Allison Kopf, founder and CEO at Agrilyst.

“If you want to achieve big things, it’s important to stay focused on your goals. Often, those come at the expense of something else. However, the longer you do it, the more you realize how important it is to have a life outside your business as well – enjoying time with your family and friends and having regular down time makes you better at work and overall happier.” Veronika Harbick, cofounder at Thursday Finest.

When you meet new people is it hard to explain what it is that you do? 

“I give up really easily. If someone wants to know what I do for a living, I’ll first ask if they know what coworking is. If they don’t, I just try to change the subject as fast as possible, ie. ‘Nevermind, I’m a designer. So have you been here before?'” Nisha Garigarn, cofounder at Croissant.

“No, but I recently had to explain blockchain to someone, and that was quite difficult.” April Joyner, Technical.ly Brooklyn contributing reporter.

What’s the nerdiest romantic gesture you’ve ever shared with someone?

“I met this guy I really liked and decided the way to get him to notice me was enter the local kinetic sculpture derby and put him on my team. We made a bike powered rolling catapult that shot paint filled water balloons at a canvas to make instant art. It wasn’t designed very well and at the derby most of the paint wound up sliding off the canvas onto my crush’s head. He must not have minded too much as that was almost seven years ago and we’re still together.” Isis Shiffer, inventor of the EcoHelmet.

“I don’t have great answers for most of these, but I did meet my now wife at a tech conference where we were both pitching our (then) startups.” Brad Hargreaves, founder of Common.

And finally, we had one respondent who mostly deferred answering the questions, but did have one sweet, wistfully nostalgic anecdote.

“My Valentine’s day message is this: you’re all going to die alone, doomed to be forgotten.” Brady Dale, reporter at the New York Observer and beloved former Technical.ly Brooklyn lead reporter.

Happy Valentine’s Day, y’all! ?????

Series: Brooklyn

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