Emily OBrien

Here’s why you should know about Emily O’Brien, this absolute fire startup founder you gotta know about. She’s from that YC W19 batch, so she’s legit in the game. Started out with a solid background, worked at GIPHY, Refinery29, The Ladders, Manage This!, did some freelance gigs, and even dipped her toes into the art world with Gagosian Gallery and NYLON Magazine. Basically, she’s been around the block in both tech and creative spaces.

But what really makes her stand out is her hustle and how she’s not afraid to jump into the deep end. She co-founded Cherry in 2018 with her sister Gillian, yeah, a sibling duo, that’s always cool. Cherry was this great idea, let employees pick their own perks, which is kinda new if you think about it. The goal was to shake up how companies handle benefits, giving workers more control. They crushed it early on, raised over $700k in angel funding, landed 40+ paying customers, and got into YC, which is no joke.

But here’s the kicker, Cherry was a startup during COVID, and honestly, it was a tough scene. They wound down after a rough seed round, but that doesn’t even tell the full story. Emily’s process isn’t just about the wins; it’s about the grind, taking a shot, learning from setbacks, and still pushing forward. It’s classic startup stuff, fail fast, learn fast, then pivot or move on.

What I love about her is that her story screams motivation. She’s all about the real deal, building, experimenting, failing, and jumping right back in. Her experience at big companies and creative gigs shows she’s got a wide lens, she gets tech, culture, art, and business all at once. That’s rare. She’s probably driven by a genuine desire to make work better, more flexible, more human.

And even though Cherry didn’t make it, the lessons she’s learned are gold. It’s clear she’s not done, she’s got that entrepreneurial fire, and she’s probably cooking up her future trend. She’s proof that starting something isn’t about hitting a home run right away, it’s about the hustle, the passion, and the guts to jump into the unknown.

So, in short, Emily O’Brien is this fierce, multi-talented founder who’s been in the trenches, learned hard lessons, and still keeps pushing boundaries. She’s all about innovation, resilience, and making a real impact, no cap. Definitely someone to watch as she keeps crushing it in whatever she does next.