Gillian OBrien

Meet the absolute unit that is Gillian O’Brien, this girl’s the real deal in the startup world. She jumped into YC W19 with her sis Emily, and they cooked up Cherry, this HR SaaS platform that let employees pick their perks through a Slackbot. Super clever, right? Over 40 paying customers, raised over $700k in angels before shit hit the fan during COVID and they had to wind it down. That’s startup life, no cap, it’s all about trying, failing, learning, and pushing forward.

What’s crazy is she didn’t just stop there. After Cherry, she jumped into the startup scene again, becoming a ‘Startup Evangelist’ at Pilot.com, where she’s all about building communities and sharing lessons. She’s super open about the failures, no bullshit, that’s how you grow. Her whole vibe is about turning setbacks into lessons and helping others not make the same mistakes. Plus, she’s into wellness too, she’s a yoga instructor, which shows she’s all about balance and self-care even in the chaos of startups.

Gillian’s story is about grit, guts, and genuine passion. She’s not just in it for the success; she’s in it to learn, to connect, and to make an impact. Starting Cherry with her sister? That shows she’s got mad trust and loyalty. Winding down after a tough round? That’s real, that’s what makes her relatable and inspiring. She’s proof that you gotta jump in, try your best, and be proud of the lessons you pick up along the way.

Honestly, Gillian’s process says a lot about her motivation, she’s driven by more than just money or fame. She genuinely wants to improve how we work, build communities, and help founders grow. That’s why she’s so important. She’s not just another startup founder; she’s a leader who’s not afraid to show her scars, share her story, and lift others up. That’s what makes her the real deal.