Listen to Noomii's interview with Kevin O'Brien

About Me

Serving as a founder, no matter what your company does, is an all-encompassing challenge. It’s incredibly rewarding, but it also shakes you to your core – every insecurity, every moment of imposter syndrome, every conflict and moment of lost conviction comes home to roost when you are in “the seat”.

I speak from experience: I am a former technology CEO and founder, with nearly 25 years of experience working in, building, founding, leading, and selling startups. I have deep expertise in the venture-backed world, having raised over $30m USD, leading multiple companies, and managing a complex exit to private equity.

My coaching practice is focused on helping entrepreneurs - typically but not exclusively earlier in their company's journey, often pre-Series B/"scale-up" - navigate these complex issues. I focus on helping my clients get in touch with their core values and beliefs, and to uncover the assumptions, reactions, and experiences that inform what they see as true. By engaging in a sustained dialog, I can help you evaluate what was previously accepted without question, identifying and keeping what works, and changing what does not.

In doing so, I draw on extensive experience, including outside of my own work as an operating CEO. I have served as a mentor-in-residence with Techstars since 2015, helping dozens of CEOs navigate fundraising, team dynamics, product market fit, early stage marketing, and finding balance as a leader. I also serve on various boards of directors, and in addition to his own entrepreneurial ventures, has been an early member of multiple successfully exited technology companies, largely in the cybersecurity sector.

I hold a BA in Philosophy from the University of Massachusetts Amherst, and outside of work I am a lifelong martial artist, avid sailor, and zen practitioner.