Coaching for Founders
“The wind and the waves are always on the side of the ablest navigator.”
Empathy. Compassion. Direction.
tack, verb, nautical: to change the course of a sailing vessel by steering it into and through the wind.
FounderTack is a private coaching practice, specifically focused on helping early to mid-stage founders navigate the challenges involved in leading their startups.
Every founding journey is different. But as founders, we often encounter similar challenges:
Imposter syndrome that makes us question whether we really know what we’re doing.
Maintaining a work/life balance that ensures that we don’t jeopardize our most important relationships, our health, or lose sight of who we really are.
Managing and resolving conflict with our co-founders and executive teams.
Staying sane while raising venture financing.
Figuring out who we are if our companies struggle, or even fail.
FounderTack focuses on helping you find and focus on what authentically matters to you.
Kevin O’Brien
Founder and Coach
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 complex exits.
I coach entrepreneurs as they navigate these waters.
Every client-coach relationship is unique, but the framework I use starts by diving deeply into your core values and beliefs, uncovering the goals, assumptions, reactions, and experiences that inform what you 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.
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. 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.
Reach Out
Deciding to work with a coach is a significant decision, and it’s natural to have questions about the process, the outcomes, and the experience.
We’re happy to chat, with absolutely no pressure or sales pitch involved. Reach out and we’ll be in touch shortly.