Derek Haswell

Before working with Derek, I saw coaching as a way to be more effective - as a CEO, as a founder, as a builder. Derek’s been amazing at that. We’ve jammed on everything from team building to strategy to product design. He’s exceptionally smart, and from his years as a founder, knows exactly where to push and probe to get to the heart of a business problem. But what makes Derek’s coaching different is that he goes deeper. It’s his unique ability to move between the practical challenges of building a company and the much bigger questions of identity, purpose, and what makes a meaningful life.

Through our work, I’ve not only articulated my personal values for the first time, but actually begun to build an architecture for living them. I’ve unpacked my identity and engaged its different parts in ways that have reshaped how I think about who I am. And I’ve started to evolve the fuel that drives me in my work, from the need to win and prove myself toward a deeper sense of purpose, curiosity, and love for what I’m doing and the people I’m doing it with.

One result is that I’ve become a better founder, builder, and CEO. But the direct results of the work itself have been even more meaningful: greater self-knowledge, cleaner personal energy, and a clearer direction not just in my work, but in my life.

Derek is uniquely capable in his holistic approach to coaching: from sharp perspective on day-to-day strategic and operational questions to intuitive guidance on more personal, inner journeys. He's coached me from the earliest days of my third startup through our $50M Series A and beyond. It's been both a pleasure and a superpower. As I and my company have grown, our relationship has kept pace, and proven time and again more valuable than I thought coaching could be.

Derek is a rare Swiss Army knife of coaches. He brings deep experience navigating both inner and outer worlds, and I loved being able to draw on that range in our work together. In a single conversation, we could move from IFS parts work to exploring awakening to high-level business strategy for my business. That breadth made him a tremendously effective coach throughout our several years together.

I’ve really liked working with Derek. He gives me a sounding board for feedback and difficult work conversations, and talking things through helps me find my own solution, gain perspective, and avoid rushing in. He also challenges me to think differently about my organization and my role in it: what the team should look like six months from now, who should own what, and where my time makes the biggest difference. We’re building toward a team that’s more effective and a role that fits what I actually enjoy. Along the way I’ve gotten better at giving feedback constructively and building more alignment with my co-founders.