Coaching & Advisory
A partner for consequential chapters.
I’m a coach and strategic partner to founders navigating transitions and inflection points.
Start a conversationThe work
Clarity when the next decision matters.
When a founder needs to change directions, level up, or make a decision that will define the next chapter, I bring 15+ years as an operator, venture investor, and board member across 100+ companies directly into the work.
That looks different for every founder. It might mean building a fundraise strategy and opening the right doors. Navigating an acquisition conversation with clarity instead of anxiety. Building the organizational structure to scale without breaking.
And sometimes the most important work isn’t “strategic” at all. It’s helping a founder navigate the isolation, pressure, and self-doubt that comes with the job, so they can show up clearly for everything else.
How it works
Built around you.
First conversation
Every partnership starts with a 45-minute intro call—your first taste of live coaching and a quick check that we’re the right match.
Deep dive
We begin with a 90-minute session to clarify what matters most and build the context for our work.
Ongoing partnership
We meet twice a month. Between sessions, I’m available by phone or text when things come up.
I keep my roster intentionally small so I can give you real energy and attention, not a distracted check-in.
What I bring
In the trenches. Above the tree line.
I know the late-night fire drills and boardroom dynamics firsthand. As your coach, I meet you in those trenches, then help you rise above the tree line to see the bigger picture.
I coach the whole person, not just the role. Purpose, presence, energy, relationships. These aren’t soft extras. They’re the foundation that makes sustained performance possible.
Founders and athletes have more in common than most people realize: both are fully committed, both operate under intense pressure, and both perform best with the right support around them.
I’m an ICF-certified coach, trained in Co-Active Coaching and Conscious Leadership.
What clients say
“Building a company comes with both shiny highs and rough, ugly lows. Dillon was with us through all of it, never shying away from uncomfortable conversations and always asking the tough questions. He’s everything you’d want on your team: grounded, consistent, and iterative.”
Selected clients
Begin here