I’m a coach and strategic partner to founders navigating transitions and inflection points.
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
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. From there, everything is tailored to you.
We begin with a 90-minute deep dive to clarify what matters most, then meet twice a month to work through whatever is top of mind. 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
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.” — Ashe Magalhaes, Founder & CEO of Hearth AI
Selected clients from: Salesforce · Techstars · Y Combinator · Ada CX · Quanta · Brev.io · Wrangle · Synch · Clockwise · Workramp
Dillon Ferdinandi 