Founder and CEO Coaching From Someone Who Has Been There
At a certain level of scale, the decisions carry more weight and things get quieter around you. Fewer people tell you the truth, and old instincts strain against new complexity. This is what founder and CEO coaching is built for: not advice from the outside, but a confidential thinking partner who’s actually done it.
I’m David Dressler. I spent over a decade co-founding and scaling Tender Greens from one restaurant in Los Angeles to a 1,200-person, $100 million business, through a successful exit. I coach founders and CEOs at the inflection points where growth, or their own leadership style, has become the friction. Most clients come by referral.
If you’re a senior executive rather than an owner, start here instead.
For the organizational side of a transition, see leading change.
The Decisions Only You Can Make.
A Common Starting Point.
A founder has been circling the same decision for months: an early executive, loyal since the first year, who the company has outgrown. Every framework says what to do. None of them account for the history, the guilt, or what the rest of the team will read into it. That’s the kind of decision we work on, not because it’s complicated on paper, but because it’s hard in real life.
From experience, not theory.
There’s a difference between a coach who has studied leadership and one who has lived it. I’ve made payroll when it was tight, sat with the weight of the final call, and handed my own company to a successor. When your gut and your data disagree, or when the right move costs you something personal, you want a thinking partner who has paid those prices, not one who has read about them.
When the work gets bigger.
One-on-one coaching is often where the relationship starts, but the issues that surface don’t always stay with the individual. Sometimes the business is moving faster than the team: growth, a strategic shift, or an AI implementation exposes problems no strategy document solves on its own. Decisions slow down, communication gets harder, and people struggle with what the change means for their role, competence, or identity. When that happens, I work directly with the leadership team, or alongside an implementation partner, to surface what’s actually happening and help the organization move through it.
Sometimes the change is more personal: stepping up, stepping back, or stepping away entirely. I’ve been through my own exit, and I know what it feels like to hand something over that you poured yourself into. These moments are rarely just tactical. They change how you see yourself and how you relate to what you’ve built. The work becomes making the transition deliberately, honoring what you built while creating room for what comes next.
How the coaching works.
We meet twice a month, one on one. Between sessions, you have access to me when something can’t wait, because the decisions that define a company rarely schedule themselves. A monthly retainer, no long-term contracts. Sessions happen in person where geography allows and online everywhere else, and the relationship can expand into team or transition work when the moment calls for it.
If you’re at a threshold and would rather not cross it alone, let’s talk.
Frequently Asked Questions.
How is founder coaching different from executive coaching?
An executive operates inside someone else’s structure; a founder is the structure. Ownership changes everything: the board answers to you, and you’re the one who has to answer for it. Your identity and the company’s are tangled, and there’s no one above you to absorb the final call. This work is built for that.
Do you work with co-founders together?
Yes, especially when dealing with co-founder conflict or partnership disputes. Co-founder sessions run alongside or instead of individual ones, depending on what the situation needs. I’ve helped many founders navigate business partner disputes and founder disputes.
Can you help me think through succession or stepping back?
Yes. I’ve been through a founder transition from the inside, and it’s some of the most important work I do. This often involves partnership dispute resolution and planning for the future, both for the company and for the founder.
I've never worked with a coach. How do we start?
With a conversation, not a contract. We talk about what’s actually going on, and you’ll know quickly whether it’s useful. If it is, we start; if not, no harm done. I also offer specific CEO coaching for startups if that’s your stage.
What happens between sessions?
You reach out when something can’t wait: a board meeting tomorrow, an offer on the table, or a co-founder conflict that’s escalating. The retainer covers that access, because timing is often what makes these decisions hard.