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Coaching Methodology
A Coach Who's Been in the Seat
I was the founder and first CEO of Stitcher, the podcast platform acquired by SiriusXM for $325 million. Before closing our first round of funding, I was rejected by 90 venture capital firms. I was the first sales hire at StubHub before its acquisition by eBay, and I led the Early Stage Startupteam at Amazon Web Services, working directly with hundreds of founders across every stage.
I have invested in and advised more than 30 startups. I now coach approximately 20 CEO clients at a time - venture-backed founders between Seed and Series C, backed by firms like YCombinator, Andreessen Horowitz, Sequoia, Khosla Ventures, and Lightspeed. The aggregate enterprise value of companies led by my clients exceeds $3.5 billion. I have both lived through the hardest parts of building a company and watched them up close from the outside. That combination is what makes this coaching different from working with someone who has only observed founders, or only been one.
Who I Work With
- I work with venture-backed startup CEOs between Seed and Series C.
- You have a team of 5 or more people with a product in market and significant traction.
- You’re transitioning from hands-on builder to leader of a scaling organization.
How an Engagement Works
- Stakeholder interviews - I interview 6-8 people who know you best professionally before we begin. Direct reports, board members, co-founders. I'm looking for the patterns everyone around you sees that you don't.
- Meeting observations - I observe 1-2 of your leadership meetings to see how you show up in practice.
- Biweekly sessions - 60-80 minutes each. We start with what's most urgent, go deep, and leave with clear action items.
- Accountability - I hold you to what you commit to. Every session opens with a review of what you agreed to do.
- Between-session support - Unlimited access via text, voice notes or calls for the moments that can't wait.
Frameworks I Draw On
Here is what I draw on and why.
Mochary Method Focuses on eliminating the fear and anger that drive most dysfunctional leadership behavior. Gives CEOs concrete tools for running meetings, making decisions, and giving feedback that create clarity instead of confusion. I use it most in the early stages of an engagement when we are mapping how you currently operate and where the biggest friction points are.
Conscious Leadership Group (CLG) Built around the distinction between being above the line- curious and open - and below the line - defensive and reactive. Most leadership problems in startups happen below the line. This framework gives you a language for noticing when you are there and tools for returning to a more effective state faster.
Co-Active Coaching One of the most widely used professional coaching models in the world. Built on the principle that clients are naturally resourceful and whole - the goal is not to fix you but to help you access what you already know. I use it to structure the coaching conversation itself, balancing challenge with support.
10X CEO Focuses on the mindset shifts required to lead at the next level of scale. Helps founders move from doing to leading, from solving to enabling, and from urgent to strategic.Particularly useful with Series A and B founders who are managing a growing team for the first time.
Nonviolent Communication (NVC) A communication framework that helps people express what they need and hear what others need without triggering defensiveness. For founders navigating co-founder tension, difficult board conversations, or team conflict, it provides a practical structure for the conversations that feel hardest.
Five Dysfunctions of a Team Identifies the five patterns that reliably cause leadership teams to underperform: absence of trust, fear of conflict, lack of commitment, avoidance of accountability, and inattention to results. I use it as a diagnostic when a founder's challenge is about team dynamics rather than individual leadership.
I know many frameworks and best practices and choose the ones that will work for you. I don't follow any one methodology.
Outcomes of Working Together
- Shift from reactive to intentional leadership.
- Show up grounded, focused, and energized.
- Build the emotional range to make clear decisions under pressure.
- Upgrade habits, health, and mindset for sustained high performance.
- Communicate clearly, directly, and with influence.
- Empower instead of over-functioning; delegate and elevate.
- Surface and resolve conflict early.
- Build trust with execs, board, and investors.
- Lead in a way your team learns from and amplifies.
- Align the company around a clear mission and priorities.
- Build systems so execution scales without you doing it all.
- Create a culture of ownership, urgency, and accountability.
- Hire, develop, and - when needed- replace with confidence.
- Prevent “founder bottleneck” and unlock compounding momentum.
Want to explore working together?
