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About
Most founders don’t need more advice. They need someone who’s been there.
Most founders who reach out know something needs to change. The company is growing, the team is bigger, the board is more involved and somewhere in that transition, the way you used to operate stops working as well as it did.
You are slower on decisions. You are in more meetings and closer to fewer things that matter.You are managing people who need a different version of you than the one that got the company here.
That gap between the founder who built the product and the CEO who has to scale the organization is where most of the hard work happens. It is also where most founders go without real support.
I have been in that gap. I know what it costs to try to navigate it alone.
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I’ve Been In Your Seat
I founded Stitcher, the podcast platform acquired by SiriusXM for $325 million, and ran it for eight years. Before closing our first round, I was rejected by 90 venture capital firms. I kept a spreadsheet. Benchmark eventually said yes. So did NEA. We raised four rounds in total.
Those eight years included flat growth, board conflict, three moments where the business nearly died, multiple pivots, and a full acquisition process. I made every expensive mistake a startup CEO can make - hired too fast, scaled before we had product-market fit, avoided hard decisions longer than I should have, and carried too much alone for too long.
Before Stitcher, I was VP of Sales on the founding team at StubHub, which was acquired by eBay in 2007. After Stitcher, I spent eight years at Amazon Web Services - first running BD for YCombinator startups, then as Head of Early Stage Startup Business Development - working directly with hundreds of founders across every stage and vertical. I have invested in and advised more than 30 startups.
I started coaching CEOs on the side in 2019. By 2025 it was my full-time job.
I now coach more than 20 venture-backed CEOs at a time. My clients have raised from YCombinator, Andreessen Horowitz, Sequoia, Khosla Ventures and Lightspeed. The aggregate enterprise value of their companies exceeds $3.5 billion. Most stay for years, not months.
How I Work
My approach is direct and structured. I draw on Mochary Method, Conscious Leadership Group, Co-Active coaching, 10X CEO, Nonviolent Communication and Five Dysfunctions of a Team - but I do not follow any one methodology. I use what fits the person in front of me.
I will push back on the stories you are telling yourself. I will help you name the decision you have been avoiding and hold you accountable to it. I bring my network when it is useful. You should see value immediately, in every session.
The topics that come up most: focus and prioritization, difficult people decisions, co-founder dynamics, board management, fundraising psychology, decision-making under uncertainty, and avoiding burnout without losing drive. Nothing is off limits.
Who This Is For
This is for VC-backed founder CEOs between Seed and Series C with a team of five or more, a product in market and real traction. You are past the question of whether this works. You are into the harder question of how to scale it and yourself without breaking things along the way.
The founders who get the most out of working together want direct feedback and are ready to act on it. They are not looking for validation. They are looking for a thinking partner who has been in the seat and will tell them the truth.
If you are waiting until things are bad enough to justify a coach, you are waiting too long. The founders who engage early have a much easier time when the hard moments arrive because the relationship and the habits are already in place.
What the Engagement Looks Like
Biweekly sessions, 60 to 80 minutes each. Unlimited support between sessions - text, email, or a quick call when something cannot wait. Month-to-month at $5,000 per month, with no long-term commitment. You should see value immediately. Most clients continue for years.
Before we begin, I conduct stakeholder interviews with members of your team, your board, and your investors. The goal is to understand how you are being perceived from the outside before working on how you are operating from the inside.
What changes over time: faster decisions, quicker recovery from setbacks, cleaner communication, and a team that feels more aligned. These improvements compound because they affect everything downstream.
The best investors already understand this. Garry Tan, President of Y Combinator, has spoken publicly about the value of founder development. Felicis has a Founder Pledge where one percent of every round goes directly to it. The founder is the most leveraged asset in the company and investing in the founder compounds.
Want to explore working together?
