How StartupCoaching Works
A high-trust partnership built for results.
Startup coaching isn't a course. It's not theory. It's not therapy. It's tactical pressure, sharp feedback, and real momentum, built around your startup and your reality.
"This isn't a course. It's not a cohort. It's not a mastermind. It's not therapy. It's a high-trust, high-intensity, results-driven partnership. Built around you."
You're not hiring a "coach." You're bringing on a partner. Someone who's exited companies, coached hundreds of founders, and lives inside the startup grind every single day. Someone you text at 11PM. Someone who will pressure test your assumptions, challenge your instincts, and help you win.
"Coaching isn't about teaching. It's about pressure. Perspective. Pattern recognition. We're partners in the journey. We're texting. We're celebrating. Sometimes we're crying. But we're always moving forward."
The Process
Five phases. Each one matters. Each one builds on the last.
PHASE ONE
The Intro Call
It's your call. Your time. To focus on what you want. There's no economic incentive to this call, it's not sales. It's designed to have three core outcomes:
Value First
You leave with more than what you expected.
Competence
You confirm I know what I'm talking about.
Chemistry
Do you like how I think, interpret, and how we spar together?
This is such a deep and personal relationship. We'll speak often, we'll text, I'll get to know your family, your history, and you to mine. The most important thing for both of us: Will I be excited to get on a call with this person? It might not always be a great call, shit day, shit weather, shit work, but that's okay, because while you might hate the contents of the call, you'll love the call itself.
PHASE TWO
The Second Date
We both pretended to be on our best behavior on our first date. The second one, we're both more relaxed (mainly you) and we do a functional thing.
From Exploration to Action
The first call was chaos and exploration, getting to see how you think and map and ideate. This call is about doing some work together.
Seeing Both Sides
We address all the questions we had from the last call and start digging into the real work. This helps us see both sides of each other.
PHASE THREE
Go / No Go
I am not coin operated. If it's not the right time, if there's better use of your funds, if I'm not the right guy for you, whatever the reason, I'll tell you first. We'll feel it, I'll say it.
If we don't work together, I'm still an ally, and I'll encourage you to stay connected. I'll reach out every now and again to check in. But essentially, you're kind of stuck with me. The only question is if I'll be paid for it.
PHASE FOUR
The Format of an Engagement
In general, we'll have 90 minutes of scheduled talk time, same time every week, on the books. Life changes, things happen, coffee is important, but in general, this is our time.
Beyond Status Updates
The call is not to catch me up on your week. You do that in Slack and text throughout the week with as much async communication as needed.
Flexible Touchpoints
Depending on the project, the week, or the vibe, we often have a quick connect at the other end of the week, usually focused on the thing we're working on.
It's casual. We want to be on the call. We both know life exists, a kid's ballet, vacation, it's not about minutes, it's about momentum and results, period. What do we do together? Whatever we have to do to achieve our small steps, long vision plan. Period.
PHASE FIVE
Investment & Equity
You're paying between $5,000 and $11,000 a month. Retainer. Cancel anytime, no scope.
Results-Based Engagement
The retainer gets paid, even when I go away for a week, because by then, we understand it's a results engagement and not a debit and credit system.
Equity Consideration
I don't ask for equity upfront. But if we're still running together at Month 13 - if I've earned it - a 1.5% fully vested kicker triggers.
If you don't like that, cancel in month 12. But if I have not accelerated your business and brought insane accretive value, then you would have cancelled the relationship long before that.
What Makes This Different
It's not about information. You already have that. It's not about motivation. You don't need hype.
Pressure that drives action
Not comfortable conversations. Real pressure that creates momentum.
Perspective that sharpens judgment
Pattern recognition from hundreds of founders and multiple exits.
Partnership that multiplies momentum
A co-builder who's been there, failed, won, and still shows up.
This is war-time startup building. With structure. With chaos. With a co-builder who's been there, failed, won, and still shows up.
