PRIVATE COACHING · BY APPLICATION ONLY
You don't need a financial advisor. You need someone who's already done this. A private coaching engagement led by Sydney Gregory, CFP® — nearly a decade managing $1B+ for ultra-high-net-worth families, now working with a limited number of clients at a time.
You've built the income. What you haven't built is the structure underneath it.
For ten years, that structure is what I built for people who never had to think about their own money — every dollar accounted for, every decision made with precision. The First Dollar exists because that same structure shouldn't require a $10 million net worth to access.
This is where it gets built for you.
Who This is For
Coaching is not self-checkout. It's a relationship, and it starts with an application.
This isn't about how much you have. It's about whether you're ready to actually do the work.
You're a fit if:
- You want your full financial picture handled — not one problem at a time
- You're ready to be honest, consistent, and engaged between sessions
- You want direct access to someone who's operated at the highest level of this work
This isn't for you if you're looking for a template or a quick answer. If that's what you need, The Framework is $97 and yours instantly.
How it Works
- Apply. A short application — this is how I make sure it's the right fit before either of us commits time.
- Hear back within 48 hours. I read and respond to every application myself.
- We begin. Agreement, payment, and your first session — scheduled personally once you're confirmed.
The Two Ways to Work Together
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Foundation
$997 — Four Sessions
Over 6-8 weeks, we build your complete financial foundation — baseline, debt strategy, savings system, goals, risk assessment, mapped and monetized specifically for you. Not a Framework with your name on it. A plan built from your actual numbers.
Available by application. Limited spots per month.
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Ongoing
$247/month — One Session + Direct Access
For clients who want a standing partnership. One session a month to revisit and adjust your plan, plus direct access between sessions when a decision needs a second set of eyes.
A limited number of ongoing spots are open at any time.
Coaching is offered by application only. Spots are limited.
This coaching engagement is educational and coaching in nature. I do not manage investments, provide personalized investment advice, or recommend specific securities — this is strategy, structure, and direct access to someone who's built this before.