A One-Year Creative Direction Retainer for Visionary Founders
Meg Holiday, Brand Coach & Creative Director
You have already built something real. The revenue is there, the clients are there, the proof is there. What's left is the version of your brand that finally looks like where you're going, not where you started.
There is one room in 2027 built for exactly this.
Speakeasy is not a mastermind. It is not a membership. It is a year with me at your side, on retainer, as your Brand Coach and Creative Director, so that every piece of your brand — from your welcome packet to your sales pages to the photograph behind you on a launch day — is built with the same hand and the same standard, all year long.
Every month for a full year, we sit down together for a two-hour deep dive, mapping your brand and your business side by side, season by season. Not a check-in — a real working session where the creative and the strategy get built at the same table, so nothing about your brand is ever developed in isolation from where your business is actually headed.
Two private 1:1 calls a month, and they're yours to use however you need them — back to back before a launch, spread across the month, or saved for the moment you're stuck. Add direct 1:1 texting access on top of that, and what you have is a Creative Director on call, not on a schedule. This is the only room in 2027 with this level of access to me, full stop.
This alone is massive. Two full Brand Residencies in a single year — one in Cleveland, one in any city you choose across North America or Europe. Each is an all-inclusive full day of co-creation: two nights hotel, studio rentals, hair and makeup, and all props and styling as desired, unless otherwise specified. Nothing is left for you to plan or pay for separately. Every detail is mapped out together in advance, so what we create supports your upcoming launches directly instead of sitting as generic content.
You walk away from each with 300 edited images and 20 video clips — 600 images and 40 video clips for the year, enough original content to carry every sales page, every program PDF, every newsletter, and months of social without ever reaching for a stock photo. If Cleveland isn't doable for travel or scheduling, that Residency can be hosted in another city of your choice instead, for an additional $5,000 Abroad Access investment.
$25,000 valueFor up to six programs in 2027, we co-create the branding and offer details together, then I build out a sales page and a program slide deck or PDF for each one, in partnership with Claude AI, so the language, design, and offer positioning all sound and look like they came from the same brand. This is the program-level creative and copy, not ongoing social content — and it's fully yours: editable, reusable, built to convey the most elevated brand identity.
$12,000 value
Every class I teach in 2027 — masterminds, mini programs, the Program Portal — at any price point, is yours with no separate enrollment and no upsell. That includes standing access to the Holiday House Mastermind's weekly hot seats, whenever you want to bring something to the room.
$30,000+ valueYour room is fully covered at the annual Holiday House Mastermind retreat, starting with NYC this January, with the 2027 location still being finalized. Past retreats have taken the room to Santa Monica, South Beach, Joshua Tree, and The Hamptons. The only thing left for you to book is your flight.
$5,000 valueEvery member joins me for UN27, my annual conference, with a VIP ticket that includes your room, front row access, and a luxury gift bag waiting for you when you arrive. No separate ticket to buy, no scrambling for a seat — you're already in the room.
$5,000 value
A spa experience local to you, to mark the beginning.
A gift card to take someone you love to a five-star dinner.
A luxury jewelry piece, made to be worn for years after this year is over.
Speakeasy is built for founders who are already proving what's possible and are ready for their brand to catch up to their ambition.
If this is yours, you already know.
"The next step isn't a decision to make from scratch — it's a decision to stop waiting on the version of your brand that's already waiting on you."
Plus 200 custom, branded Instagram story sets for your first quarter, if paid in full.
Each Residency is led by me, in person, over a full day of shooting, so your images and video carry one consistent creative direction across the whole year. If you have an existing photographer for other work, that's separate — the Residencies are the two dedicated days built specifically for this container.
You can certainly choose to do one and forgo the other, and swap it out for a longer residency or brand support of another kind, such as media assets, a softcover Brand Book, or office styling for your Zoom backdrops.
Life happens. Calls can be rescheduled with reasonable notice — the retainer is built around consistent monthly access, not a rigid calendar.
The Holiday House retreat is a shared experience with the rest of the Mastermind room, so it's built around the group. If you'd like to bring a guest, reach out once the location is set and we'll talk through what's possible.
Apply anyway. The number is a guide for the level of business this room is built to support, not a hard line, and every application is reviewed personally.
Speakeasy is for visionary founders across creative and service businesses, not coaches exclusively. What matters is that you're ready for a brand that matches the size of what you're building.
Yes. I'm your go-to for keeping your brand consistent, unique, and high quality across every part of your company's World. When you create campaigns, sales pages, or events outside of our work together, I just ask that we work together so the supplemental work supports our main brand objectives, with no discrepancy in continuity.
The Deep Dives, Residencies, and full class access are built around the calendar year. If you join mid-year, we'll map out together how the remaining months, sessions, and Residencies fit your start date.
If you already know this is yours, the next step is a conversation, not a checkout page. Speakeasy is by interview, so I can hear where you're headed and we can both decide if this is the right creative fit.
Request Your InterviewA few quick questions, no essays. Speakeasy is by interview only — I want to hear where your brand and business are headed before we decide together if this is the right creative fit for the year.
Received.
Thank you for applying for an interview for Speakeasy. I review every application personally and will follow up to schedule a time for us to talk.