olivia_rossi

Advisory

Strategic advisor for creators & founders.

I work with creators, founders, and independent operators who have a lot of ideas and no clear structure holding them together. My job is to help you figure out what to build, in what order, and to keep you moving on it.

Who I am.

Hey! It's great to meet you. I'm Olivia — a former engineer, product manager, and influencer business manager, now an advisor to creative businesses.

After working my whole life as a full-timer, in 2023 I quit to do my own thing. That turned into three-plus years of working closely with content creators and founders, and building the business side of creative work: positioning, offers, content, monetization, and the roadmap for what comes next. I've advised more than 10 creators this way, built awesome live experiences (including 3 sold-out shows), and I still keep a small roster I meet with whenever they need me.

What you see is what you get. I'm blunt, I don't sugarcoat, I'm not a coach and I'm not a therapist. I'm someone who has a lot of ideas, has worked with a lot of people building things from scratch, and truly loves the puzzle of it.

What I do.

Most people come to me with the same knot. They can see where they want to go, they have about eight ideas about how to get there, and they can't tell which one to start with. We sit down and untangle it together.

Every session, you bring the mess. We workshop it, and you walk away with clear action items and a sense of what to prioritize next. Between sessions, I hold you to it. When you bring me an idea, I'll push on it, and I'll bring you what I've actually seen work and not work with other people building similar things. It's collaborative, it's honest, and you never leave without a next step.

2 ways to work with me.

1

Book as you go.

Buy a pack of sessions up front, then book them whenever you need me over the next few months. Some weeks you might need me three times, then not again for a month. Good when you want flexibility and no ongoing commitment.

2

Retainer.

More structure and accountability. Two sessions a month at a set rhythm, so momentum doesn't break. Three-month minimum, cancel anytime after. Good when you know you'll keep showing up and you want someone holding you to it.

Pricing.

What every package includes

The notes from every session, written up so you're not scrambling to remember what we said
Clear action items after each call, plus accountability to actually move on them
A real plan and a way forward, not just talk
Support between sessions — text or email anytime, answered within 48 business hours (usually faster)

4-pack

4 × 60 min

$700

$175 each, $100 off the single rate. Paid up front. Use within 3 months.

8-pack

8 × 60 min · most booked

$1,300

$162.50 each, $300 off. Pay in full, or split into two payments of $650. Use within 12 months.

Biweekly retainer

2 sessions/month, ongoing

$400/mo

Set rhythm, accountability built in. Invoiced on the 1st. Three-month minimum, cancel anytime after.

For Canadian clients, an additional sales tax applies to the total (14.975%).

What it feels like to work with me.

When I met Olivia, I had an idea of a project I'd been wanting to create for over 5 years [...] Fast forward a few months into our collaboration, and I FINALLY have a brand, social media content, and a roadmap for the future.

Rachel A.

Just want to say thank you for making everything make sense in my brain. I'm very grateful for all the time you've invested in this so far.

Shaping Sarah

Working with Olivia has been an absolute pleasure. Her dedication, organizational skills, and unwavering commitment to getting the job done are truly unparalleled.

Laetitia K.

She told me if she got involved my project would move. She was right [...] incredibly organized, focused, and direct. In working with Olivia, I've developed a new standard with regard to my own work ethic.

Khadija M.

Getting started.

If any of this sounds like what you need, the fastest way to find out if we're a fit is a 15-minute discovery call.

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