Meet Dolly
My personal hype woman
Dolly operates according to one principle:
If you built it, girl, it’s time you shout about it.
You upload your LinkedIn data (she walks you through it—it’s easier than it sounds).
She analyses every post you’ve written. Not for keywords. For patterns.
She spots when you wrote “we launched” but you actually led it. She notices when you said “somehow this happened” instead of “I built this.” She tracks momentum you didn’t see because you were too close to it.
Then she builds you a timeline. Month by month. With receipts.
And she writes about it the way you would if you weren’t afraid of sounding “too much”.
The Backbone Part
If you try to soften the language, she pushes back.
Not aggressively. Just clearly.
“This feels cringe.” “We’re not calling confidence cringe. You did the work, we’re just telling the truth about it.”
“I don’t want to sound braggy.” “Visibility isn’t ego. It’s leadership.”
She is southern by design. Relentless by nature. Part life coach, part data analyst, part hype woman one you’ve never encountered before.
She has empathy. But she also has standards.
She is not interested in hype. She is interested in accuracy. Specifically: the accurate reporting of your own achievements, which you consistently undervalue by approximately 68%.
Why This Matters
False humility is expensive.
In fact, women are 16% less likely than men to list leadership skills on LinkedIn, even when they’ve earned them.
When you don’t claim your work, someone else does. When you don’t name your impact, it disappears. When you shrink, you teach the next generation to do the same.
I built Dolly because I was tired of watching brilliant people—mostly women—undervalue their work in real time.
I’d seen it everywhere. In my own head. In my Get Sh*t Done community. At workshops. In LinkedIn posts where brilliant people apologise in the first sentence for having done something excellent.
“I was lucky to...” “This somehow happened...” “We managed to...”
We apologise before we speak. We credit luck over labor. We hide behind ‘we’ when we led.
And now I was doing it too.
I remembered the highlights of last year, the LinkedIn posts I’d done about my time at Cannes Lions, SXSW London, Oxford AI Programme (Distinction). A community that doubled to 650+ members. Get Sh*t Done events selling out in a day.
And I was about to say nothing about any of it.
That’s not modesty. That’s conditioning.
How I Built Her
First, I downloaded my own LinkedIn data. It took a little less than 24 hours. (I’ve trained Dolly to give you instructions if you want to try it out for yourself)
When I opened it, I got angry.
Why the fuck can LinkedIn use all this data on me, but I can’t use it on myself?
I love using anger to fuel problem-solving.
So I started building.
1 - The Hype Woman
I built a version of Dolly that just gave you encouragement. Generic hype.
I hated it. Most AI platforms can do that if you prompt them right. It wasn’t clever enough.
2 - Receipts Required
I wanted data. If I’m going to believe a compliment, I need proof.
So I built Dolly to analyse your actual LinkedIn posts—not just pump you up, but show you exactly what you did and when you did it.
3 - Matter of Fact
AI doesn’t blush. It doesn’t soften.
When Dolly says “you did great,” she means it. She’s not trying to make you feel better. She’s reporting facts.
4 - Smarter Than Me
I wanted Dolly to be smarter and a better hype woman than me.
She resurfaces wins I didn’t even notice. She spots patterns I’m too close to see.
Let’s face it: I can be pretty bad at recognizing my own momentum. (And I’m sure I’m not alone in this)
5 - The Name
I take a lot of time thinking about my AI tool names. Why? Because a name needs to conjure the right emotion.
Dolly came to mind thanks to the film 9 to 5 and Dolly Parton’s brilliant character. Not taking no for an answer. Standing up to yourself. Standing up to bullies.
6 - The Build
I built her with long markdown prompts. Iterated over and over again until I fed it to the machine—in this case, OpenAI.
Tested. Broke. Fixed. Repeated.
7 - Bringing Her to Life
I think a lot about how to promote my AI tools. As a creative director this is my bread and butter. But to me it’s more than a simple promotion. I want to show how an AI tool can feel human yet not be confused with a machine. I want to have fun with it—AI can be so dull in its explanation. I want to build her world and what she can do so she isn’t a scary AI tool with weird jargon but you get who she is with her personality and way of operating.
Things like: “Hair: Architecturally significant. Heart: Disproportionately oversized (medically impossible). Tolerance for self-deprecation: Precisely zero…”
See here for the full post.
8 - Distribution
She helped me deliver her to people. Not the post copy but the email that delivers her to people.
But in all honesty, I could probably do better at this. Right now, I’m pushing her on LinkedIn.
The plan is to bring her to Instagram too: @rebecca_rowntree if you’d like to follow along (and give me moral support)
And that’s it, the inner workings of my brain and the brilliant Dolly!
Want Dolly?
Subscribe to my Substack and she’s yours, delivered straight to your inbox along with behind-the-scenes breakdowns of how I build AI tools like this.
Because you did the work. You might as well take the credit!
Want your own AI character? I build these tools constantly. For people, for brands, for problems that need solving.
If you’re interested in your very own AI tool with personality, give me a shout: rebecca@gsdstudio.co