I talk to a lot of people about building businesses around content. Ashley Hildebrand is one of the few who can tell you exactly where the money gets lost. She's a launch and funnel strategist who works with creators from 100K to 20M+ followers, and she's seen what happens when massive audiences try to launch products without the right systems in place. Spoiler: it usually doesn't go well.

In the latest Creator Diaries interview, we got into the launch process she uses with clients, why she's rebuilt her own business around just three productized offers, and a mantra that I think applies to every creator trying to sell something: let people say no for themselves.

Our full conversation is below, edited lightly for clarity and conciseness 🙂

-Taylor

Q: To start, could you give us an overview of your work and how you got to where you are now?

A: Right now, I run a launch and funnel agency, and I work with fairly large creators—anywhere from 100k to a million-plus in audience size. I help them build out their funnels and launch their digital products, which includes memberships, courses, communities, apps, and that sort of thing.

I’ve been fortunate to work with some really cool people, like Colin and Samir, Adrian Perr, and Shan Boodram. A lot of the biggest names on your "For You" page, I’ve probably worked with them in some capacity. Most of that work, I will admit, has been done through Rare Days, the agency that I was previously at. I owe a ton of my success to Rare Days. They’re really cool, and I’ll always be tooting their horn because they do just the coolest work in the industry—web, design, branding, and building out the digital products themselves.

My journey here was a bit different. I started in this industry almost a decade ago, kind of side-hustling before kids and life and dogs and everything. For a long time, my main job was in emergency coordination for local government—literally fires, floods, earthquakes. It might seem very different, but it's actually very marketing-esque. It’s about selling a message and banging your drum to get people to buy into the message.

I started as a social media manager, but that turned more into social media marketing because I realized the clients I was working with didn't just need more content, visibility, or likes. They needed systems. They needed marketing. That was my push into digital marketing.

I became obsessed with launch strategy: How do we bring a product into the world? What is a funnel? How do we take the attention and likes on Instagram and convert them into cash?

I started talking about this more on socials and was working on building out a done-for-you type of digital product where people could plug-and-play for their own creator businesses. That’s when my work crossed paths with the team at Rare Days. They brought me in-house to build out the marketing services arm of their agency. We would build these amazing products for creators, but then they’d have the product in hand and no idea how to get it out into the world. A lot of creators think that eyeballs turn into sales, which they do not. You need systems in place.

That brings us to now. I’ve since left Rare Days and am essentially taking what I did with them in-house, back out of house. I now focus on launch strategy and execution, building evergreen funnels and conducting creator audits to find where there are drop-offs and opportunities for more conversion. People talk about being a fractional CMO, but I act more like a creator CMO that steps in and does that work.

Q: You mentioned that gap between having a big audience and actually selling something. Could you tell us more about what that looks like and what advice you have for creators trying to navigate it?

A: We could honestly do a whole series on this! One that really sticks with me was a creator with over 20 million followers across platforms. Huge audience. Incredible reach. And he was genuinely excited about launching a digital product. He had invested heavily in it; strong six figures and hundreds of hours building it out. The issue wasn’t quality or effort. It was that some of the foundational validation steps hadn’t happened before the build.

When I stepped in, I realized there hadn’t been much audience research done upfront. He hadn’t really pressure-tested demand, pricing, or whether this specific offer was something the audience was actively asking for. Once we dug in, we discovered a large portion of his audience skewed much younger than expected — 13 to 15-year-olds without purchasing power; they needed their parent credit cards to buy.

And then there was the buyer readiness. His audience had been getting free educational content for years, and there hadn’t been consistent email nurturing or conditioning around paid offers. So when he launched, it wasn’t that the product was bad. It just wasn’t aligned, validated, or warmed up properly. After all that investment, the launch did just under $2,000 in sales.

The big lesson is: a large audience doesn’t automatically mean sales. You still have to great offer that your audience actually needs. And biggest of all, warm people up before you build. Otherwise you’re building on vibes instead of evidence.This story highlights the core challenge. I see two kinds of creators out there. 

The mental switch from knowledge creator to business owner is very difficult. Their audiences have different expectations. The stuff that got them a million followers is not the stuff that's going to sell a million dollars worth of product.

For the business-minded creators, they often get in their own way. They’re doing enough that there are too many things broken, so I have to go in and fix their systems.

They might be learning from the wrong types of people, like Alex Hormozi, Daniel Priestley, Codie Sanchez, or Jenna Kutcher. They're playing on a different playing field. What works for them is like trying to learn soccer from Messi—you're just not on the same level yet. There’s a lot of good stuff there, but it won’t apply in the same way.

Q: There are so many opinions on what products work—people say courses are dead, for example. How do you evaluate what product or format will be valuable to a specific audience?

A: Product strategy usually comes beforewe start to build out a launch, and the people I work with typically already have signals for what’s working. But I’ve seen it all, and it all works at different times.

Courses will never go away. I am curious where memberships will go, because it feels like streaming services—at what point do you have too many? I almost feel like those could be shortened into time-based cohorts or clubs, just like you only go to college for four years. A lot of people will shit on cohorts because they think it's just a course repackaged, but it really depends on the audience.

I don't care too much about what's working and what's not. I care about how it's being delivered. Everything evolves. We used to have iPods, and now it's all on our phones—the music product never went away, it was just refined. For a product to work, it comes down to the trust in the creator and giving people a clear picture of what they're getting inside. I think people say ‘courses are dead’ because the market was flooded with them during the pandemic. Trust was eroded because a $300 product could be the same as a $15 one.

It really depends on the audience and how they consume content. If your audience is mostly moms, they probably don't have time for a four-hour course, but they might love a paid podcast.

Dr. Becky at Good Inside has an app for moms with three-minute TikTok-style shorts because that's how they consume content. But when I was working with Adrian Per, a video content creator, his product needed to be a course because that's how his audience wanted to learn from him and see how he makes video editing decisions. There's no right or wrong answer, only trends that we can take as feedback.

Q: For that more business-minded creator, could you walk us through the launch process you use?

A: Launching is extremely simple, and then once you get good at the simple stuff, it becomes extremely complex because you can iterate on every single touchpoint, from the title of a page to the slug in your URL. But when it comes down to it, launching is about getting visibility and then capturing those eyeballs.

The biggest thing of all is that they understand the transformation it will give them. They need a great picture of who they are before they purchase and who they are going to become after. Are they going to be hotter? A better knitter? Will they read faster? It’s not about getting four videos and community access—those are nice benefits. It’s about who they will become.

Q: What advice do you have for someone who feels uncomfortable with selling? It can make you want to crawl out of my skin.

A: I think you were probably raised like me. I was raised that you do not ask; you wait until you’re given permission.

But you create permission in a launch; if people have said "hell yes" at every step of your funnel, they have invited you in. They’ve invited you into their inbox. They want to know what you have to say. They just need an invitation.

This is the number one thing I hear. People feel annoying. They think, “If they wanted to buy, they would have already.” But that's not true. In a launch, you see this huge dip in sales at the beginning, and then it’ll be flat for a while. That’s where people shut up. They stop sending emails. But that messy middle part is where people are making their decision. You cannot be quiet. Then there’s another blip at the very end because you’ve continued to show up. You have to sit in that discomfort.

My personal and professional mantra is: Let people say no for themselves. Don't answer for them. They're a big boy or a big girl. It's not your job to be quiet; it's your job to be consistent and clear. And honestly, you need to have the audacity. You have to accept that you're going to feel annoying to yourself, but nobody cares about you as much as you think. They need to see your face a ton of times. If they're judging you, they're a hater, not a fan, and they weren't going to buy anyway. Good riddance.

Q: How does focusing on that transformation make the sale easier?

A: If you're doing your job right, you've already made it clear that you genuinely want this transformation for the person. It's like when you talk to your best friend. You want the best for her. Some of those things you might say might be hard to hear, like “I don’t like your boyfriend,” and you’ll find a million different ways to say it to her in ways that are loving and that she’ll hear, because it comes from a place of trust. It’s about knowing your audience better than you know yourself and speaking to their needs.

When you say, “Hey, I want you to spend $1,000 on this, this is your last chance to become this new person three months from now,” it’s because you really want that for them. It's different from a tacky, Hormozi-esque tactic of “if you buy this now, then you're going to have 50 free other things.” With that, you’re speaking to their lizard brain. With transformation, you’re speaking to their upper-level, more evolved brain.

Q: You’re running your own business again. What has that transition felt like, and how are you thinking about building your personal brand?

A: It's very top-of-mind. I actually started Emboldyn 4.5 years ago, but put things on pause when I was in-house at the agency. But the business I’m running now is a completely different one then I launched in 2021. I had never worked in a large agency before, and I learned a ton at Rare Days—I got to launch everything faster and work alongside developers and brand designers. I have way more perspective now. Also, when I originally started, I didn't have kids; I had my full control over my hours in a day. Now I have two kids, and how I want to operate is very different.

I was inspired by the book Built to Sell, not because I necessarily want to sell my business, but because it motivated me to productize my services.

Previously, I was building everything a la carte. I said yes to everything—personal brand strategy, ghostwriting, content strategy, social media management. I was spinning my wheels. Scope just blew up. I'd open my computer and have no idea what was a priority. It was the age-old story of trading time for money. I’d quote for 10-15 hours, and it would end up taking me 40. I’d think I was making $100 an hour, but I was really making $25.

I knew I was done with that. Now, I’ve decided to productize my services, which means saying no to a lot of things. I’ve settled on three products: a creator business audit, launch and execution, and building out full funnels.

These are based on what I see my ideal clients need needs and what I know I can do well in a containerized, scalable way so I can hire a team. This frees me up to build my own personal brand, launch my own newsletter, and eat my own dog food.

This means I’ve stopped kissing a lot of frogs; I’m saying no to so many frogs to get my prince clients. For every yes I’m saying, I’m saying 5 to 10 no’s.

Q: What are the qualities of the dream client you're looking for now?

A: My prince client, or princess client, is someone who's ready to ship fast and build big, iterate really quickly, and isn’t afraid of getting uncomfortable. They have a genuine, authentic relationship with their audience and a really cool product that actually helps people. I think one of the most disruptable industries is education, so anyone breaking the mold of how we learn and grow is really cool. Dr. Becky at Good Inside is a huge example. She has her own in-house team, but she’s a dream client just because of the product she has and how it’s changing lives.

On the smaller side, the clients I work with don't need to be of that caliber. They just need an audience that's already engaged, probably a newsletter where they're connecting regularly, and some signals or proof points that their product is already working and is ready to be taken to the moon, without getting in their own way.

Q: Finally, the question everyone always wants to know: what about audience size? How many followers do you need?

A: It depends on what you're selling and to whom. If you're selling a $300 to $800 product and you want it to be your full-time gig, you probably need an audience of 10,000 or larger.

If you start to do the math—and oh my gosh, I’m so bad at math—say you have 10,000 followers and you capture 40% on an email list. That’s a 4,000 email list. Maybe 20% of them sign up for a workshop, so that’s roughly 800 highly engaged people. Of those, maybe 3-5% purchase.

So, being conservative, on a 10,000-person audience, you might get 25 to 40 people purchasing a $500 product. That’s a $20,000 launch.

If you have a low-ticket product, you need a much larger audience to get the scale you need, unless you have a killer product that everyone is drooling to purchase. So if you don't have the audience size, step number one is growing your audience, and that's where a lot of people get stuck. You need to be creating high-value content, nailing DM automation (that’s a whole other convo), collecting emails, nurturing audiences, and having a a strong funnel.

But you can absolutely start selling with a much smaller audience to get your reps in. You can launch with a 1000-person audience and have a really successful launch. If you're selling a digital product, you need to build the right audience. If you're doing services, it's different, but it's much easier if you have at least 1,000 people who are talking about you, saying your name in the right rooms, and sharing your stuff.

If you’ve made it this far, you’re probably as impressed as I was to listen to all of Ashley’s wisdom. She’s had a front row seat to some of the biggest creator founder brands in the Creator Economy — and has a clear understanding of how you actually take that audience and attention and turn it into money. Which is why we’re all here isn’t it?!

If you want to follow along with her work:

That’s all for now! See you next week 👋