Most creators think too small.
They launch a podcast and hope to monetize it with ads. They build a YouTube channel and dream of brand deals.
Michael Bosstick thinks they’re missing the point entirely.
Bosstick is the founder and CEO of Dear Media, the largest female podcast network. His thesis is this: Creators should treat their media properties as a launchpad — where an audience is gathered, attention is funneled, and something much bigger is born.
He walks the walk. This is exactly what he’s done with the podcast Bosstick hosts with his wife Lauryn Bosstick, and it’s what Dear Media helps its 100-plus podcast hosts do as well.
On my Problem Solvers podcast, we talked through five strategic frameworks that Bosstick uses to turn creators into entrepreneurs — and how you can apply them to your own business. Listen here, or read below.
1. The Trojan Horse Approach
Want to launch a podcast? Think of it as your entry point, not your end goal.
For example: When Bosstick and his wife Lauryn started The Skinny Confidential Him & Her Podcast in 2016, they had a bigger vision from day one.
“We didn’t just want to be podcasters,” Bosstick says. “We never even cared about monetizing the podcast for the first two or three years. It was really just a hub to do the other things.”
The podcast became the foundation for Lauren’s lifestyle product line, their investment portfolio, live events, and eventually Dear Media itself — a full creator economy ecosystem.
Here’s what creators often miss, Bosstick says: When you succeed in media, you’re really developing a deep, authentic connection with an audience — and once people trust you, it can be the foundation for a much more robust business.
“When you start talking on a mic, week after week, day after day for long periods of time, you can really have deep conversations and you really start to learn how someone thinks, how they feel,” he says. “It’s one of the only places you can truly get to know creators.”
Your Action Step: Stop thinking about your podcast as a revenue stream. Start thinking about it as a relationship-building machine that can support multiple revenue streams. What products, services, or businesses could you build once you have that audience’s trust?
2. The Upside-Down Triangle Strategy
Here’s where most creators go wrong: They try to appeal to everyone from the start.
“If your strategy is to go wide and reach everyone, you’re going to end up reaching no one,” Bosstick says.
Instead, successful creators follow what he calls the “upside-down triangle” approach: Start with a very specific niche, which will make you relevant to a specific group of people. Build trust with them first, then gradually expand into adjacent topics.
That’s what The Skinny Confidential did. “It started very narrow,” he says. “In our case, it started as building a brand and a business online and taking audience questions. Then over time, we introduced more of our relationship, and we introduced more of guests, and now we’re in so many different categories.”
The show’s topics ping-pong between business, fashion, health, celebrity, and so on — something that cannot be replicated by new shows today.
Your Action Step: Define your niche so specifically that you could describe your ideal listener in one sentence. What’s the most focused version of your expertise? Start there, even if it feels limiting. You can always expand later.
3. Match Your Strengths to Your Platform
Not everyone should be a podcaster. And that’s okay.
“It’s really important to be self-aware of what medium works for you,” Bosstick says. Some people are great talkers and belong on a mic. Others are better writers, and can create huge communities through newsletters. Or they’re building their presence specifically on LinkedIn or TikTok.
Once you identify your medium, he says, you should think several moves ahead: “If I’m going to start on Substack, I already have a book planned two years down the road. I already have a podcast planned off of that. I already have a brand planned.”
Your Action Step: Take an honest inventory of your natural communication strengths. Are you better on video, audio, or in writing? Do you prefer one-on-one conversations or speaking to groups? Pick the medium that feels most natural, then map out how it could evolve into other formats over time.
4. Avoid the “Everything at Once” Trap
Creator businesses are hard. They’re often solo projects that require constant content production, strategy, relationships, and more.
Don’t get overwhelmed, Bosstick warns. Instead, maintain a radical focus on the immediate next step.
“The first question to ask yourself is, and I got this from Tim Ferriss: If this were easy, what would it look like?” he says. “That question alone helps you slow down and go, okay, well what do I actually need to get going?”
He uses YouTube as an example. New creators think they need the best equipment, perfect scripts, and mastery of every technical detail before they start. But the real barrier isn’t technical — it’s psychological.
“If this were easy, what would it look like? Well, I would just press record and talk about something that I have interest in talking about,” Bosstick says.
The great equipment? It can come later, once you’ve done the critical work of connecting with an audience. The key is distinguishing between what you need now versus what you think you might need eventually.
Your Action Step: Write down everything you think you need to launch or improve your creator business. Now circle only the things you need for your very next step. Ignore everything else until you’ve completed that step.
5. The Long-Game Mindset
Are you eager to succeed? Good — but have some patience. You need to think in years, not months.
When Dear Media is working with a creator, for example, they don’t obsess over today’s results. “We’re interested in what does the brand look like in 4, 5, 6, 7, 8, 9, 10 years down the road?” Bosstick says.
This long-term thinking changes everything. Instead of chasing quick monetization, you focus on building genuine relationships. Instead of trying to be everything to everyone, you start narrow and expand strategically.
The creators who win aren’t necessarily the most talented or the luckiest. They’re the ones who understand that content is just the beginning — and who have a plan for what comes next.
