Behind the DMs: 5 Questions Podcasters Keep Asking Me

Some weeks, the questions come in quietly. Other weeks, they flood my DMs.

And lately? It’s been the latter.

Different podcasters. Same questions. And if you’re reading this, there’s a good chance you’ve asked one of them, too.

So instead of answering them one by one, I’m pulling back the curtain and sharing the exact 5 questions I’ve heard on repeat—and the real answers I give behind the scenes.

This isn’t a generic FAQ.

These are the gritty, honest, "what am I missing?" questions podcasters ask when they’re tired of guessing and ready to grow.

And better yet: I’m giving you a few actionable steps with each one so you can start moving forward today.

1. "Can I pitch a brand if I don’t have a huge audience?"

Short answer: Yes.

Longer answer: You’re not pitching your download numbers. You’re pitching your influence.

If your audience trusts you, brands care. If you know how to position what you do have, it becomes valuable.

We’ve helped podcasters land $5K, $10K—even $80K partnerships without six-figure downloads.

So yes. You can pitch. The right way.

What to do now:

• Write down your "Trust Points" — reviews, DMs, shoutouts, or engagement that show people listen to you.

• Map your platform ecosystem (email list, LinkedIn, Instagram, etc.)

• Choose 1 brand that already serves your audience and write a rough intro message. You’re not pitching yet—you’re observing your alignment.

2. "I think I’m ready for brand deals... but how can I be sure?"

If you’re asking this, you’re already ahead.

Here’s the quick gut check:

• Are you clear on who your show is really for?

• Can you speak to what your audience values?

• Are you publishing with consistency?

If yes, you don’t need to wait for permission. You need a plan.

What to do now:

• Write a 1-line description of your listener: Who are they, and what are they looking for?

• List 3 goals they have (e.g. less overwhelm, healthier lifestyle, confidence in parenting, etc.)

• Ask: Which brands are also trying to help with those goals?

3. "I don’t want to sound salesy. How do I reach out without it feeling gross?"

This one hits deep.

Nobody wants to feel like they’re begging. And that’s where most podcasters hesitate.

But when you approach a brand as a collaborator, not a cold caller, everything shifts.

The pitch isn’t: “Please sponsor me.”

It becomes: “Here’s who I reach. Here’s why they trust me. Let’s create something that actually helps them.”

See the difference?

What to do now:

• Shift your mindset from asking to offering: What experience can you give a brand?

• Create a "Win-Win-Win" Venn diagram: You, your audience, and a brand. Where do all three align?

• Write your outreach message like you’re recommending a collab to a peer—keep it human.

4. "How do I know what to charge?"

This one comes up every week. And every time, I say:

“If you don’t name a number, the brand will. And it’ll always be lower than you deserve.”

You’re not charging for airtime. You’re charging for access—to your trust, your influence, and your ecosystem (email list, socials, voice, all of it).

Stop guessing. Start owning your value.

What to do now:

• Work out your base production costs: hosting, editing, admin, etc.

• Add in your time value (hourly or monthly). Don’t ignore this.

• Use that number as your bare minimum to break even. From there, build package options.

5. "How do I even start the conversation?"

Spoiler: You don’t need a pitch deck to start.

Some of our clients have secured partnerships off one DM.

One brave email.

One "Hey, are you open to collaborating on this?"

Start messy. Start before you're ready. Just start.

What to do now:

• Make a list of 3 brands that align with your values and audience.

• Draft a simple message: "Hey [Name], I love what you’re doing with [X]. I host a podcast that speaks directly to [your audience]. Would you be open to chatting about a potential collaboration?"

• Hit send. You learn by doing.

Final truth:

Most podcasters are out here doing the most — creating, promoting, managing everything solo — and wondering why monetization feels just out of reach.

But you don’t need to do more.

You need to channel that energy into the right moves.

This is why we’re booked out until July. Because when podcasters get clear on their value and start positioning themselves with confidence—brands notice.

And deals start happening.

Want to know if your show is actually partner-ready?

Let’s take the guesswork out of it 👉 Book a free 15-minute fit call here