Last year, I launched my very first podcast. Now I have three.

But before we ever published episode 1 of podcast 1, I successfully booked over $4,000 in corporate sponsorships which covered our entire first season.

Landing such a great sponsorship deal on a podcast we hadn’t even aired yet was a major rush.

The truth of the matter is, booking sponsorships isn’t as hard or scary as some people imagine.

I’ve been doing it for years, making 95% of my revenue through sponsorships. Revenue that has allowed me to take my side-hustle full-time and continue to grow my business on my terms.

Today, I’d like to share with you how I was able to secure a solid sponsor for my first ever podcast and a few lessons you can apply when booking your own sponsors.

Let’s dive in.

First of all, the podcast is called Freelance to Founder. It’s a narrative podcast that tells the stories of freelancers and solopreneurs who, you guessed it, scaled their businesses to be bigger than themselves.

(Before I forget, Indie Hackers' very own Courtland Allen was featured in Season 3. You can listen to that episode here.)

Click here to listen to Indie Hacker founder Courtland Allen on Freelance to Founder.

Here's how it went down: I partnered with a very talented friend of mine who basically co-produced, recorded, edited, and made the podcast awesome.

His job was to make an amazing show.

My job was to sell sponsorship and promote/distribute the show.

We agreed we’d make an 8-episode Season 1 and pitch it to companies who are trying to reach freelancers and small business owners.

After we had a rough pilot episode, I got to work.

I’d like to tell you that I reached out to dozens—even hundreds—of potential sponsors before I got a serious bite, but I didn’t. I reached out to a very small group of people I knew would be highly interested.

Which brings me to my first two lessons:

Lesson #1: The work starts long before the podcast airs

Sure, you can use the shotgun approach and spam hundreds people with an email pitch about sponsoring your show.

In fact, I've used cold emailing methods to grow my business for a long time. I'm not opposed to it.

Or you can send a few, highly tailored emails to people you’ve built a relationship with.

As the cliché saying goes: the best time to start something is a year ago. But the second best time to start is today.

Whether you have a podcast in the works or you’re just toying around with the idea, start building relationships with people who might like to sponsor your content in the future.

Add value to their lives and their businesses. Build genuine friendships and trust. Find out what problems they need solved and how you can best serve them. 

Its these kinds of relationships that can potentially turn into profitable and enjoyable business partnerships down the road.

Lesson #2: First, get their permission to pitch them

This might sound a bit silly, but before you come in hard with a pitch and an offer to anyone—friend or not—you need to get their permission.

If you’ve known them for a long time, or you have a pre-existing relationship (which I highly recommend), then try something like:

“Hey, I’m working on a cool new project that I thought you might be interested in partnering on somehow. Would you be up for chatting more about it?”

Very casual. Looking for an affirmative response. Once you have it, you can go a level deeper.

If you don’t know them very well, try something like:

It looks like you and I are serving the same audience. I wondered if you’d be open to chatting about an idea I had on how we could partner on an upcoming project. I think it’ll be mutually beneficial for both of us. Would you be willing to discuss it? If so, I can send more details.

Waiting an extra email to pitch them is well worth the wait if it means you have their permission to come in strong with a sponsorship pitch.

Once you have permission, it’s time to go for it. Not in some slimey, sleazy way. Just keep going with the flow of the conversation. Explain to them the value your sponsorship will add and really sell it. 

And don’t turn into a robot—spitting out a canned pitch. Best honest, open, human. That brings me to lesson 3.

Lesson #3: Customize your pitch for each recipient

Nothing is worse than getting a canned, mass email from someone you don’t know.

If that’s the best you can do, all your emails are going to be deleted—or worse, you’ll land yourself in some potential sponsors’ blacklists or junk folders.

Best case scenario? You'll have to make thousands of cold pitches before you get a bite.

Yes, customizing your pitch improves your chances on all fronts: it shows you care more, it adds trust to the conversation, and it makes you much more human to your potential sponsor.

Here are just a couple ways you can customize your pitch for each recipient:

  • Include their name in the subject line. Honestly, I go extremely simple on this. Like: “Hey, James.” Not kidding. :) If you’ve already received their permission (see step 2), just hit reply and continue on the thread you’ve got going. Don’t make it weird.
  • Offer custom sponsorships based on the company needs. Do your homework and figure out who the company is trying to reach and what they need most (traffic, conversions, etc.). Then tailor your offer to match their needs.
  • Look into what they may have done in the past. If they've sponsored other podcasts you listen to, use that as common ground to start a dialogue.

Taking time to get to know the company your pitching will make a world of difference. If they feel like you’re interested in helping them succeed (not just begging for a check), you’re more likely to build a lasting relationship.

Lesson #4: Know what a sponsor wants

Before you can completely tailor your offer, you have to know what your potential sponsors want out of a podcast sponsorship deal.

Some of them are in it specifically for conversions—they have to make their money back in spades.

Other are in it for exposure—they care less about conversions and more about downloads.

Others are in it for the experimentation—they’ve heard podcasting is the hot new medium and they want to get their bearings and see what podcasting can do for them.

Remember, your job is not to focus on what you want (money for your podcast), but on what they want.

When you focus too much on you, you risk losing the deal.

Tell them how you’re going to help them reach their goals. Tell them how your show will get them more traffic or sales or exposure. And mean it. If you’re not being honest about it, they’ll see right through you.

You have to care, in this moment, as much about your sponsor’s business goals as they do. And then you must carry that genuine concern throughout the whole process. 

Last, but not least, keep everything in perspective and don’t get greedy.

Lesson #5: Don’t be greedy

As any good negotiator can tell you, it’s almost always better to have the other party name a price first.

I typically follow this rule when booking sponsors as well.

If this is your first show, the following rule is particularly important: don’t...be...greedy.

There’s a lot more at stake here than just the sponsorship money for your show.

Having a sponsor on your first season adds some serious legitimacy to your show. It says to listeners: we’re serious about the work we’re doing. It says to other potential sponsors: we’re worth investing in. It says to yourself: I can do this.

Unless you simply can’t make your show happen for less than a certain amount (which is pretty unlikely or you're doing it wrong), I would advise you to take any amount they offer.

If they come back and offer $100 per episode, thank them. Shake their hand. Maybe even hug them. They just told you they believe in you and the work you’re doing.

They believe in your enough to give you $800-$1,200 for something you haven't even made yet.

If that’s lower than you wanted, don’t stick your nose up at it, take the offer and set a time in which you’ll renegotiate terms. Let them know how happy you are and that it’s a bit lower than you expected, but you’re willing to give them a deal because their putting faith in you.

I planned my show, Freelance to Founder, by seasons specifically for this reason.

After season 1 aired, we took a look at the results (downloads, listens, conversions for my sponsor) and adjusted.

In Season 2, we booked over $12,000 in sponsorships and we've continued with steady growth and revenue ever since.

The key takeaway is this: if this is your first show, don’t get greedy with the per-episode amount you bring in. Take what you can get, take it as a compliment, and use it to leverage further shows, future sponsors, and more opportunity.

This is a marathon...not a sprint.

One resource I can’t stop sharing

The last thing I’ll share with you is this (and no, this isn’t a sales pitch...but it starts to sound like one...sorry):

A couple years ago, I first discovered Jason Zook.

Jason has built his entire collection of businesses on the foundation of selling sponsorships. He founded IWearYourShirt.com where he got paid to wear a company’s t-shirt for a day—every day of the year.

He's released tons of content on the subject of selling sponsorships.

In the year I discovered the power of sponsorships and some of Jason's work, I went from $3,000/year in sponsorships to $78,000 which eventually allowed me to quit my day job and work on my business full-time.

Jason did an episode on Nick Loper’s side-hustle podcast that I couldn’t get enough of.

Here’s the episode

If you’re serious about booking sponsors (even for content you haven’t published yet), you should really take a listen.

That’s it.

We're 5 seasons and 3 shows into this podcasting thing and I still can't wait to see where the world of podcasting takes me and my company.

I’d love to hear from you in the comments. Are you starting a podcast? Already have one up and running? Diving into the world of sponsorships? Or are you a seasoned sponsorship booker? Tell me your story. 

Cheers.