My First Year on Substack & Launching Paid 💸
My First Year on Substack & Launching Paid 💸
Plus, your 2023 podcast resolutions
Happy New Year, Besties!
I love reading year-in-review posts, so I’m taking you inside my Substack factory to show you how the sausage is made. I’m sharing the lessons from my first year with you—a motley crew of indie podcasters, audio freelancers, and podcast industry folks—because growing and monetizing a newsletter is very similar to growing and monetizing a podcast.
In fact, I think newsletters and podcasts go together like peanut butter and jelly. I launched a new podcast this year—The Bleeders, about book writing and publishing—and used a lot of my learnings from putting out this very newsletter to build a more successful podcast ecosystem from the start.
Key dates:
Podcast Bestie went live on Substack on September 11, 2021.
I published the first issue on November 11, 2021.
Podcast Bestie was biweekly until December 23, 2021, when I announced it was going weekly, effective immediately.
Podcast Bestie celebrated its first anniversary AND launched paid on November 11, 2022.
Find the most advantageous, sustainable cadence for you (adjust if necessary)
I was in it for the long game from the beginning, but I was getting some immediate traction that assured me if I kept investing in the content, my audience would grow, so I doubled down just a couple of months in—going from every other week to weekly. On the flip side, late this summer, I realized I was spending too much time on production for my podcasts and not enough on promo, and I also needed more time for writing, so I took both of my podcasts biweekly. I’m so glad I made those cadence adjustments this year—it’s way more sustainable and fosters a sense of joy instead of obligation. If you ever feel stuck in an unworkable release schedule, remember: it’s not set in stone.
Allow yourself to find your voice & offering without external pressures
I knew from the start that I wanted to do a full year before launching paid, which freed me up to keep it light and experimental without feeling like I owed anyone set content. That has allowed me to find my voice, service, and offering as I grow. I’ve been delighted with that strategy. Even as things become slightly more structured with advertising and subscription obligations, I’m committed to keeping it flexible and playful on the content side and streamlined and minimalistic on the business side.
Note to Substack: I would have loved a tip jar feature for my first year because I did have expenses from the beginning. 🙂
Your paid launch might not go as planned (but keep going!)
I was on track to hit my goal of 2K free subscribers on Podcast Bestie’s first anniversary, so I went ahead with my plans to launch paid in early November.
Today, at the end of December, there are 2,341 free subscribers (and growing quickly), but not even two percent have converted to paid.
It’s slower than expected on this front, but I’ve got a big goal for the new year: 10K free and 1000 paid subscribers. What’s encouraging is that 32 people is enough for a constructive community. And the number of paid subscribers grows every week. I’m also learning some tactics to expedite that growth. Sending small previews of our most enticing paid content to free subscribers and running holiday sales seem to help.
Speaking of which… now is the perfect time to grab a discounted Podcast Bestie subscription!
Perhaps my biggest tip for anyone launching a paid subscription or membership program is to make sure you have a post-launch plan to grow your membership beyond that initial push. Even if you have a great launch, your promotional efforts will need to be ongoing.
Consider bringing on collaborators
Alongside the first anniversary, Michael Castañeda came on board as the resident Engineering Bestie, and we launched his column as premium content. I had wanted to involve Mike from the beginning. I was especially excited to include him because he has a separate yet complementary skillset that I thought would bring a lot of value to newsletter subscribers.
However, Mike took a leap of faith in producing extra content for not a lot of money, at least in the short term. The newsletter isn’t profitable *yet*, but we felt encouraged enough by the first year’s free subscriber growth to have confidence that we could continue to grow the brand, hopefully exponentially, and eventually, the numbers will make more sense for both of us.
Adding him to the workflow has been super easy: Mike and I have been working on projects together since 2016, so we already have an efficient process, an understanding of the other’s strengths, and a level of trust built up as collaborators.
Have a plan for growing organically on social media
If you’re struggling to get started on social media, it’s always a good idea to focus on one platform—ideally, one you actually enjoy using.
For Podcast Bestie, I occasionally promote on IG Stories, but my social media emphasis is primarily on Twitter because:
I don’t hate it.
It’s easy to schedule posts in advance.
There’s a thriving podcast community on that platform.
Posts are easily shareable.
From the beginning, my goal has been to promote every issue on Twitter at least twice, ideally more like four times, promoting different segments and the main content twice—the second one as #ICYMI a few days later.
Substack also has the option to auto-promote each newsletter on Twitter, so I always do that when I publish. I have a (very part-time) designer/social media manager who usually tackles scheduling the promotion, which is a huge help. But she’s created some Canva templates, so I can manage by myself if necessary.
Elon hasn’t totally ruined Twitter yet (and I’m optimistic there will be a new CEO soon), so I’ll continue with this strategy for 2023.
In 2022/2023, you need a video-first social media strategy
One huge area of neglect is that I’ve barely done any Instagram Reels or TikTok promotion for Podcast Bestie. I definitely need to remedy that in 2023. I want to incorporate more video promotion for Podcast Bestie AND my podcasts. No joke, it’s one of my New Year’s resolutions!
Send James Cridland at Podnews your podcast-related press releases
If you’re not sending your podcast-related press releases to James Cridland, you’re making a big mistake. Huge! To me, Podnews is the podcast paper of record, and James is incredibly welcoming of press releases. Make sure you update him if you’re launching a new show, a new season, or have a newsworthy milestone with your podcast or podcasting-related business.
Here are two of my press releases James published in 2022:
Shout out your newsletter every chance you get
It's totally free to be persistent in getting the word out about your newsletter (or podcast). I moderated a panel at Podcast Movement, and as we made introductions, I made sure to mention Podcast Bestie to the packed room of podcasters. I have a link in my email signature. I told the cashier at my grocery store. Talking about your newsletter or podcast costs nothing, and it's actually quite effective.
Pursue cross-promotions and collaborations
I love a good win-win. One of my favorite aspects of my newsletter crusade over the past year and change has been making and deepening relationships with other podcast-newsletters purveyors.
It’s been so refreshing for me personally and beneficial for Podcast Bestie professionally. Honestly, I’ve been undervaluing cross-promos and collaborations with my podcasts over the years, and this newsletter has shown me how essential they are. I want 2023 to be my “Year of the Collab.” If you have an idea for mutually advantageous cross-promotion, hit me up!
My favorite Podcast Bestie collab of the year was this takeover I did of Lauren Passell’s Podcasting Marketing Magic:
Substack has a cool and effective recommendation feature, which has garnered Podcast Bestie 887 of its subscribers! The following sweetheart newsletters recommend me (and I love them for it). Check them out:
If you’re bootstrapping, keep your expenses low
At this point, I operate without a budget, but as I mentioned, I have expenses. There’s the aforementioned designer/social media manager. And the money I’ve invested in paid promotions to date, including some that are upcoming. Plus, Mike does a column, so I’m giving him a minimum and will give him a share of the revenue as it grows. So while I’ve grossed $621 from paid subscriptions, my overall net revenue is still negative. My goal for 2023 is to have a net positive… like, very positive. 😉
Events can help grow your community (& are a potential source of funding)
I hadn’t even considered events as a source of funding until I unexpectedly got sponsorship for the LA podcast meetup earlier this month, with Libsyn stepping in as the presenting sponsor. I also got some donations for the party. And best of all, I added 55 new subscribers to the list, met a bunch of local podcasters, and loved throwing it. So I plan to do more events in 2023.
Even if you’re not making money, there are ancillary benefits
I recently got asked to write an article for a podcasting brand because of my work on Podcast Bestie (keep your eye out for more on that soon!). I also got asked to moderate a panel for Podcast Movement in August, so there have been definite upsides for overall career visibility, even though that’s not translating specifically to newsletter revenue at the moment.
Consider buying ads to promote your newsletter (or podcast)
For paid subscribers, I’m going to do a full rundown of the paid promotions I’ve done for Podcast Bestie: where I bought ads, how much I spent, and whether or not it was worth it.
If you’re nosy like me and want the complete behind-the-scenes blueprint and NUMBERS from my first year of Podcast Bestie, subscribe. I’ll send that out to paid subscribers in January—along with my Castro and Overcast podcast advertising experiments—but I’m running a New Year’s special now!
Planning for 2023
I want to do a more dialed-in version of everything I did this year, plus get my Podcast Bestie podcast, video, and SEO game poppin’ and do some valuable tentpole content for both free and paid subscribers, but I’m limited by my own bandwidth and budget at the moment.
However, I’m determined to fix both of those issues in the new year by bringing in more revenue, which will pay for more of my time and help buy the necessary assistance and exposure to grow.
Selling ads in your newsletter
One completely untapped form of revenue is having advertisers in my newsletter. I technically already launched ads—though so far, it’s crickets. LOL. Admittedly, it was a soft, quiet launch, but I was still super surprised by the lack of response. I had people contacting me about advertising in the newsletter starting a few months in—waaaaay before I offered it—and then when I finally went live with it on the one-year anniversary… nothing. This is a major area I would like to improve in 2023.
It’s a little confusing because I’m a purchaser of paid ads, and I think what I’m offering to reach my super-engaged and quickly growing podcast-centric newsletter audience (plus social media promotion!) is a steal. It’s a very niche audience, and my open and click-through rates are excellent, so these ads have a lot of value. I recently reviewed the offers and made some slight alterations to make them a further steal. I mean, take it from me already!
For the next week, I’m running a sale for Besties who want to try out my advertising options. All available inventory is 25 percent off with the discount code BESTIE.
I look forward to serving you for another year. I'm more optimistic than ever about the indie podcasters' place in the industry. The medium is built for lean crews that give a f*ck about what they're making. I'm excited to grow together.
As we head into the new year, I want to feature your podcasting goals and planning tips:
What's your biggest podcasting-related goal for 2023? Do you want to hit a download or revenue goal? Do you want to book a dream guest?
How are you trying to improve your production and/or marketing processes in the new year? Are you trying to batch your workload more efficiently? Spend more time or money on promotion?
How are you trying to take your podcast or podcasting career to the next level?
So… ROLL CALL! 🗣
Share your podcast-centric intentions and resolutions in the comments below! I'll pick some to feature in an upcoming issue.
Follow me @courtneykocak on Twitter and Instagram. For more, check out my website courtneykocak.com.
What a great read packed full of info! You got me on board for a paid subscription this year!
"Year of the Collab", love it.
You linked to several podcast Substacks, how much does what they're writing about influence what you choose to cover?