How does Cheek Media make money?

Financial transparency matters, here's some in$ight from me.

Over the next couple of months, this Substack will be changing. Part of the how and of this is referenced at the end of this article. You’ll be receiving a consistent mix of external contributor pieces, news breakdowns and personal pieces from me. I want to write more about the professional + business insights I have, so if this is of interest and you have particular curiosities or topics you’d like covered - please leave a comment. As you’ll read in this piece, Substack is actually my strongest and most consistent revenue stream.

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I left the comfort of my salaried legal role 2.5 years ago to make running Cheek Media my full-time job. What started as a hobby Instagram account became my career, leaving behind a legal industry I knew was not meant for me.

At the time, I was the highest earning 23-year-old I knew. That was less of a flex and more of a shock. In the space of one year I had moved from being a trainee Industrial Officer at the Electrical Trades Union (QLD & NT) on a lower apprentice-style rate, to working four days a week and hitting six figures (the superannuation on top of this salary was something absurd like 27% - I had planned to die at this workplace I loved it so much). The conditions at my union were amazing as you’d expect, my mind/body/spirit just hated the law.

When Cheek Media hit 50,000 Instagram followers in late 2022, I received three offers from publishers to write a book. I knew I wanted to leave Brisbane and move to Sydney to expand my opportunities and accelerate Cheek’s growth. This was my chance. After signing with a small progressive publisher I couldn’t wait to work with, I resigned. I cried in a really ugly, snotty way in the office of my big boss as I told him.

My book advance was $60,000, paid in multiple parts. Book contracts are interesting. For Bite Back I was paid half when I signed the contract, and the second half when the book was published a year later. 10% of the Recommended Retail Price (RRP) of every book sold goes to me (towards paying off the advance). This is industry standard. Given that was $3.49 a book, I need to sell more than 17,000 copies to make more than that initial outlay. I haven’t done this for either of my books yet. When people think of books, they often think of millionaire bestsellers. It just isn’t an accurate picture of what many writers experience. I work with one of the most amazing publishers in the industry, and got one of the most generous advances. This was life changing for me.

This advance was the only income I had for the first twelve months of running Cheek solo. I am so grateful to my publisher for this opportunity to take a financial risk on self-employment. It was my sink or swim moment. It was what I depended on, alongside my savings. Once I paid tax on that amount, I was not left in a healthy financial state. I was living in a studio apartment with a new laptop and a Facebook Marketplace’d everything else. I was cooking within two metres of where I slept. I loved every fucking second of it. I lived alone and worked alone in a new city. I got drunk on weekends and took long walks in the middle of a weekday. I didn’t date or have sex for the majority of 2023. I cooked my salmon and made my posts and started Big Small Talk after meeting my co-host Sarah by chance while doing another interview she was producing. I started doing speaking gigs here and there for free or around $250. My approach that first year was: say yes to every opportunity, free or paid. Meet as many people as you can. My second lesson was: don’t do big corporate gigs for cheap, they have money and should spend it (that money gives you more time and capacity to do free events and make free content).

I started paying myself in 2024. At first, it was a salary of $50,000 a year. Six months later I was able to increase that to $75,000. Every time I move this needle I feel invigorated. Slowly but surely, I get a little more comfortable investing in myself and not worrying the whole thing will topple a month later. Ironically, I find that I am conservative in the space of spending. I make sure I am safe and ready before taking the next step. My personal account still screams ‘stop buying oat cappucinos’. To that I say, ‘fuck no’.

Finances for me haven’t historically been a strong point. What I’m sure politics feels like for a lot of people is how financial information feels to me. Fear inducing. Purposefully confusing. A system made by men, for men. Important, but something I am incredibly avoidant of. I trace a lot of this back to growing up in a household where money was a source of shame, resentment and strain. It was not spoken about freely or with curiosity - it was a sore spot. I credit my own changing opinion of money not with my own personal finances, but with the need to get uncomfortable and serious with it rapidly when running a business. Cheek’s success has bred confidence in me around my commercial skills. Only in the last year have I gone from seeing myself as a content creator to actually what I am, an entrepreneur (LinkedIn has poisoned the word).

Getting to the point of making voluntary superannuation contributions and investing in four ethical ETF’s in my mid-twenties made me feel like the Barefoot Investor’s #1 student. But when it came to income, I just wanted to be able to buy a new top for a party and get brunch on a Saturday comfortably. Founding a media company in this era should be every indicator that I don’t have profit margins on my mind. However, you can’t grow a progressive platform like Cheek without conceding that you need to make money ethically and sustainably, and know where to re-invest it for maximum impact and benefit for your community. The last few years have demanded a level of financial literacy from me that I am so thankful to now have. I cannot scale and succeed in business if I don’t have a handle on my accounts and spending.

Earning money in progressive spaces is delicate, to put it lightly. While many male athletes and male presenters can do million dollar deals with a bank or an alcohol brand without batting an eye, I agonise over the areas I can advertise in and where my personal lines are. Being a young, loud woman with a hard-left lean also often means some will pigeonhole you into ads for tampons and face cream. I love these brands and products, but the exclusive categorisation feels unfair. The need to make a living without ‘selling out’ in the eyes of your audience can be a precarious balance. Not only does the choice of product rightfully matter, but the avenue through which it is done also has different value and impact. For example, an Instagram reel feels far more invasive than a podcast ad-read. I decline sponsors more than I accept them, and that is out of personal worry and high standards. Sometimes watching footy players happily take six figures from betting companies with zero backlash does feel like a punch in the stomach. But, I know where my line is. The people who follow me, I’m proud to say, also have clear lines. Still, there are inherent double standards worth pointing out.

As Cheek grows, so too should my financial transparency. As I begin to build the business far beyond myself, here’s what you should know:

What are Cheek’s five main revenue streams?

1. Substack

   Right here, baby. With less than 2000 paying subscribers, this is my biggest revenue stream. Consistent, engaged and attentive followers supporting me to continue doing the work I currently do (and clearly with minimal expectations for how often I post here - I’m working on it) words aren’t enough to express my gratitude. This is the safest and most dependable platform for earnings. This is the place I need to spend more time and grow, which is my top priority for the next 12 months.

2. Vibe partnership with Normal

   Instead of agreeing to ten small, in-feed ads over six months - I wanted to work longer term on single products in partnership with a women-founded small business. There is an inherent brand risk in selling sex toys, and I have received criticism for it. That critique only holds weight if I am able to be shamed. I’m not. Building strong relationships with two or three incredible founders is preferable to making a weekly reel with a discount code. I love projects and connection building. Normal re-invests much of their profit into making free, progressive resources on sex-education, body positivity, gender, sexuality and beyond. If selling an item designed to enhance pleasure makes you flinch, that says more about you than my revenue stream. Let people judge, but it is one continuous project that will allow me to expand the presence of independent media in Australia. The way this works: I receive a percentage of the profits from Cheek (our palm vibrator) and Plum (our new clitoral and g-spot vibrator) sales. The percentage decreases over time. I also receive an additional commission for products purchased in the same cart as mine AND for any Normal products bought using the code CHEEK (which also gets the buyer 20% off).

   Oh, and to be sneaky…You can pre-order Plum HERE (first batch sold out, second ships mid-August) or our first toy Cheek HERE.

3. Podcast sponsorship

   Each month we sell podcast sponsorship space to aligned businesses. This isn’t income that goes solely to Cheek. The podcast revenue is shared between the studio, my co-host, and myself. Studios, as a rule of thumb, take around 50% of the income from the ad space they sell. Some offer different splits, but this is the most common approach. Yes that, is a high percentage - but people who consume podcasts (and start them) deserve to know how the sausage is made. In addition to this, as Big Small Talk covers heavy news, it can be challenging to find businesses willing to sponsor content they cannot approve in advance and have no editorial say in. That’s also what makes it great though, because the companies that do work with us are significantly valued by our listeners for exactly that: backing opinionated progressive women. We have never had to change our coverage for a sponsor, I am immensely proud of that.

4. Live events

   Tours, key notes, panels. Exactly what you think. This can be at an awards night, a conference, a corporate gig for a launch, a presentation at a school, a writer’s festival. I do some for free and some for a higher price in order to be able to do more for free. How I charge is generally dependent on (1) the business, (2) the location + time commitment required, and (3) the brief. Not much further explanation needed.

5. Instagram sponsorship

   The scariest of all. Posting a sponsored reel makes me want to crawl into the earth and have it swallow me up. Reels feel invasive for viewers. Maybe that’s just my assumption, but an ad feels particularly jarring for someone who prides themselves on making authentic content. My general aim is to work with organisations who want to fund Cheek to publish educational material with a side of promotion. For example, I was able to work with Super Members Council before the election. They had funding to supply me with research and to collaborate on two reels. Being financially supported to talk about superannuation was the best paid partnership I’ve ever done. Every view, like and comment matters on these posts and increases the earnings and value you can provide to a brand. If you like a creator, make sure to engage with these posts because it helps immensely.

Next, what does growth look like for Cheek?

For a year of self-employment, I was attempting to manage these revenue streams alone. I took pride in taking on all of the work: administrative, operational, creative and commercial. Skills developed at the same rate as burnout. I quickly hit a ceiling of what I could execute and how much Cheek could grow.

As a solo operator, the hardest thing to do is decide who you bring on first to assist your small business. There was one thing I wanted to avoid: developing a startup culture where a basketball hoop, bean bag and Friday beer concealed excessive labour and burnout in early onboarded staff. I wanted to create clear lines before I figured out longer term vision. I also never sought external investment. Grow slowly and continue to love what you do, don’t scale fast for the sake of success. This has always been my strongest policy with Cheek’s development. Money has been floated and I have said no, proudly.

In the last twelve months I have brought on two part-time weapons. Both are 22-year-old university students with other jobs and busy schedules. Each reached out to me with a clear pitch and skillset, their initial emails were so good that I took notes. One is in Canberra and remotely supports me with research one day each week, the other helps me with audience growth strategy 1.5 days a week. Having a touchpoint for social media ideation and feedback on what I’m creating is motivating. The support of clearly sourced and summarised news saves me so much time, and gets me up to speed at the start of each week.

But working with both Soph and Lara is ultimately benefitting my professional development. I learn from them, but I also learn what kind of manager and founder I want to be. Creating healthy and effective working environments with freedom, flexibility, consistency and clear communication are all an important learning. I underestimated how much I would love this part of the story.

The next step?

Building a more dependable and diverse media platform, with more separation from me. Creating a platform tied to my identity has created many blockers for growth and personal challenges, both public and private. While I am firmly staying with Cheek, my role should evolve in the coming year. In the next month, I’ll be bringing on a managing editor to run the day-to-day operations of Cheek. She will be responsible for corresponding with external contributors as that avenue is firmly established, developing this Substack platform, managing posts and helping to create a stronger baseline for the platform that isn’t dependent on my calendar that day.

Cheek will still be driven by progressive opinions on the news, but the breadth and depth of coverage will improve and the contributing voices will rapidly expand.

Exciting.

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If you have a particular business, founder, Cheek behind-the-scenes topic you want covered - please feel free to leave a comment!

H.

Photo by Joshua Hoehne on Unsplash