Framework: Selling to Side Hustlers
10 min read

Framework: Selling to Side Hustlers

When I started writing this report I wanted to talk about the Gumroad marketplace and discuss some of the most successful products that are listed on it.

But roughly 1000 words in I noticed that all examples I had picked had something in common: they don't sell B2B (business-to-business) or B2C (business-to-customer) but instead B2Side-Hustle.

So I deleted the introduction and started writing what you're reading right now.

I'll definitely share more Gumroad marketplace insights soon since there are lots of surprising products making a killing on the platform. But for now, let's focus on B2Side-Hustle opportunities.


B2Side-Hustle is an awesome framework that I first learned about from Jordan O'Connor.

The two key questions are:

  • What platforms and systems are people using to generate some side income?
  • And how can you help them earn more or streamline their processes?

If you can help people increase their revenue by, say, $200 a month and your tool costs just $20/month, the buying decision becomes a no-brainer. And unlike with B2B you don't need a dedicated sales team. Side hustlers don't need to wait for any kind of approval and are happy to spend money on anything that helps them earn more.  

While there is a lot of money to be made serving side hustlers (as demonstrated by the following examples), they're usually overlooked as a customer group by big companies. That makes B2Side-Hustle opportunities ideal targets for solopreneurs.

Below I want to talk about some incredibly successful examples. But first a short comment on the numbers I'm about to share.

Many subscriber and revenue numbers I'm sharing below are not publicly available, and hence I can't guarantee that they're 100% correct. Nevertheless, I'm confident that they're in the right ballpark since I got them straight from the source (Gumroad). In addition, when I'm estimating number's I'm always trying to be reasonably conservative, so the real numbers are probably somewhat higher.

Also I've decided to focus on subscription products since these are far more interesting for solopreneurs looking to build a sustainable business.

With that out of the way, let's dive in.

PrettyMerch Pro - $30,000+/month

PrettyMerch founder Haris Petrasitis clearly understands the value of B2Side-Hustle opportunities. His main product is a Chrome extension that improves the Merch by Amazon seller dashboard.  

Merch by Amazon is an extremely popular side hustles. All you have to do is upload an artwork and within minutes your design will be available on T-shirts on Amazon. For each $19.99 T-shirt sold, you get $5.23. And there's effectively zero risk as T-Shirts are only printed when someone orders them.

Sounds easy but in reality it's of course a tough business. Successful sellers typically employ several freelancers that create designs for them and publish hundreds of new T-shirts each month.

It's exactly these powersellers that PrettyMerch targets. In addition to an improved dashboard, the extension pulls up better analytics and makes it easy to manage T-shirts at scale.

The top of the funnel is the free version of their Chrome extension with restricted features that's currently used by 30,000+ sellers. This is certainly a solid number but their free-to-paid user ratio is actually insane.

They have 4600+ users paying $7.99/month (or $79/year) to use advanced features like the product manager and a batch editor. Hence in total founder Haris Petrasitis is making north of $30k in revenue each month from his Chrome extension.

Der Heidorn-Report - $10,000+/month

A product that taps into the same niche as PrettyMerch is Der Heidorn-Report (German for The Heidorn report) by Christian Heidorn. Two to three times a month Christian sends a research and strategy guide for Merch by Amazon sellers to his subscribers (~$18/mo).

In each report he analyses different niches and ranks them according to quantitative metrics like search volume and the number of related listings on Amazon. In addition, he provides a list of relevant keywords, Instagram hashtags, plus visual hints and popular phrases that can help to come up with T-shirt designs. Another section in his reports is an "Event Radar" where he highlights important upcoming events like the 4th of July or the CrossFit Games, and provides lists of  related keywords and phrases.

His reports look extremely professional, almost like a real magazine, and I have no doubt that they're extremely useful for Amazon Merch sellers. Nevertheless, I was blown away when I saw his subscriber count for the first time. After all, he only targets Germans who sell T-Shirts using Merch by Amazon and focus on the US market. That doesn't seem like a huge market to me.

My naive guess would've been that he maybe has a few hundred subscribers. Well, it turns out that he currently has more than 2500 subscribers. So if we do the math and take into account that he launched with a lower monthly price (€10/month) and probably gave away quite a few subscriptions for free, we can conclude that he's nevertheless making at least $10,000 in revenue each month on Gumroad.

In addition to his reports he now also sells all kinds of other products that target the same market. Among them is a design element subscription and he's also started to publish translations of his reports (145 subscribers).

His main traffic sources are a Facebook Group (1k members), his personal email list (8k subscribers), and his blog that now gets around 8000 organic visitors each month.

West Cost Dealz - $150,000+/month

West Cost Dealz is a private community for Sneaker resellers (another popular type of side hustle). An essential part of the offer is that subscribers get exclusive tips on sneaker drops and coaching on how to resell them on StockX.

The community made big news recently since it turned out that the founder's mother was the head of Nike’s North America business. Leaving this questionable aspect of the business aside, I personally never would have thought that more than 1600 people are willing to pay $99.99/month for access to such a community.

That's a total revenue north of $150,000 per month.

Closet Tools - $41,000+/month

What PrettyMerch is doing for Merch by Amazon, Jordan O'Connor is doing with Closet Tools for Poshmark.

To be honest, when I first came across Jordan's tool I had to google what Poshmark is. They describe themselves as a "social marketplace for all things style". As far as I understand, this means that Poshmark lives somewhere between Instagram and eBay. You can sell used clothes on the platform and one key to doing so is getting followers who you can share images of your clothes to.

Like Pretty Merch, Closet Tools is a Chrome extension that streamlines and simplifies common processes for powersellers. Most importantly it automates the "share" process on the platform (repost it to your followers) so that your clothes are always top of mind for potential buyers.

Once again I never would've thought that we're dealing with such a huge market here. There must be thousands of Poshmark powersellers. And many of them are happy to spend $29.99/month for Closet Tools since its total revenue is currently around $41,000/month.

During my research I came across a Closet Tool competitor that's sold on Gumroad and doing similarly well (1000+ subscribers paying ~$32/month).

Card Hounds HQ - $10,000+/month

Buying and selling sports card is a very traditional side hustle that's booming right now. But it's also one of the most complex hobbies you can get into. There are thousands of different cards, and it takes years to fully understand the economics behind them.

Card Hounds HQ is offering a helping hand by sharing the deals they're making and hosting a private community for traders. So it's similar to West Coast Dealz but with a focus on sports cards instead of sneakers.

They're currently much smaller than West Coast Dealz with just 178 paying subscribers. But if we take into account that they're charging $75/month, their revenue is still solid and most likely north of $10k/month.

Now sports card trading is of course a side hustle everyone knows about and there are already plenty of dedicated groups and products. Similarly, I could list dozens of groups dedicated to some form of stock trading. But let's skip that and talk about a more surprising type of side hustle.

All Things LEGO - $8,000+

The description in the image above says it all. Apparently, buying and selling LEGO is a kind of side hustle.

What All Things Lego offers alongside a handbook, is advice on what toys to "buy and hold for Q4 (this is peak toy/Lego season)", "live access" to the founder's trades and a private community.

There seems to be plenty of interest in this offer. Currently more than 200 people are willing to pay ~$40/month for access to the group.

I wasn't really able to find much information on who's behind All Things Lego and how they operate. Apparently, it was started by a guy called Charlie Swatkins who now calls himself The Lego Man on Twitter. Also the main acquisition channel seems to be affiliate marketing on Twitter.

Seems a bit shady if you ask me but nevertheless an interesting example for a less obvious kind of side hustle.


Now that we've walked into the more shady corners of the internet there are of course lots of additional examples we can talk about.

I now feel like I need a shower after looking at all these sleazy sales pages. So let's wrap up.

The Pattern

There's obviously a fine line between offering a genuinely useful service to side hustlers and selling a scammy "get rich quick" product.

Each opportunity is what you make of it and everyone has to decide for themselves what kind of game they want to play. But I'm convinced that for every side hustle there are plenty of opportunities for non-shady offerings, yes even stock trading.

The pattern that emerges from the examples we discussed above is that there are three types of B2Side-Hustle subscription products:

  • Research-as-a-service - sell monthly reports, leads, or data. This is for example, what Christian Heidorn is doing with The Heidorn Report.
  • Community and coaching - sell access to a private community and regular coaching sessions. This is what Card Hounds HQ and West Coast Dealz are doing.
  • Tools - automate common powerseller processes. This is what Pretty Merch and Closet Tools are focusing on.

When it comes to picking a type of side hustle to focus on, it, of course, helps if you have some first-hand experience. For example, Christian Heidorn was a Merch by Amazon seller for many years before he started selling his reports.

But this is certainly not mandatory. Jordan O'Connor wasn't a Poshmark powerseller when he launched Closet Tools.

And while it's of course possible to sell products in an established niche like sports card trading, it's probably smart to focus on new types of side hustles.

So let's ask ourselves: what new kinds of side hustles are booming right now?

Two that immediately come to mind are:

  • Anything related to NFTs. What tool could you create to help to streamline the process for NFT creators? Lots of regular people are suddenly interested in 3D animations and simpler ways to create them. Also listing them across different marketplaces is still a lot of work. And of course, a large majority of people is interested in flipping NFTs to make a profit. Hence any service that currently exists for, say, sports card trading (e.g. Card Hounds HQ, Market Movers etc.) will eventually exist for NFTs as well.
  • Flipping online businesses. I know quite a few regular (as in not rich) people who have started to buy online businesses ranging from simple affiliate sites to complex SaaS businesses, held them for a few months and then sold them at a profit.

    Marketplaces like Micro Acquire and Side Projectors are popping up everywhere and there is a lot of demand for high-quality information and tools.

    (Disclaimer: I'm personally involved in a project called Alternative Assets that offers, among other things, research-as-a-service for people interested in the space. Also I sold a previous project of mine that targeted this kind of side hustlers to Micro Acquire.)

I've prepared this spreadsheet with information on all kinds of side hustles that you can use if you want to dig in a bit deeper.

Let me know if you enjoyed this report or if you have any kind feedback since I still need to decide whether to make Framework Friday a regular thing!

Best,

Jakob

PS: Due to a configuration error, replies to previous emails didn't end properly in my inbox. So if you reached out but didn't get a reply yet just ping me again by replying to this email.

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