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How I turned nostalgia into 10K/month in side income

How I turned nostalgia into 10K/month in side income

In late 2020, I hit a career inflection point like a brick wall. I was firmly in my 30s, working in content marketing roles for the past two years after a long career in journalism, yet more restless than ever before. I knew I needed to change things up in my life, but wasn’t sure how. After some self-reflection, I knew a few things to be true:

  1. I had written for my entire career, and I wanted to try something different
  2. I wanted to lean further into building a life outside of work and parenting
  3. I wanted to further rekindle my love of music in any/all forms
  4. I wanted to move my life financially forward in some way, without burning myself out after a physically and emotionally taxing period

Over the course of the previous year, scouring the internet for vintage clothing had been my happy place, a place of calm amidst doomscrolling in 2020. The rush of adrenaline that came with finding an appropriately-priced gem before anyone else was my form of escapism. This got me thinking:

  • Could I lean into my music-related passions in a responsible financial way and without exposing myself to pandemic-related health risks?
  • Or was I just lost in a mix of boredom and nostalgia, as opposed to actually connecting a passion to side income?

I like to characterize the two questions above as the “is this a thing?” quandary. The answers would come soon enough: This is the true story of how I built a monthly five-figure vintage clothing empire.

The research

I started where any former journalist would – reading. Namely, I began to research everything about the vintage market. To start, I needed to know the landscape. What was the going rate of vintage nostalgia these days? The answer was, in fact, a lot. Based on my current collection of hundreds of vintage band shirts acquired from shows, friends, and scouring the internet, I estimated that I could already have thousands of dollars in screen-printed cotton on my hands. Well, I was wrong. It was actually tens of thousands. My Green Day t-shirt from the 90s? That’s $500 in the right condition. An original Black Flag logo tee? You have at least $1,000 on your hands. The deeper you get into punk eras, the more money you’ll likely have in your pocket.

Reenactment of Nick doing his research

If I was going to suddenly propel myself into the unknown (and competitive) world of vintage band shirt (re)sellers, I needed to do more research. Here’s a few notes I jotted down at the time:

  • Should I sell to stores directly?
  • Should I start an online store?
  • What is the difference in revenue between selling online or directly to stores?
  • Did I want to keep my business local, national, or global?
  • Did I want to acquire more shirts or just sell from my collection?
  • How much does shipping clothes even cost?
  • Could I use eco-friendly packaging without cutting too deeply into my bottom line?
  • What would my revenue be post-fees and taxes?
  • Did this side project have a beginning and end date?

Choosing a platform

Unbeknownst to me, online vintage retail has changed a lot in recent years. Entrepreneurs (and thus, venture capitalists) have seen the same opportunity to disrupt the vintage market, and it was no longer an eBay and Etsy free-for-all. Depop, Grailed, Poshmark, and Mercari are among a growing number of e-commerce companies specializing in vintage resell, banking on the laziness of users like me and digital reach that comes with an all-inclusive platform to sell your stuff. So, I dug in, focusing on what was most important for me to keep this business going. In no particular order, this included:

  • Platform UI aka the “is it cool to the end user?” eye test
  • Revenue sharing with the platform (along with any other fees)
  • USPS/postage integrations
  • Ancillary bells and whistles (video, paid search, strong SEO)
  • Brand affinity (do people actually like buying listings from these companies?)
  • User vetting/fraud protection

I also wanted to meet buyers where they were. I for one had spent countless hours on Etsy seeking vintage wares from around the world, and knew that there were legitimate sellers (and buyers who beat me to some listings) on the platform, which gave me some peace of mind.

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After spending more hours than I care to admit running through these platforms, seeing who acquired whom in recent years (e.g., Etsy x Depop), and understanding all of my paths to least passive income resistance, I settled on Etsy with the idea that I would move or experiment with other platforms if my shiny new business wasn’t getting any traction. They offered the best UI for me, competitive fees per listing, decent SEO, and paid tools if I wanted to opt in. Plus, they’d been around the block for a while, so I felt more confident about the buyers (and fraud prevention/protection) on the platform.

The “business plan”

Believe it or not, I made a business plan that no one else will ever see. Why? Because if this venture was going to be real, it needed to feel like a real business. It also included a few rules of engagement. For instance, I promised myself I would spend no more than 3-5 precious weekend hours thrifting, writing and optimizing listings, taking photos, and posting my products on the site. Any more than that during a still-raging pandemic and I would burn out.

I would then set revenue targets, that, if not achieved over 3-6-9 months, I would reassess whether this was really worth it. If things were going well, I would start using my marketing skills — social media, email, etc.— for my own benefit.

On that last note, I repeatedly asked myself whether I had the time or energy for branding my new endeavor, outside of necessities such as naming the darn thing. This included:

  • Laying claim to a personalized URL now vs later
  • Going out to small/independent businesses in the neighborhood for collaborations

Perhaps the greatest barrier to launch was letting go of parts of my collection, which had been carefully built and curated over time. I wasn’t just giving away clothes, but memories. On top of that, I was suddenly in charge of quality control. While I (mostly) do not care if I buy vintage bootlegs from bands (I can appreciate the hustle!), the vintage community sure does. And they’ll make you pay dearly for it. If you’re lucky, this might only be in negative reviews and refunds.

Now, I had to start another layer of research, understanding the difference between vintage and non-vintage tags, the best way to understand whether or not you have a legitimate old piece of clothing. For example, do any of these tags mean anything to you:

Source: Instagram (@vintageminer)

Now, I was ready to get the store off the ground and rolling. East 7th Vintage —named for my former street in Brooklyn — was born.

The execution

Step one: actually listing my items (no need to get into how I chose the shirts, although I will say there were more than a few emotional, Marie Kondo-esque goodbyes).

I decided to create templates for my listing write-ups and picked a place in my apartment that received good natural light for the images of each item. And, because tag sizes in the days of yore do not reflect current ones, I pulled out my tape measure to give accurate sizing for potential buyers . It would end up looking something like this:

Source: Etsy 

It was time to hit publish. And then, I waited. And waited. And waited some more.

After 1-2 months without traction, I got my first sale! Then another. And as I got better reviews (fast shipping, quality of the items), Etsy’s search algorithm rewarded me as well. More sales kept coming in. I began to add more listings to keep up, and the purchases kept coming. Before I knew it, I was bringing in $1,000 in the first month, then $3,000, and then had my three best months at more than $10,000.

The good news is that with all of the investments I made into my business plan, templates, and an ample inventory, my overhead costs were low and this became a new passive income stream. Now, whenever I have time or sales appear to be dropping off, I can add more listings from my collection or use revenue to acquire cheap finds around New York or online. The store will always be there, it’s just a matter of allocating time to it. There are also so many other areas of improvement, including:

  • Giving more time to thrifting new items
  • Taking better images for the site, including tapping friends on the shoulder to serve as models (if not myself)
  • Spending more time on pricing research for consistency

Talking about my 10K side hustle today

First off, there’s a massive asterisk or disclaimer here that is worth adding: I am in a position of privilege in that I got to pursue this side hustle at all. Admittedly, this began to catch up with me: my two full-time jobs, now at Polywork and for the past five years at “Parenting, LLC”, did not leave me with a great deal of extra time to dedicate to the business. The store is currently bare bones and needs new inventory. The good news is that the foundation of a five-figures business has been established already, and requires a weekend or two of reinvestment to start back up again.

My advice to anyone looking to start a side hustle — whether it is a similar venture to mine or otherwise — would be the following:

1. Have a plan and a goal

I am motivated by deadlines and results. In this case, the joy has always come from finding the things, selling the things for money, and bringing even a small amount of joy to the buyers. Receiving comments from people like this one below doesn’t hurt either:

2. Don’t be hard on yourself when you can’t invest time

This is a big one for me. I will often ask myself why I’m not dedicating more time to what was once a thriving five-figure side business.

The answer is more satisfying when it’s because I’m being a better parent, colleague, and friend, or seeing more music on the weekends, which allowed this side hustle to become a reality in the first place!

3. Don’t be afraid to pull the plug

I have the luxury of truly treating this side project as a passion with a passive income cherry on top, which makes it much easier to pull the plug. I am fortunate this is not a business of necessity, so if I’m not feeling excited or motivated to make it work, I see no reason to keep doing it.

That said, there are always external factors. When I spent a (thankfully) short period unemployed, lo and behold the passion increased. Either way, it cannot be emphasized enough: there really is an art to sunsetting side projects.

Now that the store has been around for a bit, it was worth revisiting my “is this a thing?” questions I posed at the start of this article:

1. Could I lean into my music-related passions in a responsible financial way? Yes, at its peak, I was making more money than I ever could have imagined from my side hustle. That said, sustaining it would require more time and effort than I’m currently willing to invest without removing the enjoyment from it.

2. Was I actually connecting a passion to some side income? I believe so! Despite the amazing financial benefits, I was connecting with a new community of collectors, learning something new (see: deciphering tags), and bringing some joy to others along the way.