Aaron’s path to a lucrative side hustle didn’t begin with a business plan or a marketing budget. It started with Pokémon cards. Years before he would photograph vintage watches under diffused light and sell them for up to $15,000 a month, he was spotting edge wear and print variations on collectible cards. Those skills for noticing small, overlooked details transferred seamlessly into the world of vintage horology.
Scrolling through his Instagram feed, you see row after row of vintage timepieces. Each one is photographed cleanly, captioned concisely, and usually claimed by a collector within days. Arrows Vintage Watches now looks polished and professional. But it didn’t start with a website, a brand identity, or even the intention of becoming a real business. It began as a simple hobby fueled by personal curiosity.
Discovering the Art of the Side Hustle
Aaron grew up in Miami but now lives in Brooklyn. Before watches, his world was filled with politics and policy communication. Nothing in that background pointed toward a career in vintage timepieces. However, his father collected watches, which planted an early seed of interest. The real foundation, though, was built on his childhood experience buying and selling Pokémon cards and sports memorabilia.
“I didn’t plan to start a business,” Aaron says in a recent interview. “I just kept learning which watches people actually wanted to buy.” That learning process happened passively at first. He became active on watch forums, spending hours comparing auction listings and tracking sales results. He helped other collectors verify the originality of their pieces. Somewhere in that routine, he realized he was already performing the work that professional dealers rely on. The hobby began to feel like something more substantial. It was the early, unrecognized shape of a future business.
Launching Without a Big Vision
Aaron didn’t set out to build an e-commerce empire. In the beginning, he simply sold pieces from his own personal collection to fund new purchases. “I would sell items in my personal collection to finance other watches,” he recalls. This was a low risk method to test market demand. He learned which specific watches actually moved when real money was on the line.
The first watches he bought specifically to resell were Seiko Dolces. These were inexpensive to buy in bulk, reliable, and easy to service because of their quartz movements. They gave him early practice in pricing, photography, and resale strategy without the downside of costly mechanical repairs. His first listings went up on Reddit and eBay. He used whatever lighting he had, wrote straightforward descriptions, and priced items to sell quickly. There was no brand name, no website, and no long term plan beyond understanding how buyers reacted.
Building a Visual Brand on Instagram
For a while, Aaron focused on wholesaling watches to other dealers. This kept inventory moving, but it prevented him from building a recognizable identity. “I was doing a lot of wholesaling and figured I didn’t really need an Instagram,” he admits. Looking back, he sees that as a fundamental mistake. Watches are visual products. Buyers expect clean, consistent photography from someone they trust.
He didn’t even build a website until relatively recently. That shift changed everything. Instagram became the first place where new pieces appeared. The website provided longer descriptions, additional photos, and payment plan options. Reddit, eBay, and auction sites still play a role, but they now function more as sourcing and research tools than primary sales channels. This evolution represents a classic lesson in omnichannel marketing for anyone looking to make money online.
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How He Sources Inventory and Avoids Costly Mistakes
Aaron sources most of his inventory from online marketplaces and auctions. “I would say 70 percent of my watches come from online marketplaces and auctions,” he states. The rest comes from personal networks. “People who know the sort of watches I buy are my greatest asset,” he adds. When evaluating a potential purchase, he starts with the traits that determine long term value. He looks at dial condition, originality of hands and crowns, correct printing, lume consistency, and case shape accuracy.
Only after verifying those details does he consider liquidity. He asks himself how quickly similar watches tend to sell and whether replacement parts are easy to source. The biggest mistake he sees from new sellers is buying watches they personally like rather than watches the market actually wants. “My biggest red flag is buying watches I love thinking that they’ll sell well,” he warns. Understanding which watches have active buyers takes time and research. Skipping that step leads to expensive lessons.
Aaron typically resists the term “flipping.” He prefers to think of himself as a curator. “I buy items I’m personally interested in and rarely sell something I wouldn’t wear myself,” he explains. To him, flipping is transactional. Curation is about reputation and trust.
The Power of Transparency and Authenticity
Aaron does not restore watches before selling them. Instead, he focuses on pieces that already display the kind of honest wear collectors actively search for. “Part of what I sell is watches with vintage charm that are in honest condition,” he says. He draws a clear line between being a dealer and being a watchmaker. He handles all authentication work himself but does not perform mechanical repairs. “I value honesty above all else,” he says plainly.
Instagram is where most of his sales happen now. He posts new watches to his stories first, often before they ever reach his website. This allows him to show how a watch actually looks in real lighting. “I sell a lot by posting to my story,” he notes. However, what makes Instagram work for him is not just visibility. It is access. His direct messages function as informal consulting. People ask about authenticity, servicing needs, or simply compare one watch to another. He answers every message, whether someone is ready to buy or just trying to learn.
Managing the Side Hustle and Planning for the Future
Aaron does not run Arrows Vintage Watches as a full time job, but it still occupies several hours of his day. He spends time sourcing pieces, answering messages, and updating listings. “A lot of this is passive work,” he explains. Once the website launched, the business evolved from a simple sourcing loop into something that required wearing every hat. He is the photographer, copywriter, marketer, customer support team, and operations manager. “If I don’t do it, it just doesn’t get done,” he laughs.
Looking forward, he wants Arrows to become more than an online shop. “When people ask what the end goal is, I like to say having a boutique,” he shares. He imagines a small, curated physical space where watches are displayed alongside antiques. He also wants to make the brand feel more accessible than the traditional dealer model. Many large dealers maintain closed door offices and use heavy markups. Aaron prefers a conversational approach, especially for younger collectors who are still learning the ropes. As the business expands, that is the group he wants to serve. He hopes to shape a more open, less elitist vintage watch culture for the next generation of enthusiasts.
