First $1,000: “I succeeded by following contradictory advice…”

Jess Dollar started Pretty Old Books in 2018 in Nashville, Tennessee, with one product and one platform in mind: selling vintage book sets, bundled by color, as home decor on Etsy. She researched the category thoroughly, studied what other successful vintage Etsy shops were doing, and had her first sale within days of opening.

She didn't wait for everything to be perfect before starting — she opened with what she had and kept improving as she went. That approach paid off again when an unplanned opportunity showed up: she'd been posting Instagram videos of the vintage books she found while sourcing inventory, and a follower asked to buy one of the individual books shown in a video. Jess hadn't planned to sell single books, but she figured out how to invoice through PayPal and made the sale anyway. That one exception turned into regular Instagram story sales of individual books, which eventually grew to make up half her monthly revenue.

Her next pivot came when she opened a Shopify store, which she originally saw as a convenience for existing customers so she could avoid PayPal fees. Instead, Shopify's Facebook integration made it her top sales channel, mostly to strangers who had never heard of her through Instagram or her email list. She hadn't planned for Facebook shops or Facebook Marketplace to matter at all — it happened on its own.

Her most recent shift came from a move, from Nashville to a small town in Alabama, which changed what inventory she could source. She now sells far more individual books than bundled sets.

Jess's takeaway is that her first $1,000 came from doing two contradictory things at once: researching a plan and following through on it, while staying flexible enough to adjust when customers showed her what they wanted. As she puts it, "Your first $1,000 will come faster if you have a plan but aren't married to it." Check out her shop at PrettyOldBooks.com.

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