How to Hold a Garage Sale (And Actually Make Money at It)

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Summer is the opportunity to haul all your unwanted stuff onto the front lawn for your neighbors to buy, and then you have room for new stuff. That was my motivation recently, when I was prepping for a massive garage sale—but how to hold a garage sale, efficiently and effectively? I hit up an expert—Gary Vaynerchuk aka Gary Vee, a multimillion-dollar entrepreneur and digital celebrity whose moneymaking hobby is spending his weekends trawling the tri-state area for garage sale treasures and collectibles that he flips on eBay. (He’s also the CEO of VaynerX, the parent company of PureWow, so I had an “in” in getting the in-demand motivational speaker for an interview.) Here are six suggestions you may not consider when garage sale-ing—and one thing to absolutely avoid.

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1. Promote Online

“Hardcore garage sale people are always looking to Google townwide garage sales,” Vaynerchuk says, so he recommends calling local papers to list your sale, since it will show up in Google searches. Additionally, Vaynerchuk recommends community Facebook groups and online community social network Next Door. “Sometimes the old school way is the best way,” Vee says. “No question, a very strategic play is hanging big, colored signs at major intersections.”

2. Price According to Time of Day

In the early hours, from 7 to 10 a.m., price higher than you think. Then gradually lower the prices. to maximize both your profit and your ability to, well, get rid of your stuff. And consider bundling like items in bins to move a larger quantity at once. “As far as bundling, it’s always in play,” Vaynerchuk says. “But the thing to ask yourself as a seller is, do you want to bring it back into your house? Because end of day, what you are going to do is leave it on the curb, take one of your old signs, and flip it over and write ‘FREE’ and let people drive by and grab it.”

3. Consider selling on eBay

For smaller items that are easy to ship, consider listing your items on eBay, where you will reach the widest possible sale audience. If an item isn’t small or durable enough to ship, list it on Craigslist (or try local pickup on Facebook Marketplace). Vaynerchuk recommends researching what is a valuable collectible: “I’ve missed a lot of things—the consumer has gotten educated—early on, I had no idea that t-shirts were worth so much money, you know band and sports t-shirts, ‘80s and ‘90s t-shirts and hats.”

4. Social Media

“People always underestimate social media—Instagram stories, now TikTok for sure—they are a great place to get serious about it all,” Vaynerchuk says. True story: Reader, I sold half my garage sale items to friends who reached out to me after I posted, just for fun, a tracking shot of my yard and snaps of favorite little tableaux I set up around my front lawn.

5. Set Your Intention for the Sale (Really)

One of Vaynerchuk’s top money-making experiences visiting garage sales occurred when he purchased a bundle of Playbills. “I bought a bunch of 1940s to 1980s playbills, like 3,000 of them, for $40, then I went on eBay and listed them individually. It was a time-suck, but it was a $40-to-thousands-of-dollars arbitrage,” he says. Vaynerchuk allows that he made the flip since he had a younger brother who was willing to put in the hours listing each Playbill. Garage sale-ing is “a time allocation game almost always. If you have patience, eBay is great, but most people have no time, which is why they are doing garage sales in the first place,” he days. “So are you trying to maximize dollars, or are you trying to maximize the speed at which you get the junk out? And it ebbs and flows. Some years you have more time and you use eBay, other years you want to travel a lot and you have one big garage sale and get rid of it all.”

6. Prepare to negotiate

“You should always be open to negotiate. The quickest way for someone to not buy something from you is to not leave any room for negotiation,” Vaynerchuk says. “The buyer always wants to negotiate a little bit.”

7. Don’t Get Too Fancy

“Don’t think that you are a premium thrift store on the Upper East Side,” Vaynerchuk says. “So yes, I want you to price more aggressively in the early hours, but some people think they have an antiques store, and write $30, $40, $50 individually, versus other places where you can get it for a dollar.” For more garage sale-ing tips, check out Vaynerchuk’s YouTube channel.

dana dickey

Senior Editor

Dana Dickey is a PureWow Senior Editor, and during more than a decade in digital media, she has scoped out and tested top products and services across the lifestyle space...