How I Finally Won My First Painting on DealDash!

Ok, bidders—after over two years, I finally won my first big-ticket painting on DealDash! I can tell you it was no easy task but one that I would love to share with you. If you feel you’re stuck in the rut of winning smaller items on DealDash, these tips might just make winning that next mid- to big-ticket item possible.


  1. Know the Competition

No, this doesn’t mean invite them over to grill them for all their bidding and winning secrets, though that would be fun, wouldn’t it? Simply put, there are experienced bidders who know the ins and outs of winning items.  Make sure you remember them.


  1. Utilize the Winners Tab

I bring up the Winners Tab before I even browse the auctions. It’s the first thing I do. Why? Because I want to know who has been winning the big-ticket items recently. A common thought would be that if you won a painting recently, you will try for another…and another. By having the Winners Tab up, you can also search your competitors’ names while you are in an auction with them to see if they have recent wins.


  1. Don’t Retreat

Just because someone recently won a big-ticket item and they are trying for another doesn’t necessarily mean they will win again. There are many reasons for a bidder to back out of an auction and most bidders don’t have an unlimited supply or aren’t willing to invest everything they have. Be willing to stay in an auction at least for a certain number of bids just in case.


  1. Be Patient

It’s easy to say to yourself, “Oh, I’ll just remove my bids and watch the auction and jump back in.” However, on more times than I can tell you, I have done just this and the bidders go from ten to one in a blink of an eye and you’ve lost your chance. Hang in there!


  1. Use BidBuddy and Walk Away

Watching my auctions is a habit of mine but during big-ticket auctions, I prefer to set my BidBuddy and walk away…at least for a little while. It’s too tempting to hold back on bidding and in auctions you just never know what the competition is going to do. I have seen many times where items have been won with just one or two bids because the other bidders (and many of them) placed just one bid to secure a spot in the auction with the hopes of saving bids and re-joining the auction later. This is not always the best strategy.


  1. Consider Your Exchange to Bid Options

I had always wanted to win a painting. They are expensive items and surely must generate a hefty “exchange to bids” benefit, right? Don’t be surprised if that’s not quite the case. With my own win, I won a painting worth over $2000 and when I won it (after spending about 200 bids), I quickly realized the exchange to bids offer was only 500 bids. Yes, of course I took the bids, but the lesson was not to count your bids before they are exchanged to bids!


  1. My Best Advice

When it comes to paintings and other big-ticket items, my best advice is to find an item you would really love to win and receive, do your homework and get bidding. You simply can’t win if you don’t bid!


I had to take many chances on bidding until I finally won a painting and I was very proud of myself when I finally won. Now I can take these strategies into other auctions and win again! I hope this has been helpful and I hope you win big really soon!




This sponsored blog post was written by Theresa B., proud American and grandmother of two, major MMA fan, writer and ardent practitioner of sarcastic wit. Theresa was compensated by DealDash for this post.