Day: October 19, 2025

• I tried OpenAI’s new ChatGPT shopping feature for gift ideas.
• It’s a cool concept, but I found limitations in the functionality.
• Here’s how it did at helping me find a gift for my mom’s birthday.

A new shopping feature on ChatGPT dropped just in time for my mom’s birthday.

However, I’m not convinced it can help me find the right gift.

OpenAI said September 29 that it was introducing a new shopping feature called Instant Checkout that would allow US-based ChatGPT free, Plus, and Pro users to search and purchase items right in their chats. For now, it’s available on items from Etsy, with Shopify merchants, like Glossier, Skims, Spanx and Vuori, coming soon.

The ChatGPT maker, whose CEO, Fidji Simo, hails from Instacart, seems to have big plans for shopping. It struck a deal with Walmart that will soon allow people to make purchases from the world’s largest retailer directly within the app. Other companies, including delivery apps Instacart and DoorDash and retailer Target, are also building shopping experiences within the AI chatbot. Some people also use ChatGPT as a shopping assistant, comparing things like price and style across brands and retailers.

With more shopping experiences to come, I decided to try out ChatGPT’s Instant Checkout feature.

You can’t go wrong with jewelry as a gift

For her birthday, my mom wants a mixed-metal bracelet made with sterling silver and gold, and I set a budget of $400. Etsy sounded like a good place to find unique handmade jewelry for her gift.

So, I followed my chatbot’s instructions by simply asking it to “show me handmade silver and gold bracelets on Etsy.

It asked for more details, such as my budget and style preference. It then pulled up a list of seven options available on Etsy.

This is where I started to wonder if I was doing something wrong. The options had links next to them that would take me to their Etsy listings, but there was no button for buying directly on ChatGPT. Not to mention, one of the items it suggested was a $2,400 bracelet cuff — much higher than the budget I gave.

It asked if I wanted it to narrow down the search to only include items with the in-chat “Buy” feature available, to which I said yes.

“I tried to find listings that support Instant Checkout in ChatGPT, but I couldn’t reliably tell from product data whether each one is eligible,” it replied, with bracelet style suggestions.

The items have to be eligible for Instant Checkout

ChatGPT gave me a list of requirements that would make an item on Etsy available for Instant Checkout:

• Only US users can currently use ChatGPT’s Instant Checkout for Etsy.
• The listing must be from an Etsy seller who participates in Offsite Ads (those are the sellers whose listings can be “instantly purchased” in ChatGPT).
• If the product shows “Visit” instead of “Buy,” it’s not eligible for Instant Checkout.

The second requirement made it clear that availability on ChatGPT was up to each Etsy seller, not the marketplace itself. It was then that I realized that it would be harder than I thought to track down an Instant Checkout-eligible bracelet.

I tried a couple of other partners, like Skims and Glossier, to see if they’d rolled out yet since the announcement was about two weeks ago. No luck.

It was time to change strategies

I widened my search and asked ChatGPT to find necklaces on Etsy instead. I got the same results. Although OpenAI’s press release said the feature is already out for US users, I asked ChatGPT to confirm that it was available to me.

When it was confirmed, I asked it to find a few examples of items available to purchase through ChatGPT. Again, no luck.

“I couldn’t reliably confirm any specific items right now that definitely support ‘Buy in ChatGPT / Instant Checkout’ from Etsy,” the chatbot said.

I contacted OpenAI to see if it might be user error, and didn’t receive a response.

I resorted to using ChatGPT to find recommendations for necklaces rather than use a search engine. I was pleased with the results.

The chatbot gave me ideas for places, like Etsy or Nordstrom, to find mixed-metal cuff bracelets. I got more specific by asking for brand names, and it listed places like Cartier, Pandora, and more, with pros and cons.

I then told ChatGPT to find me items across retailers that match my criteria and are available for purchase. It gave me a list of bracelets from brands including Kendra Scott and Mejuri, all of which fit what I was looking for — though I had to prompt it again to give me direct links to the product listings. I wasn’t in love with any of the options, though.

I ended my search there, with my cart empty and the search for the right bracelet continuing elsewhere.

• Nicole Shirvani is a full-time psychiatrist who invests in real estate on the side.
• She used a 1031 exchange to avoid capital gains tax and scale her portfolio.
• Her investment properties help boost her savings, support travel, and secure her daughter’s future.

Nicole Shirvani experimented with rental real estate in her 20s — buying a condo in Toronto, where she’s from, and filling it with a long-term tenant — before taking a step back to focus on medical school.

“As a student, you’re not really making a lot of money, so I kind of put that to the side,” the psychiatrist told Business Insider. “After I finished training, my job gave me an opportunity to save some money, and I thought, ‘How can I invest in something that would appreciate and grow, and also allow me to save more for the future?'”

Real estate checked both boxes, providing both monthly cash flow and price appreciation.

Shirvani started looking for investment properties in southern Oregon, where she moved after getting her degree. In 2018, she closed on a duplex close to the hospital where she was working.

One of the units was already rented to a traveling nurse, while the other had just been vacated. She spent about six weeks upgrading the vacant unit before finding a new tenant. Once both units were filled, she said the cash-on-cash return was between 15% and 20%.

Using a 1031 exchange to sidestep capital gains taxes and scale her portfolio

In 2022, Shirvani accepted a job in Florida and decided to sell the Oregon duplex. Typically, when you sell an investment property for more than you paid for it, you’ll owe tax on the difference: either short-term capital-gains tax (if you held the property for a year or less) or long-term capital-gains tax (if you held the property for more than a year).

However, a 1031 exchange, also known as a “like-kind exchange,” is a strategy that allows investors to defer capital gains taxes on the sale by reinvesting the proceeds into a new, similar property that is of equal or greater value than the relinquished one.

There are a few rules to consider: 1031 exchanges are intended for investment properties, not primary homes; you need to hire a qualified intermediary to handle the transaction; and you have a limited amount of time to complete the exchange.

As soon as you sell, the clock starts: You must identify your replacement property or properties (you can identify as many as three like-kind properties) in writing within 45 days of selling the first property.

Then, you must close on the replacement property within 180 days of your initial property sale.

Shirvani, who traded in her duplex for two properties in Florida — a beachside condo and a single-family home — said the timeline was “a little bit stressful, but the market was still fairly busy.”

She also started looking at exchange properties before listing the duplex to give herself plenty of time.

“Before you sell, try to have the replacement properties identified and line everything up,” she advised. “You don’t want to sell a house, not be able to find suitable properties, and be stuck, unable to invest that money into something.”

Shirvani, who has since added two short-term rentals in the Shenandoah Valley and a triplex in Lakeland, Florida, to her portfolio, plans to use the same strategy as she continues scaling.

While she doesn’t plan on fully retiring early, she’s using the rental income to boost her nest egg so she can eventually scale back at work. She’s also using the income stream to save for future expenses.

“It’s allowed me to save more money, be able to travel, and put money toward my daughter’s future,” she said. “And then, eventually, I’ll be able to leave that real estate for her.”