Day: October 19, 2025

• Rising Stars of Wall Street share how they spent their first big paychecks.
• 10 stars shared how they rewarded themselves for years of hard work.
• Some prioritized family support or savings, while others indulged in personal luxuries.

What makes those first internships and analyst years — spending long hours poring over financial models and spreadsheets, drafting investment memos, or staying at your desk well past dinner time — worth it? The first real payday.

Business Insider asked its Rising Stars of Wall Street to remember that moment and share what they did with their first big check. For some of these successful financiers, the funds went straight to family or savings, while others chose a little indulgence or a big experience.

Here’s how 10 of them spent it.

Sharing with the family

Nikunj Jain, head of Asia research at Bridgewater Associates

“I actually sent it all back to my grandparents, my family back in India. They’ve been a huge source of support and guidance.”

Christian Woo, Bank of America managing director and quantitative strategist

“I bought a ticket back home to Hawaii, and I spent a couple of weeks with my family. My whole family and extended family are still based there, and I hadn’t been home in a while.”

Catherine Kress, the chief of staff to BlackRock CEO Larry Fink

“I’m quite frugal from a spending perspective. So I never really spend much on myself. But after I got my first big bonus at BlackRock, I took my parents and my husband to dinner at Blue Hill.”

Little luxuries

Jessica Shill, a portfolio manager on the securitised credit team at Janus Henderson

“It was at Wells Fargo. I was sitting next to one of the more senior analysts on the team, and she encouraged me, ‘You’ve got to get yourself a bonus gift, a treat yourself gift.’ I love skiing, so I went out and bought myself a new pair of skis.”

Mohini Chakravorty, a principal in Blackstone’s infrastructure group

“My mom has always encouraged my brother and me to make one exciting purchase for ourselves post-bonus, especially in the early years. It’s important to reward yourself for hard work. I remember buying an expensive purse with my first bonus and bringing it to work every day.”

Knut Kirchoff, a Blackstone principal in its credit and insurance unit

“I grew up racing, so getting my first pair of skis here in the States was what I did.”

The savers

Sarah Naylor, a credit salesperson at Citadel Securities

“I just got very excited and put it all in a savings account — and was excited to finally see some zeros in a bank account.”

Mary-Grace Papatheodorou, a Morgan Stanley managing director

“I saved a lot of that money and bought my first apartment by the time I was an associate. I took a bit more of a long-term perspective, and I decided I wanted to buy my own place rather than rent.

“It was a small one-bedroom in Murray Hill, in a convenient location for me.”

Time to travel

Lamar Cardinez, a Principal at Blue Owl Capital

“We got married my second week into my summer internship…. we actually had to go on a delayed honeymoon, and my wife was so gracious, never had a negative word to speak during that kind of delayed honeymoon period.”

“I used that money to book a trip to Maui, which to this day was maybe the most amazing experience in a place that I’ve ever visited with my wife.”

Florian Plath, an executive director in mergers and acquisitions at JPMorgan Chase

“I actually treated myself to a new adventure in Mexico. I started in Mexico City, I saw the pyramids, I saw the ruins, I swam in the Senotes, which was an incredible experience.”

• 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.