Deal Hunter Profile: Kyle James, Founder of Rather-Be-Shopping

We made SimplyCodes for the best of the deal-hunters. Ones who not only are smart shoppers, but community members who share their secrets to save more together.

One of those deal-hunters is Kyle James, founder of Rather-Be-Shopping.com — where he shares everything from shopping hacks, insider and frugal living tips, and secret menus to job opportunities and how to maximize return policies. 

Kyle’s story: It all started with a coupon code

What is your professional background and what inspired you to start the website more than 20 years ago?

I have a MBA, but I have always been drawn to computers, even from an early age. So when I was a pharmaceutical rep back in 1999, traveling like crazy and in hotels two weeks out of every month, I started researching online business that I might be able to create.

Then when Christmas shopping online, I saw the "Coupon Code" box when checking out from BestBuy.com and it changed my life. I looked to see if there were many coupon websites around for people to use and save money, and the idea for Rather-Be-Shopping.com was born.

Then in 2009, I got really bored with only adding and removing coupons everyday, so I started my blog as a fun way to be creative and find, shall we say, out-of-the-box ways to save money. It became popular because I write about actionable ways to save money, like menu hacks at Starbucks, clever ways to save at the grocery store, and how to look at a price tag and figure out if it's a good deal or not.

How did you go from that first day in 2000 to figuring out how and where to get the best deals?

I literally just threw up a crappy website that I created with MS FrontPage and started listing online retailers. Then I signed up for their coupon alerts and newsletters and started adding coupons when I found them around the web or in my inbox. I had no idea what I was doing. Then I started getting traffic from this new search engine with a really weird name called “Google” and the rest is history.

Kyle’s saving methods: From eBay to Amazon

How do you find a great deal?

It's pretty simple — always price compare and look for a coupon, then check eBay for an even better price on a slightly used version. If I'm not saving at least 40% off the retail price, it's not a great deal. I often find products for 50-80% off the retail price and literally save hundreds, even over $1,000, around Christmas and my kid's birthdays.

Has that changed over the last few years dealing with a pandemic, inflation, etc.?

No, not really. The price of stuff has definitely gone up, but the percentage of savings I usually find has stayed the same. If anything, inflation has made me a more diligent deal hunter. I'll never hit "Buy Now" on Amazon without looking for a better price first. Never get lazy and start shopping exclusively on Amazon because you're getting ripped off on many of their items.

What is your shopping process like? Are there certain websites and tools that you use on a regular basis?

Too many to name really. I use CamelCamelCamel to set up Amazon price alerts on expensive purchases so I only buy when the price is the lowest.

I always scan my grocery receipts with the Ibotta app and Fetch Rewards app and score free money in the form of gift cards just for buying the stuff that I'd be purchasing anyway. Also, I always start my online shopping on Google Shopping, as it gives me quick price comparisons to a bunch of major (and smaller) retailers.

Kyle’s advanced deal hacks: Best practices

How do you know you’ve found the best deal possible?

Here's my rule of thumb....if I spend five minutes researching a price, looking for a coupon, etc., and I can't find a better deal, then I know I'm getting the best deal available.

What do you consider your “Olympic gold” in terms of the best deal you ever found and how did you find it?

Tough one. Probably the $700 air hockey table that I scored for $55 at Sports Authority on Black Friday a few years ago. The box had some rips in it and I simply asked for the price I wanted to pay, as I was taking a risk, and they gave me the deal. Sometimes you just have to ask, especially on Black Friday when stores want to clear out merchandise.

In general, with three kids — all of whom play sports — we are constantly buying what they need. I have no idea how much I've saved, but it's in the thousands for sure.

What do your friends and family think about your deal-finding passion?

They think I'm a weirdo who's obsessed with saving money and using coupons, but then when I tell them about some of the deals I've found, they think I'm a complete freaking genius.

What do you think the biggest mistake people make in terms of shopping and overspending on certain items?

Not looking for a better price by putting convenience over money. Amazon is the perfect example as they've been slowly raising their prices for years, but many Amazon loyalists never price compare or look for coupons. They just happily pay whatever Amazon is asking. Boo! Never do this.

What are your top tips you would give our readers who are looking to save money?

1. Never assume the price is final - Did you know you can negotiate the price at most major retailers? You just have to have a reason to ask for a lower price and know what to say. 

2. Instead of shopping at Amazon, look for Amazon liquidation stores in your area and save big on Amazon returns. Do a quick Google search for “Amazon liquidation store TOWN NAME” and you'll quickly find any in your area. You can save up to 90% off the original Amazon price on electronics, small kitchen appliances, and tools. 

3. Always look for a price match - Most shoppers will never ask for a price match when they find a competitor’s lower price, simply because they don't know how price match policies work. If you’re not doing your homework and looking for the best price, then you’re losing out big time, as many large retailers will not only price match, but some will even beat a competitor’s price by 5-10%.

What’s something people don’t know about you? 

We have a Pygmy goat named Larry here on the James' farm. He had a friend named Chuck, but he passed away last year, so now it's just Larry waddling around looking for something to eat. It's a good day in his life when we have stale bread or tortilla chips in the pantry. Larry's eating good tonight!

Eager for more deal-seeking advice? Start here

As part of our mission to never miss a deal, the SimplyCodes team absorbs teachings from the best of the best — to continue learning how to save like a pro from discounting deep-dives and deal-hunter profiles, check out the SimplyCodes blog!