Justin Cupler - The Penny Hoarder

As the father of two young boys whose wife has taken on the thankless and demanding job of being a stay-at-home mom, I need to hoard pennies whenever I can.

Thanks to my wife’s insane couponing skills, grocery shopping is one area we save big on, though we can always improve.

To stretch our budget even further, I decided to try mystery shopping at grocery stores for a month.

I thought we would take our couponing to a new level. I thought I’d put in a few hours’ work on weekends and earn $50-plus, along with tons of extra free food.

I’ve been wrong before — but rarely have I been this wrong.

How I Got Started as a Mystery Shopper

[caption id="attachment_48962" align="aligncenter" width="1200"] Penny Hoarder assistant editor shops at a Hudson, Fla., Winn Dixie. Sharon Steinmann/The Penny Hoarder[/caption]

When I decided to try mystery shopping, I did a quick search and found TrendSource. The company reimburses mystery shoppers $9 per trip, plus pays $4 — all just for doing the shopping we’d be doing anyway.

The downside: TrendSource only partners with one grocery store in my area, and this store is a little less coupon-friendly than Publix, our go-to store. But still, it was free groceries, so whatever!

On the surface, combining this reimbursement with our couponing sounded like a win-win — but I quickly found it wasn’t as easy as I’d hoped.

Evidence: the whopping $28 I made in a month of mystery shopping last November.

If you’ve ever wanted to make money as a mystery grocery shopper, read on as I share where I went wrong, as well as a few things I got right. Maybe, if you learn from my experience, you’ll have better luck than I did.

4 Mistakes I Made as a Mystery Shopper

[caption id="attachment_49067" align="aligncenter" width="1200"] Shoppers check out a brand new Winn Dixie supermarket in Tampa, Fla., on Oct. 21, 2016. Samantha Dunscombe/The Penny Hoarder[/caption]

While I made a little money and got tons of free groceries as a mystery shopper, there were plenty of areas for improvement. And some of my processes needed an outright overhaul. Here’s what I did wrong.

1. I Failed to Plan

Full disclosure: I tend to be a fly-by-the-seat-of-my-pants kind of guy. Sure, I’ve gotten better at planning in my professional life, but my personal life is a completely different animal. And oh did that shine through like a beacon of irresponsibility when I played mystery shopper.

To be perfectly honest, I did plan my first route. I went on Google Maps, plunked in each store’s address and carefully shifted them around to create as perfect a circle as I could. On the trips that followed… not so much.

Because of the limited number of stores in my Podunk town, I had to drive to various surrounding cities – some as far as 35 miles away – to maximize our grocery hauls. It required a lot of that aforementioned skill I so lack in my personal life: planning.

On the last few runs, I hastily rounded up my wife and kids, and shuttled us to each store without plans. My lack of planning resulted in our crisscrossing Tampa several times — and anyone familiar with Tampa’s size and traffic patterns will know what a time drag this could be.

Had I thought it out, I would have mimicked my first shop and created a clean circle that began and ended with my house. Live and learn, right?

My Advice: Use Google Maps to plan your route as a circle that leads back to your house. Try to fit the longer journeys in with other things in that area, like going to a park or visiting family.

2. I Didn’t Keep My Questions Simple

[caption id="attachment_48961" align="aligncenter" width="1200"]Mystery shopper Penny Hoarder assistant editor shops at a Hudson, Fla., Winn Dixie. Sharon Steinmann/The Penny Hoarder[/caption]

This was huge: As a crafter of words and a wannabe actor/broadcaster, I insisted on improvising each shopping trip. I didn’t want to tip off store employees that I was a mystery shopper.

In an attempt to be as customerlike as possible, I asked some VERY open-ended questions. Example: “What would you suggest for a kid’s birthday party with about 50 guests?”

In many cases, the employee really didn’t care about my issue and hardly gave me a head nod. But occasionally, I asked a question to the wrong employee (aka, a good one), who proceeded to discuss countless options with me.

When I asked a woman in the bakery the aforementioned boneheaded question, she spent 30 minutes — I swear! — talking to me about color, sizing and toy options for various cakes. For Pete’s sake… All I wanted to know was the price and options for the dang cake!

Good for her for acing the test. Bad for me spending 30 minutes discussing the inner workings of cake decorating and toy placement. What’s worse, this was only one of seven interactions I had to have with store employees on the trip... gulp.

Had I known how few employees actually cared that I could potentially be a mystery shopper, I would have scripted one simple question for each department.

My Advice: Create a simple script filled with yes-or-no questions to ask each employee you interact with. It’s their responsibility to take the conversation further, not yours.

3. Two Adults Are Efficient, but Bringing Our Two Kids Canceled Us Out

[caption id="attachment_49068" align="aligncenter" width="1200"] A receipt from a new Winn Dixie supermarket in Tampa, Fla., on Oct. 21, 2016. Samantha Dunscombe/The Penny Hoarder[/caption]

I love my kids… I swear, I really do. But even the best-behaved children can somehow make a day at Disney feel like a 50-year sentence in a torture chamber. And without a babysitter, the kids had to come with us — you know, police frown upon leaving a 19-month-old in the care of a 5-year-old.

If you’re seriously interested in becoming a mystery shopper, my first piece of advice here is to bring in your partner (if you’re so lucky to have one). I did just that with my couponer-in-crime wife. But leave the kids behind.

On our longest stretch, we drove from store to store for about eight hours. By about hour four, my 19-month-old had been through enough, and out came the waterworks. My 5-year-old was a tad more patient, but by hour six, he couldn’t resist the power of “I want” and began asking for the store's signature free cookie every few minutes.

Then, there were the completely random “I gotta pee” moments that came after we’d literally just left the store.

Keeping the kids calm and entertained didn’t just add time to our shopping trips; it made them much more stressful.

My Advice: Get a babysitter, or fly solo while your partner watches the kiddos.

4. I Missed My Deadline

As I said before, I am not the best planner in the world, and here’s how that showed up again. TrendSource gave me 12 hours to submit my final paperwork, and I did fine initially.

But remember what I said about leaving the kids at home? Imagine roaming the aisles of your local grocer with a wailing 19-month-old, a 5-year-old who’s asking every 30 seconds if we’re done, and your poor wife who’s long over it — yet she’s still trying to help you keep your mind so you can complete the mystery shop.

Yeah… I wasn’t at my greatest. I just wanted to hide out in the beer and wine section for a few hours.

Plus, I was completely discombobulated after driving from my home in Hudson, Florida, to Dade City, then Tampa and, finally, back home to hit two stores — a 100-mile circle.

In my exhaustion, I completely muffed the submission side, telling myself, “Eh, I’ll submit it later.” Well, “later” I was fast asleep and didn’t wake up until the next morning.

Waiting for me was a nastygram telling me that because I failed to log my work within 12 hours, TrendSource had deducted $1 from my $4 earnings.

A buck doesn’t sound like much, but when the total fee for the project is $4? That’s huge!

My Advice: Always, always, always plan to log everything as soon as you leave the store or once you get home, no matter what.

4 Mystery Shopping Wins

[caption id="attachment_48960" align="aligncenter" width="1200"]Mystery shopper Penny Hoarder assistant editor shops at a Hudson, Fla., Winn Dixie. Sharon Steinmann/The Penny Hoarder[/caption]

I wasn’t a complete failure as a mystery shopper, but my successes were far fewer than my missteps.

1. I Used the App

Not all mystery shopping companies have this, but TrendSource does, and was it ever a lifesaver!

The app allowed me to avoid downloading and printing mystery shop questionnaires that were six or more pages. (I did print a few before I realized there was an app, though.) This also allowed me to quickly enter my feedback after completing each segment without whipping out a clipboard and blowing my cover in the middle of the store.

The app, though a bit clunky in some respects, made the entire submission process so much smoother. I could snap a picture of the receipt, enter my grand total and submit the questionnaire for verification all on my smartphone. It’s the only right way to get this done.

2. I Maximized My Hauls With Coupons

My wife and I are serious coupon addicts… We often save 90% or more on groceries and sometimes even get money back. So why not use coupons to make the $9 reimbursement go even further?

I scoured TrendSource’s FAQ and found nothing that said we couldn’t use coupons, so we decided to give it a try. We got far more than our allotted $9 worth of goods. In fact, we got $50 or more in groceries, and we were able to grab things that coupons aren’t usually available for, like milk and eggs.

We walked out with nearly free groceries: We spent an average of $11 per trip, and TrendSource credited us $9 per transaction.  

3. I Earned Cash Back

My wife and I recently converted to paying for nearly all our expenses, including groceries, on a Disney Rewards credit card, which gives us 2% back in Disney rewards at grocery stores. Averaging $11 out of pocket at the seven stores we hit, we ended up with a whopping $1.50 in rewards – enough to pay half the cost of a bottle of water at The Happiest Place on Earth.

If you don’t have a rewards card or want to up your savings even more, you can always hit a discount gift card site like Raise and pick up a card for the store you’re shopping at.

Had we done this, we could have saved up to another 1% on the gift card, plus the 1% cash back Ebates offers on Raise orders. If you have a rewards credit card, you can use it to pay on Raise and get those rewards, too. This is a pretty deep stack, but the extra savings are well worth it!

And don’t forget to check out what you can get in cash back on from Ibotta. Just snap pictures of your receipts, and let the cash flow back into your account.

4. I Bought Items With Fuel Rewards

Gasoline is the second-largest drain on my bank account that doesn’t have a roof over it, so my wife and I maximize fuel rewards (thanks, Fuel Rewards Network). Because the stores I shopped were FRN partners, we made sure to shop mostly products with additional fuel savings.

At the end of our first group of stores, we’d earned 75 cents off per gallon. Holy 1999 gas prices, Batman!

Sure, you won’t realize these savings immediately, but you’ll be happy you did this next time you fill up.

The Payoff Wasn’t Worth It to Us

Through all this craziness, my wife and I decided regular mystery shopping simply wasn’t for us.

Yes, we hauled in a good amount of free groceries. But the hauls weren’t significantly better than what we would have gotten through our normal couponing. Considering that we only made $28 in actual pay, we just didn’t feel it was worth the time or fuel. (If a mystery shopping gig opened up at a store near our home, we would still probably take advantage.)

That said, there are plenty of people who enjoy great success as mystery shoppers — including The Penny Hoarder founder and CEO Kyle Taylor.

From my experience, I believe this side hustle is perfect for folks without kiddos and with a lot of spare time -- but neither of those describe my family. My family’s busy lifestyle got in the way, which is why our mystery shopping days are over for now.

Justin Cupler is an assistant editor at The Penny Hoarder. He never passes up a chance to make some extra cash and save on groceries.  

Disclosure: We don’t hesitate to pick pennies off the sidewalk when we spot them. But the affiliate links in this post help our earnings grow even quicker. Plus, it’s a lot cleaner than sidewalk money.