Ending Soon! Save 33% on All Access

I've Had a Secret Side Hustle for Decades. It Keeps Tens of Thousands of Dollars in My Pocket — and Gets Me Into Places I Wouldn't Go Otherwise. When Cliff Smith lost his job, he picked up an under-the-radar gig that would make it possible to keep dining out — something he and his wife love to do.

By Amanda Breen Edited by Jessica Thomas

Key Takeaways

  • Smith and his wife first heard about the EyeSpy side hustle from friends who knew founder Mistie Boulton.
  • Smith started with the company over two decades ago; these days, he completes about three evaluations each month.
  • Since he began keeping track in 2008, Smith has enjoyed a $40,000 food budget in exchange for his reviews.

This as-told-to essay is based on a conversation with Cliff Smith. Smith is based in Palo Alto, California and has been an evaluator for EyeSpy Critiquing & Consulting since 2003. The piece has been edited and condensed for clarity.

I started working as a mystery diner with EyeSpy over 20 years ago. Our friends knew the founder Mistie Boulton, so they were among the very first people to do it, and when they told us about it, we thought it sounded too good to be true — to have our meals at nice restaurants paid for in exchange for writing up the experience. We didn't jump on the opportunity right away, but when I lost my job and began to tutor GMAT prep, I picked up the side hustle so we could continue dining out.

Typically, I complete around three evaluations a month, and the work takes me to fine dining establishments as well as more casual restaurants; sometimes, the evaluation will even be for a takeout order. One Saturday last month, my wife and I did a brunch evaluation at The Village Pub, and our budget for brunch was $250 — and we needed it. We actually went slightly over with the tax and tip. The following Friday, we got a pizza delivery. So it remains a mix, and that's one of the advantages: This side hustle gets you into places you might not go otherwise.

Related: She Used Her Kids' College Fund to Build a Side Hustle, But the Product Was 'Unsellable' — Here's How She Got Back on Track for $100 Million in Sales

The process usually starts when you receive an email, then you go to the website and see that you have an assignment. You can negotiate when to do the assignment within the month, and if you can't do it that month, you can explain why and potentially take on the assignment the next month, but you may not get it again. It depends on what's going on — sometimes if they already have someone for the following week, it doesn't work out.

For each evaluation, there's an online survey form, and they do differ. Different restaurants care about different things. For example, The Village Pub cares a lot about how they handle the wine. Do they observe proper protocol? Do they keep filling your glass? Other places don't care nearly as much about that, but they might care about how many people say goodbye to you. So before an evaluation, you really do need to look at the form. Even if it's a similar kind of restaurant, the management may care about different things for different reasons. And you're supposed to remember when they did different things. I take pictures so I have a timestamp for all of it.

Related: This 29-Year-Old Left His Marketing Job to Pursue a Side Hustle — Now He Earns Nearly $200,000 a Year: 'So Attracted to the Adrenaline Rush'

You have to turn in the evaluation within 24 hours. When we started, it was two days, but they changed it to the next day. And in a way, that's reasonable because you have to remember a lot, and it does fade. The time it takes to finish an evaluation depends on the place. For the pizza place I mentioned, I completed it that night and maybe spent two hours on it at most. But I probably spent about six hours on The Village Pub evaluation. I wouldn't do it all in one day for a place like that.

We also have to submit photos. I use Photoshop to crop them because I'm surreptitiously taking the pictures — though it doesn't have to be too surreptitious because a lot of people are taking pictures these days — but I take so many that I don't want to be too obvious about it. I don't take great pictures all the time. For the food, I do, but for the other things, not so much. But I may take a picture of the table to show the place settings if they care about their positioning. Later, when I'm submitting the photos, I need to crop them so they look better, and I reduce the rest so I don't bring the EyeSpy server to its knees.

Since July 2008, I've tracked how much I was budgeted for each evaluation — and it comes out to $40,000 in total. Of course, the real number is higher than that because we started the side hustle in 2003. And, of course, the cost of dining out has increased over the years. My favorite part of being a mystery diner is the ability to go places we wouldn't otherwise; it gets us into restaurants like The Village Pub, where we just wouldn't spend that kind of money on a dinner, let alone a brunch. We also try places we might not normally try. We go to Oren's Hummus, which is owned by the founder Mistie Boulton, all the time, but before working with EyeSpy, I'm not sure if we'd ever had Middle Eastern food.

Related: I Started a Semi-Passive Side Hustle That Earns $33,000 a Week on Amazon: 'Selling There Is a No-Brainer'

I also appreciate that I really have a voice. Generally, if you go to a restaurant and they treat you badly, you might ask to speak to the manager, and maybe you get comped or you get a free dessert. But I have a nuclear weapon. If I note that something isn't right, there probably will be a change. This wasn't vindictive, but one time, we went to a nice bistro in San Francisco, and our server just wasn't very accomplished. It wasn't a deal-breaker that would keep us out of that restaurant in the future or anything like that, but things weren't smooth or well done. A few months later, we went back to the same restaurant, and that same server was there, but now she was an assistant server, not the main server. So I thought, Well, they listened. And she seemed to be okay doing that; it was a better fit for her skill set. It's gratifying to know that I'll be heard because the restaurant management paid to hear it.

Amanda Breen

Entrepreneur Staff

Senior Features Writer

Amanda Breen is a senior features writer at Entrepreneur.com. She is a graduate of Barnard College and received an MFA in writing at Columbia University, where she was a news fellow for the School of the Arts.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Business News

TikTok Reportedly Laid Off a 'Large Percentage' of Employees as the App's Fate in the U.S. Remains Unclear

Laid-off TikTok employees were notified Wednesday night through Thursday morning.

Personal Finance

This Investment Bundle Includes a Trading Course and Stock Screener Tool for $150

Approach the stock market with an increased understanding.

Business News

Four Seasons Orlando Responds to Viral TikTok: 'There's Something Here For All Ages'

The video has amassed over 45.4 million views on TikTok.

Growing a Business

5 Strategies to Know As You Scale Your Business

Scaling a service-based company requires a comprehensive approach that goes beyond simply increasing revenue. It requires careful planning, strategic decision-making and a deep understanding of market dynamics.

Growing a Business

The Right Way to Ask Someone for a Million Dollars, According to a Fundraiser Who Does It For a Living

No matter what you're raising money for, Wanda Urbanskia says, the same basic rules apply.