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How This Successful Side Gigger Paid Off $50K and Built a $20M Business in Six Years

Molly Triffin

Kyle Taylor will never forget the moment when he hit rock bottom. At age 23, he was earning a good salary of $40,000 as a political campaign manager, but he was drowning in more than $50,000 of debt—$30,000 from student loans and $20,000 in credit card debt.

In the summer of 2009, he found himself out of work for several months in between campaigns. “I had collectors calling every few minutes, and it all came crashing down on me,” Taylor says. “I was looking for change on the side of the road in order to buy ramen for dinner.”

Although his parents had bailed him out before, he couldn’t bear the embarrassment of asking for help again. He wanted to turn things around for himself.

And he has. Today, Taylor’s not only debt-free—after negotiating his bills, consolidating his debt and finding new streams of income—he’s the CEO of The Penny Hoarder, a money site he founded in December 2010 that now brings in more than $20 million in annual revenue. Here, he shares his best side gig tips, the book that changed his life—and how to get paid for drinking beer. (Believe it.)

How did you bounce back from being broke and in debt?

I had to come to terms with how much debt I’d racked up [and have] an honest conversation with myself about my spending problem. For the first time, I started to take responsibility and got real about budgeting.

Every Sunday, I sat down to review the week’s progress and make little changes for the next week. I would make dinner and have a glass of wine while I looked over the numbers. This shifted it from a negative experience into something fun.

What was the genesis behind The Penny Hoarder?

I started the site as a hobby as soon as I recognized how much debt I had. I always had a knack for finding interesting side gigs, so I thought it might be fun to share some things I was doing. I also thought it would be a good way to hold myself accountable.

Which of your side hustles were lucrative, and which didn’t pan out? What advice do you have for people who want to make extra cash?

One of my favorites was working as a beer auditor. I’d buy beer at grocery stores and gas stations and see if they asked for my ID. I would go to 20-25 places a day and was paid $10-$40 per location. Plus I had lots of free beer to give away!

On the not so lucrative side, I played the drugstore game [where you use a combination of coupons, sales and reward points to score free items at drugstores]. I tried to resell things like a pack of razors or deodorant on eBay. When I accounted for my time and the cost of gas, I was making less than minimum wage.

I recommend finding a side gig you enjoy doing. If you use your hobbies as a way to develop a gig, it feels less like work. I also suggest looking for gigs that involve the whole family, like mystery shopping [where you’re paid to report on your experiences at certain businesses].

What money lessons did you learn growing up?

Oftentimes, people focus either on side gigs or frugality. My parents taught me to focus on both. My mom made a chart of our electric usage and us kids would take turns going out to the meter to see how much we’d used the day before and then challenge ourselves to do better, like by turning off the lights.

My parents also did a good job of involving us in side gigs. If we were going to have a garage sale, we were coming up with the pricing and getting it set up. My parents would have us practice negotiating with people who came by.

What’s the biggest financial mistake you’ve made? 

Thinking that spending money was going to bring me some level of happiness. I’ve since discovered that knowing you can buy something feels a lot better than actually buying it.

Best financial advice you’ve gotten?

Pay yourself first, from David Bach, who wrote “The Automatic Millionaire.” People usually start by paying their bills and living expenses, and then put aside whatever’s left over for retirement. Instead, invest in your future first. I started doing this a couple of years ago. Now, I automatically put money from my paycheck into my 401(k).

What money rules do you live by now?

I automate as much as possible, whether it’s bill payments or deposits into a retirement account. Because the money comes directly out of my paycheck and I don’t even see it, it helps prevent me from making a mistake.

I also look for ways to increase my income, like by having a mini business on the side or earning money for things I’m already doing. Until recently, I had a retail arbitrage side business, where I’d buy things on sale at stores like Toys R Us and sell them on Amazon for a profit. If I shop online, I always use a cash-back agent like eBates. It only takes 10 extra seconds to save money.

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