From Debt to Successful Business: Kyle Taylor Shares The Penny Hoarder Story

From Debt to Successful Business: Kyle Taylor Shares The Penny Hoarder Story article image.

We got the chance to sit down with Kyle Taylor—entrepreneur, philanthropist, and the founder & CEO of The Penny Hoarder. Their website has helped millions of people transform their finances, providing articles and videos with the sole purpose of helping people stress less about money.

Here Kyle shares his inspirational story of paying down debt, starting his own company, growing a business, and giving to others along the way.

Living With Debt

Kyle started out like many Americans, dealing with credit card debt and student loan debt. At age 25, he had racked up more than $50,000 between the two.

He started The Penny Hoarder as a way to stay accountable to himself—reporting how much debt he was paying off each month. After the debt was paid, however, he realized he'd built up a following and decided to use the site share other people's stories too.

A Judgement Free Zone For Debt

The Penny Hoarder's approach to personal finance is to make the site funny, smart, interesting, but also non-judgemental. Kyle knows from his own experience getting into serious debt can often come with a lot of shame. The Penny Hoarder name actually was his way of initially blogging anonymously because he was too afraid to tell his friends and family how much debt he had racked up.

"We were taught that you don't talk about politics, religion, or how much money you make," Taylor said. "So it's from an early age you just learn that money is not something you talk about with people.

The stigma can be overwhelming for many. Anytime you admit you messed up, it can be tough. But the reality is that many people struggle with paying down debt.

(The average credit card balance in the U.S. is $6,354 and the average student loan balance is $34,144.)

"We were taught that you don't talk about politics, religion, or how much money you make," Taylor said. "So it's from an early age you just learn that money is not something you talk about with people."

Financial literacy and education is something the U.S. struggles with overall, as only 17 states require a personal finance course in high school. "It's no surprise that personal finance can also be very intimidating.

For a lot of people, it's a complex topic or may even sound a little boring. So we use storytelling as a way of breaking down those barriers a bit," says Taylor. "It's much easier to listen to somebody that's been in your shoes tell you what they did to get out of it than to read a top ten list of things you need to do to fix your finances."

The Origin of The Penny Hoarder

Perhaps the most endearing part of speaking with Kyle was hearing him talk about his experiences growing his business. He took something personal and it didn't even start it as a business originally, but it organically grew into one… and an incredibly successful one at that. The Penny Hoarder is now one of the largest personal finance websites with over 15 million visitors each month, but Kyle's route to success was a bit unexpected in more than one way.

Kyle dropped out of college after his first semester. He was going to school for political science and wanted to work in the White House one day. So he started working on campaigns and for the next seven years, he traveled around the country, just a man and his suitcase. All along the way, he was signing new apartment leases, buying new furniture, and getting rid of it again, and all of that stuff went right on his credit card.

His Advice To Other Entrepreneurs

Kyle says that when it comes to starting your own business, especially in the world of personal finance, it's important to be open and honest, with yourself and others.

"The first thing you have to do is find your truth and then be comfortable sharing it," he said. "You've gotta be extremely honest about your own finances and your own situation because that's how people are gonna relate to you."

The thing that Kyle says surprises him the most is when readers reach out and say they've taken action because of an article he wrote. He also said is that he feels like it took him longer than it should have to make the transition from hobby to business—because of his own fears about it.

Like many entrepreneurs, he was afraid of failing. "I was afraid of hiring somebody and having to lay them off. And so I waited way too long to hire somebody," says Taylor. But he also shares how rewarding it is to have a team around you who cares and is as passionate about it as you are. "People don't believe me when I say this, but I really just look forward to going to work every single day."

His biggest advice includes pushing past your fears and surrounding yourself with smart people to help you. "I don't know that you'll ever truly have that sign that this is time," says Taylor, "but you do have to bet on yourself a little bit. So, for me, it was about 2 1/2 years in, and I was making some progress on the debt. But I still was making $40,000-45,000 a year, so the idea of giving that up just to go for blogging, was pretty darn scary."

He held jobs on nights and weekends when he did start blogging full-time and some of those side gigs would become the fodder for what he'd write about on the site-- at one point he was a beer auditor where he got paid to go to grocery stores around the country and see if they would check his I.D.

He explains that it's important for anyone starting their own business to ask themselves, "Why is it that you're doing this?" Taylor says, "It's probably not to make money, although that is part of why we do what we do. But why are you doing the thing you are doing? There's something else there and that's where I go back to in those moments."

Controlling Your Finances… and Your Life

There's a Buddhist saying that Kyle is fond of: "Don't be attached to the outcome." He admits like many entrepreneurs, he is Type A and he thinks that's kind of why it's so difficult for him to open up.

"We can't control what the other person's reactions are going to be and we're afraid that we're going to be judged." But he also explains, "This is a universal experience. There's not a person on this planet who hasn't had a relationship with money that could use some exploring."

Favorite Stories

We asked Kyle if any stories have stuck with him over the years. He said there are some favorite side hustles he's heard of—like one of their contributors who raises crickets in his backyard and sells them to pet stores. And he's made a killing—over $10,000.

Other favorites are the really heartwarming stories where he learns about The Penny Hoarder making a difference in someone's life. One of their writers recently wrote a story about getting out of an abusive relationship and how finances can make that transition incredibly difficult.

She interviewed some women who had done it, sharing their stories, and a few weeks afterward, they got a letter from a woman who told them that the article helped her get out of her own situation and that she was in a shelter now. "That's how you know how powerful storytelling can really be," said Kyle. "That it can empower somebody to take such a huge leap like that."

From a business perspective, The Penny Hoarder uses stories to generate revenue, Kyle explains.

"There are no display ads on the site. When we work with an advertiser, we tell them our job is going to be to tell your story in our voice. And our writers are just as much guinea pigs as they are writers. So, what they do when an advertiser comes on is try it and then write about their experience. And we find that it's a lot less intrusive than a flashy ad." That authenticity is something other entrepreneurs and companies can learn from—readers connect with them on a personal level.

The Journey of Growing a Business

Every successful business also has to evolve with trends. Kyle sees the future of The Penny Hoarder as a one-stop shop for everything personal finance, which means building more than just a website. They already use social media to reach and connect with people and would love to take things offline as well. Potentially one day, they'll be on TV or even in the classroom.

As a business owner, there are always fires to put out. And there are things you can't expect. One of Kyle's unexpected challenges came in the form of a natural disaster. He shares, "I would never have expected that our team would be out of commission for two weeks because of a hurricane. But when Hurricane Irma came through it was pretty darn scary and most of the team was without power for a while."

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