Kyle Taylor – Founder & CEO, The Penny Hoarder

While managing massive student loans and debt in 2010, Kyle began to blog about his adventures in making and saving money. Readers responded and this culminated into the launch of ThePennyHoarder.com.

Under his leadership, The Penny Hoarder has grown from a personal blog to one of the largest publications on the web with millions of readers a month. The Penny Hoarder has pioneered a new kind of personal finance media with stories about real people and actionable money tips that make a true difference in our readers’ budgets.

Kyle is active in local politics after spending nearly six years on the road as a campaign worker crafting media strategy, directing field workers, and raising millions of dollars for important causes. He feels passionately that people should earn a liveable wage no matter what their job is. In 2016, the Inc. 5000 ranked The Penny Hoarder the 32nd fastest-growing private company and the No. 1 fastest-growing private media company in the United States.

Tell me about your background.
I moved to Florida when I was thirteen for high school. My parents had just gotten divorced. My dad, who had worked for a credit card company for a long time, quit his job and became a tennis pro, and now teaches tennis all over Colorado. My mom is a phlebotomist. She works in the lab at a hospital. So we moved to Florida, and my passion was always in politics. So after high school, I went to the University of South Florida, for an entire semester, and studied political science. During my first semester, I was offered a job on a campaign, and I dropped out of school. For the next seven years, I worked for political campaigns all over the country, living out of a suitcase.

How did the concept for The Penny Hoarder come about?
The thing about working for campaigns is that you’re always out of a job. When the campaign ends, you’re looking for the next gig. So I was doing side gigs, in-between. I went back to school. At one point, at the end of the seven years, I found myself with over $50,000 in student loan and credit card debt, and so The Penny Hoarder really started, part-hobby and part-lifesaver. It was a way for me to hold myself accountable, so each week I would share how much debt I had paid off, and what side gigs I had to add a little extra income to my pocket.

How did you come up with the name, The Penny Hoarder?
I wish I could tell you that there was some beautiful focus grouping that came up with this great name, but it was really just the first thing that came to mind. It wasn’t a business at the time, but it’s come to be known to us as a way of thinking that if you take care of the pennies, the dollars will take care of themselves.

How was the first year?
I wasn’t making enough money from the site, for it to be more than just a blog. I still worked on the side. I had night gigs on the weekends. My favorite job was as a beer auditor. I got paid to go to grocery stores and gas stations, and see if they would check my ID. I could do twenty to thirty of them in a day. I would do those at night and on the weekends, and these side jobs became the father of what I would write about during the day.

Did you ever raise capital for the business?
So far, I’ve still been able to bootstrap the company. I’ve never gone through a funding round.

What were some of the challenges you faced with growing the business?
Two things. First, monetization. I started monetizing the side with display banner ads. What I found is that I had to have an insane number of readers to make even just a small amount of money with banner ads. Finding a business model that worked was one of the initial challenges. And then, finding a group of readers. When I made the transition, two years in, from hobby to business, obviously growing a reader base was extremely important, and I had never done that before. There were a lot of things I’ve tried, and a lot of failures, to figure out how I would get growth there.

I read, in one of your prior interviews, that you were on the Google AdSense blacklist?
I was. At one point. I did lose my AdSense account, which was devastating, because not only was it my business model, but it was also my rent money. It was definitely one of those moments where I questioned whether I should continue, and I thought about giving up. But it ended up being a blessing in disguise because it put me on a path to find something more sustainable, with higher CPMs.

Do you feel like you have a lot of competition?
I didn’t feel that way when the site first started. I actually think that’s why it took off, because a lot of the personal finance websites were catering towards a different audience, people who already had money. I do think that’s changing, and there a lot of large media companies right now that have started sites this year in the personal finance area, so it is getting more crowded.

What has been your marketing strategy?
We always say that we’re not quite a news site, although we do cover breaking news. And we’re not quite a blog, although we do have a very blog-like tone, so we’re somewhere in the middle, and that’s been part of our marketing strategy. We always say that we’re going to make personal finance fun, interesting, and entertaining, often putting the personal in personal finance, even if it’s someone on our team sharing their story of paying off their debt. But we’re still going to employ the same fact-checking mechanisms like every other news site. So finding that middle ground has really been our marketing strategy.

What is an average workweek like for you?
During the time period when the site was just a hobby, there were weeks when I would work on the site for 10 hours, and then there were weeks when I would work on the site for 80 hours, just like any hobby. When the site became a business, but I was still on my own, I was working a pretty standard 40 to 50 hours a week, and now that I’ve opened an office and hired staff, I would say it’s closer to 80 hours a week.

When did the website start becoming profitable?
I’ve been lucky that it’s been profitable since the beginning. There weren’t any startup costs. When the site first started, I couldn’t even afford a domain name, so I started it at ThePennyHoarder.blogspot.com. So I’ve just been able to reinvest revenue each year into growing the site, and I’ve been lucky that it’s been profitable since the beginning. Although in the first couple of years, it was pretty small profit numbers. It was only during the third year when I was able to start taking a salary.

Fastforward to today, how fast is the business growing?
We were able to more than double revenue and users last year. Last year, we did $20 million in revenue and 12 million visitors a month. This year, we’re on track to doubling those numbers again, and we’ll end up with around $40 million in revenue and, hopefully, somewhere around 20 million visitors a month.

How many employees do you have?
We are at sixty-nine employees, as of today.

How do you organize your day?
My day has definitely changed. The larger the company gets, my tasks change. Now, I don’t really spend as much time on the content side, aside from high-level strategy. A third of my time is recruiting, some of that including press. A third is developing leaders here in the company, and helping our executives, and a third of my time is more high-level strategy. In terms of my specific day, I’m an early riser. I usually start around 5 a.m. So 5 a.m. to 9 a.m., is my time to catch-up and get things done. Read the news. I really try to block that time off every day. And from 9 a.m. to 5 p.m., every day, there’s usually a meeting every minute of that time. Generally, with my team, or with job candidates. I try to go home by 5:30 p.m. every day. I think it’s really important to have a couple of hours to unwind and relax. I’m guilty of checking one more time before bed, around 8:30 p.m., then it’s lights out for me.

What kind of people are you looking to hire?
It definitely ranges. I would say 45 employees are content creators (writers, editors, videographers, social media), and then we have a sales team, consisting of six people. We have two people in HR. This year, we’re hiring a lot more on the video side. We’re building a studio, so we’ll be hiring audio engineers and on-air graphics engineers and producers. We’ll be looking to hire those kind of people later in the year.

What are some of your daily habits that have contributed to your success?
As mentioned, I’m a nerd. I love to read. I think that taking time every day to read is something that’s really important to me. Saturdays are “reading days” in our house. We sit around and read magazines, books, as well as briefs that I didn’t read during the week. Not only does it help me gain new knowledge, but it is almost like meditation to me, and calms my mind into thinking about something different.

What are some quotes that you live by?
One of my favorite quotes is by Steve Harvey. I saw him on The Oprah Winfrey Show a while ago, and he said something like, “Stop telling your dreams to small-minded people.” That stuck with me, because I remember when I first started, and I would tell people about this site, like friends and family, I received such a wide range of reactions. Some people get so excited for you, and some people give you that look, like “Oh, that’s great. Nice.” One of my friends, who I love, but would constantly refer to the site as “The Penny Pincher.” It was just little things like that made me believe that they didn’t believe in me. So I love that Steve Harvey quote.

What are some of your favorite books?
One of my favorite books is only about fifty pages called, The Shift from One to Many: A Practical Guide to Leadership. It’s a really quick book about management. It’s one that I’ve reread constantly, because it talks about the different levels of becoming a manager. In the beginning, you’re making every decision, and then the further you move along the path, it’s more about empowering others to make decisions. I read it constantly to serve as a check on myself, and to continue to grow. I also love biographies. I’ve been reading biographies about other people who have started media companies, recently. I started reading a biography about Rupert Murdoch a couple of weeks ago. I just picked up one by Ted Turner, but I haven’t started that one yet.

How do you define success?
I think success is being able to go to sleep at night, feeling good about what you’ve accomplished that day. I don’t think there’s a measuring stick with money, time saved or anything like that. It’s if you feel good about what you spend your day doing.

What is the key to success?
It’s constantly asking yourself if you’re enjoying what you’re doing. Tim Cook had this great quote. He said that every couple of days he looks in the mirror and says, “Did I like how I spent today?” He said if he gets too many of those in a row, where it was “no, today wasn’t a great day”, then he knows it’s time to make a change, in his career or whatever he’s doing.

Did you always know you would be successful?
As humbly as possible, yes! I didn’t know I would be in this arena. I’ve always been very competitive and motivated, and so I knew I wanted to achieve big things, but I had no idea i would be running a media company.

When faced with adversity, what pushes you to keep moving forward?
As I mentioned, I’m very competitive. So I think that competitive spirit is where I really draw all my grit from. The idea that I really don’t want to win. I want to finish.

What is the greatest lesson you’ve ever learned?
During the first campaign I’ve ever worked on, which was for an AFL-CIO for the largest labor union, we were working on restoring overtime laws. This was back in 2004. I learned a lot about culture and how important it was to take care of the folks that work for you, during that time. I think that’s been one of things that’s really helped The Penny Hoarder grow so fast, is that we’ve really invested in the folks that work here, and I’m grateful for that campaign for showing me how important that is.

What do you enjoy doing in your spare time?
Besides reading, I do love to play games. I’m a Mario Kart enthusiast. Video games are the way for me to challenge myself and relax at the same time.

What makes a great leader?
I think great leaders are humble and try to spend their time building others up, rather than just building themselves.

Tell me about one of the toughest days you’ve had as an entrepreneur.
One of the toughest things to do is letting someone go. I remember last year, we had someone on our team, who we all absolutely loved to hang out with, but on the performance side, he was struggling. We had tried to intervene many, many times. It just became clear that it was not the right fit. So we had to let him go. It was not only a tough conversation to have, because it makes you feel awful. It was also tough for the rest of the team, who all loved that person.

Did you do anything afterward to make the team feel better about this?
I’m a believer that sunshine is the cure for everything, and that transparency will win in the end. So we were honest with the team, and didn’t hide the fact that we were letting him go. I always hated that at companies, where people would just disappear and everyone was wondering what had happened. So we had an honest chat with people that this is what happened, and it wasn’t because of anyone else. That it is what it is.

What is your vision for the future of The Penny Hoarder?
Personal finance literacy is very important to me. There’s tens of millions of people, and actually, some surveys suggest that almost half of Americans might have less than $1,000 in their bank account, right now. So our vision, and our mission, is to fix that. It’s to put more money in people’s pockets.

What do you think is the most common mistake entrepreneurs make?
Not letting go. It’s one of the more challenging parts of becoming an entrepreneur. The larger the company, and the larger the team gets, the more you have to be comfortable with people making their own decisions.

What advice would you give to young entrepreneurs?
Don’t quit your day job. I want to encourage entrepreneurship, but I believe, sometimes, entrepreneurs have this TV version of what should happen. You go out and raise a bunch of money, quit your job, and go full blast as an entrepreneur. Well, there are other ways to do it. It can start as a side gig, and maybe it will grow a lot slower, but odds are you’ll be able to pay your rent that way.

This interview was conducted for research purposes by Jason Navallo for his upcoming book, Underdog.