Podcast: Penny Hoarder Founder on Mission-Based Work, the Gig Economy and Entrepreneurial Success

Kyle Taylor
Episode 15 of the NewRetirement podcast is an interview with Kyle Taylor — founder of The Penny Hoarder — the fastest-growing private media company in the U.S. for the second consecutive year. We discuss how mission-based work, the gig economy and millennial financial practices could be applied to entrepreneurs and achievers of all ages.

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Full Transcript of Steve Chen’s Interview with Kyle Taylor

Steve: Welcome to the NewRetirement podcast. Today we’re going to be talking with Kyle Taylor, founder of The Penny Hoarder about what he’s learned about both how millennials think about money, work, and life building his digital media empire, mission-based work, and alternative career paths. Kyle is the 32-year-old founder and CEO of The Penny Hoarder, a media company based in downtown St. Petersburg, Florida with 12 to 17 million readers a month.

The Penny Hoarder was named the fastest growing private media company by Inc. 500 two years in a row. They have helped millions of people transform their finances and provide editorial and video programming to help people stress less about money. Kyle and I connected after I wrote a story about Robyn Bree, a local young woman who saved almost $100,000 while still in high school, that The Penny Hoarder picked up. Kyle is basically a media wunderkind and I think will offer a pretty different perspective for our audience. Kyle, welcome to our show. I’m honored that you joined us.

Taylor: Thank you so much for having me.

Steve: Yeah. I appreciate you being here. Okay. I want to just jump in and talk a little bit more about your background and The Penny Hoarder first. Before we get started, I just wanted to say congratulations on building a self-funded, profitable, eight-figured digital media company. It’s no easy feat in a world where the barriers to entry are low, and many big media companies would love to have a business like yours. Can you just share a little bit about how you got started and how you ended up here?

Taylor: Sure. Well, thank you for that, first of all. Yeah. Have you ever seen the show “The West Wing?”

Steve: Yep.

Taylor: I watched that show religiously throughout high school, and I wanted to be, more than anything, Josh Lyman.

Steve: Nice.

Taylor: Josh Lyman was the deputy chief of staff, and his job was really to manage relationships with congress. I started volunteering on campaigns in high school. Then, in my first week at college, I was going to the University of South Florida studying political science, I saw an ad in the paper for the AFL-CIO. They were hiring people to go door-to-door to register people to vote. I was so excited. I went the next day for my interview. By the end of the week, I had my clipboard, and they were dropping me off in some strange neighborhood. I fell in love with campaigns. For the next eight years, I worked on campaigns all over the country in my quest to be Josh Lyman.

Steve: Yes.

Taylor: The challenge is that campaigns are short-term jobs. I had a knack for picking really awful candidates that couldn’t win elections. By the end of every campaign, I was out of a job looking for a way to pay rent, looking for ways to pay my bills, and I had developed a little bit of a knack for finding interesting side gigs to get me through those few months. Along the way, I was also racking up a lot of debt. At 25, I had racked up almost $50,000 in credit card and student loan debt and reached what I called “my rock bottom moment,” where I didn’t even have enough money to feed myself.

Taylor: I was so embarrassed by it because I had been struggling with money for years. I had gone to the bank of mom and dad many of times, and I didn’t want anyone to know. I would often turn my phone off because I didn’t want them to see the collectors calling all day long. I started writing about it on an anonymous blog. It was a Blogspot account. Because I didn’t want anyone to know about the debt, I came up with a pseudonym, “The Penny Hoarder.” For the first six months, it was just a private online journal, a way for me to talk to myself about how much debt I had, how I had gotten into that place, and what I was doing to pay it off? Never in my wildest dreams did I think it would be a business. It was really just an accountability buddy.

Steve: That’s amazing. That’s a great story. Do you relate to a lot of the FinCon bloggers? They seem to have a similar story arch of like, “Hey, I had some serious money challenges,” or, “I hit rock bottom.” Then, we talked about J. D. Roth a little bit earlier, but people like that, some of them, they figure it out and they get on this journey and they use writing to hold themselves accountable, share their story, share what they’re learning. Some of them … I would say, of all the people I’ve met, you’ve got to be by far the most successful story on that arch.

Taylor: Thank you.

Steve: Do those quotes relate?

Taylor: I absolutely relate to them. In fact, when I started blogging, I didn’t know anything about what even blogging was. I remember about a year in telling my parents that I had started a blog, and I didn’t give them the domain name, but I started a blog. My mom goes, “What’s a blog?” I absolutely relate to them because in those early days when I didn’t know what I was FinCon sites to learn about what they were doing. It was inspirational to me and a big part of why I decided to take it from hobby into business.

Steve: Yeah. I went to my first FinCon last year, and it was pretty amazing to see 2,000 bloggers and hear their stories. It’s a very supportive community. It’s pretty interesting seeing how these folks share their stories, but also what they’re learning, what’s working for them, and encourage each other to do different things. Even like this podcast, I don’t think we would have ever done this unless we were like, “Oh, look at those other people doing podcasts. Let’s give it a whirl and see what happens.” Then lo and behold, sometimes stuff takes off.

Taylor: It really is the most supportive community. I don’t think that exists in other blogging niches, at least not to this extent. If somebody in the personal finance blogosphere ask you for a favor, no one would turn you down because that is just the kind of community we are.

Steve: That’s true. I’ve definitely seen that. Yeah. I think you have a real Horatio Alger story where you hit bottom. You had $50,000 in debt. You’d pursued your passion in terms of your political passions, and then discovered that, “Hey, there’s an opportunity here,” and made it work. Were your parents entrepreneurs, or did you just fall into this?

Taylor: A little bit. My dad worked for a credit card processing company for many years. He worked from home. He’d always had this kind of itch to get away from it all. In his mid-30s, he taught himself tennis, quit his job, and became a tennis instructor.

Steve: Wow.

Taylor: Now, he manages a dozen different facilities in Colorado.

Steve: I think that’s a great story. I think it’s really interesting how families and how you’re raised influence people in big ways. My parents were divorced, same thing, when I was about 12 and I saw my mom raise my brother and I. She did the same thing, working really hard, sometimes coming home crying at night and be totally overwhelmed and exhausted from the stresses of trying to make things go, which I think influenced me. I have a pretty high work ethic. I enjoy working, but also, I saw her building her own small business, but I’ve seen the successes and failures. It’s great to hear your story with your dad saying, “Hey listen, I’m mid-30s,” which many people don’t do. They get to their mid-30s, they’ve got kids. They’re just like, “I’m not going to take this risk.” Actually making it work and achieving his dream, that’s cool. Also, I think obviously from what your mom did, that’s resonating because you started doing some of these side gigs as a young adult. Right?

Taylor: I did. One thing I always admired about my mom was as hard as she was working, she still tried to make it fun. All right. One of my favorite memories is we were trying to save money as a family, and my parents laid out everything, that we knew exactly how much money was coming in, how much money was budgeted in every category. My mom felt it was really important for us to understand the household’s finances. We were trying to cut back on our utility bills, so she made this really colorful chart and hung it up in the kitchen. Then every day, us kids took turns going out to the meters on the side of the house and recording what our energy usage was from the day before. Then, she would challenge us to try to get it even lower the next day. I thought, “Well, that’s such a …” Looking back on it, what a genius way to get kids to turn off the lights and save a little bit of money.

Steve: That’s awesome. Yeah. I think it’s so important. It’s hard when you grow up this way and you see the challenges, I think you internalize that and it becomes a life lesson. You appreciate what it is to not have as much money or how it can make your life better. Right? Enable your life. When you have more money, it’s more difficult. By the way, Kyle is sitting here in our house in Mill Valley, which is a pretty nice house.

Taylor: It’s very nice, you all.

Steve: I’m raising my children and they’re having a very different upbringing than I did, and I try to tell them stories about how I grew up and my grandparents and some of those challenges that we’ve had, but they don’t see it although I do see these issues where they talked about, “Okay. The first generation makes money. The second generation hopefully maintains that old debt, and by third generation, it’s gone.” The data actually bats us up that generational wealth, at least historically, hasn’t lasted.

Steve: Now, with the state, law is changing and stuff like that, maybe it will start lasting longer. I don’t know. Actually, I don’t think that’s especially a good thing. I think it’s an important part of our society that people have to work hard, accomplish things on their own and people shouldn’t necessarily be born until like tons of wealth and be able to escape through life and I think that leads us to having a strong culture as an aside, but I can see why this is difficult. If you are successful. Kyle’s clearly successful. If you ever had a family or whatever, then you’ll have to have deal with these challenges yourself.

Taylor: No. I think that’s true. Coming from a family that had to work really hard to make ends meet, I carry that around every day and it’s always something in the back of your head no matter how successful you get that you could quickly be back in that situation. Often, I find making decisions with that mind.

Steve: Yeah. That’s good. Have you ever hear of Andrew Grove? He’s the former … He was the head of Intel, and he said … He was known for his saying, “Only the paranoid survive.” I think that’s true. Companies that thrive, no matter how big, and Bill Gates has said, “You never ache more than 18 months from complete destruction.” Even when he was at the peak of his powers, and so you see that with companies that do well. They keep cranking and they create this culture, and I think now even Amazon, Jeff Bezos, he embodies this where it’s hard to get hired there. They are known for having a very tough culture and they try to raise the bar all the time. Now, there’s a balance, right?

Steve: You’d have to make it a good place people want to work, but also try to do better and better because the competition knows those up. Anyway on that note, now you’re 110 people and I know culture’s important for you. I’d love to hear how you … It sounds like some of your family experiences were probably informed how you see your team and how you work with your team and built your culture?

Taylor: Yeah. Culture is huge for us, and I think a lot of times in companies, particularly young startups talk about culture, they think about it in terms of what kind of beer is in the fridge, and what kind of games are in the kitchen? For us, culture is about bringing a team together that has a similar set of values and we are all guided by doing mission-based work. At The Penny Hoarder, my mission is to put money in people’s pockets and we look for people who really care about that and who can use that mission to make every day decisions. I’m going to give you a couple of examples that might surprise you. At The Penny Hoarder, we turn down more than half of the advertising that comes our way.

Taylor: In fact, our editorial team gets to vote on what … A part of our editorial team votes every week on which advertisers to bring on because we feel it’s so important to only bring on partners that would fulfill that mission. If you’re going to have that as a company idea, you got to have people who can embody that and practice that every single day. It’s around a set of values too. We look for people who are really kind. I have a “no assholes” rule in the office.

Steve: That’s good. I’ve evidently heard that out there.

Taylor: Yeah. No assholes. That’s very important. We want people who are really bold. I want people to take chances, and the media industry is moving away too quickly to be able to keep doing what you did last year because as you say, you’re only 18 months away from failing, and so you have to keep innovating. We want people who are leaders regardless of the title. I often ask, even our junior associates to know that they’re going to have some decision making power over something and that’s important because we’re publishing multiple times a day, and as a CEO, I have no idea what is going to be on the website today. I have no idea what’s going to be on Facebook today, and so we have to hire people that we trust and that are really comfortable making those decisions and using all of our values to put out content that’s going to be great for our readers.

Steve: Wow. That’s great. It’s great to hear you focus in culture, empowering your team to make great decisions, and it’s reflected on the success you’re having, but I think it’s definitely the right approach to that.

Taylor: Yeah. Every company is only as good as its team. That is absolutely true.

Steve: For sure. We talked … Just before I get off this topic, now you started with yourself, and then it sounded like you’re working at home for a little while, were in a small team, no office. Then, now you’ve got the whole operation. We’re talking about using Slack. We use Slack. We had a 10 to 12 person team and it’s manageable, but when you have 110 people, it starts to get out of control.

Taylor: It never stops buzzing.
Kyle Taylor in studio

Steve: Right. Any big things you’ve seen or learned or challenges you’re seeing now that you’re getting to this size?

Taylor: Yeah. I think often times when people talk about our story, it’s grown really fast over the last few years, and it sounds like things had just been rosy every single day and that is absolutely not true. To just rid you of that notion right now is it’s been a real uphill battle to get to this point and there are a lot of challenges along the way. One of the hardest parts for me … The early group, the first five worked at my kitchen table for a couple of months and then we moved into a small office and got up to the size of about 12, and there was a couple of month period, I remember so well because it just felt like everything was going wrong. We lost one of our bank advertisers, our building was infested with termites. One of our employees hated another employee and it caused a lot of drama in the office.

Taylor: I started realizing that even though we were making a lot of money, I had to worry about things like cash flow and I started worrying about how I was going to make payroll on certain weeks. I had this humongous amount of stress that I had never experienced in my entire life, and it was a real gut check moment for me of why am I doing this? Right around that same time, I had a big fortune 500 company come knocking on the door and they said, “Do you want to sell the company?” It’s something I wasn’t thinking about. At the time, I went home and I went and talked to a boy friend and I said, “Hey listen, I have this opportunity. They’re talking about generational wealth. Oh, by the way, my building is infested with termites.” This is an easy decision, right?

Taylor: He said to me, “No. You just started this three months ago. We moved our entire life to Florida. You’ve put so much time into this, you put money into this. Why would you quit after only three months?” That was a moment for me that I looked back to now all of the time whenever I have challenges at the company that it’s not going to be uphill. It’s not going to be gravy every single day, but you have to remember why you’re doing the work and that gets you through all of those tough moments.

Steve: Yeah. You talked earlier about mission-based work and how you got to this point where maybe it was a little earlier, but you reached seven figures, you’re profitable but you weren’t totally happy. Then, something changed. I’d like to hear how you’re thinking change about how you run the company and …

Taylor: Yeah. The first few years of building website, I’ve made hardly any money at all. Then, the next three years, the site started growing pretty quickly and I was still on my own and living in Maine at the time, had a cute little house, black Labrador retriever. It would snow seven feet during the winter, but we didn’t care because we would just watch Netflix all day long and I have gotten the website down to just an hour or two of work every day to be able to pull in, as you say, some pretty significant income. It was by all accounts, what I’ve been dreaming of.

Steve: Right.

Taylor: It felt like I had reached the top, so to speak, but after a few months, I found myself getting really unhappy and it’s strange to say because I was sitting in a very privileged position, but I wasn’t doing anything that actually cared about. I wasn’t doing anything that fulfilled my purpose, and for me, my purpose, I’ve worked in campaigns for many years as I told you. I’ve always believed my purpose is using … Is to help people get a leg up in life and to use my communication skills and creativity as a way of doing that. That’s what I did on campaigns. I love working in media relations. I love working in field organizing. All of a sudden, now I’m just sitting on the couch all day, I wasn’t doing any of those things.

Steve: Yeah.

Taylor: That’s what inspired me to move back down to Florida and turn this into a real company.

Steve: That also informed you not to sell the company and keep cranking it around?

Taylor: That’s right. When those offers come now, it’s very easy for me to just say, “No, thank you.”

Steve: That’s awesome. That’s great to hear. Yeah. I picked up for part of the reason, somebody has a copy of Viktor Frankl’s, I think Man’s Search for Meaning, and he’s our former philosopher, but he talked about basically for people to be happy, to have to have meaning. It’s all about meaning in life. It’s not about pleasure. It’s about the search and pursuit are doing work against something that’s meaningful to you, and this is something that we think up a lot about as well since with our audience, they’re 50 to 60 years. They’ve finished their main career, but they still have a lot of human capital like capacity to work and they’re really thinking about what’s next? They think about how to be healthy? What am I going to do with my life? How am I going to pay for it? How am I not going to pay for it? It’s like what we help them with today, but where else we want to get them to help them think about and be thoughtful about like … You know what I mean? Doing the next.

Steve: I was talking with one of our users the other day, this guy Curtis who’s a forester. He’s like, “Yeah. I’m 65.” Wrapped up his first career, “I’m in a great position financially, and I’m all set, but now it’s like, ‘Okay. What’s next? What is the next mission?'” I think that for a lot of the users, that’s something that they’re really thinking about. It never ends.

Taylor: I can tell you, it’s something that we hear around the office a lot too. I employ quite a few millennials, and what’s important to them is not just bringing home the paycheck. They want to feel good about how they earn that paycheck every day.

Steve: Right. For sure. I definitely seen that in the press, and we work with some millennials too. I think things like the kind of work you’re doing, schedule control or more control about your life and the people you work with, the kind of work you’re doing, where you work, stuff like that, where you live, those are all important things for millennials and also boomers if they start to look around and think about it a little bit more.

Taylor: Yeah. We hear it from readers too. There’s several sections on The Penny Hoarder’s website around side gigs, around working from home, around dream jobs and I call that entire category sort of workplace freedom, getting away from the 9:00 to 5:00 and it’s by far, some of the most popular topics on the website.

Steve: Yeah. Well, I think this is a great segue into the next part of this podcast because I wanted to see if there were some lessons that we could take from the millennials or what you’re learning with your audience that might apply to our audience. We talked a little bit about life control and so forth. Well first, I’m going to give a little … Since I did some research, I’m going to give some quick stats here. The millennials are aged 22 to 37 right now. There are 92 million of them. Gen X is 34 to 54. There was an overlap there, and there are 65 million of those folks. Then, boomers are 54 to 72 and there are 75 million of those folks. The millennials are the biggest generation right now and they’re entering their prime earning years and the way they think about money, and so forth, there’s a difference. Yeah. Like any big lessons and insights that you’ve taken away from your audience that you think might apply to the boomers as they start to think about what’s next for their lives?

Taylor: I think one of the biggest factors that play into how millennials think about money is that they watch their parents go to their financial crisis, and I think that’s shaped as a millennial. I can tell you that shaped a lot of our opinions. First of all, we saw parents doing jobs and in many cases, that they didn’t like doing and working for a company for many years and then you reached a crisis, and all of a sudden, they’re disposable. Millennials go into work thinking about not how can I be loyal to a company, but how can I be loyal to my purpose in life? How can I be loyal to doing something that I really care about? I think that shapes not only the kinds of jobs that we do, but also how we spend our money. I think there’s all these stats showing that millennials are spending less and less money for clothing, for example and that has become a real struggle for retailers because we care more about things like our avocado toast, and going on trips and experiences with our friends.

Taylor: I think it’s because since we’ve seen our parents in a place without money, we think about spending it in a way that really is fulfilling to us, and a way that is more lasting. Experiences I had on that trip 10 years ago, I still get joy out of that, but the pair of Prada shoes that I bought at 18 and didn’t pay off until I was 26 stopped bringing me joy a long time ago.

Steve: Right. Wow. Yeah. It’s interesting also since I have a Gen Z kids. What I see, the access to information and knowledge and experience is shaping each generation and ramping, I would say characterizes, ramping them up quicker. Things that my parents might have taken a lifetime to learn, maybe I learned by 30s. Things that I learned in my life, millennials are learning in their 20s. I feel like Gen Z is learning the stuff in high school. I can say that my 17-year-old has political opinions that are well informed, and much more sophisticated than I ever had in high school and because he’s got access to so much information. It’s good and bad. Everything bad that you can find in the internet, they can get their hands on, but they can also consume so much information in so many different ways, podcast, videos, reading books, whatever it is, but they also … I think many of them have a healthy skepticism of news, or where they’re getting information from. I think that’s dramatically changing our society and it’s interesting to see how it involves.

Taylor: Yeah. I think it’s broader than just news. There’s a general distrust of these institutions. We’ve seen that as a personal finance site. For example, a lot of our readers have distrust of banks. They hold on to what happened during the financial crisis, and it’s really affected how we write about personal finance. I think the way a lot of news sites and other money publications wrote about money in the past couple of decades was to tell you all the things that you should have done by now, and to tell you all the things that you’re doing wrong. What we found is that millennials in particular are very, very put off by that. They don’t want to be told by a big bank that they should have $200,000 in savings right now. In fact, they might have a few choice words if someone told them that.

Taylor: Instead, we approach content by telling people real stories, real people who have gone through struggles and figured out how to get all of that with a way of hopefully inspiring and motivating somebody to take a similar action.

Steve: Right. I think making the stuff much more relatable is important for every generation and I was telling Kyle earlier that on a recent podcast, we had a xDeaa, Jen and this is the first time we’ve had a normal person telling their story about what they went through with retirement or getting a lot of comments like, “Oh, I totally relate to this guy and lucky he learned about what was available to him,” and benefits from the federal government and he figured out how to work it appropriately and make the decisions as a normal person that have led to him being pretty much financially independent and he’s had … As a public employee, kind of like traditional career and also his thinking about what is going to be the next? A lot of people are like, “Oh, yeah. Totally. I totally get that,” and that applies to me. I think I’ve been telling our contact, they’re like, “We need to do more personal stories and more interviews and stuff like that.” Hopefully, we’ll start to emulate some of what you’re doing.

Taylor: People often ask me about starting a website, whether it’s still a good idea to start a blog, and I heard the staff the other day that there are now over 500 billion blogs on the internet worldwide.

Steve: Wow.

Taylor: 500 billion.

Steve: Wow.

Taylor: When you’ve got 500 billion competitors, there’s not a lot left to write about and the only one thing that I think is still unique and that still needs to be written about is your own personal story. That’s the one thing no one can copy. Some people talk to me about starting a website, and I said, “That’s the thing you got to focus on. What makes you unique? What’s interesting about your life?” Because it’s something people can relate to and it’s something that’s different.

Steve: Yeah. Okay.

Taylor: He’s live fact checking.

Steve: I’m live fact checking. 500 billion. I think it’s 500 billion because there’s only 7.6.

Taylor: Oh, 500 million? I’m so sorry. I’m like, “How is that possible? There’s not enough people.”

Steve: If we all wrote 40 blogs, but yeah, 500 million. I totally believe that. Someone was actually telling us that there are on iTunes, 500,000 podcasts now.

Taylor: Wow.

Steve: I’m sure they’re not all active, but it’s a similar thing where there are so many out there. How do you stand out? Yeah. We’re all becoming content creators, or not all, but some are becoming content creators.

Taylor: I think you have to either tell a story that no one’s heard before. You have to collate information in a way that people haven’t before, or you have to say it in a tone that someone hasn’t said before. Those are the three pass to creating unique content in my opinion.

Steve: Yeah. I think that’s right. We’ve had an attention-based media environment now for several years, but it’s becoming more and more important and the scarce resources, people’s talking about, “How do you get them to pay attention? How do you get them to engage? How do you build community?” It’s not simple and there is an endless amount of competition out there. A little bit more about the millennials. I was looking at some data. They’re pretty, like you’re saying, conservative because they’ve been informed by living through the financial crisis. Yeah. They value experiences over things, which I think is hopefully good for the world and good for the environment and everything else. What do you see in terms of like how they think about investing and savings and priorities? Any things that you’re seeing there?

Taylor: Well, a little distressful of investing. Obviously, again the crisis has a big impact here. I think that’s something that may take a little bit more time before millennials are really ready to start investing serious amounts of money. I will tell you one other trend that we’re seeing. This gets back to the workplace freedom idea is that millennials are okay working multiple jobs. Many of them are making a living and certainly I can relate to this. This is life for me for many years by putting together a lot of different side gigs and turning that into an income, and I think that has some interesting long term impacts. One that is important to me having campaign on the Affordable Care Act is how it affects millennials and their health insurance needs? Many of them are coming off of their parents’ insurance now at 26, and if they’re not working a full-time job with an employer that provides for it, I think that’s a real challenge that a lot of millennials are going to face is how to support themselves and pay for their own health insurance if they’re not working in a full-time job?

Steve: Right. Yeah. Well, healthcare is also a huge issue for folks facing retirement because they have to get to Medicare and if many people retire before 65 when you’re eligible for Medicare, and so they have to figure out how to fund that, it’s I think now, the number one concern for people going into retirement is actually health is not just income, it’s like healthcare cost and it’s a huge challenge for our country. Medicare itself got the biggest under funded exposure bigger than social security, and we’re talking about social security now, but people are going to start talking about Medicare in a big way and it’s like within the next 10 years or something, we’re going to be running a deficit. Then, how is it going to be paid for and one of the stats I’ve given out before in this podcast is I think the average person pays $140,000 into Medicare in terms of taxes over their working life, but they claim $410,000 of debits, it’s just not going to work.

Taylor: Wow.

Steve: That math doesn’t work.

Taylor: Yeah. Especially when you have a smaller workforce compared to the size of the population that is about to retire.

Steve: Yeah. I think the reality is people will end up working longer and how they do work will change, and this whole gig economy that we’ve seen emerge with the millennials, now you’re hearing stories that actually Uber, they’re recruiting 50 plus rails. Lyft is recruiting 50 plus rails because drive part-time, made a couple of thousand bucks a month, that actually totally makes a huge difference. I heard the CEO of Starbucks, Howard Schultz on a podcast, Masters of Scale and it was actually really great to listen to him, and he shared like, “Hey, listen.” They’re also super mission-driven and they also try to really take care of their employees and they were like, “Hey, we want to provide healthcare for everybody if you work 20 hours or something as a …” They call them partners. The delivery, now people are like, “Oh, maybe I’ll go work at Starbucks to get my healthcare.” That’s interesting to see people look at it that way.

Taylor: In this industry, it sounds like he might run for president, too.

Steve: I think so. From what I heard, I like a lot of what he was saying. I thought that was pretty interesting.

Taylor: I can go, “Howard, you got one vote already.”

Steve: Come on our podcast. Yeah. Healthcare, how to pay for it, gig work. I saw that you did this kind of like movie preview auditor, beer auditor like you’re making money doing these side gigs when you’re really young. Do you think there … I can see when you’re older, you’re trying to find these jobs that are interesting, maybe we could use some additional benefits like healthcare. Anything that you’ve seen out there that you think might apply at someone who’s 50 plus?

Taylor: I think there are a lot of things. In fact, my own mom, I had dinner with her a few weeks ago and she’s getting too close to retirement age, and she’s like, “I really want to do something else.” Just 20 hours a week. There’s like one person in the world I thought to ask. I said, “No pressure.” She signed up to become an Amazon fulfillment driver and both my sister see this as well and they’re doing quite well. I think my sisters are earning around $25 an hour delivering Amazon packages. My mom also signed up to be an Instacart delivery, so she hopefully soon will be going to the grocery store to make an extra side income. I think there are a lot of these, and they are only going to increase over the next few years. We’re just at the very beginning of the gig economy.

Steve: I think that’s right. Another thing that I also listened, I think it was TaskRabbit where I heard from the CEO of that firm of another podcast, and she was talking about people are … Well one, they’re enabling … Wants people to make money, but two, there’s a community where people in this community are helping each other to scale up to learn how to do things better. Yeah. They are people that are great at assembling IKEA furniture, but now there’s people that are learning how to do a more advanced task essentially, and they’re teaching each other so that they can learn more money like, “Okay. Now, we’ll learn this electrical work.” Then, it’s pretty interesting to see how that emerged, and then people also, as they get more skilled, they have more choice about what they want to take on.

Steve: You can be sitting there and getting more control. You can see work that’s coming in, choose what to do or when you want to do it, so there’s a lot of benefits. Hopefully, that will be balanced out by the ability to get the basics of healthcare and being confident that you have enough money, so that you can have the lifestyle that you want to have. I don’t know if you’ve seen … Do you see a lot of people doing those kinds of like … Do you get feedback about any of those platforms of “Some do better than others?”

Taylor: Yeah. I think a lot of this also depends on where you live, so the folks that live in big Metropolitan cities have a few more options at their disposal. Things like Uber and Instacart might not be enough to keep you busy all day long if you live in a smaller town or a more rural area. That being said, as I said a moment ago, I think they’re just the beginning of them and there’s a lot of different ways that readers on the site make extra money.

Taylor: There’s apps now that will just list for you gigs all over the area, things like Field Agent and Gigwalk will tell you, you can make $9 to go to your local Walmart and take a picture of this display or you can earn $10 by going to the movie theater and writing down all of the previews, which is one of my jobs for a very long time. You do have to be creative and that’s one of the things that we try to provide on The Penny Hoarder is the resources for people to find, those kind of site gigs that are legitimate and have been checked out, but the opportunities, I think can exist at wherever you are if you’re willing to look around.

Steve: That’s awesome. That’s cool. Quick last question on this. Have you ever read up on Universal Basic Income?

Taylor: I have.

Steve: Any thoughts about that?

Taylor: I think it’s an idea worthy of consideration. There’s been a lot of talk in recent years about how automation and technology might lead us to a place where there are less jobs available. I think time will tell when it comes to that, but the one thing that does make me nervous is that I do think there will be a lot of job rotation, I think over three million truck drivers in this country and what does work look like for them when automated vehicles are driving all our goods and services? I think we’re going to have to think long and hard about things like workplace, assistant job training and helping people find a new career in life and I’m supportive of some of the pilot programs that are happening around the country and around the world rather for Universal Basic Income because I think it’s a worthy idea.

Steve: Yeah. Yeah, I know it’s being tested in some different countries, and I think it was … Even places like Alaska sort of have it where they have baseline income if you live in Alaska.

Taylor: That’s right. Well, there’s a lot of studies showing too that it can promote entrepreneurship when people are less tied to having to work all day long at a main job, they can spend more of that time going out and building a business, building a side gig that might become a business someday.

Steve: Yeah. One of the things that I wanted to do is just build a trench art about the number of hours of work that people are doing on average across history because it used to be that we worked, that we dropped and now we got this 40-hour work week that’s actually a relative recent construct, so is retirement. Retirement itself is a relatively recent construct and now we’re looking forward and automating more stuff — how quickly does this unfold and also how do we adapt by rolling out reeducation programs, ideas like university-based income. We’ll see if that happens or not, but definitely there will be a lot of changes coming, for sure.

Taylor: Well, I’m very interested to see this chart. If you do, in fact, filled it out, I think it will be interesting to compare it around the world too, because the number of hours we work here in the United States is quite a lot more than some of European countries, but they’ve managed to still build a lot of wealth and a lot of success. I’d be curious to see what your research shows there.

Steve: Okay. Yeah. We’ll see if I actually do that. Quick thing, back to your company and just media companies, one of the things a lot of people will get into is like, “Yeah. Can I create my own business?” Blogging is something a lot of people explore. Who do you see as a competition? We see out here NerdWallet, SmartAsset. Those guys are raising … There’s a poll that NerdWallet’s raised $105 million. SmartAsset just raised 28 million bucks. That’s a lot.

Taylor: Can I borrow a cup of sugar?

Steve: Who do see you as your competition and how do you see your company evolving?

Taylor: The competition part of that is always such a tough question to answer. Certainly, there are times and we compete with folks like NerdWallet on a specific keyword, but I think we are building very different businesses. They have built a fantastic business, for example, to help you figure out the right credit card. That’s not something we really spend a lot of time talking about. For us, what we think the long term business looks like is we want to be partner in helping people figure out personal finance decisions from start to finish, and we think that our digital presence is really just fun way to do that, so we’ll continue to go to the website, the amount of content that’s on there, the amount of services we provide for folks, but we’re looking elsewhere, other ways that we can interact with people on their daily lives to get them thinking about how to save money, so for example, this week, we just announced that we’re moving to print. We made a deal with the Tampa Bay Times to run a personal advice, finance advice column called Dear Penny in their weekly Sunday paper.

Taylor: It would help to give us an opportunity to not only reach a new set of readers, but give people a different way to experience personal finance advice.

Steve: That’s pretty cool. You’re going totally against the tide in terms of going to print, but I totally get it. There’s a whole other group of readers out there that you can probably engage in a different way.

Taylor: Back to the computation question, I often say that we’re not just competing against personal finance websites, but we’re competing against all news, all advice. If you’re looking on Facebook, you’re going to have options from Buzzfeed to Vox to Refinery29 to The Penny Hoarder. Those will all become our competition and same with search or any other social platform. We have to be able to hook people in a way that makes them prioritize managing their money over figuring out what Harry Potter house they are in and their latest quiz, because that is our competition as well.

Steve: Just to wrap up here. Next up for you guys, it sounds like you’re going to hire another 100 people, grow in St. Pete, you’re getting into print. Any other big initiatives that you want to share?

Taylor: Well, I think you will hear some other announcements from us soon. I’ll be a little mysterious and just say I’ve been spending a lot of time down the Hollywood for the last few months, and we would love to take our style of storytelling to other platforms. We’ll see where that takes us to the next few months.

Steve: Nice. Well, I appreciate the thinking super broadly about this. I think that’s really cool that you’re able to think about things that way and test ideas like that. That’s amazing.

Taylor: We really just think we’re just getting started, and people ask me all the time what am I going to do next? I say, “What do you mean what am I going to do next?” This is too much fun. I want to do this for the rest of my life.

Steve: Totally. Well, having that … That’s so core having that thing that you’re doing that you’re super psyched to do every day, people that do that, they do a fantastic work. That’s clear that they’re doing that, and people that aren’t doing that don’t always know it, but if they start meeting more people that are doing it, then they’re like, “Okay. Maybe this is what’s possible,” and basically I and I’m sure you would encourage everyone to try to find that passion and meaningful thing that they’re really super confident like the thing that they should be doing, it’s like they’re calling. That can change your life in a huge way.

Taylor: I couldn’t agree more.

Steve: Okay. Any questions for me as we wrap this up?

Taylor: I want to hear what’s next from you? What’s coming up on your retirement?

Steve: Good question. Well, we’re doing something with just roll out a paid version of our product. We’ve been doing our work pretty much for free. We do have a little bit of media model, but advertising referrals, but we are now going to start asking our customers to pay us, which we think is important and a better way to do business. We rolled out a paid subscription model for more advanced version of our tool. We are going to be testing advice directly, so often kind of an hourly or subscription based advice model where people … Where we can do a collaborative planning and I think that’s key. Also potentially, disruptive for delivering financial advice and guidance out there, not only done through a subsidy area that’s a registered investment advisory and a fiduciary. So much we touched on this earlier, but so much of financial services is often directly paid and not transparent.

Our average customers is 50 to 60 years old. They have about a million dollars saved if they’re paying traditional wealth management fees. They’re not doing it themselves or many of them are using wealth managers and they’re paying 1%. I think the average fee is 1.2%, so they’re paying 10 to 1,300 bucks per year, which can be great if they’re helping you make really good decisions, but we feel like this can be accessible to so many more people with a more transparent model. This is a big test for us, and then if it works, hopefully it will be scaling our business, but we shall see.

Taylor: It’s very exciting. Very exciting.

Steve: Yeah. Anyway Kyle, I really appreciate you taking the time to come here, sit here in the studio with us. This is great.

Taylor: It’s been fantastic.

Steve: Thanks, Kyle for being on our show. Thanks Davorin Robison for being our sound engineer. Anyone listening, thanks for listening. Hopefully, you found this useful. Our goal at NewRetirement is to help anyone plan and manage their retirements. They can make the most of their money and time and we have our powerful retirement planning tool, educational content that you can access at newretirement.com, and we’ve been recognized as best in the web by groups like The American Association of Individual Investors.

NewRetirement Planner

Do it yourself retirement planning: easy, comprehensive, reliable

NewRetirement Planner

Take financial wellness into your own hands and do it yourself retirement planning: easy, comprehensive, reliable.

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