Episode 022

St Pete X features business and civic leaders in St. Petersburg Florida who share their insight, expertise and love of our special city. An initiative of the St. Petersburg Group, St Pete X strives to connect and elevate the city by sharing the voices of its citizens, and to bring awareness to the opportunities offered by the great St. Petersburg renaissance.


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06/02/2017 | Episode 022 | 46:10

Kyle Taylor - Taylor Media - The Penny Hoarder

Kyle Taylor talks the changing face of our economy, what that means for business and education, and how The Penny Hoarder is revolutionizing digital publishing as we know it.

On this episode of SPx, host Joe Hamilton sits down with Kyle Taylor, millennial founder and CEO of the multimillion dollar company, Taylor Media. Publisher of The Penny Hoarder, Taylor Media's mission is to put more money in people's pockets. Enjoy this conversation on St. Pete's entrepreneurial environment, Kyle's take on the changing faces of education and business for an evolving economy, and The Penny Hoarder's revolutionary monetizing strategy. Hear about why Kyle chose his hometown to start his business, and how he's recruited talent, local and national to St. Pete. This interview was originally shot on video. Head to the show notes on StPeteX.com to watch instead of listen.

Key Insights

  • Kyle Taylor is the founder of The Penny Hoarder & Taylor Media Group. What started as a hobby has developed into a multimillion dollar media company, growing rapidly in St. Petersburg.
  • The Penny Hoarder started out of Kyle's personal experiences. With $50,000 of student loans and credit card debt plaguing him, Kyle started blogging about his personal finance hacks and adventures.
  • Nearly three years ago, The Penny Hoarder opened its doors and began hiring - writers, graphic designers, and creatives of all stripes. They've grown from 1 to 88 over the last few years, and recently announced they hope to add 165 new employees by 2020.
  • The St. Pete Greenhouse was especially helpful in The Penny Hoarder's business development - the effort, a partnership by the City and Chamber, helped with the many pieces of starting and running a business day-to-day that can be mysterious for a new start-up.
  • Taylor finds St. Pete's open and helpful nature to be a unique feature of its community - as he says, one conversation often turned into 3 or 4, and he rarely hit a dead-end.
  • Weekends in St. Pete: Kyle spends his free time as an escape room junkie. In fact, he's tried almost every escape room in Tampa Bay. He and his team also enjoy local breweries and beaches.
  • Like Warren Buffet, Kyle spends much of his precious free time reading, trying to finish one book per week. He prefers non-fiction, and mentioned One to Many as one of his favorites that he re-reads quarterly to check back in with himself and his management practices.
  • Kyle mentioned a familiar misconception - that St. Pete is not tech-friendly. This is not true, he says. It may not be Silicon Valley, but there are tons of start-ups and established tech companies thriving in St. Pete.
  • Despite this misconception, Kyle has had no trouble hiring talent in St. Pete and attracting talent to relocate to St. Pete. Of his 70 employees, 25 moved to St. Pete, over a dozen from New York City.
  • One of the changes that has caught Kyle by surprise in The Penny Hoarder's upward trajectory is the ways he has had to change his management style. "The first five of us started at my kitchen table, because we didn’t have an office. And when you’re working in someone’s home, it’s a very different kind of relationship."
  • At 70 employees, things have changed drastically, "All of the sudden, one thing I found is that my words carry more weight. We’d be spit balling an idea, and I might say, ‘Oh, that’s a great idea.’ Now that means green light, let’s invest money, do that."
  • A larger mission: "We want to be a media company that has a larger mission. Our mission is to put more money in people’s pockets, and I think that’s important, because personal finance for a lot of people is either stressful or boring."
  • Why it's important: "More than 50% of Americans it’s recorded to have less than $1,000 in their savings account, and that just means one accident, one emergency away from being at zero."
  • "St. Pete special is there are very few cities like this, and I was fortunate enough working on campaigns in a lot of them, including Denver and Austin and Charlotte, and all this sort of up and coming cities, and none of them are quite like St. Pete. And that’s because there’s a certain level of charm and community that in those larger metropolitan areas I think you lose."
  • On St. Pete's political climate: "I do think we are a purple city, we have a lot of the quirkiness of a city like Austin, but we have a city that’s also extremely invested in making sure businesses succeed here. And I think that that kind of environment allows for both sides to come together and find things they like about it."
  • On inclusivity: "I think we need to do more, we need to reach out to those communities and make sure that voices from across St. Pete are in the room when those big decisions are being made."
  • On what tomorrow's businesses will look like: "I hope the businesses of tomorrow are still in person, and that technology doesn’t push us away from that really personal feeling that you need to have a strong culture."
  • Education of tomorrow for our changing economy: "People often say, ‘Encourage trade schools or technical schools.’ And that’s true. But even things like internships, and we were talking about Youtubing classes, and self-learning, self-teaching, those things are equally as important, and I think that has to be a bigger part of our education in the future."
  • Monetization of The Penny Hoarder: "We have to be able to provide advertisers some clarity on ROI. We call our model the performance model, we don’t make advertisers pay us unless they’re successful with their campaigns. It’s a lot more risk, we take a lot more chance up front, and sometimes it doesn’t work. But when it does work, not only is it better for the user, because they’re not having a bunch of annoying ads in their face. But thankfully the rates are much better too, and more sustainable."
  • Example: Lyft - "We’re able to act almost like an agency, to create content that helps sign up new drivers. And we don’t get paid until those new drivers are signed up. So every time a driver signs up and gets their first paycheck, we get a check too. And we like it, because everyone benefits from it. Lyft is getting new drivers, our readers are making extra money, and we’re making money to continue to grow."
  • How do they choose their partners? "Is this somebody we would wanna tell our friends about? And if the answer is yes, then they earn a place on the site."
  • Kyle's Shout-outs: TECGarage & Ashby Green.

"We want to be a media company that has a larger mission. Our mission is to put more money in people’s pockets, and I think that’s important, because personal finance for a lot of people is either stressful or boring."

Taylor Media is making major waves in St. Pete. After visiting competing sites in New York and Washington D.C., founder Kyle Taylor announced that St. Pete won the expansion of the already bustling start-up in mid-November 2017. The expansion is promising 165 new jobs to fill The Penny Hoarder’s brand new local headquarters by 2020. The new jobs would include a number of creative, tech, and analytics-driven positions such as video editors, writers, data journalists, media analysts, and developers.

The Penny Hoarder was named the fastest-growing private media company in the nation by Inc. 5000 in both 2016 & 2017. It was also ranked No. 25 on the list of the fast-growing private companies in the U.S. With its growth comes opportunity for the city and the state of Florida. We have heard time and again from numerous factions in the St. Petersburg business community, that higher paying jobs are necessary to attract young workers to St. Petersburg.

To incentivize this job growth, the state has created the Qualified Target Industries program. Under this program, $4,000 state and local tax refunds are offered per job, as well as $2,000 per job for high-impact performance incentive bonus. All told, if Taylor Media delivers on its promises, it’s looking at nearly a million ($990,000) dollars in tax incentives to grow in St. Petersburg. They won’t be the only beneficiaries of this program. The city of St. Pete, the state of Florida, and many local young workers serve to benefit from this influx of jobs whose mean annual wage would be around $66,098 – 1.5 times the current median average income.

"One of the things I was struck by was how incredibly helpful and open folks in St. Petersburg are with their network. Every meeting seemed to lead to three or four more. And that has been so powerful for me, because it’s allowed me to gain a little bit of confidence as an entrepreneur."

Table of Contents

(0:00 – 0:36) Introduction

(0:36 – 1:50) The Penny Hoarder

(1:50 – 3:42) St. Petersburg Supporting Entrepreneurs

(3:42 – 5:45) Spending Free Time in St. Pete

(5:45 – 8:34) The Business Community in St. Pete

(8:34 – 14:51) The Penny Hoarder Trajectory

(14:51 – 16:03) Reading A Book Each Week

(16:03 – 19:03) The Role of College and University

(19:03 – 20:33) Why Moving a Company to St. Pete?

(20:33 – 21:43) Parking Debate

(21:43 – 24:12) St. Pete, a Purple City

(24:12 – 27:22) The Corporation of Tomorrow

(27:22 – 29:19) Education

(29:19 – 31:20) The Penny Hoarder as an Education Resource

(31:20 – 35:56) User Experience

(35:56 – 37:55) Advertising Model

(37:55 – 41:59) Employees Success

(41:59 – 42:51) Media Vision

(42:51 – 45:32) Shout-outs

(45:32 – 46:10) Conclusion

Full Transcript:

Joe: Well, thanks for joining us, Kyle.

Kyle: Absolutely, thanks for having me.

Joe: Appreciate it. So, why is The Penny Hoarder in St. Pete? Why is it not in Austin, or Seattle, or…?

Kyle: Yeah. Well, it’s here because St. Pete’s my home. And I started The Penny Hoarder first as a hobby. I was broke, I dropped out of college and out of a job, and I started writing about what I was doing to pay off my $50,000 in student loan and credit card debt. And so, it didn’t start as a business, but it’s turned out to be a really great place to have a business. We opened our doors two years ago, and I say that’s the time we marked going from hobby to business. And what I love about St. Pete is it’s such a creative city, and since we’re a media company, we have to hire a lot of writers, a lot of graphic designers, editors… And I’ve just been so overwhelmed with the amount of talent that’s in the city.

Joe: That’s great. So, that’s one of the misnomers about St. Pete, that it’s a much older city, and that kind of talent isn’t here. So, you’re saying you have been able to find young, vibrant, creative talent here.

Kyle: It is. I think that might be a conception from what St. Pete may have been ten, 20 years ago. But since the time I’ve lived here, even— I’ve been here three years full time, it’s even transformed since then. So, there’s plenty of talented folks in this city.

Joe: And growing your business, moving from just blogging to actually having a high revenue, really successful business, that’s the big growth that you had to undertake. And how has St. Pete supported you as you’ve undertaken that sky-rocketing?

Kyle: I had never started a business before, so there’s all these things that I faced early on that I had no idea what to do. I needed to find a space, how do you hire your first employee, do you need a lawyer, and if so, who should that be? And so, at first, I started—well, I just frankly did a lot Googling. And it wasn’t much longer that I found the Greenhouse and I started getting introduced people like Sean Kennedy, who introduced me to other entrepreneurs, other folks in town. And one of the things I was struck by was how incredibly helpful and open folks in St. Petersburg are with their network. Every meeting seemed to lead to three or four more. And that has been so powerful for me, because it’s allowed me to gain a little bit of confidence as an entrepreneur. I’m really good at focusing on my product and my customers, but the actual day-to-day of running a business, I needed to learn. And I feel like the leadership here in St. Pete has been really helpful in that sense.

Joe: So, you wouldn’t say there is a spirit of competition here, more of a spirit of cooperation?

Kyle: Absolutely. Plenty of us had competing businesses, but many of us are still friends outside of work, and still share clients and contacts. And I actually have several entrepreneur friends in town, and when we… we share junk candidates too. When someone is not a good fit for us because we don’t need them right there, we share with each other. And I don’t still know that that happens in other cities, it’s pretty wonderful.

Joe: So, what are some of the things you’d like to do in St. Pete’s? What are some of your favorites, on the weekends or at night, or what really…?

Kyle: Besides working at the office?

Joe: Besides working, yes. So, it’s having a huge fast-growing start-up. So, in the 15 minutes you have a week to do something for yourself, what do you spend these 15 minutes on?

Kyle: Okay. Can I nerd out for a little bit?

Joe: Yes, please.

Kyle: I’m an escape room junkie. So, that is my way of unwinding. I’ve been through almost every escape room in town, even in Tampa. So, we’ll start with a scotch, at Cask & Ale and then head to an escape room is my idea of a good night.

Joe: So, you’re saying, as far as you’re concerned, people may say that we’re growing around the craft brew scene, but we could potentially also be growing on the escape room scene?

Kyle: Absolutely.

Joe: It’s pretty good. I know there’s one just up the road here, right near Vertical Ventures.

Kyle: Sure. So, I think there’s three locations within downtown St. Pete area, and then there’s one down on St. Pete beach, there’s a couple in Pinellas Park. So, there’s plenty of locations. And I think millennials in particular have a different way of being entertained. Because we’re the gadget generation, we’re not just comfortable talking to somebody, or just sharing a beer, we have to be doing something at the same time. And I put myself in that camp, I will identify as a millennial. So, the beauty of an escape room, is you’re doing something and having fun at the same time.

Joe: So, St. Pete is a good city to go sit across from someone at a brewery and text them.

Kyle: Yeah, exactly.

Joe: Whatever it is you come to…

Kyle: Exactly.

Joe: That’s cool. In the going out scene, what’s… I’m well past my night-life prime, what’s the vibe you like going out?

Kyle: You and me both. If I’m not in bed by nine o’clock, something is wrong.

Joe: Yeah, something is broken.

Kyle: So, I’m not sure I can speak to the late-night scene, but I do love going to the breweries around town, 3 Daughters… is somewhere we hang out quite often.

Joe: Can you riff a little more on the business community in town? You said, and it sounds like you’ve got, even amongst your competitors, amongst complimentary businesses, or just business people in general, you’ve enjoyed being in that network?

Kyle: So, I have, yes, We’re a media company, but we need a lot of tech-like resources, need developers and such. And I think there’s often a misconception, and I’ve been guilty of saying this myself, that there’s no technology in St. Pete. And I’ve really come to learn in the last few months that that’s not true. There’s just tons of start-ups in the area, many of them in the technology field, and there’s huge companies nearby that employ hundreds of developers, analysts and all that kind of thing, everything from HSN, to Nielson, to Publix. So, it’s really opened my eyes, that I have to think… I think I had a conception that a tech company meant Facebook or Google. And no, we don’t have that, but we do have plenty of other resources. So, that’s been eye-opening for me. On the recruiting front, I mentioned that creative folks are easy to come by. We’ve also been really successful in relocating people. So, we relocated out of our 70 folks, 25 of them we relocated, and more than a dozen of them came to us from New York City. So, we’ve been successful transporting really big city folks to our small town. And I think it’s because—and people always say this, it’s that St. Pete has everything that a big city has, all the amenities of it, but still has that small-town charm and culture. And so, when we bring folks down, there’s been always a little bit of uncertainty, like, ‘Florida? Didn’t see that in my future.’ But as soon as they see the city and they see how quirky it is, and they see the talent in the other companies here, we’ve been successful nearly every single time in convincing folks to move down.

Joe: And so, once those folks have moved down, has the initial first impression come to be true for them, where they thought it was gonna be this, and then their feedback has been that?

Kyle: I’m happy to say that none of them have left. [laughing] None of them went home…

Joe: …concerns.

Kyle: So, I think that we’re doing something right there. A lot of our folks live in the downtown area, so it’s nice for them, they can just walk to work or ride their bike. Like a lot of companies, we struggle with parking near our office, so we’ve really tried to encourage people to live as close to the office as possible.

Joe: Walk and ride bike. Coastal Bike Share seems to be doing well.

Kyle: Yeah, it is.

Joe: So, people are out and about a lot.

Kyle: Yeah, luckily we have one right outside of our office, so you can just drop it off there.

Joe: Cool.

Kyle: Yeah.

Joe: Tell me a little more about the trajectory of The Penny Hoarder, let’s get inside the business versus talking about how it sits in St. Pete. You guys are hockey sticking right now, right?

Kyle: Trying.

Joe: You’re going up. And how has it been to come in again and just…? I know, when I started my own business, the learning curve was steep, and I didn’t have near the rush of opportunity that you have. How are you handling that, and what’s it like on the inside of that rocketship?

Kyle: Fine, and some gray hair just started to suddenly… Oh, no. It’s been an… I’m incredibly lucky. I think the one thing I did well was to hire people that were way smarter than me, that could teach me along the way. But it’s been challenging too. One of the things that I wasn’t prepared for was how I would have to change as a boss as the company got larger. So, when it was small… The first five of us started at my kitchen table, because we didn’t have an office. And when you’re working in someone’s home, it’s a very different kind of relationship. You’re meeting my dog, you’re meeting my partner, you’re in my home. And when it’s five people, everybody is involved in everything, everyone knows everything. And then, when we got to that 25, 30 mark, all of the sudden people were… You’ve got to start giving people the ability to make decisions on their own, because it’s no longer possible for one person to make all the decisions. So, that was a bit of an evolution. And now that it’s 70 employees, and we hope—we think we’ll be at 100 by the end of the year, it’s changing again. All of the sudden, one thing I found is that my words carry more weight. And I used to… we’d be spit balling an idea, and I might say, ‘Oh, that’s a great idea.’ Now that means green light, start investing money, do that. So, I’ve had to really adjust to how the role changes over the years. And it’s been incredibly important that I keep learning too, because like I said, I’ve never done anything like this before. And we were just talking about how Warren Buffet reads all day, that’s been important to me. I’m not quite to 200 books a year, but I try to do one a week. And all this is helping me learn a lot, but I also find it’s my Zen, which is, when you’re working so many hours and managing so many folks, it’s important that you find something to disconnect from that. So, reading has been my way of doing that. And then, the way we think about the business has changed too. When we first started, I said this was a hobby, there was no strategy. We were just trying to get the content out each day. And so, we’ve really had to think strategically about who we wanna be now, and who we wanna be five to ten years from now. Digital media is a tough space, so a lot of publishers are struggling, and our industry is looking for a model that works. So, we’ve had to really pick a couple of spots. And what we’ve decided is that we want to be a media company that has a larger mission. Our mission is to put more money in people’s pockets, and I think that’s important, because personal finance for a lot of people is either stressful or boring. And most of the finance literature out there is not easily digestible, it’s not something that you would want to read. So, having a really strong mission has been important, and that mission has led us to a style of creating content that is fun, and hopefully entertaining sometimes, sometimes silly, but still informative. And we’ve monetized it in a very different way than most publishers. So, rather than monetizing with display ads, we monetize through direct partnerships where we work to… For example, General Mills is a partner. We work to bring folks to their brand in a very native way. Long-term, we wanna be able to take our content to other mediums, so we’re continuing to build out our newsroom now, but we are also investing in Facebook lLve, which has been a lot of fun, we have a studio in the office and our role is to go live every day with the personal finance news that people need to know to make a difference. So, we hope that will be our next 100 employees, our next big growth to make.

Joe: And it’s brilliant. And it’s important work too, because personal finance, big put in, it can have an impact on the country, because that matters to a lot of families. And managing their money well can make the difference between a hugely stressful family environment and a comfortable family environment. And so, I think there’s a national benefit to getting that information in a palatable, digestible way in people’s heads.

Kyle: Yeah. More than 50% of Americans it’s recorded to have less than $1,000 in their savings account, and that just means one accident, one emergency away from being at zero. So, I think it’s critical. And I was lucky, I grew up, personal finance was part of our house, my parents were really open about our budget and we knew exactly how much income was coming in. And my mom used to challenge us, for example us kids would take turns going out to the electric meter each day, and seeing if we can beat the day before to lower the electric bill. So, we were really a budget friendly family. But when I got older and got out of the house, I quickly forgot all of that. [laughing] I started racking up credit card debts, student loans… And I think it’s important that personal finance isn’t just something that—we need to teach it in school, we need to teach it as kids, but it changes throughout our life. The personal finance needs that we have at 20 might be very different than what we have at 40. And so, one of our goals is ongoing personal finance education, so that no matter what age or what your situation is, hopefully there’s something for you on the side that’s helpful.

Joe: You mentioned reading as much as you could. So, what are you reading, what sort of genres are you reading? Are you reading fiction, non-fiction? And any titles you wanna throw out there?

Kyle: Yeah. I like non-fiction and I’m kind of in a biography phase right now. This probably gives you a little insight into what I’ve been thinking about, but I’ve been reading a lot of biographies of people who have run large media companies. So, I just picked up one on Ted Turner, I… Also, I read a lot of management books, which might not sound that exciting, but…

Joe: All of them.

Kyle: …they are helpful.

Joe: All of them. I read them all.

Kyle: One of my favorites is a little 50-pager, and I read it probably lots a quarter, it’s called ‘From one to many’. It’s a 15, 20-minute reading, but it’s a reminder to myself, and it takes you through the stages of different levels of manager. What it’s like when you first start managing, what you should try to accomplish, what you should try to get to. And I use it as a way of checking in with myself, am I moving up in these phases?

Joe: Great. And Peter Thiel has one from zero to one I think, which is also a really good read.

Kyle: I haven’t read Peter Thiel’s, but I think I would enjoy it. I’m kind of fascinated, because I’ve read stories of how they pay folks to drop out of college. Have you heard this?

Joe: Yeah. No.

Kyle: So, he’s a believer that there’s so much talent in young people particularly and that there’s some science that shows that we’re most creative when we’re in our late teens and early twenties. So, they’ve set up some sort of grant to encourage… like people can apply to it to drop out of college and come work for him.

Joe: Well, yeah, there is definitely, I think, a truth to the changing face of the four-year university. It’s people that really aren’t nearly as necessary as they used to be, and because corporations aren’t competing with other corporations to get degrees, it’s corporations who are competing with being an entrepreneur now, because it’s so easy to just do your own thing and make just as good a money, and do it sooner, and not have to… Of course, if you hadn’t done that, you wouldn’t have probably started The Penny Hoarder. It worked out for you, but…

Kyle: It worked out for me. I think college has an important place in society, and for some roles it’s probably absolutely necessary. But, can I tell you a secret?

Joe: Yes.

Kyle: It’s the last thing we look at when someone comes in to interview, it’s what’s on their education profile.

Joe: So what’s the first thing you look at?

Kyle: First thing we look for is will they be a cultural fit, do they share the same values as us? Second thing is do they have a hunger for learning? Definitely don’t want anybody on the staff that is comfortable doing the same thing for the rest of their life. And the third thing is what is their current skillset, what have they already done, what can they contribute? Education is after that.

Joe: So, yeah. I think that speaks to it. And I think it also speaks to the fact that there’s just a lot of education available. It used to be the only place you could get that kind of knowledge was at the University, and now MIT is putting their things online for free at the Conn Institute, you’ve got YouTube, you can literally watch a well-educated person lecture on anything you want at any time on YouTube, so…

Kyle: It’s way more impressive for me to see a resume where over the last ten, 15 years of their career they’ve continued to define ways of continuing their education, whether it would be going to conferences, or reading or taking small classes. That’s way more impressive than seeing that you graduated four years after graduating high school. That’s the track a lot of folks take, so the idea that you’ve invested in yourself and that you’re eager to continue learning would definitely set you apart in an interview.

Joe: So, maybe that’s the idea, the new face of the resume. Here’s a list of all the YouTube videos I’ve watched.

Kyle: Yeah, there you go.

Joe: What do you think of that?

Kyle: Tell me how many video classes you took this year?

Joe: Yeah, that’s cool.

Kyle: I think it’s… something is broken, right? And people are graduating with six figures of education… a student loan debt, and then are spending their next 20 years of their life trying to pay that off. I don’t think that’s sustainable. So, we’ve got to figure out a new model, for sure.

Joe: So, you are you…

Kyle: Yes.

Joe: …but not here. So, you are, for whatever reason, in the Midwest or the Pacific Northwest, or New England, and considering moving your company somewhere else.

Kyle: Yeah.

Joe: And why is St. Pete the right choice to be that destination?

Kyle: Well, I’ll give you the fun answer first. So, last month we did a little team bonding and we did it on the beach, right? How many cities can you say that you could take a bottle of champagne with your staff to go celebrate down at the beach? So, that’s an easy answer right there.

Joe: Yeah.

Kyle: But I’ll also say that one of the things that makes St. Pete special is there are very few cities like this, and I was fortunate enough working on campaigns to live in a lot of them, including Denver and Austin and Charlotte, and all this sort of up and coming cities, and none of them are quite like St. Pete. And that’s because there’s a certain level of charm and community that in those larger metropolitan areas I think you lose. We have all of the great things that those cities have, we have amazing food. I saw we were just rated as the most underrated food cities in America. We have amazing food, we have amazing places to live and we have amazing companies here. There are some of the best companies in the world in the Tampa Bay Area. So, why not be here?

Joe: What do you think of this whole parking debate, Kyle?

Kyle: Well, I think it’s kind of silly, to be honest with you. I’ve lived here for several years, and I haven’t once not been able to park. We have a lot of drivers downtown, I think it’s different than when I used to come up here with my family 15 years ago, where you could easily find a spot on Beach Drive. That’s probably never gonna exist again, there’s just too many of us, and there’s too many of folks visiting us, and that’s a good thing, that’s not a bad thing. But there are a lot of garages. And that means… it may mean you’re walking an extra few blocks, but it’s there. I also think parking is something that will soon be of the past. We are moving to driverless cars, cars that can park themselves, and I think it would be a mistake to use our beautiful viable downtown real estate to build something that we may not need ten, 15 years from now. We will be thinking about what we should be doing with those spaces soon, because we won’t need them at all. So, I think that’s a debate worth ending.

Joe: I like it, that’s very forward thinking, I like that, it’s cool. A term that is used – well it’s a word, It’s a color- it’s purple. And a lot of folks, especially in the Chamber, have put forth that we have a purple community, and that our red and our blue, and our left and our right, mix well here, better than in other cities, and that’s because the love of the city and the community is strong enough here, that the push to be extremist in either one direction is less, and so you get a mixing of the blue and the red… at least in the middle and the further out from the middle than in normal cities. Have you found that, do you feel like we have a purple city?

Kyle: I’ve worked on a lot of local city council, a lot of mayoral races around the country, I’ve never seen a local government like this. Now, we all have our gripes…

Joe: Sure.

Kyle: And that’s a good thing. But the level of agreement about where this city should be going is… that’s pretty unique. Most cities are really struggling with that. So, for us to have any kind of growth plan, or plan for the next 15 years, that’s not something that all cities have been able to agree on. So, I think that’s pretty special. I do think we are a purple city, we have a lot of the quirkiness of a city like, I don’t know, Austin, but we have a city that’s also extremely invested in making sure businesses succeed here. And I think that that kind of environment allows for both sides to come together and find things they like about it.

Joe: And riffing off that… inclusivity. Do you feel like there is an adequate amount of inclusivity and diversity in this city?

Kyle: Well, I think we want it to be an inclusive city. One of the things that I’ve talked about that before is I don’t think diversity can be something you just hope that happens, you have to actively go out and try to make it work. And so, when I go to some of the local business roundtables, or the Chamber, or… everybody talks about diversity and inclusivity, we all feel the same way. But I think we need to do more, we need to reach out to those communities and make sure that voices from across St. Pete are in the room when those big decisions are being made. I don’t see too many people my age there, out there, for example.

Joe: Yes. That’s true, we definitely need more of those. Cool. So, millennials. Since you are a millennial, self-admitted…

Kyle: Yes. And you keep reminding me, yes.

Joe: And you hire a lot of millennials.

Kyle: Yeah.

Joe: Can you peek outside of the millennial bubble that you live in and…

Kyle: Yes, I’ll try.

Joe: …and tell us, especially since you’ve had the unique—it’s often unique when you can go from not having a company to running a larger company, because you experience the growth becoming an executive in a very visceral way, because it’s all new and it’s all learned–it’s almost academic, right? As opposed to…

Kyle: And you sweat, yeah.

Joe: Yeah. [laughing] Throwing to us the big ‘e’ word out, executive. So, how do you feel the corporation of tomorrow differs from the corporation of yesterday?

Kyle: Wow, that’s a big question. Well, I’ll tell you, I’ll start with what I don’t believe. There’s been this big movement that a corporation of tomorrow is all about telecommuting and that we’ll all just work from home on our computers. And I don’t think that’s true, and I actually hope it’s not true. We’ve really made it part of our culture that people need to come to the office, and we’ll allow folks to work from home one day a week, and we’ll do that through remote employees. But being in person, being able to collaborate with somebody around a white board, or being able to hear a little micro conversation next-door being involved in something, those are the things you lose from telecommuting. So, I hope the businesses of tomorrow are still in person, and that technology doesn’t push us away from that really personal feeling that you need to have a strong culture.

Joe: And probably you might say the strongest companies will recognize that the strongest bonds happen when people are in each other’s presence.

Kyle: Yeah. I can spend the next 20 years of my life trying to come up with the best strategy possible for The Penny Hoarder, but it really comes down to the people we’re hiring and the culture we’re creating. If we’re creating a culture where they are able to not only contribute, but to move on ideas without my say so, and they enjoy coming to work every day, is gonna be way more successful than if I can put together some brilliant plan now.

Joe: And what about the folks that are working for more than one company at the same time? Are they sliced up in there?

Kyle: That I do think is a growing part of our corporate culture. Millennials in particular, as you know, are putting together many jobs at once, it’s something I know a lot about. When I first started The Penny Hoarder, I did all these side gigs on the nights and weekends. And that became the fodder for what I was gonna write about during the day. So, I probably had a dozen side gigs at any given time. And I think there will be more of that. St. Pete, we’ve just introduced Uber Eats, and we have now delivery from Instacart. And so, I think that sort of gig economy is in its infancy, and it’s only gonna continue to grow.

Joe: So, accordingly, since you’d have a firm grasp of that and that’s a great answer, how does that trickle back into our education? And how do you see the traditional educations that we had changing, or how do we need to change to better serve this new paradigm?

Kyle: So, when I was a Junior in high school, the only option, at least I felt that way, was to go to college. That was expected from my teachers, from my parents, from my friends. We were going to college. And I think we need to rethink that a little bit, because it might not be the right path for everyone. And to your point about the gig economy, it’s not necessarily the right form to learn for the jobs of tomorrow. Maybe for some, but I do think we need to be creative and encourage people to take different paths to get there. People often say, ‘Encourage trade schools or technical schools.’ And that’s true. But even things like internships, and we were talking about Youtubing classes, and self-learning, self-teaching, those things are equally as important, and I think that will be a bigger part, or it has to be a bigger part of our education in the future.

Joe: From a value standpoint, you can pack in. I know that just in the learning that I do now, I feel like I learned as much in six months as I might’ve done in two years with stretched-out classes and projects and things like that. But it’s really just a matter of demonstrating that you have that knowledge, because…

Kyle: Well, you wanna learn too, right? I think sometimes when you’re 18, 19, getting through…

Joe: As much as you can tolerate.

Kyle: …today’s classes, it’s just a way to get to the fun part.

Joe: Yeah. I would identify with that too. Yeah. So, with the gig economy, obviously one of the big benefits of coming to a full-time are the benefits, the insurances, the retirements. And luckily, they have The Penny Hoarder as a resource to take care of the retirement part of that, but not so much maybe the insurance part of that. How does the having those multiple workplaces affect the daily life and the family set to do that?

Kyle: It’s actually a huge problem, because traditionally employers have been the way that people get their health insurance, their 401k, even things like paid time off. How do you get paid time off through driving for Uber? So, it’s something we have to start thinking about, and I think it’s a place where actually government needs to be involved. We need more vehicles for folks to be able to save, and we need to continue visiting the health insurance discussion, because a young person paying four or five hundred dollars for health insurance is gonna be very difficult in a gig economy landscape.

Joe: Seth Godin has an alternate MBA, and the mantra is ‘Teaching new things you can’t figure out with Google’ And so, it’s thinking. And as far as you producing content, does that resonate with you at all? Being able to put things out there in such a way that it teaches people how to think and what is there, outside of Google or Bool lanes?

Kyle: Yeah, absolutely. So, search traffic is part of our business, but a lot of what we write about is in story format. So, we often say we’re putting the personal in personal finance. And I think that’s important, because we’re not just giving you a list of tips, or ‘Read this to learn about what a 401k is’. We try to find somebody who has successfully done it and let them tell their story. And not only is it easier to digest and hopefully more entertaining, but at the end of that, there’s a little homework assignment that you can take away and put it into your own life. So, that’s really been our format for success when it comes to content.

Joe: And have we seen the death of—and my fingers are crossed that the answer to this is ‘yes’, the list, the seven ways, this and that and the other thing, or the twelve ways to results…

Kyle: You’re gonna kick me out. [laughing]

Joe: Is that still hot?

Kyle: It’s still a thing.

Joe: It’s still a thing.

Kyle: Still a thing.

Joe: It’s still… the list… And then the whole…

Kyle: Or the quizzes.

Joe: The quizzes, yeah. Bill had it right, and then all the magazines… does he really love you, or references just too ingrained, and then it’s likely…

Kyle: Yeah, exactly. But the Cosmo quiz…

Joe: The Cosmo quiz, that’s it, yeah.

Kyle: It still goes on.

Joe: And then they add 12 things that will change your life, and number seven you can’t miss, and after number seven, and…

Kyle: The one part that I hope will get better, though, is the way those articles are delivered. I hate when they’re delivered in a slide show format, and I think the tide might be turning on that, this idea of just trying to rack up pages and ad views through creating the worst user experience as possible. I think that part might be finally starting to shift. A big reason is because of ad blockers and display ads rates started going down, publishers said. Well, let’s just make the ads more annoying, let’s just make them bigger and then we’ll get people to click on them. Or let’s make them click on more things. And then ad blockers came along, and now it’s reported—some stats say up to 30% of people have ad blockers. And so, it sucks for publishers, but it is gonna force us to get better, and hopefully get rid of all of that annoying stuff.

Joe: And so, because you don’t use banner ads and display ads, you can speak freely about your true feelings about them, and I’d love to hear that.

Kyle: So, we did have display ads on the site for a very long time, and I’ll break some news to you, but we just removed our last display ad last month.

Joe: Congratulations.

Kyle: Thank you, it was a good feeling. So, I do think that is a dying industry, not only because it’s incredibly hard as a publisher. You’re getting paid a dollar or two dollars per thousand pages. Good content is incredibly expensive, and that’s a model that doesn’t work. It also doesn’t work for advertisers. It’s not a good format for teaching us about new products. I was at a conference a couple of months ago, and there was a representative from Taco Bell. And she was saying, ‘When I buy 5,000 points on cable TV, I know exactly how many Beefy Bean Burritos I’m gonna sell on Friday.’ She can tell exactly.

Joe: I can see that algorithm.

Kyle: Yeah. But when I buy 50 million impressions on a banner campaign, it’s a shot in the dark, we’re just hoping. And that, I think, has to change. We have to be able to provide advertisers some clarity on ROI. And that’s why, so we call our model the performance model where we don’t make advertisers pay us unless they’re successful with their campaigns. It’s a lot more risk, we take a lot more chance up front, and sometimes it doesn’t work. But when it does work, not only is it better for the user, because they’re not having a bunch of annoying ads in their face. But thankfully the rates are much better too, and more sustainable.

Joe: And this insight that you have on why this is a better way to be, are you in a place where you just say, ‘This is what’s right for my business’? Or do you feel strongly enough about it that you would advocate for it, that you would create your own content, as CEO of a media company trying to urge for the greater good, that the industry should go this way?

Kyle: Yeah. I’m doing my darndest to convince people to give it up. So, no, I don’t think it’s just for me, I think it’s good for everybody and honestly, it’s good for me too if other publishers go this direction, because one of the challenges that we have is to train advertisers on this model. And often times it means them investing in some technology to help track what’s happening, or it might mean I’m hiring somebody to manage a performance program. So, if more publishers do it, it’s good for me too. So, I’m on a mission for sure.

Joe: Cool! And along those lines, can you explain a little more about how your model works exactly? I don’t think we covered that.

Kyle: Yeah, so I’ll give you an example. So, Lyft is a partner of our and we partner with Lyft to create both videos and written content that’s in our voice, but also represents their brand. And because we’re not just putting an ad up, but we’re writing about a company, we’ve been very choosy about who we put on the site. In fact, we have twice a week what we call a deal panel, and our sales team has to bring to the editorial team any deals they’re working on, so that we can kick it around and make sure it’s something that’s actually a good deal for our reader, try it ourselves, and then as a team we vote on whether it’s something we want on the site. And that means 95% of the advertising deals don’t go to fruition, but the 5% we invest in heavily, not in dollars but in time. We get to know their business model, we get to know their culture, their values, we get to know what works for them on the marketing front, and then we’re able to act almost like an agency, to create content that converts and, in Lyft’s case, helps sign up new drivers. And we don’t get paid until those new drivers are signed up. So every time a driver signs up and gets their first paycheck, we get a check too. And we like it, because everyone benefits from it. Lyft is getting new drivers, our readers are making extra money, and we’re making money to continue to grow.

Joe: It’s great. So, it’s sort of a hybrid, there’s elements of influencer marketing where you’re the influencer.

Kyle: Sure.

Joe: Elements of PR, because you’re obviously putting content out to the masses, and then elements of the financial benefit to the reader as well, so they’re coming for not—I wouldn’t say like a deals site, but a smart buy site, a variation on that.

Kyle: Yeah, I think as a publisher… I don’t want to lose any advertisers, but we would write about these companies anyway, right? This is the kind of stuff we want to write about, or we wouldn’t promote it to this level, or go through the amount of work we do. But that’s really the metric for the model for us—is this somebody we would wanna tell our friends about? And if the answer is yes, then they earn a place on the site. If it’s no, find another outlet.

Joe: So, on YouTube and in other places, there are clearly influencers that are out there, and there are people who have built names doing everything from just opening boxes up and showing you what’s in it, to reviewing restaurants and food. And so, it seems inevitable, and correct me if I’m wrong, that you’re gonna have some people that are producing content for you that are gonna get some traction for themselves. People are gonna search out the names of the authors… And so, do you have an awareness around building your own homegrown celebrities in-house, and…? You are selling your influence, and so you can unlock a lot more value by building brand power through these people in your organization. How do those conversations go?

Kyle: Yeah. Typically, the question- because this is a big debate in the industry right now. Well, first of all we create all of our content in-house, so we’re not outsourcing any of that. But we have decided on the strategy to not keep our writers and our folks going on video-anonymous. We want them to build their own brands. And sure, there are risks with that, but they are ones I’m comfortable taking, because with personal finance, as I said before, we need more than anything our readers to trust us. And we need them to know that we are real people, and know what our fact checking policy is, and know how we decide on advertisers. And so, if they can get to know our writers, or our hosts that are on Facebook live, that’s incredibly powerful from a trust angle. And I do think there is the ability to leverage that down the road. So, when you think about…for example, there’s this show called ‘The Pioneer Woman’, if you’ve ever heard of it. She has a cooking show on the Food Network, I believe. She started as a blogger and just taking photos of what she was making for dinner. And now she’s gone on to have a TV show and, I think, cook books… If one of the folks on our team was able to have that path, that would be incredibly exciting.

Joe: Yeah, it certainly doesn’t do anything but help, The Penny Hoarder to have that as their launch pad.

Kyle: Absolutely.

Joe: And it creates you as a launch pad. And then, obviously, it will circle back around as a destination too, because I think if history serves, you’re successful, we’ll migrate over into Facebook live and that will be a place where you’ll have anchors, you’ll have known people, and people will be migrating to you, maybe.

Kyle: We’re calling ourselves a platform neutral site, meaning we don’t really care if you come to the thepennyhoarder.com. I mean, we’d like you to, but we just want you to interact with our content in whatever format or platform you are most comfortable with. So, if you get all your news from Instagram, which might be a thing, we just hope you’ll interact with our news on Instagram. And so, every platform we create really specific content for, and we’re happy with our readers just staying in those particular platforms, not coming back to us. So, it makes sense to have a model where we’re building influencers in our site. Because if they’re interacting with those influencers and their networks, that’s still good for us.

Joe: And there you’re dividing your talent up by platform as well? So, is an Instagram person mostly shaping the content for Instagram? Obviously, different social medias have different voices and tones, and…

Kyle: Yeah, they do. So, it depends a little bit on the network. So, for Instagram or Snapchat it is a company-branded channel, so you’re not really getting to know an influencer on those channels. But with Live… we call it live because we’re hoping to launch on other platforms other than Facebook, you do get to know the influencers. Christie Post, for example, who is one of our hosts, she can just—previously she was at ABC news, she has a growing fan base that tunes in just for her broadcast.

Joe: Great.

Kyle: And that’s the kind of thing we want to encourage.

Joe: This is an idea. We’ve done some work with HSN, and one idea that I tossed out that I think is interesting, obviously it’s not an original idea because Netflix and Amazon are doing this, but it would be interesting, a platform like HSN, for them to do a sitcom, or some generalized content, and then work in the products into that. How far does the media vision extend for you beyond just talking heads reporting?

Kyle: Yeah. I can’t share too much here yet, but I will say we’re definitely thinking about it, and definitely taking steps towards it. Since our model allows us to be neutral to the platform, we want to take our content to other mediums for sure. So, we’re actively planning that.

Joe: Cool, that’s exciting.

Kyle: Yeah.

Joe: We’ve done a little thing called a shout-out. You’re in the community a lot, you have a lot of people coming to you and presenting things to you. Who is someone—that could be a non-profit, it can be a start-up, it can be an artist, someone that… doesn’t have to be just one either, but someone who jumps out in your mind that what they’re doing is really cool, and they could benefit from having a few more eye-balls on them?

Kyle: I don’t know if they need more eye-balls, but the TEC Garage is such an incredible resource here in St. Pete, and Tonya Elmore and her team does such an amazing job. There’s a lot of cool start-ups in that space, and I understand they have a long waiting list, and they’re building a new innovation center for it. So, definitely a shout-out to them. And I think I’m going to give a shout-out to… he doesn’t necessarily own a business, but somebody has been such an incredible help to me. Ashby Green, who was a CFO at Kobie, has absolutely been fantastic. I can’t tell you the number of relationships he started for me, that have not only been helping me personally grow, but put money in my pocket. So, a shout-out to Ashby.

Joe: We were doing a thing called the St. Petersburg Group, which it’s sort of a civically minded consulting group, and Ashby has been my partner in crime on that too.

Kyle: Oh, nice.

Joe: We’re pretty close, we actually just went to a… just got back from camping in South Carolina together last week.

Kyle: Nice!

Joe: He’s a big fossil geek, like I am, so we were literally in the river for two days straight, digging up for shark’s teeth and things like that.

Kyle: That’s cool.

Joe: That was cool. So yeah, I’m a fan of…

Kyle: Is this tent camping, or…?

Joe: It was tent camping for us. He brought a pop-up trailer, which yeah, I call it a little bit of a cop out, but it was the first time he’d used this, so it took us an hour to figure out. We had the tent up in six minutes on our site, and then I’m over there sweating, trying to figure out which bar goes where to get this pop-up trailer. And then on the way home, he… the bracket that holds the tire, the axle broke, so we were pulled on the side of the road…

Kyle: Oh, geeze!

Joe: …in Georgia, trying to, with the jack out of my car and the jack out of his car, trying to get this camper popped up so we can change the tire, and we ended up having to get a mobile welding unit out to weld or put a new bracket on.

Kyle: That’s insane.

Joe: Yes. It was an amazing day.

Kyle: I’ll say, it was like a day for all that trouble. Hope you got some good campfire food.

Joe: Yeah. And we found some good teeth. It’s fun. He’s got a cabin down on Peace River. And so, we go down there and right outside the back of it, just sit in the river and it’s peaceful and relaxing, and talk business and not talk business, and it’s just good.

Kyle: Awesome.

Joe: So, cool. The thing is well. Alright, well, I appreciate it. It’s been a good conversation.

Kyle: Awesome. Thank you.

Joe: Yeah, a lot of great content

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About the host

Joe Hamilton is the CEO of Big Sea and a founding Insight Board member at the St. Petersburg Group.  Joe brings a strong acumen for strategy and positioning businesses. He serves on several local boards, including TEDx Tampa Bay, which grew his desire to build a platform where the area’s thought leaders could share their valuable insight with the community at large.


About the St.Petersburg Group

The St. Petersburg Group brings together some of the finest thinkers in the area. Our team is civic minded, with strong business acumen. We seek to solve big problems for big benefit to the city, its businesses and its citizens.