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What it’s like to run a personal finance website

A digital media entrepreneur says that "fundamentally, the thing that you worry about the most is taking care of your employees."

7 min read


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SmartBrief illustration by James daSilva

This is the latest in a series called Lead Human, which features interviews and profiles conducted by Elliot Begoun in search of answers to the question “What is it like to be a leader?”

Have you ever experienced that intuitive sense that a person you’ve just met is merely at the beginning and is destined for bigger and better things? That is exactly how I felt after this interview with Kyle Taylor, founder, and CEO of The Penny Hoarder.

Taylor has taken The Penny Hoarder, whose mission is to put more money into people’s pockets, from a personal blog to one of the largest publications on the web. He has created a new kind of personal finance media with stories about real people. The Penny Hoarder offers actionable money tips that focus on making a difference in their millions of monthly readers’ budgets. It’s an awesome mission being led by an emerging young leader. I hope you enjoy this interview.


What keeps you up at night?

“Everything!” he laughed

“I think, fundamentally, the thing that you worry about the most is taking care of your employees. And, even though we’ve been fortunate enough to make sure that we’ve never had to worry about a payroll, it’s the thing that I think about the most. Like, if something were to go wrong, I’m first and foremost letting down these 60 people.”

Taylor added that he also worries about the speed of change.

“In digital media, it’s changing so rapidly. Business models that worked just a couple of years ago no longer work today, and traffic acquisition strategies that worked a couple of years ago no longer work. So, there’s a constant need to keep pivoting and keep adapting.”

How do you deal with fear and doubt?

We spent quite a bit of time on this question. Taylor told me, “This is kind of my favorite topic to talk about.”

“I’ve been very open and honest about the fact that I think we all, in some way, face ‘imposter syndrome,’ myself included. Prior to opening an office 18 months ago, I’d been running this solo for four and a half years, and for the two years prior to that was making decent money. I was on a runway to do several million dollars, and I still hadn’t hired anyone, for no other answer than fear. I was scared to take on the liability, as I mentioned at the top about making sure I could pay somebody each month. I was also a little nervous about whether I had what it took to be a leader and a manager.”

“I still have that today, imposter syndrome, but in different ways. I no longer wonder if I can be a good leader or a good manager, I feel confident in that. But now, I think about, okay, I’m running the 87th largest publisher in the country — or whatever the number is today — do I really have what it takes to be in the top 5? Do I have what it takes to be a BuzzFeed? I still face that.”

“And the one thing that helps me get past it — well, two things — one is talking about it openly I feel marginalizes it, makes it smaller. And then the second thing is, when I’m in a situation like that, I try to picture those CEOs that I admire, and I say, ‘Did Jeff Bezos know how to create the largest distribution company in the world 10 years ago?’ And the answer is no. ‘Did Mark Zuckerberg know anything about S-1 filings and going public 10 years ago?’ No. They learned it along the way, and I can do the same.”

What do you do when you make a bad decision?

“Well, I think it depends on how bad of a decision I’ve made. If it’s a decision that, let’s say, totally ruined a part of the company, or that has some real long-lasting effects, I think it’s important to give yourself permission to take a short sulk. For a long time, I would beat myself up about that and say, ‘You can’t focus on this, get back in it.’ And I stopped doing that because I think it’s pretty human to feel a certain sense of regret, or just feel sadness, or whatever it is when something doesn’t go the way you had hoped.

“I don’t dwell on it forever, but I do sort of allow myself to feel that for a little while. And then I think back to all the other times where something hasn’t gone my way, and we eventually figured it out, and that’s usually the part where I can start to turn it around and start to think about what we can do differently.”

Taylor went on to add, “If it’s a small loss, or a poor decision that didn’t go well, I think first, if it affected other people, apologize for it, and then try to move on as quickly as possible. Because, that small stuff, I think, is what can sort of eat up your day and keep you from doing big things.”

How do you make time for yourself?

“It’s pretty breakneck for me, but I have set up a couple of hard-and-fast rules. One is, I take every Thursday afternoon off work. I turn off Slack, I turn off email, and I hang out with my friends and my nephew.”

His second hard-and fast-rule: “Saturdays at our house are reading days, so we’ll crack a bottle of champagne and we read all day. That’s the thing that re-energizes me for the week and gets my mind thinking.”

What have been some surprising leadership lessons?

“My words carry a lot more weight than they used to, and I think that’s been one of the more difficult things. I’m naturally a kidder, a class clown, and I realize now, over the last 18 months, that just saying something off-handed, or a throwaway comment, other people take that very seriously. I’ve recognized that a couple of times on the strategy front, where we’ll talk about an idea or a design or something and I’ll say something like “oh that’s kind of cool” and realizing that that’s not just me thinking that’s cool, that’s a green light to move forward with a project.”

What have you learned about connecting with, motivating and engaging people?

“Not to sound like a cliché here, but I think a shared mission is important and probably the thing that’s made this work the best. Our mission at The Penny Hoarder is to put more money in people’s pockets and we talk about it ad nauseam. Everything we do, we say, even … I’m in an advertising meeting every day where we talk about the advertisers that want to work with us. We talk about it in that context. ‘Will the advertiser put money in people’s pockets?’ I think by constantly bringing it back to that, not only has it become a shared goal, but it helps self-motivate everybody because we realize that we’re all working towards the same thing, and we’re all really trying to make a difference. We’re not just trying to make a dollar.”

What do you wish your current self could tell your former self?

“I would tell myself, “You’re capable of way more than what you think.” I suspect my future, future self will tell me that as well. All those little limitations that you put on yourself, aren’t real. Those are limitations in your head.”


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Elliot Begoun is the principal of The Intertwine Group. He serves as a consultant and thinking partner helping emerging food and beverage brands gain the distribution and win the share of stomach they need to grow. His articles appear in publications such as the Huffington Post, SmartBrief, and Business2Community.

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