May 31, 2017

Kyle Taylor was broke.

It was 2009. Taylor was 25, working as a field director for the AFL-CIO in Louisiana. His mission: Pressure then-Senator Mary Landrieu to vote yes on the Affordable Care Act. His employer flew him out, put him up in a tiny apartment and expected him to get to work.

There was just one problem: He couldn’t afford any food.

A two-time college dropout, Taylor had racked up $30,000 in student loan debt. He had another $20,000 in credit card debt on top of that, a by-product of his meandering existence as a political organizer. Seven years after dropping out of school the first time, Taylor was hungry. And payday was weeks away.

“That was a real turning point in life,” Taylor said. “Going two or three weeks where I had to look for change on the side of the road to buy a cup of ramen or a can of tomato soup, or going into the hotel next door to try to get a banana out of the continental breakfast…not things I’m proud of. But it was a moment that was kind of rock bottom for me.”

Today, it’s hard to reconcile that broke 25-year-old with the entrepreneur he eventually became. Over the next few years, Taylor dug himself out of debt one blog post at a time and built a multi-million dollar media company along the way. The Penny Hoarder, which began in 2010 as a Blogspot site, is on track to make $40 million dollars this year and was named the fastest-growing private media company by Inc magazine last year.

The company, which is headquartered in downtown St. Petersburg, now counts about 15 million unique pageviews, 4.9 million Facebook likes and, by the end of the year, about 100 employees. But to understand how it became a success, you have to understand how Taylor began his adult life as a personal finance failure.

‘There was nothing to show for it’

Taylor was a pretty frugal kid.

Growing up in Tampa Bay, he had a knack for finding strange ways to make and save money, he said. During a recent interview at The Penny Hoarder’s offices, he recalled that his family sometimes did side jobs together — like when his mom took them as undercover mystery shoppers to restaurants, retailers and even, once, Universal Studios.

But those tight-fisted tendencies gradually faded over the years. About three weeks into his freshman year at the University of South Florida, Taylor spotted an ad for the AFL-CIO to knock on doors for the 2004 election. When then-Senator Kerry lost, Taylor dropped out of college to work on a campaign in Austin to persuade voters to create a public park. He was hooked.

But those jobs hurt Taylor’s bank account. By the time he was 25, he says he’d signed about 21 different leases, mostly efficiency apartments. He attended the University of Colorado for a couple of semesters before dropping out.

“I wasn’t making good decisions,” Taylor said. “I can’t say that there were any toys or anything that really stand out. That’s what makes it worse, is that there was nothing to show for it at the end. I was living out of a suitcase, essentially, going from town to town. A lot of debt.”

Tired of campaign life and homesick, Taylor moved back to Tampa Bay and resumed his childhood tradition of picking up side gigs for some extra cash. That’s when he started blogging.

‘I think the name just occurred to me’

Before The Penny Hoarder was a multi-million dollar company with dozens of employees, it was just Taylor writing posts about all his odd jobs. His little blog was gaining some traction with clicky headlines like “How I got free beer and made $5,000/month by auditing liquor stores” and “The best mystery shopping companies to work for.” He registered on Dec. 15, 2010 and moved away from Blogspot to give the site a bump from search traffic.

“My PR team, I’m sure, would love me to tell some wonderful story that I did all of this consumer research,” Taylor said. “But, truth be told, I think the name just occurred to me. It was a hobby. And frankly no one was reading it yet.”

For the first two years, the site was basically a hobby. But, gradually, the audience and revenue started to build. Back then, The Penny Hoarder made money mostly from native advertising. Companies paid Taylor a flat fee — around $75 to $100 — to write posts that showed how their products could help save readers money. But that wasn’t scaleable — there’s only so many posts he could write per month.

So, Taylor started looking for help. He tried several freelancers, but none of them delivered the approachable, first-person stories of personal savings that Taylor was looking for. Frustrated, he Googled “blog management” — a search that ultimately kicked off the site’s next phase of growth.

‘I would never have done this if we had investors.’

The person at the other end of that Google search was Alexis Grant, a digital media entrepreneur who would eventually become the third employee at The Penny Hoarder. A graduate of Northwestern’s Medill School of Journalism who left her job at U.S. News and World Report to found her own business, Grant was exactly what Taylor was looking for.

He just didn’t know it yet.

During a phone call in 2014, Taylor explained his misgivings about his previous freelancers. Grant, whose company managed blogs for companies like Brazen and Eone Timepieces, persuaded him to let her company try one post.

“I read it, and first of all, the writing was way better than anything I had ever done,” Taylor said. “But it was the same kind of stuff I was writing about. I think the reason it worked was, she had this network of freelancers. Many of them were hustlers as well. They were not just writing, they were doing side gigs as well.”

That post led to a contract. Soon, Grant’s company was producing three or four posts for The Penny Hoarder every week. A few weeks in, they upped the contract to 15 posts per week. Her team began managing The Penny Hoarder’s social media presence, which freed up Taylor’s time to develop the advertising network. At the end of 2014, it was clear The Penny Hoarder was going to make well over a million dollars by the end of the next year, and Taylor still didn’t have any employees. If he wanted to keep growing, he needed help.

So, in 2015, he made an offer to buy Grant’s company and bring her network of writers and social media experts in-house. But Grant wasn’t sure she wanted to sell. Amid the craziness in modern media, she’d eked out a reasonable work-life balance at her own business. She didn’t report to anyone (except clients). She didn’t have investors.

And, by the time the talks got serious, she was pregnant. Taylor’s startup had two employees, so it didn’t have a maternity leave policy yet.

“It was a hard decision for me, because I really enjoyed running my own business, and I found entrepreneurship to be a really good fit for me,” Grant said. “…I would never have done this if we had investors.”

But ultimately, she decided to sell (both Taylor and Grant declined to disclose the terms of the deal). They quickly hammered out a maternity leave policy that allowed for eight weeks off. On July 2, The Penny Hoarder officially had its first executive editor, and its third employee. But it didn’t yet have anyone dedicated to overseeing the business full-time, and the business was growing faster than Taylor could handle by himself. He needed an expert.

‘When scaling this to a very large size, it’s intricate.’

Vishal Mahtani was on vacation in the Caribbean when he got a message from a friend.

“You need to talk to him now,” Mahtani recalls his friend saying about Taylor in 2015. “He wants to meet with you.”

A few months before his vacation, Mahtani had completed the sale of his online kids clothing business, Kindermint, to a San Francisco-based company called Thredup. He was trying to catch up on some time with his family. But he was intrigued by Taylor.

“I saw his passion and determination,” Mahtani said. “He was driven. You could pick that up from the call.”

A few days later, the two were having lunch in St. Petersburg to discuss the company’s prospects. That summer, he officially joined the company. Almost immediately, he did two things: put into place a system to track the revenue The Penny Hoarder was bringing in and hiring account managers to oversee The Penny Hoarder’s growing business.

Mahtani was an unlikely find among Tampa Bay’s entrepreneurs because he intuitively grasped The Penny Hoarder business model, which is rather unusual among media companies. It’s called “performance marketing,” and it varies from many of the ways that advertising or reader-supported newsrooms traditionally keep their businesses afloat.

Here’s how it works: Say General Mills has a $500,000 advertising budget. They could go to The New York Times and purchase a full-page ad. Or, if they wanted to market a specific product — a new cereal, for example — they could ask The Penny Hoarder to write a post about a new deal for potential customers involving five new coupons. Because The Penny Hoarder can track its readers, the company can tell how much of its audience actually took advantage of the deal by downloading the coupon, for example, or plugging their email addresses into a signup field. The Penny Hoarder then gets a fee for every user who takes those desired actions.

“It allows us to align very, very well with our advertisers,” Mahtani said. “It forces us to really get to know who our advertisers are, what they’re trying to do, what their goal is, for the whole campaign.”

The “vast majority” of The Penny Hoarder’s annual revenue comes from this performance marketing, Mahtani said, although the company also does some branded and display advertising. The company’s clients include banks that are hoping to market credit card promotions, Uber (which is trying to find drivers and users) and CreditSesame, a freemium service that provides users with credit scores.

This approach is reminiscent of e-commerce businesses that have taken root at several major news organizations, said Ken Doctor, a media analyst who’s written for Politico, The Street and Nieman Lab. The New York Times recently acquired The Wirecutter, a product recommendation site that gets a commission for each sale it helps drive. Gizmodo Media Group now makes 25 percent of its revenue from commerce transactions driven by affiliate partnerships. And Vox Media also in 2016 began an e-commerce push, following in the footsteps of other digital media companies.

Most companies, Doctor said, have different teams that produce commerce-driven and editorial content, but not all. Condé Nast caused a stir in 2015 when it announced that it would ask its journalists to create native advertising for the company. Others, such as Vox Media, have separate commerce and editorial teams.

“In all of these deals, the question is, who produces it?” Doctor said. “Are they independent? Are they disclosing it to the readers? And do the readers buy that the editorial content is trustworthy?”

At The Penny Hoarder, the site’s writers work with its account managers to figure out which stories are right for its audience, Taylor said. They jointly decide to turn down about 95 percent of advertisers, and their primary rubric is found in the company’s mission: “Put more money in our readers’ pockets.” If it helps readers save or make money, it’s in. If it doesn’t, it’s out, Taylor said.

The Penny Hoarder’s policy is to include a disclosure whenever the company does an affiliate post, said Maryann Akinboyewa, a spokesperson for The Penny Hoarder. The company is in the middle rolling out an “Honest Abe” disclosure that will go at the top and bottom of articles that contain sponsored links.

To encourage collaboration across teams, The Penny Hoarder has company-wide goals, such as pageviews and revenue, that change each quarter. If the company meets its goal, the entire company gets bonuses.

The Penny Hoarder’s business model — and the way it produces commercial content — differs from many traditional media companies. Collaboration between account executives and editorial employees breaks the divide that many companies have established to avoid commercial interests influencing newsroom decision-making. But Taylor says the model is preferable to the alternative and notes that most of the content The Penny Hoarder produces is not driven by performance marketing.

“The other model of doing things is putting more and more annoying display ads and video pre-roll all over your content — that’s the same thing,” Taylor said. “As a publishing company, you’re making a decision to put that right alongside your content. And I don’t think, for the reader, it’s any different. They associate the same thing together. At least with performance, you have some say-so, and you get to choose. It also doesn’t mean you can’t still be a news site.”

Even though the company is making millions, Mahtani says he isn’t aware of any other media companies that use performance marketing on the same scale as The Penny Hoarder.

“When scaling this to a very large size, it’s intricate,” he said. “You’ve got to know, for every single advertiser, what their KPIs are. It’s not an easy thing to execute. It’s not cookie-cutter, like display inventory, where you just put your 300 by 250 up and let the advertisers optimize.”

‘I am debt free, thank you.’

The Penny Hoarder is planning to grow a lot in 2017. It’s moving to its third office space. It’s adding dozens of employees. And, like many other media companies, it’s ramping up production of distributed content — content produced for platforms other than its website.

This year, the company plans to hire eight people to be part of a full-time Facebook Live team, Taylor said. Because viewership on Facebook Live is fairly reliable, it may prove easier to sell to advertisers than a basic post, he said.

“Not everybody wants to read a 3,000-word article about life insurance,” Taylor said. “But they might be more interested in an interview about somebody that has had personal experience with it and can share what they did. And so Live gives us a way to not only provide it in a different multimedia, but to allow the readers to interact.”

A recent experiment on Facebook Live was Purple Friday, The Penny Hoarder’s philanthropic take on Black Friday. Rather than encouraging shoppers to save money on the latest Black Friday deals, as the company had in previous years, The Penny Hoarder created Purple Friday to reward readers who planned to spend time with their loved ones. It included a giveaway, which received more than 11,000 submissions, from which 50 winners were chosen.

The Penny Hoarder broadcast some of the winners via a Publisher’s Clearinghouse-style surprise video on Facebook, Taylor said.

“One family, we gave a trip to Disney to their entire family and their two kids,” Taylor said. “Watching these two kids go nuts on camera when they found out they were going to Disney was pretty awesome. A mom wanted to surprise her daughter with a trip to Kleinfeld Bridal and buy a wedding dress. And so we took her to Kleinfeld and had one of the consultants from ‘Say Yes To The Dress’ pick out dresses for her. And the audiences got to participate and vote in real time.”

For all The Penny Hoarder’s ambitions to expand, Taylor says he’s not interested in soliciting venture funding to fuel new growth. Nor is he planning on selling the company, “I want to do this forever,” he said.

And, by trying to help readers put money in their pockets, Taylor has put some in his own, too. All that credit card debt?

“I am debt free, thank you,” Taylor said.

Disclosure: The Penny Hoarder sponsored Poynter’s 2017 Leadership Academy for Women in Digital Media.

Correction: An earlier version of this story referred to a “can” of ramen. Ramen comes in cups, of course.

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Benjamin Mullin was formerly the managing editor of He also previously reported for Poynter as a staff writer, Google Journalism Fellow and Naughton Fellow,…
Benjamin Mullin

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