Dear Penny: The Penny Hoarder’s column to debut in the Times Sunday

Filing for bankruptcy and still struggling to make ends meet, dealing with mom’s cheapskate boyfriend, and convincing a significant other that he should have paid off his student debt yesterday. 

All of these tricky situations have been the subject of personal finance blog The Penny Hoarder‘s new column, Dear Penny. Launched in March 2018, Dear Penny shares advice in those nightmarish, yet all too common situations where life and money mix. 

Starting July 29, The Penny Hoarder will team up with the Tampa Bay Times to bring Dear Penny to the Times’ readership.

Dear Penny will be featured weekly in the business section of the Times Sunday edition. It will answer tough financial questions submitted by readers, tackle awkward financial situations and deliver insight about dealing with the intricacies of money and life simultaneously.

The Penny Hoarder began the Dear Penny series earlier this year to engage readers and reduce stigma around money talk. Lisa Rowan is a personal finance expert at the Penny Hoarder and the writer behind Dear Penny. Rowan, 32, says the idea came out of The Penny Hoarder’s daily Facebook Live show that she piloted in 2017.

On the show, Rowan interacted with readers live and answered their money-related questions on the spot. That lead Editor Robin Hartill to propose the Dear Penny column. Its feature in the Times will be a first endeavor into print for The Penny Hoarder and return to print for Rowan, who scored her first writing job at 16 at her hometown print newspaper in Pennsylvania.

“We get a lot of inquiries from readers anyway,” Rowan explains. “We thought, ‘Why don’t we give it a really personal tone and a compassionate voice to answer these questions and share them with our readers?'”

Compassion is a key ingredient, says Rowan. “It has been really nice to see how much trust the readers have put in me from the very beginning of the column.”

“I don’t want people to be ashamed of the situations they’re in. I’ve made financial mistakes in my life, it makes no sense for me to scold someone for mistakes that I have also made. Instead, it’s up to me to lift people up out of those struggles and let them know that they have support and they can talk about these things.”

In a letter introducing readers to Dear Penny, Rowan made a similar appeal. “Let me put it this way: I had a completely normal upbringing before ruining it with bad relationships and college blunders,” she wrote.

“I’ve had a full-time job, owned a business and been a freelancer —and I’ve managed to recover from embarrassments and financial blunders in all of the above situations. I’ve made a lot of money mistakes in my short life, and I promise not to yell at you if you tell me about yours.

“I’ve been here before, and I know the way out.”

While The Penny Hoarder has mainly served a millennial audience, Dear Penny has covered wide-ranging questions in all stages of life, including how to get your adult child to move out, buying a house with significant other, and spending in retirement.

Rowan loves the range of these questions, and welcomes the challenge from her readers. “If they’re ready to ask a millennial their money question, I’m ready to answer it,” she laughs.

In those occasions where questions sit outside her personal purview, Rowan turns to what she calls her “digital Rolodex” of experts – usually those she’s consulted with for other stories. While she can often relate on an emotion level to feelings of shame or stigma that surround these questions, Rowan does her best to get more intricate financial advice from an expert. 

Many fans of The Penny Hoarder, a national brand, may not realize that the fast-growing media company is based in St. Petersburg. The partnership will bring the Penny Hoarder’s financial expertise directly to a local audience. It will also bring the Penny Hoarder’s financial wisdom to print readers for the very first time. 

Rowan is excited to introduce The Penny Hoarder to readers in a new way. “We are so respectful of the Tampa Bay Times and what they’ve built,” says Rowan. “They have such strong readership, especially in the Sunday edition – we’re excited to meet readers at their kitchen table or on their couch, without making them find us.”

“Being a national website, you forget about the fact that you have to build up your presence at home. I still meet people on the street and tell them I’m working with The Penny Hoarder and they say, “What’s that?”

Beyond getting the word out, Rowan is excited to be back in print under her own byline. She’ll be buying extra copies of  Times‘ Sunday editions to cut out and send to her parents. “I was totally the kid that wanted my gold-starred papers displayed on my parents’ fridge,” say laughs. “At 32, I still want that.”

The Penny Hoarder, based in downtown St. Petersburg, was ranked by Inc. 5,000 as the No. 1 fastest-growing private media company in the country for the second consecutive year.