When Tiffany Penn started Penn Tales (“a lifestyle brand for the unapologetic woman”), she clearly had the goal in mind of “working towards her freedom.” She did not want to work for a company for the rest of her life, that wasn’t her own, of course. And she wanted to focus on women making moves like her; working a full time job but also having a side hustle, doing what they are truly passionate about. To take this a step further, Tiffany wanted women like her to come together and share in a non-judgmental environment and have open conversation about how each woman has reached and is striving to reach her goals in business and life. What spawns from this idea is, My Army is Female, a signature event of her larger company, Penn Agency. An intimate gathering of like-minded women, doing all types of business but with the goal to meet other women, share and encourage them on their road to their freedom.

In this Spring Edit, September Set wanted to feature women fiercely following their passions and bringing other women along on their journeys, so that we all can learn from each other. This is why we were excited to feature Tiffany and showcase her recent My Army is Female event at Michelin Bib Gourmand Awarded, Mola, a woman-owned restaurant in the heart of Adams Morgan, DC.

It was a weekday evening in March and we gathered at Mola for an experience of not only great networking and conversation but also great food. After cocktails and networking, we sat down and Tiffany lead the discussion that posed questions ranging from how we felt about uplifting our sisters to how relationships (marriage for example) affects our lives. It was indeed a no-judgement zone and a comfortable place to share. When September Set sat down to interview Penn a few days later, she shared with us that she gets nervous and jittery during each event, but we could not tell. The delivery and flow of the event was seamless and classy; a testament to Penn’s hospitality industry background, having worked in places like the Mandarin Oriental and now managing popular DC restaurants, Lost Society, Gryphon and SAX; one of the few female managers in a male-dominated industry. “I want to hear the good and the bad of a woman’s path and that’s authenticity,” says Penn on one of her motivations for My Army is Female.

What’s next for Penn? She’s taking My Army is Female on the road and next month will host a gathering in Philly and another event in June that will include both men and women to give men “a realm to exist,” she says that they don’t often have the opportunity to express themselves. Judging from the event in March, there will be no shortage of mind-expanding conversation. Long term goals include taking My Army is Female to spaces that will share the energy and culture provided by special events like Art Basel, as well as retreats and additional Penn Tales events in international locations.

Personally, Penn would like to get to the point where her businesses are running smoothly, and she can firstly take care of her mom and “disappear…enjoy life; be anonymous,” she says. She gets enjoyment out of pleasing others and showing others the road to success, not just the success. What advice does she have for women, “It’s not going to happen overnight and there will be a lot of blood, sweat and tears before the congratulations. You are going to fail but there is a light at the end of the tunnel.” In other words, keep going even after failure; spoken from a woman who’s first tow business ventures closed but she is reaching her stride the third time around. Most importantly, as we closed our interview, Penn said, “you need to be happy within yourself.” Enough said.

To get more information about Penn Tales and upcoming events visit:

Website:  https://penntales.com/ Instagram: @penntales