Meet The Woman Who's Trying To Save Downtown D.C. By Doing The Unthinkable: Making It Fun

Anna Valero has few days off. The hospitality veteran’s business empire has evolved from event planning to ax-throwing and pickleball, but on a recent Friday in February, she had to fill in as a manager at her bar and event space, Hook Hall, when the team was short-staffed.

"It's kind of fun," Valero said when Bisnow caught her during the shift for an interview. "It's one of those things where there's almost a little bit of pride in the fact that you're like, 'Oh, I remember how to do this. Give me a couple hours, folks.'"

Running a bar can bring its own headaches, but these days, Valero is tackling a much bigger, more intractable issue in D.C. — making downtown cool again.

With her company taking over a high-profile Penn Quarter event space and retail programming at Franklin Park, Valero is trying to redefine what downtown D.C. can be, injecting casual entertainment into a traditionally straight-laced area that sorely needs workers and visitors to return.

“What I really like about her is that she is willing to continue pushing through any hurdle,” DowntownDC Business Improvement District CEO Gerren Price said of Valero. “She gets a vision and she really sticks to it and shows her commitment to that vision in a way that I think is really unique.”

Through Pirate Ventures, a business she co-leads with former The Apprentice contestant Steuart Martens, Valero also operates two ax-throwing venues named Kraken Axes, a pickleball venue named Kraken Kourts — slated to open soon in a former department store — multiple festivals branded under Drink the District and an events team, Corsair Consulting.

Despite those varied pursuits, those who work with Valero say her attention to detail is a hallmark of the ventures she leads, and the care she takes to integrate into a community for each new space goes above and beyond the work of a typical tenant.

“What is needed most — and there is the least of — is large venues that have the opportunity to bring large groups of people together. That is really Anna’s background and Anna’s specialty,” said Zach Wade, an executive with MRP Realty, Pirate Ventures’ landlord at its upcoming 70K SF pickleball venture. “At this moment in time, it’s really a perfect fit for her skill set.”

Valero is still pushing to expand her business, looking for more space for Kraken-branded locations in the Washington-Baltimore corridor and growing its third-party event production business. 

But now, Valero is taking on projects in an environment that has proven dicey even for the savviest of retail operators — D.C.’s beleaguered downtown. 

Piece by piece, Pirate Ventures is transforming weathered commercial buildings and neglected public spaces into venues that invite and deploy a variety of uses. Valero is betting that a downtown considered “comatose” by some can be revived with the kind of well-calibrated, creative experiences that have become Pirate Ventures’ trademark.

In the process, she hopes she can remind residents that after a tough three years, D.C. can emerge as something better than it was before.

“When you say Franklin Park, [people] have a stigma in their head with what that means. We can be part of the effort to change that stigma to being something that D.C. is known for,” Valero said. “That's powerful.”

From Transplant to Champion

Valero first moved to Washington, D.C., in 2006 to study at American University. She majored in communications, but not long into her studies she began interning for Sitar Arts Center, a nonprofit based in Adams Morgan focused on music education.

It was there that Valero said she first developed an interest in event planning with the community-oriented ethos of a nonprofit. She founded Valero-ing LLC, an event planning business, but in 2017, Martens, a fourth-generation Washingtonian who had resurrected Taste of DC, brought her aboard to expand the brand.

Not long after, the two launched Pirate Ventures, uniting under a corporate motto to “deliver the unexpected.”

“What we're both really passionate about is live events. We're really passionate about how they can impact the community, and how they can be used to really support especially the small-business community in D.C.,” Valero said. “When we decided to join forces … it was really with that in mind.”

Not long into their partnership, Valero and Martens scored their first hit. Valero's team began setting up an ax-throwing activity at events and branded it Kraken Axes, which proved popular with festivalgoers.

“People would start calling us between festivals, saying, 'Hey, can you put us in touch with those Kraken people?'” Valero said. “You're like, 'Yeah, sure, hold on a quick second,' and you push the hold button on the old-school phone and you're like, 'Hi, I'm the Kraken people!'”

The firm’s ambitions quickly grew into bricks-and-mortar. In 2018, the first  Kraken Axes location opened at 3400 Georgia Ave. NW before landing at a permanent location at 840 E St. NW in Penn Quarter that’s still operating today.

In place of the original Park View ax-throwing space, Pirate Ventures built Hook Hall, a bar and event venue spanning more than 13K SF that Valero conceived as a year-round incubator for more ideas like Kraken Axes.

The venue opened in July 2019, eight months before the pandemic struck. But rather than collapse, it quickly became the foundation for Valero’s rising profile in the District.

Shortly after sit-down dining was banned in D.C., Valero reached out to the Restaurant Association of Metropolitan Washington to offer Hook Hall as a staging area to distribute meals to furloughed restaurant workers.

The venue’s loading docks, which DCist described before the pandemic as set up to wheel in a Lamborghini, were instead receiving “truckfuls” of perishable goods from restaurants that were suddenly liquidating supplies, Julie Sproesser, managing director of RAMW, told Bisnow.

“We were texting every day to make sure this effort was pushing forward,” Sproesser said.

Those efforts continued for almost a year and expanded to include a Worker Relief Fund that raised roughly $1M for affected members of the hospitality industry. They also brought Valero acclaim — Restaurant Business Online hailed her as a “pandemic hero.”

Valero shut down the free meal distribution effort at the end of June 2021, weeks after pandemic restrictions had lifted, in part to ensure workers were still covered before their first paychecks rolled in.

That concern for her industry and her city continues to motivate Valero. She noted the sector was responsible for just under 1 in 10 jobs in the District economy before Covid, but it lost about 6,000 jobs between March 2020 and December 2022, according to District data. It still has not recovered its pre-pandemic share of the D.C. workforce.

To help build career paths for affected workers, Valero said she is developing a workforce training program for service industry workers that she hopes to launch by the end of this year. Post-pandemic, she views that kind of work as not only important for hospitality, but also for the broader revival of D.C.

“We were fortunate to be able to do what honestly, as event production people, came really naturally: bringing together different components in order to run a logistics operation,” Valero said. “That type of ecosystem model, it's what we believe in. Yes, it did get a lot of attention during the pandemic, but I think that's the exact same model that's going to allow D.C., as both a business community and as a greater community, to continue to thrive.”

Filling ‘A Human Need’

On a recent tour of 918 F St. NW, now marketed as the National Union Building, Valero moves up and down the six-story property via its original 19th-century elevator. Wearing a Pirate Ventures vest on a cold February day, she's eager to show off the historic features in the 28K SF space, which plays host to corporate clients for rates starting at $200 per hour. 

A decade ago, the building played host to another up-and-coming firm, the buzzy tech startup LivingSocial. But Valero is quick to differentiate her business model from theirs. 

When the daily deals and events startup vacated the space in 2014, it left behind a venue that had served many of Valero’s colleagues in the hospitality industry. But where LivingSocial failed, Valero thinks her firm can find success by relentlessly testing new ideas to stay in touch with the present needs of the downtown community.

“We are always keeping our finger on the pulse of, not what do we think the community wants, but how do we continue to be creative and see where trends are going in order to curate an experience that would be welcomed?” Valero said. “Oh and P.S., we have space to do it, and I think that's the differentiator for us.”

Public and private sector leaders are hoping to see more experimentation downtown. Retail vacancies in the submarket were stuck at nearly 20% this winter, according to brokerage firm Dochter & Alexander. At least 48 restaurants closed in D.C. last year, including downtown mainstays like Grillfish and Cafe Mozart. And of most concern for retailers and property owners, less than half of D.C.’s office workers have returned in person, according to Kastle’s back-to-work barometer.

Price, with the DowntownDC BID, said more experience-driven retail and event spaces are an important piece of the puzzle for the central business district's revival, particularly in buildings that once served as offices like the National Union Building.

"One of the beautiful things about the moment that we're seeing here [is] obviously there's a lot of challenges, but there's been emerging spaces where we're seeing opportunity," Price told Bisnow. "Where Anna comes in is she has this great experience in creating uniquely curated experiences for people ... and I think that sort of creativity is exactly what the moment is calling for."

Valero's firm capitalized on the opportunities of a changing downtown in 2021 when it won a competitive process to operate The Springs at Franklin Park, a new 2K SF café that the DowntownDC BID expects to open this year. 

“I'm really excited that she is on board and a part of this project to help bring new life and vibrancy to Franklin Park,” Price said.

The park has undergone a transformation in recent years spearheaded by the National Parks Service, which owns the land, and local officials working in partnership with the BID.

Beyond coffee and snacks, The Springs will offer to-go picnic baskets and a varied menu supplied by local vendors. Valero is also planning to coordinate events at the park, like after-work yoga or farmers markets on the weekends, to reintroduce D.C. residents to their downtown.

“You can sell the best coffee all day long, but unless you truly activate the park in a way that draws people in … all of this work will be for naught in a few years,” Valero said.

Pirate Ventures won the right to operate the café after hosting a multihour tasting and presentation for leaders from the agencies involved in the process at Hook Hall. John Gogos, Pirate's broker with Papadopoulos Properties, said Valero's ability to deliver above and beyond expectations when presenting new ideas to landlords or officials is a key ingredient in her success.

“[Pirate Ventures] is not like an Aramark or some out-of-town group that’s telling Washingtonians how we should be enjoying our lives,” Gogos said. “They are, she is, based here. This is her home, and I think that that allows her to really understand the market that she’s serving.”

The Franklin Park project is part of her bid to help the District attract workers back downtown. Despite being a purveyor of off-the-clock experiences, much of Pirate's business relies on office workers — 80% of the National Union Building's event customers, for instance, are white-collar workers. 

But an entrepreneur who has built her brick-and-mortar empire on ax-throwing bars is perhaps better equipped than most to factor risk into a venture — Valero notes that Kraken prides itself on having zero “ax-cidents” despite the potentially risky mix of sharp objects and alcohol.

The Kraken business is expanding, too. MRP is working out a plan to keep Kraken Kourts around after it redevelops the old Forman Mills building, where the pickleball concept is operating on a short-term lease. And Valero is working with Gogos to find additional 25K to 50K SF spaces for the pickleball concept across the DMV. 

But her ventures downtown are arguably riskier than large-format venues for trendy games like ax-thowing and pickleball. Combined, they’re a major bet on the idea that D.C.-area residents are willing to spend time in the heart of downtown — if they have a reason to visit.

“There's still a human need, Maslow's hierarchy, to be together and to meet together,” Valero said. “Although that might not be every day anymore, there is a need in our community — and I would say very much a need in downtown D.C. — for that type of space.”