A person in a pirate costume stands in front of a Victorian-style house.
A person in a pirate costume stands in front of the "Pink Painted Lady" at Alamo Square Park for the launch of Ahoy, an AI startup. Photo by Brandon Pho.

At 8 a.m. Wednesday, one of the only signs that something was happening at the “Pink Painted Lady,” one of the seven famous private residences on Alamo Square’s “Postcard Row,” was the actor in a pirate costume assuming a drunken stance by the front steps. 

At the top of the stairs, an usher in a black suit checked Partiful reservations, then lifted the velvet rope. Behind it: a launch party for Ahoy, a startup celebrating the rollout of its AI sales work product by transforming the ground floor of the home into a swashbuckling fantasia.

“Anytime you see a company launch, you spend $60,000 on a launch video,” said Jana Iris, a key investor in Ahoy with TQ Ventures. “Instead we thought: let’s do something for the community.” 

For an industry critics fear has come to plunder San Francisco’s real estate, the company’s pirate-themed shindig — overtaking one of the Painted Ladies — may have been a smidge on the nose. 

On the other hand, the event was free and open-invite, and it offered a rare chance to see inside the otherwise restricted historic landmark.

A pirate skeleton in front of a red curtain with a sign reading "BEWARE! ENTER." People stand in the dimly lit background.
A pirate skeleton greets guests of Ahoy’s launch party. Photo by Brandon Pho.

Leah Culver, a former senior engineer at Twitter and now Airbnb, bought the Pink Lady in 2020 for $3.55 million, well above the asking price. In 2022, Culver announced she was putting the home back up for sale.

The three-story house had been neglected for decades before Culver bought it, and the extent of the work that needed to be done was overwhelming

Now, Culver says, it’s no longer on the market as she decides on long-term plans.

“In the meantime, we’re going to continue to explore opportunities for public access,” Culver told Mission Local. “Not just tech folks hoping to do events.”

Iris, a good friend of Culver’s, persuaded her to let Ahoy turn the open rooms into a smuggler’s cove, decking its storied walls with buccaneer mannequins, a skeleton in a brig, and other seafaring frills.

People gather inside a dimly lit room with tropical decor, some standing near a display of bottles; a palm leaf and a window with a tree outside are visible, reminiscent of the relaxed ambiance found in the Painted Ladies district.
Guests mingle inside the “Pink Painted Lady” for Ahoy’s agentic meeting product launch. Photo by Brandon Pho.

Dozens of people attended at different parts of the day. Conversation ranged from networking requests to musings about their employers (several guests refused to share who they worked for).

“I’ve been here for 20 years through a few different booms and busts,” Iris said, her months-old puppy Dolores at her feet.

“San Francisco has always been a Gold Rush, transient city. There are always going to be people who come to make their money and leave. And then there are people like us: I plan to be in S.F. for the rest of my life, and I want to create events like this, fostering appreciation for the city’s art and music and culture, forever.”

Woman sits on steps holding a dog in her lap, smiling. The steps are decorated with four skull ornaments and a dog statue. House number "714" is visible above the door.
Jana Iris, a longtime tech startup fixture and Ahoy investor with TQ Ventures, sits with her dog Dolores on the steps of the “Pink Painted Lady.” Photo by Brandon Pho.

For Ahoy’s co-founders, Monique Eisenach and Kevin Bluett, the party was a way to differentiate themselves as “not like any other startup.” The two previously spent a combined 17 years at customer service software company HubSpot, they said, and wanted to get people’s attention in a way that felt community-oriented. 

“It’s important to preserve — and continue to celebrate — our history,” Eisenach said. “But also,” she added, “build new things.” 

Perhaps unintentionally, they tapped into an understanding shared by some city preservationists.

“Historic buildings that survive are those that get used and are active,” said Woody LaBounty, president and CEO of SF Heritage, a nonprofit dedicated to preserving the city’s historic character. “And getting more people inside to appreciate them is a good thing.” 

At this, the launch succeeded. Judith Hengeveld, a website designer, and her husband Nick, a developer at GitHub, trekked from San Carlos simply to see the house.

“I don’t exactly know what Ahoy does,” Judith said. “But my guess is it has something to do with AI.”

Brandon Pho covers tech and power in San Francisco.

He has reported on communities up and down California since 2018.

Right before joining Mission Local, he sparked a California lawsuit against the federal government after obtaining and publishing the blueprints for a secret Bay Area ICE facility.

He likes the TV series ‘Columbo’ and lives under the panoptic surveillance of his two cats near Mission Dolores.

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4 Comments

  1. A pirate is the perfect symbol for ai. This pair was in customer service but they can’t read a room.

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  2. These out-to-launch parties are so 2022! Just get a flip phone and look up info at your local library and life will get slower, less chaotic and reasonable. And maybe we can return to $2 croissants.

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  3. The Painted Ladies are so overrated! Walk around the adjoining neighborhoods and you will see a variety of much more interesting abodes.
    Yes, Alamo Park is cool (and has bathrooms!) but folks, let’s appreciate other streets/neighborhoods/architecture.

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  4. You can do something for the community by taking your startup and your slop generator and your data centers and shoving all of it way way deep inside and then leaving never to return. Thanks!

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