A buoyant 36-year-old environmental lawyer from San Francisco might not sound like someone interested in buying a bar a little rough around the edges in a town known for its skepticism of outsiders. But Leila Monroe is poised to finalize the purchase of Smiley’s Schooner Saloon, one of the oldest continuously running bars in the state, at the outset of 2015. (The deal is currently in escrow, though she has already set up a suggestion box to help her hit the ground running in January.)
Ms. Monroe, whose father also owned a bar in a small town, has some changes in mind, but she also wants to maintain what she loves about Smiley’s, particularly the music. “I’m trying to make it a smooth transition. We have some plans, but we want to do what’s working: more music, and improve the stage and sound system without making it louder or obnoxious to community members,” she said.
An L.L.C. she formed with family members will purchase the property, while a separate one that includes her business partner, Ashley Huck, will buy the business.
The bar is in need of some physical upgrades, she said.
Smiley’s was built in 1851 and managed to stay in business through the 1906 earthquake and prohibition, when most of its windows were painted black. (A barbershop could be seen through an unpainted one.) The last major renovations to the building were undertaken in the 1980s, so there is a significant amount of deferred maintenance, Ms. Monroe said. She aims to fix up the six hotel rooms, too.
Don Deane, the bar’s current owner and the former publisher of the Coastal Post, agrees. “She has some really good plans to restore the things that need to be restored physically,” he said, noting that the roof and foundation need work. “That will preserve and propel Smiley’s into the future, and that’s a grand and good thing.”
Bringing in more customers during daytime hours is also part of the plan, likely by bolstering food offerings (that’s currently limited by the use permit) and broadening the selection of non-alcoholic drinks.
“Having more non-alcoholic beverages will be key, because the place outside is really sweet but you don’t necessarily want to drink a beer at 11 a.m. on a Wednesday. Maybe you want a kombucha or iced tea,” she said. (Technically the fermented tea actually has a small amount of alcohol in it). Better afternoon traffic will make the business more financially sound. “We need to do a lot to increase sales,” she said.
Ms. Monroe’s father owned a bar in the small town of Julian, in the Cuyamaca Mountains, in Southern California. The bar, Bailey BBQ, had an atmosphere reminiscent of Smiley’s. “There was lots of live music and barbecue, a wood pit barbecue,” she said.
Though Smiley’s featured live music before Mr. Deane took over from Robert Glen in 1990, he said his ownership brought a new era of regular events—bands, open mic night, karaoke—on a regular basis, as well as a true sound system. But he said it has been a challenge to support that level of entertainment in a rural town.
Ms. Monroe, a Bay Area native, spent years in D.C. before returning about a decade ago; at the time, she wrote a business plan for a different bar she considered buying. But she tabled the idea, deciding instead to focus on legal work; she most recently spent about six years as an ocean conservation attorney for the Natural Resources Defense Council.
She left the job and spent some time considering new directions. She recently started an organization, called Project AMPLIFI, which connects musicians to nonprofits to help them raise money; one of the key goals of the group is finding musicians with a genuine interest in the cause. The connections she’s made will likely help her as she seeks to lure fresh bands to Bolinas. (She’s also planning to launch a boutique law firm focusing on environmental law in January.)
The fortuitous timing of Ms. Monroe’s career shift coincided with Smiley’s once again going up for sale, as Mr. Deane had taken it off the market during the
recession.
She started visiting Bolinas after she moved to San Francisco 10 years ago, surfing with friends when she could, and she has stayed at the hotel with her husband and in-laws. (She remarked that Bolinas was next to state marine protected areas, another of the many things that attracted the ocean lawyer.) She said a friend of hers emailed her the listing and told her she should buy the bar.
So she did.
B.G. Bates, a Bolinas realtor, said some prospective buyers who contacted her had ideas of turning Smiley’s into a private getaway. (She had endless calls after lowering the advertised price at a dollar under $1.5 million, she said.) Eventually Mr. Deane whittled it down to three prospective buyers. They each made pitches, but Ms. Monroe stood above the rest.
“When I showed her the property, she said, ‘Oh, this is the exactly the kind of business my family has been looking for,’” Ms. Bates said.
Ms. Bates also noted that Ms. Monroe is adding to the number of women who seem to be running Bolinas: the volunteer fire department, the utility district and the grocery store are all run by women.
She’ll remain in San Francisco for the time being, but she dreams that eventually she and her husband, who lives in Santa Cruz, could find a way to migrate to West Marin.
Mr. Deane, part of the fabric of Bolinas since he moved there in 1971, plans to focus on a campground he owns in the Sierras, where he will soon live.
But he will not disappear from town. “I’m gonna miss Smiley’s. I loved every minute of being the trustee, the owner, of Smiley’s, and I fully intended to come back down here at least once a month because I have kids in town and friends,” he said.
Ms. Monroe will host a meet and greet at Smileys this Sunday, Dec. 7 at 2 p.m.
This article was amended on Dec. 6 to reflect the correct location of Ms. Monroe’s father’s bar.