In June 2008, Lookout Bar & Grill owners Tina DelSanto and Katherine Loblein appeared before the Belfast City Council asking for permission to sell beer in a public park during the annual Celtic Celebration, then in its second year.

They were young, both well under 30 years old. And their request was a big one. The municipal code of ordinances prohibited alcohol consumption in the city’s parks.

To make matters more complicated, the city manager had written an opinion against making an exception for the Celtic Celebration, and several councilors were strongly opposed to the idea of alcohol in the parks under any circumstances.

But DelSanto, who did most of the talking, had done her homework. Every point brought forward by the Council she met with a well-researched response, until there was nothing left but the letter of the law. And even that she methodically picked apart.

Looking back on the meeting, DelSanto said the request probably went through on the subjective rationale, advanced by the Council, that a Celtic festival ought to have beer. But that was the self-effacing DelSanto speaking, the one who has been an amicable hostess to the city’s late night bar crowd for nearly six years.

As it turned out, she and Loblein just knew what they were doing. The beer tent at the Celtic Celebration went off without incident — for all the trouble it caused, the provisional beer garden erected on Belfast Common might as well have been an open-air pretzel parlor — and the Lookout has since gone on to become a mainstay of the growing festival, which returned to Belfast for a fifth time last weekend.

Owing much to the kind of perseverance that got them a beer tent on Belfast Common, DelSanto and Loblein have been busy in the interim. Both have branched out from their waterfront roots, independently pursuing new businesses. As of this summer, they appear poised to take a big step up in local the business scene.

In June, Loblein opened her namesake boutique Katwalk on Upper Main Street, while DelSanto and her boyfriend and business partner Anthony Jacovino are celebrating the first anniversary of Delvino’s Grill & Pasta House, and working feverishly to open a new Mexican and Caribbean restaurant, La Vida, in August.

Speaking on July 7, DelSanto and Loblein talked about business and their decisions to open new businesses after nearly six years of operating the Lookout. It was morning and the women showed the kind of easy rapport of friends who have weathered the best and worst of times.

“I think you get the bug,” said DelSanto.

“Tina definitely has the bug,” said Loblein.

“I love restaurants,” said DelSanto, “and Katherine loves fashion.”

“Not really,” Loblein said. “I love to shop, and this [Katwalk] keeps me from going bankrupt every week.”

DelSanto, who is originally from Portland, got the business bug early. In seventh grade, she was involved in a bake sale to raise money for an eighth grade trip. Afterward, she was called to the principal’s office, thinking all the while that she was in trouble. Instead, the principal said he could envision her succeeding in business. She was an entrepreneur, he said.

“I was in seventh grade. I had no idea what it was,” she said. “He told me to go look it up.”

There were other school sales and minor acts of entrepreneurship. At age 21, DelSanto and three friends bought an apartment building. It was an “epic failure” she said, but she learned a lot. Later she went to culinary school, before ending up in Belfast.

Loblein’s introduction to business was less of a calling. She grew up in Belfast, and her mother had a shop with some similarities to Katwalk in Camden. There was “some college,” she said, but she didn’t finish. When DelSanto approached her about buying the Lookout, she was in school for massage therapy.

“I always thought maybe I’d open a shop one day,” she said. “It was really Tina who made me realize I could do stuff like this.”

DelSanto and Loblein had each been working at the Lookout for around a year when the bar went under. As a business, it may have been loosely managed, they speculated, but there were outside circumstances too. MBNA and its big tipping employees had recently departed, and the city was in an economic lull.

But DelSanto, who had the idea to buy the bar, saw it as an opportunity.

In conversation, Loblein, jokingly describes herself as having been “roped” or “dragged” into the business by her friend.

From their minimal past experience, they believed they could run the bar, but the banks — who, in the opinion of DelSanto and Loblein, saw women, 23 and 25 years old, respectively, as a couple of girlfriends who thought owning a bar would be fun — weren’t convinced.

There was a lot of lecturing from loan officers about how running a business was hard. But DelSanto and Loblein already knew the unglamorous side of running a bar. They knew it wasn’t going to be a party; it was going to be cleaning up after the party.

Their persistence wasn’t enough, but Loblein’s father agreed to cosign the loan and they bought the bar.

Initially, DelSanto was there so much that she slept on an air mattress in the upstairs above the bar.

“People would come up the back stairs looking for the late-night party,” she said.

Around that time, she met Anthony Jacovino, a soft-spoken microbiologist-turned-carpenter, and the two quickly became a couple. Jacovino did carpentry work in the bar. They moved to nicer digs.

The history of the Lookout over the next five years could probably fill a book with colorful anecdotes, but in practical terms, the business was a springboard for what was to come next.

In 2009, DelSanto and Jacovino opened the Belfast Bake Shop and Deli. A year later, they opened Delvino’s Grill & Pasta House, coining the name from a portmanteau of their own last names. The business was “50/50,” DelSanto said.

By the end of the summer, however, they were overworked, and something had to give. As DelSanto saw it, the Lookout was their “jumping off point” and Delvino’s was “special.” So the Bake Shop closed, though DelSanto said it might reopen in the future.

DelSanto described La Vida as being like Delvino’s, in the sense that the menu is based around a regional cuisine — Italian in the case of Delvino’s; Mexican and Caribbean at La Vida — but there are other influences, and creative deviations.

On July 18, DelSanto was finalizing the menu for La Vida, where an appetizer called “Shark Bites,” made from shark meat, appeared nearby pickled french fries, jerk chicken, and bar standards like wings and jalapeño poppers.

DelSanto said much of the menu will be fresh foods — from the fruit used for tropical drinks to the salsa and the chicken, broiled and pulled on site. The restaurant is also looking for local producers.

“If there are farmers, fishermen and cattle raisers and they’re legal to sell, we’ll buy it,” she said.

Loblein ventured out on her own for the first time this spring with help from her boyfriend John Gibbs, a sergeant with the Belfast Police Department, who she met more or less on the job three years ago.

Katwalk, a play on Loblein’s first name, has some of the trappings of a boutique (a small space, fashion-forward attitude, expensive jeans), and enough Maine-made crafts — including several lots of pottery from Monroe Saltworks, which went out of business earlier this year — to make the store genuinely eclectic.

But the main idea, she said was to offer affordable, fashions for young women.

To this end, she has tops starting at around $15, dresses in the $30 range, earrings, jewelry and other accessories, much of which is made by Loblein, family members or friends.

“If you want to go out on Friday night, you can get a pair of $6 earrings and a $20 top,” she said. “Instead of running to Bangor, you can run into my shop and get something fun.”

DelSanto chimed in. “We had had girls coming in for years complaining about what they couldn’t get, and wanted,” she said.

“And what I couldn’t get, and wanted,” said Loblein.

Despite moving on to new businesses, and lodging some complaints about the grind of managing drunk people — DelSanto said she has yet to sleep a week of nights without being woken by a call from the bar’s security service, or some other prompt to an incident unfolding at the bar — both said their first business has been excellent training for the others.

“If you can open a bar, you can pretty much open any business,” said Loblein.

DelSanto said the major hassle with a bar is getting all the proper permitting, in part because there is no central clearinghouse for information on what kinds of permits a business needs.

“There should be a ‘How to Open a Business for Dummies’ book,” said Loblein.

DelSanto thought about it.

“But then you’d have all these dummies opening businesses that are failures,” she said.

Asked independently if they plan to keep the bar, neither hesitated for a moment.

“It’s my baby,” DelSanto said. “I’m never giving it up.”

Loblein seemed surprised by the idea that she would leave the bar behind. There was clearly a fondness, but her answer was also pragmatic. “It’s the only business that’s making money,” she said.

The Lookout Bar & Grill is located at 37B Front Street in Belfast. Katwalk is at 104 Main Street. Delvino’s is at 52 Main Street.

La Vida, located at 132 High Street is holding a grand opening the weekend of August 6-8, with food and drinks served until midnight, and other surprises planned.

“We’re looking for a mariachi band,” said DelSanto, “But we’re in Maine.”