We caught up with the brilliant and insightful Diana Kirk a few weeks ago and have shared our conversation below.

Alright, Diana thanks for taking the time to share your stories and insights with us today. One deeply underappreciated facet of entrepreneurship is the kind of crazy stuff we have to deal with as business owners. Sometimes it’s crazy positive sometimes it’s crazy negative, but crazy experiences unite entrepreneurs regardless of industry. Can you share a crazy story with our readers?

When I bought my historical bar, I didn’t expect so many people to hate the changes I made.. I thought people would want the bar cleaned up, the rats gone, the kitchen sterile. But they didn’t. They wanted me to give them free drinks and put up with their crap. But that’s not the type of person I am. On a planned Sunday, when the main bar clique was eating breakfast, I let them know that I wasn’t going to be bullied or pushed around by anybody. They left that day, after throwing barstools around, and began a campaign to ruin the bar. That campaign went all the way to a bumper sticker printed and put on trucks and cars with a horrible reference to my bar becoming great again if I was raped.

Eighteen months later, after spending a quarter million dollars on infrastructure issues with the bar such as updated electrical, plumbing, windows, the bar and building now had tenants and Airbnbs and a fully functioning kitchen. But I was exhausted. I had to getaway so I flew to the Dominican Republic for a month. I sat on the beach and wrote in my journal and wrote letters. Letters to all the people who had said awful things to me, wrote awful things about me. I never sent them but it was some sort of emotional purge. I cried drinking pina coladas and staring at the caribbean.

On the third week of that trip, I found out that Vice Magazine was going to publish an article about my bar. That the historical magazine 1859 was going to publish one as well. When I returned from that trip, Vice magazine had a lead story on their channel and people were contacting me from Seattle and Portland to write articles about the bar.

Everything had changed. At the time I was purging the rats from the bar, I was also purging a mindset that a bar must cater to its clientele to succeed. I had to change the clientele to succeed. That second year at the bar, our sales went up 20%. By five years, we’d tripled our sales.

Diana, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

Before I had children, I was a guide in Alaska, a teacher in New Orleans. I’ve traveled the world working on farms and trading stories in bars that lead to sailing the Adaman Sea or climbing mountains in Peru. I’ve always had a fluid nature when it comes to the value of work. Money hasn’t always been the goal but instead experiences.

But having children meant I needed more of an anchor with my husband. We needed to stay in one place and create memories. He worked as a geologist and I stayed home for ten years. It became a weight on our shoulders. We couldn’t breathe after time. And then the market crashed in 2008. By 2010, he’d lost his geology job. It was clear there would be no more jobs for quite some time.

So we bought a 40 foot school bus, rented out our home in Portland and moved to Mexico. It was there that the true hustler came out of me. I began trading for everything. I’d find a campground, ask the owner if they wanted a website in English for the campground. Then I’d google how to make a website. I’d trade my time for a month’s camping on the beach for our RV. I’d trade English lessons for a boat ride. Anything. My husband could fix bikes, he could build kitchens. We found a town in Baja that had been flooded. He helped rebuild while the kids played on the beach all day and rode their bikes around our campground. Talked to expats from Canada and the US who were retired college professors, engineers. We had parties and spent time with interesting people who were gutsy enough to spend their winters in Mexico.

The kids began to miss home. Miss their friends. We decided to return but I had a new plan for us. I’d thought a lot about buying a rental house while we were in Mexico. We returned from Mexico and with the help of some friends, we bought our first rental. Spent six months fixing it up with borrowed money. Eventually it was rented out. I’d realized during that project, I was really good at talking to people to make deals. I could see so clearly what contractors not to hire and which ones we would end up using over and over again. Standing in the kitchen of the third house I’d bought, my husband and I shook on it. This is what we were going to do. The market was flooded with foreclosures leaking water and molding. We were going to buy them.

And we did. For three years. We worked so hard. Until one day, I fell apart. I was exhausted. I wanted out of the hunt, I wanted out of the constand turmoil related to flipping houses. The deadlines, the fear of loosing it all. I knew the only way out was to buy a business.

I found Workers Tavern by simply canvasing a neighborhood of a four plex I’d just bought. The bar sat inside a building with seven apartments. It was derelict with cracked windows taped together, broken doors, rotting siding. It was in awful shape and on the market for sale.

I wanted the apartments and ended up with a bar that has been around for over a hundred years. For eighteen months, we worked on those apartments and the kitchen of the bar and made them both a success. The entire neighborhood has now been fixed up. Parking is now an issue after decades of neglect.

Through it all, I simply believed in myself. I had enough confidence to believe I knew I could do something. I knew a woman could do something. Often called opinionated or mouthy, my entire life, somehow, all of a sudden, that very characteristic had value. My mouthy opinionated self was exactly what we’d needed to flip houses, to buy real estate in a very male dominated world. I could walk into a hoarder house with daipers and dead rats and see where a woman would say yes, I want to buy this house. Six months later, it would have a new roof, new gutters, a new kitchen and it would sell in one day. I walked into Workers Tavern with the same confidence. If I was as woman, I’d want to sit right here and watch the world go by with a cocktail. And that’s what I did. I followed my opinions and trusted myself enough to know that if I thought something, it meant others were thinking it too.

How do you keep your team’s morale high?

My entire job as the owner of my bar is morale booster. I have a manager for the bar who keeps it running, but I take my job as owner very seriously. I check in weekly with every employee. What’s going on with their boyfriends, their cars, their housing. I find them the housing they actually have. I loan them money for their cars. I give profit bonuses and once a year, I take all of them on a trip somewhere. This year we went to New Orleans. One night, everyone dressed up in sequins and we had an amazing meal at a five star restaurant. Something some of my staff have never done in their life, let alone fly on an airplane.

I’ve found that if I take very good care of my staff, I have less turnover. I find that they’ll listen when I train them to have better sales. It’s fully their job to take care of the customers so taking care of them has become my job. Once a year I implement new policies, new foods, drinks and they’re trained and then if they want to part of the team who has fun, they follow those rules. We have very little turnover with this method. I’d rather make less money and have a stable team with years of experience.

If you have multiple revenue streams in your business, would you mind opening up about what those streams are and how they fit together?

In real estate, value is set by square foot. I came to owning a bar the same way. Every square foot should make money. We have an outside company who owns the ATM and jukebox inside the bar. We have state lottery. And two of the seven apartments, the City allowed me to make into Airbnbs. During the pandemic, the monthly rentals and the Airbnbs kept the bills paid for the entire building.

We’ve now expanded into a backyard deck and patio we’re planning to use for events in the future like all day music festivals and wedding receptions. None of which anyone is doing currently in our town. We hope to be the first.

Being the owner versus the manager has given me the time to study the town dynamics and what’s needed. If I was shopping for supplies or dealing with customers, I’d never have the time for it.

Contact Info:

• Instagram: @workerstavern
• Facebook: https://m.facebook.com/workerstavern

Image Credits
Jeff Daly credit of car in front of bar.