We had the good fortune of connecting with Crosby Roper and we’ve shared our conversation below.

Hi Crosby, what do you want your legacy to be?
I want my legacy to be that of understanding and compassion. That is what The Hole in the Wall has always been about. Since this place opened it has always been a place where, no matter who you are and where you come from, if you can sit and order a drink, carry a conversation and not act like jerk, you are welcome. There is so much divisiveness and bickering nowadays. It’s in the schools, the news, and in the government. If we took the time to actually listen to one another and understand each other’s perspectives we might actually be able to gain some ground. I view my bar as a means to do just that. I want it to be a platform where people can get to know one another behind the labels of society.

What should our readers know about your business?
My business is The Hole in the Wall in Point Loma. It’s a little dive bar. Easy to miss right off of Barnett as you’re entering Point Loma. The bar itself has been there since the 1920’s. It was historically one of San Diego’s oldest openly gay bars. It still is and we have a massive crowd on Sundays. Thursdays, Fridays, and Saturdays we get more of a mixed crowd. We have a lot of people coming from Liberty Station looking for a night cap after dinner. The Hole in the Wall wasn’t meant to be pretentious or stuffy. It’s meant to be welcoming and fun. We serve our drinks in 32 oz minipitchers and encourage guests to talk and interact with one another. When you come down the steps and into our bar it’s meant to feel like a chilled out back yard BBQ. We have caterers grilling out burgers and hotdogs (with vegetarian options) and you can smell the burgers over the open flame. We have a DJ that plays music that really captures the vibe of that particular evening. My staff are fun people who love their job and work at a fun place. Their happiness is important to me because I know that they are the ones that interact with the customer and the vibe that I want to create won’t happen if my staff hate coming to work. So they’re well being is an important part of my business. I spent 8 years as a chef before opening a bar. Kitchens are hard places. Staff our over worked, underappreciated, under paid, and regularly taken advantage of. At first I wanted to open a restaurant but I wasn’t happy with the way the kitchen staff were treated. Bars were more profitable which meant that I could use some of that profit to create and better life style for my staff and make them happier. That in turn would improve my business. Restaurants or bars cannot create a good experience for the guest if the staff are unhappy. You must succeed with them first.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
Day 1 I would take them to Dog Beach then go to Old TownHouse Restaurant in Ocen Beach to nurse the hangover that we would surely have from the night before. We would probably stay in Ocean Beach most of the day stopping by Newport Pizza to try some of the craft beer and slices. Then we would walk off the calories on Sunset Cliffs during the Sunset. We’d finish it off bar hopping from Pacific Shores, to Sunshine and Co., and then end the night at Tony’s on Newport Ave.

Day 2 we would start by snorkeling in La Jolla and end the night with a fish filled dinner at Sushi Ota in Pacific beach.

Day 3 Paddle boarding in Point Loma followed by a walk around Liberty Public Market. We would do dinner at Suppanee House of Thai followed by drinks at The Hole in the Wall

Day 4 Jet skiing in the bay followed by a beach bonfire at Fiesta Island

Day 5 A walk through Balboa Park followed by dinner at Cowboy Stay in East Village in the evening.

Day 6 Hiking Potato chip rock followed by Dinner at Juniper and Ivy

Day 7 A lazy day at Wind an Sea beach followed by tacos at Los Quatros Milpas

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
I would say that my biggest shout out would have to be my staff. Everyone tells me that the hardest thing about running a bar is finding a good staff. I feel truly blessed to have a hard working and dedicated team. They have become like family over the years and they are all super friendly, down to earth, hard working individuals. The place would not be the same without them and even though we have lost some over the years, their contribution can’t be unrecognized. Beyond that I would say my family. Particularly my mom and sister. I had a rough childhood and they never gave up on me even when most people did. I wouldn’t be where I am with out them. It encourages me knowing that I have their trust and faith.

Website: https://theholesandiego.com/
Instagram: theholeinthewallsd
Facebook: The Hole in the Wall
Yelp: The Hole in the Wall

Image Credits
Bree Steffen

Nominate Someone: ShoutoutSocal is built on recommendations and shoutouts from the community; it’s how we uncover hidden gems, so if you or someone you know deserves recognition please let us know here.