Thriving cities depend on the adventurous among us, who alter the urban landscape when they forge their own successful paths.

Each month, we ask an influential San Diegan: What was it like for you in the beginning?

Chad Cline

Restaurateur,  The Waterfront Bar & Grill,

How did your family come to own the Waterfront?
The Waterfront was opened in 1933. My family didn’t get involved until my great grandpa, Melvin Miller, bought it. I believe he started in bootlegging as a kid, and eventually he made his way into buying and selling bars. He purchased the Waterfront as another thing to flip. It wasn’t really special until my grandma, Nancy Nichols, purchased it and made it that way.

What struggles did your family face owning Waterfront?
When my grandma bought the bar, it was in bad shape. That was late 70s/early 80s. Little Italy was mostly a bunch of warehouses. There were a few restaurants, but the area was in decline.

My Grandma loved it though. She liked the characters and enjoyed getting to know everyone. The Italian fisherman loved coming in and helping cook. The Waterfront became a real community hub and my Grandma’s personality was at the center of it, making sure everyone felt welcomed. She was, and still is, an amazing woman that took a real crappy dive bar in a bad area and transformed into a special neighborhood place.

What was the riskiest business move you ever made?
When the area started to blow up, and Little Italy started to change, my cousin and I made changes that appealed to a younger audience — going for a place where a 21 year old could hang out with an 81 year old.

We wanted to attract new customers by improving the outdated, but grandma didn’t want to make regulars mad with little changes to their home away from home. We were sure that the regulars would still come around. That didn’t always work. Sometimes we would make changes that the regulars would still hate but we tried our best to keep them happy while welcoming new faces.

The first spot I did outside of Waterfront was High Dive. It was a total experiment that taught me a lot. At that time I knew that I wanted to expand, but didn’t really know what I was doing. My cousin Rocky started Eastbound Bar & Grill shortly after, and experienced a very similar learning process. Since, we’ve opened Werewolf, Club Marina and Banzai together.  I also opened Harbor House, and he opened the The Hills. I think they’re all risky.

Every single time we open something we put our entire heart into it. We really try hard to provide something special. When you put that kind of energy into it, failure becomes very scary. The bar business isn’t easy. We’re basically in the business of making everyone happy, and everyone knows what they say about that.

If you could change the past, is there anything in your career you’d do differently?
I would have invested into Eastbound and The Hills with my cousin. Other than that I feel I’ve learned from anything that’s gone wrong.

Could you ever go back to a “normal job” working for someone else?
Sometimes I dream about working for someone else. I think the grass is always greener on the other side.

What personality traits must a successful business owner possess?
I’m not sure that there’s a list of traits. I do feel that a person who goes into business for themselves needs to always try and see the positive. I think the main thing is going for it. Be an idiot and jump off the cliff. Make yourself grow wings or die trying. Just make sure you give it everything you got.

In the beginning, if you could have had a glimpse into where your work is today, what three words describe how you might have felt?
One word: relieved. I wouldn’t feel anything else.