What would you be doing if you weren’t doing what you’re doing now?

It’s my favorite question to ask in interviews and one I try to answer all the time. My list of fantasy alternative jobs is expansive: glass tile artist, chocolatier, dog trainer and/or rescuer, florist, mail delivery person (in San Diego only, no snow deliveries), professor, gun-toting federal agent, personal trainer/yogi and curator.

My most recurring fantasy is to be the mom in a mom-and-pop shop. We’ll have a little store and do just enough business to live comfortably. Mostly, I just want to laugh and chitchat all day. A bookstore would be perfect for chitchat. Like the one Meg Ryan’s character owns in the 1998 movie “You’ve Got Mail” before Tom Hanks and his big-box bookstore put her out of business.

As Ryan’s character learned, you’ve got to work very hard to compete with big companies and you may still lose. I thought it might be instructive to speak to some of San Diego’s proverbial moms and pops to find out how to start a business with your spouse, make a living and stay married in the real world.

Keep Your Day Job

Deciding to start a dream family business can be a huge risk to the family finances, which is why experts and couples-in-the-know recommend that at least one spouse keep their day job.

When Marc and Darlynne Menkin started Where You Want To Be Tours in 2003, they both had full-time jobs in completely unrelated fields. They started with small bike and walking tours, and worked up to large corporate groups until, eventually, in the past year it has become a full-time job for them both. They even have a crew of 18 part-time guides to help them with extra large groups – like the 65-person tour they led in early May.

“The advice that I would have would be to take baby steps,” says Marc. “But sometimes when people take baby steps they’re sort of dreaming, but not planning. So you’ve got to take baby steps, but actually take them.”

Entrepreneur Bruce Judson, author of “Go It Alone” and a senior faculty fellow at Yale School of Management, advocates not quitting your day job and finding a business that can be done at night and on weekends by leveraging online and automated resources.

If that sounds exhausting, answer his question: “How much do you want to change your life?


If you don’t know what ABC means, maybe going into business isn’t for you. ABC: A-Always, B-Be, C-Closing. It’s what Alex Baldwin’s jerky character tells his fleet of failing salesmen in the 1992 movie “GlenGarry Glen Ross.” Whether you open a restaurant or a bookstore or sell homemade soap out of your garage, you need actual business skills. If you can’t market your business and sell your goods and services, it doesn’t matter if you make the most intriguing artisan chocolates outside of Belgium.

“You haven’t got a business until someone you don’t know came to you through someone you don’t know and spent money with you,” says Judson.

When Martin and Cindy Blair decided to open Kansas City Barbeque near Seaport Village neither of them had any restaurant experience. But their business has thrived for 23 years and they recently opened a second restaurant – Carlsbad’s Ocean House – with another couple.

Martin was previously in property management, which came in handy during lease negotiations. Cindy’s architectural experience working with government proved useful at permit time. They hired a good barbecue chef to do the cooking. They also opened the restaurant on the cheap by buying used kitchen supplies at auctions and kept six months expenses in the bank. The Blairs believe many restaurateurs overspend at first.

“Always stay close to the cash,” says Cindy, who has maintained a full-time job as a commercial architect the entire time. “We bought nothing new for 15 years,” says Martin.

A Thin Line Between Love and Work

I’m one of those people who would love to work with my spouse all day and cling to him all night. We love to be together, all the time. But you don’t have to like that much one-on-one time to succeed in business together, you just need to follow a few guidelines and answer the essential question: Can we work together, really?

“It’s better than I thought,” says Monica Haber, who owns The Treatery ice cream and candy store with her husband in Chula Vista’s Otay Ranch master-planned community. “I was afraid working with Allan would bring a lot of conflict between us. On the contrary, we’re a good team.”

The key is to know each other’s strengths and weaknesses, and to divvy up responsibilities accordingly. At The Treatery, Allan focuses on management and products, soaking up the Food Network and reading trade journals for creative menu ideas like chocolate-dipped frozen bananas. Monica reigns in customer service. She knows regular customers by name and what they order.

While Marc Menkin handles sales and finances at the family tour company, his wife Darlynne is “command central” when it comes to running the tour guide crew, public speaking and project oversight. They do most tours together.

Where You Want To Be offers 10 walking, bike and double-decker bus tours and designs custom scavenger huts around San Diego for parties and corporate groups. The focus is on spirited explorations of “Hidden San Diego.” It’s not about listening to staid history lessons over a megaphone, but wandering around with a small group of friends and realizing in the end that you are, in fact, exactly where you want to be.

“We play off each really well. It’s very playful,” says Darlynne. “We like to tease each other. As much as possible, we do together.”

“She’s the color commentary, I’m historical,” says Marc. “We tell people the tours are part historical and part hysterical.”

Both couples say a spirit of adventure and a willingness to support that spirit in each other enabled them to start and develop their businesses. Having clear responsibilities keeps them from stepping on each other’s toes.

Talk Is a Cheap Business Tool

“A business partnership is a relationship whether you’re married or not,” says Allan Haber. “You need to have communication.”

Bruce Judson the entrepreneur and author couldn’t agree more. He says once couples have decided they want to work together, they must ask more questions.

– Who will make which decisions? Will the spouse in charge of marketing make all the marketing decisions or discuss them with the other spouse first. Judson says couples must be careful not to get hamstrung by too much collaboration.

– Will you let clients know that you’re married? If so, will the information be part of your marketing, or just one of those things you don’t keep a secret.

– Will you talk about business at home or on vacation? Some spouses have strict rules on this subject, while others see business and home as part of one long beautiful day together.

“The top thing is that we’re a husband and wife,” says Darlynne Menkin. “We’ve got to remember that. We’ve got to have fun and we’ve got to go on vacations.”

Catherine MacRae Hockmuth is a freelance writer in Chula Vista. “Married & Mortgaged” runs every other Thursday. You can send a letter to the editor here.

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