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Lessons from an Entrepreneur: Married to the Boss

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married to the boss

It isn’t easy working with your spouse. Let’s start with that. I have been asked a million times, “how do you two work together?”. “I would kill my ‘spouse’ if I had to work with him/her”!

I’ve killed him multiple times, in my head.

From the time we met, we talked about going into business together, and while it’s been a roller coaster ride, our relationship is closer than ever. I’m not saying it’s easy, and it certainly isn’t for everyone.

Neither of us has a business degree. I certainly feel like we have both “earned” an MBA through running our businesses over the past 20 years. And yet there is so much more to learn. There is no doubt we could have saved ourselves a headache (and a penny), a thousand times if we had gotten a business degree prior to starting the business.

Our past and our personalities came into play when the responsibilities of running our business started falling into place. He’s an extrovert; I’m not. I like details; he would rather pull out a fingernail than worry about the details. I like numbers; he likes making the big sale.

When we started Web Teks we were each working 12+ hours a day right next to each other. It was fun and exciting as we were establishing … everything. When we started growing, our time together was not constant, and usually not alone.

We used to joke that we had board meetings in bed. And while that’s funny, we don’t do that anymore and I don’t recommend it as a regular practice. We have tried to limit our evening talk about business to a minimum. It’s not possible to just turn it off.

That inability to “turn it off” is what makes it the most difficult. If one of us is worried about something, the other does too. And while that is sometimes a good thing, sometimes it isn’t. My role has always been the accounting, human resources, administration part of the business and his role was always sales. Until we hired a CTO, we would both run production.

So Tom was always traveling and establishing relationships with potential customers and partners. The extrovert and one who was always motivating the team to learn more and do more and be more. And in some ways, the fun one. I, on the other hand, worked with the lawyers, bankers, HR consultants, and anyone else who I needed to help me run the business.

A friend once said, “If you want to take over a city, call Tom; and then bring in Dyanne to run it”.

He and I are now working with two different companies (both ours), in different cities, and sometimes we don’t talk to each other all day. That was prior to COVID. We are currently both working from home and feel fortunate to have space to move around and separate from each other.

If you have an opportunity to work with your spouse here are a few things that worked for us.

Separate responsibilities. We are responsible for different areas of the business. This keeps us out of each other’s hair and when we do cross over, we default to the “owner” of that role.

Keep it at the office. We have tried to set some parameters around when we talk about business. Not so much structured times, but on most nights we focus on NOT talking about business. It can be a real challenge to separate business from home when you live together, but it’s worth the effort.

Be respectful of each other. It’s important to show respect for and be respectful of each other, at all times. It’s important for your employees to feel at ease and really, not even remember that you are married. Your marriage should not be “a thing” in the office.

Make it fun. When possible, I like to travel with Tom and if we can make it work, we will add on a day or two of free time to pretend we are on vacation. There were always plenty of events for us to attend together as well, from formals to cook-outs. We have been to the governor’s mansion and a presidential inauguration. And even when these events are work-related, they can be a lot of fun.

As I sit here and write “tips” I can think of many times we didn’t have fun or weren’t respectful of each other. It’s not always fun and games. Again, I am not an expert on how it should be done, only what we have done.

At the end of the day, we are both proud of our accomplishments and proud of each other. We created our careers. We have done it with each other and our family in mind. Neither of us came from money, so when we took that leap of faith, it was in each other. And surprisingly, we are both still alive, and still in love.

Do YOU work with a loved one, spouse, relative, or friend? How does it work for you?

Until next time,


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