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Working With a Sibling Can Be Crazy, But Also Crazy Wonderful

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There are some very famous sister pairs who work together. Ones that come to mind right away include Mary-Kate and Ashley Olsen, Venus and Serena Williams, Jessica and Ashlee Simpson, all seven of the Kardashians, etc. They’ve all talked about how magical it is to work with their sisters and how every day is like heaven because they spend it with their best friends. But let’s get real. Those women are making millions. If I was making as much money as Kim Kardashian, I would skip and hold hands with my sister all day.

But in reality, can siblings actually work well together? Especially in the trenches of a small business or startup? There are many siblings that get along great, but I bet they don’t work together! Frankly, my sister and I, who are both grown women, only stopped hitting each other in public like two years ago. How the hell would we work together?

According to the Family Firm Institute, a research group in Boston, only 30 percent of family-owned businesses make it to the second generation, 10 percent to the third generation, and 3 percent to the fourth. This doesn’t sound promising for sib partners, but actually Wayne Rivers, president of Family Business Institute in Raleigh, N.C., an advisory firm for family-owned companies, told Businessweek, “Ten years ago, 25 percent of family businesses were partnerships. I would say [the number] is substantially larger today.”

In honor of National Sibling Day, we decided to explore the age old topic of, how do siblings work together?

A huge problem really seems to be the blurred lines between the business and family relationships. Mary Maher, Co-Founder of the booming Chicago bakery Cake Girls that she started with her sister Brenda Maher is quite familiar with this concept:

“You can depend on your sister like no one you’ve ever worked with. I know that she’s not going anywhere and that we will both do whatever it takes to make our business successful. I can trust her work ethic, because I happen to have the same one. On the flip side, she’s right when she says that the lines can get blurred and things can get personal. That’s not usually something that would happen between co-workers if they weren’t siblings.”

There are definitely pros to being comfortable enough to tell your business partner exactly what you are thinking. With a non-sibling partner or co-worker you have more boundaries up. But maybe boundaries are a good thing?

Mary told us, “B&M—Although we are close, we often disagree. Communication is always the hardest part of the relationship. We know we have said things we didn’t clearly communicate which seemed offensive or hurtful. We have just recently started finishing a conversation with a recap so we both leave knowing exactly what our opinions are and what goals we have.”

But then again, in an intense environment like a startup or small business where every second counts, being extremely close with a sibling can be great. “I know this for sure, Mary always has my back. I never have to wonder if she is working hard enough or cares or wants the best for our business. Plus, Mary is one of the best cake decorators in the United States. Throughout our business I have been able to see magic happen,” Brenda said.

Plus, hopefully, unlike a business partner, your sibling won’t surprise you with their personality. Mary said, “M—The best part is that I think we have different strengths and weaknesses. I’m more artistic, but can be scatter brained and Brenda is willing to take more risks than I am. She pushes me to believe in our talent and always makes me believe that we’re “the bomb”, even if I don’t deep down.”

Plus, siblings can connect on a whole different level than just good friends and business partners. That’s right: You don’t have to be a twin or a witch to know what your sibling is thinking. This hilarious clip from Happy Endings perfectly demonstrates how weird sisterly intuition can be.

Sitting in car with someone for most of your childhood allows you to see the inner psyches of people in a way no one else can capture. Mary said she found this to be true when the sisters competed on the Food Network Challenge. “It was so stressful and fast paced that we just fell into a zone of knowing what the other person needed and how to collectively get the job done without further discussion. I don’t think I could’ve had that type of experience with another person.”

And, of course, who else would you want to go through strange and embarassing situations with? Brenda recalls one of their first press photoshoots when they were made to look like chihuahuas and drag queens. “We were both shocked, but just went for it. It was actually one of the best times we had promoting our business. The staff was great and we learned to roll with it.”

If you’re gonna roll through it, who better to do it with than your sister or brother?

Have you ever worked with a sibling? What was it like? Tell us in the comments!


Entrepreneurship #Personal Relationships #Startup #Family Lifestyle News
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I attended college with my older brother for two years and I can not see us working at the same business together or partnering together to run our own business. Our relationship is decent because we have the same interests, views about most issues, but our personalities are night and day. I am more outspoken and competitive, wear as my brother is shy (he has trouble looking you in the eye type of shy)and leads by example. My brother and I have never worked together, but when we play basketball together, he is reluctant to let me come play. And when we do play, we are bickering at one another the whole game because I just missed a contested lay-up or he decided to settle for an outside jumper. Our teammates don't mind it though, because it does add to making the games competitive and fun. I think the difference between my brother and I is that we appreciate and love one another, but we do not want our professional (and athletic) careers to overlap and intertwine with one another...because we will become too hostile and competitive!


My sister and I have just started working together, creating a blog called The Garden Apt. ( She's made a huge career change within the last year, and I am in the process of making one. We aren't sure where we are going with everything right now, the beauty of being young and with few attachments, but when I see my future career, it is definitely with her in some sort of creative enterprise. As mentioned in the article, the beauty of working with your sister is that not only is she your sister and co-worker, but there's a sixth sense of communication and understanding with siblings that no one else has!

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