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Our sibling rivalry has helped us to build a nearly 8-figure business


“If I had to work with my brother, I would shoot him!”

I’ve heard similar sentiments many times from people who are amazed that I can work in the same building with my brother, let alone run a multi-million-dollar business with him.

And on some days, I can really relate.

Yet our differences often end up being the reason we accomplish so much. We’ve been working together on and off throughout our lives, starting with a car-washing business in our neighborhood when we were kids.

While we always work well together when we want to achieve a financial goal, there’s no question that we have been uber-competitive for decades. We have fought over everything from who gets the last Girl Scouts Thin-Mint cookie to how big our next office space needs be. Our quarreling has helped us to become better negotiators, to learn how to compromise and to work harder to improve our skills.

If you’ve ever thought about working with a family member, you might be surprised to find that the very things that drive you crazy about your sibling are also the things that might help your business succeed. Here are some of the ways to make a sibling relationship work in growing your business.

Pursue your separate strengths

Even as kids, our separate skill sets worked in our favor. Dave would knock on the potential customer’s door and offer to wash their car for three bucks, and I’d stand in the driveway with a smile, a bucket, and a sponge, ready to implement if they said yes.

Thirty-five years later, we operate the same way, with Dave handling sales, management, and contracting while I oversee marketing, SEO, and human resources. We divide our business duties along those lines, and we rarely stray from them.

By purposely focusing on tasks that play to your natural strengths, you’ll avoid a lot of conflicts that would create unnecessary drama. Trusting each to accomplish the individual tasks that you are most well-suited for will propel your business forward.

Read more: 11 ways to help your kids become wealthier, according to an author who spent years studying millionaires

Capitalize on being natural allies

Danielle and Dave.
Courtesy of Danielle Roberts

Dr. Claire Hughes, the author of “Social Understanding and Social Lives,” said that despite natural sibling rivalry among children, siblings are our natural allies who are often on our same wavelength.

This has never been truer for us than when we decided to take our business online in an industry where Medicare insurance has been sold across the kitchen table for decades. While you can earn a living doing this, it’s not a very scalable business model.

We theorized that as baby boomers began to turn 65, they would be ready to buy these products online. Industry old-timers laughed at this, but we stuck together, believing it would work, and committing to it until it did.

You can achieve a lot because you and your sibling are already in each other’s corner. Being allies gives you heightened perspective on everything from your competition to your banking decisions because there is always someone you trust to bounce your ideas off and share your opinions with.

Take advantage of the common ground

There are certain things that you and your sibling might have in common due to growing up in the same family. For us, there’s a similar work ethic and approach to finances. We both love to earn money via personal effort, and we are both savers who believe in reinvesting profits back into the agency and helping our employees get ahead.

These are pretty important in a business partnership, so before you team up with anyone, make sure that you and that person have the same views on how many hours you should put in each week and when you’ll take money home versus when you’ll invest it back into the business. Different perspectives on these two things can quickly kill a struggling new partnership.

Make a list of your other common traits that could work in your favor and exploit them.

Get plenty of away-from-each-other time

Except for larger family get-togethers, we rarely spend any time together outside of work — and we couldn’t be happier about it. After all, we spend a good 50+ hours a week together and that can get old for almost anyone.

If you plan to start a business with someone in your family, find the line of separation and be sure to give yourself mental breaks for one another. Have your own friends and your own hobbies and your own lives outside of work.

When Monday rolls around, you’ll look forward to seeing your relative and be ready to discuss new ideas, work on your business plan or make big decisions. It’s one of our most productive times of the week, and we capitalize on it.

Read more: I’m a recruiter who’s placed hundreds of senior professionals. Here are 5 things hiring managers know that job seekers don’t.

Be brutally honest

Being siblings will allow you a level of transparency that you might not have if you started your business with someone else. You can state your frank opinions without worrying about what your business partner will think. You don’t have to mince words.

It’s amazing how much this helps to get to the bottom of any problem or project quickly. We can vehemently disagree on something and an hour later we are asking each other what’s for lunch.

I doubt that either of us could accomplish that level of acceptance if our business partner wasn’t our sibling. At the end of the day, even if we disagree, he’s still my brother.

Courtesy of Danielle Roberts

Celebrate your wins together

There’s something really special about achieving a milestone with someone who has known you all your life. You remember the smallest ancient things, like teaming up on Mom to get her to agree to let you buy a trampoline if you paid for it with your own money. Then you remember the really big things, like the day your first six-figure deposit hit your company checking account.

You may be celebrating far bigger achievements these days, but you never forget where you came from and you come to respect the synergy that got you here.

Going into business with a sibling is not an option for everyone, but if you’ve ever considered it, you might look at the differences between you and ask yourself: Could those differences be your strengths in a business partnership? You might just find that the things that exhaust you about your sibling are the exact things your company needs to thrive.


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