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Media Girlfriends co-owners (from left) Garvia Bailey, Hannah Sung and Nana aba Duncan were friends before they went into business together.Dave Chan/The Globe and Mail

Coming up with a killer idea and then building a business from the ground up alongside people you care about can be an extremely rewarding experience. Just ask Garvia Bailey, co-founder of Media Girlfriends, a Toronto-based podcast production company.

“When we talk about our goals and we talk about what we want to accomplish as a business, we know our motivations a little deeper than just what you might find in a [typical] working environment,” Ms. Bailey says of her relationship with founder Nana aba Duncan and fellow co-founder Hannah Sung.

“Our motivations and what we do as a business [are] intrinsically linked to who we are as people, as individuals,” she adds.

Best friends Shelby Weaver and Abby Albino met while they were both working for the Toronto Raptors; together, they founded Makeway, a sneaker boutique “for women, by women” located in Toronto. They both agree that there’s something special about their business relationship.

“One of the best parts of building a business with a friend is having established trust in them,” says Ms. Weaver. “Having known each other for almost a decade, we’ve built trust throughout the friendship and know that we have one another’s back at all times.”

However, no relationship – or business – can flourish without overcoming challenges along the way.

Similar to a marriage

Sunny Sabbini calls herself a couple’s counsellor for co-founders and business partners. Based in San Francisco, she has 20 years of experience as a transformation coach and marriage and family therapist.

Ms. Sabbini says that business partnerships can be quite similar to marriages in that there are similar intentions to “create something together, leverage each other’s strengths and be of mutual support.”

But there are also unique challenges to creating a business with a friend.

“There are different parts of ourselves that only appear when in a work environment,” Ms. Sabbini says. “Oftentimes friends are surprised when the relationship becomes strained upon working together or when facing a crisis.”

Ms. Albino says that in operating Makeway with Ms. Weaver, openness and respect help make any tough conversations easier.

“We are very honest and transparent with each other,” Ms. Albino says. “We rarely disagree on something but when we do, we talk it out respectfully and move forward.”

Ms. Sung and Ms. Bailey say preparing beforehand has been key to avoiding potential work-related conflicts.

“We talked about our divorce before we got married,” Ms. Sung says with a laugh.

The first thing the team did once they decided to get into a business relationship was bring in a lawyer and create a shareholders’ agreement. They also had hard conversations about what would happen if one of them wanted to kick someone out of the company, and who would be responsible for what if one of the team were to leave.

“I feel like that [preparation] is such a safety net for us to have laid that down early in the process,” Ms. Bailey says. “I think that it’s the kind of thing that can save a friendship.”

Getting to the root of the problem

Ms. Sabbini says that some of the most common issues business partners come to her with are communication issues, stalemates and avoiding each other. These are typically just manifestations of an underlying problem, she notes.

Her first step is to help business partners improve communication so they can get to the root of the real problem.

“I always start by establishing a framework for understanding and defusing emotional reactivity,” Ms. Sabbini says. (That’s the impulsive overreaction that can happen when emotions take over during a conflict.) “There is no constructive communication that can happen when we are reactive,” she says.

“Once we have the big picture, each partner identifies their priority concerns and we find the overlap between them. [Then we can] address the issues in one-on-one sessions, while setting up ways to continue the work between sessions.”

Working with friends can also be challenging as partners learn more about each other and potential working quirks or shortcomings, says Ms. Sabbini. It’s a scenario that can be especially high-stakes when there’s money, staff and the survival of your friendship on the line.

A strong personal relationship doesn’t necessarily mean strong professional compatibility, she adds, though in most cases damaged business partnerships can be repaired.

‘Landing in a safe place’

As for Makeway and Media Girlfriends, the future looks bright for both the businesses and the friendships that preceded them.

Ms. Bailey says working with friends continues to offer many advantages.

“It makes it easy to bring your whole self to the work [when] you know that your whole self is landing in a safe place because you’re dealing with people who know you, who really know you,” she says.

“We always say, even on our hardest days, they’re better than our best days [in] the other jobs we had.”

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