The role of connections in business and entrepreneurship
Connected By: A New Series by Rachel Schwartzmann
Behind every success story is a series of big breaks, mentorship, guidance, and happy accidents.
Thrive, or dive
“If trusting each other is not possible, don’t take yourself through that hell—it’s not worth the train wreck!”
In 2019, Erin Bury was the managing director of a busy creative agency in Toronto, Canada. She had been at the company since the summer of 2013, but began to realize that she wanted to do something different.
At that time, her husband, Kevin Oulds, was the CEO of Willful, the end-of-life planning startup he founded in 2017. After some discussion, the pair decided that the best move Erin could make was to join her husband’s company. “Originally the idea was I would help on a part-time basis while I took some time off to figure out what was next,” Erin tells Supermaker. “But clearly that didn't happen.”
After leaving her agency in March, Erin was named Willful’s new CEO, replacing her husband, who became the company’s head of business development. Almost overnight, Erin went from being an advisor and early investor in her husband’s company to being the head of it—coincidentally, just a few months after the couple got married. “Not only did he have to get used to working with his wife every day but he also had to get used to a whole new role,” Erin says. “It was definitely a transition.”
Starting any new venture comes with challenges—and bringing your significant other into the mix can certainly complicate things. Whether it’s figuring out how to draw boundaries between the personal and the professional or planning what would happen to the business if the marriage or partnership were to end, there is a lot to consider before making the shift from life partner to business partner. Yet, collaborating with your significant other can also allow for a level of trust and collaboration seldom offered by other working relationships. Given the complexity of this working arrangement, an important question arises: what should you keep in mind before going into business with your significant other?
For Esi Kagale Agyeman Gillo and Peter Markeeo Gillo, working together evolved naturally. Soon after they first started dating, the pair found themselves collaborating on various creative endeavors, including a sustainable Ugandan cotton clothing line. Today, the two run DIFFvelopment, a career services nonprofit that offers Black students culturally specific opportunities in the entrepreneurial space. Collaboration has been a theme throughout their relationship, and the pair says the success of their ventures has depended on their communication.
Over the years, the couple has had constant discussions around how their work impacts their marriage. “We had many [conversations] about how it was affecting our relationship and how to remain cognizant of the need to keep the dynamic healthy and positive,” says Esi, admitting that as their work grew and evolved, so, too, did the potential for tensions around working style and shared goals. This was especially true when it came to money.
According to Esi, Peter was more focused on returns whereas her primary motivation had never been financial gain. “It took awhile for me to understand the difference between what drove him versus what drove me,” Esi says. “Once I did, however, the next step was figuring out a way to bring our desires and talents together.”
Though their struggles were different, Kevin and Erin dealt with their own share of challenges while learning to work together in a professional setting. The couple had already worked together before Erin officially joined the company, but the pair had to face the reality of what it meant to officially be in business together, and how their marriage could impact the future of the company.
“You have to ask some tough questions [like] what happens if we don’t like working together—is it that I leave? Or we both leave?” Erin said, admitting that it was sometimes difficult to imagine how they would feel if that were to happen. Still, she said that having these discussions were important and necessary. “You have to think about these things. It’s naive to think that nothing will happen just because you hope it won’t.”
Peter and Esi have had similar discussions, and though they don’t have an official exit plan in place, the two feel that the nonprofit they have built already exists outside of them. “We both believe that what we created is bigger than us and will stand the test of time,” Peter says. “Our work is for the people we serve,” Esi adds. “With or without our relationship, we will have to carry out the work or find others who can carry [it] out when we no longer can.”
Justine Clay is a business coach for creative entrepreneurs and, when it comes to working with a significant other, she says there are many things to consider. Justine recommends beginning by getting clear about the motivations behind the collaboration, specifically whether it’s an emotional impulse or a rational, business investment.
Once a couple has decided that they’re in it for the right reasons, Justine recommends developing strategies to ensure a healthy working relationship. This could include setting boundaries and establishing clear channels of communication around feelings and expectations. Justine notes that each person comes to a venture from a different place, not just in terms of skill sets but also lived experience and risk tolerance. “Running a business can be uncomfortable,” Justine says. “And some people are able to tolerate feelings of insecurity better than others.”
Expectations can also differ when it comes to long-term planning, and so Justine recommends exploring where each partner envisions the future of the business—whether one year, three years, or five years down the road. While some individuals might hope to scale and sell a venture, others might prefer to build a family business that stays a more manageable size. “Different people will bring different ideas to what a business actually means for them,” she says.
According to Justine, the most important thing a couple must do before going into business together is to develop a contingency plan in the event of a breakup or divorce. The thought is unpleasant, Justine admits, though she says the discussion is a necessary one. She encourages couples to put everything out on the table ahead of time—and, ideally, to finalize it in contract form. “If it works on paper it has a chance of working out in real life,” she says.
These conversations can be tough, but once they are had they can open up space for a collaboration to flourish. Though both couples have had their share of challenges, working together has ultimately proved to be a worthwhile experience. “It’s easier in some ways to build a company with your spouse,” Erin says, adding that the pair has been able to accept opportunities, such as moving to another city for a long-term accelerator program, without having to run the idea past two or more sets of families. “We didn’t have to ask permission, we only had to look at each other to know this was a great opportunity.”
For Esi and Peter, the best part of working together has been getting to know one another’s unique skills, and understanding how one partner’s strengths complement the other. “Having a partner to bounce ideas off of over time, you realize what you are great at [and can] really push forward what you created together,” Peter says.
This said, Peter admits that working with your partner certainly isn’t always smooth sailing. “When shit [hits] the proverbial fan it is easy to point fingers and be really nasty,” Peter says. The key to finding a balance? Trusting one another and letting the mission drive the work. “If trusting each other is not possible, don’t take yourself through that hell—it’s not worth the train wreck!”