How to Successfully Start a Business With Your Best Friend

Working closely with your best friend - let alone starting a business together - is often seen as risky. But Future Fragment’s founders, Deon Taljaard and Stuart Jacobs, didn’t let their 23-year friendship stop them from successfully co-founding Future Fragment. As best friends and business partners, they’ve learned a lot about how to beat the myth and confidently walk the tightrope of “professional versus personal.”

Deon and Stuart used to work together as software developers. Throughout their friendship, they shared a dream of one day starting a successful IT business together - and now, two years since Future Fragment was born, they reflect on the concerns, risks and sacrifices they were faced with when they first started. They knew they were risking their friendship, and that each would have to sacrifice something to get there. They questioned if they have what it takes to succeed as friends and as business partners, but despite those insecurities they went for it anyway. Deon says they “trusted their friendship enough to augment the partnership, rather than complicate it."

Benefits of co-founding with a friend

With the success they’ve seen so far, Deon and Stuart’s long-standing friendship means that they knew each other incredibly well, which, in their experience, offers a range of benefits:

• Knowing how their partner feels: Deon and Stuart can pick up on nuances in facial expression, body language, or tone of voice. They know what triggers certain emotions in the other person, which means they can address things long before they escalate into bigger problems.
• Knowing how their partner thinks: They've spent so much time together in a variety of situations, that they have a good idea of how the other person understands the world. This lets them anticipate each other's responses, for example, and optimise any discussion by preparing responses to questions before they even chat. As Deon puts it: “Just being aware of those things, and then engaging in a business relationship, enables you to harness experiences and feelings as friends to drive your business relationship even further.”
• Not feeling offended, or threatened: They've been through enough to know that what the other person says isn't ever personal, and that they share a common dream. They don’t get offended, and know that they’re working towards the same ideal, which enables them to respond meaningfully in discussions and debates, rather than emotionally.
• Trusting each other’s priorities and honesty: Deon and Stuart have years of trust behind them. They’ve learned what they prioritise, how they do it, and why. If Deon takes the day off, for example, Stuart knows that he isn't doing so without reason, or without the business' interests at heart. “When there was an emotionally draining day,” Deon recalls, “we’d say ‘Hey man, just take your time. Take a personal day. I've got your back for the next day or two.’ And that comes down to trust.”

How to make sure the benefits last

Dedicated "coffee-time"

It’s easy to lose yourself within your work, and not make enough time to chat about how you’re feeling. You risk bottling things up and exploding when the pressure becomes too much, which makes it hard to know if you’re lashing-out as a friend, or as a colleague.

To step out of the office as friends, rather than business partners, Deon and Stuart schedule time once a day to have coffee together. They leave their desks and use that time to chat about their day, their week, their concerns, their wins, or anything else that doesn’t otherwise feel like a “first priority" for their business relationship. Deon also says that it makes having difficult conversations a lot easier: "There isn't a build-up of emotion,” he says, “so there's nothing to hold back on. We can just air how we’re feeling in the moment, and chat about it."

Since their dynamic as a partnership is calmer, healthier, and more open, their interactions with the rest of the team are less tense and more productive.

Leisure activities outside of work

Only seeing each other at work, and only ever doing work-related things together, risks that a partnership turns sour because of little to no outside stimulation. Having something that changes pace means you can catch a break from only ever doing business together, and opens up more channels of communication than simply a boardroom or an email.

Deon and Stuart have found that gymming together over lunch suits their schedules well. They use that time to be a team in a different environment, “spotting” or encouraging each other for example. Stuart mentions that “it helps blow off steam as friends, and go back to the office as business partners again.” Being a team as friends outside of the office also strengthens how they interact as colleagues, because they invest into their relationship on a deeper level. In other words, when they need to work, they work hard, because they know that they can blow off steam together later on.

Intentionality about non-work related conversations

Always talking about work could mean that the friendship gets swallowed by the business partnership. Separating those relationships, where those lines are kept very clear, is a cornerstone that Deon and Stuart are intentional about keeping intact.

When not at work, they make a concerted effort to talk about non-work related things. If they're at a braai, or out with friends and family, they bench the "work talk" and simply enjoy their friendship. Stuart uses a visualisation to help him: “I can talk about work for hours on end, so I try to imagine a switch, and physically switch off talking about work.”

For them, making this distinction feeds into their relationship's success as a whole: The trust they share, their ability to not take things personally, their understanding of each other's thoughts and priorities, are all a result of not entangling their friendship with their work.

Stuart says their personal and business relationships have “two different experiences, backgrounds, histories… If you don’t recognise that, it’s like you can’t see the other side of that person anymore, and you lose touch.”

Matching strengths to responsibilities (and knowing when to pull back)

According to them, Deon is typically the more technically minded, and Stuart more intuitively aligned. Having different strengths and skill sets in a partnership is inevitable, but the two friends have managed to use that to their advantage: By taking on different leadership roles, they leverage what they’re better. As Deon puts it: “We’ve always been each other’s wing man. We both know when to pull back, and let the other one shine.”

For instance, if a conflict arises in Deon’s technical team, he steps back and lets Stuart act as "the other good-cop." Similarly, Stuart calls on Deon's help when he needs a more logical approach or systematic resolution. This does two things:

• Firstly, it removes the expectation that one person has to fill all the roles in the company. Deon and Stuart can shine in their strengths, and help each other out with their weaknesses.
• Secondly, they’ve both become better at what their partner was better at. Since they’ve been working together as co-founders, Stuart has picked up Deon’s logical thinking, and Deon has similarly become a lot better at understanding his intuition and how emotions feed into business.

If you can’t fight together, you won’t work together

Although Deon and Stuart have managed to stay friends and build a successful business together too, one piece of advice that Deon says is crucial, is to have at least one big fight before working together: “It will break the ice - and test it - because you've seen another side to the person and you've been able to say ‘Cool, OK, we’ve fought, and we’re still friends. But now we need to talk about this properly and sort it out.’”

This speaks to something the two friends had to bear in mind throughout their journey: They anticipated they would meet hurdles, that they would struggle with each other sometimes, and that they would fail before they win. “But the amount we grow as people throughout all of that,” Stuart says, “by far outweighs the negative. And I don’t think I would have done this as successfully alone.”

They never expected their friendship to change as much as it did, but because of the rhythms they followed, those changes didn’t throw them off course; instead, it solidified the foundation upon which they built their business, and allowed them to be great friends, and even better business partners.