Starting a Business With a Friend: Important Dos and Don’ts

If you and your friend are both entrepreneurs (or aspiring entrepreneurs), brainstorming new business ideas are probably standard issue. And when you hit upon a really good business idea, you’ll want to take that entrepreneurial spirit off your friend’s living room couch and into the boardroom. That could be a great decision.

Be aware, though, that there’s a right way to go about starting a business with a friend—and a not-so-right way, too.

To be fair, starting a business isn’t ever an easy endeavor. And we get the thought that partnering up with your favorite person would mitigate some of that stress, or at least make it more fun. That can certainly be the case.

But starting a business with a friend means that your relationship changes. During working hours, you’ll need to interact with each other a little more formally than you would if you were just hanging at home, especially if you’re co-helming a team of employees.

You’ll also need to make sure that your close personal connection doesn’t result in sloppy business practices. Emotions can run high when you’re going into a business with a friend—or anyone for that matter—but you also need to keep those emotions in check to run your business professionally. Obviously, that’s harder to do if your best friend is sitting in the next office, or if it’s your best friend who’s triggering those emotions.

That said, starting a business with a friend can absolutely be done—you just need to keep a few best practices in mind. We asked a few entrepreneurs who’ve successfully mixed business and friendship to share their advice on what to do, and what not to do, when you’re starting a business with a friend.

First, we’ll cover the right stuff. If you’re thinking of starting a business with a friend, keep these tips in your back pocket:

You probably know from your personal relationships that open communication is crucial. The same principle applies to business partnerships.

But if you go into business with a friend, it can be easy to take that principle for granted: You know each other inside and out. It’s fine to go about your business under the assumption that you’re on the same page. Right?

The truth is, silence breeds confusion. And in a business setting, that confusion can result in devastating losses.

Josh Rubin, owner and CEO of Post Modern Marketing, understands the importance of maintaining clear channels of communication between you and your friends-turned-business partners.

“In a previous version of my company, I employed two of my best friends,” Rubin says. “I trusted my friends, so I took their word for it when they said that they were staying on top of their roles. But, pretty soon, an IRS audit uncovered that my friend was paying themselves more money than we’d agreed upon, for hours they weren’t working. As a result, the relationship, and the business, were damaged beyond repair. So, my one big tip for anyone starting a business with friends is: Don’t start a business on promises alone.”

Even though you innately trust your friends, you still need to communicate clearly about everything. Especially the difficult subjects.

This tip follows naturally from the first: Clearly define your job titles and responsibilities at the outset of your venture. It’ll ensure that your organization runs smoothly, and it minimizes the risk of confusion, and even power struggles, as your business scales.

Bill Widmer, cofounder of The Wandering RV, learned the importance of job titles quickly after starting his business. While traveling in an RV for six months together, Widmer and his fiancée, Kayla, launched a website to keep their friends and family updated on their travels. Soon, the venture became popular, and their business was born.

Widmer says:
Once we hit the first page for one of our articles, that’s when we realized we might have a real business opportunity on our hands. We continued to create search-friendly content and build links to it, and now the site sees over 100,000 unique visitors per month.

But at the beginning, Kayla and I didn’t have any kind of defined roles. We were just ‘co-owners.’ She did a bunch of stuff and so did I. It worked for a while, but it caused a lot of stress between us. Now, she writes most of the content, and I’m the editor and marketer. She handles social media, I handle email. If something goes wrong, we know who’s ‘fault’ it was, so that person can take responsibility and fix it.

Of all the varied advice our expert entrepreneurs gave us, writing a business plan was the common denominator.

Laying out a strategic map for the next 1 to 5 years of your business’s life is crucial for any kind of venture. But when you start a business with your best friend—and you’ve had the necessary, preliminary conversations ensuring that you’re on the same page about this thing—you might think the strength of your word and a formal business plan are mutually exclusive.

According to our experts—they’re not! In fact, it might be a good idea to hire a business lawyer to help you draw up your plan.

One of those experts, Adam Cole, successfully co-directs Grant Park Academy of the Arts alongside his good friend. One of the keys to that success, Cole says, was getting everything down in writing. “We hired a lawyer and drafted an operating agreement,” Cole says. “It took some time, and the discussions could get a little uncomfortable as we contemplated what could go wrong between us or to our business. But now we have a plan to fall back on in case our relationship or our business changes.”

Clearly, creating an exit strategy is just as important as creating a business plan is. The failure of a business is tough, and it can wreak all kinds of havoc, not least of which is a potential rift between the founders. A formal exit plan corrals that chaos into order. And it ensures, as much as possible, that the failed business doesn’t ruin your friendship, as well.

After his previous experience, Josh Rubin firmly believes in the importance of a written agreement and an exit plan, both legally binding and otherwise.

“Get a lawyer, make sure everything is buttoned up, and have separation and buyout clauses that protect both parties,” Rubin suggests. “Within that agreement, write out everyone’s job description, goals, and expectations, just like you would for any other employee. Then, hold each other accountable to following that business plan. It’s the only way you’ll succeed as business partners and friends.”

It may seem pretty natural to think about going into business with a friend, but there are a few pitfalls you’ll need to be mindful of avoiding. Here’s what not to do if you want to keep your business—and your friendship—afloat.

Of course, you and your best friend get along really well—you wouldn’t be best friends if you didn’t! But compatibility doesn’t always translate once you start running an office together.

This all ties back to that foundational do: Clear communication. Commit to that transparency even before you start your business. That way, you’ll make sure you’re starting that business with the right partner.

“If you think divorces are messy, business separations are equally devastating,” says Bret Bonnet, who co-founded Quality Logo Products® along with his best friend, Michael Wegner, when they were still in college.

And although these separations do happen, you of course don’t want it to happen to your business. You’ll need to do your due diligence on your partners beforehand—even if that partner is your college roommate/emergency contact/child’s godparent. “Make sure you know everything and anything about who you’re considering going into business with,” Bonnet advises. “Like in a marriage, the skeletons in their closet eventually become yours.”

So, how can you tell if you and your friend will make great business partners? Here’s a tip from Bill Widmer: “If you and your friend or partner can’t communicate productively—or if every disagreement turns into a massive fight or argument—that person probably isn’t a good fit as a business partner.”

In that case, you might want to leave the healthy debates at home, and seek a compatible business partner outside your inner circle.

You and your friend have shared values, tastes, and experiences. But that doesn’t necessarily mean your values, tastes, and work habits will align on your business goals. For example, if you believe in starting a nonprofit organization, and your best friend dreams of one day buying her own yacht, that bodes poorly for a cohesive, functional venture.

Obviously, both parties need to be in total agreement about what they want their business to achieve. On top of that, Alex Moen, cofounder of Match Made Coffee, suggests that both parties need to be in alignment about prioritizing that business, too.

“I’ve experienced issues when friends didn’t fully understand that starting a business requires a huge commitment,” Moen says. “They ended up leaving the business, and putting the remaining team in a precarious situation.

So, everyone needs to be clear on the required time commitment for both the short term and the long haul. From the outset, have a clear discussion about how many hours per week everyone can commit to, what your long-term milestones are, and how much sweat equity everyone needs to contribute to hit those goals.”

Running a business with your best friend is a logistical and emotional balancing act. The core tenet of separating your personal and business finances is obviously applicable to your business, but you’ll need to clearly delineate your professional relationship from your personal relationship, too.

Says Moen, “Remember that whatever happens to your business has nothing to do with your friendship, and vice versa.” As the adage goes, business isn’t personal. It should be no different in your business, but it’s tougher when you’re already emotionally entangled with your business partner.

To help you disentangle the personal and professional, keep in mind that the office is the office, and home is home. Your conversations with your best friend-slash-business partner should stay on their respective sides of that line: Use text and personal emails for personal matters, and your business emails for business matters. And, whenever possible, take your deeply personal conversations to the bar around the corner when you’re done for the day.

True, being your best friend’s business partner fundamentally changes your relationship. But prioritizing your business doesn’t mean scrubbing out your emotional connection entirely.

“Unless you don’t mind losing your friend,” Widmer advises, “always put the friendship first. Go into this thing with an exit plan if everything falls apart, so you both know the other person has your back and the loss won’t ruin your friendship.”

The truth is, businesses fail. But if you give them the time and attention they need to thrive, friendships can last forever. We know it’s sappy, but you know it’s true! So, put some time on your schedules to step out of the office—or, even better, take a weekend together—and talk about anything other than business (if you can!).

A few of the experts we interviewed made the comparison between business partnerships and marriage. It might seem like a pretty dramatic analogy, but if you think about it, it’s appropriate. Both relationships require mutual respect, trust, and—in case we haven’t underscored this one enough—open and frequent communication.

Together, you and your business partner will experience thrilling wins and, potentially, pretty devastating lows. You’ll manage the fun stuff together, like building a product you believe in, sharing your product with others, and generating a loyal customer base. And you’ll manage the not-always-fun stuff, too. Like your finances.

In fact, there’s a good chance that you’ll spend more time with your business partner than you do with your actual significant other. So, you have to be certain that you and your potential business partner can sustain a functional, courteous, and productive working relationship over the long-term. That may or may not be the case with your best friend.

As you likely know, you don’t go ahead and marry someone just because you two have a good time together. Same thing goes for business partnerships: Agreeing on your favorite band doesn’t necessarily mean you’ll agree on how to run a joint business venture. Then again, maybe it does. You just need to be really honest with each other first.

So, before you start applying for small business loans, run review this experts list of the dos and don’ts of starting a business with your best friend one more time:

• DO communicate often, especially about the difficult things.

• DO make sure your roles and responsibilities are clearly defined from the outset.

• DO write a business plan, and an exit plan, either with or without legal counsel.

• DON’T assume that you have the same vision for your business, or the same level of commitment.

• As much as possible, DON’T intermingle your personal lives and your business lives.

• DON’T forget that you were friends before you were business partners, and DO continue to nurture your friendship outside the office.

If that all sounds doable for both you and your best friend, then you might be ready to embark on your entrepreneurial venture together. And, when done the right way, it can be incredibly rewarding to helm a business venture with your partner-in-crime.

That’s certainly the case for Devi Jagadesan and Karmen Auble. The best friends are cofounders of Sparkle, which they started after each of them experienced sexual assault. They developed the bracelet to heighten awareness of the epidemic, but also to remind people of their happiness, passion, and self-worth.