Should I Open a Business with My Bestie?

Casey’s been out of the country for 11 days, but hey who’s counting (cough, cough…. I AM!). To be perfectly honest having my partner-in-crime gone for this long has been really hard! Of course not having my best friend around to chat with or shoot 50 text messages to throughout the day makes my days far less exciting.

But not having the other half of this blog around to help field questions, comments, emails, and just the workload that happens behind-the-scenes has been even more difficult. Don’t get me wrong, I’m SOOOO excited for her because she deserves a break away to unplug from her extremely hectic schedule, but I do miss her… A LOT! (Side note: Is anyone else living vicariously through her InstaStories and posts?!)

Better Together

Having Casey absent from the workload for a couple weeks has been a friendly reminder of how lucky we are to have each other as we juggle this exciting blogging journey.  Like any business, blogging is a lot of work and being able to divide up the work load and chat about upcoming ideas/projects/concerns is far more effective with two perspectives instead of one.

Starting this blog together has been one of the best decisions we have ever made because we would have never gotten this far without one another. Plus working together every day has strengthened our friendship more than we ever realized was possible.

However, we definitely wouldn’t recommend everyone going into business with their bestie. We are evidence that it can work and be amazing, but we also believe you need to think long and hard before calling your best friend your business partner. The stakes of this decision can be super high and we don’t think any business is worth ruining your friendship over. So how do you decide if it will be a good fit or not?

Well, this brings me to one of our most frequently asked questions:

How Do I Know If I Should Go into Business with My Bestie?

Our answer is actually pretty simple. You need to focus on two components of your best friend because these two qualities will build the foundation of everything else, regardless of what business you’re interested in starting. Here’s what you need to focus on:

  1. Your Best Friend’s Values
  2. Your Best Friend’s Work Ethic (and work style)

As long as you are on the same page in these two categories, we’re confident that you are bound to be great business partners while protecting that amazing friendship along the way.

Your Best Friend’s Values

As crazy as it may sound, starting a business together is similar to getting into a marriage. And just like choosing a spouse, you have to focus on your partner’s value system because this will drive so many of the decisions you make throughout your journey. It’s impossible to know where your business venture will take you so knowing that you both have a similar value system when it comes to communication, family, money, free time, etc. will help you get on the same page when challenges or decisions pop up.

It’s impossible to know where your business venture will take you so knowing that you both have a similar value system when it comes to communication, family, money, free time, etc. will help you get on the same page when challenges or decisions pop up.

Casey and I have an extremely similar value system. From how we treat our marriages, to how much time we both spend with our families, to our political views…. we are so similar on so many important topics in our life because we value the same things. When challenging situations or big decisions pop up, we are usually both on the same page (or not very far off) because our value systems are so much alike. This has been one of the biggest blessings so far and half of the reason we have made it this far together.

Make sure you and your best friend take time to compare your value systems before diving in, especially your value when it comes to money.

Your Best Friend’s Work Ethic

The next vital component to evaluate is one another’s work ethic. Casey and I are both high-strung, Type A personalities who get stressed at the sight of anything looming on our to-do list. We both can’t stand emails unanswered in our inbox and are eager to put in as much extra time as needed to power through our to-do lists. The bottom line is that we are both workaholics, which we realize is not always healthy but it’s our reality.

This doesn’t mean you should only go into business with your bestie if he or she is a workaholic. No matter how hard you work, you should not go into business with someone who cannot match (or exceed) your efforts. If you don’t think your best friend can work harder than you can, then this is not a business relationship that will stand the test of time. You must be confident that he or she can outwork you before taking the dive. If you’re not positive, it’s not going to work out well.

We’re not saying you have to share the same strengths or have to have a similar personality to make it work. In fact, sometimes it’s great if one person is more strategic while the other is more logistical. You can each bring unique skills to the team. However, make sure your work ethic is similar…or else someone will constantly feel like they’re doing all of the work and resentment can set in.

It’s Not Always Easy, But it Can Work

If you and your bestie share similar values and work ethic, we think you two may actually be a great fit as future business partners. Make sure you really do your research in these areas though because those categories can seem pretty straight forward, but actually have a lot of depth to them.

If you are finally ready to take the dive, remember that working together isn’t going to always be easy, but it will always be worth it. And no matter how crazy life gets, don’t forget that you are best friends first and business partners next. There is no business worth more than your friendship.


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.