The Truth about Running a Business with your BFF

Whenever we tell people that we’re business partners, we’re instantly bombarded with questions about what it’s REALLY like working with your bestie. Is there drama? Do we fight all the time? Do we have ever screaming matches that resemble those on The Real Housewives?!

Life as Business Partners

Emoji Halloween Costume Bridget & CaseyWe don’t blame others for wanting the scoop! And today we’re ready to dish. Let’s get right to our list of frequently asked questions so we can tell you what it’s really like running a business with your BFF.

Is there ever drama?

Bridget CaseyChristmas CardThis is going to come as a big disappointment for most of you, but we can honestly say that there is minimal drama around here. Seriously. We’re not sugar-coating anything. We get along really well, and have similar personalities. We work hard, don’t enjoy conflict (Bridget legit gets like hives at the thought of dealing with confrontation in any bad situation), and each have the utmost respect for one another! But to be perfectly honest, we don’t really have drama in ANY relationships in our lives so it wouldn’t make sense that we would have drama with each other. The only slight “drama” that ever arises is if we’re both stressed out or have a big deadline. But in those cases, we don’t take it out on one another, instead, we keep one another in check and put our frustrations into getting our work done.

Do you always get along?

Bridget_Casey_Chicago_Odyssey_Travel-14At the end of the day, we’re always going to be friends….first, business partners…second. And we would never want something petty to come in between our friendship. So yes, we do get along incredibly well 99.9% of the time! It helps that we have similar interests and work habits, because we enjoy doing the same kinds of things and don’t mind “burning the midnight oil” to get things done. If one of us put in way more hours and commitment than the other…then there might be some resentment. But luckily that isn’t the case with us!

We will say the only time when we’re not 100% on the same page is when one wants to push our business in a specific direction….while the other is a little hesitant. For example, I (Casey) wanted us to both get on board and learn how to use the editing software Lightroom. Bridget took a bit of convincing, because of the amount of time & work involved in learning a whole new program. But after a little nudging (that’s what besties are for, right?!), and a couple of weeks using Lightroom, we both agreed that it was the best thing we could have done for our blog.

So we will say that there are instances like that when one person is ready to move full speed ahead, and the other is hesitant and cautious. This never leads to fighting or not getting along, probably more the opposite actually… A LOT of positive reinforcement and encouragement to cheer the other one on in whatever new goal we’re striving for.

How do you divide tasks?

bridget-casey-computer-bedroomAnother great question! We both do projects, take photos, write posts, and deal with emails & social media. But there are certain tasks we enjoy splitting up, so our strengths can shine a bit more.05-Casey-working-at-desk-officeCasey:

I’d say out of the 2 of us, I’m definitely the more “logistical” gal. How are we going to get things done? How can we make a to-do list to get our task completed? I like to make a gameplan and figure out how we can execute it most effectively.

Casey-bed-laptopI also do a majority of the proofreading (so if you see a typo…it’s my bad!), and I also edit our videos (because that’s what I do for my day job anyways!). I have a bit of a hand in the business/financial side of things too. Because my husband Finn is our CFO, I get together with him a lot to go over numbers and keep our receipts and invoices in check. (More on how we do our blog finances in this post)Arizona_camera_bridget-001Bridget: 

She’s totally right, Casey is DEFINITELY the logistic/business brain of the two of us and I’m SO lucky to have her…. especially her proofreading. I think your eyeballs would probably hate me if she wasn’t proofreading my posts.

As much as I enjoy writing a to-do list and chatting about the business side of things, I would say my strengths are on the creative side. I take care of all of the mood boards (how we make ours in this post), graphics, and design-heavy tasks. Like Casey mentioned we both photograph our own projects, but if we’re together shooting something, I am behind the camera and the one editing the photos. I love learning more about photography and trying to get better at it since starting the blog. I also brainstorm new creative ideas or initiatives (like blog week!) and then Casey’s logistical mind takes over and helps us make these ideas a reality.

Do you recommend everyone blogs with a buddy?

Bridget-Casey-SkylineHaving someone right there with you on this journey is ah-mazing! We can showcase 2 homes, get posts done twice as fast, and always have someone around to check the email and keep our inbox in check. Not to mention, events and blogger conferences are a heck of a lot less scary when you have your BFF glued to your side (plus, who doesn’t love an excuse to take a trip with your bestie?). And through the highs, lows, good times, and not-so-good times…there’s always someone there who totally “gets it.”!  Awesome, right?!

But, we certainly don’t think it’s for everyone. Before getting into business with a good friend or family member, we think it’s important to have an open and honest discussion about how you’re going to work together. How much time are you both willing to invest? What do you do if someone gets burned out? Having an open and honest relationship is key, and we think communicating these important questions upfront can save you a lot of heartache in the long run.

In fact, we even wrote an entire blog post on the topic. Read this before you get into business with your bestie.

How has working together affected your relationship?

bridget casey christmas cIt’s made our friendship a heck of a lot stronger! Yes, we’ve been friends since high school, but as teenagers, it was a bit surface-level (not in a bad way, but when you’re young you care about boys, clothes, and other not-so-important things). Now, we chat multiple times a day and have seen one another at our best, and at our worst. We’ve gone on lots vacations and trips together (usually just the 2 of us…#girlstrip), and we do plenty of double dates with our hubbies. In fact, we’re even all heading to Mexico for New Year’s! We feel so grateful for this journey because how much it has impacted our friendship in the best way possible.

How are you guys the same?

bridget-casey-diy-guest-room-projectWe are both very ambitious, driven, compassionate and hardworking. But we’re guessing that can be said for many business owners who are excited about what they do! We’re also both fairly outgoing, bubbly, and optimistic. We don’t enjoy negativity and always try to make the most out of every situation <—wow, we sound like “goodie two shoes” don’t we?! We promise we don’t only live in a world of sunshine and smiles all the time! We’re also both super close to our moms, and love spending time with our families.

How are you guys different?

bridget casey happy Even though we share a lot of the same personality traits, we’re incredibly different too!  Bridget wakes up super early, and enjoys being in bed at a reasonable hour. While Casey doesn’t stay up super late, she certainly likes to sleep-in every once in a while and can stay up past 10:30pm <—rebel, I know!

Casey certainly enjoys her fair share of cocktails on the weekends, while Bridget can sip the same glass of wine all night long. To go even further, Bridget would probably rather skip that wine altogether and order a chocolate milkshake instead.


Speaking of chocolate milkshakes, Casey eats super healthy and has a healthy routine for just about everything in her life (skincare, hair care, sleeping, exercise, etc.) while Bridget…. not so much.

When it comes to speaking in front of a crowd, Bridget is your go-to gal. Casey is freaked out by the idea of chatting to an audience, but she doesn’t mind being in front of a video camera! Bridget is much more creative, has gorgeous penmanship, and is incredibly crafty! Whereas Casey is logistical, pays attention to detail, and is very organized. <— Heck, I thought I was very organized until I saw Casey’s computer files… she’s an organizing machine!

bridget-casey-headshot-rookiesSo there you have it…a look behind-the-scenes at what it’s really like to work alongside your BFF. We wouldn’t change it for the world and are so grateful to go on this journey side by side as business partners!



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.