Starting a Business With Your Loved Ones

A Guide on What to Expect When Working With ‘Your People’

Last weekend I celebrated my ten year anniversary with my husband, Aaron! We started dating our senior year in high school and have been together ever since. Aaron and I have had an amazing ten years filled with lots of growth, love and partnership. I believe our relationship is rock solid because it is built on an amazing friendship. And, for exactly five of our ten years, we have been business partners for Select A Sis. In honor of our anniversary, this blog post is dedicated to the ins and outs of working with the people you know best. And, lucky for everyone out there, you get to know my man because he is featured in an up-close-and-personal interview at the end of this post!

Our company Select A Sis is comprised of some of our closest friends. My little from Gamma Phi Beta is my business development partner, Aaron’s best friend from our home town is a developer and our friend from Texas A&M serves as another developer.

Wallflower Boutique is also comprised of my besties. My [Microsoft] work wife (go check out her blog!) and our good friend from Texas A&M are my business partners.

Working on a project you care about with people you care about is one of the most rewarding, yet also one of the most challenging situations you can get yourself into.

From experience, I have learned:

-You will be talking about the business at CRAZY HOURS. I’m talking 24/7.

-Some conversations will be uncomfortable.You care about the person and the business outcome. How can things not get slightly emotional?

-You just might argue, even if you do not want to! Try to step away for a few minutes if you feel things escalating.

-You will become closer.

• You will get to know one another during stressful times. You will understand how your friends react under very stressful situations.
• You will spend time talking about very interesting subjects that require deep thought - not just the average day-to-day.
• You will make tough decisions together that will affect the future of the business.

-For better or for worse, there is no getting-to-know-you stage.

-You get to build your own team! You intimately know the strengths and weaknesses of those around you. Why not build your personal #dreamteam?

My advice on starting a business with people you know:

-Set times to talk about business and/or personal life. Be clear on the topic of conversation.

-Consider writing out ground rules about your business relationship. How do you want to treat one another? I like this article on setting Ground Rules of a Team.

-Set up the ownership structure and how to make a final decision if a vote is split when you start the business: do not wait until a tough situation arises.

-Discuss job responsibilities and set clear expectations for one another.

-Be open to discussion. Read the book Crucial Conversations. It is a game changer.

Q&A with Aaron

What do you like about working with friends/loved ones? What don’t you like about working with friends/loved ones?

I think the best part about working with friends and loved ones is the strength that the prior relationship brings to the table. Building an intimate relationship with a friend or a loved one is hard work for both parties, and a lot of that hard work is reflected in your day-to-day interactions. It seems like the stereotypical business partnership with a friend often ends in strife (take Zuckerberg and Saverin, for example). However, a true friendship is a partnership: adding a working relationship is certainly a new dynamic, but the transition is easy, and the rewards are great, if you build upon the strength of your previous relationship.

As is often the case, the best facet of something is often the worst facet. The fat and sugar are the best, and worst, parts of ice cream. If not for the fat and sugar, it would not taste amazing; if not for the fat and sugar, it would not make you gain weight! The same goes for working with friends and loved ones. The prior relationship, while a huge boon, can often cause some strife. Often, you will find that you mix the two (i.e., your personal and working relationship) to unfortunate ends. In my case with Chelsey, the two of us will often, for better or worse, make a statement that we know the other will find particularly annoying. We know how to push each other’s buttons, so it is not uncommon to use those buttons when trying to convince each other of our positions in business discussions.

Would you recommend starting a business with people you know?

How often do people start businesses with people they do not know? I recommend against that, personally. If you plan on starting a pyramid scheme, then maybe it will work out OK?

What advice do you have for those who are thinking about starting a business with people they are close to?

Keeping your personal relationship and working relationship separate is ridiculous and impossible. Rather than keep them strictly separate, try to separate them in your head. Chelsey and I will often switch between personal and business topics randomly over the course of a day, or dinner. However, when the conversation moves from one to the other, we attempt to move beyond the residual feelings of the previous conversation. For example, if we are arguing about a business decision and decide to table that decision, then we typically leave any animosity generated by the business discussion behind as we move to discussing weekend activities, etc.

Starting a business with those you know should command deep consideration. But, as with anything that is difficult, the result is worth it.

Talk soon. XO,

Chelsey