The Proper Care and Feeding of an Entrepreneur


Do you spend your Friday evenings watching Shark Tank with a partner who is constantly getting irked at the equity offer of the potential investee? Do conversations with your partner inevitably lead to some brand-new scheme about how to make more passive income? Does your partner own a Gary Vee inspired baseball cap with the term #hustle emblazoned across the front?

If that checklist rings true for, then I hate to break it to you, but you are in love with an entrepreneur!

As challenging as it may be to be in a relationship with an entrepreneur, you might keep finding yourself being drawn to them. I sure am! I grew up in an art-based, entrepreneurial household, and now, in my adult life, I love a full-bred, self-made, renaissance man.

It’s essential to the health of any relationship to keep wondering how to show up and be a better partner. In an entrepreneurial partnership, that question is even more pertinent, as their proper care and feeding is a full-time job in itself.

Entrepreneurs come in all shapes and sizes, but at their core, they have the same goal in common…a positive cashflow. I can still hear the echoes of my dad, “Happiness is a positive cashflow” in response to, “Hey Dennis, how are ya?”

So, how does one be the best partner to this special breed? I actually sat down with my partner and interviewed him to get the direct line into his thinking, to understand what support looks and feel likes to him. In that, here are the Top 5 Tips to being in relationship to/with an entrepreneur.

1.      Don’t take rescheduling personally: For an entrepreneur, fluidity is key. Most days look like one large chess game, where they are trying to make multiple things work simultaneously. This means that the best laid plans usually get tossed out early in the day. You may have a date planned, but by 6pm, they could be in the midst of putting out another critical fire. It is understandable to feel frustrated, as I’m sure they do as well. So, the best way around this is to ask them for more quality time, without resenting them for having to ask. It’s not that they are avoiding you, or that you are not a priority. It’s that for them, everything points back to “positive cashflow” and you must be able to understand and respect that.

2.      Whatever they are talking about is the most important thing to them at the time: With so many items to manage, they have multiple tabs open in their brains and they enjoy talking out their ideas. So, the thing that is top of mind is the most important thing, at any given moment. This can work in your favor, when YOU are top of mind, but can also leave you feeling like you’re basking in the sun or living in the shadows, as there isn’t much in between when it comes to attention. In those moments, just listen as they talk through some processes. At times, it can be helpful to ask if they just need to vent, or if they would like to engage in conversation.

3.      Patience is elusive so model that behavior and help them with it: To the entrepreneur, no one is ever operating fast enough for them. They are usually 12 steps ahead of the pack, and waiting is not their strong suit. That impatience may end up being taken out on you, the person they are closest to. When it comes to patience, you must exercise it in spades, and model for them how a few deep breaths can effectively slow them down. Offer them some grace and understanding that their frustration has very little to do with you, so try not to take it personally (easier said than done.)

4.     Acknowledge the bad days, but don’t dwell: Entrepreneurs are not super human, but want to be viewed as such. No one is immune to bad days, but the worst thing you can do is take a rough moment and make it the focus of attention. It is necessary to find the balance of acknowledging that something has been challenging, and then using positive language to help propel them forward. Be a compassionate cheerleader.  For example: “I can see where that’s hard to not have your web designer on the same page as you, but you will figure out a way to make it work. You always do. You got this!”

5.      Gratitude is currency: Any entrepreneur has had their ego crushed at some point or another, so it’s no wonder that gratitude goes along way. Find the small things to be grateful for each day and aim to understand how they are all contributing to a larger picture. Take time out to text or share in person something that you appreciate about your partner. Positive reinforcement helps to beget more of the same ideal behavior in the future.

Most entrepreneurs have a very specific vision they are working towards, and long story short, they need undying support to get there. That’s why, as their partner, it is crucial to check in with yourself and see if you can really be along for the ride without resentment. Sacrifice is a part of the entrepreneur’s relationship, and balance is at a premium. It is likely that the two of you have very different relationships with time, and priorities, and so over-communicating about sacred space and time just for the two of you will help mitigate any future loss of quality connection. But, as mentioned before, when you hold the attention of one, you will feel like you’re on top of the world, and that feeling is hard to beat.