What It’s Really Like Dating an Entrepreneur


Billy and I have been dating for almost two and a half years now. When we met, I was a confused and lost senior in college who, on the outside, may have appeared as though I had it all figured out. But on the inside, was just as cloudy and confused as everyone else. Honestly, that’s how I still feel today – I’m not sure that I’ll ever be “content” with where I’m at. That could be a flaw or a quirky, positive characteristic.

Anyways… every weekend I would drive all of the way to Philly to spend the weekend with him. After I graduated, we we’re basically inseparable and moved in together shortly thereafter. It’s what I love about our relationship – we love being together but doing our own things. For example, we enjoy spending time together on a Saturday or Sunday afternoon, sitting next to each other and working on completely different things.

But, back to the story. Billy was working at a company, selling a digital marketing product that he soon realized he could build a company around. At that company, he quickly became the top selling sales rep out of 3,000 other sales reps. I think that I told this story before, but March of 2017 we were set to fly out to California, all expenses paid by his former company. During our time out there, we we’re going to enjoy a weekend of relaxation and celebration. He was supposed to get on stage, in-front of the entire company, and give a speech about his recent success and motivate the rest of his coworkers.

But something happened – he had a revelation that there was a passion inside of him that he couldn’t rest until it was fulfilled. He quit his job days before we were supposed to leave for the trip. That passion was entrepreneurship – see, if you know Billy then you know that the man’s got: tenacity, drive and relentless spirit. He is the single hardest working person that I know, and EVERY one in our lives can attest to that.

He’s grown his company by 600% in his first year in business. He’s got a team of 6 employees, an office a minute away from our apartment, and more drive and spirit than he knows what to do with.

Entrepreneurship, what a buzz word in today’s millennial society. Everyone wants to be their own boss, work for themselves, have the whole “4 Hour Work Week” mentality that Tim Ferris teaches. But that notion is far from reality, at least for us. Today, I wanted to share some insights on what it’s really like to date an entrepreneur. I want to share some relationship tips on what’s worked for us in the hopes that it may resonate or help anyone out there, whether your significant other is an entrepreneur or not.


At times, you may feel second.

It may feel as though your entrepreneurial significant other is choosing his or her business over you. But the fact of the matter is, at the end of the day… You’re most likely the driving reason for them to work so hard.

In the beginning of our relationship, when Billy and I were newly dating, I couldn’t wrap my head around the fact that we barely communicated during the day. This was an argument that we frequently had. Now, looking back on it two and a half years later, I can laugh at that! WHAT WAS I THINKING?! Seriously, I got mad because he didn’t return my text message until a few hours later? Good grief, Emily… Get it together, LOL!

I wasn’t aware that someone who’s as driven as Billy quite literally doesn’t have enough time in their day to sit and go back and forth with you through text. Instead, he’d pick up the phone and call me to give me undivided attention. Yet I’d spend that time asking him why he didn’t return my text message. JEEEEZE, makes me cringe just thinking about it! Now, I put my own phone on airplane mode because text messages, calls, social media is so distracting from the work that I’m trying to produce.

But, it’s not that your entrepreneur is putting you second… They’re actually putting you first. By focusing on growing their business, they want to be able to give you opportunities that you may not have had. If you’re in it for the long haul, the empire that you create together will withstand the test of time.

BE PATIENT. Be understanding. Trust me.

You may feel inferior.

Being around someone, anyone that’s got a killer sense of direction in their life and that’s filled with energy and purpose can be intimidating. Try having that be your significant other.

At times, you may feel inferior or that you don’t have it all figured out. You may question the direction of your own life and ask yourself why you aren’t doing more. 

Like I said in the beginning of this post, two and a half years ago I was a confused and lost senior in college. But here I was, in a relationship with the most driven, confident and tenacious person that I had (and have) ever met.

I believe in this scenario, you have two choices. Either you can let that feeling of inferiority plague you or you can let it fuel you. I chose to let it fuel me. Out of that questioning of “what the heck am I doing with my life? Why aren’t I making a bigger impact. Why can’t I take a chance on my own goals” – this very blog was born! Billy’s love and drive with his company MADE me want to love something equally as much… And I DO!

I can honestly say that if I were to have never met Billy, I don’t think that the City of Sisterly Love blog would ever have came to fruition. I’m not ashamed to admit that a man, Billy, gave me the confidence to take a leap of faith on MYSELF. His unwavering support and encouragement has helped me make so many transformative leaps in my life.


Life is unpredictable in the best way possible.

Entrepreneurs are the way they are because they live life by pushing through their fears and boundaries. That’s not to say that they don’t have fears, of course they do. But they don’t let them hinder them.

Billy (and I) are such big dreamers that we spend hours each day ideating and spitballing with each other. He’s truly taught me that limits don’t exist, the only limits that we have are the ones that we place on ourselves.

Life dating an entrepreneur is unpredictable – one second they may be riding high because they just closed a big deal or finished a project. The next, they could be experiencing stress because of a client cancelling or an deal that fell through.

The important lesson here, just like in any other relationship, is to be there for them. Be as supportive, patient and loving as you can. I love and support Billy with everything in me. That man is my best friend and I’ll stand with him through the highest of highs and lowest of lows. We’re truly the best team.


I hope that this blog post was both helpful and informative. I feel like I need to do more relationship-centered blog posts. What do you think? Let me know in the comments!



1 Comment

  1. February 6, 2019 / 7:19 pm

    I LOVED reading this post! It was SO motivating, and I love hearing the background story! So well spoken and SO inspiring! Cheers to you and Billy 🙂


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