9 Tested Secrets To Dating A Serial Entrepreneur

by | Aug 16, 2021 | Relationships

Dating me is rough. You have to deal with my ups and downs as well as handle the challenges of driving progress in multiple ventures. Sometimes there’s a lot of demands and extremely stressful moments. Not very romantic, eh? Being the significant other of an entrepreneur means there’s a lot of sacrifice involved along with the benefits. I have empathy for what my fiancée has endured on this journey with me and she’s been wonderful as a partner.  So what does it look like to be a significant other to an entrepreneur?

I’m excited to let my amazing fiancée, Sarah, share her side of the story.

What comes to mind when you think of dating someone who owns their own business—or several—manages a staff of employees and rolls with the movers and shakers of your city?

Glamour? Expensive cars? Dinner parties? Travel?  You’re not alone, if so. Most of my friends have been assuming these things about my life since I started my relationship with my own dazzling entrepreneur, Mike Zeller.

The truth is that while the above lifestyle perks are not necessarily false, they come with some hard-to-foresee nuances you should definitely know about if you’re in a relationship with or thinking about being in relationship with one of these irresistibly ambitious human beings.

To be totally fair, I must say that I was more than unusually prepared for the lifestyle of an entrepreneur because my dad has been one for more than twenty years.

Growing up, our family life was filled with unpredictability, fun adventures, hard work and a little spark of risk.

One of my earliest memories was at the age of seven, sitting on my parents’ bedroom floor folding invoices and stuffing them in envelopes for my dad’s commercial lighting customers.

Little did I know that almost twenty years later I’d be in a relationship with a very similar breed of person.

Obviously, many other factors will contribute to your own personal experience with dating an entrepreneur, but here are 9 of the most important things I’ve learned about being in relationship with my very own enchanting entrepreneur.

#1 They’re Reliably Late

I’m not sure if it’s the fact that they’ve got a conference call on their ear, a group text message going out, messaging their team on Slack in a frenzy, all while balancing books and binders and paperwork and mail, but something about an entrepreneur’s ability to balance chaos makes for their appearance at social gatherings to be reliably late.

And it doesn’t end there, because when they do show up, they manage to balance the emotions of everyone who would have been annoyed at their tardiness with a charming smile, a question like, “How is your new baby?” and copious hugs and handshakes.

I can rely on Michael’s lateness. It usually runs about 15-20 minutes late consistently, with the rare half-a-hour-late appearance. I’ve figured out lots of secrets to get him places on time when punctuality is essential—I can’t talk about them here obviously. But the main point is to be understanding and kind to your partner when they’re running late, again.

I will never forget this one time when Michael came to pick me up and he was late by about thirty minutes. A volcanic torrent of words was just about to burst from my mouth when I saw from across the room that he was bringing me chocolate. And that was the end of that tongue-lashing. You won’t be able to comprehend the plethora of crazy details your entrepreneur is balancing until you are one. But rely on their loving hearts and their good intentions and you’ll save yourself lots of anxiety.

#2 They Need Time to Zone In

This means no interruptions, something I happen to be terrific at. When Michael asks for his ‘alone time,’ his ‘zone-in time,’ his ‘work time,’ he’s asking for time to focus on nothing but his tasks at hand.

While I never intend to be distracting, apparently even my silent presence is distracting sometimes!

This has taken me some getting used to, but now that I understand how essential alone time is to Michael’s happiness—let alone productivity—I am glad to give it to him.

Ultimately, I know that if he accomplishes everything he needs to during his focus time, he’ll be a much happier partner and much more apt to focus on me when I want him to.

#3 What People Think of Them is Important

There’s a good chance that if your boo is an entrepreneur, he or she is either a people-person or has had to become one. Entrepreneurs know that the likelihood of their ideas or companies succeeding rest squarely on what customers, investors, partners and employees think of them.

Most entrepreneurs strive very hard to maintain good reputations and keep highly involved in their local networks because after all, it’s not what you know, but who you know, and how those people feel about you.

I have been continually learning to watch what I say around people. As his partner, when I say things about our life or Michael’s personality, businesses or circumstances, I need to be careful to say things that shed the best light on him and give no cause for concern or gossip.

#4 Everyone Knows Them

And speaking of people skills, do you have them?

If you find yourself  more of an introvert, don’t worry; I know plenty of introverts who are able to hold a decent conversation and be sociably pleasant—both things which you’ll want to be able to do when dating an entrepreneur because everyone knows them.

While the amount of recognition your boo receives is directly proportionate to their particular industry, the size of their city and how long they’ve been hustling as an entrepreneur, chances are as you go out and about, you’ll meet lots of people who know your partner.

I joke now that even am consistently recognized while out by myself, and even if they don’t know my name, they know me as Mike Z’s fiancée!

As my partner’s brand grows, I will be dealing with this more, so it’s important that I have a genuine enjoyment and love for people, otherwise my somewhat-public life could become very tiresome.

#5 Podcasts and Books Will Be Entertainment of Choice

When Michael and I first started dating, I told him he was the first guy I had dated who read more books than I did. But I was off by a long shot!

Turns out not only does he read more books than any guy I’ve dated, he reads more than any guy I’ve ever known! I truly love this about him. He’s always filling his mind with words that feed his soul, with information that opens him up to new opportunities and worlds.

But I’ll never forget this one date night while scrolling through Netflix. “What show should we start watching?” I asked him.

“I don’t watch shows. I don’t want to waste my time addicted to something.”

So instead of nightly watching new shows, we read books. During the majority of our car rides, we listen to something that before Michael I had never listened to for five minutes of my life: a podcast.

The funny thing is that now I love listening to them! I have three favorite shows now: The School of Greatness, by Lewis Howes, The Art of Charm, by Jordan Harbinger and The Tony Robbins Podcast.

#6 You’ll Crave Outings With Other Entrepreneurs

Perhaps before this relationship, you never hung out with a bunch of entrepreneurs in various industries, mingling around a gathering of cocktails and stories.

That was me until I started dating Michael and found out that hanging with other entrepreneurs and their significant others is about the closest thing to heaven in a conference room that I can find.


Because they get you.

Even if you have no intention of becoming an entrepreneur—ever—you’re still with one and that’s a lot of work too. There’s a sense of camaraderie and understanding amongst entrepreneurs and their partners, a sort of unspoken, “I get you, kid. No need to explain.”

You’ll find yourself laughing at stories that ring only too true and sharing moments of sadness over similar frustrations and setbacks.

Most of all, you’ll see what drew your partner into this world and why he or she is willing to sacrifice everything for their dream.

#7 They’re Working Even When They’re Not Working

Even when your partner isn’t working, their mind is. It’s always on the hunt for a better idea, a new idea, or an idea to renovate an old idea.

You’ll be standing on the beach, arms around each other—as I have been very recently—gazing into the sunset, connected and in tune with each other.

All of the sudden she’ll say, or in this case, he’ll say,“Babe, I’m just really excited about getting this proposal finished. Once we’ve got this underway, I can give it to my team and they can handle it. You know, my team is doing so great. I want to scale up within the next year. I can see myself having thirty members on my team by the end of the year…”


Ultimately, the fact that your entrepreneur partner accomplishes so much is due to the fact that he or she is a mind-machine, constantly strategizing and architecting new ideas, business plans and ways to solve problems or prevent new ones.

The fact that sometimes these plans and ideas will pop up during your romantic dates is just part of the territory. Instead of tolerating it, however, try increasing intimacy by learning to embrace it and roll with the topics. When a conversation like the one above occurs at unusual times and places in my relationship, I like to ask Michael questions and engage in the idea process.

It beats pouting and having a bad evening. I’ve even learned to look forward to these moments of observing close-up how my partner’s mind works. I’ll usually say things like, “Oh really? Tell me more about that.” “How would this affect that?” “And what would need to happen for you to get there?”

And instead of entrepreneurship dividing us, we are brought closer together through it.

Which brings me to my next point.

#8 Their Entrepreneurship is Contagious

I laugh about the days when I thought I wasn’t an entrepreneur myself—and thought I never would be! Hilarious. If you’re dating an entrepreneur, be prepared for them to ask you questions about how you are living up to your own potential.

You can expect them to push you to pursue your dreams.

And just in case that sounds daunting, by the time you’re in a relationship with them for awhile, and after attending masterminds, conferences and workshops, reading one recommended book after another and discovering your own favorite podcasts, you’ll probably want to.

Entrepreneurship is contagious. There’s something about being your own boss, discovering your own gifts and talents and pursuing financial freedom that makes the idea of being an entrepreneur very enticing indeed.

And then there’ll be two of you, but I’ll save that for another article.

#9  They Need Regular Encouragement

It goes without saying, but being an entrepreneur is anything but easy.

There are many days and moments when my partner is feeling down and while I may not be able to fix anything per say, I can be a steadying source of encouragement and light.

Chances are, if you’re with an entrepreneur, you are the cheerleading type, meaning that you give encouragement and that’s what attracted your partner to you in the first place. So keep it up. He or she needs your light more than you think, and believe me, it can go from amazing to super dark really, really fast.

Be prepared for the rainy days by taking care of your own emotional health and loving yourself well. Even if your partner is the most positive, glass-half-full kind of person you know, there will be times when they can’t see the light at the end of their noses, let alone at the end of the tunnel. Especially since so much of their work is in the public eye, you, the person closest to them with whom they can be real, will be needed to help them see the light.

And by light, I mean that sparkling, effervescent potential within them and within the dream they cherish—one of the key things that made you fall in love with them in the first place.

You’ve got to believe in it more than they do so that when they question their entire existence, you can remind them.

You might also like…

From Poor Indian Village To Leading App Developer

From Poor Indian Village To Leading App Developer

Praveen Narra grew up in such a small town in India that when he was studying in school, the roof would leak when it rained. During his education, only two teachers taught five grades. “It wasn’t an easy journey all the time,” he says to me, shifting his...

How Elon Is Revolutionizing Business & The World

Like most entrepreneurs, I push myself to be innovative. I like to think I’m making a difference in the world. I incorporate daily routines and ideas from inspiring leaders, and I even prioritize my top three tasks every morning. Anyone who knows me will tell you...