The Highs and Lows of Dating a CEO

Hi, Hannah here ! Hope the past week has been delicious on many levels of life, and that your minds are open, drinks are in hand and we are collectively ready to dive into today’s topic. Which is, the peaks and pitfalls that are commonly associated with dating a powerful person. 

I’ve never formally introduced myself. HJG, Aka Hannah J Glasby. I’ve been a professional model for 16 of my 32 years, you do the math. Am a deep empath, lover of life and literature among so many others things that will most definitely find their way into upcoming blogs. I‘m also a future Feminella ( proudly might I add ) as I’m engaged to an incredible man, the actual love of my life. And he just happens to be the founder and CEO of this app. 

We met on Hinge ( shout out, massive thank you, lets definitely get in touch so we can share our lil’ love story lol ) it happened in a serendipitously similar way to how Joe’s app works. And exactly why it he created it. We matched and chatted the bare minimum, him asking when he could take me out… I gave him two options, my secret preference being later that night and to my relief, he chose the latter. We met mere hours later, got to know each other in person, connecting deeply and swiftly. Fell in lust immediately, love rapidly after and bar a much needed 4 month break in between, we’ve been attached at the hip for over 2 years now. 

But loving someone who started an app at the ground level is a testing thing at times, let alone being a woman with slight trust issues and it being a fucking dating app. And being engaged to someone who’s had a highly successful, slightly tumultuous career as an international model and is currently figuring out her next chapter is a unique and difficult hardship on its own. We can all agree that joining your life with anyone is bloody hard. But doing so with someone who embodies that CEO spirit adds an extra layer at times. Not for the faint of heart, nor ones lacking spirit/character or trust. I find it requires a lovingly high level of attention, with specific understandings and energy needed almost everyday. I’m sure my lobster would agree. I also know for a fact we aren’t the only ones, and that’s why I wanted to inwardly and outwardly discuss this subject.

Now most people, understandably yet very naively look at modeling through the heaviest rose tint ever. That it’s this non-stop glamourous pampering paradise where ego’s are filled freely, designer clothes as far as the eye can see and up for grabs. That we are fawned over like celebrities, have everything done at our beck or call and are being paid obnoxious amounts of money while we ( as my brother like to describe it ) just sit there and look pretty. Sure, there is some truth to that. I have been payed obnoxious amounts of money to get rubbed down and made up into the most glamourous version of myself, my literal job for that day sitting on a chair doing my prettiest facial expressions. But what people don’t see are the hundreds ( and I mean hundreds ) of hours spent in the mirror perfecting those expressions, or the multiple castings I had done with this client alone (my own time and money spent ) just to be able beat our 10 others woman so I get to exercise those skills that day. Not to mention the disapointing amount of ” we’ll get them next time ” from my agents that have come before the joys of getting paid that much for relatively that little. Nor the self confidence destroying scrutiny or rejection that’s inflicted from those castings, sometimes right to your face and the suffocating inner monlouge you develop as a result. I could go on and on, but clearly the metaphor for all of this is that people rarely see the struggle behind the success. 

People who’ve never been in the position to build a brand, a company, an app from the ground up struggle to understand what it takes. I’ve been the CEO, COO, CFO, #1 sales woman and employee of Hannah Glasby, Inc for well over a decade now. Yes, I have agents and managers, a kind of colleague/employee/confidant hybrid. And an entire team when on set to help me fulfill the clients brief. I have my family, albeit on the opposite side of the world for most of my career, I have my best friends and future husband as support. I have help, and I’m so damn grateful for it. But it’s me who puts in the hard work behind the scenes every day to achieve this dream of living out in the world. To make sure that “the product ” aka myself is 100% prepared in every facet any given day. Spending hundreds of thousands of dollars living and working in other countries. Who’s learnt different languages, assimilated myself to at least 6 different cultures, learnt how to do her taxes in 3 different countries… who sacrificed holidays, christmas’s, birthdays and any kind of normalcy of a social life. And it’s me who will ultimately figure out, pursue and dominate the next path I choose to take. Because I’m the type of person that loves to be thrown in the deep end. I know Joe does too and I think it’s a vein that runs deep through any and every powerful person. 

Thats why, for the most part, I’m able to understand on a deep level the unique in’s and out’s that Joe struggled with starting this app, and what he deals with as it grows. It’s part of the reason our relationship works so well, and is a very strong thread that connects us. People only usually see Joe with the smile that takes up half his face, and the ever positive attitude and outlook he encompasses radiating brightly. The charasmatic CEO of a dating app that is rapidly picking up steam and success. They only see the fun and joy that his events bring, only see the greatness and success he shares so freely when another milestone is made. 

I see that. But I also see the Joe wanting to rip his hair out after another meh meeting early on in the process trying to acquire seed funding. I’ve seen the Joe dejected and disappointed after another bar/coffee shop turned him down for an event. Laid awake many nights, listening to his frustrations, concerns, ultimates doubt over what this app would be and the fears of it not working for the people of today. I’ve witnessed countless days full of phone calls, texts, DM’s, emails, Linkedin messages in the pursuit of his happiness. That continues on even as I write this, I just got off the phone after another overwhelming day for him. And even though he does have a fantastic support system and team by his side, seriously they’re amazing, the journey of a CEO is quite a lonely one as the majority of the responsibility has and always will be on him. 

How to Happily Occupy the Passenger Seat 

Now, I can’t drive. Well I could in an emergency, but not legally nor have I ever held a license in any country. So I am quite literally always the passenger lol. However when it comes to my own life and business, I’ve always been firmly in the driver seat. Now if we continue on with the automobile metaphors, a forever relationship like mine morphs your individual cars into somewhat of a extra wide SUV. And you spend your time taking turns loading, unloading while driving or taking the passenger seat. Relinquishing or even sharing control is hard for any powerful person, because you’ve spent so long solo driving down the highway life. So wrapping my head around not only letting someone drive, but also decide momentarily where its heading continues to be somewhat difficult. Yet incredibly fulfiling, I explain more in depth below.

Clash of the Ego’s 

Power struggles are a definite possibility. The balance betweens lovers is a delicate one at the best of times, ever changing and demanding. And when it comes to dating a CEO, takes a strong and secure person to allow the dynamic to dip in the other’s direction for a prolonged period of time. However I’ve found if there’s a mutual respect of each others contribution, perspective and individual journey, that struggle is more of a playful tug. 

Serving up your skills

Part of starting any business is getting some recognition and buzz flowing. In my case, it’s going to industry parties, posting curated stories and posts on my instagram, leaving a stella impression on clients so they become a repeat and spread the word. Specific to apps, users are what we need at the ground level. Aka people on and actively using the app. How does one get users ? Social media, sure. Word of mouth, yeah maybe depending on your circle. But collaborating with brands, in our case bars/coffee shops and offering a free drink in exchange for a download was and still is the main fortay. Now I’ve been to countless activations and pop up’s, with so many to come in the future. And while doing so, have been actively asked by friends and strangers alike iterations of the following questions… “Well he’s not paying you, so isn’t he just using skills for his own benefit ? and “Damn, it must be hard really hard concentrating all of your energy and free time on his app, I could never.” The ever present “What about your career Hannah ?” or my personal favorite ” What do you get out of this ? “

Yes, damn straight he is. I’m no fool.. I know what I bring to the table and so does he. I’m a model, and a natural born saleswoman. So why wouldn’t we utilize our respective skill sets to further this dream in whatever way we can ? Understand that I’ve had to meet, connect, work with and befriend so many people through out my life. I’ve waded through a plethora of personalities, a multitude of moods, so many different dynamics that I’m lucky enough to have this rolodex of sorts stored. Overflowing with quick relevant retorts and charming anecdotes that can apply to most environments, I’ve been known to intimidate quite powerful people and can hold my own in any room. So all of this, aided by my naturally confident energy and true belief in the company tends to go down quite well as I pull you off the street, offering a beer/coffee as I gently make your single self understand why this app is necessary for life. 

Yes, it is hard at times. And for some people, it’s unimaginable. I’m a woman, with an EQ through the roof and a sex drive to match. A constant stream of connectivity, passion and spontaneous outings is where I thrive. And sometimes Joe’s attention may be the furthest away when I sometimes need it the most. But any sacrifices of a ” normal ” social life, dates that may have to be dismissed or nights planned changing on a dime is something I know first hand through sitting at the helm of my own company. And understand must be a part of our journey right now. 

My own career ? Two main points here…I was working 14 hour days in a different country when most people my age were getting drunk at house parties and complaining to their mum’s that dinner wasn’t ready. I’ve worked my ass off for the last 16 years, and while starting this new chapter is one of the more overwhelming things I’ve ever encountered, I know I’ve deserved the right to rest on my professional goals for a little bit. Secondly, rightly or wrongly in this woke world we live in…I am a born career and an innate cheerleader. While I have an abundance of amitbiton and will always be striving for my own excellence, my main passion since I can remember has been family. Being the best and most supportive partner for Joe, daughter/sister/friend ( you know who you are ) and preparing to be the best parent to our future children is my job for now, and I couldn’t be happier about it.

Lastly, what do I get out of this ? As each generation gets introduced, so grows this obsession with instant gratification. I understand that it takes time to build greatness. I choose to invest as much energy that I do because I believe in the app. But more importantly, I believe in Joe. So to answer this question, I get a lot. I get to help the love of my life make his dream a reality. A feeling so good it gives me goosebumps. I get to exercise my own skills in a new arena, helping in part to figure out my next chapter and I learn something new every day. I get an unknown amount of future adventures ahead, able to experience them side by side with my soulmate. I get a partner that’s so determined, kind, funny and ambitious, I know our future will be comfortable anda adventurous, our family well taken care of mind, body and soul. That is more than enough for me. 

These are just a few pillars of conversation that I feel we deal with being a powerful duo. But like any relationship, regardless of job, stature, bank account etc, that list can grow or shrink on any given day. I think the main point of this blog is to express that yes, opposites attract. But what a joy it is to meet your meant to be match, and know that while every level of life will be challenging in the wildest way, it will also fulfill and enhance you in a way nothing else can. 

As always, I hope your nights are safe/drunken and your days filled with a joyful amount of positive productivity. Until next time Friends and Fromies x 


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Aussie Model in LA 🇦🇺 Blog Writer and Co-host of First Rounds On Me Podcast

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