Dating an Entrepreneur – Date Poor Marry Rich?

By Marcus Neo | Dating Advice for Men

Jan 12

Something struck me when a friend recommended that we went to an above-average priced restaurant. I declined in mind about the price of the food. As a budding entrepreneur, I lived most of my twenties trying not to spend too much on expensive restaurants as I kept my expenses low in order to start and grow a business.

For the men and women reading this, the following is an accurate depiction of reality when you are dating an entrepreneur who doesn’t inherit family wealth and is attempting to start a business in his twenties. He/ she is probably going to come from a middle class background and scrounged up some money through the years to afford rent, labour, software and minimal start up costs.

This got me thinking about relationships and the asymmetry of dating an entrepreneur.

The Asymmetry of Dating an Entrepreneur

For the most part, I never thought like a CEO or a capital allocator. In my former years, I spent my majority consulting, business income away on flight tickets, restaurants, bars, clubs, cafes and convenience. Yes, I did reinvest in my own education and in my own company, but I didn’t do it at the rate that could lead to an exponential growth of capital.

I lacked focus.

I realized the importance of capital preservation and how a small self-funded company should reinvest its earnings into growth.

Technically, if I ate out at a high-end restaurant for $30 a meal, I am giving up four days of chilling out a cafe ($7 per coffee) so I can enjoy the ambience working without needing to rent an office.

Sometimes, my mother sways and she invests small amounts of capital in Ponzi forex or cryptocurrency trading schemes. I used to berate her for it: ‘do you know how many hours of my staff I can purchase with that amount?’ It’s about time I took my own advice.

This is why if you’re looking to date an entrepreneur, especially if he/ she is self-funded, it’s difficult.

Now, I’m not saying I am not awash-ed with cash and I’m swimming naked. I’m also not all work and no play. I dropped more than a couple of grand on a Europe solo  backpacking trip and many solo flight tickets in my twenties. I also dropped a lot more than a couple of grand on self-education.

However, I’m saying: let’s be prudent, delay gratification and think of long term end outcomes.

How to Date an Entrepreneur: Cars, Cafes and Condos

Not all money spent isn’t well spent. For example, I am a convenience freak. I outsourced all of my lunches for months at a go and paid premium per meal. I also once hired a freelancer for 8 USD to download all my Facebook photos manually.

On the other hand, I didn’t purchase a car for years and am not intending to. However, I’m more than willing to spend on ride-hailing applications. They are worth it. I figured the cost of owning a second-hand car is 1.2k–1.3k per month inclusive of loans, tax, petrol and insurance.

I also kept my personal insurance premiums to a minimum and berated my parents for purchasing whole life insurance.

I also don’t invest any more than low-cost first dates or attempting to impress the opposite sex through monetary means. I’m against the idea of regularly going out to expensive restaurants, cafes and flaunting them on social media.

If given a choice, perfect dates would consist of walks in the parks, books, philosophical discussions and mind blowing sex. These activities are mostly low in cost, healthy activities and free. In some sense, I am an oddball. I realised this isn’t the case for most millennials in their twenties. For women reading this and still think it’s cool to date a bootstrapped self funded entrepreneur, I’d tell you to think twice.

How to Date an Entrepreneur: Asymmetry 

Let’s look at the short term and long term implications of dating a bootstrapped entrepreneur: for the opposite sex, if our relationship extends beyond a short term arrangement, it is something she has to make a value choice in time: “suffer” alongside with me and give up on signalling a perfect life on social media and reap the rewards years later OR… give it up.

I realized this also translated into my friendships. I can’t go cafe hopping or club hopping every other weekend. It’s much wiser to re-invest the earnings into the company.

Now, as I mentioned, it’s not that I am not awash-ed with cash or swimming naked. It’s just that I’d like to continue swimming with my head well above the water.

Once again this puts a self funded entrepreneur in his twenties in an asymmetric dilemma: attractive women are traditionally used to cash/monetary gifts/ favours from men.

Since I am neither rich nor willing to expend monetary favours. I can only rely on charm and wit. Hence demographically, I am only compatible with women who are financially independent after graduating from school and aren’t looking for a sugar daddy.

The average graduate (or non-graduate) who signs up for median employment in Western culture is bound to find herself with some form of stable disposable income. Her lifestyle choices might not match with an entrepreneur in his 20s or even arguably 30s.

The self-funded male entrepreneur in his 20s is only demographically compatible with prudent and wise women who not only meet his physical criteria but also are able to accept delayed gratification and book dates. (Read: I can assure you it’s a minority).

Let’s just say if every one of her peers got boyfriends as bankers, lawyers and doctors, she is going to feel the social pressure to keep up with the Jones.

In the long run, if a driven entrepreneurial male in his 20s stayed the course and find asymmetric financial success in his 30s, his demographic is now enlarged.

He has money. He has choices.

If he has not found a committed and suitable partner in his twenties who is willing to go through the delayed gratification for the bigger picture. Then let’s just say he is in an asymmetric position of power in the dating game.

Hence, dating an entrepreneur is asymmetric in nature. You get may get extreme pay offs in the long run on either side, or bail out in the short term. This is the reality of dating an entrepreneur.

About the Author

Enjoys writing about dating, relationship, business, and psychology. Introvert yet extrovert. Likes martial arts and music, but never got around to the latter.

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