adrian gee

1 year ago

How to Date a Self Funded Entrepreneur in His 20s

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How to Date a Self Funded Entrepreneur in His 20s

As a budding entrepreneur in my 20s, I lived most of my twenties trying not to spend too much on a lavish lifestyle 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 didn’t inherit family wealth and is attempting to start a business in his twenties. 

He/ she may come from a middle class background and scrounge up some money through the years to afford rent, staff costs, software and other start-up costs. This got me thinking about the asymmetry of dating an entrepreneur.



How to Date an Entrepreneur: Cars, Cafes and Condos


Starting out, I had to make sacrifices: if I ate out at a high-end restaurant for $30 a meal, I am giving up four days of chilling out at a cafe so I can enjoy the ambience of working without needing to rent an office.

Now, I’m not saying an entrepreneur is all work and no play. I dropped more than a couple of grand on a Europe solo backpacking trip and many solo flight trips in my twenties to take momentary breaks from work.

Secondly, 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 a premium per meal. 

I also once hired a freelancer for 8 USD to download all my Facebook photos manually.

However, what I’m saying is that a wise entrepreneur in his 20s is going to be prudent, delay gratification and think of long term outcomes.

This is why if you’re looking to date an entrepreneur, especially if he/ she is self-funded, there may be a huge pay off down the road, but you got to be patient. 


Dating and Entrepreneur Isn’t the Flashy Cars and Condos


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 calculated the cost of owning a second-hand car is 1.2k–1.3k per month inclusive of loans, tax, petrol and insurance.

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



In fact, my dates for the most part in my 20s would consist of walks in the parks, books, and intimate discussions.These date activities are low in cost, healthy activities and free. In some sense, dating an entrepreneur is akin to dating an oddball. 

If you’re doing it right, the women you meet is going to be totally okay with dating you without requiring a lavish lifestyle. 


The Short Term Implications of Dating an Entrepreneur


Let's look at the short term and long term implications of dating a bootstrapped entrepreneur.

If the relationship extends beyond a short term arrangement, it is something she has to make a choice based on her values in time: “suffer” alongside him, give up on signalling a perfect life on social media and reap the rewards years later OR… give it up.

The wise entrepreneur is going to re-invest his earnings into the company.

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

However, this problem can be solved, if you are an entrepreneur starting out, and you’re not willing to expend monetary favours. Then you should pick up some dating skills, charm and wit

Hence demographically, you are only compatible with women who are financially independent after graduating from school and aren’t looking for a cash cow/ sugar daddy.

The average graduate (or non-graduate) who signs up for median employment in any Western culture is bound to find herself with some form of stable disposable income. There is no reason to go about splashing tons of cash just to date someone.

The self-funded male entrepreneur may only be demographically compatible with prudent and wise women who not only meet his physical criteria but also are able to accept delayed gratification. 

The problem comes when 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.



The Long Term Benefits of Dating an Entrepreneur


In the long run, if a driven entrepreneurial individual stays the course and finds asymmetric financial success later on in his process, his demographic is now enlarged. He/she has money. He/she has choices.

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

Hence, dating an entrepreneur is asymmetric in nature. You may get extreme payoffs in the long run on either side, or bail out in the short term. This isn’t the case for most millennials in their twenties or thirties. For the people reading this and still think it's fun to date a bootstrapped self funded entrepreneur, I'd like to tell you to think twice.

This is the reality of dating an entrepreneur.

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