I came across this ridiculous article “Why is it impossible for Entrepreneurs to have Girlfriends” spreading a pro-masculine drivel that rivals some of the worst feminist content online.  In it, the author references Bill Gates and Jay-Z as  the best examples of sacrificing love for entrepreneurship.  Its another example of a great headline, bad content; and its unfortunate, because this topic needs to be discussed as the number of entrepreneurs increases and the birth rate declines.

Why Entrepreneurs struggle in healthy relationships

Is it impossible for entrepreneurs to have girlfriends?  There are many challenges, most based on these mental models:

  • Startups as Religion
  • Startup as child
  • Startup as Hero’s Journey

Startups as Religion

The Startup Culture is not unlike a Religion: if you work hard in this life, you’ll be rewarded in the (post-IPO) afterlife where you’ll meet all of your idols in the paradise of some secret club in Palo Alto.

This religion, like any other, succeeds by encouraging daily dedication and centering your life around the Church activities.  Is attending the next networking event important for your business?  If its just a business, no; if its your religion, how could you say No to Church?

The problem with making Startup Life your religion is the incompatibility with heretics: if you date a non-believer, eventually your fundamental views will clash.

Startup as child

Another (more satisfying) model to consider is your startup as a child.  Like a child, your startup demands an incredible amount of energy  and sleepless nights before it can take care of itself.

If you co-founded a startup, your future girlfriends will never understand the intimacy you have with your co-founders, as you will behave somewhat like a married father looking for a girlfriend on this side, but your girlfriend will always pine to have your full attention and commitment.

If you the lone founder of a startup, your life is not unlike a single parent: you’re happy to date people, but you’ll completely drop them and vanish if your child needs something.  Like a single parent, you’ll apologize for your actions, but then hurry home, comforted in how important you are to your startup.

This becomes more true as you hire employees: the decisions in your personal life now impact dozens of people who rely on you to put food on their tables.  You can’t reasonably walk away from your startup to chase a relationship, just as a single parent can’t just walk away from their parenting responsibilities to chase a relationship (though some will.)

Many single parents realize this incompatibility and drop out of the dating scene altogether.

The Startup as Hero’s Journey

Another model here is the myth of the Startup as Hero’s Journey. In this myth, the lone male entrepreneur hero fights off distractions (including women) to create something special that will change the world (or at least his bank account.)    Notably, Campbell’s version of this includes the stage “Woman as Temptress”.  If you accept this framing of your relationship as temptation away from your journey, you won’t be able to hold a healthy relationship without blaming her for your failure.

The Myth of Working Hard

Given these two memes, which one would you believe?

Actually, they are both wrong.

When we look at the stories of other Entrepreneurs, we might embrace the worldview that in order to succeed we must work 100 hour weeks.  This myth is the fastest growing idea in America today: whether you are a male hero entrepreneur or a lean-in woman, the secret to succeeding in this life is working harder and outsourcing your personal life to others.  If you fail at life, its because you weren’t willing to work hard enough to have it all.

Countering this is the meme of the accidental millionaire who reads 4 Hour Workweek, prototypes a new product, and in three months has passive income.

The reality: working hard doesn’t guarantee success, and working harder is counterproductive at some point.  Working as little as possible certainly doesn’t guarantee success, though it can manufacture some cool appearances of success.  Both memes fail to consider the truth about opportunity cost: work too hard, and you’ll lose in other areas of your life.  Work too little, and your business will lose some benefits.  Instead, you should be looking for ways to advance your business by encouraging its autonomy and supporting the Hero Journeys of others.

How to have a happy relationship

Given all of this, is it possible to have a healthy relationship with both your personal ambition and a real human being?  There are two ways to accomplish this: date within the church, date a single parent, or adjust your life script.

Date within the church

If you insist on being a member of the Church of the Startup, you might try dating within the Church.  Maybe you’ll find another entrepreneur and you can share your stories of success and failure as you take parallel journeys.  Alternatively, you might dating a Startup Cheerleader provides consolation when you’re hitting speed bumps in your first Startup, but know you might grow wary of them when you find some success.

Date a Single Parent

If you find slim pickings in the Church of the Startup, and you are a lone entrepreneur, you might date a Single Parent.  This is great because they enter the relationship with the same expectations: your relationship with them will be second to another relationship that is more permanent and valuable.  The downside: they won’t fully understand your religious ferver, and you won’t understand their devotion to a child that can’t be sold to Google.

Single Parents are a fast growing demographic in the U.S., and if you choose correctly, you’ll never have to change diapers, because what entrepreneur has time for diapers?

Change your life script

The final choice is to change yourself: understand that a relationship, like a startup, yields amazing benefits one you lay the initial foundation to make it succeed.

If you are in the initial stages of your startup, starting a serious relationship will be difficult, but if you have a business in the growth stage, ask yourself whether you need to work heroic workweeks to achieve the results.

Ask yourself if women are temptations away from your life’s work or if they can add meaning to your life.  Decide whether your legacy will be children who will starve from global warming or a software startup that eats people.


Startups, Girlfriends, and Children demand time and attention.

You can’t have it all.

Choose your religion wisely.

Why It Is Impossible For (Most) Entrepreneurs To Have Girlfriends