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Culture War Roundup for the week of April 13, 2026

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Reading a recent shagbark post about how women are attracted to men who don't have bosses over 'wagies', I found myself thinking about owning a business. As as American it's obviously glorified, but I'm wondering if it's easier to own a business now than it was in the past?

Seems to my relatively uneducated mind that over time in America owning a business has in some ways gotten harder, some ways easier. Nowadays you can do the online business, make money not doing anything physical, just using your wits and social network, basically. Forms can be filled out electronically, etc etc.

On the other hand, back in the day it seems most Americans used to be business owners, especially when more rural lifestyles were more common. Folks owned farms, or a general store, and didn't really have many forms to fill out, though of course they paid (much lower) taxes.

Anyway as a somewhat half-assed tie in to the culture war - which tribe is better for business? Red tribe nominally wants to be but... they also seem to not follow through with that a lot. Blue tribe has become more kleptocratic lately. Maybe it's a tossup?

As a serial entrepreneur I can give it a mixed review. Starting a business is hell, operating a reasonably successful business is superior to being an employee. Most companies fail, so most entrepreneurs will only experience the hell.

The difference between being self employed or freelancing and running a product company is vast and underappreciated. A freelancer is effectively an employee constantly chasing new contracts. Job stability is traded for higher income and higher flexibility. This path is works for self-motivated competent people. My best advice is to find freelancing work first and then start freelancing. Don't quit your job to start looking for freelancing gigs.

Product companies are a different beast. Developing a product or a service costs far more than you expect, takes longer than you expect, and it is harder to sell than you expect. There are so many aspects of a company and if you fail one, your company fails. A few years down the line life gets better. I don't have that much to do any more. Tech team has its road map, customer support has some questions, sales and tech team are bickering as usual, and I need to settle their dispute. I have a few candidates to interview. Other than that not much happens. More time is spent eating lunch and maintaining relations with people than actually working. Building and creating processes and institutional knowledge from thin air is tough, keeping them in maintenance mode isn't nearly as hard.

As for dating being an entrepreneur is a terrible idea. Expect to work far more than average. Expect to be in a world with 90% men. Replying to tinder messages is mentally taxing when you have dozens of unanswered slack messages and emails. Being in the right headspace for a date is tough when one of the investors is acting up and making absurd demands on a call a few minutes before the date. As you become successful you will be invited into new social circles. These social circles consist of married men who are older than you and who don't now 25 year old women. Women are far less interested in hearing about your startup than you think. It takes years to make a business profitable and during these years you are broke, over worked and don't have a real job according to women. You can have a company with 100k in monthly revenue and a team. If your expenses are 100k you make no money and women think you are unemployed spending your life on a hobby.

The stereotype of the new money man with a golddigger isn't purely based on the poor taste of new money. If you are stressed, only know men, work crazy hours and don't have time to date gold diggers will be the women you meet. Who will chase a guy on tinder who is average looking and rarely replies but has a fancy watch? A guy in a bar who doesn't go out a lot and hasn't had much flow with women for years and is severely sleep-deprived will only impress certain types of Asian and Eastern European women.

If you want to meet women get a job with average pay that is a bit relaxed and where you meet a lot of women.

Interesting, thanks for the response! Yeah it's easy to romanticize business, I'm sure it's quite difficult in practice. I am already engaged so the lady part isn't relevant for me necessarily, but I always do wonder if I could have more freedom/time/dignity as an entrepeneur. I don't know, seems like it really depends!

Running a business is really rewarding and the only real path to true success for most people. I am grateful that I went into business.

With that said the results vary wildly and getting going is tough. If you have an opportunity take it. If you are going the freelancing route you can take your time and secure some clients first. If you want to found a product company then make sure to do your research.

No, you won’t.

You might have more money as a small business owner. There’s even business models with very low risk- someone else figured out how to do it. But you will be working 80 hours a week for that money.

Idk, I know a few people who have lifestyle businesses where they essentially sell an online course or some other low-effort offering, and after a couple years of work have set themselves up to make plenty of money and work maybe 10 hours a week.

Probably quite difficult, but it's doable!

Those people are the equivalent of Instagram influencers. It’s folly to think you’ll be one.

The average contracting or restaurant business has a decent shot of making it, so do tech startups. This is essentially aiming at being a celebrity.

Well, fair. I appreciate you giving me I suppose a dose of reality. I've always been frustrated with my jobs so the grass seems a lot greener on the other side, but knowing myself I'm not sure I have the temperament to run a business successfully.

Agreed. If you're starting your own business you will be working like a dog. "I work 10 hours a week and make $$$$$" is a scam.

I mean, the person I'm thinking of isn't trying to get me to sign up for anything. She has no reason to lie. She just built a course to prep for a data science exam and has sold it well since there wasn't much else in the niche. I don't see how it could be a scam, like MLM style.

It's not a scam in the sense of getting your money, it's a scam in the sense of many self-employed people presenting an extremely biased account of their company, for various reasons, including self-justification. My brother-in-law runs a platform providing niche courses in psychology, and he constantly talks about how this kind of platform can create almost "free" money with minimal input from him since he only does the course once and then an unlimited amount of people can take them (and others can use the platform to create their own courses and he gets a cut, even more free money!). Except I know him & his life well enough that he spends a lot of time on it, regularly even on weekends, and from his wife I know that so far including all the running costs, the set-up costs (he isn't a programmer himself, so especially in the beginning he paid a handsome sum just to get the basic framework going), the gear he bought to make professional-looking courses ... he is basically still treading water. Maybe it will change, maybe not, but if you know him casually you might think he is making decent extra income with little work, the way he talks about it.

But maybe your people are for real. It's not impossible, just unlikely.