mcdoug

Will do. I have some sales experience though I never worked as a dedicated sales person. I've made cold calls that turned into paying gigs and I've done sales as an engineer: go present the technical aspects of the product and take potential customers from "who the hell are you guys?" to "how can I give you my money?". I also have a lot of negotiation experience and do quite well with that, but never a bad thing to get better at it.

Money can buy me time, which is one of the most limited things we have on this earth. I know what you are saying and this is advice I've often given as well. But please consider that I never said that I was looking to buy happiness. I want money for practical purposes and I know what it can and can't do. I am quite happy in my personal life and money can only mildly enhance that. But I also am tired of budgeting for whether I need new tires or to get my moles looked at this month. Whether I should invest in a retirement fund or my kids' college fund. Whether I can go to a restaurant or buy a new pair of slacks and a couple of shirts. Whether to keep living in a house that's bursting because it's too small or sell my soul to a mortgage provider for a bigger one.

Wow, this is one of the most helpful comments here. If I can ask for some details:

The CEO track sounds nice. I've done the middle management stuff before and was quite successful at it. In my last job I was heading up the software team for a software/hardware startup, as well as taking on partial management of the support team and the data entry team. I have been C-level at two companies but both were early stage when they went belly up so this is more a bullet point on a resume than something I can point to and say "look there it is". Currently I work for a small enough company that there isn't any more upwards mobility here. I am basically working as an individual contributor directly with clients. The projects are boring but the pay is good and the people I work with are excellent. How would you suggest making a leap from here to something bigger? I live in an area with lots of banks and insurance companies, but not much in the tech world.

On the finance side, again, how do you go about this? What kind of companies do you suggest and what jobs in them? Are hedge funds a good idea? Or do I need to commute to something like NYC and apply for something with a large investor? What qualifications should I focus on before jumping into this? Is mostly reliant on knowing the right people? Is it about technical knowledge of the subject? Or is it about impressing the right interviewer?

It's possible I also just needed to rant about how tired I am of the rat race. You are right of course (though I might not 100% agree on your point #3; valuable connections often come out of spreading the word about your project and my motivation usually increases afterwards).

Yup, I've had good luck with those in the past. Main problem: I am not making way below my market salary. I might be maybe $20k lower than average due to some job perks, but just switching from small software company A to small software company B won't make me a ton more money. Equity in a hot startup might, so I guess I'll be on the lookout.

I haven't seen that particular book and will give it a read, but I have attempted about a dozen lifestyle SaaS businesses. All went best like I was selling peanuts at an allergy sufferers' convention. I am always looking for more opportunities for something like this, but nothing so far has had the right overlap of profitable/my area of expertise/not requiring a stupidly high upfront investment.

Mid 30s. I have a small but slowly growing stock portfolio. If I keep going the way I am, in 5 years I might be able to buy a Model 3 with its worth. My family growing up invested in my education, not in a stock portfolio, so what I have is skills, not cash.

Balance is important. This is why I'm not willing to sacrifice my family, but I am willing to work differently or in a different field. I am old enough to know what balance feels like to me and am always looking to make sure it's maintained.

I am pretty much as high up in my company as I can be without being an owner. We don't use these terms, but effectively I am occupying the role of the CTO.

With the current pandemic I am doing very little going out. That doesn't mean my expenses are better off though. I am directly supporting two kids and my life partner who works but her career is very low paying. She takes care of most of her expenses but housing is on me. I indirectly support two other people because I care about them and their well being. I am stuck living where I am because I am divorced and my ex won't move. If I move I don't get to see my children, which isn't an option for me.

For #1, can you provide any concrete info? What skills, where to get them, how to start getting into that type of work, what does it pay and how, etc.

For #2, again, any specific advice? Are blogs still a profitable thing? What platform do you use to buy/sell blogs and/or plugins?

For #3, yeah already working on that one. Pandemic doesn't help with that.

I am not exactly comparing myself to tech billionaires, but more tech millionaires. Bezos was mentioned just because of the absurdity of his wealth, but I don't want to be that rich. More like, I wouldn't mind finding a way to part Bezos and about $5m of his money.

I have done projects of passion. Last one was completed in February and the business opened in March. For five days. Being a new business, it isn't even eligible for any kind of assistance, so what I did there was to sink a bunch of money and sign a lease so that I have the privilege of adding an extra $1200 a month to my expense list. Decreasing expenses is absolutely something I've been working on, but investing my wages will take decades to build enough wealth to be meaningful.

I 100% agree with you on all of that. I know that it takes both luck and building up to having that luck and the ability to take advantage of it to land something like Amazon or Instagram. I am not aiming to create a unicorn startup. I could probably write a few books on various subjects and see what sticks. Worst case, I get my writing bug exercised. Thank you.

At least I'm not the only one :)

Yeah, that's the problem. I am happy to invest a couple of thousand bucks into something, and while crypto can have some very large returns at times, I'd have to hit something just right for it to grow 500-1000x. I am sitting on some Stellars and a few other cryptocurrencies but the amounts aren't large enough. Even if I double my investment, it'll pretty much allow me to pay a month's of rent or so, not retire. Gambling huge sums requires that you are already rich. That's where a 5% gain in a particular cryptocurrency nets meaningful results.

I have seen a lot of these threads over the years on HN. Most give your two options, with an occasional "read pg, do a startup" type advice thrown in. Things I have considered:

- Switching careers to work closer to where the money is. For example, working for a douchey hedge fund that can pay half a mil a year if things are going well.

- Putting together a pitch deck, flying out to CA and pitching it to every VC who will listen. I have a decent idea for a dating app that solves a lot of the problems with the current crop of dating apps. A VC paying my salary for a year while I develop something like that would work well for me.

- Networking my way up until I am rubbing elbows with the ultra rich and looking for opportunities to help them spend their money.

- Playing the lotto until I'm broke.