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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?


C-level at a startup is probably comparable to middle-manager at most companies, so like 10 reports. CEO track means you're in charge of like a hundred people minimum. You don't apply to jobs any more in the traditional sense. Companies hire executive placement firms to hire you. For your area, you probably need to find VPs from the big companies there and ask them about how their career path goes.

If you want to get rich in finance go to Harvard and get your MBA, and then just follow what everyone else around you in your class is doing.


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).


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.


Then maybe add more because the market returns are suppose say 5%, but they are generally much more higher, around 10% over a 15-year period. Over 14-years that money doubles, but the market is performing at 10%, and even higher lately, so that's 7 years. So instead of buying that model 3 in 5-years if you continue adding small increments that Model 3 turns into a Model S in 7-years.

The issue is many people hold a savings account in cash but then inflation eats you up, or they store it in a savings account, but then you break even with inflation. Taking advantage of compound interest is huge.


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.


To me your goal should be a better payed role. I assume with your VHCOL that there are better jobs available. I would work on landing something better at big tech (FANG ideally).

Once you're there you can focus on your side projects or building your own SAAS etc.


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 :)


Count me in :)


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