"and a leaderboard"

This is not the idea you are looking for...

You have identified a well known area of interest... but you are not solving a problem. If a problem can't be solved with conversation with a trusted friend or relative then it's a slim chance an app and leaderboard are the right answer.

How to schedule saving for retirement, annual fees, ETFs vs index Funds, index allocations, optimal portfolios based on personal temperament, and when to (very seldomly) change allocations (if ever)?

The key idea behind index investing is paying low fees.

Non index funds perform the same as index funds (and research indicates you can differentiate the ones that outperform a priori with any method). But those funds have higher fees.

They do. Vanguard doesn't charge anything extra for retirement accounts. It's just a matter of ticking a box when you sign up. Schwab is probably similar.

I have a Schwab Roth IRA. They don't charge anything.

Hurry up! :)

or do a website...

Normally you mix with bonds to get the level of risk you want

The one advantage of Vanguard is that the company itself is owned by its funds. So the very people who pay the admin fees are the ones who vote the leadership in or out. So raising fees would be unlikely unless necessary and they are known to be very frugal as a company as well so I feel like they are unlikely to need more fees. Especially with almost $3 Trillion under management.

Of course, there isn't any real cost to switching. So you could always switch to Schwab or vice versa as needed.

And old person (over 30)

The issue is that even after dramatic crashes my impression is that stocks generally beat bonds long term. That means that if one person put all theirs in stocks and the other in bonds the one in stocks is likely going to have more money later, even if the market crashed a few times in between.

I've read some of those web sites and they're insufferable. Buy a house in cash so you have no payments, shop only at Goodwill, collect rain water for drinking, and never, ever get sick, and you, too can retire at 40!!

> I'd love to see a Financial Independence plan around growing [a] business(es) and retiring early but not crazy early (40-55) and living on a substantial middle/upper-middle income for several decades.

That's roughly my plan. My goal is to achieve financial independence, but my wife and I will continue working even after that. FI just gives us the freedom to do work the way we want.

My current projections put us at retiring roughly when we hit 40.

I just started my own business, which I hope to grow into a indiehacker/lifestyle type business; not a rapid growth startup. Just something I like working at and that earns a reasonable income.

All that said, I'm not sure why you think $24k/yr is a pauper lifestyle. In fact that's roughly our yearly expenses once we achieve "initial FI" * . That's in Southern California, and we hardly live like paupers.

By the way, I never got involved in the FI "crowd". I read through /r/personalfinance in the past, and check it occasionally. It's definitely very heavily expense management. Makes sense, since most people are really bad at expense management. And there is definitely not a lot of discussion about where to draw the line between cutting expenses and having fun. I can imagine that FI specific communities would be much worse in that regard.

But I think all of that is driven by the fact that these communities are composed of, well, everybody. And most everybody can only dream of maxing their IRA. For people in the HN crowd financial management is quite a bit different. We need advice on what to do after we max our 401k! (HINT: Start your own company and do a solo 401k). I think a lot of us are also very privileged already in what work we do. If you're a programmer, you can generally find a programming job you life that pays very well. For most everybody else, finding a job you life is either rare, or would mean taking a massive pay-cut. So while most people dream of FI being an escape from work, I think a lot of the HN crowd is like me; dreaming of FI as just ... freedom. Freedom to take a year off and work on a startup. Freedom to work for a local company for $150k/yr instead of working for Google to earn that fat $300k/yr.

EDIT: * Forgot to clarify that "Initial FI", for us, occurs after our house is paid off so $24k/yr is without a mortage. I editted out long-winded sections of my original comment and forgot to clarify :P

That's one way of doing it, but there's no one-size-fit-all solution. Some do what you said and just stop spending anything. Not everyone retires either, it's just that they do work they like because they can afford it rather than having to.

It's really a personal experience, I know myself I don't feel like my life is missing anything even if I'm putting money aside to my future. I'm still traveling at least once a year, and I eat pretty good food all the time. At the same time, I don't have a car and rent one whenever I need one.

What confuses me most is how people expect to pay for healthcare costs, which keeps going up. I'm an independent contractor and it costs me 1k a month. More than double with family.

East Bay, work in South Bay. 580, 680, 880, 280 are all often parking lots during rush hour.

I don't think a 7% interest rate is unreasonable. One of the advantages of planning on early retirement means that you can take on a lot more risk with your investments, eg. putting everything into stocks (which isn't really "gambling" -- over long periods they've only ever gone up). If the markets are totally hammered the year you want to retire, no problem -- just keep working a few more years until they recover. And saving $75k a year is also quite reasonable if you have a high income, like a doctor or well-compensated engineer. I’m only a couple years into my career and am supporting my wife and kid, but we’re on track to save a bit more than that this year.

Of course, the lifestyle choices we make aren’t for everyone, and that’s fine. But they’re also not totally crazy. We can save that much still live about as well as the median American, and a lot better than the median human.

Borrowing on your home to invest is just a terrible idea. You may see higher returns on the aggregate in the market but doing so is a good way to lose your home. Too much risk and like you, I think the small spread (and it is very small) between your mortgage and market returns doesn't even cover the risk premium of the potential to lose your home.

I don't think real estate/paying into your mortgage is risk-free. I'd say it's about as risky as long term investments into the stock market.

Over all of recorded history, the stock market has gone up 10%/year on average (not accounting for taxes/inflation).

The common rebuttal to that is that past performance is not an indicator of future performance.

Sure, but then you have to apply the same logic to the supposedly "risk-free" real estate. I think it's just as likely that your house becomes worthless as the stock market no longer giving 10% returns.

My more general argument is that for all intents and purposes the stock market is a gauge of the overall economy. If suddenly the stock market stopped returning 10%/yr the economy as a whole would be in serious trouble. No investments, real estate or otherwise, would be safe. Your stocks would be as worthless as money stashed under a mattress.

That's my logic, at least. Of course, as I said, I don't follow that logic personally. Not that I don't agree with it, just that I'm willing to sacrifice financially in exchange for the satisfaction of owning our home.