Matt, I appreciate you reaching out. Especially since you're a long-established contributor to the world of tech using your real name and I'm using a week-old moniker representing a Mexican food product. Some history:
I'm somewhat bedazzled by Reddit's /r/personalfinance group. It's a weird mix of debt support group, FICO score obsessive-compulsives, bots posting FAQ entries, and what appears to be 14 year olds who watch that guy who yells on the finance channel instead of doing their algebra homework repeating the same boilerplate advice over and over regardless of what the panicked, desperate OP declares is his unique financial situation and needs.
Between that, pg's insane essay yesterday on "being mean", and a discussion with a knucklehead here last week who didn't understand dilution or liquidity, your post caught me at an odd time.
My first problem with your post is that it lacks context. It goes from "gee shucks here's some dumb shit I did" to vague recommendations straight out of elementary school economics to "choose a credit union -- but not the one I chose" to suddenly talking about donor-assisted charity funds and maintaining your own mini-index fund by purchasing 75 stocks. You also use the phrase "sunshine tax" referring to weather just to make sure it's a big ol' swirl of mixed metaphors.
As someone who's only previously read your stuff when you're outlining guidelines (and teasing vague hints) of how not to piss off Googlebot, it's a little weird.
It's the same problem /r/personalfinance faces. It's not clear how old you are, where you live, what your marital/child situation is, what your health is, what your parent's health is, what your values are, or just how fucking rich you are. I don't blame you for not saying it and I don't want to know. But without that, you're a talking head spouting finance with no track record and no background, and you're saying nothing that I haven't heard from that blonde lady with the fancy haircut or the Reddit finance bot.
It's the blogger's curse, one I find myself asking whenever I start clicking around the web: why did you write this post, who the hell are you, and why should I take you seriously?
You lost your shirt on Cisco, you nearly lost it all with unsecured notes, and now you're giving me advice about securities? Um, ok. Paul Graham's doing his Dale-Carnegie-On-A-Bumper-Sticker schtick, I guess why not?
Context aside, some specifics relating to your article:
1. You are probably a bad stock picker
Should read "I am a bad stock picker." Overlaps with "just buy an index." Also, for support you link to an article written by someone who was banned for life from the securities industry.
2. No one cares about your money as much as you do
No one cares about your health as much as you do either. That doesn't mean you shouldn't visit a doctor when there's a lump in your ballsack. The world isn't melting and there are trustworthy financial organizations. Though I'd sure love to know why Google Finance sucks so hard. Financial news is a bot-filled hellhole, and given its highly keyworded nature with ticker symbols included, Google still insists on showing me blurbs from an Oregon utility (Portland General electric company) instead of GE, the 9th largest corporation on the planet. Nice scripts, dude. Reminds me of the time Google Translate autodetected Gesundheit as Spanish.
3. Wall Street is not your friend
This is a "hard won" lesson for you? How exactly were you maimed by the lack of regulation on Wall Street? You weren't even holding securities and you still made out okay. Also... capitalism? Zero sum? This is news? Sounds like rhetoric to me.
4. Think about working for equity vs. salary
Series A pinch, plenty of signs of a bubble ready to burst, interest rates ready to rise and suck the dumb money out of the Valley, energy prices in turmoil, housing still weak, and you're suggesting people dive into a startup in lieu of salary ("versus") in December, 2014 in order to retire? Let's meet back in 5 years and see how that worked out, deal?
5. Prefer index funds
Fascinating. 50/50 stock/bond split you say? And a plug for Vanguard LifeStrategy? Did you really just say "diversify but watch out for fees"in 339 words and slip a brand in? What is this, BuzzFeed? And... "Prefer"? Why? Versus what? And did you just link to that shitty site run by the guy banned for life from the securities industry again? Yes, yes you did.
6. Prefer credit unions over banks
"Wall Street is like [sic] carnival sideshow designed to separate you from your money." Really, dude? Half the credit unions in the US have less than $20 million in assets. Call me weird but I'd like my bank to be worth more money than I am. Deposit a couple six figure checks and you'll learn fast where service comes from at even the shittiest Bank of America branch. They'll give you more than lollipops. And, bonus: they can afford to make an Android app. Credit unions are great, except when they suck. Check yours, read the fine print, then consider that getting direct deposit to the bank that has ATMs everywhere might work out just the same on fees and better interest rates on savings to boot. And with an Android app!
7. Prefer Vanguard over almost anyone else
"I consider them one of the only companies on your side in the financial world." What an odd endorsement. Have you exhaustively researched the other discount brokers and their services? E-trade for individual 401ks? Schwab for low-deposit requirements across the board, extensive checking/banking options (varies by state)? Chase/Wells Fargo for HSAs? A not insane recommendation would be "use Vanguard as a baseline, they're tough to beat." And maybe keep your financial industry ethical intuition to yourself?
8. You probably don’t need a “assets under management” financial advisor
Another dubious section but CLEARLY should refer to the need for a tax advisor and/or estate planner. Two posts upthread I'm arguing with a guy who doesn't know how interest is taxed. Nobody gets this shit right and .25-.5% for a few years (especially when you're starting out) might be worth it. As for your well-earned phobia about outsiders touching your money, perhaps we could compromise? Trust but verify, perhaps? And maybe "don't get your advice on the internet" -- oops, isn't that pretty much what Scott Adams says in your first paragraph?
9. Consider municipal bonds
No discussion of risk. No discussion of how to compute effective tax rate.
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I realize this is harsh but I just don't understand why you woke up with a belly full of turkey and decided to become Suze Ortman. If you wanted to provide anecdotes and share mistakes you made, go for it. But when you turned the corner into being "an authority" on such a huge, complex beast that affects everyone in incredibly subtle, different ways -- you lost me.