Search found 978 matches

by ryman554
Thu May 24, 2018 8:33 am
Forum: Investing - Theory, News & General
Topic: Withdrawal Rates – Part 24: Flexibility Myths vs. Reality
Replies: 93
Views: 9316

Re: Withdrawal Rates – Part 24: Flexibility Myths vs. Reality

Finally, I'm a financially flexible person. All of my life, I've adapted my expenses to my income. That's what most people do; it's nothing unusual. People with high income tend to spend more than people with low income. So, if really bad markets happen during my retirement, I'll revisit my lifesty...
by ryman554
Wed May 23, 2018 9:12 am
Forum: Investing - Theory, News & General
Topic: What are downsides of ESPP @ 15% discount ?
Replies: 41
Views: 2670

Re: What are downsides of ESPP @ 15% discount ?

Hmm, it looks like each answer in this chain is off by at least a little, but I think that ryman554 is the closest. Correcting the Qualifying Disposition case: Compensation income is the lesser of - 15% of the Grant date price - Sales price minus Purchase price (but not less than 0) It looks like i...
by ryman554
Wed May 23, 2018 9:04 am
Forum: Investing - Theory, News & General
Topic: What are downsides of ESPP @ 15% discount ?
Replies: 41
Views: 2670

Re: What are downsides of ESPP @ 15% discount ?

3. The GAIN of the stock is long-term or short-term if HELD over more than a year, and is above the basis, regardless of qualifying or disqualifying distributions. In order for it to be a long-term GAIN it must be HELD over more than a year from PURCHASE and also be held for more than 2 years from ...
by ryman554
Tue May 22, 2018 6:38 pm
Forum: Investing - Theory, News & General
Topic: What are downsides of ESPP @ 15% discount ?
Replies: 41
Views: 2670

Re: What are downsides of ESPP @ 15% discount ?

3. The GAIN of the stock is long-term or short-term if HELD over more than a year, and is above the basis, regardless of qualifying or disqualifying distributions. In order for it to be a long-term GAIN it must be HELD over more than a year from PURCHASE and also be held for more than 2 years from ...
by ryman554
Tue May 22, 2018 2:38 pm
Forum: Investing - Theory, News & General
Topic: What are downsides of ESPP @ 15% discount ?
Replies: 41
Views: 2670

Re: What are downsides of ESPP @ 15% discount ?

rymann554 - We weren't saying the same thing and you ALSO missed my point and made incorrect statements above (shown in BOLD). The Capital gain being short term and long term is NOT just dependent purely upon the PURCHASE date (contrary to discussions in these threads and what you stated above) but...
by ryman554
Tue May 22, 2018 8:53 am
Forum: Personal Finance (Not Investing)
Topic: Employee stock - Brokerage account suggestion
Replies: 7
Views: 603

Re: Employee stock - Brokerage account suggestion

The best place to park those stocks is to sell them immediately in the lowest cost way. This may be after transferring in kind to a place like TD, or it may be at your current spot. That is where I have a concern. Will I not be subject to capital gains tax if I sell these stocks? I am not sure if I...
by ryman554
Tue May 22, 2018 8:41 am
Forum: Investing - Theory, News & General
Topic: What are downsides of ESPP @ 15% discount ?
Replies: 41
Views: 2670

Re: What are downsides of ESPP @ 15% discount ?

If you are in a high tax bracket (say, 32% or higher), it may be worth looking at extending the rotation period to 1 year in order to sell at long term capital gains (LTCG) rate. No, not really. The 15% discount (or whatever discount you get) at vesting is always taxed as ordinary income. Only the ...
by ryman554
Tue May 22, 2018 8:16 am
Forum: Investing - Help with Personal Investments
Topic: Frontloading 401k Mistake
Replies: 27
Views: 2239

Re: Frontloading 401k Mistake

Perfect! Thanks everyone! Not to make this any more complicated, but can I /what if I roll this over to an IRA now? Would I be able to remove the excess contribution myself at year end? Or is that just making the mess stickier?? For the love of all that is good, please don't do this. You have to ge...
by ryman554
Tue May 22, 2018 8:14 am
Forum: Investing - Help with Personal Investments
Topic: Frontloading 401k Mistake
Replies: 27
Views: 2239

Re: Frontloading 401k Mistake

Guys, just think it over will you? If one could reverse 401K contributions, wouldn't everybody do that when the market drops later in the year? You ask your company to give back all of your contribution IN DOLLARS contributed and then put it back again next day? Does legitimate excess contribution ...
by ryman554
Mon May 21, 2018 9:02 am
Forum: Personal Finance (Not Investing)
Topic: Employee stock - Brokerage account suggestion
Replies: 7
Views: 603

Re: Employee stock - Brokerage account suggestion

What is the best place to park these stocks? The best place to park those stocks is to sell them immediately in the lowest cost way. This may be after transferring in kind to a place like TD, or it may be at your current spot. Is TD Ameritrade the best brokerage account? Is there a better alternati...
by ryman554
Mon May 21, 2018 8:43 am
Forum: Investing - Theory, News & General
Topic: What are downsides of ESPP @ 15% discount ?
Replies: 41
Views: 2670

Re: What are downsides of ESPP @ 15% discount ?

I have the same type of plan. There is no downside, short of the stock price crashing massively on the day the offering closes... Just put in a sell @ market order before market open the day the shares release, take the money and run :) Yes, and every single time the ESPP stock has this nasty ilttl...
by ryman554
Mon May 21, 2018 8:28 am
Forum: Investing - Theory, News & General
Topic: Don't leave your non-spouse heirs TIRAs with basis, unless you hate them!
Replies: 92
Views: 8257

Re: Don't leave your non-spouse heirs TIRAs with basis, unless you hate them!

Of course if your 401(k) won't accept incoming rollovers from former employees, then there's nothing to be done. But if the plan does, and the amounts at stake are big enough, it might still be worth doing. My 401(k) will accept incoming rollovers from former employees (aka older rollover IRA) but ...
by ryman554
Fri May 18, 2018 9:04 am
Forum: Personal Finance (Not Investing)
Topic: Best use of inherited assets to get to retirement soon
Replies: 7
Views: 1273

Re: Best use of inherited assets to get to retirement soon

+1 for selling the rental. You're only getting 5% on it, and you haven't talked about maintenance/new roof. Plus, you're no longer doing business with family. That's never a good idea. Have your relative buy you out or force a sale. I am, additionally, somewhat uneasy on your 2.15M to 2.5M to 3M ass...
by ryman554
Fri May 18, 2018 8:37 am
Forum: Investing - Help with Personal Investments
Topic: Cashless exercise of NSO vs ISO
Replies: 7
Views: 558

Re: Cashless exercise of NSO vs ISO

OP said cashless exercise, which can only be done as a cashless exercise and immediate sale. There’s no such thing as a cashless exercise and hold thus an ISO disqualifying disposition is a certainty. The money to buy and hold the shares must come from somewhere. Isn't there a "sell to cover" optio...
by ryman554
Thu May 17, 2018 9:04 am
Forum: Investing - Help with Personal Investments
Topic: Cashless exercise of NSO vs ISO
Replies: 7
Views: 558

Re: Cashless exercise of NSO vs ISO

If by cashless exercise you mean cashless exercise and sale, then there is little difference between ISOs and NSOs. The big differences arise when you exercise options one calendar year and then sell the shares in another year. I was under the impression that the taxation of both were exactly the s...
by ryman554
Thu May 17, 2018 8:52 am
Forum: Investing - Help with Personal Investments
Topic: Urgent: escrow situation in bay area
Replies: 50
Views: 2769

Re: Urgent: escrow situation in bay area

I think your mortgage is high for your salary, but you can make it work. I did something very similar to you back in 2010, with similar to lower salary than you. I have a slightly higher salary than you, and I will tell you that 960k mortgage, you are paying $5000 (or more) a month in P&I. You will ...
by ryman554
Tue May 15, 2018 8:39 am
Forum: Investing - Theory, News & General
Topic: Withdrawal Rates – Part 24: Flexibility Myths vs. Reality
Replies: 93
Views: 9316

Re: Withdrawal Rates – Part 24: Flexibility Myths vs. Reality

BH rules don't allow to speculate on that but individuals are welcome to keep that in mind. Any other ideas to make the retirement expenses 100% secure and never ever seeing portfolio going down? I am wondering what do I really have to do keep portfolio going up even when the markets are going down...
by ryman554
Fri May 11, 2018 8:58 am
Forum: Investing - Theory, News & General
Topic: Withdrawal Rates – Part 24: Flexibility Myths vs. Reality
Replies: 93
Views: 9316

Re: Withdrawal Rates – Part 24: Flexibility Myths vs. Reality

I really like the work that ERN has done in this field. Nevertheless, I think his analysis here is overly pessimistic. It's widely known that the '4% rule' was tailored for 30 year retirements, and longer periods than 30 years need a lower starting withdrawal rate. Most of those who have done any r...
by ryman554
Fri May 11, 2018 8:37 am
Forum: Investing - Help with Personal Investments
Topic: When to exercise options at public company?
Replies: 6
Views: 563

Re: When to exercise options at public company?

In case this isn't clear, the value of the options grant is always taxed as ordinary income, no matter the holding period. It is only the increase of the grant value that would be taxed at long term CG rates if you hold long enough. Knowing that, there is no reason to exercise before expiration. If...
by ryman554
Thu May 10, 2018 8:35 am
Forum: Investing - Help with Personal Investments
Topic: Newby to this forum: do i have enough?
Replies: 43
Views: 7512

Re: Newby to this forum: do i have enough?

It's delusional to think that clipping coupons is part of the path to wealth accumulation when someone is making $650,000 a year. Self-identifying as 'frugal' here may make you feel good, but it stretches the limits of credulity. I currently make about $1,200,000/year on a business that collects ab...
by ryman554
Wed May 09, 2018 8:19 am
Forum: Investing - Help with Personal Investments
Topic: ESPP taxing rules, to hold or not to hold
Replies: 28
Views: 1978

Re: ESPP taxing rules, to hold or not to hold

I kept my ESPP stocks so far (two quarters). I just recently learned ESPP shares have to be hold for more than a year after the purchase date AND more than two years after the beginning of the offering period then any profit above the gain from the discount will be taxed at capital gains tax rates....
by ryman554
Thu May 03, 2018 8:42 am
Forum: Investing - Theory, News & General
Topic: Trinity Study updated to 2018
Replies: 156
Views: 15723

Re: Trinity Study updated to 2018

The past performance of a 50/50 AA looks pretty good. Not to me, it doesn't. Yes, it has the most 100%. But the dropoff in success is rapid as you to to higher WR or, more importantly, longer terms. That tells me that I am more susceptible to "unexpected expenses" for 50/50, as you would expect fro...
by ryman554
Thu May 03, 2018 8:28 am
Forum: Investing - Help with Personal Investments
Topic: Questions preparing for an ISO Cashless Exercise
Replies: 1
Views: 215

Re: Questions preparing for an ISO Cashless Exercise

I wouldn't file estimated taxes, as long as you didn't have a big tax year last year. Given this is a one-off(?), get you money and put 50% in the bond account and use it to pay taxes next year. Increase your current W-2 withholding to meet 110% of last years tax obligations so you are in the safe h...
by ryman554
Thu May 03, 2018 8:20 am
Forum: Investing - Help with Personal Investments
Topic: Mega-backdoor Roth with Fidelity BrokerageLink account
Replies: 1
Views: 226

Re: Mega-backdoor Roth with Fidelity BrokerageLink account

I need some help on the subject: My 401K plan is with Fidelity and I recently opened a BrokerageLink account thru the 401K account. My pre-tax contributions go to the 401K account first and then I transfer them to the BrokerageLink account to invest in Fidelity funds that are not available in my 40...
by ryman554
Tue May 01, 2018 5:59 pm
Forum: Investing - Help with Personal Investments
Topic: OrderingRules mega backdoor Roth
Replies: 8
Views: 609

Re: OrderingRules mega backdoor Roth

Maybe this helps (these are smaller than above. I was counting my wife's Roth above. This is just my Roth): 2014 - Roth IRA opened, no contributions 2015 - 11,000 non-taxable conversion, 603.29 taxable conversion (earnings before backdoor) [starts 5 year clock] 2016 - 21,852.70 non-taxable conversi...
by ryman554
Mon Apr 30, 2018 8:51 am
Forum: Investing - Theory, News & General
Topic: How does one optimally prepare for predictable, lumpy expenses while consistently investing?
Replies: 22
Views: 2053

Re: How does one optimally prepare for predictable, lumpy expenses while consistently investing?

I, too, self-escrow my $13k property tax payment at $1000/month.

The savings account also functions as a emergency fund, of a sort, which I am slowly drawing down as my assets increase.
by ryman554
Mon Apr 30, 2018 8:41 am
Forum: Investing - Help with Personal Investments
Topic: ESPP taxing rules, to hold or not to hold
Replies: 28
Views: 1978

Re: ESPP taxing rules, to hold or not to hold

I have been enrolled in my company's ESPP program. We have quarterly offering period, where we can invest 15% of our salary to stock, and purchase it at the end of the quarter with a 10% discount. ... What do other ESPP holders do? I know bogleheads mindset always avoids single stocks, and I do as ...
by ryman554
Fri Apr 27, 2018 9:04 am
Forum: Personal Finance (Not Investing)
Topic: Cashing out of the Bay Area
Replies: 84
Views: 10355

Re: Cashing out of the Bay Area

Having been born and raised in the Bay Area - and left it - at age 46 - I'd say the weather is boring. If you like every day to be pretty much the same - then that is the Bay Area. I didn't know I loved weather so much until I left - wow four seasons - monsoons - dramatic rain/thunderstorms - light...
by ryman554
Fri Apr 27, 2018 8:55 am
Forum: Personal Finance (Not Investing)
Topic: Potential future events screwing up current Backdoor Roth?
Replies: 4
Views: 466

Re: Potential future events screwing up current Backdoor Roth?

Hypothetical question Young NYS resident in top marginal tax bracket, If I have set up my Backdoor Roth this year what future events could have bad tax consequences? How about 1. Switching jobs and my new company’s 401K options are so bad I would want to spin off my current 401K into a IRA to preve...
by ryman554
Mon Apr 16, 2018 9:02 pm
Forum: Personal Finance (Not Investing)
Topic: If home prices decline but mortgage rates keep rising
Replies: 25
Views: 2819

Re: If home prices decline but mortgage rates keep rising

Be sure to play with the actual numbers. For example for a 30 year loan; $100,000 with a 4% mortgage has a payment of $477 $80,000 with a 6% mortgage has a payment of $480 These are not adjusted for inflation but even if you could predict the future it might not make as much difference as you might...
by ryman554
Mon Apr 16, 2018 2:46 pm
Forum: Investing - Help with Personal Investments
Topic: What to do about withdrawal this year if market doesn't go up?
Replies: 32
Views: 3045

Re: What to do about withdrawal this year if market doesn't go up?

True, my account rose enough last year to cover this year. Is that what people did in 2015, it comes from the previous year(s)? Ok. Have about 1.2 million, not including the pension - so the average dividend gets me $24k leaving about 20k more to pull. No problem, that comes from last year's growth...
by ryman554
Mon Apr 16, 2018 2:38 pm
Forum: Investing - Help with Personal Investments
Topic: What to do about withdrawal this year if market doesn't go up?
Replies: 32
Views: 3045

Re: What to do about withdrawal this year if market doesn't go up?

Isn't the theory that it doesn't matter what the market does, you just simply take out your 4% per year (or whatever you've decided as your SWR), and that 4% will be a bigger or smaller amount based on what the market did? Typically, when people talk about a safe withdrawal rate strategy, they are ...
by ryman554
Sun Apr 08, 2018 3:10 pm
Forum: Personal Consumer Issues
Topic: VHCOL Home Buying Advice (Bay Area, where else?)
Replies: 65
Views: 5138

Re: VHCOL Home Buying Advice (Bay Area, where else?)

HRPennypacker wrote:
Sun Apr 08, 2018 12:52 pm
I moved to SV from Seattle, kicking and screaming, and still travel back for work every other week. I can't handle the weather up there anymore.
Huh. That's funny. I can't handle the weather in SV anymore and would love to be in a place as grey and crappy as Seattle.....
by ryman554
Fri Apr 06, 2018 9:43 am
Forum: Investing - Help with Personal Investments
Topic: Large Single Stock Position - Can't Sell - Retirement Account
Replies: 45
Views: 3203

Re: Large Single Stock Position - Can't Sell - Retirement Account

Why do we have AA? To create a efficient portfolio - to create the best risk adjusted return as possible. One way would be to crave it out into its own asset class. A more standard way is to give the asset a haircut. Illiquid and concentrated positions can be given a haircut in value of 20% to 60% ...
by ryman554
Fri Apr 06, 2018 9:23 am
Forum: Personal Finance (Not Investing)
Topic: How does one adjust salaries to account for housing costs when considering a move?
Replies: 24
Views: 1475

Re: How does one adjust salaries to account for housing costs when considering a move?

Step 1 is to focus on cash flow. You know where you are now. Figure out what it's going to be for the new place. You are somewhat doing it with the mortgage difference. Do it with taxes (federal, state, property) and all the rest of the stuff. There are a lot of cost-of-living calculators around, us...
by ryman554
Fri Apr 06, 2018 8:42 am
Forum: Investing - Help with Personal Investments
Topic: Large Single Stock Position - Can't Sell - Retirement Account
Replies: 45
Views: 3203

Re: Large Single Stock Position - Cant Sell - Retirement Account

What is the plan if you die? Will your heirs have some hassle with this? For personal reasons though, I would consider this holding a non-saleable. As a percent of total assets it is under 3%. You are legally able to sell the thing. And it's not 3%, it's 10%. This makes absolutely no sense. I can t...
by ryman554
Thu Apr 05, 2018 8:59 am
Forum: Investing - Theory, News & General
Topic: What can we learn from secret millionaires.
Replies: 93
Views: 16896

Re: What can we learn from secret millionaires.

I can also tell you that one attribute of a secret millionaire is that they understand very well that a million dollars isn't a lot of money. Not a lot of money in what context? The median individual income in the US is around $26k/yr so I would think that an amount of money that produces over 150%...
by ryman554
Thu Apr 05, 2018 8:51 am
Forum: Investing - Help with Personal Investments
Topic: Backdoor Roth - contributed to Roth directly
Replies: 9
Views: 972

Re: Backdoor Roth - contributed to Roth directly

Excess contributions can be withdrawn either before the extended due date (10/15/2017 for a 2016 excess) with earnings per Sec 408(d)(4) or AFTER the due date without earnings per Sec 408(d)(5). Both sections are copied below. When withdrawn after the due date, the 6% excise tax is due for each yea...
by ryman554
Thu Apr 05, 2018 8:46 am
Forum: Investing - Help with Personal Investments
Topic: HELP: I think I messed up my Roth 401K rollover
Replies: 5
Views: 360

Re: HELP: I think I messed up my Roth 401K rollover

I think I just effed up big time.... I have been contributing to a Roth 401k (5% company match) for the last four years (I’m 27). I recently started a new job and initiated a direct rollover from my old Roth 401K into my Roth IRA that I hold at Fidelity. I just learned that apparently employer matc...
by ryman554
Wed Apr 04, 2018 8:51 am
Forum: Personal Finance (Not Investing)
Topic: Reversing a corrective distribution made in error
Replies: 2
Views: 185

Re: Reversing a corrective distribution made in error

There may or may not be. Likely not. Whatever the case, I can confidently tell you that you will be spending more than your ex-company match you have lost as valued in time and aggravation trying to get the two companies to do what you want. You are in compliance in IRA regulations now. Just go forw...
by ryman554
Wed Apr 04, 2018 8:30 am
Forum: Investing - Help with Personal Investments
Topic: After tax rollover issues
Replies: 30
Views: 1260

Re: After tax rollover issues

Now it appears if I want to convert to roth, you have to convert the entire IRA (if im understanding things correctly), and I cant afford that tax hit. I'm not sure where you got the idea that you have to convert the entire IRA. That is simply not true. You can convert whatever amount you want, but...
by ryman554
Tue Apr 03, 2018 8:20 am
Forum: Investing - Help with Personal Investments
Topic: After tax rollover issues
Replies: 30
Views: 1260

Re: After tax rollover issues

no... its right. Supplement is a term used to separate what is being contributed past the employer matching contribution. I noticed the taxable amount in the roth as well... I can only assume its the contribution part vs gains. Probably in the event I made an early withdrawal. Supplimental is a ver...
by ryman554
Tue Apr 03, 2018 8:12 am
Forum: Investing - Help with Personal Investments
Topic: After tax rollover issues
Replies: 30
Views: 1260

Re: After tax rollover issues

It appears that Vanguard did what you told them to do but it was not what you thought you told them to do. Or it was not what you assumed would happen. If you don't agree with that assessment, you need to fight your battle up the line at Vanguard. If you said to "put xxx into Roth IRA" and they did...
by ryman554
Mon Apr 02, 2018 6:33 pm
Forum: Investing - Help with Personal Investments
Topic: After tax rollover issues
Replies: 30
Views: 1260

Re: After tax rollover issues

We can't really understand what happened without the other numbers. How much was in traditional 401k? How much was in Roth 401k? How much was in the after-tax account? How much of that was from after-tax contributions? It is hard to figure out if you asked your employer for the wrong thing, if your...
by ryman554
Mon Apr 02, 2018 3:45 pm
Forum: Investing - Help with Personal Investments
Topic: After tax rollover issues
Replies: 30
Views: 1260

Re: After tax rollover issues

OK, lets use the correct terminology. I will assume you left your job. You had balances (which custodian?) in 401(k) in three categories: 1. regular pre-tax 401(k) 2. ROTH 401(k) 3. After-tax 401(k) -> note, many plans do not have this. I am assuming that yours was a special plan and you wanted to c...
by ryman554
Sun Apr 01, 2018 4:35 pm
Forum: Personal Finance (Not Investing)
Topic: 4% SWR - planning for worst, hoping for better
Replies: 37
Views: 2246

Re: 4% SWR - planning for worst, hoping for better

Yes and I think the 4% rule there's some very high probability that you end up with more money after 30 years than before it, even with regular withdrawing, and some incredibly low probability of being down to a small percentage of the portfolio. Well, yes. Equities get, what, ~7-8% real? Bonds get...
by ryman554
Sun Apr 01, 2018 3:44 pm
Forum: Investing - Help with Personal Investments
Topic: Total Market Index in Both 401K & Taxable
Replies: 6
Views: 629

Re: Total Market Index in Both 401K & Taxable

That's really up to you.

If you want to allocate based on total market cap, then:

US and ex-US is about 50:50.

S&P 500 is about 80% of total US market.

Use that information how you will.
by ryman554
Sat Mar 31, 2018 1:51 pm
Forum: Investing - Help with Personal Investments
Topic: 401k Loan but odd conundrum!
Replies: 13
Views: 1050

Re: 401k Loan but odd conundrum!

I know those rules but am seeking more specifically the answers to said questions in the original post. I would voiie for the amounts to offset each other and go elsewhere anew. No problem with that at all as I am indebted by that accord . I would prefer to know if there are tertiary fees in those ...
by ryman554
Fri Mar 30, 2018 9:23 am
Forum: Personal Finance (Not Investing)
Topic: How Do You Value Your Home for Net Worth Purposes?
Replies: 150
Views: 9594

Re: How Do You Value Your Home for Net Worth Purposes?

I include home value in my net worth. I use a conservative value and also subtract 6% for my cost to sell it. And I put my mortgage loan balance in my liability section. I for one, think that net worth is the most important financial measurement that I track. It is the purest measurement of my fina...