Search found 80 matches

by NewMoneyMustBeSmart
Sat Oct 19, 2019 3:22 pm
Forum: Personal Finance (Not Investing)
Topic: sibling and revocable living trust
Replies: 14
Views: 1282

Re: sibling and revocable living trust

Here's how I would think of it.

Is he of sound mind? If so, try to persuade him. But you can't make a horse drink, you can just lead it to water.

If he is not of sound mind, then work with the system in as much control as you can exercise, to get appointed responsible for him and help him.
by NewMoneyMustBeSmart
Sat Oct 19, 2019 12:21 pm
Forum: Personal Consumer Issues
Topic: 2019 year end car buying experience
Replies: 24
Views: 2767

Re: 2019 year end car buying experience

When you say you're "getting quotes", those are "out the door" quotes with all costs included, right? I went through this process about a month ago to 5 dealers (same manufacturer) & told them to give me "your best out the door price". After I sent an email letting the dealers know that they did no...
by NewMoneyMustBeSmart
Sat Oct 19, 2019 12:14 pm
Forum: Personal Consumer Issues
Topic: 2019 year end car buying experience
Replies: 24
Views: 2767

Re: 2019 year end car buying experience

Sorry to start this and run, but I started shopping or a new 2019 vehicle. I will fill in the details tomorrow, but if you are interested in purchasing or leasing a car, the dealers are ready to make great deals. You just have to play hardball with them and do their silly dance and get 3 quotes. So...
by NewMoneyMustBeSmart
Thu Oct 17, 2019 3:10 pm
Forum: Personal Investments
Topic: How to handle 5M capital gain (post-IPO)
Replies: 85
Views: 6654

Re: How to handle 5M capital gain (post-IPO)

And unlike the OP, once I hit my magic number, I'm dropping off the face the Earth and vanishing into the ether. I ain't stickin' 'round fer nuthin'. 10 years ago I hired a wealthy friend who wanted to help me with an interesting problem. Someone told him, "If I had your money, I'd be on a beach so...
by NewMoneyMustBeSmart
Thu Oct 17, 2019 12:59 pm
Forum: Personal Investments
Topic: How to handle 5M capital gain (post-IPO)
Replies: 85
Views: 6654

Re: How to handle 5M capital gain (post-IPO)

REGRET MINMIZATION Many of the RIAs I've spoken with who have managed money for years (>10 y) say that a lot of tech folks have regretted selling everything to watch the stock go up 200% in 1-3 years. So, if you follow this school of thought, perhaps keep some long term. The human mind is fascinati...
by NewMoneyMustBeSmart
Thu Oct 17, 2019 12:54 pm
Forum: Personal Investments
Topic: How to handle 5M capital gain (post-IPO)
Replies: 85
Views: 6654

Re: How to handle 5M capital gain (post-IPO)

If I understand correctly, you 83b-ed or purchased your stock earlier, and now own it outright. To clarify, I purchased restricted stock shares in 2008 (not RSU's, I purchased the shares outright). All the gain is long term, with a nearly zero cost basis. Now that the stock is publicly traded, the ...
by NewMoneyMustBeSmart
Thu Oct 17, 2019 7:42 am
Forum: Personal Finance (Not Investing)
Topic: learning about consulting side job - taxes, etc.
Replies: 6
Views: 686

Re: learning about consulting side job - taxes, etc.

I am considering taking an ongoing side position as a consultant/independent contractor, which has been offered to me by a specific company. This is allowable by my current employer, with time limits. I haven't had such a position before and would like to know what I should consider and learn befor...
by NewMoneyMustBeSmart
Thu Oct 17, 2019 7:17 am
Forum: Personal Investments
Topic: How to handle 5M capital gain (post-IPO)
Replies: 85
Views: 6654

Re: How to handle 5M capital gain (post-IPO)

If I understand correctly, you 83b-ed or purchased your stock earlier, and now own it outright. I don’t believe OP made an 83-b election for the shares held as OP is talking about owing federal taxes on the gain and not just state taxes. Not sure I agree but you're probably right. When I am given o...
by NewMoneyMustBeSmart
Thu Oct 17, 2019 7:11 am
Forum: Personal Finance (Not Investing)
Topic: Company being acquired - severance strategy?
Replies: 23
Views: 2044

Re: Company being acquired - severance strategy?

And I disagree with taking the vacation time if you have a set amount of time off. That gets paid out on termination should you be terminated. Payment of earned PTO is dependent on state and company policy. In CA it's true. https://www.patriotsoftware.com/payroll/training/blog/pto-payout-laws-by-st...
by NewMoneyMustBeSmart
Thu Oct 17, 2019 7:04 am
Forum: Personal Investments
Topic: How to handle 5M capital gain (post-IPO)
Replies: 85
Views: 6654

Re: How to handle 5M capital gain (post-IPO)

If you die with too much money, you basically lost the game - you spent more time on your money than was actually justified. Damn good point. Dying with more money that you need to pass on to your heirs/charities is like over-withholding. Unfortunately, some of us have the puritanical cultural mind...
by NewMoneyMustBeSmart
Thu Oct 17, 2019 7:02 am
Forum: Personal Investments
Topic: How to handle 5M capital gain (post-IPO)
Replies: 85
Views: 6654

Re: How to handle 5M capital gain (post-IPO)

I was told by someone that there are really two sets of rules that govern what you can do with your stock. Recommend you check with an attorney to make sure: 1. SEC Rules - prevent insider trading and deal with Material Non-Public Information 2. Company Rules - usually things like can't short, can't...
by NewMoneyMustBeSmart
Thu Oct 17, 2019 7:00 am
Forum: Personal Investments
Topic: How to handle 5M capital gain (post-IPO)
Replies: 85
Views: 6654

Re: How to handle 5M capital gain (post-IPO)

I just want to echo the recommendations to look into options as a way to hedge to avoid selling it all in one year. See: https://www.investopedia.com/articles/stocks/11/diversify-stock-position.asp Thanks for the suggestion (and link, I hadn't found that page). I will consider a couple (simpler) op...
by NewMoneyMustBeSmart
Thu Oct 17, 2019 6:56 am
Forum: Personal Investments
Topic: How to handle 5M capital gain (post-IPO)
Replies: 85
Views: 6654

Re: How to handle 5M capital gain (post-IPO)

A company that I worked for when it was a very early stage startup had an IPO earlier this year. I've been holding restricted stock that is now liquid, and worth ~4.8M. After the IPO lock-out expired, I sold 30% to lock in some gain (and help myself sleep at night), and I'm trying to decide what to...
by NewMoneyMustBeSmart
Tue Oct 15, 2019 5:06 pm
Forum: Personal Finance (Not Investing)
Topic: Safe Harbor through Withholding
Replies: 22
Views: 873

Re: Safe Harbor through Withholding

HomeStretch wrote:
Tue Oct 15, 2019 3:11 pm
Agree about talking with your CPA for best guidance for 2019 and advice on how to set your withholdings for 2020.
Both of the firms I use are super busy w/ end of quarterly estimate work, so I just have you folks today :)
by NewMoneyMustBeSmart
Tue Oct 15, 2019 4:17 pm
Forum: Personal Finance (Not Investing)
Topic: Safe Harbor through Withholding
Replies: 22
Views: 873

Re: Safe Harbor through Withholding

Spirit Rider wrote:
Tue Oct 15, 2019 3:19 pm

I would first check and see what the minimal withholding is choosing the optimal safe harbor. Given the amounts involved there is no chance it is option 1. above
If a person makes $300k salary and sells $15M of LTCG stock, is #1 likely the least total amount?
by NewMoneyMustBeSmart
Tue Oct 15, 2019 4:15 pm
Forum: Personal Finance (Not Investing)
Topic: Safe Harbor through Withholding
Replies: 22
Views: 873

Re: Safe Harbor through Withholding

My CPA recommended I should withhold an extra $60k from my paychecks to reach safe harbor this year. According to this article (I can't immediately find the canonical IRS document) https://wallethacks.com/estimated-taxes-due-dates-safe-harbor-rules/ : The estimated safe harbor rule has three parts:...
by NewMoneyMustBeSmart
Tue Oct 15, 2019 2:55 pm
Forum: Personal Finance (Not Investing)
Topic: Safe Harbor through Withholding
Replies: 22
Views: 873

Re: Safe Harbor through Withholding

+1 on having the additional $20k taxes withheld from other income (like an IRA distribution or spouse’s paycheck) or, if additional withholdings are not possible, making estimated tax payment. I don't have other income. Unless maybe when I sell stock this year I tell the brokerage to withhold, but ...
by NewMoneyMustBeSmart
Tue Oct 15, 2019 2:53 pm
Forum: Personal Finance (Not Investing)
Topic: Safe Harbor through Withholding
Replies: 22
Views: 873

Re: Safe Harbor through Withholding

Publication 505 (2019), Tax Withholding and Estimated Tax: "Estimated tax. If you don’t pay your tax through withholding, or don’t pay enough tax that way, you might have to pay estimated tax. People who are in business for themselves generally will have to pay their tax this way. You may have to p...
by NewMoneyMustBeSmart
Tue Oct 15, 2019 2:53 pm
Forum: Personal Finance (Not Investing)
Topic: Safe Harbor through Withholding
Replies: 22
Views: 873

Re: Safe Harbor through Withholding

anon_investor wrote:
Tue Oct 15, 2019 1:38 pm
Can't you just make an estimate tax payment before the Q4 deadline?
I thought the bucket of money for estimated tax payments is discrete and separate from the bucket of money for withholdings.

Are they the same for 'moneys withheld' purposes to make safe harbor in the first case?
by NewMoneyMustBeSmart
Tue Oct 15, 2019 2:52 pm
Forum: Personal Finance (Not Investing)
Topic: Safe Harbor through Withholding
Replies: 22
Views: 873

Re: Safe Harbor through Withholding

Not sure if this goes without saying but if you earn the money evenly throughout the year that is taxable you cannot just send a bunch of money to the IRS at the end of the year, even if you over-withhold or meet the safe harbor limits. The IRS expects you to make even payments in such a case other...
by NewMoneyMustBeSmart
Tue Oct 15, 2019 1:34 pm
Forum: Personal Consumer Issues
Topic: Doctors charging for things outside of insurance, is this Kosher?
Replies: 55
Views: 5208

Re: Doctors charging for things outside of insurance, is this Kosher?

The doctor who would be performing the procedure has charged me $275 to “keep his calendar open” for the day. I understand this as an inconvenience fee for cancelling all his appointments for the day that he likely is still scheduling. ... I’m sorry but this does not pass the smell test to me. Is t...
by NewMoneyMustBeSmart
Tue Oct 15, 2019 1:28 pm
Forum: Personal Finance (Not Investing)
Topic: Safe Harbor through Withholding
Replies: 22
Views: 873

Safe Harbor through Withholding

My CPA recommended I should withhold an extra $60k from my paychecks to reach safe harbor this year. According to this article (I can't immediately find the canonical IRS document) https://wallethacks.com/estimated-taxes-due-dates-safe-harbor-rules/ : The estimated safe harbor rule has three parts: ...
by NewMoneyMustBeSmart
Sun Oct 13, 2019 9:16 pm
Forum: Personal Investments
Topic: What’s the point of a taxable account?
Replies: 62
Views: 6457

Re: What’s the point of a taxable account?

Hey all, The more I read the forum, the more I see people bring up questions regarding taxable accounts. At age 29, I will be honest that 75% of my total portfolio is in a taxable account (vtsax), the remaining 25% in a Roth IRA. Every week deposit into my Roth IRA account, while also buying into m...
by NewMoneyMustBeSmart
Sun Oct 13, 2019 8:54 am
Forum: Personal Consumer Issues
Topic: Airline compensation
Replies: 8
Views: 1414

Re: Airline compensation

Do airlines owe compensation for flight delays over 6 hours? https://www.transportation.gov/airconsumer/fly-rights Contrary to popular belief, for domestic itineraries airlines are not required to compensate passengers whose flights are delayed or canceled. As discussed in the chapter on overbookin...
by NewMoneyMustBeSmart
Sun Oct 13, 2019 8:46 am
Forum: Personal Investments
Topic: Receiving gift of stock - the mechanics
Replies: 8
Views: 557

Re: Receiving gift of stock - the mechanics

It is not correct that the parents will pay gift tax if the gift is greater than $30,000. They will need to file a form with their federal taxes reporting the gift in the year it is made, but no tax will be due. If taxes are due, it will be when the parents have both died and then only if their est...
by NewMoneyMustBeSmart
Sun Oct 13, 2019 8:45 am
Forum: Personal Investments
Topic: Receiving gift of stock - the mechanics
Replies: 8
Views: 557

Re: Receiving gift of stock - the mechanics

[/quote] It is not correct that the parents will pay gift tax if the gift is greater than $30,000. They will need to file a form with their federal taxes reporting the gift in the year it is made, but no tax will be due. If taxes are due, it will be when the parents have both died and then only if t...
by NewMoneyMustBeSmart
Sat Oct 12, 2019 4:16 pm
Forum: Personal Finance (Not Investing)
Topic: Best Trust Company For Spendthrift Child
Replies: 13
Views: 1875

Re: Best Trust Company For Spendthrift Child

Does anyone have any trust companies they recommend or any good resources to read about the comparisons between then? I recommend Five Points Bank in Grand Island, NE. I recommend you read the book "Beyond The Grave" [1] which gives many anecdotal examples and explanations about various issues with...
by NewMoneyMustBeSmart
Sat Oct 12, 2019 4:13 pm
Forum: Personal Investments
Topic: Receiving gift of stock - the mechanics
Replies: 8
Views: 557

Re: Receiving gift of stock - the mechanics

Does it make sense for my parents to transfer the stock from wherever they have it held (I'm not super clear on where that is - they have an advisory firm who manages their investments directly) to my Vanguard account, so that when I sell it, I can easily put the proceeds into my existing investmen...
by NewMoneyMustBeSmart
Sat Oct 12, 2019 12:09 pm
Forum: Personal Consumer Issues
Topic: Do you carry your passport with you during international travel?
Replies: 107
Views: 8387

Re: Do you carry your passport with you during international travel?

Do you carry your passport with you during international travel or leave it at the hotel? What are the best practices? When traveling internationally my passport is always physically on me. Not in the hotel safe. Not in my bag. Those options are way too dangerous. Your approach is reasonable and th...
by NewMoneyMustBeSmart
Mon Oct 07, 2019 9:33 pm
Forum: Personal Investments
Topic: Desperately In Need Of Advice
Replies: 19
Views: 2877

Re: Desperately In Need Of Advice

Could you guys(experts) lead me to the right path as to what I should do with my money please?? You can and should read the boglehead wikis, specifically: https://www.bogleheads.org/wiki/Getting_started https://www.bogleheads.org/wiki/Bogleheads%C2%AE_investing_start-up_kit With $140k in savings yo...
by NewMoneyMustBeSmart
Mon Oct 07, 2019 9:26 pm
Forum: Personal Investments
Topic: Desperately In Need Of Advice
Replies: 19
Views: 2877

Re: Desperately In Need Of Advice

Sounds like a CD is a good place. A no-penalty CD if you think you will suddenly have the urge to buy a house and need the money quick. A one-year if not. Ally has one of the better no-penalty CDs. For a one year, try https://direct.comenity.com/products/certificates-of-deposit Or go to the website...
by NewMoneyMustBeSmart
Sun Oct 06, 2019 9:17 am
Forum: Personal Finance (Not Investing)
Topic: Trust Services
Replies: 202
Views: 23010

Re: Trust Services

1. Who do you currently use for investment trust services? We decided to decouple the investment and the trust services. We have a particular investment advisor (Family Friend RIA) that will manage the financial resources on our death, and a separate company that will serve as corporate trustee. Th...
by NewMoneyMustBeSmart
Sat Sep 28, 2019 4:15 pm
Forum: Personal Consumer Issues
Topic: Road Scholar: Unannounced Itinerary Changes
Replies: 26
Views: 2836

Re: Road Scholar: Unannounced Itinerary Changes

Unless their contract says they can arbitrarily change the itinerary.... Governmental travel regulations for US citizens to Cuba changed between booking and the trip. Hard to consider that "arbitrary". I'm not an expert. Quick research suggests existing plans are grandfathered. If I contract with a...
by NewMoneyMustBeSmart
Sat Sep 28, 2019 4:07 pm
Forum: Personal Finance (Not Investing)
Topic: Employer is relocating - how to be allowed to work remotely
Replies: 51
Views: 3674

Re: Employer is relocating - how to be allowed to work remotely

Does anyone have some advice on how to proceed? How do get management to accept remote work. If your management is not committed to remote work it has a low probability of success. You'll be a second class citizen as communication and work happens real time. My advice is that you prepare a list of ...
by NewMoneyMustBeSmart
Sat Sep 28, 2019 4:05 pm
Forum: Personal Investments
Topic: Investment advice
Replies: 7
Views: 511

Re: Investment advice

retiredjg wrote:
Sat Sep 28, 2019 2:44 pm

I think you should change your asset allocation because the first plan was just plain wrong.
This.
by NewMoneyMustBeSmart
Sat Sep 28, 2019 3:51 pm
Forum: Personal Consumer Issues
Topic: Road Scholar: Unannounced Itinerary Changes
Replies: 26
Views: 2836

Re: Road Scholar: Unannounced Itinerary Changes

Has anyone had a similar experience with Road Scholar? Any advice on how to approach this when they do respond? Unless their contract says they can arbitrarily change the itinerary, sue them in small claims court. If you can manage your finance you can read up on how to file and pursue. Much easier...
by NewMoneyMustBeSmart
Fri Sep 13, 2019 6:30 am
Forum: Investing - Theory, News & General
Topic: Why the stock market may continue to go up
Replies: 10
Views: 2364

Re: Why the stock market may continue to go up

I listened to Dr. Jeremy Siegel a while back, who by the way, seems to be incredibly informative and a splendid speaker. Dr. Siegel explained that historical stock market returns are 6.7% and correlate/should-be equal to the inverse of PE or Earnings/Price. He explained that the average PE over the ...
by NewMoneyMustBeSmart
Fri Sep 13, 2019 6:20 am
Forum: Personal Consumer Issues
Topic: 2019 Costco HVAC services: Good deal/issues?
Replies: 20
Views: 2318

Re: 2019 Costco HVAC services: Good deal/issues?

So my parents in SoCal are finally having to replace their 45+ year old HVAC as the A/C finally died. Has anyone used Costco for HVAC? Thoughts on using them, issues, warranty, etc? (Didn't search for older threads on topic as want up to date feedback). Thoughts are my opinions. 2 years ago one of ...
by NewMoneyMustBeSmart
Wed Sep 11, 2019 7:54 am
Forum: Personal Finance (Not Investing)
Topic: Help me out - What am I doing wrong - Job Hunt related
Replies: 70
Views: 5037

Re: Help me out - What am I doing wrong - Job Hunt related

imsomeguy wrote:
Mon Sep 09, 2019 9:54 am
... boss is a buffoon ... why all the rejections?
Probably because you anonymously call people buffoons.

Stop telling people your boss is a buffoon and have some empathy for the guy. You will likely see better opportunities for yourself at the company and at others.
by NewMoneyMustBeSmart
Wed Sep 11, 2019 7:45 am
Forum: Personal Finance (Not Investing)
Topic: Umbrella coverage a no brainer?
Replies: 13
Views: 1697

Re: Umbrella coverage a no brainer?

Is there anything that I'm missing? I signed up for $1 million umbrella and honestly am shocked more people don't do this. Seems like cheap protection against a truly catastrophic (albeit rare) situation. I think it's a no-brainer for anyone with >1M net worth or likely to have within 5 years. The ...
by NewMoneyMustBeSmart
Sun Sep 08, 2019 9:13 am
Forum: Personal Investments
Topic: Early exercising NSOs
Replies: 10
Views: 1064

Re: Early exercising NSOs

Hi Bogleheads, I am in a very small early stage startup (less than 10 people). I am thinking about leaving soon and wondering if I should early exercise the stock options I vested until now. It's been a year and a half so I have 3/8th of the total grant vested, which is about 1% of the company. The...
by NewMoneyMustBeSmart
Thu Sep 05, 2019 9:10 pm
Forum: Personal Investments
Topic: Does a FA make sense at a certain portfolio level?
Replies: 53
Views: 4286

Re: Does a FA make sense at a certain portfolio level?

That said, we have not hit a level where I feel a FA would help. We do have an estate attorney and CPA. IMO, a FA is useful if you can’t overcome behavioral issues, which can manifest at small or large portfolio size. Most FA/RIAs charge ~0.5% for >$5M. So that's $2k+/month for someone that in theo...
by NewMoneyMustBeSmart
Thu Sep 05, 2019 9:00 pm
Forum: Personal Finance (Not Investing)
Topic: How does my auto insurance look to you? Is the coverage ok?
Replies: 43
Views: 2406

Re: How does my auto insurance look to you? Is the coverage ok?

If it were me, I would probably increase the uninsured motorist coverage What would be a good amount? I sleep well at night paying $1700 for $1M auto and $3M Umbrella: Geico; 2 adult drivers, 1 car each (2 cars total) $334/year for $3M Umbrella $1530/year for Auto: $1M/$1M Bodily Injury Liability (...
by NewMoneyMustBeSmart
Thu Sep 05, 2019 8:40 pm
Forum: Personal Investments
Topic: Employer requesting refund of HSA funds
Replies: 40
Views: 3134

Re: Employer requesting refund of HSA funds

Any suggestions? A few questions... 1. What if you say no? 2. What do you want to do? 3. What if you don't meet with them? 4. Do they require your permission to pull the money out? One thing business and poker teach you is that someone else doesn't always get to tell you what to do. At the ultimate...
by NewMoneyMustBeSmart
Mon Sep 02, 2019 7:00 am
Forum: Personal Finance (Not Investing)
Topic: Investing in my Company Stock Plan (ESPP) - is it worth it?
Replies: 39
Views: 2069

Re: Investing in my Company Stock Plan (ESPP) - is it worth it?

Thoughts on these plans, or the details of this particular plan? If a company offers to double my elected investment if I hold for 5 years, I would think: 1. PRO1 - That's a great return. It's the equivalent of 14-15% interest assuming the stock is flat 2. CON1 - There is focused risk as the $1500 ...
by NewMoneyMustBeSmart
Mon Sep 02, 2019 6:52 am
Forum: Personal Consumer Issues
Topic: Did humanity ever make good Gas cans
Replies: 70
Views: 6245

Re: Did humanity ever make good Gas cans

ctuser1 wrote:
Sun Sep 01, 2019 9:15 am
Do any of you know of a gas can (as economical as possible) that can keep filling my mower, blower etc for years?
I've been joyously happy with these:

http://www.midwestcan.com/

High quality, good price (4 for $90) and easy to use without getting hands dirty.
by NewMoneyMustBeSmart
Sun Sep 01, 2019 7:43 am
Forum: Personal Finance (Not Investing)
Topic: Value of mis-claiming Child on Taxes?
Replies: 15
Views: 1731

Re: Value of mis-claiming Child on Taxes?

If he did this on his 2018 tax return, and you also did it, one of you has to file an amended return or await the IRS notice when they catch it. Since 2019's taxes have not yet been filed, this has to be on already filed taxes, no? Filing an amended return with TurboTax takes minutes. If one party ...
by NewMoneyMustBeSmart
Sun Sep 01, 2019 5:56 am
Forum: Personal Finance (Not Investing)
Topic: Value of mis-claiming Child on Taxes?
Replies: 15
Views: 1731

Re: Value of mis-claiming Child on Taxes?

It says the phaseout of the credit begins at MAGI of $400k and goes down by $50 for each $1kin earnings over that. So you can make as much as $440k and still get the tax credit, and then it goes to nothing? So if we're over $440k we should just let him have it as we can't use it? No, you lose $50 o...
by NewMoneyMustBeSmart
Sun Sep 01, 2019 5:53 am
Forum: Personal Finance (Not Investing)
Topic: Gifting to Kids with Lower Tax Rates
Replies: 13
Views: 1235

Re: Gifting to Kids with Lower Tax Rates

I would talk to a tax professional that has experience with intergenerational wealth transfers. Cheaper to get it right up-front versus making mistakes and getting slammed in an audit. Thank you, I will do that. 3 Kids and 5 years+ so this is >>$100k so I agree it's worth getting a backed-up opinio...
by NewMoneyMustBeSmart
Sun Sep 01, 2019 5:52 am
Forum: Personal Finance (Not Investing)
Topic: Gifting to Kids with Lower Tax Rates
Replies: 13
Views: 1235

Re: Gifting to Kids with Lower Tax Rates

We're exploring (without professional input, yet) a future strategy in which we gift stock to the kids and then they sell it for long term capital gains, with lower tax than us. You really should get some professional tax help since not only are there some specific rules but the past court cases an...