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estimated tax on cap gain: ok to spread payments?

Hi,

Large gap gain in feb, plan to pay 110% of last year's tax as estimated payments. Do I need to pay 110% apr 15th (the quarter when I earned the money) or is it ok to spread payments over 4 quarters?

tia,
by gips
Sun Apr 06, 2014 7:17 pm
 
Forum: Personal Finance (Not Investing)
Topic: estimated tax on cap gain: ok to spread payments?
Replies: 1
Views: 165

wash rule etf/fund?

Hi, I have a long term cap gain this year. for argument's sake, let's say it's $100 and I've decided, as part of my overall asset allocation to place into equities. Can I: - buy the s&p 500 etf tomorrow - on dec 31, sell the etf if I have a loss. let's say it's a $20 loss. - on dec 31, buy a fun...
by gips
Fri Apr 04, 2014 12:42 am
 
Forum: Investing - Theory, News & General
Topic: wash rule etf/fund?
Replies: 3
Views: 323

Re: What's the word on Sean Hyman's investing scheme?

supernova wrote:Anyone who claims to know what the market is going to do is wrong


not necessarily. I have a friend that worked for Ivan Boesky, he did a pretty good job of predicting the market (before he went to jail).
by gips
Tue Apr 01, 2014 2:27 am
 
Forum: Investing - Help with Personal Investments
Topic: What's the word on Sean Hyman's investing scheme?
Replies: 9
Views: 1143

Re: My husband is receiving $2.31M for selling his company.

- invest in FDIC insured CDs (max $250k per financial institution) and US Treasury Bonds or funds (up to 5 years ie short term). Then wait a year or so whilst you consider your best investment strategy. Your goal is not to make good investments right now, it's to avoid losing money Minor correction...
by gips
Tue Apr 01, 2014 12:27 am
 
Forum: Investing - Help with Personal Investments
Topic: My husband is receiving $2.31M for selling his company. What
Replies: 15
Views: 3427

Re: wittdrawal percentange taxable vs. non-taxable

ok, lets say my expenses are $100k/year. From a taxable account, I can just remove $100k. From a non-taxable, I have to remove additional monies to account for the tax I pay on the $100k. So a person's "number" calc needs to include whether the money is in taxable or non-taxable, yes?
by gips
Sun Mar 30, 2014 4:40 pm
 
Forum: Investing - Theory, News & General
Topic: wittdrawal percentange taxable vs. non-taxable
Replies: 7
Views: 400

wittdrawal percentange taxable vs. non-taxable

It seems to me the debate on withdrawal rates needs to be informed by whether the money is coming out of taxable or non-taxable accounts. When people model a 4% withdrawal rate, are they thinking taxable or non-taxable accounts?
by gips
Sun Mar 30, 2014 4:25 pm
 
Forum: Investing - Theory, News & General
Topic: wittdrawal percentange taxable vs. non-taxable
Replies: 7
Views: 400

Re: Help me run my company's pension plan

we had a similarly-sized business and our mantra was to outsource everything outside of our core competency including 401k, payroll, hr, health, email, sharepoint, etc. This let us focus on our core competencies: sales, delivery and ops. We were very happy with our providers, suggest you see if you ...
by gips
Thu Mar 20, 2014 9:05 am
 
Forum: Personal Finance (Not Investing)
Topic: Help me run my company's pension plan
Replies: 35
Views: 2149

Re: You Will Be Investing For Free In 5 Years - Article

I've done consulting work for some large asset managers and I've had the idea for about five years that by leveraging technology an index fund can: - trade very efficiently - provide sensible investment advice (see wealthfront) - automate front-to-back processing - charge zero fees - be profitable I...
by gips
Tue Mar 18, 2014 10:12 pm
 
Forum: Investing - Theory, News & General
Topic: You Will Be Investing For Free In 5 Years - Article
Replies: 21
Views: 5344

Re: 3 Big Questions to Ask an Adviser

I think a good question is "how can I beat the Russell 2000 on a risk adjusted basis and if I can't , why do I need your help?"
by gips
Sat Mar 15, 2014 11:38 am
 
Forum: Personal Finance (Not Investing)
Topic: 3 Big Questions to Ask an Adviser
Replies: 34
Views: 2657

Re: Job Offer Negotiation / Interview Snafu

you should have waited for your promotion and then started your job search. Also, you should have tried to maximize job offers to play one company vs. another. People underestimate risk when changing jobs, I think you need a 15-20% increase before it's viable. I'd walk away without thinking twice, g...
by gips
Wed Mar 05, 2014 10:59 pm
 
Forum: Personal Finance (Not Investing)
Topic: Job Offer Negotiation / Interview Snafu
Replies: 175
Views: 15216

Re: reached "my number", struggling with asset allocation

sorry, I guess I posted in the wrong forum. would a kind mod please move this to personal investing.
by gips
Mon Mar 03, 2014 12:15 pm
 
Forum: Investing - Help with Personal Investments
Topic: reached "my number", struggling with asset allocation
Replies: 11
Views: 1403

reached "my number", struggling with asset allocation

Hi, recently sold our business, had a great result and we're probably 2x "our number". I'm 57, will work at least another 3 years and then plan to retire. To date my fixed income allocation has been my age but I'm wondering if that amount of risk is still appropriate. I'd feel pretty silly...
by gips
Mon Mar 03, 2014 11:47 am
 
Forum: Investing - Help with Personal Investments
Topic: reached "my number", struggling with asset allocation
Replies: 11
Views: 1403

Re: struggling with where to place large fixed income alloca

thanks laura, do you mean increase my current position in VGTSX?
by gips
Sat Feb 15, 2014 2:53 pm
 
Forum: Investing - Help with Personal Investments
Topic: struggling with where to place large fixed income allocation
Replies: 3
Views: 320

struggling with where to place large fixed income allocation

Hi, Sold business which generated a lot of cash. I'm 57, married, 3 kids (15,17,18), looking for a 50-50 allocation. Currently my allocation is: $2mm: 30% fidelity spartan total market index (tax advantaged) 20% VGTSX (non-tax advantaged) 50% penfed 3 year cds @2% (non-tax advantaged) I also have $1...
by gips
Sat Feb 15, 2014 2:23 pm
 
Forum: Investing - Help with Personal Investments
Topic: struggling with where to place large fixed income allocation
Replies: 3
Views: 320

Re: where to invest money until the tax man cometh?

thanks, yes, safe harbor planned.
by gips
Tue Feb 04, 2014 11:11 pm
 
Forum: Investing - Help with Personal Investments
Topic: where to invest money until the tax man cometh?
Replies: 5
Views: 452

where to invest money until the tax man cometh?

Hi,

I have a large cap gain, will need to pay taxes apr 2015. thinking I'll purchase a number of one year CDs. Any other thoughts?

tia,
jd
by gips
Tue Feb 04, 2014 10:38 pm
 
Forum: Investing - Help with Personal Investments
Topic: where to invest money until the tax man cometh?
Replies: 5
Views: 452

Re: WSJ - Retiring on Your Own Terms

"you should save a total of 22 times the annual income you want to earn when you retire."

doesn't the number 22 change depending on whether your savings are in a 401k/ira/sep vs. post-tax savings?
by gips
Tue Feb 04, 2014 9:50 pm
 
Forum: Investing - Theory, News & General
Topic: WSJ - Retiring on Your Own Terms
Replies: 22
Views: 4343

Re: How do you use Penfed?

-refinanced our 15 year mortgage to a %1.99 loan with penfed without a hitch. only closing cost was $300 appraisal fee.
- obtained a heloc
- recently move money into their cds

I've had nothing but great customer service from them.
by gips
Sat Feb 01, 2014 12:16 am
 
Forum: Investing - Theory, News & General
Topic: How do you use Penfed?
Replies: 24
Views: 2456

Re: Can we/should we afford this house?

we live in the nyc area and went through a similar process. I suggest you purchase your dream house: - it's something that you and your family will enjoy every single day. - interest rates are very low - you'll be building equity...the money is not just disappearing. - Obviously you know best, but I...
by gips
Fri Jan 31, 2014 5:33 pm
 
Forum: Personal Finance (Not Investing)
Topic: Can we/should we afford this house?
Replies: 63
Views: 4383

Re: asset allocation question

>>If a broad decline in equity markets keeps you from retiring then I would reduce your equity holdings today based on that requirement which has nothing at ll to do with this stock. this is good advice based on the information I've provided...but I haven't (and can't) provided enough information. a...
by gips
Sat Jan 25, 2014 5:44 pm
 
Forum: Investing - Help with Personal Investments
Topic: asset allocation question
Replies: 27
Views: 756

Re: asset allocation question

>>Just because you think the odds are good that something will have value doesn't mean that it will. If we could predict the future with accuracy, making investment decisions would be so much easier. while your statements are true, the asset has obvious value. Using the example of IBM again, let's a...
by gips
Sat Jan 25, 2014 5:01 pm
 
Forum: Investing - Help with Personal Investments
Topic: asset allocation question
Replies: 27
Views: 756

Re: asset allocation question

>>Since you can't sell it the asset really has no value so it should not change your target asset allocation. I'm slowly coming to the conclusion that I don't agree with this approach. I think the asset has a value that should be discounted. The discounted value could be calculated via black-scholls...
by gips
Sat Jan 25, 2014 12:32 pm
 
Forum: Investing - Help with Personal Investments
Topic: asset allocation question
Replies: 27
Views: 756

Re: asset allocation question

here's the problem as I see it. Let's assume I ignore the fact that I have the small cap stock and leave my equities allocation as is. If the small cap stock loses 50% of its value and I have an additional 50% loss in the equities portion of my portfolio, I won't have enough to retire. so I'm thinki...
by gips
Sat Jan 25, 2014 12:13 pm
 
Forum: Investing - Help with Personal Investments
Topic: asset allocation question
Replies: 27
Views: 756

Re: asset allocation question

>>If you put all your equity money into the one small stock and all the rest of your money into bonds or other fixed assets.....if the one small stock fails suddenly, you are >>essentially left with a bond portfolio (till you fix it). Would you have enough money left in the bonds/fixed portfolio to ...
by gips
Sat Jan 25, 2014 1:04 am
 
Forum: Investing - Help with Personal Investments
Topic: asset allocation question
Replies: 27
Views: 756

Re: asset allocation question

>>It also seems pretty obvious it's his company stock (which substantially increases the risk) and that there's not much he can do about it since it's part of his pay package. correct. >> That gives you two options as I see it: >>1) Look at it as you suggest and treat it as your equity portion and p...
by gips
Sat Jan 25, 2014 12:54 am
 
Forum: Investing - Help with Personal Investments
Topic: asset allocation question
Replies: 27
Views: 756

Re: asset allocation question

one small cap stock. of course it's risky, what's your suggestion?
by gips
Sat Jan 25, 2014 12:35 am
 
Forum: Investing - Help with Personal Investments
Topic: asset allocation question
Replies: 27
Views: 756

asset allocation question

right now I'm comfortable with my 60-40 equities-fixed income allocation. It looks like there's a good chance I'll be receiving a small cap stock with a 2-3 year restriction on sale. for argument sake, let's say the restricted stock will represent 60% of my portfolio. Seems to me I have to sell out ...
by gips
Sat Jan 25, 2014 12:06 am
 
Forum: Investing - Help with Personal Investments
Topic: asset allocation question
Replies: 27
Views: 756

Re: dramatically increase 529 savings?

sorry for the confusion >>Is it you currently have $50K per child in the NY529 plan today? for a total of $150K yes >>How much of a gain do you think you will make for the college freshman that it will grow tax-free over the next 3 years dunno, but 3% per year tax free would be a big win compared to...
by gips
Fri Jan 17, 2014 10:22 pm
 
Forum: Investing - Help with Personal Investments
Topic: dramatically increase 529 savings?
Replies: 6
Views: 982

dramatically increase 529 savings?

Hi, we've saved enough money to fully fund our 3 kids college educations. One is a college freshman, one a hs junior and the youngest is a hs freshman. I currently have about $50k/child in the NY 529 plan. Thinking maybe I should move $50k per child into the 529 plan so it can grow tax free? thoughts?
by gips
Fri Jan 17, 2014 9:41 pm
 
Forum: Investing - Help with Personal Investments
Topic: dramatically increase 529 savings?
Replies: 6
Views: 982

Re: selling business for cash/stock, when is tax due on stoc

well, I just spent four hours reading the tax code and I think I understand where the accounting company is coming from. In fact, they have a paper on their website which makes it pretty clear. Our firm provides services so it doesn't qualify for 1202.
by gips
Sat Dec 28, 2013 1:10 am
 
Forum: Personal Finance (Not Investing)
Topic: selling business for cash/stock, when is tax due on stock?
Replies: 6
Views: 370

Re: selling business for cash/stock, when is tax due on stoc

one opinion comes from a partner at a national accounting firm, the other from a business valuation expert that has been involved in many, many deals.
by gips
Fri Dec 27, 2013 11:54 pm
 
Forum: Personal Finance (Not Investing)
Topic: selling business for cash/stock, when is tax due on stock?
Replies: 6
Views: 370

selling business for cash/stock, when is tax due on stock?

I've been getting different opinions on this question: - have an offer for stock sale of business for cash and stock of a publicly traded company (let's call it ticker GIPS) - GIPS stock is restricted such that it can't be sold for 2 years, no hedging allowed - is long term cap gains on non-cash por...
by gips
Fri Dec 27, 2013 10:50 pm
 
Forum: Personal Finance (Not Investing)
Topic: selling business for cash/stock, when is tax due on stock?
Replies: 6
Views: 370

Re: best place for $750k of cash?

thanks for all the great ideas! I'm already a penfed member so that seems pretty easy for about $250k. I'll leave around $100k in the bank accounts and then I'll find find two more cu/banks for the rest.
by gips
Sat Nov 16, 2013 7:36 pm
 
Forum: Investing - Help with Personal Investments
Topic: best place for $750k of cash?
Replies: 11
Views: 2012

best place for $750k of cash?

hi, I have $750k spread between two bank accounts. My goals are: 1 better return without risk to principal 2 ensure accounts are within FDIC insurance limits 3 not spend a lot of time managing the money. to the extent possible, I'd like a set and forget strategy. 4 not to pay an advisor I'm subject ...
by gips
Sat Nov 16, 2013 3:49 pm
 
Forum: Investing - Help with Personal Investments
Topic: best place for $750k of cash?
Replies: 11
Views: 2012

Re: Can I retire?

>>Personally, I feel like paying 100% of a kid's education is a major mistake. >>I personally feel the same way, but didn't want to come right out and say it. :happy Just because I can (and I can) doesn't mean that I should or that it's good for them. what's the suggestion? They take loans and gradu...
by gips
Wed May 15, 2013 9:31 pm
 
Forum: Personal Finance (Not Investing)
Topic: Can I retire?
Replies: 78
Views: 7643

preparing for large long-term cap gain

Hi, I own shares of a startup that may be sold over the next year or two. Is there anything I could/should be doing to lessen the tax impact of the sale? The gains will be taxed at the long-term cap gains rate. Anything else I should be thinking about in terms of financial planning around the gain? ...
by gips
Tue May 14, 2013 11:44 pm
 
Forum: Personal Finance (Not Investing)
Topic: preparing for large long-term cap gain
Replies: 5
Views: 946

Re: pay down 1.99% mortgage?

I've decided to continue to pay off the loan over the next five years rather than pay it off now. My reasoning is: - I'll probably have a small loss over the next year or two but interest rates will probably go up giving me an opportunity for a gain. - there's an opportunity cost if I pay off the lo...
by gips
Tue May 14, 2013 11:37 pm
 
Forum: Personal Finance (Not Investing)
Topic: pay down 1.99% mortgage?
Replies: 30
Views: 1952

Re: Can I retire?

We don't really know much about the OP's income but it's not a far-fetched assumption that another year of work would get him pretty close to fully funding his kid's education. I'd personally have a tough time telling my kids to compromise on their college choice because I wanted to retire at 45 rat...
by gips
Tue May 14, 2013 7:04 pm
 
Forum: Personal Finance (Not Investing)
Topic: Can I retire?
Replies: 78
Views: 7643

Re: Can I retire?

have you looked at current college costs? We have a target of $250k/child for our three kids.
by gips
Tue May 14, 2013 4:16 pm
 
Forum: Personal Finance (Not Investing)
Topic: Can I retire?
Replies: 78
Views: 7643

Re: pay down 1.99% mortgage?

twins fan, for many years I held a deep belief that investments in broad US equity indices would conservatively yield 6%. 7 to 10 years ago that's where the money would have gone. While I've ridden out every market downturn and resisted market timing, I'm no longer convinced future returns are so ro...
by gips
Mon May 13, 2013 11:22 pm
 
Forum: Personal Finance (Not Investing)
Topic: pay down 1.99% mortgage?
Replies: 30
Views: 1952

Re: pay down 1.99% mortgage?

Yes. The 5-year duration is the correct comparison now; when you are three years from the reset, you would compare to a bond fund with a 3-year duration in deciding whether to pay down the loan at that time. You don't actually need to hold a bond fund with a 5-year duration, just to recognize that ...
by gips
Mon May 13, 2013 11:00 pm
 
Forum: Personal Finance (Not Investing)
Topic: pay down 1.99% mortgage?
Replies: 30
Views: 1952

Re: pay down 1.99% mortgage?

ouch, I conflated my last loan and this loan! you're absolutely right, it's a five year HEL, fixed at 1.99% for five years. Paying it down is an investment with a 5-year duration, as any remaining balance after five years will be refinanced at the current market rate. Therefore, the fair comparison...
by gips
Mon May 13, 2013 10:42 pm
 
Forum: Personal Finance (Not Investing)
Topic: pay down 1.99% mortgage?
Replies: 30
Views: 1952

Re: pay down 1.99% mortgage?

gips, Welcome to the forum! Are you sure you have your numbers right? PenFed had 2 loans with a 1.99% rate. One was a 5 year HEL, the other was a HELOC with an introductory rate of 1.99%. PenFed also had a 10 year HEL at 2.99%. You indicated your rate is 1.99%, but also noted you'll have it paid of...
by gips
Mon May 13, 2013 10:31 pm
 
Forum: Personal Finance (Not Investing)
Topic: pay down 1.99% mortgage?
Replies: 30
Views: 1952

Re: pay down 1.99% mortgage?

Watty wrote:If you had a paid of house would you take out a home equity loan just to invest it?


that's precisely what I'm trying to figure out! :sharebeer
by gips
Mon May 13, 2013 10:21 pm
 
Forum: Personal Finance (Not Investing)
Topic: pay down 1.99% mortgage?
Replies: 30
Views: 1952

Re: pay down 1.99% mortgage?

- it's a home equity loan, not a heloc. - I don't really think of it as numbers vs. peace of mind schools of thought. I think of it as bankers vs. economists. A banker will tell you to pay it off early and not pay interest. An economist will tell you that today's dollars are much more valuable than ...
by gips
Mon May 13, 2013 9:45 pm
 
Forum: Personal Finance (Not Investing)
Topic: pay down 1.99% mortgage?
Replies: 30
Views: 1952

pay down 1.99% mortgage?

Hi, We refinanced our 4.25%, 10 year mortgage with a %1.99 five year fixed penfed hel. our balance is around $175k. we have enough cash to pay off the mortgage and I'm maxing out my pre-tax investments. We have no other debt. On one hand, it's tough to find a risk-free investment paying 1.99% (after...
by gips
Mon May 13, 2013 7:46 pm
 
Forum: Personal Finance (Not Investing)
Topic: pay down 1.99% mortgage?
Replies: 30
Views: 1952

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