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Re: selling company stock after loss

thanks, yes, I know about options but I signed an agreement that I wouldn't hedge.
by gips
Tue Sep 30, 2014 7:59 pm
 
Forum: Investing - Theory, News & General
Topic: selling company stock after loss
Replies: 3
Views: 157

selling company stock after loss

Hi, I received stock in a publicly traded company as partial compensation for my business. I can't sell the stock for 2 more years. Unfortunately, I'm down about $1mm. In 2 years, it seems to me I should sell the stock without regard to whether I've made or lost money and allocate proceeds in line w...
by gips
Tue Sep 30, 2014 7:32 pm
 
Forum: Investing - Theory, News & General
Topic: selling company stock after loss
Replies: 3
Views: 157

Re: rebalancing towards bernstien philosophy

thanks folks, couple of comments: - that $1.2mm vacation house fund is off-limits for investing so that leaves around $5mm - since I want $3mm in short term fi, I'd have to invest everything else ($2mm) in equities for a 40% eq allocation. Since I'll free up another $700k-$1mm when we sell our curre...
by gips
Tue Sep 30, 2014 4:17 pm
 
Forum: Investing - Help with Personal Investments
Topic: rebalancing towards bernstien philosophy
Replies: 3
Views: 338

rebalancing towards bernstien philosophy

hi, I'm starting to come around to bernstien's "if you've won the game" guidance. Here basic stats: age - 58 state - ny tax rate - highest target retirement date - 12/2016 college - fully funded, empty nest 12/2016 mortgage - $112k @ 1.99, paid off around 12/2016 emergency fund $100k curre...
by gips
Tue Sep 30, 2014 3:28 pm
 
Forum: Investing - Help with Personal Investments
Topic: rebalancing towards bernstien philosophy
Replies: 3
Views: 338

Re: How I beat Indexing... in 1 hour

Alibaba IMO has already proven profitability. If you are a buy-and-hold guy, with a decades-long horizon, BABA is a good bet. The only question if the valuation. If you think it's overvalued right now, you could make the same argument with indexed mutual funds, as they are at an all-time P/E high. ...
by gips
Mon Sep 29, 2014 11:55 pm
 
Forum: Investing - Theory, News & General
Topic: How I beat Indexing... in 1 hour
Replies: 69
Views: 10758

Re: In theory, market timing = index investing

Beliavsky wrote:Undiversified investing does not reduce average arithmetic returns but will reduce average geometric or compounded returns because of the higher and uncompensated volatility.


really? seems very unlikely, can you prove it or provide a link to an article that does?
by gips
Mon Sep 29, 2014 6:50 pm
 
Forum: Investing - Theory, News & General
Topic: In theory, market timing = index investing
Replies: 10
Views: 616

Re: In theory, market timing = index investing

First, I think your title is misleading, you should add EV in there somewhere. Second, while your premise is correct, it simply confirms why index investing is preferable.
by gips
Mon Sep 29, 2014 5:06 pm
 
Forum: Investing - Theory, News & General
Topic: In theory, market timing = index investing
Replies: 10
Views: 616

Re: Your 529 Plan - Thoughts and Strategies

1. How old are your children who you're saving for? 18, 16, 14 2. Which 529 Plan do you invest in? ny 3. What's the current balance? around $50k/kid 4. How much do you contribute and how often? How did you come to this number? $800/month. Wanted to max out ny state deduction. 5. What are the underly...
by gips
Thu May 22, 2014 12:01 am
 
Forum: Investing - Theory, News & General
Topic: Your 529 Plan - Thoughts and Strategies
Replies: 39
Views: 2878

Re: "Get out of bond funds"

I see...for an apples to apples comparison, wouldn't you want to consider the income from investing the coupons at 1% were one to hold on to the bond?
by gips
Mon May 12, 2014 11:42 pm
 
Forum: Investing - Theory, News & General
Topic: "Get out of bond funds"
Replies: 147
Views: 23004

Re: "Get out of bond funds"

Concrete example from today's pricing. Maturity Coupon Bid Asked Chg Asked yield 8/15/2015 10.625 113.1563 113.1797 -0.0234 0.148 If you have 1000x of this bond, you could hold, make another $13280 in interest, get $100K at maturity, for a grand total of $113280. Or you could sell for $113150, put ...
by gips
Mon May 12, 2014 11:15 pm
 
Forum: Investing - Theory, News & General
Topic: "Get out of bond funds"
Replies: 147
Views: 23004

Re: The Price of Outperformance

I'd make these points: - Buffet's article was written prior to increased sophistication of computers, computer models and algorithms. These tool/market participants have made the market much more efficient since the time the article was written. Additionally, the publishing of the article itself mad...
by gips
Sat May 10, 2014 1:40 pm
 
Forum: Investing - Theory, News & General
Topic: The Price of Outperformance
Replies: 35
Views: 3658

Re: Boglehead 4wd Car (for family)?

sunnyday wrote:I'm in a similar boat. I've done a bunch a research on car safety and am getting a 2015 outback with eyesight technology when they come out.
Take a look at Informedforlife.org for safety.


this is exactly what I plan to do. lot of good information at www.subaruoutback.org
by gips
Mon May 05, 2014 7:30 am
 
Forum: Personal Consumer Issues
Topic: Boglehead 4wd Car (for family)?
Replies: 38
Views: 3483

Re: Why have a HELOC

the interest you pay is often tax deductible.
by gips
Mon May 05, 2014 7:24 am
 
Forum: Personal Finance (Not Investing)
Topic: Why have a HELOC
Replies: 19
Views: 1748

Re: "Swedroe: Hard To Know Who’ll Outperform"

What's left out of the article is the hero worship ascribed to fund managers that outperform the market. The media sees a fund manager that beats the market five years running and instead of realizing "there's a large population of fund managers and some of them are going to beat the market ove...
by gips
Sun May 04, 2014 12:28 pm
 
Forum: Investing - Theory, News & General
Topic: "Swedroe: Hard To Know Who’ll Outperform"
Replies: 5
Views: 1470

Re: Options Trading: shooting down the "iron condor"

I've worked on both the business and technology sides of options platforms for large, well-known, broker dealers. I can speak with some authority on these points: - the options market is very efficient. Therefore, on a risk adjusted basis where one has to pay transaction fees, it's unlikely anyone c...
by gips
Sun May 04, 2014 12:18 pm
 
Forum: Investing - Theory, News & General
Topic: Options Trading: shooting down the "iron condor"
Replies: 19
Views: 2018

Re: Avoiding large cap gain by creating and selling losers?

thanks, a lot of thoughtful advice: "The 2x or 3x ETFs don't work the way people expect them to" yes, after some research, I agree, bad idea. "I think a better idea is to invest wisely enough to create the necessary additional gains to pay the taxes." Isn't my idea of investing m...
by gips
Sun May 04, 2014 9:40 am
 
Forum: Investing - Help with Personal Investments
Topic: Avoiding large cap gain by creating and selling losers?
Replies: 10
Views: 806

Re: Avoiding large cap gain by creating and selling losers?

That would be perfect...as long as I can generate an equally sized gain next year.
by gips
Sat May 03, 2014 4:14 pm
 
Forum: Investing - Help with Personal Investments
Topic: Avoiding large cap gain by creating and selling losers?
Replies: 10
Views: 806

Avoiding large cap gain by creating and selling losers?

Sold our business this year will have 7 figure long term cap gain tax bill. Was thinking about investing my gain in line with my asset allocation using 3 fund strategy. At year end I'll sell losers and invest in a like eft with an eye to avoiding the wash rule. This allows me to deduct the loss agai...
by gips
Sat May 03, 2014 2:02 pm
 
Forum: Investing - Help with Personal Investments
Topic: Avoiding large cap gain by creating and selling losers?
Replies: 10
Views: 806

cd ladder distribution

Hi,

After a lot of thought and reading on bond fund vs cd, I've decided to setup a cd ladder in my ira account. vanguard brokered cds are 3.3% for 10 years and rates move down based on maturity.

I'm wondering how people here have distributed their money across different cd maturities?

tia,
by gips
Wed Apr 30, 2014 10:48 am
 
Forum: Investing - Theory, News & General
Topic: cd ladder distribution
Replies: 12
Views: 1200

Re: using etf to avoid citibank checking fees?

I agree it's not worth $30 per month hence looking for a way to keep it at a lower cost. Here's what I like: - no fx fees using atms in other countries - separate number for support with better communication skills and training - on citi website I can find the citigold rep at each branch and make an...
by gips
Tue Apr 29, 2014 11:14 pm
 
Forum: Personal Finance (Not Investing)
Topic: using etf to avoid citibank checking fees?
Replies: 7
Views: 1184

Re: State tax deductible 529

Your math looks good but you may want to consider other factors, which, off the top of my head, include: - money will grow tax free in the 529 - amt may eliminate your state and local deduction - the dc 529 plan may have high fees - money in 529 plans may reduce financial aid On another note, that's...
by gips
Tue Apr 29, 2014 7:03 pm
 
Forum: Personal Finance (Not Investing)
Topic: State tax deductible 529
Replies: 6
Views: 1609

Re: State tax deductible 529

It's not a no-brainier because you need to factor in the loss of the state or local tax deduction on your federal return.
by gips
Tue Apr 29, 2014 9:05 am
 
Forum: Personal Finance (Not Investing)
Topic: State tax deductible 529
Replies: 6
Views: 1609

Re: using etf to avoid citibank checking fees?

I'm sorry to hear that, I'd generally agree their customer service is not very good but again, I do find the citigold service to be excellent.
by gips
Mon Apr 28, 2014 11:47 pm
 
Forum: Personal Finance (Not Investing)
Topic: using etf to avoid citibank checking fees?
Replies: 7
Views: 1184

Re: Convince me to lump sum into the market

I just lump summed a similar amount into the market. My view is:

- historically market has moved up
- you can't time the market

is there really anything else you need to think about?
by gips
Mon Apr 28, 2014 10:36 pm
 
Forum: Investing - Help with Personal Investments
Topic: Convince me to lump sum into the market
Replies: 57
Views: 11164

using etf to avoid citibank checking fees?

I've been using citibank for many years, their customer service used to be terrible but they've created a tier of service called citigold where if you keep $50k in bank accounts or $100k in brokerage they waive monthly fees and provide excellent service. Their savings account pays about .2% as oppos...
by gips
Mon Apr 28, 2014 10:31 pm
 
Forum: Personal Finance (Not Investing)
Topic: using etf to avoid citibank checking fees?
Replies: 7
Views: 1184

muni bond funds and amt

Hi,

I'm guessing I'll be subject to amt this year (2014). I was thinking about a vanguard muni bond fund in my non-taxable account but was wondering if I might lose some of the tax advantages to amt?

tia,
by gips
Sat Apr 26, 2014 9:07 pm
 
Forum: Investing - Theory, News & General
Topic: muni bond funds and amt
Replies: 3
Views: 1146

Re: work 3 years for 20x payout or retire and wait 10 years

thanks for all your thoughtful replies. Here are some answers to your questions: - I've never smoked, I'm not overweight, I'm in decent shape - I don't know what I'd be doing, perhaps take college courses, travel and get in better shape - I own restricted stock in a publicly traded company. The comp...
by gips
Sat Apr 26, 2014 5:45 pm
 
Forum: Personal Finance (Not Investing)
Topic: work 3 years for 20x payout or retire and wait 10 years
Replies: 11
Views: 1639

work 3 years for 20x payout or retire and wait 10 years

Hi, I've been mulling this over for the past couple of months: - work 3 years, decent salary and receive lump sum payment of about 20x current expenses or - retire tomorrow and wait 10 years for lump sum payment. - I currently have 20 times current expenses saved. We're in one of the highest cost of...
by gips
Sat Apr 26, 2014 12:21 pm
 
Forum: Personal Finance (Not Investing)
Topic: work 3 years for 20x payout or retire and wait 10 years
Replies: 11
Views: 1639

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: 176

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: 353

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: 1591

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: 3556

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: 436

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: 436

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: 2356

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: 5612

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: 2823

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: 177
Views: 31299

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: 1426

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: 1426

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: 336

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: 336

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: 459

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: 459

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: 4824

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: 2657

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: 4760

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: 779

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: 779

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: 779
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