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13
votes
2answers
1k views

As an employee, when is it inappropriate to request to see your young/startup company's financial statements?

If you work for a young company, equity in the form of restricted stock or options is often a form of compensation and a way to keep you aligned with the company's goals. But as a new employee you ...
2
votes
1answer
43 views

Does the section 1202 qualified small business stock reduce New York, Illinois, or California taxable income?

Say I sold a small amount of stock that qualifies for section 1202. Does this reduce my New York taxable income, or just the federal capital gains amount?
1
vote
2answers
92 views

What ways can an employee keep the upside of stock options after leaving?

Suppose that you work at some private company and that company offers some stock options to you as part of employment. For the sake of discussion, suppose they offer 100 000 options at $0.50 an ...
1
vote
1answer
130 views

Had employee options in a company that has been sold to another foreign company. What happens?

One of my parents had employee options in a company that was based in the US. Recently however, that US company had been sold off to a German company (now based in Germany). Question is, what ...
2
votes
1answer
225 views

When should I exercise my startup stock options? How would it be taxed?

Let's say I'm an employee at a startup where I own fully vested stock options. Scenario 1 I have not exercised my stock options and my startup was bought. Do I still get to exercise my options? The ...
0
votes
1answer
51 views

AMT stock option scenario

So I have some ISO stock options (yeah) and three kids in college (boo) so I'm trying figure out the best tax strategy. I was hoping someone help me through the following scenario Strike Price: $10, ...
3
votes
3answers
99 views

How a company can afford to give away so many shares as part of its ESOP

As part of an employee share ownership plan (ESOP), the employee(s) get a certain # of shares held in their name. Every month, the employer also matches the contribution and let us assume the employee ...
1
vote
1answer
36 views

Would an ESOP issue physical shares or stock options (call options) to participating employees?

The ESOP (Employee Stock Options Plan) has the word 'options' in it. Is it the same "options" as in "futures and options', i.e are there physical company shares held under the ESOP in an employee's ...
2
votes
1answer
76 views

Can a self-directed IRA hold non-qualified stock options (NSO) with a vesting period, without being considered self-dealing?

I work for a startup company. They are about to go through their FMV evaluation and funding round, at which point I will be granted my options. I talked to them and said I would like the ability to ...
4
votes
2answers
114 views

What to consider before buying (exercising) a family member's private company employee stock options, about to expire?

My brother-in-law is leaving a private tech company. He has $100,000 in stock options (fully vested) which he must either purchase, or abandon completely upon his exit. This is not a startup — ...
4
votes
2answers
92 views

Is it a wise decision to sell my ESPP stock based on this situation?

My wife lost her job in the middle of 2013 and has been unemployed since then. I have about $7000 of company stock. I am planning to pay my car off using that money but I am not sure if this is the ...
2
votes
1answer
94 views

Exercise ISO or NSO in solo 401k?

I have a solo 401k. My employer does not offer one. What is the correct way to exercise employee stock options with capital from the 401k to make the resulting stock an asset of the 401k? Ideally ...
2
votes
1answer
105 views

Company gets rid of bonus structure and replaces it with cash and options. What gives?

Here is how it went down and what they're offering me. What should I make of it/ask them about? 1) They are changing the bonus structure to allow me to get the payout IF we make a certain revenue ...
2
votes
2answers
73 views

If I exercise underwater ISOs, can I claim a loss?

From what I understand, if I exercise in-the-money ISOs, I'll be taxed on the supposed gains, even if the stock isn't tradeable (because, for example, it's stock in a privately-held company). Does ...
5
votes
1answer
123 views

Employee stock option plan with undefined vesting?

As an employee, I have received stock options from my company. However, about vesting, it says only that the board determines it. There is no further info, no vesting period is stated, no further ...
7
votes
3answers
511 views

Confused about employee stock options: How do I afford these?

I'm confused about stock options. The numbers in the following story are fictional because I'm keeping the actual offer confidential. This is an American private company with a promising future: ...
2
votes
1answer
133 views

Exercising stock options in a private company when the strike price is higher than current FMV

An employee leaving our Private Subsidiary wants to exercise his stock options, despite his strike price being higher than the current valuation ($1.00 vs $0.84). Was wondering what the tax ...
2
votes
1answer
213 views

How do I treat the income from an ESPP I sold now that I am a non-resident alien?

I worked in the US in 2009 and was granted an Employee Stock Purchase Plan (ESPP), which I exercised. Then later I left the US and sold the stock, which is a qualified disposition. Now I am going to ...
2
votes
2answers
339 views

How can I estimate the value of private stock behind employee stock options?

I'm considering an offer with generous options. I have pretty high risk tolerance, so I'm just trying to estimate the expected value of the options. To the extent possible, I want to base this on the ...
3
votes
1answer
947 views

How do I enter Canadian tax info from US form 1042-S and record captial gains from cashing in stock options?

I am assuming these issues are related. I am working in Canada for a US company. I buy stock options every quarter. In 2011 I cashed in some stock options and received the cash. How do I enter the ...
7
votes
1answer
58 views

Capital losses on early-purchased stock?

If I exercise an early purchase clause on employee incentive stock options to go ahead and purchase the stock and the company later goes bust, can I take capital losses against that stock?
7
votes
1answer
237 views

Can I apply prior years' capital losses against my employee stock option exercise?

I'm Canadian, and I executed a "same-day-buy-and-sell" on options granted to me by my employer. My T4 slip has the appropriate taxable benefit called out, but my question is, can I apply my previous ...
2
votes
1answer
200 views

When Employees are “Granted” Stock Options, is the Company encouraging Long-Term investments from them?

I'm not exactly sure I understand the "why" behind a Company reasoning for offering "options" to their employees to invest in itself. I've found it is very unlikely of the employees to exercise for a ...
4
votes
2answers
91 views

Buying non-qualified employee stock options that are going to expire?

I have NQ stock options from my employer that have to be exercised in the next few months before they expire. I would like to hang on to them as I have faith in the stock itself. What are my options? ...
4
votes
1answer
952 views

Can capital gains from employee stock options be transfered to a TFSA to avoid taxes?

In a scenario where, for example: An employee exercised a "same-day-buy-and-sell" operation on his employee stock options. He ends up making a profit / gain of $10K. He already has a yearly salary of ...