Equity - date of offer, or date of joining?
Options or Shares vest by date they are granted. It would strike me as odd for anyone to say their shares were given with 4 year vesting, but the clock was pre-started years prior.  In my opinion, you have nothing to complain about. TL;DR: The date they were granted.  (Usually, this follows both an offer and acceptance.) It's not uncommon for a new vesting clock to start when there's a new round of funding coming in, because the investors want to make sure the key people are going to be engaged and incentivized going forward from that point.  They don't lower their expectations for how long they want folks engaged based on the person having started earlier.  Non-institutional investors may have the same concerns as institutional investors here and use the same vesting strategy to address them. Primary recognition of the benefits from having had people start earlier or be there longer (so long as it correlates with having gotten more done) is embedded in the valuation (which affects how much founders' shares are diluted in the raise).
Is the Grant Date or the Vest Date used when determining the 12-month cutoff for long-term and short-term capital gains? You don't actually acquire the stock until it's vested, so that is the date and price used to determine your cost basis and short-term/long-term gain/loss.  The grant date really has no tax bearing. If you held the stock (time between vesting and sale) for more than one year you will owe long-term CG tax, if less than one year you will owe short-term CG tax. "You are confining the way you and the other co-founders are paid for guaranteeing the loan to capital shares. Trying to determine payments by equity distribution is hard. It is a practice that many small companies particularly the ones in their initial stage fall into. I always advise against trying to make payments with equity, weather it is for unpaid salary or for guaranteeing a loan such as your case. Instead of thinking about a super sophisticated algorithm to distribute the new shares between the cofounders and the new investors, given a set of constraints, which will most probably fail to make the satisfactory split, you should simply view the co-founders as debt lenders for the company and the shareholders as a capital contributor.  If the co-founders are treated as debt lenders, it will be much easier to determine the risk compensation for guaranteeing the loan because it is now assessed in monetary units and this compensation is equal to the risk premium you see fit ""taking into consideration the probability of default "". On the other hand, capital contributors will gain capital shares as a percentage of the total value of the company after adding SBA loan." Note that your link shows the shares as of March 31, 2016 while http://uniselect.com/content/files/Press-release/Press-Release-Q1-2016-Final.pdf notes a 2-for-1 stock split so thus you have to double the shares to get the proper number is what you are missing. The stock split occurred in May and thus is after the deadline that you quoted. "I write software myself and was involved in a couple of start ups.  One failed, another was wildly successful, but I did not receive much in compensation. The former I received stock, but since it failed, it was worthless anyway.  There should be compensation for your time in addition to equity in a company.   Any agreement needs be in writing.  In the later situation I was told to expect about a 17%/year bonus, but nothing could be guaranteed.  Translation:  ""It will never happen.""  It didn't, but I meet my lovely wife there so I have that for a bonus. Agreements need to address the bad things can happen.  What happens if one of you is no longer interested in continuing?  What happens if one of you die, or addicted to something?  What happens if one of you gets thrown in jail or disabled?  Right now you are full of optimism and hope, but bad things happen.  Cover those things while you still like each other. It might be enough to have a good salary, and some stock options.  You man not be interested in running the day to day business. Most of all good luck, I wish you all the best!" Maybe one of my issues is that I have a 5 year model with a terminal value. The repayment of debt principal is outside this time frame so I don't assume any repayment.   If you're valuing a company share price though you don't model all debt repayments. I wouldn't get too caught up with this. Doesn't sound like this is even stock reconciliation, more ensuring the cash you've received for dividends &amp; other corporate actions agrees to your expected entitlements and if not raising claims etc. Well it depends on whether or not your differentiating against. If its capital stock or stock as in a share certificate in the company. If its a share in the company then in my opinion using Equity would be best as it is a form of an asset and does refer to a piece of ownership of the entity. I wouldn't consider a share of stock a service, since the service to you is say Facebook or the broker who facilitates the transaction of buying or selling FB stock. I also would not consider it a Capital Good, as the Capital Good's would be the referring to the actual capital like the servers,other computer equipments etc. Get involved a lawyer and Accountant. Without it you may not be sure what you are getting. What exactly will 30% mean for me? It will mean exactly what gets written in contract. It can mean you are owner of 30% of the company. If this is structured as partnership, it would also mean you are party to 30% loss. It can mean by current valuation, you get x fixed shares. In future if the directors creates more shares, your % ownership can get diluted. Or anything else. It all depends on what is written in contract and how the contract is structured. Is there anything I should I be aware of before agreeing? Get a draft and talk to a Lawyer and Accountant, they should be able to tell you exactly what it means and you can then decide if you agree to it or not; or need this contract worded differently. * Absolutely agree with /u/IsAnAlpaca  * You /must/ not agree to this without seeing his balance sheet. * That means assets and liabilities, but also ask for the last 12 months' cash flow * Inability or unwillingness to provide any of those things is a HUGE no-go red flag. In my experience, any kind of equity you may be offered by the company is just a carrot. Your offer may be written in such a way that your potential ownership represents, say, 1% of the company today. But if the company goes for a round of financing your ownership percentage can get diluted. If this happens a couple of times and the terms of financing aren't very favorable then your percentage can go from that 1% down to 0.001%, making the equity worthless. I've known people who heard their company was being bought and thought they might get some kind of payoff. Come to find out the company hadn't done all that well and there wasn't anything to pay out after the main investors got some money back. (The main investors took a loss.) For obvious reasons, management wasn't keeping the staff up to date about the fact that they were operating in the red and their options were worthless. Some people grumbled about lawyers and filing lawsuits, but at the end of the day, there wasn't any money to be won. Keep this in mind. As to your question regarding what to look out for: We struck a deal. I sold an asset to some body on june 1 . However he says, he would pay me any time on or before august 1st . This puts me in a dilemma.  What if price goes down by august 1st and i would have to accept lower payment from him.? If price goes up till august 1st, then obviously i make money since ,even though item is sold,price is yet to be fixed between parties. However i know anytime on or before august 1st, i would get paid the price quoted on that particular day. This price could be high in my favor, or low against me. And, this uncertainty is causing me sleepless nights. i went to futures market exchange. My item (sugar,gold,wheat,shares etc..anything). i short sell a futures which just happens to be equivalent to the quantity of my amount i sold to the acquirer of my item. I shorted at $ 100 , with expiry on august 1st. Now fast orward and august 1st comes. price is $ 120 quoted . lets Get paid from the guy who was supposed to pay on or before august 1st. He  pays 120 $. his bad luck, he should have paid us 100 $ on june 1st instead of waiting for august 1st . His judgement of price movement faulted. WE earned 20 $ extra than we expected to earn on june 1st (100$) . However the futures short of 100$ is now 120$ and you must exit your position by purchasing it at back. sell at 100$ and buy at 120$ = loss of 20$ . Thus 20 $ gained from selling item is forwarded to exchange . Thus we had hedged our position on june 1st and exit the hedge by august 1st. i hope this helps Thanks for the info.  I am quite familiar with FAs and I definitely do not want to go that route.  I highly doubt I can get an equity research role considering my lack of real experience.  I was just trying to get an entry-level position and given my resume, I'm having a tough time doing even that :\  It's really unfortunate, I wish I articulate my experience to a hiring manager BEFORE they looked at my resume! It turns out that in this special case for New York, they have a law that says that if you are changing your filing status from resident to nonresident, you must use the accrual method for calculating capital gains. So in this case, the date on the papers is the important one. "Hmm, this site says If you use Quicken, you enter a new transaction of type ""Corporate Acquisition (stock for stock)."" You put investor shares as the ""Company acquired"", Admiral shares as the ""Acquiring company"", and the conversion ratio 0.7997754 as the ""New shares issued per held share"" number. Seems crazy, but maybe that's the way. Edit: This sucks. In the comments, you can see that people have to manually correct the share price for every transaction because of rounding problems." A company is basically divided into shit the company owns (assets) and shit the company owes to people (liabilities). So what about ownership? Ownership is called equity and on a simplistic level equity = asset - liabilities. But a better view of that should be asset = liabilities + equity. Which means a company's assets  is separated into things owned by debtors (e.g. Banks) and things owned by owners(founders and you). So when you are offered one percent, you are basically owning one percent of the company.   Not the best explanation, but should be a simplified one.   Here's where the options come in. When you are offered options. That means you have the option of redeeming the shares at a lower price than market. However these options are not usually immediately redeemable, there's usually a minimum amount of time you have to work at a company to be able to use these options. This period is called the vesting period.