Question on ESOPs

Hi, Say a Series B (US) funded startup gives me 3000 shares which are worth $5/share. It follows the usual vesting period of 4 years. Now assume 4 years have passed and all the 3000 shares are vested but the company hasn't gone IPO. Here are my quesions - When exercising US stocks in India, what is the % of withholding tax I should pay? - Say if I exercised all the shares and if I decide to leave the company do I get to keep those exercised shares with me forever? I prefer answers from people who have exercised ESOPs before. I don't want answers like "It depends, Talk to your HR or CA". Appreciate any inputs.

I work in a fintech company. Revenue and growth wise we are good, we just got acquired by a large internet platform too. Also, last year has been a tremendous learning for me as well. I like being PM but looking to move out of my current industry (lending) as I want to explore other domains and I feel like my CTC here is somewhat low (18.5 + 1.5 bonus) considering my experience (around 4.5 years). My boss said that I will get ESOPS (around 10 lacs) which I can liquidate around 50% this year. Should I wait for my appraisal to complete (will happen around April) and look to switch or should I start preparing for interviews now itself?

Truths about ESOP 101 After working in multiple fast growth startup’s and having been part of multiple buybacks as well as being in the startup ecosystem for a decade I want to put to bear my pov about creating wealth through ESOP. Like any other randomised event, ESOP also follows Pareto principle which means a very small number of people within the company ever make sizable wealth that they elevate to the top 0.1% of the country. The Pareto also applies with companies; significantly small minority of companies in India have employee friendly policies which enables an employee to create wealth. Most startup’s have dark patterns within their esop policy which either locks you in for insufferable durations or forces you to pay exorbitant taxes to gain the right to exercise your esops when you are leaving the company. Survivorship bias plays a huge role in enabling the narrative that esop is a great wealth generating tool leading to rude awakening for an employee after they join a company. This doesn’t mean you can’t make wealth, it just means don’t get carried away by narratives and take preventable errors in your career. Always talk to multiple people in startup’s and ask relevant questions to understand esop policies better. Like everything else optimising only for esop for wealth creation will mostly not result in it.

I am at a VC backed early stage startup. Have been offered Esops.l but have no clue on this. Can somebody explain to me how can I make money from ESOP by answering these- 1) Do I have to buy them post vesting period? If yes, what amount do I need to pay? Also will there be text on this purchase itself? 2)) When the company buys back from me assuming my vesting was over and I could hold them on, what's the amount I will get? I am assuming it's (no of options * current share price) - (no of options * strike price issued to me). Is that correct? If yes, how is the current share price calculated for non listed company? 3) Now when the company buys these, what's the tax I have to pay? I am trying to understand if availing options and selling options are different and if both have taxes 4) What happens in IPO? Who buys from me? Where can I sell? What price do I sell at?

Hi Guys, what is the “Exercise event” for the ESOPs allotted by Indian startup’s? Note: Exercise event means when the vested ESOPs can be allotted. I have come across a couple startup’s which have a very sketchy Exercise event I.e 4 years after vesting of “all the allotted ESOPs” So I’m trying to figure out how other startup’s are doing it in BLR/Metro cities in India.

Hi, I got an offer from a Series B startup and they are giving me 3000 shares of ESOPs vested over 4 years. Right now the value of each shares are worth $5 and has a potential to grow after new funding rounds this year. I feel 3000 shares is less and want to negotiate for more. In your experience can anyone tell me how much ESOPs (shares) have you received from new startups? And was it benefecial in the long run? Any input is appreciated.

Ever heard about people getting payout for their vested ESOPs when they exit the firm? Does this really happen?

I have some vested ESOPs. I want to buy the shares from a private company that granted the ESOPs. The ESOPs grant letter is paper based on company letter head. I wanted to exercise my partially vested options, I wanted to know a few things. Could the company play any delay tactics? Let us say I email them Today. What's ideally be the tentative timeline to excercise the options, given I have money to buy and hold the stock. If the valuation at moment is unknown, could it be bought at last known valuation?