Unexercised option after IPO

I’ve not exercised my ESOPs from my previous employer. I am waiting for the company to go public. I quit the company in 2021. What will my tax be if I exercise and sell my stocks at the time of IPO? How much tax can I save if I buy a property?

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.

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.

So say one has 100 ESOPs which a person exercised and converted to say 1000 shares in say Jan 2024 Now if IPO happens in aug 2024, what will be the long term capital gains tax rate for these shares. Will the tax rate change if one sells them say in Feb 2025, sept 2025 , Feb 2028 considering tax policy, tax rates to remain unchanged?

Primarily, my question targets startups which went ipo where you may joined when it was a private company and later it went public and you liquidates it. - will your esop units gets multiplied before ipo? - will exercise price gets increased before ipo? - what about the tax? - are there any unknowns and nuances involved which you were not aware of and later realised? I hold esops in a startup and want to understand how this works during an IPO

Please share the knowledge you've about these two!

Where did you work and how much money did you make? Asking as it looks like a lot of promise of ESOPs and wealth creation has failed employees in this bloodbath slow growth, layoffs, and job changes.

I have some ESOPs($17k total) at my current company(startup, initial stage), vesting over 4 years with a one-year cliff (25% vested after my first year, monthly after). I have completed 1.5 years here. I'm not sure if they're actually worth anything(no funding rounds since last 2-3 years, founder is saying he will raise in next 3-4 months), and I'm worried about the taxes when I eventually redeem them. Also I dont know about the redemption process. Could someone explain how this whole ESOP thing work, what the tax implications are, and where I can find more information? what all should I ask to my manager/HR as we dont have any portal/guide where I can see all these information. these are the questions I have rn how to track how much is vested? how do I redeem them? can I not redeem them this year, will they still be available to me in next financial year?

I had a very basic doubt. For people who've exercised their stock options or have had some similar experience with this in the past, what's best way to limit the tax liability? My company is registered in the US - would i have to pay taxes to both the governments? Thanks in advance and have a great day ahead!