Context

• 39 yrs, married and have 2 kids. wife used to work in tech but opted out to focus on the kids
• live in Canada, no property here. sold a condo earlier this year, got a hit of $125k CAD due to the market situation
• my family lives in tier 1 - have a mortgage free 1 bhk
• her family in tier 3 city - built a decent home (about 75 L) last year
• both families' monthly expenses combined are 1.5 lakh

Problem

• I work in a startup and joined at series B. $10 B valuation, going IPO next May for sure
• got stock options which are worth $3 mil USD right now
• went on pat leave for 6 months. was put on PIP after 1-2 months of returning
• If I resign or laid off - have 3 months to exercise my stock options
• was thinking to anyway retire and work on invest in farming (wife's family is of farmers, not rich but just everyday farmers)
• but the catch is I need to pay tax on exercise - $1.5 million CAD
• I don't have this much money lying around but saved $600k CAD
• have additional $300k CAD from property sale
• considering IPO could give me a profit of 20-30x (at least, can be more) --> so in INR could be 30-40 cr (post tax)

Question to y'all

• should I put all of my money in exercising stock? - upside is I get all the 20-30x
• should I take out only half from savings while other could be from financing? - hedge the risk, but give out almost 40% of the profit to the financing company (ESOfund.com or SecFi.com)
• should I start looking out for jobs (2-3 recruiters reaching out every month but I haven't replied back)? considering there's always a risk of IPO not happening or going bad?
• what would you suggest?