I might go for that in a tech company... a small idea can go viral and amplify it's value by orders of magnitude in months.

But an airline??? Which is in a commodity service industry? Equity valuation will be a long, slow plodding march, set back as costs gradually rise and the competitors start resisting your encroachment. Always with the risk of a big downturn wiping you out. Gonna depend on timing and luck frankly. Almost might as well go to Vegas, at least you know if you won or lost right away.

IIRC a few people did make out that way with SW and maybe B6, so not impossible but it doesn't seem like a great personal financial plan.