Maximizing Your After-Tax IPO Returns
Have you recently received a windfall? Perhaps from an IPO? AMA Finance is here to help diversify your holdings in an optimal manner, sometimes even before your IPO lock-up has expired, drastically cutting risk.
As this is a somewhat niche problem, traditionally it's been hard to get solid help. Few sources cover high-capital gain windfall management; financial advisors and banks, lacking baseline knowledge, either cannot offer appropriate services or charge high fees that don't make sense unless you have over $5M.
When I gained an IPO windfall, I had to solve it myself -- AMA Finance is a product of that knowledge.
This website aims to educate you about how to maximize your risk-adjusted, after tax returns -- Following this advice can save you potentially hundreds of thousands of dollars. The guide (the top navbar) is broken down into three sections:
Hi, I’m Aaron, creator of AMA finance.
In my prior life, I was a staff software engineer at Dropbox, designing and building high complexity software.
Shortly after Dropbox’s IPO, I left the firm. With the majority of my net worth in Dropbox stock, and already having written some posts involving financial modeling, I invested heavy time studying financial modeling and tax laws to find the correct balance between risk and return.
Taking what I learned, I took out a couple personal loans, and used the proceeds to hedge my Dropbox stock during IPO lock-up, taking advantage of some irrational price spikes. While I concede a probabilistic model’s accuracy cannot be judged from a single test, for those curious, this hedging allowed me to ultimately dispose my stock at a price significantly higher than was possible post-lock-up. I additionally was able to significantly minimize my tax burden with the various strategies detailed in the above guide.
Remember, I’m not a lawyer, CPA or investment adviser. None of this information is intended to provide legal, tax, or financial advice. This information is intended only to assist you in understanding rules and is broad in scope. I do not put any guarantees on this information and are not liable for any action you take or fail to take based on information that exists on this site.
Credits to Nils Bunger for much of the initial design of this website, as part of our project to value Roth IRAs.