When to exercise employee stock options in a private company

Just this week, Dropbox joined the relatively short list of billion dollar "unicorn" startups that are going public. Only 26 venture backed companies of any size went public last year, and there are more than 100 US companies valued at $1b or more still sitting on the sidelines waiting to IPO. The ultimate question for the people who work at those companies is: should I exercise my stock options, and if so, when?

How much do I need to save?

I've been learning a lot about my own financial "standpoint" as I've been writing over the past couple months, and it's been an interesting process. One of the things that I have been thinking about over and over is the amount of money that I'm saving in comparison to my total earnings. How much is enough for me to retire in my early 50's?

I'm not #FIRE-ing but I am #FI-ing

The best part about personal financial is that everyone has a personal take on it. As I've been writing over the past three months, I've also been reading a considerable amount of material from other personal finance blogs. One of the things that's interested me the most is the #FIRE (Financial Independence Retire Early) movement. Since this is my personal, personal finance blog, I'll come right out and say that I'm not #FIRE-ing. Here's why:

A plan for selling stock options

The hardest part about being an owner in anything is knowing when -or if- you don't want to be an owner anymore. For anyone who has ISO or RSU stock options, you know what I'm talking about. If you sell your stock and it skyrockets afterwards, you locked in a lower price (and massive FOMO). If you DON'T sell, and it tanks afterwards, you are stuck with a bunch of nearly worthless stock.

What to look for in a startup

Go work for a startup! If you work in technology, chances are you've heard this advice, or you've thought about it on your own, or you're already working for a startup. In any case, I've noticed that there are tons of questions on Quora and Reddit and various other sites with people wondering how to find the "right" startup to join, which usually seems to actually mean "how do I choose a company that's going to make me rich." That's a little narrow-minded maybe, but it's reasonable to wonder how to find a company worth joining.

Can you remodel a condo?

It's much cheaper (and easier) to buy and fix up a $300k condo than a $600k house. Having just purchased a condo and renovated it, I can confirm that the numbers pan out, but it's easy to pick the wrong plac and end up losing money. No one wants to buy a $300k condo, put $50k into it and end up with a condo worth $325k.  Luckily, the right place can be fairly easy to find if you follow these guidelines. 

How to value stock options in a startup

One of the biggest challenges people face when evaluating job offers that include Incentive Stock Options is understanding how to value their ISO grant. In order to do that, you have to know how many shares you have, how many shares there are total, and a rough estimate for how much the shares are worth now. Let’s take a look at why, before we delve into how to find those numbers.

Setting a financial foundation

As I said in my welcome post, I’m going to try to skip the basic stuff in this blog. There’s no way I am going to be able to cover “setting up an emergency fund” any better than Dave Ramsey, or all of the hacks that emulate him. But… this first topic is something that would genuinely be useful for anyone. It’s certainly essential if you plan on saving and investing in any serious amount.