Choosing between two job offers

Although my eventual goal is #FI, I derive the largest part of my income from good old fashioned American work. Actually, it's new fashioned American techwork, complete with standing desks and kegerators. I've got it pretty good but I'll have to move on and choose between job offers someday.

Using debt as a forced savings plan

I’ve repeatedly seen two narratives told over and over again. First of all, debt is bad. Second, although debt is bad, having a mortgage is alright because it acts like a forced savings plan, slowly enabling borrowers to build wealth. But can't the “forced savings plan” idea can be extended beyond simply mortgage debt, if executed intelligently with low interest, short term debt?

I'm exercising my ISOs on Monday

Good morning everyone. Today is a BIG day for me, and a big day for my investing strategies going forward. I'm exercising around 1/4 of the options I've been awarded in the startup I am working for. Although this won't have a huge impact for me in the near term, over the course of the next 3-4 years I am hoping this single decision will save me thousands of dollars (or if I am really lucky, tens of thousands) in taxes.

Turning recurring expenses into recurring investments

Life is expensive, and that can make it really hard to save. With rent, cell phones, cars, healthcare, food, childcare, vacations and thousands of other little costs, it’s not unusual for someone to have 80-90% of their income disappear into the ether. Lately, I’ve been thinking about ways I can try to turn at least some of those recurring payments into recurring investments, or at least mitigate them so I don’t lose so much of my income to recurring expenses each month.

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: