Retiring Early

Saturday, September 23, 2006

Career crossroads...

I've been thinking about this for the past 6 months or so. Although I've recently moved on to a new project at work, I can't help but feel less than passionate about it. Additionally, my entrepenurial leanings are showing themselves again and my feet are getting itchy! From that perspective, I'm thinking about leaving my current company for a web startup environment. Since I'm already in high-tech, this isn't a stretch for me, but I am carefully considering the risks, especially with respect to the early retirement plan. It could accelerate my plan or put a large dent in it.

On one hand, I am leaving a significant portion of yet-to-be-vested options on the table as well as a good salary, great benefits and the security of a larger tech company. On the other hand, I should be able to match my salary and benefits, and hope to get a significant equity deal in the new company to help offset some of the money left on the table. The risk is obvious -- money waiting to vest vs. a hard to realize amount of company equity. There are obviously a lot of other dimensions to the decision, but from a retirement perspective, these are the key financial aspects. I really believe in the mission and founders of the the company I want to work for and it has significant funding, a great product and a lot of buzz. For me, that helps mitigate some of the risk, but it doesn't alleviate it entirely.

Has anyone gone from a large tech company to a startup in the last year or so? If so, I'd love to hear some thoughts...


  • At 10/11/2006 9:38 PM, Blogger pfstock said…

    It has been a while now. Have you decided on which path you will take?

    Your blog reminded me of an article that I read in the August 1999 issue of SmartMoney. The article, "Retire Ten Years Early," profiles Don Powells who was a technical writer for Microsoft. He retired at age 38 when his stock options vested. Maybe you can relate to this story...

    Good luck, whatever you decide.

  • At 10/12/2006 7:46 AM, Blogger fin_indie said…

    Good question. I should make a follow-up post on this. I have not made a decision overall, however, I did interview with a few startups and found that the salary hit was on average a whopping 1/3 cut in salary. I think the companies I talked with were expecting me to take the risk of a lower salary in hopes of a successful ipo or the like. That wasn't something I was comfortable doing considering the large risk and considering my early retirement goal.

    That said, I will continue to look for opportunties, however it really needs to be the right opportunity for me to take it.

  • At 10/14/2006 9:00 PM, Blogger pfstock said…

    Over my career, I've worked for large companies and small companies. I too have interviewed with a few startups, but never took a job at one. Generally the smaller companies claim fewer resources, which means that they'll offer you less in compensation. Compared to a large tech company, a startup will give you a broader responsibility, which usually translates into longer work hours. Do you feel OK with that?

    On the subject of pre-IPO options that you may get, that is a tough call. You'll have to really think hard about it. I don't want to influence your decision there, but just advise you to consider things from all angles.

    Since you are from Washington state and work for a "large tech company," I have a hunch that I know where you are. I assume that large=huge. Staying with that is the conservative, safe option. But, it probably won't hurt to at least consider other opportunities.


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