Coming up to the end of several years of vesting after an acquisition. The acquiring company has been absolutely awesome and fun to work for, but its nothing like being in complete control of your destiny as a startup founder. You have a boss, you have smaller aspirations, its impossible to have as large an impact, and you have to push through lots of people to try new or risky things. The best you can hope for is a non-dysfunctional and creative organization, and I've been extremely lucky to have joined one. But I still miss the wild west of the scrappy startup phase, there really is nothing like it. PG's post about humans in their native habitat is spot on. You remember very quickly what it's like to be a caged animal when you are acquired.

That said, I think the author of this post is glossing over a major point.

When you're doing a startup in your 20s with essentially zero net worth, you're taking a massive risk. If you get sick, if your family members get sick, if you end up busting up your car, if your landlord throws you out, and so on, could all be complete disasters. Of course, you (generally) know this going into it but the reality is most young first time founders are dancing on the edge of disaster, on all fronts. (As I was) I know you're supposed to be financially secure before you start a company, but in practice this means 6-9 months of living expenses, and you still are one or, if you're very lucky, two disasters away from total ruin. If you want to be successful, you almost have to jump in when it feels dangerous to do so, because if you keep delaying for safety you'll never make the jump as your standard of living rises to meet your salary and so on.

Now, after an acquisition and the admittedly grueling process of going through a payout schedule, I am of the mindset that finally getting to a solid payout is going to be a life changing event for me. No, not because I will buy fancy cars or go on lavish vacations. In fact, I expect my standard of living to decline as the low-risk returns I expect to earn on my payout in the markets will result in a virtual "pay cut" for the time being as I prepare for the next adventure.

But what it will mean is I can have another thrilling startup experience (for all the reasons most people do it) without all of the truly scary, risky, life-endangering consequences. Sure, the startup can still fail and I can waste my time. Sure, I will still need to think frugally. But if disaster strikes, I (or my loved ones) won't end up bankrupt, on the streets, or dead. Also, until I jump back into the game again with a solid team and idea, I will be free to experiment and pursue where ever my curiosity leads me in finding that idea without the pressure cooker of "maybe I should start doing consulting again soon to pay the bills."

I haven't gotten quite to the finish line yet, but I have to imagine it will be a very liberating feeling, as long as I have a clear perspective on what exactly money can and cannot do for me, and how I should take advantage of the opportunity of having a few million in the bank. For me, its about freedom from having someone control my life, and removing the ambient risks life has without financial security, not about material things or indulgences. I'm so happy to live in a country where having one lucky break of an exit of a few million dollars can bring about this type of freedom if acted upon wisely.