Twogler and ex-founder here - I ping-ponged from entrepreneurship to Google to entrepreneurship back to Google again.
I take the opposite approach, but with some caveats. Your financial success in any market is going to come down to information advantage - you need to have better data and better insights on the success of your investment than your competing investors. In general, you have much better data and insight into the risk factors and success probability of your own startup than you do into any startups you angel invest in. You also have better data on your own startup than you do on startups you work for, but probably have better data on how a startup you're employed at is doing than the investors in that startup do. Therefore you can make better choices about where to spend your equity (either sweat or monetary) when you're working for the company.
The major caveat - and one that took a lot of hard lessons for me to learn - is that you have to actually pay attention to that data. If your gut tells you it's not going to work out, cut your losses and find some other opportunity, regardless of sunk costs, how much you might be emotionally attached to the company, how much you love your coworkers, your fear of letting them down, etc.
But similarly, you also end up with a much higher-resolution model of the business world from actually experiencing work at several different startups than you would get from angel-investing in startups. So unless you've previously experienced worked at or founded startups, your angel-investing is basically going to be spray-and-pray, and do a lot worse than investing in your own company stock or even index funds.
I take the opposite approach, but with some caveats. Your financial success in any market is going to come down to information advantage - you need to have better data and better insights on the success of your investment than your competing investors. In general, you have much better data and insight into the risk factors and success probability of your own startup than you do into any startups you angel invest in. You also have better data on your own startup than you do on startups you work for, but probably have better data on how a startup you're employed at is doing than the investors in that startup do. Therefore you can make better choices about where to spend your equity (either sweat or monetary) when you're working for the company.
The major caveat - and one that took a lot of hard lessons for me to learn - is that you have to actually pay attention to that data. If your gut tells you it's not going to work out, cut your losses and find some other opportunity, regardless of sunk costs, how much you might be emotionally attached to the company, how much you love your coworkers, your fear of letting them down, etc.
But similarly, you also end up with a much higher-resolution model of the business world from actually experiencing work at several different startups than you would get from angel-investing in startups. So unless you've previously experienced worked at or founded startups, your angel-investing is basically going to be spray-and-pray, and do a lot worse than investing in your own company stock or even index funds.