Employee #40 at a medical device company after working as a contractor for one year and then asked me to join. Received a first round of ESOP options a bit unde

Employee #40 at a medical device company after working as a contractor for one year and then asked me to join. Received a first round of ESOP options a bit under the valuation price ($20 at the time). Then RSUs as bonuses for the next 5 years. After company started to ship, shares went up and even reached over $100 at one point. Sold half of my stock between $70 and $90 and made around $450k before taxes. We were partially lucky that those were the recession years and investors were looking to put their money in less risky ventures, and as far away as possible from real estate. I quit a couple of years before the company got bought by a major player, leaving my remaining unvested stock which would have been worth another $300k at the moment of the acquisition. Good money for me as my first job in the US, although not as good as a bunch of colleagues before me that were turned into senior management and made millions. Loved the job, and I would have stayed if they hadn't assigned me a new boss that, albeit not a bad person, his professional demeanor was awful. Have worked for 3 other startups since then. The next one, also a medical device company, looked promising. Joined as their first contractor/employee but I could not secure equity. They also changed directions on their development so I left. Salary was not terribly low but half of what I usually make. They are currently supposedly doing well and are shipping product after 5 years, and received around $30M funding mostly from a Silicon Valley VC last year to accelerate their growth. I know other employees left after me for similar reasons. They got compensated even less than me. The following one again as a first contractor/employee in the connected home space with some promises for equity if the company soared (founders had done that before and were successful, with strong ties to Apple). Salary was not superb considering my skills, but above market. However after 2 years the founders could not do a buyback and the company was absorbed by their single investor, a big security business that was just in the process of rolling their IPO. They only offered us employees options at market price with a lot of restrictions. They were also going to reduce my salary and obviously I didn't like the terms. Currently almost two years at a SF startup, with all the pains of working and living in the preposterous SF zeitgeist under a small startup company salary. Own more than 1% of the company but I know it will get diluted after we receive our series A, and where I don't have much control of the circumstances. Before all these deeds, founded my own startup with a friend right out of college, mainly building industrial systems. We were naive and business inept, never made serious money but managed to stay alive for five years doing some cool customer projects, having fun and learning a lot. Plus the gratifying feeling of having control over our destiny, even if it was a bit for a small period of time. Hands down one of the best experiences of my life. There is a reason startups - technology startups in particular - are declining in number, specially in the US. The field is too mature, consolidated and institutionalized now. There are some niches and pockets of opportunity, however competition is intense. Sadly most affairs and regulations are rigged against employees, and if you are not being compensated at market level with all the associated perks, you will never get rewarded as you deserve as an employee compared to a founder or investor in the minuscule event that the business is successful. If you really want to be part of a startup, first try to work at a FAANG type of company even if the idea does not appeal to you. Leverage their massive resources to learn and grow your wealth. Save enough to a point that you are comfortable and don't need to worry about money anymore, whatever that means to you. Then, and only then, if you still feel the need to scratch your entrepreneurial itch, make your move. The full monty - not as an employee but a founder. Your increased experience and business network will further increase your chances of success. And you will also have come across real industry problems that desperately need solutions. Win-win. In this age where work is changing so fast and the future of security for workers is uncertain, hoping for the best and planning for the worst has more relevance than ever. My 2c.