(My rule of thumb, which I've back-rationalized onto my career, is not to start back-to-back companies).
It also shows you that there is more than one path to success. I've worked for several startups and each one taught me a different way of thinking about what are the important things to focus on, what kind of people to hire, and what problems are worth solving.
It wasn't until my fourth start-up job that I found one that I loved and stuck with for more than 1.5 years. Luckily, that one worked out and I was rewarded for it. Not as a founder, but as the GP recommended: work at it and find a key role. Work up from there and get your efforts recognized.
You won't make millions this way but you will learn a lot about business--mainly, how to recognize the good and bad things in your environment, and how to navigate those issues. You also don't have to risk your savings or livelihood. Unless you have a clear or novel idea about what you want (which I didn't), it is a great learning environment.
One thing that I have always known is that I'm not a natural business-type person. After having the safety blanket of learning through 6 years of funded start-ups, rather than on my own dime (and thinking I could do it myself "because it's so easy"), it really helped my long-term prospects of running my own business. One day I will but not yet.
This is bad advice. You should stop giving it.
Edit: FYI- he had mentioned working for an unsuccessful startup would torpedo your career.
The rationale is that if you don't know what the boss looks like to an employee, you won't know what to do as the boss.
I definitely consider myself an early-stage startup guy, and I am extremely hesitant to work for a large company, however I've actually only been in a true startup for 3 years out of a 12-year career. Before that I worked for a public University, a new media agency, and a bunch of small freelance gigs. In all of those circumstances I was able to do great work, meet great people, and learn a lot about business (yes even at the U).
Now it's true that nothing matches the ambition or intensity of a true startup, and it's definitely a place I like to be. Conventional wisdom in silicon valley evolves quickly, but it's very inbred, and it tends to create bubbles of competition around sexy concepts, where hundreds or thousands of the very smartest people in the world are working 18 hour days on some specific concept that doesn't even have a market yet (eg. Check-in-base mobile apps). Meanwhile, out in wider industries you find huge markets with huge inefficiencies due; billion dollar markets that are ripe for disruption, with reasonably small barriers to entry for someone with a little inside information.
If you bring your technical and execution skills to one of these markets you have a much greater chance of success, and with an established market you also can be sure there's something really there. Spending a couple years in an established company could be the seed to a brilliant startup. Likewise, working on yet another social widget just for the sake of being in a "startup" could land you with obsolete skills when app-fatigue turns to backlash, and silicon valley moves onto the next hot thing.
Without this belief that what you are working on will be the next sliced bread, it can be easy to get discouraged or, as you mentioned, move on to the next project.
Thinking that you're going to win by just playing one or two hands is dumb. I also don't like the view that entrepreneurs do it because their personality naturally gravitates towards risk, that's just not smart business.
Only way to win is to take advantage of high EV moments in life, but to also maintain a long-term view and mitigate risk along the way so you can keep playing the game for as long as possible - survival goes before anything else.
Max Levchin failed 4x before he hit it with PayPal. No one becomes a great entrepreneur overnight.
Be ready to seize opportune times, but never risk disaster. The world's greatest entrepreneurs and investors didn't get to where they are today with diversification strategies.
They did it by concentrating the bets they made in life.
In this case, what you need to succeed depends largely on having the right set of skills to succeed within your specific domain, assuming you have one. I'm generally of the opinion that there is much lower risk in these areas (assuming you know your market well) since presumably all you have to do is match an existing need with a product, the primary barrier being your competence.
How do you acquire the skills necessary? This too depends on which side of the ball you are on. Larger startups need people in different roles. Rather than getting in on a little startup and being part-time coder, part-time cleaner, part-time ramen cook, get out in the would and be the most excellent in whatever facet you excel in. Heck, you may decide that making the world a better place in whatever capacity you are best at (usually also what you enjoy) you is better than attempting getting superrich and retiring at 30.
In other words, my advice to all "startup" people out there is do what makes you tick, do it as best as you can, and let your startup, if it arises meet a need that you know is real. This may be a problem that people don't realize is a problem (like limited and often unintuitive course management software) or it may be something bigger and better that only a few people will understand (e.g. a cure for Multiple Sclerosis).
Anyways, I've nothing against serial entrepreneurs if that's what makes you tick. More important though is do what you love.
"Cloud" in this context is an opportunity cloud, the sum total of all the positive things that can happen to you at one particular moment. It is what happens when you position yourself to be in a spot where good things happen, not knowing exactly what.
This is a different strategy than the "ladder" strategy which basically is about climbing a corporate career ladder.
When you're in "startup mode" you constantly try to expand your opportunity cloud but you don't always know the direction. It's a completely different way of thinking compared to the ladder.
I've been exceptionally lucky in all of these aspects, so I've been doing nothing but startups since then (except when I found myself at a big company post-acquisition).
If you're going into it just to get rich quick, you are definitely doing it wrong. And your motivation is sufficiently off-course to pretty much guarantee that you won't get what you want.
What I missed though and what I've realized since is that if you actively engage in that community you end up meeting people that end up helping you that you would otherwise never meet because you can't justify meeting them with your head down all the time.
So it ends up being sort of non-intuitive, and hence the post. I think if you do relax that mode a bit your chances actually go up. Of course there needs to be a balance though.