When I tell you that the lottery ticket I'm giving you is a winner, you probably understand that it is only a winner if the numbers are drawn at the correct time. You might ask, has the draw already occurred? (knowing that to be the critical feature) and I would either say "Yes" and you would know that I was literally accurate in my statement, and if I said "No" you would know that I was probabilistically accurate in my statement. You would then act in your own self interest based on your understanding.
So if I'm a founder and tell you that the company I'm trying to hire you to come work for is going to be a huge success. You might ask "What are your current success metrics?" or "How much revenue do you have?" And based on those answers you could tell if I were speaking literally or probabilistically.
The "interesting" (from the philosophy point of view) is the statement "This lottery ticket is a loser" is just as much as accurate as "This lottery ticket is a winner" because the operation is binary.
For every startup (or company) I've ever been in, or recruited people to come work for, I've been very clear about what is the upside and what is the downside. And generally people understand that. And I have heard people (and people have pitched me) with outrageous "sure bet" sort of things. Which I have politely, and respectfully, picked apart at the places where I have concerns. The most recent was last week when I listened to a pitch for a new product idea to connect people and jobs. I idea is really clever, if you have a critical mass of people who are looking for jobs and people with jobs participating. But there is a huge gap between the world of today, and the world where all those people are participating. If that person wanted me to believe that there was any chance it was going to be a huge success, I would have to believe they could get a critical number of people on board. They don't yet have a way to do that, so I don't yet believe they will be successful. They are completely honest and forthright about the potential success, once they have critical mass, so I don't consider them to be lying to me when they say it will be a huge success. I just know that they don't yet know how they are going to get there.
The original article was a sort of 'wake up sheeple' sort of call to action but I felt that was completely unwarranted. Sure there are some new folks who, in their first job, might feel like the possibility to suddenly be a billionaire is just around the corner. Just at one point they may have believed that all college courses are trivial. But experience teaches us to think, and when we think about startups we have to think critically about the likelyhood of various scenarios coming true or not.