All generalizations are just that. I don't think he was saying that anything is impossible. A first-timer could also raise if they had great luck (bumps into the RIGHT investor), great connections, great salesmanship, great pedigree (went to Stanford, worked at Twitter), etc.
He's saying that first-timers (generally!) have pretty crappy odds of closing quickly, with good terms, and with top-tier investors.
I don't disagree with the difficulty involved, I think that's prominent in any attempt at starting a business.
I believe the odds / luck factor can be substantially altered in a favorable way by having at least an above average product to show off, combined with a vision for where you're going to take it.
Most good investors will spot very quickly whether your product is crap or not; they'll obviously size you up based on what you say, how you act, your confidence in your product and vision for it, and so on. If you have it, they'll see it, but you've gotta have a product to show off and you have to speak confidently to where you're taking it and how. You've gotta sell the investor on you + the product + the future.
Do those things, and any investor worth having will take notice regardless of your background or traction.
If you have an "above-average product to show off", the first question any investor is going to ask is, "how are people liking it?". If you have a lot of satisfied users, you have traction! If not, having the completed "above-average" product does two bad things:
(a) it gives the investor an easy "out" ("let's work on getting you in front of users and see how that goes"), and
(b) it creates a signaling problem ("great looking product; no paying users; what's wrong with this idea?").
All that aside, I've done the VC tour a couple times, once in the first bubble and once out of it, and my experience has been that without a thrumming business already built, it's all about your track record. If you've made money for investors recently, they'll pay attention. Otherwise, they'll string you along.
Sometimes people get lucky. It's possible to flop 7-7-2. That doesn't mean it's a good idea to go all in on pocket 7-2. Courting investors is tremendously expensive. It probably does make some sense to divert some or all of that effort into building up a business instead.
He's saying that first-timers (generally!) have pretty crappy odds of closing quickly, with good terms, and with top-tier investors.