Interesting. You can see this direct observation with the actions of any child who randomly practice and play with things they encounter to create or do something new. Older, wiser people with years of experience are either bored and see no advantage in play so they don't. Only to realise later that they should have tried this earlier. Is this a natural adaption process that adults outgrow? Is this process a non-optomised way for chance discovery and improvement?
There is also a dark side. Experts are experts for a reason, conservative competence. You don't want your accountant or lawyer advising you on something using trial and error techniques. The lack of experience in some skill-sets will also cause startups to fail ( #14, Poor investor management ~ http://www.paulgraham.com/startupmistakes.html ). Successful entrepreneurs need to harness playfulness and hope their lack of experience doesn't cause them to fail. Serial entrepreneurs turn the playfulness on or off when required or find alternative strategies to plug areas they don't their inexperience into failure.
Maybe thats why a few grey heads are sometimes an advantage in guiding startups?