It's a matter of knowing your audience and knowing your funder's/owner's goals and expected risk-reward trade-off profile. A "cowboy" mentality may indeed help

It's a matter of knowing your audience and knowing your funder's/owner's goals and expected risk-reward trade-off profile. A "cowboy" mentality may indeed help a start-up edge out competitors. But applying that to an established company can ruin your reputation: you have more to lose by playing fast and loose. Startups by nature are a gamble, but if an established corporation gambles too often they may poke a hole in their dam that they can't patch fast enough. Venture capitalists usually factor in a high failure rate to startups they invest in. Their plan is that enough will succeed in a big way to counter the high failure rate. A lot of "fads gone wrong" happen when a technique or technology that works for one situation or size is misapplied to another. Your office printer inventory tracker doesn't need microservices and web-scale databases. Pilot projects with new technology is often a good thing, but don't bet key organizational functions on such a project (sometimes called line-of-business systems).