In the late 1970s, when I was eight years old, I fell hard for Kenny Rogers’ existential country hit, “The Gambler.” Up to then, my idea of a great song was “Would You Like to Buy an O?” from Sesame Street. But something in me had shifted, and I was primed to have my mind blown by a three-and-a-half-minute dose of countrified Kierkegaard.

You probably know how the song goes: “You gotta know when to hold ’em, know when to fold ’em, etc.” Though the lyrics may be a bit hokey, its basic “time enough for counting” analogy still feels universal—even when stretched to make a marketing metaphor. Because as every marketer knows, it really is about knowing what to throw away and knowing what to keep.

Take outdoor retailer REI, a brand that’s taken some risks over the past few years. It’s Opt Outside campaign of 2015 was built around an idea—born from a brainstorming session—of closing all of its stores on Black Friday. The campaign invited employees and customers to “opt outside” rather than spend the day indulging in knee-jerk consumerism.

The crazy idea quickly won over the marketing team and the CEO. More important, it won over the public. Opt Outside was a huge PR success, and though a bump in sales wasn’t necessarily the goal of the campaign, it probably didn’t go unappreciated. (REI, which is a member-owned co-op, also saw its membership increase in the wake of the campaign.)

REI’s move toward long form content is another leap of faith that’s paid off for the brand. The “REI Presents” series of documentary videos are light on REI branding and long on real people making emotional connections through outdoor living.

REI’s believes longer documentary videos like “Paul’s Boots” and “The Pleasure and the Pain” can make a deeper connection with potential members and customers—one that may not pay off immediately, but supports the growth of the brand. According to Eric Hess, REI’s content marketing program manager, it’s not about a sure thing, but rather trusting that what you are offering has inherent value: “We’ve seen that when you approach all stages of the customer journey, you really are effectively building that brand, building that relationship, building engagement. And having a much more deep and meaningful relationship with your customers than when you’re only talking to them for short periods of time at a very specific point in their sales journey.”

And for those who (despite the Gambler’s advice) do their counting at the table? The REI Presents videos have racked up impressive numbers of views. “The Mirnavator,” about ultra-runner Mirna Valerio’s persistence in the face of fat-shaming, has seen nearly a quarter of a million views since it was posted just two weeks ago. And REI’s “Mirnavator” Facebook post has been shared more than 40,000 times in a week.

Taking a gamble doesn’t have to be about big ideas and deep relationships. Sometimes it just means playing a hunch. Back in 2011, some weird but wonderful Old Milwaukee commercials starring Will Ferrell started appearing in small Midwestern markets: places like Davenport, Iowa and Terre Haute, Indiana. A separate spot appeared during the 2012 Super Bowl, but only in one market in North Platte, Nebraska. According to Old Milwaukee, the ads were Ferrell’s idea, and he did the spots for free, out of love for the beer. Whether or not that’s strictly true, the execution of this oddball campaign relied on many people, inside the company and out, saying, “Okay—why not?”

Putting happy accidents to good use can also be a smart bet. Consider this recent Instagram post to promote The Shins’ appearance at the Greek Theatre in Los Angeles:

We’re doing the LA Greek y’all! 9/29 ⚡️💥🚀

A post shared by The Shins (@theshins) on

If you’re going to take a flyer on any aspect of your business, isn’t your marketing the place? As any star will tell you, the public’s memory is only as fresh as your latest hit, or your latest flop. So long as you’re not completely reckless, there’s at least the chance of winning big.

Every hand’s a winner, and every hand’s a loser. But you can’t become a truly great gambler, or do truly great marketing, if you never go all in.