For years, Timberland and hip-hop culture had an awkward relationship. One side—hip-hop— was all in. Artists have shown their Timberlands off at any and every opportunity for the past three decades. The iconic 6-inch yellow waterproof boot has been showered with love through name drops in popular songs, urban fashion, and all the free publicity that went along with it. Timberland reaped the benefits too. The company’s annual sales grew nearly tenfold from $68 million in 1985 to $638 million in 1994. In 1993 alone, the stock price rose 280%.

Timberland however, was reluctant to show the same love back. The Stratham, NH based company introduced the boots to the world in 1973 for a specific audience—the New England construction worker (or, as then CEO Jeffrey Swartz said in 1993, “Honest working people”). Even though artists like The Notorious B.I.G., Aaliyah, and Wu Tang Clan wore Timbs religiously, the brand did not embrace them with open arms. Timberland actually limited their distribution to curb the appeal from the largely black consumers who propelled the brand’s popularity. Despite the unprecedented exponential growth in sales, Swartz viewed hip-hop as a trend, not a cultural mainstay.

Fast forward to 2018. Timberland is much more comfortable being seen in public with hip-hop. Drake, Nas, and Juelz Santana have all released exclusive Timberland boot lines in the past eight months. The company’s performance has also skyrocketed in recent years since the brand repositioned itself. Jim Davey, VP of Global Marketing, said that the company’s resurgence is due to them directly targeting the “urban dweller who is only casually interested in the outdoors.”

What took them so long to capitalize on this opportunity we all knew was there? And how much more money could Timberland have made if they acted sooner?

Indecision led to repositioning

In the late 90s and early 2000s, Timberland started to dabble in urban markets with multicolored boots. Swartz was initially hesitant about the idea. Even though rappers like Cam’Ron wore pink Timbs often, Swartz still believed functionality was the core essence of the brand, and “pinkness” did not contribute to that. But while Timberland wrestled with functionality vs. fashion—which is hard to see as a problem in today’s apparel market—other companies jumped right in.

Reebok, which rebranded itself as “Rbk” at the time, began featuring rappers like Jadakiss and Fabolous in commercials directly targeted to the hip-hop consumer. These ads fueled sales for their Allen Iverson sneakers and Reebok Classics. A couple years later, Rbk doubled downed on the strategy by partnering with Jay Z and 50 Cent—two of rap’s alpha dogs at the time—on exclusive sneaker deals in 2003.

Steve Stoute, the music industry veteran behind the Jay Z-Rbk collaboration, spoke about the deal in his 2011 book, The Tanning of America:

“We should make a sneaker for the kid who doesn’t want to jump at all. He’s just going to stand still and look good in his sneakers.”

Both sneakers sold out quickly and performed very well upon initial release. The floodgates for hip-hop sneaker deals opened after that. Companies like Lugz, Nike, and Louis Vuitton were handing out sneaker deals to rappers like Oprah gave away free cars.

Instead of searching for the next artist to sign, Timberland was searching for its identity. The company tried to cater to the blue-collar worker, extreme outdoorsman, and hip-hop audience at the same time. Stewart Whitney, Timberland’s President, acknowledged the unclear strategy, “When you go after lots of consumers with lots of messages, the odds are higher for a misfire.”

This lack of strategy hurt the company. By 2007, Timberland retail stores were closing. Worldwide revenues continued to decline until 2012. The once timeless boot started to feel like it ran its course.

To fix the problem, the brand began a three-year market research study with over 18,000 customers. VF Corp bought Timberland in 2011 for $2 billion and gave them resources needed to conduct the study. The findings confirmed what many of us knew for so long—Timberland’s target customers are city dwellers who want footwear and clothes that have more style than purely outdoor brands. Since the pivot, the company made a strong comeback. The brand’s turnaround has been covered by several outlets.

A “Ryde or Die” opportunity

It’s great to see that Timberland is now promoting interviews with hip-hop artists and partnering with them on exclusive deals. But what if they launched this strategy 15-20 years earlier? And partnered with one of the most popular rappers at the time, DMX?

DMX in 1999 is a close comparison to 50 Cent in 2003: a hard-nosed New York rapper who wore Timbs, had a brief 3-4 year run at the top of hip-hop, and brought his crew along for the ride (Ruff Ryders and G-Unit, respectively).

According to 50 Cent, Reebok sold over 5 million G-Unit sneakers. At the listed retail price of $80.50 in 2003, that’s over $400 million in revenue ($80 million of that 50 says he made himself). Now let’s assume that DMX partnered with Timberland on a similar shoe deal for him, Eve, The Lox and the rest of the Ruff Ryders. Even if the Ruff Ryders only sold 1 million exclusive boots (a fraction G-Unit’s 5 million), at the $165 retail price for a pair of Timbs in 1999, that $165 million in revenue. If you spread that out across DMX’s four-year run, that’s over $40 million per year. In 1999, Timberland made $912.7 million in total revenue. It’s not unreasonable to think that a DMX-Timberland partnership could have increased company sales by 4%. In 2015, Puma had an 11.5% increase in quarterly sales soon after its endorsement deal with Rihanna.

Sneaker deals with music artists can’t last forever, as Reebok realized when it overstocked inventory for both S.Carters and G-Units and had to markdown prices, but the industry has learned from that. Rihanna’s deal with Puma is a sign of the changing times. “Puma has done a really good job of taking [Rihanna’s] sold out sneaker models and creating similar core items,” said Cam Wolf, a style writer at GQ (from an interview with Billboard). “So, she’s selling her own Fenty shoes, but the needle is moved in a much bigger way by Puma selling a more widely available approximation of her sneaker.”

Even if Timberland had done a limited release for the Ruff Ryders boots instead, they could have still made their $165 million (or more) if they took the Rihanna-Puma strategy and created similar boots.

It took some time, but Timberland finally figured it out. This wasn’t just about multicolored boots. Partnership opportunities became a rite of passage for the entire footwear industry. They now extend to complementary brands and major events that surround the culture. In February they released a limited-edition boot with New Era for 2018 NBA All Star Weekend, and last year they worked with Supreme on their 2017 winter collection. It’s a match made in heaven.

Believe it or not, one of these limited releases was with DMX. Here he is in November 2017, featured in a Timberland and Engineered Garments teaser ad to promote what looks like a rugged boat shoe.

These aren’t exactly the 6-inch Timbs that DMX and his fellow New York rappers made popular. To be honest, he’s dressed like the New England construction worker that Timberland initially targeted back in the day.

It’s not what I would wear to the cookout, but if anyone can pull this off, it’s DMX.