If you regularly use rideshare services like Uber or Lyft for transportation in New York, Los Angeles, Nashville, Miami and other key music cities, you've probably noticed that the "rideshare side hustle" is alive and well. More and more cash-strapped artists are driving for Uber and Lyft to fund their passions and careers, drawn to the gig's flexible schedule while often leveraging each ride as a unique networking or performance opportunity.

Recognizing this distinct community, which numbers in the several thousands, Lyft decided to give back to a select cohort of lucky artist-drivers. In honor of its entire driver base accruing over $500 million in tips to date, the company's Miami office partnered with Demi Lovato to give four drivers free studio time at local upscale recording outfit Studio 26, as well as free VIP tickets to Lovato's show on Mar. 30 at the AmericanAirlines Arena.

Last month, right around Miami Music Week, Lyft sent out a cryptic call-to-action to local artist-drivers to audition for an on-camera commercial in front of senior Lyft execs, to be filmed at the Gibson Guitar Showroom. The company eventually chose four winning drivers, based on their commitment to music and on their personal stories, and sent them to Gibson Guitar -- not telling them that they would have the opportunity to meet and perform for Lovato, who was waiting for them inside. You can watch excerpts from their encounters here.

Interestingly, one of the winning drivers was Jarae Womack, whose name might sound familiar because of her royal R&B and soul heritage: Bobby Womack, who hit the Billboard Hot 100 multiple times in the late '60s and early '70s, is her uncle, while legendary “King of Soul” Sam Cooke is her great-grandfather.

Yet, Jarae Womack has struggled to achieve a similar breakthrough: she was formerly signed to Universal Music Group subsidiary SoBe Entertainment, performing as Ja'Rae, but parted ways with the label before she even got to release a full-length album (and she's not the only artist with an ill-fated SoBe deal behind her). She began driving for Lyft to help make ends meet, and often found herself on the verge of giving up a singing career -- but was encouraged by her passengers to keep pushing.

“I’ve moved back [to Miami] from Atlanta, to give my music one more shot!” Womack wrote in her submission to Lyft’s call-to-action, provided exclusively to Billboard. “Lyft is helping me provide for my son! I am a single mother who will not give up on her dreams! God’s plan.”

The other winning drivers include bassist Jermaine Walden, who's driving with Lyft in part to cover the costs for his wedding this coming July; Conrad Clyde, who is both a musician and a filmmaker and drives with Lyft to help save up for better camera equipment; and Eric Monterossa, a producer, songwriter and musician who wrote in his submission that “Lyft helps me make financial ends meet and maintain a versatile schedule, so as not to miss out on any opportunities.”

Lovato already had an existing relationship with Lyft prior to this activation: in summer 2016, the singer took part in the “Undercover Lyft” campaign, driving around Denver, CO in disguise as "Sam," a fervent fan of Lovato and an aspiring musician. Partnering with the company again in Miami for a more rewards-oriented activation this time around seemed like a natural next step.

“I was inspired by these four amazing Lyft drivers, and am so lucky to have had the chance to get to know their personal journeys and make it that much easier for them to pursue their love of music,” Lovato tells Billboard in a statement. “It’s always been important for me to use my platform to help and inspire others, and giving these talented Lyft drivers the opportunity to continue to make music and encourage them to follow their dreams meant the world to me.”

This is not the first initiative Lyft has facilitated to help local musicians. In Dec. 2017, the company launched the Austin Musician Rideshare Program, partnering with local venues including Empire Control Room, Antone’s, Stubb’s, Mohawk, Barracuda and Cheer Up Charlies to distribute Lyft ride-credit codes to local musicians prior to their gigs. While the timing may have been in part a promo for SXSW -- Lyft was SXSW's official rideshare partner in 2018, and SXSW is Lyft Austin's biggest week of the year operationally, generating an average of three times the normal earnings for drivers -- the program is currently slated to continue indefinitely beyond the annual festival cycle.

More importantly for Lyft, however, Uber isn't far behind. The rival recently partnered with three Best New Artist nominees for high-profile TV commercial campaigns during the 2018 Grammy Awards, and gave back to aspiring artists in 2015 with its #UberBigBreak campaign in Nashville, in which local singer-songwriters could use the promo code "BIGBREAK" for the chance to win an in-person audition with senior execs from Warner Music Nashvile, the Country Music Association and other similar companies.

In fact, Uber might have a stronger reputation and history than Lyft when it comes to drivers leveraging rides as performance opportunities. Jonathan Guarano, who currently works as head of video content & influencer partnerships at beverage company Hint, famously recorded a series Carpool Karaoke-style videos with his Uber passengers that landed him a promo deal with The Chainsmokers and a free flight to Toronto to meet The Weeknd in person. Daynel Artiles, who makes music as Artdayn with NYC-based Bentley Records, encouraged his passengers to film him singing for them and post the videos to social media with the hashtag #singinguberdriver.

From a hiring perspective, both Uber and Lyft are also increasingly recruiting talent from the music business. Lyft execs Becca Lawson (vp of brand marketing) and Melissa Waters (vp marketing) previously worked at Pandora, as senior director of brand marketing and vp of brand & product marketing, respectively. In Jun. 2017, Uber sent ripples through both the tech and music worlds when it tapped Bozoma Saint John (former head of global consumer marketing, Apple Music) as its new chief brand officer.

Facing ongoing criticism and skepticism around issues like driver compensation and corporate culture, rideshare companies are understandably look to music and entertainment veterans with a knack for long-view, digital storytelling that sends more positive messaging to users. Uber has been suffering an ongoing series of PR disasters over the last few years, from which Lyft has somewhat benefited. According to a recent survey by popular blog and podcast series The Rideshare Guy, 76 percent of Lyft drivers reported that they were satisfied with their driving experience in 2018, compared to just 58 percent for Uber.

Both companies are trying to revamp tarnished impressions around ridesharing by focusing less on the utility and convenience around hailing a ride, and more on drivers' personal journeys and on moments of generosity, gratitude and emotional connection between drivers and passengers that are arguably harder to quantify with dollar amounts. Several Lyft drivers in particular have even reported receiving free VIP tickets and guest list spots from passengers to concerts by the likes of Jay-Z and New Kids on the Block -- without any intervention from Lyft.

“There is an absolute magic that happens in a Lyft every time a rider shares a ride with a driver,” Lawson told Adweek in May 2017. “Our drivers prefer Lyft passengers, who prefer Lyft drivers. It’s all about the connection and community that happens in that car.”

Aside from a more positive brand reputation, Lyft is also trying to compete with Uber for music partnerships using a tech platform with meaningful reach and cultural influence. In the near future, the former might even be taking a tip from Spotify and launching its own paid-subscription tier for rides, cementing its potential to become both a widely-adopted utility and a captive media destination.

“Eventually, the majority of miles traveled in the United States will be on a network like Lyft,” Lyft president John Zimmer told Bloomberg earlier this month. “You’ll be subscribing to a Lyft transportation plan similar to how you have a music program, maybe Spotify, or a minutes plan like you have on AT&T or Verizon.”

In Sep. 2017, Lyft became one of the first companies in Silicon Valley to collaborate with Cardi B, crafting an in-app release campaign in which riders in New York could enter the promo code "BardiGang" to add the artist's face and signature nail designs to the skin of the app, the weekend before "Bodak Yellow" topped the Hot 100.

Only 13,000 New Yorkers ended up using the promo code -- a paltry figure compared to the two million followers Cardi B has on Spotify, but still a potent number for Lyft when it comes to fan engagement.

“Our goal in working with artists is to enhance the fan experience and offer artists a unique platform to share their music -- whether that’s providing safe rides to and from shows, creating a custom artist-themed in-app experience, or producing entertaining content that can help promote an album, single, or tour,” Austin Schumacher, head of culture & entertainment at Lyft, tells Billboard. “We want to give our passengers and drivers memorable experiences, and we have a sizable network to help share an artist's message.”

With regards to transparency and driver support, Lyft's $500-million tipping benchmark highlights how the company was the first in the rideshare world to offer in-app tipping and same-day payments, and also provides fuel rewards, retirement solutions and tax support to drivers through its Accelerate rewards program. To date, the company has also been more transparent than Uber around rider pay, revealing last week that the median salary for Lyft drivers after the company's usual cut was $29.47/hour nationally and $31.18/hour in top-25 markets (including time spent waiting for requests, salaries dipped to $18.83/hour nationally and $21.08/hour in top-25 markets).

As of press time, Lyft is still losing out to Uber when it comes to company valuations. The former is valued at $11.5 billion based on its latest funding round in Dec. 2017, while the latter's reported valuation ranges from $48 billion to a staggering $72 billion. But Lyft hopes to grow its value over time in part through better driver relations and more impactful content partnerships -- with media & entertainment as a key lens.

“Lyft's values have always been at the heart of the company, which is clear in how we treat our passengers, drivers, and people who come in contact with our brand -- artists and their teams recognize that,” says Schumacher. “We always want to make sure we’re providing real value to the artist. It’s not one-sided; it’s about finding the balance between our brand and the artist, and finding ways to create meaningful experiences for their fans.”