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    Several months ago, I came up with the idea of Show Me The Money Club (SMTMC). What is SMTMC? It is a weekly livestream on the Rideshare Guy Youtube channel that informs drivers of what is happening in the gig economy. 

    Judging by the numbers, it has done extremely well. Rideshare and delivery drivers gravitate to the channel because I am one of them. As a driver and commentator, I am doing work on the front lines and calling it the way I see it. 

    uber eats

    Sometimes I am labeled an “Uber mouthpiece”, which I ignore, but mostly people call me a driver’s advocate. The main idea behind SMTMC is to teach gig workers how to maximize earnings in a world where algorithms run wild. 

    We successfully put together two Town Hall meetings with 12 amazing drivers from large to small cities across the US. We had pro-Uber/Lyft drivers as well as anti-Uber/Lyft drivers freely voice their opinions. During those meetings, I gained more respect for drivers who accept every trip request and make good money to put food on their families’ tables. 

    I also gained respect for Uber/Lyft/Doordash for presenting these drivers with opportunities (flexibility) they would not be able to have with a regular W2 job. 

    During one of those Town Hall meetings, we were all blessed with the presence of Roxie the Uber Winterbird. I called her that because not only is she a rock star gig worker who moves around the country to make a living, but also because of her entrepreneurial spirit.

    Who is Roxie the Uber Winterbird?

    Without sharing her age, Roxie is one of the most energetic people I have ever met. She was born into a military family (Navy) and moved around a lot during her childhood. 

    Today she continues to move around the country, making money with Uber, Lyft, Doordash, Spark, Shipt, etc. She is the ultimate gig worker for whoever shows her the money. I wish I had a quarter of her energy and her tenacity!

    Roxie told me many stories during our interview, but how she started with Uber/Lyft is worth reading. The former autobody repair shop owner shares:

    “I was on a trip in Las Vegas with friends, and I kept seeing cars roll by with these huge pink fur mustaches. They were everywhere but I didn’t learn about them until months later. This was in 2015 when I got the Pink Seed planted. I was always the designated driver of our group because I don’t drink. Another long story but someone needs to be in control of the party. My friend says I’m going to call an Uber because you always drive. I’m like what the hell is an Uber?  I was like dang what a cool idea, wish I had thought of it, could have been making money long ago!”

    Eventually, Roxie lost the lease on her shop, so she decided to go full-time as a rideshare driver. Roxie continues:

    I started in my daughter’s BMW that she bought while being a gig worker. Then I duplicated what she did to buy my first car since I pretty much didn’t have a bucket to piss in after losing the rental car account and my business. I’m telling you Sergio, the Gig economy articles on RSG saved my ass. It was the combo of this channel and talking to other drivers in the waiting area at the airport that I learned how the apps worked since they really don’t tell you much when signing up.”

    How did Roxie become the Uber Winterbird?

    Roxie is living the dream that many drivers aspire to – working when and where she wants. As Roxie explains it, she lives a nomadic lifestyle and goes where she wants depending on the weather and time of year.

    “The Uber Winterbird is cute. It came from the Canadians who would come down to their winter homes in the South, they’re called Snowbirds. I found that with tourists and people traveling during the summer, it was hard to make good money doing rideshare in Phoenix with 120° temperatures. 

    Since Uber/Lyft is a cloud-based business and I can work from almost anywhere with a switch of region, background check and car inspection, I began moving with the weather and the people to make more money. 

    I focused on events and I worked opposite of the part-time drivers because most drivers don’t want to mess with the drunks. It’s crazy how every city is different. So you know I study everything about the cities I go to, and most of my rides would never know I’m just on vacation passing through and working my business every day. I normally go to cities where I have friends and family.”

    How was Roxie affected by the pandemic? What did she do to make a living? This is more inspiration for all the people half her age:

    “So anyway I had a good thing going until the pandemic came. I was working in Scottsdale, AZ and had just gotten to Austin to roll with the SXSW festival, which was canceled due to Covid, and I was closing on a house by the Riverwalk in San Antonio. A few weeks of the shutdown became a nightmare. I was also using my additional savings to pay for an XL vehicle that I thought was a cool addition to the business. It sat in the backyard since nobody was going anywhere! 

    I was quick to realize I needed to do something or I would lose my wheels, so I did every delivery I could do.

    Where Does Roxie Work Today?

    After shutdowns and moving, where is Roxie working today? You might be surprised she currently lives a slightly less nomadic lifestyle, thanks to the Uber-Hertz-Tesla rental partnership

    “Funny Hertz is still in my blood of making money. I rented a Tesla from Dec-April, got my car back out of the shop the second time, and loaded it up in time to move back up north for the summer. 

    I worked in Memphis in May and moved up to Nashville for CMA fest, Bonnaroo and NASCAR. I returned to the waiting list for a Tesla in Nashville, which I didn’t get until it was time for me to go to Charleston, SC, and then Maryland. 

    I rented a Model 3 long-range for three weeks and loved it. I worked in Nashville Thursday-Monday, then drove to my hometown north of Memphis. 

    You can’t put a price together on using a Tesla Rental for doing Uber unless you know what someone is going through financially. The info on RSG on EVs is spot on, even though I have to try everything out for myself. I can totally rent a Tesla cheaper than an apartment in Nashville and thought has crossed my mind to hit every state that I can switch to.” 

    Roxie’s Hertz Rental Tesla Adventure

    We did a deep dive into EV rentals Uber is pushing these days through Hertz. Take a look at Roxie’s results below – what she did the week before renting the Tesla is what blew my mind!

    Lyft was offering her major bonuses, and she worked her butt off for one week to pay for the Tesla rental for the next three. How is this for a businesswoman?

    Roxie did what every SMTMC member should do, stack all the bonuses and incentives offered to have a banger of a week. I don’t think I can come close to those numbers in Los Angeles. With money in the bank and her Tesla ready, Roxie went to work.

    The Tesla Model 3 cost Roxie $1718.59 for three weeks, including charging as you see on the receipt. What did she make? See below for earnings after 3 weeks: 

    Granted, the cost of the rental vehicle does not justify the work you have to do each week just to pay for it, but Roxie said she enjoyed it tremendously and would do it again. Now that her 2019 Jetta is out of the shop, she will be back to business as usual, driving happy passengers around and having a ball in the car.

    Takeaways for Drivers

    I am rarely lost for words, but Roxie’s story is truly an amazing one. It should be a total inspiration to everyone, not just gig workers. She hustles, does not complain, and has a clear plan of what she is currently doing and goals for the future. 

    Yes, Roxie is one in a million, but if she can do it, so can anyone with the will to do so.

    Uber/Lyft should consider themselves lucky to have a driver like her on their platform. It is also a testament to what these gig companies offer people like Roxie. 

    In what other business can you move around the country making a good living with such low barriers to entry? Are there many things wrong with Uber/Lyft? Absolutely, but here is one shining example of what the gig economy could be.

    “I travel with the season for my health while helping others learn how to work a Cloud Based business. I really enjoy what I do, at the same time helping others how to work with the various apps. I also send them to The Rideshare Guy. I have a Tesla reserved for when I get back to Nashville to work the Titans Games before heading back to San Antonio/Austin for the winter!”

    I want to thank Roxie for sharing her story with me, she has a friend for life. Rock on Roxie!

    Do you have a similar story to Roxie? Let us know in the comments below!


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    -Sergio @ RSG

    Sergio Avedian

    Sergio Avedian

    Sergio has been driving Uber and Lyft for about five years. He has over 6000 rides on both platforms, mostly on Uber. Sergio has a degree in finance, and worked on Wall St. for over eighteen years. In his free time, he still trades stocks and derivatives for himself and a few friends. He is also a PGA certified golf instructor, teaching golf is his passion. Sergio is married with two wonderful kids who take the rest of his afternoons/weekends between their soccer practices and golf tournaments.