Ride Share Hustle: Leveraging Uber, Lyft, and Sidecar
January 24, 2016
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A quick spray of Fabreeze and I’m back on the road.
The last passenger had a bit of a scent, and I clear up any doubts that it will linger with a single spritz. As I pull up the block, I take a quick look at my phone to see my next rider’s name. Mary should be coming out of her row home apartment in just a moment – and there she is – I’d put her somewhere in her thirties, with a friendly and approachable look about her. I greet her as she gets into the back seat, and wait for our destination to load. It looks like my next Uber drive is taking me to the Newark Airport. “All strapped in?”, I ask, and once I receive the nod we are off.
It’s been about two months since I started driving for the ride share service, and I am far from tired of it. Mary and I get to talking after she rattles off a few text messages. She’s a marketing manager in New York City, who moved to New Jersey after her west village apartment’s roof caved in. Some landlord. She just got done working on a full campaign for Jaguar, and this immediately brings on the questions about how 2015 Madison Ave stacks up against the Mad Men portrayal on television. By the time I get to terminal B, we’ve hardly begun reminiscing about our favorite episodes of the show.
Small talk, yes, but not in the “nice weather” sort of way. I hardly got to ask her about life in the ad world – the deadlines, the type of work – does it get old? What are the people like? What’s the craziest business event that she partook in? I suppose that’s a good thing, as there is no joy in the other extreme – hitting a conversational road block long before you can part ways. I count myself fortunate to have received another good client. Sober, check. Polite, check. Well versed in one of my favorite TV shows, check mate.
Before I can think anymore of it, I am dispatched for my next ride, and I have the good fortune of being within 100 yards of them already. I pull up the length of a football field to get my next passenger. Sometimes, I wait up to 30 minutes between rides, so the short interval between this one and the last catches me off guard. Katjia, my next passenger, lugs a giant suitcase behind her. Based on weight and dimensions I gather that the contents include a full line of winter clothing or a medium size mammal, perhaps both. We get the case in the back of my station wagon and get off before a cop sees us. It’s technically illegal to pick up as an Uber driver at the airport.
As we ride towards the Manhattan skyline, I take a quick look at my earnings for the day. Katjia is on the phone so I do a quick tally. It looks like I’m up to about $50 for two hours on the road – certainly not enough to hire Jeeves the butler, but a respectable sum for a mere commoner such as myself. I’ve been driving about 15 extra hours a week for an average of $300. Considering that my girlfriend doesn’t get home until 8ish, I am free to pick a few passengers up on my commute home… but only if I feel like it.
That’s the beauty of Lyft, Uber, Sidecar, and other ride sharing services, you only work when you want. Drivers don’t only choose their hours, but actually determine the minute that they want to call it a day. It’s as simple as pushing a button to go on or offline. For someone like myself, the flexibility is an appealing feature. I work a job where the day might end at 5:05, or 10:00 that night. On those long days, there is no pressure to log in and take rides – as a supplemental source of income, I’m not bound to a certain deadline or dollar figure.
This is not to say that every Uber ride that I’ve given has been a great one. Riders can pose all sorts of nuisances, from the olfactory to the audible. The worst has been intoxicated passengers. These are your wildcards. They might do anything from meddling with your things, to becoming outright combative. My experience has been colored by a number of factors, including the facts that I am a man, and generally am bigger than my passengers. I write that as a disclaimer for anyone who may be less comfortable in an environment with these types.
Revisiting the ride sharing phenomenon in a larger sense, I think the service offers a great utility to customers, and will likely replace the yellow cab business in most cities, as it is cheaper and more efficient. Of course casualties will include the incumbent taxi and limo services, and eventually today’s drivers. With the advent of driverless cars, it’s only a matter of time before the multitude of Uber and Lyft drivers are replaced by automated vehicles. This is supported by Uber’s poaching of Carnegie Mellon robotics faculty. I doubt that they are working in the accounting department over there (See http://www.wired.com/2015/09/uber-gives-carnegie-mellon-millions-poaching-profs/).
So long as drivers aren’t banking on making this a full time career for the next twenty years, I think it’s reasonable to say that ride sharing is a great way to make a supplementary income in cities across America. It allows people to unlock the value of what is often the second most expensive item they own, a car. For many, 25 rides a week may be enough to offset a car payment. For those who are more savvy, there are further ways to monetize your time and car.
For instance, these services have led to the rise of “uberpreneurs”, ladies and gentlemen who use their time with riders as a chance to promote a second line of business. See this Forbes article to read about one man who made over $250,000 in a year selling jewelry from his other business to passengers in California: http://www.forbes.com/forbes/welcome/. Your own pursuits could range from multilevel marketing, to advertisements within your car, to a simple snack bar and menu that you offer your riders. I’ve been experimenting with this for fun, and I find that it’s an easy way to make an extra $5-$10 per hour in the car offering small sealed snacks like cookies, and drinks like Gatorade.
Another way to actualize benefits from these services is to have your app running on your commute home. Normal commute miles to a day job are not tax deductible for many, but turning on the app for your commute can turn these miles into a business expense. So long as you are picking up rides along your way as you are dispatched (yes, there is a chance that rides will take you out of your way), then these miles can be deducted from your ride share income taxes at up to $.57 per mile. For someone like myself, who has a 45 mile commute, this is a great way to offset taxes and put money back in your pocket. I’ll reiterate, this is not a call to “beat the U.S. tax code”, it’s simply a way to re-purpose your time and mileage from a commute into something that yields a dollar benefit. Make sure you are picking up rides, and don’t try to deduct ride share mileage from your day job income – it’s not worth an audit to skirt around this (nor is it right).
As you can see there is potential to earn in this sharing economy, but people do need to consider how highly they regard their time and what their priorities are before committing to a ride share gig. Uber will not get you rich on its own, however, I believe that it is a perfectly viable strategy for those who are looking to come up with quick cash – and I specifically recommend as a first step towards financial freedom by hustling to earn dollars and cents that go into passive investments, like a first rental property or securities. This is a sustainable habit that will turn you into an owner from a private contractor (which is how you are classified in your ride share service agreement). If you want to stay on life’s treadmill and spend what you earn, then go ahead and drive Lyft all day – spend that check on a trip to Disney. However, the real potential here is to get a sizable number of people from jobs that are on the bubble (making $30k-$50k per year) into a more solid middle class wage bracket, where they can afford to save and avoid the pitfalls of our financial system that lead people to perpetual dependence on the man (payday loans, deferred education, an “unquittable job”). For those still interested, I’ll give a brief description on some of the important considerations of a potential driver.
Ease of sign up (8/10)
I found the prospect of signing up to be a driver was met with convenience. I speak for Uber and Lyft in this case. For each, you visit the following sites and create a login:
Uber
Lyft
A few things that are good to know ahead of time. This assumes that you are driving for the basic service, and not the black car or SUV product:
1. You must be 21 years of age or older to drive
2. You must have a valid driver’s license
3. Your car must be 2005 or newer (2003 for Lyft)
4. It must have four doors
After filling out the requisite information and agreeing to the terms of service, you will be sent a confirmation email, and receive a query about your consent to a background check, where your driving history and criminal record will be evaluated. This took two business days, and is contracted out to an independent firm at no cost to you. In the meantime, you are ushered on to the next step.
With Lyft, there is an extra stage to the sign up process. You must set up a time to meet with a “mentor”, someone who is a current driver. They will size you up for manners, professionalism, and the state of your automobile (make sure it is nice and clean). Note, this is not merely a formality – the Lyft team can be rather strict, and will deny drivers based on their rating by the mentor. Those who are rejected are given vague answers and will likely not receive any concrete feedback about why they did not pass the screen. You will complete a practice ride with your mentor where you are judged on your driving and the way you carry yourself. The process takes up to an hour, and can usually be scheduled within a few days.
Supposing you make it through the mentor session, you must upload proper documentation for both ride share services. This includes your latest driver’s license, proof of insurance, and a vehicle registration. These are checked against your address and name found in the background check, so the bottleneck becomes the results from that screen. All said and done, you should hear back in a week at most.
In the meantime, you watch a quick training video about the car service and download the app. At this point, you sit tight, and wait for an approval email. If all runs clear, then you can be on the road in as few as three days.
I give this process an 8/10 considering the alternative, and the remote filing of everything. You don’t have to travel anywhere (other than for the mentor session), and the application is pretty concise. This compares to the esoteric process of either interviewing and clearing for work at a cab company, or to create your own cab operation and apply for the necessary documentation with the municipality. The service companies streamline all of this. Still, it’s not so immediate as to warrant a perfect score – as holdups in the background check and some back and forth with the company may occur.
Flexibility (9/10)
A major selling point in favor of a ride share gig is the freedom it affords drivers. There are no minimum hours required, nor are there times of day you are pressured to be on. The guiding mechanism at play is the pricing model that serves to balance supply and demand in a given area. Riders are alerted through the app when more riders are around than drivers. This takes the form of premium (surge) pricing, which can increase normal fares by multiples of five or more when demand is peaking. Even in the largest surges, there is no obligation to get driving, which means peace of mind and greater autonomy for drivers. It’s a valuable consideration that has fueled over a million contractors to sign up with Uber alone. Simply switch the app on by selecting “go online”, and remove yourself by selecting “go offline”. This couldn’t be simpler.
The only thing limiting flexibility is that you cannot finish your day mid fare. That means that no matter how far your rider’s trip takes you out of the way, you are on the hook for that ride before you can call it quits. Unfortunately, you can’t see your destination until you pick up the rider, which throws a small monkey wrench in your ability to get around these inconvenient trips.
Compensation (4/10)
Pay is a perceived differently depending on whom you ask. The numbers from my experience are about $20 per hour in New Jersey, and slightly higher in New York City. Be advised that the current $35/hour advertisement is a fairly optimistic number, and you aren’t likely to consistently reach that. However, I’ve given rides that are an hour or longer of all highway miles – for these, I’ve made over $60 per hour, but keep in mind that your average pay sags lower because you will not always be dispatched for a ride and the downtime eats into your per hour figure.
To my point above about how pay is perceived, that’s going to depend on what you can make otherwise, and how badly you want the money. To some, $20/hour is a mere pittance, while to most, it ranges from a reasonable to life changing income. As middlemen, Uber and Lyft take a cut of each fare that you receive. This fraction will vary depending on what city you are located in, and how heavily they are recruiting drivers there. Today, it’s generally between 20% and 25%. My $20 per hour is after this cut, but does not include gas, maintenance on my car, and anything miscellaneous like washing. You are covered under an additional insurance policy with the services that will protect you up to a million dollars in damage and injuries, and that’s at no charge beyond the cut taken from your fare. All in all, you probably pay out $5 per hour in expenses, so subtract that out of your calculated wage.
For many, there are other opportunities that can provide better earnings than ~$15 per hour, but far fewer that offer that pay with such a high degree of flexibility. The paychecks are not mind blowing, but if the money is only a single factor out of many behind this choice, then it is much easier to rationalize. Also keep in mind the other potential benefits to earn more that I mentioned above. There are ways to combine the driving with other interests and side hustles to yield larger paychecks.
Safety (8/10)
Thus far, I have been happy about the comfort and safety provided by the ride share apps. Passengers are vetted with a background check as well, to ensure that drivers are protected. Additionally, a two way rating system keeps people’s conduct in line, as both drivers and riders can lose access to the service if they fall below a certain rating. You are free to rate however you’d like, and are at liberty to define your own standards of a good passenger. This helps to keep problematic customers out of the service, though a number of them inevitably sneak through.
Here are a few things that I have run into thus far that may be cause for concern:
1. Passengers will use the account of a friend, spouse, parent, etc. to grab rides. This means that the passenger could have any sort of background and not be vetted properly by the sign up channels in place. Luckily, I’ve had no issues with conduct from these riders to this point.
2. Some riders will be drunk when you pick them up. This is an inevitability, and the trip can range from entertaining to tense. I did once have to kick a rider out of my car with all but a shouting match, as he began pick things up out of the back of my station wagon and throwing them around. I would not stand for this, so I stopped the car, and hunkered down until he got out on his own. I told him that he could request a ride from someone else if they were willing to drive him, and gave a 1 star rating so people would see the red flag of a lower rating.
3. You may be asked to drop someone off in a rough part of town where you don’t want to be idling in a car. I find these fears to be largely overblown, but still, common sense dictates that there are some parts of town where you don’t hang out. As long as you keep moving, and your pickups/drop offs are quick, there isn’t much to worry about.
On the whole, the platform is safe and transparent. Running as a cashless operation also helps to ensure that you don’t have a target on your back as easy money for a devious passenger.
Fun (9/10)
Personally, the best feature of ride sharing is the enjoyment of meeting new and interesting people. If you are social (I am a clear introvert, but do enjoy company in moderation), then this is a great job for storytelling, commiserating, and outright bullshitting. Particularly in large metro areas, the crowd is younger, hip, professional, and tech savvy. Those whom I have driven thus far have been a great group on the whole. The driver does have a great deal of control over the flow of the ride, and I find that as long as I remain friendly, most riders match my spirits.
The occasional rider will be angry, upset, or zoned out, and these are the people you ignore. All you have to do is get them to their destination safely and in reasonable time. Most of my riders, however, have been fun to talk with, and some have turned into friends. I started with Uber when I moved to a new city in hopes that the driving would help me become familiar with the area. I am pleased to say that I not only know the places now, but multiple people in town, and have gotten paid for all of it. Last time I was at the mall, I ran into one of my riders and we ended up hanging out for a bit. I’m meeting another this week who was looking for some advice on how to break into financial services. While I used to have stretches of time with no good stories, I tend to come home with at least one or two a night after driving. They range from touching to outright hilarious. I drove a 911 dispatcher last week who told me at least a dozen of her craziest phone calls on the job. I’ve picked up everyone from a hedge fund manager to a well known chef in Washington DC, to an aspiring NBA athlete. Everyone has a story and I always enjoy to opportunity to listen when someone feels like sharing.
Help and support (8/10)
So far as the apps are concerned, they are generally slick, minimalist, and easy to use. A map view allows you to see your location and view any surge pricing that comes up. The application syncs up to GPS for easy navigation on the go. Your pay statements are also managed in another tab of the app, as is your driver rating. You can refer others to the services for a fee as well (up to $500 for Lyft in Boston at the time of writing), and this can be managed through the program.
You are sent a weekly summary of your driving, including hours, pay, and mileage. These go to your email for easy tracking.
In the even of an issue, such as an accident, tickets, software bugs, I’ve found and heard that the support teams to be very helpful and friendly. This makes inquiries simple, and their thorough answers have prevented me from returning with follow ups in multiple cases. I believe that it is a sign of good training, but I have heard of others who have had less positive experiences. I don’t count those out, and the main concerns voiced were vague answers and slow turnaround time. This could in theory be the result of poorly phrased questions, but I will ignore that and request that you to bear some of these complaints in mind.
Closing Out
As I get out of the Lincoln tunnel and drop Katjia off, wishing her well with her new startup job in London, I get ready to shut the app down for the day. It’s cool to think that I can get paid to meet new people in an area where I don’t know tons of friends. It reminds me that the ride share gig serves many purposes for me, and that others can invent their own aims to reconcile with side hustles.
For one, the extra pay is a nice cushion for bills, passive investments, and funneling into side businesses. Since my day job covers my expenses, whatever I earn is gravy. That could mean that I throw some money into Google AdWords to learn a bit about basic online marketing – it could mean a nice dinner out at some point in the month with my girl. Or it could go towards my financial freedom, investing in stocks and hopefully my first property in the not-so-distant future.
Regardless of the financial choices, I am also benefiting from the rides in a psychic and social sense. Working with the same people can become boring, especially when you are inundated with the relentless office politics. Picking up ten people with ten diverse backgrounds, from silver spoon, to former homelessness is both humbling and eye opening – the ultimate refresher. It is a truly rewarding experience and I’ve learned a ton so far strictly from my conversations. Any of the financial considerations like taxes and selling snacks have taken a backseat, and I have no regrets about that. The job has made me into a better seller, more astute listener, and more interesting guy, even though I’m only two months in. It’s less of a surprise to me that Brian Johnson, lead singer of AC/DC remained a cab driver, even after finding international fame as a rock n roller. There is something inherently interesting about the captive audience of a driver.
Given the flexibility, ease of sign up, and ability to get creative with your work, there is no longer an excuse for the person who fits the above criteria to complain that they can’t afford their lifestyle, or have nothing fun to do – get in that car and start hustling!

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