Quick Answer: Damon Day — the debt advisor I recommend more than anyone else, and the guy I started The Penny Stupid Project with back in 2022 — drove Lyft and Uber on New Year’s Eve and made $565. In 2023, the same night made him $1,000. He walks through why: more Waymos on the road, tips that basically disappeared, and a $20 bonus he missed by two minutes. The dollar figures are what happened to one driver, on one night, in one city — not a promise of what you’d make. The real value is the arithmetic he runs afterward, separating what he earned from what it actually cost him to earn it.
Debt is math wrapped in emotion — and gig work is no different. A big-sounding number on the app screen isn’t the same as money in your pocket until you subtract what it cost you to get it.
If you’ve read my write-ups of Damon’s other gig-work videos this year, you know the drill. If this is your first one: Damon and I started something called The Penny Stupid Project together in 2022 — a public, no-BS test of side hustles where neither of us sold anything. My half was retail arbitrage and Amazon FBA. Damon’s half was gig delivery. He’s run with it since, and his channel is still called The Penny Stupid Project on YouTube. I tell you I helped start it every time I feature his videos, because you deserve to know where I stand before you take my recommendation.
His newest video, posted August 30, 2026, is titled “2026 Lyft & Uber New Year’s Eve Driving — Only Made $565. Totally Sucked.” He drove the holiday shift he’s driven for years, and instead of just posting the total, he breaks down why a night that used to be his best of the year has turned into a mediocre one.
What Actually Happened on New Year’s Eve
Damon left home around 5:30 p.m. on December 31 and got back a little after 4:00 a.m. on New Year’s Day — roughly 10 hours out, with two breaks along the way for dinner and to charge the car, so closer to nine hours actually working. The first roughly $150 of his night wasn’t rides at all — it was a DoorDash run, an Instacart shop, and a Walmart shop-and-deliver order he picked up before he ever turned on the passenger apps. That left about $400 earned across the rest of the night doing Uber and Lyft rides.
He logged 19 rides total: 15 on Lyft Black and 4 on regular Uber. And about three-quarters of the money he made from rides came in the narrow window between midnight and 4:00 a.m. — not the hours before it.
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Gross Damon made on New Year’s Eve this year
What the same night earned him back in 2023
Total tips across all 19 rides — two tips, $7 and $4
Share of his ride income earned after midnight
Figures are what Damon logged on this one outing, in his one market — not typical pay, an average, or a projection.
Why the Same Night Pays Less Now: Waymo and Vanishing Tips
Two things changed the math, and neither one is something a driver can fix by working harder. First, Damon says he saw more Waymo robotaxis on the road that night than ever before — he describes them as constant, all over the area he was driving. He first started noticing them in a limited way a few years back, mostly downtown and often still with a safety driver behind the wheel. Now he says he never sees a driver in one, and every Waymo on the road is a ride a human driver didn’t get.
Second, tips collapsed. Of his 15 Lyft Black rides — a premium tier where riders are already paying a premium fare — he got exactly two tips: $7 on one ride, $4 on another. Eleven dollars total, across 15 rides. His four regular Uber rides brought in zero tips. He says a few years ago it was unusual not to get a tip on a Lyft Black ride; now it’s unusual to get one at all.
His bottom line on rideshare: Damon’s view, stated plainly in the video, is that full-time rideshare driving no longer makes sense as a strategy — the market has moved that much in a few years. That’s his read of his own local numbers, not a claim about every driver in every city. If you’re relying on Uber or Lyft passenger rides as full-time income, it’s worth running your own numbers the way he runs his.
The $20 Bonus He Missed by Two Minutes
Around 11:00 p.m., Uber offered Damon a bonus: one more ride and he’d earn an extra $20. A low-paying $5 ride popped up — a short pickup and drop he’d normally skip — and he took it anyway, purely to chase the bonus. It took him 25 minutes and paid $5. He never got the $20. The bonus had a cutoff time he hadn’t checked, and he’d accepted the ride two minutes past it.
He was frustrated less about the $20 itself and more about what it revealed: the only reason he took a ride he’d normally decline was a number he’d decided mattered, and that number turned out not to be real. I see the same pattern constantly in people managing debt — a target (“I’m only $200 from paying this card off,” “I’m so close to my savings goal”) that quietly talks someone into a decision their own usual rules would reject. The lesson isn’t that bonuses are bad. It’s that a target in your head can change what looks acceptable, and it’s worth noticing when that’s happening.
What a Dollar-a-Mile Ride Actually Costs You
Damon says plainly that on a non-surging night, a typical Uber or Lyft ride pays about a dollar a mile — so making $40 usually means driving about 40 miles, and that’s before you factor in driving back to where you started. Right now, the IRS’s own standard mileage rate is 76 cents a mile as of July 1, 2026 — a figure the IRS calculates from what gas, maintenance, tires, insurance, and depreciation actually cost per mile. At a dollar a mile of fare, that leaves roughly 24 cents a mile — about $9.60 on a 40-mile night — to pay you for your time and the risk of driving at all, before a dollar of self-employment tax comes out. That’s the math a “dollar a mile” fare is quietly asking you to accept.
Grocery Delivery Beat Rideshare That Night
Damon’s clearest advice in the video: he makes more money, in fewer miles, doing Instacart, Walmart Spark, and DoorDash than he does driving Uber X. His example: a $40 Instacart shop of about 30 items might take half an hour and a 5-mile delivery. That’s $40 earned for 5 miles driven. He says you can’t get that on Uber X — to make $40 on a regular Lyft or Uber ride, without a surge, you typically need to drive around 40 miles. Shopping in a store also skips the biggest hidden cost of rideshare entirely: you’re not putting miles on your tires, your engine, or your brakes while you’re pushing a cart.
The Airport Queue Nobody Should Sit In
Damon also checked the Lyft driver app’s airport queue out of curiosity — not because he’d ever actually wait in it. He found 160 drivers already lined up, with the app estimating about 60 rides an hour coming through. Do the math on that and you’re looking at a multi-hour wait for one ride. His question: why would Uber or Lyft ever raise driver pay when there are always drivers willing to sit in a parking lot for hours for one fare? His practical tip: use the rider-facing app (not the driver app) before committing to an area, to see how many other drivers are already clustered there. If the answer is “a lot,” move somewhere else.
Gross Revenue Is Not Profit
I want to be direct about this before you take any number in that video as a plan. The $565 he made that night, the $1,000 he made in 2023, the $400 from rides, the $150 from shops — none of it has vehicle costs or taxes subtracted yet. It’s what happened to one driver, on one night, in one city, with whatever offers that night’s app happened to show him. It is not a typical rideshare income. It is not an average. It is not what you should expect to make on any given night, holiday or otherwise.
Any post that shows you a gig-work video and lets you walk away thinking “so I could make $565 a night doing this” has done you a disservice. Before you count gross gig income as real money in your budget, run the same subtraction Damon is implicitly running when he says revenue isn’t profit:
- Mileage costs money whether or not you write it off. The IRS’s own standard mileage rate is 76 cents a mile as of July 1, 2026 (72.5 cents earlier in the year). That single number bundles gas, maintenance, tires, insurance, and depreciation — the expenses Damon says new drivers forget to count because they only think about the gas tank.
- You owe self-employment tax on top of income tax. Gig platforms pay you as an independent contractor and withhold nothing. The IRS treats net self-employment earnings as subject to a 15.3% self-employment tax on top of whatever income tax you owe. Set money aside as you earn it, or the bill next April will wreck the budget you were trying to fix.
- Watch for your own version of the $20 quest. If a bonus, goal, or round number is talking you into an offer you’d normally decline, separate the target from the offer actually in front of you. The target doesn’t make the offer better.
- Compare dollars-per-mile, not just dollars-per-ride. Damon’s own numbers show grocery and food delivery beating passenger rides on this exact measure — a $40 shop over 5 miles versus $40 over roughly 40 miles on a dollar-a-mile Uber fare.
Is Gig Work a Real Tool When You’re Behind on Bills?
I get some version of this question constantly: should I drive or shop for these apps to catch up on debt? My honest answer is the same one I give about every option on this site — it depends on your specific numbers, and most people never actually run them the way Damon runs his on camera.
Gig work can be a legitimate way to generate quick cash when you need money now and don’t have savings to draw on. You can often start today and get paid within days. That immediacy is real and valuable if you’re closing a short-term gap — a car payment, a medical bill, a shutoff notice. But before you count on it as ongoing income, especially income you’re depending on to catch up, run your own numbers with your own vehicle, your own city, and your own market — not Damon’s New Year’s Eve numbers, and not anyone else’s video.
“Run your own numbers before you count on it” isn’t a cop-out. It’s the same advice I’d give about any debt option on this site. Gig work is a tool, not a rescue plan, and it works best as one piece of a bigger decision — not the whole strategy. No gig work, in Damon’s own words, should be your full-time plan. Build toward stable, full-time income, and treat gig work as the part-time supplement around it.
More From the Side Hustle Archive
Damon and I have been writing about this experiment since it started in 2022. A few from the archive that pair well with this video:
- Quick Cash for Bills: Myth vs Reality — the honest version of “I need money fast”
- Side Hustles: When They Help and When They Hurt — the honest boundaries of what a side hustle can actually fix
- Side Hustle Success: What It Means and What to Do — the mindset piece behind the math
- Making More Money From Home With Online Arbitrage and Amazon — my own side of the original 2022 experiment
- Damon Day Switched His Walmart Spark Zone — the most recent write-up before this one
- Damon Day Was $76 From His Weekly Goal — another night a target number changed his own rules
Key Takeaway
Damon Day drove his usual New Year’s Eve shift and made $565 — nearly half what the same night earned him in 2023. More Waymo robotaxis on the road, tips that have all but disappeared, and a $20 bonus he missed by two minutes all played a part. His clearest lesson: grocery and food delivery paid him more per mile than rideshare that night, and gross revenue was never the number that mattered — what he actually kept after mileage costs and self-employment tax is. His figures are what happened to one driver, on one holiday, in one city — not a promise, and not a plan.
This is what I’ve seen after more than 30 years of helping people with money and debt. This is one video, one driver, one New Year’s Eve — take it as input for your thinking, not a directive. Only you know your full financial situation, what your car actually costs you to run, and whether your time is better spent on this or something else. Nobody gets to tell you what to do with your time or your money. Not me, not Damon, not anyone.
If you know someone counting on gig work to dig out of debt, send them this before they count the gross number as real money. Watching Damon separate what he earned from what it cost him is worth more than any lecture about budgeting.
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Common Questions
Who is Damon Day, and why does Steve feature his videos?
Damon Day is a debt advisor I’ve worked with and mentored for years, and the debt advisor I recommend to readers most often, because he builds solutions around a person’s actual situation rather than a one-size-fits-all script. Read the full explanation in Why Do You Recommend Damon Day as a Debt Advisor? His own debt-advice site is damonday.com, listed first in the description of his Penny Stupid Project YouTube channel.
What is the Penny Stupid Project?
The Penny Stupid Project is a side-hustle testing effort Damon and I started together in 2022 at pennystupid.com. Damon has run with it since — it’s his work now rather than a joint operation, and I disclose that I helped start it every time I feature his videos so you know where I stand. Neither of us sells anything through it; the point was, and still is, to test income opportunities in public and report the real results, including the nights that were worse than expected.
Did Damon actually make $565 on New Year’s Eve?
Yes, that’s the gross total he logged for the roughly nine hours he was actively working, across shop-and-deliver orders and 19 Uber and Lyft rides. It’s a gross figure — before mileage costs and self-employment tax, which he never claims are covered by that number.
Is $565, or $1,000 in 2023, typical rideshare pay for a holiday night?
No. Both are what one driver logged on one specific New Year’s Eve, in one market. Rideshare pay varies by city, time of night, how many other drivers and Waymo vehicles are active in the area, and plain luck in what offers appear on the screen. Don’t treat either figure as a guarantee or an average for your own market.
Why did Damon miss the $20 Uber bonus?
The bonus had a cutoff time he hadn’t checked. He accepted a low-paying ride specifically to chase the bonus, and the acceptance landed two minutes after the window closed. He still made the $5 fare — he just never collected the extra $20 he’d taken the ride for in the first place.
Is grocery or food delivery really better money than rideshare?
On this particular night, according to Damon’s own math, yes — he says a typical Instacart or Walmart shop pays more per mile driven than a typical Uber or Lyft ride does, because the miles you drive shopping in a store are far shorter than the miles you drive delivering a passenger across town. That’s his experience in his own market; run your own comparison before assuming it holds true where you live.
What He Works Through On Camera
YouTube’s auto-generated captions garble names and numbers badly enough that I won’t put them in quotation marks and call them his words. So what follows is my paraphrase of the beats in the video, not a transcript. Watch it above for what he actually says.
Opening the number. He starts by naming the $565 total, then immediately tells you it’s about half of what the same night earned him a few years back — setting up the whole video as an explanation of the gap, not a brag about the total.
The Waymo count. He describes seeing autonomous vehicles constantly through the night, in a way he says wasn’t true even a couple of years ago, and connects every one of them directly to a ride a human driver didn’t get.
Counting the tips. He walks through his 15 premium Lyft rides and 4 regular Uber rides one category at a time, landing on two tips totaling eleven dollars, and contrasts it with how routine tipping used to be on the same ride type a few years earlier.
The missed bonus. He narrates taking a ride he’d normally skip specifically to chase a small Uber bonus, discovering afterward that a time cutoff he hadn’t checked cost him the bonus by two minutes, and being more annoyed at the principle of it than at the twenty dollars itself.
The grocery-delivery pitch. He walks through why a shop pays better per mile than a ride, using a $40, five-mile shop as his example against a roughly forty-mile drive needed to earn the same $40 on a non-surging Uber or Lyft fare.
The airport queue. He pulls up the driver app’s live airport queue purely to show viewers the number — over a hundred and fifty drivers waiting — and uses it to explain why sitting and waiting is exactly what keeps per-ride pay low.
The closing math. He ends by reminding viewers that gas is not their only expense, that gig work should stay part-time rather than a full plan, and that the goal is profit, not revenue — because if you’re not netting anything after expenses, you’re not actually making money, you’re just keeping your car on the road.
