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 — posted a new video where he narrates roughly two hours of real gig-work decisions out loud: which offers he rejected, why, and the one Safeway shop he took. He ended the session at $64.70 gross, per his own video title. That’s what happened to him on that one outing — not a typical hourly rate, and not a promise of what you’d make. The real value is watching him do the rejection math in real time, before he ever accepts anything.
Debt is math wrapped in emotion — and so is knowing what to turn down. Damon’s video is a masterclass in saying no fast, out loud, before the math ever gets a chance to talk you into a bad offer.
If you read my last write-up about Damon’s DoorDash video, you already know the backstory. If this is the first one you’ve landed on, here it is in short: 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’m telling 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 4, 2026, is titled “I Made $64.70 in 2 Hours of Gig Work — What I Accepted (and Rejected).” It’s less a highlight reel and more a running commentary on decision-making: offer after offer scrolls across his phone, and he talks through the math on each one before his thumb ever touches accept or decline.
Each weekday I send one short email: one story that caught my attention, why it might matter to you, and one manageable thing you can do with it. A couple of minutes, and a dad joke.
In the latest issue (Oct 16): The check that looks like a scam may be real
Free. I sell nothing. Unsubscribe any time.
The Offers He Said No To
Before he accepted anything new, Damon turned down a run of offers that all failed his math for one reason or another. In order, roughly:
- $8 for 14 miles — rejected on sight. His running line for offers like this: “You can’t afford me.”
- Instacart, Tractor Supply — rejected without hesitation.
- Uber, $12 for 21 miles — rejected, same reasoning as the $8 offer.
- A merchandise delivery job with 13 stops, estimated at nearly two hours of driving — once he worked out the actual round trip, it meant driving about 50 miles for $50. “That’s a no thank you,” he said.
- A 12-stop order paying $42 across roughly 30 miles that would have ended with him stranded far from home — rejected.
- A Walmart three-item, three-customer batch shop for $25 — rejected outright. “Nobody would go to a shop for $7,” he said, working out that the batch was really three separate $7 shops bundled together.
- A DoorDash pickup at Home Depot with two drops for $11 across 10 miles — rejected as a clear negative.
Offers rejected before he accepted anything new
Shops accepted: a $22 Walmart run and a Safeway grocery shop
Gross total for the whole ~2-hour session, per his video title
Figures are what Damon logged on this one outing — not typical pay, an average, or a projection.
The Daily Money Brief — Free, at 10 AM
Money you may be owed, scams to dodge, and the fine print decoded — the consumer money news that affects your wallet, every weekday.
The $1-a-Item, $2-a-Mile Math He Uses to Decide
Earlier in the session, before any of the rejections, Damon took a small $22 Walmart shop — about 20 items, two miles from his house, on the way to get a haircut. He was direct about why: “you’re going to be driving right by the store” anyway, so a shop that pays for half a haircut on a route he was already taking is easy math, even if it’s not a “banger.”
How He Sizes Up a Shop Before Accepting
When the Safeway offer came in later — 24 items, about 9 miles — Damon ran it through what sounded like a personal rule of thumb, out loud, on camera: roughly $1 per item plus $2 per mile as his floor. 24 items worked out to $24; 9 miles worked out to about $18. Add those together and his own minimum for that shop was $42. Instacart was offering $40. Close enough that he took it — “it’s riding there,” as he put it. That’s not a universal formula for every driver in every market, but it’s a real example of turning a vague “does this feel worth it” into an actual number before you commit your car and your time.
The shop itself ran longer than he hoped — about 40 minutes instead of his optimistic 25 to 30 — which is its own honest lesson. Even a driver who’s done a store many times can misjudge the clock, and that time is real cost whether or not the app counts it against you.
Why Platforms Batch Cheap Orders With Good Ones
One aside worth pulling out on its own: when the Walmart three-item batch for $25 popped up, Damon worked through why platforms build offers like that. In his experience, apps will bundle one or two low-tip or no-tip orders together with a single order that has a real tip attached, hoping the combined total looks acceptable enough that a driver takes all three for the base pay of one. “They’re just finding ways to squeeze you,” was his read on it — his opinion from years of watching offers come across his own screen, not a claim I’m independently verifying about any platform’s official policy. Whether or not that’s the platform’s actual intent, the practical lesson holds regardless: a batch offer’s total dollar figure doesn’t tell you what any single stop inside it is actually worth. Break it apart before you accept it. I also wrote about the math behind turning down low Walmart Spark offers.
Could a Tesla Cybercab Be a Side Hustle? Not Yet.
This section is speculation, not a recommendation. Damon floated an idea on camera about a future where someone could own a Tesla Cybercab and put it on a robotaxi network to earn money without driving it themselves — the vehicle working while its owner is at a regular job. He said it himself in the video: there is no consumer Cybercab-ownership business operating today, and as of this video, that vehicle isn’t approved for the general public to buy and run as an income source anywhere. He described it as an idea for a future video series, not something to act on now. I’m not endorsing it as an investment or a side hustle — it’s an interesting “what if,” and nothing more, until there’s an actual product and actual numbers to run.
Why I’m Not Giving You a Dollar-Per-Hour Number
I want to be direct about this before you take anything in that video as a plan. The $64.70, the $22 Walmart shop, the $40 Safeway offer, every rejected dollar figure — all of it is what happened to one driver, on one afternoon, in one market, on whichever offers that day’s algorithm happened to show him. It is not a typical hourly rate. It is not an average. It is not what you should expect to make. Gig-delivery and gig-shopping pay varies enormously by city, time of day, day of the week, how many other drivers and shoppers are online, and plain luck in what shows up on your screen.
Any site that shows you a gig-work video and lets you walk away thinking “so I could make about $65 in two hours doing this” has done you a disservice. The value in Damon’s video isn’t the income figure. It’s the method: how fast he says no, the rough per-item and per-mile math he runs before saying yes, and how he reads a batch offer for what it actually pays per stop instead of trusting the total. That’s math literacy you can use no matter what your local market looks like when you try it.
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 does 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, run your own version of the math Damon runs in this video:
- Mileage costs money whether or not you write it off. The IRS’s own 2026 standard mileage rate is 76 cents a mile (as of July 1) — a figure the IRS calculated from what gas, maintenance, tires, insurance and depreciation actually cost per mile. A shop that pays $40 across 9 miles round trip has close to $7 of vehicle cost baked in before you’ve made a dime.
- You owe self-employment tax on top of income tax. Gig platforms pay you as an independent contractor. Nobody withholds anything for you. Set money aside, or the IRS bill next April will wreck the very budget you were trying to fix.
- A rejected offer isn’t wasted time if it’s fast. Damon turns down most of what crosses his screen in this video. That’s not failure — scrolling past a bad offer in three seconds costs almost nothing. Accepting one and regretting it costs the whole hour.
- Sometimes the math says don’t. If your car is older, your insurance doesn’t cover delivery or shopping work, or the miles you’d need to drive don’t pencil out against what your market actually pays, “not this, not right now” is a legitimate answer — not a failure.
“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.
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:
- Get Out of Debt by Increasing Income With Side Hustles: The Introduction to the Penny Stupid Project — how this whole experiment started
- 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
- Side Hustle Income Fear: Myth vs Reality — for anyone hesitant to even try
- Damon Day Runs the Penny Stupid Project Now — my write-up of his prior video, on the DoorDash shift where one $11 order wrecked a good hour
Key Takeaway
Damon Day’s newest Penny Stupid Project video is a real-time demonstration of saying no. He rejected at least six gig offers — low pay for too many miles, batch shops that quietly split a fair total into unfair pieces, routes that would strand him far from home — before accepting a Safeway shop that penciled out to roughly his own $1-per-item, $2-per-mile minimum. The $64.70 he logged over about two hours is what happened to him that day, not a promise. The real value is the decision-making: fast rejections, a real formula run out loud before accepting, and reading what a batch offer actually pays per stop instead of trusting the headline total.
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 afternoon — 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 considering gig work to close a gap, send them this before they sign up blind. Watching someone else run the real math — including all the offers he turns down — is worth more than any recruiting pitch.
Dealing With Debt? Understanding your options is the first step. See how all your debt relief options compare — including ones most sites won’t tell you about. The Find Your Path quiz gives a recommendation based on your actual numbers, and the Scam-O-Meter checks any company’s complaint history before you sign. Federal Reserve Bank of New York research shows bankruptcy filers recover faster than those who don’t file.
Free Tool — Contract Decoder: Have a contract from a debt relief company? The free Contract Decoder analyzes it for red flags, hidden fees, and problematic terms — before you sign anything. Decode My Contract →
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 offers not worth taking.
Is $64.70 in two hours typical gig-work pay?
No. It’s what one gig worker logged on one specific outing in one market, after rejecting a run of offers that didn’t meet his own math. Gig pay varies by city, time of day, platform demand, and plain luck in what offers appear on your screen — don’t treat any single video’s total as a guarantee or an average.
Why did Damon reject offers like $8 for 14 miles?
Because the payout per mile didn’t come close to covering his own cost of driving, let alone leaving anything for his time. Offers like that show up constantly on gig apps — the IRS’s own 76-cents-a-mile 2026 standard mileage rate is a reasonable stand-in for what a mile actually costs in gas, wear and depreciation, and an $8 offer for 14 miles doesn’t clear that bar before you’ve made a cent for your time.
What is a Tesla Cybercab, and is it a real side-hustle opportunity right now?
The Cybercab is a Tesla robotaxi vehicle Damon mentioned as a hypothetical future side hustle — the idea being an owner could put the car on a robotaxi network to earn money without driving it themselves. As of this video, there is no consumer ownership business for it operating anywhere; it isn’t something you can buy and put to work today. Treat it as speculation about the future, not a current opportunity.
What’s a simple way to judge whether a gig offer is worth taking?
Damon’s rough rule of thumb in this video was about $1 per item plus $2 per mile as his personal floor for a shopping order — if the offer comes close to or above that number, it’s worth considering; if it’s well below, it’s an easy pass. That’s not a universal formula for every market or platform, but the habit behind it — turning a vague feeling into an actual number before you accept — is worth copying no matter what you drive or shop for.
Cleaned-Up Transcript (Selected Portions)
YouTube’s auto-generated captions garble a fair amount, including proper nouns worth fixing here: what the captions render as “Instacard” is Instacart, “Fries” is the grocery chain Fry’s, “Whimo” is Waymo, and “cyber cap” is Cybercab. What follows is a lightly cleaned, readable version of select portions — not a verbatim court transcript — so watch the video above for the real thing. The final payout numbers spoken late in the video didn’t consistently transcribe well enough to quote reliably, so this excerpt stops before that point; the $64.70 total cited above comes directly from the video’s own title, not from the captions.
“$8, 14 miles. You can’t afford me. Uber, $12 going 21 miles. You can’t afford me. You know, it’s you versus them. They’re extracting value. They don’t give a damn if you drive 16 miles. They’re happy. They’re like, ‘This idiot is going to do it.’”
On the Walmart three-item batch offer paying $25: “Oh, get out of here, Walmart. No way. For $25? No way. That was ridiculous. Now Walmart’s starting to do three shops… They’re just finding ways to squeeze you guys. You got to stay on your toes. Nobody would go to a shop for $7, and that’s what they wanted you to do. The reason they do that is probably because one or two of those people have no tip, so then they batch it together with one guy that has like a $10 tip and hope that’s good enough, and it saves them on the base pay.”
Working out the Safeway shop offer on camera: “If you kind of use my minimums, 24 items is 24 bucks, and then 9 miles is 18. So that would be… should be 42, right? My minimum should be 42 on this, and it’s paying 40. So it’s… it’s riding there.”
On the Cybercab idea: “There is no Cybercab business right now. They’re not approved to do that anywhere… Right now you can’t get a Waymo, but if you can get a Cybercab, put it on Elon’s network and have that thing making money for you… I’m going to do a whole series on whether it can be a viable business, whether it’s sci-fi or it’s reality, and how soon it’s going to be reality.”
