This Isn’t The Flex You Think It Is

Picture it: It’s a warm spring day in our nation’s capital, and a 58 year old grandmother of 10 is knocking on the door to the Oval Office, McDelivery bag in hand, for a staged cross-promotional event for DoorDash and the Trump administration. The president comes out to receive the delivery and the Dasher proceeds to gush about how much she appreciates the work his administration is doing, particularly his “No Tax on Tips” policy as a part of the One Big Beautiful Bill Act and stating she “saved over $11,000”. At the end of the transaction, Trump gives her a seemingly very generous $100 tip. Sounds like a nice story, right? Sure, until you think even a little bit about it. Let’s be honest here, this stunt falls apart all on its own, but I'll break it down a little bit for you anyway.

First, let’s introduce the Dasher chosen to deliver the president’s lunch.

Sharon Simmons, whom the media has dubbed “DoorDash Grandma” to match the shirt she wore at the event, is a 58 year old grandmother of 10 from Arkansas, and caretaker for her husband, a cancer survivor. For the past four years, Sharon has been DoorDashing to help pay for her husband’s cancer treatment. In July 2025, she testified in congress in support of “No Tax on Tips”, which then caught the attention of DoorDash. In her testimony, Sharon describes her struggles as a working class caretaker for a sick family member. She goes on to mention the flexibility and independence that being a Dasher provides her, which is much needed given her circumstances. She says how she’s excited that dashers are included in the bill because that means “hundreds or thousands of dollars” that stay in her pocket every year. The delivery company saw an opportunity here and jumped on it.

Sharon’s story is one that resonates with many Americans across the country and across the political spectrum. I myself have been a Dasher for a number of years, and have a family member whose cancer diagnosis turned our lives upside down. While I do share and empathise with her struggles, that is precisely why this whole situation is deeply distressing to me. This woman is being taken advantage of by a fortune 500 company, and the President of The United States. Honestly, neither is surprising. If you ask me, this event feels dystopian, sinister, and begs the question: Why is DoorDash collaborating with the Federal Government on a bill that supposedly puts more money in somebody else's pockets?

Now at this point it feels cliche to say this, but this is just another instance of the wealthy keeping the working class in its place. DoorDash has a history of anti-worker behavior, to the detriment of the people who make their money for them. They have sued New York City to block their minimum wage laws for delivery workers, changed their interface to make it harder for customers to tip, settled in court for using tips to subsidize their base “DoorDash pay”, and has been accused by the National Labor Relations Board of illegally firing workers for attempting to organize unions. I can also tell you firsthand that Dasher base pay per delivery is usually around $3, or $15 for a grocery shopping order. With no true hourly rate, drivers’ paychecks are largely comprised of whatever a customer decides to tip. Keeping in mind the wear and tear on cars, gas, and no benefits, all before taxes are accounted for, this often results in poverty wages.

Mind you, all of this is on top of the fact that being a Dasher means that you aren't actually an employee of the company… Bear with me while I go on a short tangent, I promise it’s relevant.

If you’re a driver for DoorDash, you would be classified as an independent contractor, or in other words, you’re self-employed. This fact has blown my mind since I started working with DoorDash in 2019. The IRS defines an employee as “anyone who performs services … if you can control what will be done and how it will be done”. If you weren’t aware already, that’s exactly what DoorDash does. They control and maintain the app used to Dash, they supply and retain the customers, decide what customers to supply, when and where they are supplied, the company requires a background check, they decide the rate at which Dashers are paid, how pay is received, and often when it’s received, there is a specific way that you have to conduct a delivery, there is a timeframe in which you must complete a delivery, and you are penalized for declining a delivery, as well as for straying from the timeframe or specific methodology used to complete one. Not to mention if something goes wrong at any point, you’re just out of luck unless you’re lucky enough to get a helpful support agent. Maybe I'm dumb but that sounds like an employer-employee relationship to me. This is just another sneaky tactic that these gig work companies use to keep money in their own hands. I digress.

Companies like Doordash love Trump’s  “No Tax on Tips” policy because while they can afford to pay workers a minimum wage and provide benefits, they would much rather have their customer base provide that pay and keep profits to themselves. Meanwhile, consumer backlash for these practices is misdirected at the exploited tipped workers instead of the companies and governing bodies that control the policy and have the power to change it. But of course they won’t because that cuts into their bottom line.

Going back to our little story from the beginning, remember how in this on-camera conversation “DoorDash Grandma” told Trump she “saved over $11,000” on her 2025 taxes? Yeah, that’s a completely misleading misrepresentation of the facts, and in my opinion I think that she was coached to do so. Sharon Simmons earned an approximate total of $22,000 last year, with that $11,000 figure actually being the amount she earned in tips. This was revealed in a Fox News interview the next day where she also stated that “there’s been misunderstandings about … [her] taxes”, and that she actually doesn’t think her tax information is anyone’s business. Interesting thought, since she went on air discussing said business on national television.

This irony leads me to my point…

Why exactly does policy such as no taxes on tips sound so appealing in the eyes of the American working class in the first place? Well, just look inside the larger bill itself. The law includes over $1.2 trillion in federal spending cuts greatly affecting Medicaid and SNAP benefits, while also providing $150 billion in defense spending and more than $100 billion for Immigration & Customs Enforcement. Our social services that the working class depends on (with tipped workers relying on them at a higher rate) are being stripped away while money is being thrown at unnecessary and deeply unpopular programs.

The funny fact of the matter is if we paid our workforce (including tipped workers) a living wage in the first place, we wouldn’t even need such a policy. How about we raise the federal minimum wage, which has been stagnant at $7.25 since 2009, when gas was $1.79 a gallon. Maybe we give service workers the dignity of working for a livable hourly rate instead of busting their butts for tips. Perhaps we make gig workers full-fledged employees of the companies that they work for. Then, we wouldn’t even need a tax break for tips. We wouldn’t need to spend so much on social services such as Medicaid and SNAP. We wouldn’t have 35.9 million people living below the poverty line. And we wouldn’t need a 58 year old grandmother of 10 to work for a $100 tip from our billionaire president.

I know in the past, talking about money has been a taboo subject. But I would like us to move forward being more open. Under the National Labor Relations Act, we have the right to discuss our wages, and I think that we should. So, have the maybe tough or awkward conversations about how you're paid, how much, how often, and what you deserve. Be honest about what purchasing power you have with your salary. Understand other people’s situations and fight for better. That’s the first step in making the changes we need. Take that energy and take those conversations to congress. Let’s save ourselves the embarrassment and indignity of press events like this one in the future.

Let me know your thoughts on this and what sort of other analyses you’d like to see from me in the future!

Coming Soon to a Screen Near You

That’s right! another white guy with a platform, exactly what we all needed at this point in time. (I say that with an abundance of sarcasm if you couldn’t tell.)

For ages it feels like, I’ve been craving a proper outlet to release my thoughts, feelings, and ideas into the void… Well, why not here, and why not now?

Here I plan on discussing topics such as pop culture, politics/current affairs, history, or really anything that tickles my fancy that week. So check back here on Mondays for new deep dives from yours truly!