The Vulnerabilities of the Gig Economy: When Apps Crash and Customers Clash

by Jason Tieri | Jul 19, 2025 | Blog

The Vulnerabilities of the Gig Economy: When Apps Crash and Customers Clash

Last week’s DoorDash outage highlighted a critical vulnerability that affects thousands of gig workers across the country. Beginning around 5am Eastern time, the platform experienced widespread technical difficulties that left both drivers and customers unable to access the service. By 8am, over 5,500 reports had been logged on Down Detector, with the service not fully restored until 10:30am. For many drivers who rely on DoorDash as their primary income source, those five hours represented a significant loss of potential earnings during the valuable morning rush.

This incident serves as a powerful reminder of one of the fundamental principles we consistently emphasize on the Gig Economy Podcast: diversification is essential for survival in the gig economy. Relying exclusively on a single platform creates a dangerous single point of failure. When that platform experiences technical difficulties, which is inevitable with any technology-based service, drivers who haven’t established alternative income streams find themselves completely unable to generate income. The most successful gig workers maintain active accounts on multiple platforms, allowing them to pivot quickly when one service experiences problems.

Customer service challenges continue to plague both drivers and customers across gig platforms. In a particularly frustrating example shared during our podcast, an Uber Eats customer attempted to increase their tip for a driver who had provided exceptional service, only to be repeatedly misunderstood by customer support representatives who appeared to be following scripts rather than addressing the actual request. Despite clearly explaining that they wanted to provide a larger tip to their delivery person, support representatives continued to misinterpret the situation as a complaint about late delivery, eventually offering credits to the customer instead of facilitating the additional tip for the driver.

Another significant challenge facing delivery drivers is navigating pickups at high-traffic event venues. Philadelphia sports fans have reported a troubling pattern where rideshare drivers accept ride requests from the sports complex designated pickup area, only to cancel as they approach. This creates a cycle where prices surge due to apparent demand, and customers end up paying more for their rides. Some drivers openly acknowledged waiting until prices surge before accepting rides, while others admit to canceling accepted rides when they notice prices increasing, hoping to receive the higher fare on their next request.

Safety concerns remain paramount for delivery drivers, particularly those handling food deliveries who may encounter territorial dogs. A sobering reminder of these dangers came from Florida, where a 65-year-old grandmother delivering for Uber Eats suffered severe injuries requiring a five-hour surgery after being attacked by two dogs while delivering to a neighbor’s house. Experienced drivers recommend always taking a moment to assess your surroundings before exiting your vehicle, carrying protective items like pepper spray, and maintaining awareness throughout each delivery.

The autonomous vehicle revolution continues its uneven progress, with Waymo vehicles demonstrating both promising advances and concerning limitations. A recent video showed a Waymo autonomous vehicle driving onto a freshly paved street in Atlanta, stopping midway, performing a three-point turn, and appearing confused about how to proceed. This incident joins previous reports of autonomous vehicles struggling with emergency vehicles, construction zones, and other unexpected road conditions that human drivers navigate instinctively.

For rideshare drivers looking to enhance the passenger experience while earning additional income, Octopus tablets offer an interesting opportunity. These free devices provide entertainment including trivia games and sports scores for passengers, with drivers earning monthly payments based on usage. The tablets require no financial investment from drivers and can generate approximately $50-75 monthly for full-time drivers.

As the gig economy continues to evolve, successful workers must remain adaptable, safety-conscious, and diversified across multiple platforms. The most resilient gig workers understand that technology will occasionally fail, customers will sometimes be unreasonable, and unexpected challenges will arise. By maintaining multiple income streams and prioritizing safety, gig workers can navigate these challenges while building sustainable independent careers.

Gig Economy Disrupted: Uber Tipping Controversy, DoorDash Fee Hikes, Milwaukee Strike & Waymo’s Teen Push

by Jason Tieri | Jul 14, 2025 | Blog

The gig economy landscape continues to evolve rapidly with significant developments affecting drivers, customers, and platforms alike. On this week’s episode of The Gig Economy Podcast, hosts Jason and Larry delved into several critical issues impacting gig workers nationwide.

One of the most contentious topics discussed was Uber CEO Dara Khosrowshahi’s recent statement on tipping, where he suggested that passengers “should only tip if you feel like you got your money’s worth. And then some.” This perspective raised eyebrows among drivers who depend on tips to make ends meet. According to data shared on the podcast, approximately 20% of Uber riders tip their drivers, which some drivers feel is dismally low considering the service they provide. The hosts contrasted this with food delivery, where tipping rates hover around 90% according to some estimates. This disparity highlights the different expectations across various gig economy sectors and how customer behavior significantly impacts driver income.

The conversation then shifted to regulatory changes in Seattle, where Doordash is facing what they call “extreme regulations.” Despite reporting $3 billion in revenue in the first quarter, Doordash is increasing delivery fees for Seattle customers, blaming new local regulations designed to provide more job security for gig workers. The new law requires companies to give workers 14-day notice before deactivation (except in cases of serious misconduct), base deactivations on reasonable policies, and provide workers with records of the decision-making process. While these protections benefit drivers, the hosts pointed out that platforms typically pass increased costs to consumers rather than absorbing them, potentially hurting the very communities these regulations aim to help.

A grassroots driver strike in Milwaukee also captured attention, though it didn’t go as planned. Drivers gathered at the airport staging lot to protest declining pay splits between drivers and rideshare companies. What began as a peaceful demonstration reportedly turned confrontational when some drivers blocked others who chose to continue working. This led to police intervention that effectively ended the protest. The hosts emphasized that while they support driver advocacy, forcing participation isn’t effective organizing strategy and that independent contractors face unique challenges when attempting collective action compared to traditional employees.

The podcast also covered Waymo’s expansion into offering autonomous rides for teens aged 14-17, which could potentially outpace adult ridership due to perceived safety benefits. Without human drivers, parents might feel more comfortable allowing their teens to use the service. The hosts speculated this could represent a significant shift in the rideshare market, particularly when considering safety concerns some passengers have about traditional rideshare experiences.

Other topics included Instacart’s new delivery options that offer customers more flexibility in delivery timing and pricing, a bizarre story about a sleepwalker who ordered just a honey mustard sauce through Doordash while asleep, and a troubling physical altercation between an Uber driver and an Atlanta sports reporter that escalated from a disagreement about air conditioning.

The episode highlighted the continuing tension between platform profitability, customer convenience, and driver welfare – a balancing act that defines the contemporary gig economy landscape. As regulations evolve and technology advances, both drivers and platforms must navigate an increasingly complex environment where the rules of engagement are constantly changing.

Uber Customer Support SAVED the Day! 😲 Doordash Driver Refused to Deliver Plan B! | Ep 258

by Jason Tieri | Jul 6, 2025 | Blog

Nashville adventures, dirty Uber cars, and customer service nightmares – the latest episode of the Gig Economy Podcast covered it all as the hosts returned from their meetup in Tennessee. What began as a casual gathering of podcast hosts and listeners quickly transformed into a weekend filled with gambling, games, and gig economy insights from the trenches.

The Nashville getaway featured a surprising amount of gambling on unexpected things – from a plastic horse racing game that had the group betting $5 per race to a crocodile tooth app game at a local bar. As one host admitted, “Jason was on fire Saturday night” when it came to the horse racing game, clearing about $100 over the weekend at $5 per match. The mini-vacation served as both entertainment and a reminder of how gig workers create community despite the independent nature of their work.

Upon returning to their respective cities, the podcast delved into several significant developments in the gig economy landscape. Most notably, the New York Taxi Commission has voted unanimously to restrict the controversial driver “lockouts” that Uber and Lyft had been implementing. Under new amendments, rideshare companies must now provide at least 72 hours’ notice to affected drivers before locking them out, and cannot lock out drivers for at least 16 hours once they start accepting trips. This represents a significant win for New York drivers who had been dealing with arbitrary lockouts that severely limited their ability to earn.

The episode also covered the expanding presence of automated services in the gig economy. Atlanta has become the fourth city to implement robot deliveries for Uber Eats, joining Los Angeles, Miami, and Dallas-Fort Worth. Orders from select restaurants, including Real Tacos, Ponco Chicken, and Shake Shack, can now be delivered by small autonomous robots that can travel up to four miles per hour with a 48-mile range. This advancement signals yet another step toward automation in an industry that currently provides income for millions of human workers.

Customer service issues took center stage as the hosts shared both personal experiences and viral stories. A particularly telling video contrasted Uber Eats’ customer service when the platform first launched (extremely accommodating with generous refunds and credits) versus the current state (unhelpful and dismissive). This decline in customer service quality parallels what many gig workers have experienced with declining pay over time – as platforms mature, both worker compensation and customer service seem to deteriorate.

Perhaps the most alarming story involved an imposter Uber driver in Fort Lauderdale who nearly got away with having his passenger drive through a security checkpoint. The driver, who was using someone else’s account, claimed he had forgotten his ID and convinced his passenger to switch seats before reaching a port security checkpoint where IDs were required. When police discovered the deception, the driver was arrested, and the passenger was left stranded, with Uber initially refusing to refund the ride until media inquiries pressured them to do so.

The episode concluded with a discussion of direct negotiation between passengers and drivers to circumvent app fees. While some customers are offering to pay drivers directly in cash – often at a price point that benefits both parties while cutting out the middleman, the hosts emphasized that such arrangements come with serious risks, particularly regarding insurance coverage in the event of an accident. Despite the temptation of immediate higher pay, they cautioned against making this a regular practice.