Siri, Alexa and That Google Gal Will Only Get You So Far

For personal assistance on an even tighter budget, there are companies like Fiverr, which hires freelancers around the world, resulting in lower prices, though perhaps a slightly more alienated feeling.

I tried a few of these services. Here’s what I found.


On Day 1 of signing up with Fin, my hopes are high. After reading through the website’s live feed of customer requests, I’m convinced that the app can take whatever I throw at it, no matter how obscure the request.

The first task is my insurance coverage, which is set to expire in a few weeks. It’s a prime example of my most dreaded task, the kind I’d normally put off.

First on the website chat box, then with voice-to-text on my phone, I ask Fin to look into it and find me the cheapest plan it can. Later in the day, I also ask it for help with shipping my car out of state. I have found one service, but ask if Fin can find something better. Then I sit back, remembering my own days as a personal assistant, thinking how the tide has turned.

By the end of the day, Fin has given me estimated health insurance quotes and a link to an online insurance website. But when I try to open the link, I have to re-enter all of my information again myself to see anything. Didn’t I pay Fin to do this? Later that night and the next morning, Fin sends me car shipping services, but they aren’t faster or cheaper than what I’d found myself in a few minutes of quick research.

I get frustrated and decided to do the job myself on my commute. About 45 minutes later, I have found a faster shipping service and booked it. All of Fin’s calls and emails on my behalf start to feel like halfhearted busywork.

Later that second morning, I consider giving Fin one last task but decide to check my balance first. The problem is, I can’t find it anywhere. One long search later, I do find it and my jaw drops. Fin says it spent 215 minutes on the requests, and with an initial free 60 minutes deducted, is going to charge me $181.


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I call customer service, which eventually reviews my case and says Fin should have kept me more informed about the time it was spending. They give me a 100-minute credit.

Cost: $81

Billable time spent: 3.6 hours


I begin trying Magic around the same time as Fin. I’m feeling sick, so I ask Magic to schedule me a last-minute doctor’s appointment for the same day. It’s both a challenging request and something I really don’t want to do myself. Magic promises encryption for personal data, so I feel comfortable giving it my health insurance and personal information. It tells me it’ll check back with me in 35 minutes.

My doctor isn’t available for at least two weeks, so Magic ends up finding me an appointment at an urgent care center. In the end, Magic hands the task back to me — the doctor’s office won’t let it schedule the appointment for me because of privacy concerns. But Magic does tell me who to call, and that I can see a doctor that day. Since I’m already stressed and feeling sick, I find that Magic’s help does actually feel helpful. At least it got the process started.

Cost: $31.86

Billable time spent: 54 minutes


After my experiences with Fin and Magic, I’m ready to try something low risk. I search around on Fiverr and find a virtual personal assistant named Rex, based in Nigeria, who charges $10 an hour and has five-star reviews.

With Rex, I decide to start with a non-research task: listing some items I want to sell on eBay. But right away, we run into problems. It’s raining hard in Lagos, where Rex is based, and his internet keeps going out. Once the rain eases up, I give him my eBay login information, but before long, eBay has noticed the unusual activity on my account and shuts it down.

After we solve that issue, Rex needs my PayPal information, and I remember a conversation with Mr. Chen about protecting personal information. Magic and Fin guarantee security with data encryption, but Rex is working on his home computer. He keeps reassuring me it’s fine, but I decide to switch up the task. Instead, I ask him to research the amount of time I have to find new health insurance. He sends me snapshots of the Covered California website that I don’t find very helpful, but we part on good terms.

Cost: $22

Billable time spent: two hours


After searching the online freelancer marketplace, I selected a Florida-based “personal virtual assistant” named Corin because of her 100 percent job success rating, and her low hourly rate ($20). In only a few hours, she accepts my invitation to do the job. With my budget running low, I decide to offer Corin as much as I think she could possibly do in one short hour: check on a medical insurance rule for me, call my bank about my car loan, list the items I still want to sell on eBay.

Before half the hour had passed, Corin has already sent me a Google doc answering my first two questions, and following up about my eBay products. By the end of the hour, she hasn’t listed everything but tells me she’ll finish the task for no extra charge. For the first time in the experiment, I actually do trust my virtual personal assistant to get things done without draining my wallet.

Cost: $20

Billable time spent: one hour

As the experiment drew to a close, I realized that my initial mistakes had come from the fact that I wanted a personal assistant to do my work, but I didn’t necessarily anticipate the work of managing a personal assistant. Would I use some of them again? Probably. But as Mr. Lessin said: “We always talk about what we’re competing with, and what we’re competing with is people doing tasks themselves.”

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