Taxes, Insurance and Financial Freedom: There’s an App For That

Freedom and flexibility usually top the list of reasons why people become independent workers. No asking for time off, no breakroom pizza and no “Can we hop on a call real quick?” emails. 

One of the few downsides is that when you’re an independent worker, you have to manage all the complexities of insurance, taxes and more without the support of an employer. It can be confusing, time-consuming and sometimes expensive to make the best choices for yourself and your family. 

That’s why Roadie has partnered with Stride to give drivers the tools they need to reach the full potential of independent work. Stride is a one-stop platform (including a free app) that simplifies the complexities of independence, like finding the right health insurance plan, managing taxes and saving on everyday expenses. 

Let’s look at all the ways Stride can benefit you as an independent driver. 


Simplify Insurance Protection 

Stride breaks the complicated process of choosing insurance protection into simple steps. As an official partner of, Stride offers all the same plans you’d find in your state’s Marketplace at the same low prices. With personalized recommendations and unbiased advisors, Stride makes it simpler to get the insurance plan that best fits your needs and budget. Through Roadie’s partnership, 36% of drivers who applied for health insurance via Stride are paying less than $1/month! 

Stride is free to use — the only cost is the cost of the carrier’s plan; there are no hidden fees. When you apply throughStride, you also get access to streamlined tools that simplify plan selection based on doctors, prescriptions, health needs and budget. 

In addition to necessary coverage like health, dental and vision, Stride can also help you secure extra coverage like affordable life, accident and disability insurance. 

Drivers using Roadie have saved $709/month on average by getting insurance through Stride. That’s $12,762 in an 18-month health premium period. Because Stride exclusively serves independent workers, they don’t tell you what to do — they provide you with tools and support to do things your way. “Drivers using Roadie have saved on average $731/month on average by getting insurance through Stride. That’s $13,152 in an 18-month health premium period.”


Take Control at Tax Time

You work hard, so at tax time, you want to be sure to keep as much of your money as possible. But as an independent worker, keeping up with all the information you need can be a real hassle. Recording mileage, estimating tax deductions, uploading receipts and categorizing expenses — it’s a lot. 

With the free Stride app, you get mileage and expense tracking so you can stay on top of your cash flow, business expenses and more all in one place. When it’s time to file your taxes, you’ll get a full report of all your earnings and deductions to simplify your tax return and maximize savings. Roadie Drivers who track their miles and expenses on the app save an average of  $710 per year on taxes. Through Roadie’s partnership with Stride, drivers can even save 25% off their federal tax return using TurboTax’s Self-Employed product. 

The app isn’t just helpful at tax time — it also includes step-by-step guides and other useful information to help you manage finances,insurance and more as an independent worker all year long. 


Everyday Savings

Stride helps simplify taxes, finances and insurance from your phone, with (almost) everything you need just a few taps away. But Stride also helps put more of your money back in your pocket with discounts and savings on things like business services, shopping, gas and dining. With promotions from Stride’s marketplace of vendors, you’ll find savings on everyday expenses and more chances to stretch your money. It’s a win-win-win!


Set Yourself Up For Success

Roadie’s partnership with Stride makes it simpler than ever to make the most of independent work, with free tools to manage your insurance, taxes and finances. Sign up with Stride today!


*The above information is not meant to be tax advice. You are advised to consult a tax professional when filing your taxes and reporting your earnings and deductions from the Roadie app.