How Kindred Found The Ideal Tool While Driving For Uber


Uber Driver Advice From Kindred Sheppard.

Kindred Sheppard is no stranger to success. A naturally affable and likable man, it’s hard not to open up and share once you meet him. “I have the personal cell phone numbers of multiple Uber execs I’ve met, but it’s not in my nature to hit them up asking for favors,” said Kindred, a San Francisco-based Uber driver of nearly two years, “that’s why I wasn’t phased when [Hurdlr co-founder and CTO] Anu invited me to join the Hurdlr beta. I just wanted to get into the app and see what it’s all about.”

Kindred first heard about Hurdlr while getting his car inspected for Uber. “This guy Joey mentioned some new apps he’d heard about to help Uber drivers, so I checked it out,” Kindred said. “As soon as I downloaded it I knew you guys understood my needs. I’ve loved it since Day 1. Now I’m not saying it’s perfect; nothing is. Since the beta I’ve been with y’all through all the UI improvements and bug fixes. It really has been a useful tool. Even when I took a break from driving due to personal reasons, I came back to using [Hurdlr]. It’s a testament to the product that I came back to it at all.”

Like most of us, Kindred isn’t a tax scholar. In fact, he wasn’t aware of all the ins-and-outs of self-employment tax filing before Hurdlr. Kindred knew there was some benefit to tracking expenses as a driver, but was overwhelmed. “Honestly, I felt like a deer in the headlights. I would sit down with a pen and paper and not know where to start. When I started using Hurdlr, I felt like it knew what was important to track and what was not.”

Kindred looks at his business differently now, too. After working extremely hard with Uber the past two years, he’s planning on starting an executive transportation business and wants to leverage Hurdlr’s features to track enterprise-wide expenses. Kindred doesn’t know if he’d be able to visualize the components of a profitable business without the app. “It’s invaluable to see your financial picture unfolding transaction by transaction. It’s a total number there for you to see every day, which helps avoid sticker shock and helps you plan to take care of taxes,” said Kindred. “I think WE … and I say we … are the best out there. [Hurdlr] is very user-friendly, and has informative, functional information – I feel like it’s very hard to hit all three out of the park.”

While Kindred admitted Hurdlr helped him realize tax bills he wouldn’t have otherwise known about, it’s the expenses he’s never had to face that he’s thankful for. “The greatest benefit is the cost you never have to face in IRS penalties.” And even though Hurdlr made him aware of tax bills, it also helped shrink those bills by identifying and calculating the biggest deductions. Kindred said he could probably give a rough idea of the tax savings Hurdlr created – probably in the thousands, by his estimate – but it wasn’t the most important thing in his mind. “The greatest value is peace of mind. I get to spend more time with my daughter. I’m not crunching numbers with my notepad and sorting out receipts. The time that I gain … you can get money back, but you can’t get time back, you know? That’s what makes me most appreciative of the Hurdlr app.”

Make more money with Hurdlr by minimizing your taxes and increasing your pay. Hurdlr seamlessly tracks your true expenses, mileage, and deductions in real-time, on the go.

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  • Megan Handy

    Thank you Hurdlr, for starting this conversation and empowering drivers to capitalize on all their available deductions. This is the saddest thing I’ve ever read. America is so tragically financially undereducated. All these tens of thousands of people started driving for Uber oblivious to the taxation situation they were simultaneously agreeing to. Most drivers don’t realize that Uber selfishly works them as 1099 contractors in order to SAVE THEMSELVES THE EXPENSE OF PAYING EMPLOYMENT TAXES AND ADMIN COSTS ASSOCIATED WITH IT. Consequently, driver’s are forced into the HIGHEST TAXED INCOME BRACKET in America, paying twice the taxes on their income as they would as an employee. It’s a genius business model from the standpoint of a business owner but a financial step backwards for the drivers. Taxes are our largest expense in life, and for Uber drivers, that expense just increased two fold.