On October 23 there was a conference at the Tax Policy Center on Taxing the Gig Economy. There were two panels, one on the size and scope of the gig economy and the other on tax administration issues.
Here is a link for those who would like to listen to the event. I recommend the entire conference, which runs about 2 hours and 40 minutes. The first part of the panel lays out the data around the size of the gig economy, including a slide deck presented by Michael Udell that lists out trends in self-employment income over the past thirty years. The part that I found most interesting was the discussion of tax administration issues that begins at about 1 hour and nine minutes into the session.
The tax administration panel consisted of Dave Williams, Chief Tax Officer at Intuit, Nina Olson, National Taxpayer Advocate, Caroline Bruckner, a professor at American University who has written extensively on tax issues in the gig economy, and Pooja Kondabolu, who is the Senior Tax Policy Manager at Airbnb. It was moderated by Howard Gleckman, a senior fellow at Brookings.
A few of the highlights of the discussion included Intuit’s Dave Williams perceptively commenting on the lack of knowledge around tax issues among many of the service providers (e.g., Lyft drivers, Airbnb hosts), and how in the current environment many of the service providers simply do not know what they do not know. Professor Bruckner’s prior work Shortchanged lays out in great detail some of the difficulties facing sellers and service providers. Professor Bruckner recently testified in the Senate on some the issues she discussed on the panel (written testimony here). At the panel, she spoke about the possibility of changes to information reporting and dates for estimated payments to help people comply.
The National Taxpayer Advocate spoke about how the IRS could make the system better by facilitating compliance through a better and targeted use of technology for those who enter the tax system after getting an EIN, with things like wizards, email reminders about estimated taxes and the possibility of salient online account portals that could actually be used to help people comply.
What stood out to me in the discussion is how challenging some of the compliance issues are for self-employed taxpayers generally, and how there are many differing ways to improve the outcome. None of the measures alone however can work.