I can recall looking for a part time job in local newspapers when I was in high school. Sometimes a friend and I would ride around with our $2.29 per gallon gas looking for places that were hiring. Facebook was gaining popularity but not for job posting. So, searching for jobs on my phone via an app was unimaginable.
Advances in technology have changed the way that we do things in the world. Everything an individual needs to find a job is right at their fingertips. There are more opportunities to find gigs and be your own boss if that’s what one desires.
There’s no question that the way people find ways to earn income has changed. What has not changed is the fact that the IRS wants their share of the income earned. But how do we apply the tax code to these new ways that taxpayers are earning money?
We are going to break that down in this three-part series. Whether your client is doing odd jobs on an app like TaskRabbit, driving for Lyft, renting out their home or car, you will know how to guide them. This is what we are going to cover today with a focus on rideshare, delivery, and other service gigs.
Tax Loss Harvesting with Cryptocurrency
In the Fall of 2025, Bitcoin reached an all-time high of over $120,000. Since then, it fell over 40% to under $70,000 in the first quarter of 2026, before slightly recovering, currently resting around $75,000 as of this writing. With the steep drop in the price of Bitcoin and other cryptocurrencies, a common question from taxpayers is whether they can use the current losses to offset their other income. Large investors and professionals such as Grant Cardone and Shehan Chandrasekera (Head of Tax Strategy at Cointracker) have suggested that cryptocurrency can be sold and bought back immediately to claim the tax benefits. As with most things, the answer to this is not as simple as they portray, and many commentators, influencers, and sometimes professionals, miss the intricacies of cryptocurrency taxation.
