First 1099
“I lost a significant amount of money on my new freelance business this year, can I use those losses to offset my standard W-2 salary taxes?”
A loss from a new freelance business can often matter on a return, but the outcome usually depends on how the activity is classified, whether there is a real profit motive, and how the loss interacts with other income such as W-2 wages. The treatment can also vary based on whether the business is a sole proprietorship, how expenses were documented, and whether any limits apply to offsetting ordinary income. In many cases, the bookkeeping behind the first year, including income, startup costs, and business use records, shapes how the loss is viewed. A focused session can map this against your actual situation in plain English.
In your 90-minute session, the KGOB advisor handling it will:
- Read your exact situation and tell you, in plain English, what’s actually going on.
- Lay out your options and the trade-offs — no jargon, no judgment.
- Give you a clear next step you can act on, whether that’s with us or on your own.
“I got my first 1099 and I'm completely lost, can you walk me through it?”
“I just left my W-2 job to go independent, how do my taxes change?”
“I just got a 1099-K from Venmo for selling my old personal clothes at a loss, do I actually have to pay taxes on this money?”
“I worked as an independent contractor for three months and never saved for taxes, what are my immediate payment plan options with the IRS?”
This page is a prompt to start a conversation, not tax or legal advice, and states no tax-law specifics as fact. A consult session does not by itself create an ongoing engagement. We do not promise specific outcomes or savings. Kohari Gonzalez Oneyear & Brown PLLC — Charlotte, NC.
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