HomeStartup InsightsNavigating Tax Obligations for Startups: What You Need to Know

Navigating Tax Obligations for Startups: What You Need to Know

Navigating Tax Obligations for Startups: What You Need to Know

Navigating the complex landscape of startup taxation can be daunting, but with insights from CEOs and financial experts, startups can stay compliant and even save on taxes. From optimizing employee benefits for tax advantages to setting aside funds for year-end tax liabilities, we’ve compiled the top thirteen strategies shared by seasoned professionals. Discover how to tackle tax obligations effectively and learn from real challenges they’ve faced.

  • Optimize Employee Benefits for Tax Advantages
  • Understand Your Investment’s Tax Implications
  • Learn About Net Operating Losses
  • Navigate Contractor Classification and Tax Structuring
  • Comply with Tax Filing Deadlines and Fees
  • Manage Sales Tax Obligations Effectively
  • Outsource to a PEO for Tax Compliance
  • Strategize to Minimize Unemployment Tax Rates
  • Leverage Tax Credits and Robust Payroll Systems
  • Prioritize Tax Compliance and Planning
  • Claim R&D Tax Credits for Innovation
  • Make Quarterly Estimated Tax Payments
  • Set Aside Funds for Year-End Tax Liabilities

Optimize Employee Benefits for Tax Advantages

A relatively straightforward way you can improve your performance on taxes is by doing your research on the employee benefits programs that you offer, as not all of them are created equal in terms of the tax advantages for the business. Naturally, while you will still want to balance the cost of the programs versus the benefits they provide your employees, some of them are more or less a net positive for both in the grand scheme of things. 

I would recommend having a look around for health savings accounts (HSAs) and retirement plans that specifically call out the tax advantages for various reasons and see if they will be right for your business, as I’ve seen these in action before and was relatively impressed with how well they functioned.

Kate Kandefer, CEO, SEOwind

Understand Your Investment’s Tax Implications

You may withdraw your original investment without incurring any taxes. The fact that I have seen several accounts come in that are overpaying on taxes due to this one factor is definitely something that I would want to mention. 

The initial investment that you make in your company is referred to as your “basis,” although many individuals are unaware of this fact. The amount that you invest initially is referred to as your basis in any investment. There are a lot of business owners who are unaware of the fact that the government does not have the authority to tax the initial investment that they make into their firm, since that money has already been subject to taxation. 

Therefore, for the first year or years of operation, most company structures and entrepreneurs may claim that amount as income that is exempt from taxation.

Harrison Jordan, Founder and Managing Lawyer, Substance Law

Learn About Net Operating Losses

You should learn as much as you can about NOLs, or Net Operating Losses, with your tax obligations. Startups are volatile, and the odds are better than good that you’re not going to be turning a profit every quarter from the word go. In the case of a financial loss, you can actually use NOLs to offset taxable income from other years and give yourself a bit more breathing room by turning a negative into something of a future positive. 

The rules around NOLs are somewhat byzantine, but I highly encourage any startup leader to learn about how they work, as they can be the difference between profitability and shutting your doors if you operate on razor-thin margins.

Dragos Badea, CEO, Yarooms

Navigate Contractor Classification and Tax Structuring

Certainly, navigating startup tax obligations requires shrewd yet compliant maneuvering. For example, quickly accumulating misclassified 1099 contractors can trigger IRS alarms—such arrangements often warrant W-2 employment status, despite appearing cost-effective on paper. We learned this one the semi-hard way early on. 

Still, properly structured independent work holds legitimate appeal for fledglings balancing talent access and cash burn rates. The key is aligning worker relationships with reality, then optimizing within legal bounds through incentives like option pools tied to long-term value creation. Essentially, incentivize the roots without starving the fruits!

Tax structuring must also match business life cycles—S-Corps have different considerations than C-Corps, for instance. Sound foundational planning gives flexibility for future fundraising and growth phases. With the right trusted advisors, startups can fulfill obligations while minimizing unnecessary tax friction. But betting the farm on shady loopholes? Unwise. Transparent operations established early simplify everything later.

Lou Reverchuk, Co-Founder and CEO, EchoGlobal

Comply with Tax Filing Deadlines and Fees

For startups, it’s common to operate at a loss initially, which typically means there’s no immediate concern for income tax liabilities. However, understanding tax compliance is crucial. This involves knowing the specific deadlines for filing business tax returns, such as March 15 for S corporations and partnerships, and April 15 for C corporations, with extensions available if needed. Tax responsibilities extend beyond income tax to include payroll taxes, sales taxes, and various state and local taxes, highlighting the importance of comprehensive tax compliance at all levels. 

Startups must be aware of all filing requirements and deadlines at the federal, state, and local levels to prevent any unexpected issues. It’s not uncommon for new businesses to encounter problems due to overlooked filings, resulting in notifications from tax authorities and potential penalties. Ensuring registration with all applicable tax agencies and being aware of all tax obligations, including income, payroll, and sales taxes, is essential for maintaining compliance and avoiding surprises. 

In addition to these obligations, startups should be mindful of minimum fees imposed by some states, regardless of profit or loss. For example, California requires a minimum franchise tax of $800 after the first year, applicable even to businesses operating at a loss. The key challenge for startups in terms of taxes is not necessarily the amount owed but ensuring awareness and compliance with all filing requirements and tax types. Proper management of these obligations, with the assistance of knowledgeable CPA firms, can help startups navigate tax complexities, ensure compliance, and minimize tax liabilities effectively.

Michael Reeder, CPA, Managing Partner, Reeder CPA Group

Manage Sales Tax Obligations Effectively

Startups should be aware of sales tax. As soon as your business starts making money, you might need to deal with sales tax. Due to a rule known as economic nexus, you might have to pay sales taxes in any state where you sell your products. Companies add sales tax to the price of their products or services and then separate this collected tax to give to the government.

Sales tax laws and rates vary from state to state, which can be a real challenge to manage by yourself. Keeping up with these differing regulations and ensuring accurate tax collection and remittance can be a complex and time-consuming task. This complexity can be a good reason to consider outsourcing to experts, so you can concentrate on attracting customers and increasing sales.

Michael Brown, Managing Partner, Dribbin & Brown Criminal Lawyers

Outsource to a PEO for Tax Compliance

If you have employees (W-2 and 1099), you have to be careful about employment-related taxes and proper documentation related to hiring and paying people. I would seriously consider outsourcing employees to a PEO, even though it is more expensive in the short term. 

Compliance is important on the local, state, and federal levels, and keeping all the balls in the air is a huge distraction. As your company grows—say, reaches 50+ employees—it may make sense to bring this function in-house by hiring your own HR team. At that scale, it will be cost-efficient.

Aleksey Krylov, Managing Director, FTERA Advisors LLC

Strategize to Minimize Unemployment Tax Rates

Unemployment taxes, often referred to as unemployment insurance (UI) taxes, are designed to fund state unemployment insurance programs and are a critical piece of the payroll tax puzzle.

In my startup journey, facing unemployment taxes was akin to unexpectedly hitting a speed bump on a smooth road. We were so engrossed in scaling our operations and refining our product that the intricacies of unemployment taxes caught us somewhat off-guard.

To ensure compliance with unemployment tax obligations while also aiming to minimize the financial burden, we adopted a strategic approach. Unemployment tax rates are experience-rated, which means they can increase if former employees frequently claim unemployment benefits. By implementing solid HR practices, including clear communication about job expectations and performance, we aimed to reduce turnover and, consequently, unemployment claims.

Michael Dion, Chief Finance Nerd, F9 Finance

Leverage Tax Credits and Robust Payroll Systems

One critical tax obligation that startups should be aware of is payroll taxes, which include federal and state income taxes, Social Security, and Medicare taxes that need to be withheld from employees’ wages. Additionally, startups are responsible for paying the employer’s share of Social Security and Medicare taxes.

To ensure compliance while minimizing taxes, it’s crucial to have a robust payroll system and to understand the available tax credits that can reduce the tax burden. For instance, at Spectup, we leveraged the Work Opportunity Tax Credit (WOTC), which provides a tax incentive for hiring individuals from certain target groups who have consistently faced significant barriers to employment.

A tax-related challenge we faced involved navigating the complexities of state-level tax obligations as we expanded our operations across different states. Each state had its own set of rules and rates for income and employment taxes, requiring us to adapt our payroll system accordingly. 

To address this, we invested in a comprehensive payroll software solution that automatically updates tax rates and rules for each state, ensuring accuracy and compliance. Additionally, we consulted with tax professionals to ensure we were taking advantage of all applicable deductions and credits, thereby minimizing our overall tax liability while staying compliant with all federal and state regulations.

Niclas Schlopsna, Managing Consultant and CEO, spectup

Prioritize Tax Compliance and Planning

As a tax consulting professional, one thing that I have observed in my years of experience is the lack of knowledge about tax obligations among startups. Many startup founders are often more focused on developing their product or service and do not realize the importance of staying compliant with tax regulations. However, it is important for startups to be aware of their tax obligations and ensure compliance in order to avoid potential penalties and legal issues.

One of the main tax obligations that startups should be aware of is income tax. This refers to the tax paid on profits earned by a business, and it is calculated based on the company’s taxable income. Startups must ensure that they are accurately reporting their income and paying the necessary taxes to avoid any issues with the government.

While ensuring that startups have enough capital to cover their income taxes, it is also important to minimize the taxes paid in order to maximize profits. This can be done through tax planning and taking advantage of tax deductions and credits that are available for businesses.

Scott Orn, Chief Operating Officer, Kruze Consulting

Claim R&D Tax Credits for Innovation

One significant tax obligation we learned about the hard way in our startup journey is the R&D tax credit. Early on, we weren’t aware that our innovative tech development efforts could be claimed as R&D tax credits. The aftermath of this unnoticed opportunity was a bitter pill of lost savings. 

To rectify this, we consulted a tax advisor to guide us through the intricacies of R&D credit eligibility criteria and the claim process. Leveraging these credits has been instrumental in maximizing our resources while maintaining our tax-compliance obligation. This opened our eyes to the importance of tax literacy in startup finance management.

Abid Salahi, Co-Founder and CEO, FinlyWealth

Make Quarterly Estimated Tax Payments

One critical tax liability startups need to be aware of is the requirement for quarterly estimated tax payments. This is vital for managing cash flows effectively and avoiding penalties. Proper financial planning, diligent activities, and the use of all possible deductions and credits are key to ensuring minimal taxes payable and compliance. 

For instance, we faced a challenge in our first year due to inaccurate revenue estimates, which impacted our tax payments. By consulting with a tax expert and utilizing enhanced financial forecasting tools, we were able to more accurately adjust our estimates for subsequent quarters, helping us optimize our tax situation and avoid underpayment penalties. This experience highlighted the importance of proactive tax planning and the benefits of seeking expert advice.

Lee Odierno, Personal Injury Lawyer, The Odierno Law Firm, P.C.

Set Aside Funds for Year-End Tax Liabilities

Paying taxes on time is a fundamental tax obligation startups must not overlook. Tax liabilities accumulate throughout the year, but payments are often not due until the tax return is filed at the year’s end. This timing can lead to cash-flow challenges if not managed properly. We learned this the hard way in the early days of ProActuary Jobs. 

To avoid end-of-year surprises that could strain our cash flow, we now proactively set aside funds for tax liabilities throughout the year. This practice ensures we’re prepared for our tax payments when they’re due, maintaining healthy cash flow and staying compliant without unnecessary stress.

Dr. Mark Farrell (FIA), CEO, Associate Professor and Actuary, ProActuary Jobs

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