A guide to tax season for founders

Helen Chong

For U.S.-based startups, tax season is a nearly universal pain point. 

That’s why Puzzle has put together the comprehensive guide to tax season for founders, complete with experts explaining almost everything you need to file easily and accurately. 

Below, Luke Frye, CPA, our own Head of Customer Success at Puzzle, provides his insights into: 

  1. Year-round habits to get your business ready for tax season
  2. Why experts say growth-stage startups shouldn’t DIY taxes
  3. 3 secrets your tax accountant wants to tell you
“It may be a cliché, but taxes are inevitable. The longer you wait to deal with them, the worse it’s going to get for your startup. If you’re not staying on top of things, enlist the help of tools like Puzzle or hire supportive professionals.” 

Year-round habits to get you ready for tax season

When it comes to startup taxes, you can build from the beginning with the end in mind. 

Without accurate financial records, how can you expect a seamless and compliant tax return? 

So, here are three financial habits you can instill to ensure your startup conquers tax season — instead of the other way around. 

1. Set up your official payroll ASAP

Startups at their earliest stages are frequently made up of a group of friends. It makes sense that no one thinks to establish a legitimate payroll. (And, funnily enough, many founders forget to put themselves on payroll even after it’s set up.) 

However, this is one critical step to ensuring you are legitimized as a company. 

2. Company expenses on personal accounts must be on the books

Founders often charge business expenses to their personal cards. These purchases also need to be put on the books. After all, accounting for everything will keep your records clean. 

Ideally, you should reimburse yourself once a month under an accountable plan. This approach is “penny for penny,” says Luke, as opposed to a stipend, which would be taxable. 

To avoid this headache entirely, you can also: 

  1. Structure your purchasing from day one
  2. Separate your financials as soon as you have bank accounts under your EIN

3. Have a tax accountant lined up by EOY

In the grand scheme of things, Luke recommends hiring a tax accountant as soon as you’ve finalized your incorporation. 

In terms of preparing for tax season, he encourages every founder to locate an accountant, get in contact, sign a contract, and perhaps even pay them before the year’s end. By extension, if you wait until March, all of the best accountants will be swamped by then. 

Overall, do not wait until you need a tax accountant. By then, it’ll likely be an emergency. 

To find a vetted tax accountant who caters to startups, check out this directory by Puzzle. 

“It’s frankly a garbage-in, garbage-out situation. If you have a haphazard accounting system, the quality of your tax return just will not be higher than the subpar quality of your bookkeeping.” 

Why you should never DIY your startup’s taxes

As a startup, your goal should be deploying as efficiently as possible — both in terms of dollars and human effort. This is especially the case for those who’ve raised capital. 

For tax season, it is simply far more efficient and effective to bring on a professional. 

Here are three reasons why. 

1. Tax accountants possess the know-how for maximizing savings

Yes, it is technically cheaper for pre-seed and seed-stage ventures to DIY their finances. 

After all, everyone is trying to minimize burn in current market environments, and services like, say, Stripe Atlas are cheaper than hiring a lawyer. 

However, those immediate gains will not measure up to the big-picture returns driven by accountants with years of experience in maximizing savings. A founder’s basic financial education just does not compare. 

2. Taxes are one of the worst uses of a founder’s time

In the rare case that you’re a founder who doubles as a highly efficient bookkeeper, you may be able to manually handle your company’s taxes. Or, even using software like Puzzle can get the job done — up to a certain point. 

Once your startup seriously begins to scale, you, the founder, need to be out of the weeds. You want to be logging in to check relevant financials, not matching transactions. 

3. Online resources are not the letter of the law

If you’re a diligent and self-educated founder or CFO, you may go searching for resources online and find some pretty legit instructions, such as an IRS article. 

While it may provide insights, the reality is: Online content is not the law. Tax codes and regulations are an entirely separate beast — best understood by accountants. 

In the meantime, what are some reliable resources? Luke recommends three: 

  1. The Journal — A tech news, analysis, and advice blog for founders by Fondo
  2. The Smarter Startup — A tax blog for venture-backed startups by Burkland
  3. Alex Roytenberg, CPA — His go-to Twitter source for valuable crypto tax insights
“I would not DIY all of your finances. For instance, if you DIY your bookkeeping, I highly encourage you to use a tax accountant — no matter what. Get at least one professional on your side to catch things you just don’t know about.” 

3 secrets your tax accountant wants to tell you

The best accountants have spent years on the job, building up niche know-how and shortcuts. 

Here are three high-value tax secrets that they love to pass on to startup founders. 

1. Always extend your tax return

It’s best practice to extend your tax return deadline every single year — for two reasons. 

  1. You get more time to file overall. The standard six-month extension ends October 15. 
  2. You get to benefit in the event of a superseded tax return

Let’s say you requested an extension in February and still filed your return by March. However, by May, you discovered new info that required you to correct your filings and properly account for your carry-forward loss

Instead of filing an amended tax return, which is far more tedious and expensive, you can file a superseded tax return by your extended due date. 

2. Startups have significant (and often complex) savings opportunities

One such opportunity is the R&D tax credit — “basically free money,” explains Luke. 

If you fund U.S.-based research and development, which technically includes paying salaries for engineers, designers, and any similar positions that develop products, the IRS can provide a credit against your payroll tax. 

But here’s why this tax credit is especially impactful: 

  • Many tax credits and refunds are based solely on your income tax due. 
  • Many startups — due to the nature of venture-backed companies — are not profitable. 
  • As C corporations with zero net income, those startups wind up paying no income tax. 
  • This makes the R&D tax credit so uniquely helpful: You can offset existing payroll taxes. 

Even if you’ve overlooked this credit in the past, you may be able to get it refunded retroactively

3. Accountants operate on a FIFO basis & require quick responses

Accountants often execute work on a FIFO (“first in, first out”) basis. That means if you get your books to your accountant first, you’ll likely be filed first

However, Luke also notes that accountants are “notoriously bad” with emails. 

If you have their attention, respond as quickly as possible to keep it. Otherwise, waiting a day or two to reply may mean ending up back at the bottom of the stack. 

“When it comes to communicating with your tax accountant, keep yourself top of mind and provide them with clear deadlines.” 

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Helen Chong
Growth @ Puzzle

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