Lady with a white calculator preparing for tax season Featured blog post image for IRS 1099 Forms - What You Need To Know To Get Ahead

IRS 1099 Forms: How To Get Ahead

Lady with a white calculator preparing for tax season Featured blog post image for IRS 1099 Forms - What You Need To Know To Get Ahead

Who even thinks about IRS 1099 forms this early in the year? Like, don’t we have until the end of January to send our form 1099s?

In an ideal scenario, everybody associated with your company fills out & files their tax forms responsibly, and nobody experiences any crazy tax issues… but believe me, things can go horribly wrong real quick when you don’t prep ahead.

One common horror story is when a contractor goes MIA around the holidays (or even worse when January comes rolling in). Oh! The scrambling that goes into catching up on tax reports after the holiday season… not fun!

So, you really want to start preparing yourself and your organization much earlier (hint: throughout the year), so that you can catch any issues quickly… Because let’s be real for a second, nobody wants to go through a tax season dumpster fire!

[nervous laugh]


So, what is a 1099 form?

1099s are forms that business owners or nonprofits must file with the IRS every January for each contractor they paid more than $600 to during last year. The company fills out the necessary 1099 form, then sends copies to both the contractor and the IRS. The employer or a company must send the form by January 31st of the next year to avoid any penalties.
Note: Depending on the nature of the spending and income you’ve accumulated throughout the year, your company may need to fill out more than one 1099 form. The most common one for businesses is the 1099-MISC.

What other types of 1099 forms are out there?

There are actually a lot of other tax forms that fall in the 1099 category, but these are the common ones that most taxpayers use:

  • 1099-MISC

    This form cover income that falls outside the clause of the other 1099 forms. Money received from prizes and awards are examples of non-employment income. For those of you who fall under the self-employed category, it’s important to remember that you are responsible for paying the taxes you owe even if you don’t get the form from your employer. If the company submits a 1099 form to the IRS, but you don’t receive it for some reason, the IRS will send you a letter (actually, a bill!) saying you owe taxes on the income. Please note that the letter may not arrive in a timely manner.

  • 1099-B
    The 1099-B is a form that brokers must use when they sell your stock. It includes the sales date, the purchase price of each security sold, and the proceeds from each sale in order to calculate any capital gains or losses you incurred!
  • 1099-DIV
    If you own stock or other securities and receive over $10 in distributions, such as dividends, then this is a must. This includes any type of distribution that was paid on your stocks including capital gain distributions, nontaxable distributes from liquidation sales.
  • 1099-G
    One of the many important forms that you may need to fill out is a 1099-G. This form helps to report information about unemployment compensation, state and local income tax refunds, agricultural payments or taxable grants, etc.
  • 1099-INT
    Financial institutions (e.g. banks, brokerage firms, insurance companies, mortgage companies, credit unions, etc.) must provide this form if they pay the user more than $10 in interest during the year.
  • 1099-K
    The 1099-k form must be filed by companies that made over 200 transactions with an annual gross revenue of greater than $20,000 through third-party payment processors like Google Checkout, PayPal, or Stripe.
  • 1099-R.
    A 1099-R is the form filed when you get a distribution from your retirement plan. This includes IRS, Roth IRA, and 401(k) plans such as an employer-sponsored account which lets you save for retirement with pre-taxed money.

Why do independent contractors need a 1099 form?

An independent contractor counts as someone who is self-employed. That’s because when you enter a contract with an independent contractor to fill a specific role or complete a specific task, they can set their own hours, use their own tools, and even cater to multiple clients or businesses. Since contractors are considered self-employed, you (the business owner) or the (company) do not withhold taxes from their paychecks, because the contractor is solely responsible for paying their own taxes and providing their own benefits.

If a taxpayer hasn’t received the expected 1099 for income earned—even if the business didn’t file the 1099 form—the taxpayer might be able to report it under miscellaneous income. However, it’s best to contact a tax professional to determine the correct way to file for your particular tax situation.

What is the difference between a 1099-MISC form and a W-2 tax form?

2021 1099-MISC IRS Tax Form featured blog post image for IRS 1099 Forms - What You Need To Know To Get Ahead

1099s and W-2s are tax forms that help report different incomes.

1099-MISC, for instance, is typically used to report payments made to independent contractors (who cover their own employment taxes).

A W-2 form, on the other hand, is used for employees (whose employer withholds payroll taxes from their earnings). Businesses must issue 1099s to any payee (other than a corporation) who receives at least $600 during the year.

Who is exempt from 1099s?

Exemptions are a unique and often confusing part of the 1099 system. This can be frustrating for accountants who spend hours filling out tax documents but give relief to smaller businesses that cannot afford to hire an accountant or fill out paperwork themselves.

Exempt entities from Form 1099 issuance include any individual, organization, company or charity with income below $600 per year; however certain states may have different requirements which will override federal guidelines. It is best to consult a tax expert like a CPA to make sure that your organization is in compliance with tax laws.

Not sure “what’s the difference between a CPA, CFO, CFP?” Then THIS QUIZ is a MUST! In just three minutes, I’ll help you figure out exactly which finance pro you need, no acronyms included!

When is the 1099 tax form deadline for submission?

The deadline is typically January 31st of every year. You can check the official IRS website for more information on when and how to file your tax forms.

What happens if you don’t submit your 1099 IRS tax form?

What’s the worst that can happen if you work on your tax forms at the last minute? Weeeeell… you might inadvertently miss the cutoff and get a tax or an IRS audit notice.

Non-filing of 1099s to contractors is considered a violation of IRS regulations on information returns. Those who fail to comply can be penalized with fines or imprisonment. So, waiting too long to file your 1099s can be a costly mistake. Penalties can range from $50-280 per form, with the maximum penalty reaching up to 1 million dollars in industry fines!

3 Easy tips to get ahead of the tax season and be a rockstar CEO:

  1. Make a list of every contractor you’ve paid $600 or more this year to date. (Pro tip: QuickBooks Expenses By Vendor Summary report is super helpful!)
  2. Make sure you have their W9 on file – ask any contractors for the form if you’re missing theirs. (Pro tip: If you use Gusto to pay your contractors, this is all done for you!)
  3. Keep all W9s in one place (Google Drive, Dropbox, etc) – you will need them in January!
  4. Bonus: Repeat this process again in early January to capture any new contractors or ones who’ve hit the $600 threshold in the second part of the year.

P.S. Need help with strategizing for next year’s tax season? We are not a CPA firm and do not file personal or business taxes, but we do know of several trusted CPAs and we’d be happy to make an introduction. We do file the Form 990 for nonprofits and know that form like the back of our hands, so feel free to send your questions through our contact form and let’s connect!

SSS Think Pink 19

Do you have too many tools in your toolbox?

Raise your hand if you have a drawer in your kitchen, so jammed with gadgets and tools that you can barely open it, let alone find anything useful inside.

*Sheepishly raises hand*

You know exactly what I’m talking about. There’s that fancy potato masher from Williams Sonoma and the cherry pitter from 8 summers ago when you went through a brief obsession with cherries.

You have so many tools in the drawer that you don’t actually know which one to use when, so you end up using exactly none of them and defer to a good old fashioned fork for mashing those potatoes.

I was recently thinking about business in the same way.

If you spend more than three seconds online, you will be bombarded with tools, software, PDFs, templates, checklists, and workbooks all promising you clarity and confidence in some facet of your business. 

You may use that checklist once, or partially implement one of the software programs you purchased, but your laptop and inbox soon becomes the kitchen utensil repository of unused tools. The back end of your business remains in chaos because you haven’t committed to one quality system or process. 

Especially in the early stages of our businesses, when we’re trying to protect our margins and be as resourceful as possible, we grab the free stuff and hope for the best.

It’s time to clean out that toolbox, my friends!

In our business, we have a few key tools that fill up our toolbox and that’s it. The tools have evolved and upgraded over the years, as they should, but we keep our toolbox neat and tidy. If it doesn’t work or it’s half-used, it’s canceled. Everyone knows which systems are for what and everything has its place (and a coordinating Standard Operating Procedure). 

Image of a keyboard and pen to symbolize simple tools in your business toolbox.

Here are our tried-and-true tools that keep the business running smoothly, without cluttering up the toolbox!


  1. Quickbooks Online – The best accounting software out there, in my opinion. User-friendly, affordable, and talks to lots of other software.
  2. Profit Playbook – This free template will help you see into the future of your business with clarity to make smarter decisions, grow your income, and increase your impact.
  3. Gusto – This is my go-to payroll company. They handle all of your tax filings and make running payroll SO easy.

Project and Client Management

  1. Asana – We use Asana to organize all of our client work, membership stuff, and internal projects. It has been a game changer to keep us organized and ensure not a single ball gets dropped.
  2. Dubsado – Client onboarding was always a super manual process done entirely by me and Dubsado has helped us automate 90% of the process (and remove me from the other 10%).


  1. Slack – We love Slack for internal team communication (and are thinking of moving our membership communication here too!)
  2. Acuity Scheduling – I haven’t had a back-and-forth email exchange about meeting times in years now. Love just sending people a specific link to schedule time to meet.
  3. ConvertKit – We moved to ConvertKit a year ago and love being able to track our emails, create automated sequences, and take advantage of their analytics to better reach our audience.

What are your favorite tools? Which tools of yours are jamming up the drawer and need to go?


Free resource list!

As I wind down my month of celebration, I’m still in a little bit of shock that this business, dreamed up in a windowless office at a very boring job, has taken on the life that it has, thanks in no small part, to our tribe of purpose-driven leaders. A quick note of motivation for you today:

No dream is impossible, no ideas are too crazy, and there’s almost always a way to make something work.

But if you need a little help making that dream happen, I have a handful of free resources for you today. In a little trip down memory lane, I combed through everything we’ve created and compiled the most popular resources that our purpose-driven leaders have read, downloaded, and loved!

  • 4 Finance Pros – take our brand new quiz to learn which finance people you need on your team
  • Profit Playbook – a guide and Excel template to help you create a roadmap to greater impact and income, like a CFO
  • Storytelling with Financials – a free masterclass to help you analyze your nonprofit’s numbers (plus a free Financial Metrics Calculator)
  • Our Top Tools – the tried-and-true software that we swear by to keep the biz running
  • Quickbooks Review – my take on the best accounting system out there
  • FAQ – a classic if you’re new around here and want to know how we roll

PS – Reminder! We opened up a couple slots on our calendar before year-end for Strategy Sessions. If you need to pick the brain of a CFO for 30 minutes about anything and everything numbers, make sure to grab one here! >>>


Top 10 Money Resources to Save Time and Grow Your Bottom Line

I get asked all the time for the tried-and-true tools that help me run my business efficiently and can help you too, no matter what type of organization you’re running. I’ve compiled a list of the tools I use every single day both in my business and with clients to help them streamline processes and grow their bottom line AND their impact.


Here are my top tools and resources for busy, purpose-driven leaders:


  1. QuickBooks Online. As a CFO, you knew an accounting system had to be first, right? QBO is the perfect system for small businesses and nonprofits alike. It’s easy to use, intuitive (even if you dread your numbers), and affordable for pretty much everyone. Love it.
  2. Asana. We use Asana to organize all of our client workflows and I love how it is structured. I can get different views, like a task list or a calendar view, and this is one of the first tabs I open every morning to help plan my day.
  3. Acuity Scheduling. Every single leader I know is over-scheduled and it seems like half of our lives are spent coordinating meetings. I implemented Acuity years ago and I LOVE sending people my calendar link and letting them choose a meeting time that works. It literally cuts down on dozens of emails a week.
  4. Boomerang. I am a planner and that includes planning emails ahead of time. For example, I know I want to send an email reminder to a client on Monday but if it just sits in my draft folder, I will probably forget to send it, so then I write myself a note on a Post-It and before you know it, my desk is covered in neon squares. With Boomerang, you can schedule emails in the future and it will remind you if someone hasn’t responded!
  5. Gusto. Our favorite payroll provider, hands down. They pay your contractors and employees, handle all of the tax and compliance filings that no one wants to deal with, their platform is user friendly, and customer service is top notch. And they’ve also added benefits, time tracking, expense reimbursements, and vacation tracking – they’re truly becoming our HR hub!
  6. If you pay lots of vendors in different ways, then is my favorite place to keep it all organized. You can send paper checks or electronic payments and use their platform as a filing hub for vendor invoices too. 
  7. Expensify. Do your team members have company credit cards or lots of expense reimbursements? Expensify has a simple app where they can upload receipts, tell you what the expenses were for, and then import right into QuickBooks.
  8. Profit First. If you hate numbers but want to learn more about handling your financials with ease and clarity (like, how much should I be saving for taxes? What’s a good profit percentage?), this is an amazing book to read. It’s written so ANYONE can understand and is a practical addition to your bookshelf that you’ll reference for years to come.
  9. Profit Playbook. Our free template is the best and easiest way to make a plan to hit your revenue, profit, and cash goals. I walk you through how to build a forecast, step by step, so you have a clear vision of your financial future.
  10. Finance Pro Quiz. If you’ve ever Googled “what’s the difference between a CPA, CFO, CFP” then this quiz is a MUST. In just three minutes, I’ll help you figure out exactly which finance pro you need, no acronyms included!
  11. AmEx Credit Card. If you’re not using a credit card for your business expenses, to rack up points and rewards, you are missing out. This is my favorite credit card that I try and put everything on, then pay off each month.

Do you have a super fabulous tool or resource I should know about it? Share, so I can share with our community!

PS – We have tons of free webinars, podcast episodes, and other resources dropping practically weekly around here. Do you want to be part of the community to get the first dibs on the new stuff to help you grow your bottom line and your impact?!

#tools #resources #quickbooks #quickbooksonline #gusto #acuity #payroll


Which accounting system is best? Quickbooks Online, Xero, and Freshbooks

Can I be super honest with you right now?

It took me a solid six months of running my business to move from tracking revenue and expenses in Excel to Quickbooks Online. I am a CFO, for goodness’ sake! So I completely understand when newbie entrepreneurs tell me they don’t have an accounting system set up yet and ask me which software I recommend.

Ever since then, I’ve been rock solid with keeping up with my business accounting on a monthly basis and have tested a number of systems out there, both for myself and my clients.

Today I’m sharing the insider CFO’s view on three popular accounting systems, what works and what doesn’t, and how to choose what’s best for you. You will find a hundred articles out there from bookkeepers on what systems are best but as a CFO I’m interested in not only ease of entry, but analytics. (Remember the difference between a CFO and a bookkeeper?)

Why are analytics important, you ask? Don’t I just need to give my accountant some numbers at the end of the year so they can do my taxes?

Yes, BUT your numbers are more than just what you give to your CPA at tax time. Your financial statements hold a ton of insight into your business and help you make better decisions around growth (when and how you should grow), structure (can you afford to add team members), and more (SO MUCH MORE!), so those financials need to be sitting in the right house.

A CFO’s Accounting System Comparison:

Quickbooks Online

Why I love it: This is what I use for my own books and 90% of my clients. The interface and dashboard upon login is very helpful and visually appealing – it shows charts and graphs of your revenue, expenses, and net income at a glance.

It comes pre-populated with a chart of accounts and set-up is incredibly easy. You can invoice customers and receive ACH payments totally for free – yes, you get to KEEP all the money you earn! And most importantly for all non-accountants and accountants alike, it’s easy to use. Reporting is comprehensive – as a CFO, I NEED good reports. I need to play with different formats, time periods, and line items and Quickbooks lets me do it quickly and efficiently. Bonus points that Tech Soup Stock offers a DEEP discount for nonprofits!

What could be improved: Customer service is not great. Fortunately, I don’t need to call Intuit often, but when I have in the past, questions have taken ages to resolve. You may never need to call them if you have a CFO or accountant on board who has strong expertise in QBO so take that for what it’s worth.


Why I love it: It’s easy. Non-accountants will find the interface simple, uncluttered, and easy to use. There are a handful of tasks that business owners need and they’re all in Xero. Reports are simple enough for a small business owner to have a very clear understanding of their business. Customer service is excellent – I’ve submitted tickets for a few issues and they’ve gotten back to me via email quickly and persisted until the issue was fully resolved. Xero is also compatible with tons of other programs like Harvest, Stripe, and Expensify.

What could be improved: It’s TOO simple. Reporting is not as robust as a good leader NEEDS and some of the formatting is wonky. For example, if I want to see a comparative balance sheet for five years, it comes out from newest to oldest, so I have to look backwards to spot trends – super awkward. Xero doesn’t have the capacity to use classes in the same way that Quickbooks does so it’s probably not a good fit for organizations that need to segregate revenue and expenses into different buckets and run a separate P&L by department or program.


Why I love it: Even the most creative, right-brained souls can get comfortable with their numbers in Freshbooks. If you own a business and have yet to digitize your financial records but are so, so terrified of getting started, Freshbooks is a good place to dip your toe in the water. They allow you to invoice your clients, get paid through the system, and track your time, and it’s all very easy.

What could be improved: Even with Freshbooks’ most recent update, their software is still not up to par with Quickbooks or Xero in terms of robust financial reporting for the savvy CEO (yes, I mean YOU!). I wouldn’t recommend Freshbooks if you have a growing or even slightly complicated business, or if you plan to hire a bookkeeper or CFO.

All Three Software Programs

  1. Subscription model with a monthly fee
  2. Cloud-based technology; access your books anywhere
  3. Integrations with other platforms

My Recommendation

If you hadn’t gathered above, I LOVE Quickbooks Online. It’s robust enough for me, a savvy CEO and Chief Financial Officer, but simple enough for even the business owner who HATES math. The price point is reasonable and their banking integrations make monthly bookkeeping take a matter of minutes rather than hours.

Highly recommend!

Becoming more confident in your numbers is direct result of which accounting system you have and how comfortable you are using it. And we all know that knowing your numbers is a critical role of any leader. Knowing your numbers will allow you to make decisions with confidence based on black and white numbers – there’s no greater clarity than a P&L!

It may not seem like much, but choosing your accounting system is a critical business decision so check out each of these three systems, then dive in!



100 Degrees Must-Have Resources: Vol. 1

I’ve had lots of inquiries lately as to which apps, programs, and tools I recommend to nonprofits and social entrepreneurs so I thought I would put together my first 100 Degrees Must-Have Resources to share with you all. I certainly don’t claim to be the first to adopt the latest app (e.g. I have no plans to join SnapChat!), but I have personally used and can vouch for these tools.

Accounting software:

Freshbooks – Super inexpensive and easy to use accounting software for the beginning entrepreneur. Their mobile app makes it easy to invoice clients, enter expenses, and get a quick picture of your financials. Freshbooks is not the best choice for nonprofits with more complicated charts of accounts or income streams. Price: $

Intuit Quickbooks – The most well-known accounting software for small to mid-sized businesses of all types. Intuit offers Quickbooks Online or Desktop versions and can be as simple or complex as your business needs. The reporting capabilities are limited but you can generally get all of the info you need. It’s also compatible with dozens of other apps and programs. Price: $$

Abila MIP Fund Accounting – A much more complex, robust accounting system designed specifically for nonprofits. It’s a multi-cost center accounting system with deep chart of accounts capabilities and extensive reporting. If you have no idea what any of that means, contact me! The only downside is that you need an MIP-licensed consultant to help set it up. Price: $$$


Gusto – Simple to use payroll software to pay W2 employees and 1099 consultants. Gusto has a simple online platform to enter payroll and it’s great for organizations with a handful of employees.

Have more than a handful of employees? There are too many options out there to list but I can help you vet the choices if you’re looking to make a change!

Expense Reporting:

Expensify – Allows your employees to submit expense reports or credit card receipts remotely with an easy to use platform that allows for direct import into Quickbooks or other accounting software. They don’t have phone-accessible customer service (just email) so probably not a good choice if you expect to need a lot of hand-holding.

Mile IQ – The perfect app for tracking mileage. A couple taps and swipes and you’re set up to track all your business mileage for reimbursement or just simple tracking for taxes.

Other: – Probably the most popular CRM (Constituent Relationship Management) software on the market right now and for good reason. It’s highly customizable – in fact, I work with three different organizations who all use Salesforce and each instance looks completely different – and you can use it not only for donor/donation management, but also to track and report on any metrics you follow. Licenses aren’t cheap but Salesforce is robust enough to give you the data return on your investment.

TechSoup – Calling all 501(c)(3) nonprofits! If you aren’t registered with TechSoup and taking advantage of their software discounts (and refurbished hardware too!), YOU ARE MISSING OUT! They offer tons of discounts (Like, 90% off retail! Like, $10 MS Office licenses!) that can help set you up for success.

Auditor – I know of a handful of auditors that I’ve worked with over the years who specialize in nonprofits, do great work, and truly care about helping the organizations they work with to be best-in-class. Reach out and I’m happy to share!

I hope this helped you get started! If you know of another must-have tool that’s not included on this list, please let me know. I’d love to vet it and add it to my next resource list.