How to File Your 1099 and 1096 Forms Using Quickbooks Online: A Step by Step Guide

January 25th, 2013

Let me set the scene: It's January.  Your 1099s have to be mailed out in five days (1099s must be mailed out to vendors by January 31st).  And, you have NO CLUE how the hell to make, print, or file them with the IRS and send them out to your vendors. WHAT DOES A NORMAL PERSON WHO IS NOT AN ACCOUNTANT, TAX GUY, OR QUICKBOOKS WIZ TO DO?!?!?!

Look no more. Here you go. Here is a step by step guide of how to file your 1099s (and 1096 summary form) using Quickbooks Online. I'm sorry if your Quickbooks version does not allow you this functionality (because I'm sure some don't). All I can say is... maybe it's time to upgradeee SON!

Here's how to file your 1099 forms (and 1096 summary form) using Quickbooks Online. Follow these steps:

1. First, go to Staples (or your local office supplies store) and buy a packet of 1099 forms (which should come with 2 1096 forms within it). I typically buy the packet of 50 1099 forms. It will have sheets of Copy A (which are sent to the IRS), Copy B and Copy 2 (which are sent to your vendors), and Copy C (which you will keep on file as the business owner). All of this will come in one packet, with shrink wrap around it. Also, while you're at it, buy the envelopes that go with them (they are bigger than normal envelopes and say "IMPORTANT TAX RETURN DOCUMENTS ENCLOSED" in a black stripe on the front). They also have two big cutouts (one on top of the other) on the left side of the envelope. Buy some stamps, too! Bring the forms, envelopes, and stamps back to your office. IT'S GAME TIME.

And now my friends, I'm going to geek out a bit and get to the real boring (I mean FUN! stuff).

2. K. Fire up that laptop of yours and open up Quickbooks Online.

3. Hover over the "Vendors" tab (top of page) and click on "Vendor List" when it appears.

4. Scroll ALL THE WAY TO THE BOTTOM of the "Vendor List" page and click the blue button in the left corner that says "Prepare 1099-MISC Forms." You are now in the section that will allow you to prepare and print your 1099 forms. WOO HOO! You're on your way!

5. Go to section 1. It will say "1. Set up Vendors and Accounts." And click on the button that says "Assign Accounts." A thick box will pop up. Click "Box 7: Nonemployee Compensation." Then click the arrow next to "Select Multiple..." from the box on the right. Then click the actual word "Select Multiple...". You now want to go into the box that says "Select from List:" and find all of the accounts within Quickbooks that you know people or companies who should be receiving a 1099 would fall under. For example: your lawyers should receive a 1099. SO, in the box on the left titled "Select from List:" you should find the account that you use for Legal Fees and click the blue "Add >" button to move it to the right box titled "Include in 1099 Box:". Find the account for "Consultants" and move that to the right. Find the account for "Accountant Fees" and move that to the right. Find any and all accounts that you know would have been tagging any type of contractor dollars, and move those accounts (lines of text) to the right by clicking that blue "Add >" button. Then click OK. Then click OK again to close out the thick box.

6. Now. Move to section 2 titled "2. Preview 1099 and 1096 information". Start looking at your list of vendors (vendor names, addresses, and Tax ID:#s should have populated on the screen). Wherever there is a red line of text that says "Missing Tax ID#," or "Missing Address," or "Missing Name," or anything like that, you need to click on the red text and add the necessary info (into the thick box that pops up). Click save on the thick box after the info has been added. And repeat this until there are no more "missing" items. Also check to make sure that your own company name, address, and EIN number are included. If any of those are red it means your missing information and need to click on it, edit it / add it, and save it.

7. Now. Do you see the box in section 2 titled "Show: 1099 vendors that meet threshold." It's on the right side of the screen. Click that box and replace it with "1099 vendors below threshold". This list contains vendors who either were not paid $600 or more in the past calendar year (which is a requirement needed to 1099 the person in the first place), OR vendors whose expenses were attached to an account that was not included in the list of accounts you chose from the "Assign Accounts" section in section 1 above. IF YOU BELIEVE that one of the vendors in this list SHOULD get a 1099, it is probably because that expense comes from an account that SHOULD be added to the right box in the "Assign Accounts" section. In order to fix this, go back into "Assign Accounts" (in section 1) and "Add >" the account to the right hand column. Click OK and OK again. After doing this, when you go back to the 1099 screen, this name will no longer be on the "1099 vendors below threshold" list, but will instead be on the "1099 vendors that meet threshold list" (if they made over $600 last year). Go through your lists multiple times. Make sure that EVERYONE you want to receive a 1099 is now on the list when you click "Show: 1099 vendors that meet threshold."

8. IF you have everyone accounted for, and if all of their information is collected (no Tax ID#s are missing, no addresses are missing, etc)... then it is time to set up the printing.

9. To print, scroll down to section 3 titled "3. Choose how to file" and click the button that says "Print Sample 1099." A sample 1099 page will come up. Take this paper and line it up with the REAL 1099 forms you just bought from staples. Use the grid tool to adjust the text on the page up, down, left, or right to make sure they line up. Please, make sure your printer prints them the correct way. You should test and retest multiple times using blank pieces of paper. The last thing you want to do is print up all your forms the wrong way and have to trash them and go and buy new ones at Staples. You're now ready to print FO REAL!

10. If you need to print 20 1099's, load the printer with 10 1099 forms (two vendors will print on each page). As I mentioned earlier in the first paragraph of this blog post, your packet of 1099 forms will have come with four separate forms labeled Copy A, Copy B, Copy C, Copy 2 on the right hand side of the forms. Separate these forms into four separate piles. Make one pile for Copy A's. Make a second pile for Copy B's. Make a third pile for Copy C's. Make a fourth pile for Copy 2's. You will need to print FOUR SEPARATE TIMES so that you have four identical copies of 1099s, one for each form type (A, B, C, 2). Go to the printer and load one pile into the printer. Then go to your computer print up your first pile of 1099 forms by clicking on the blue button at the bottom of the page labeled "Print 1099". Then, keep them in separate piles and put them on your desk or work station so you have room to work with.

11.After you print up your four separate piles of 1099s, you match up Copy 2 and Copy B one vendor at a time and put them together into the envelopes you just bought and mail them out. For example. If one of your vendors is named Ryan Durkin... you should have one Copy 2 form with "Ryan Durkin"'s name on it and you should have a Copy B form with "Ryan Durkin"'s name on it. Put BOTH Copy 2 and Copy B TOGETHER into ONE envelope. Seal it. Stamp it. Put it in the mail. Do this repeatedly for each vendor you have until all of the Copy 2 and Copy B forms are in their respective separate envelopes and in the mailbox. You have successfully now mailed all of your vendors their 1099s! SUCCESS! But wait... there is still the IRS who needs to get THEIR copies.

12. What you should have left now are all Copy C forms and all Copy A forms.

13. You need to take all your Copy C's and put them in a safe place. Those are yours (as the business owner) to keep. I put mine in my safe in a folder labeled "2012 1099's."

14. All that remains now are your Copy A forms. These are going to go with your ONE 1096 form, which is a summary form that will sit on top of your 1099 A forms. And these are going to be mailed to the IRS.

15. To print your 1096 form, print a test page using the button "Print Sample 1096" located on your Quickbooks screen in section 3. Print off the page. Line it up to your 1096 form you bought from Staples to make sure it fits within the boxes. Then print the real 1096 form by scrolling to the bottom and clicking the blue button labeled "Print 1096". Sign the 1096 form, put your title on the form, and date it. Then put this form on top of the 1099 Copy A forms and this entire packet should be mailed in its entirety to the IRS at "Department of the Treasury, Internal Revenue Service Center, Austin, TX 73301."

That is how you make, print, and file your 1099 and 1096 forms using Quickbooks Online.



Things To End All Team Meetings With: Props & Who Needs Help

November 24th, 2012

Every team meeting I run has a beginning and an end. Every single one. It's like bookends to a big row of books. There's one at the start, and one at the finish. It's real important. Without the bookends, the books would flop around all over the place falling off the shelf like a sloppy mess. And no one likes a sloppy mess, whether it's books, your bedroom, your friend on a Friday night, or a meeting. Thank god for bookends.

I've written before about what I think is a great way to open a meeting. Now, let's talk about closing meetings.

Well! Here's what I like to do. Both are real simple, but really cool. I call them:

1. "Props" and 2. "Who needs help!?!?!"

Props is the point in time in the meeting where I ask the team: "Does anyone have props for anyone else on the team?!" To which, my fellow employees are able to call out specific employees within the company to say "Hey, John! I wanted to give you props for doing a great job on X." Or, "Hey Rebecca! I wanted to give you props for doing an unbelievable job on Y." Props is a time for employees to publically recognize people for doing things that were awesome. Typically, these nice things are about projects people are working on cross-department. Sometimes, props may be about someone who really stepped up and hit an important deadline for the company. Other times it's for a coordinated effort around launching a new campaign, or bringing in a new client, or throwing an awesome team party, or cleaning up the awesome team party, or bringing in a new hire, or pushing a really sick update that benefits users, or fixing something that's been broken for a long time. Sometimes, it's about an employee's sweet moustache (sorry Teddie... I know I said I wouldn't). Props is a great way to show someone you've worked with that you think they did a great job on something, enough to want to recognize them publically. I think it can be a really meaningful way to end a meeting. Appreciation. It's one of the most important words I've ever known. Give it a try!

Who Needs Help?!?!
"Who needs help" comes directly after "Props." It is the point in time in the meeting where I ask the team: "K! Who needs help!?! Anyone?" To which, my fellow employees are able to vocalize publically to the team that they need help with XYZ. "Who needs help" is great for providing public accountability with regards to specific projects and specific departments. It is used to help rally the team around specific projects that need to be completed on tight deadlines. For example, it is very common in our line of work at Dailybreak to want to launch a national paid sponsor's challenge quickly so that we can begin recognizing revenue and providing services to our clients and users. "Who needs help" would allow our sales team to publically remind the team that we have a campaign ready to go live on the site and that in order to go live two things need to happen: 1. The development team needs to fix XYZ bug, and 2. The marketing team needs to prepare the email campaign to our existing customer base. "Who needs help" rallies the team around specific missions that are time critical, and it provides accountability due to it's public nature. It's really effective. Give it a try!

That's all peoples! Let me know how it goes! Give me your suggestions, too! I'm all ears.


Tips & Tricks, Love, and Entrepreneurship

October 8th, 2012

On Saturday, Greenhorn Connect held a really awesome event in Boston for young people looking to learn about startups. I gave a talk at the event, and I told people I would post my deck online. So, here it is! If you weren't there, it may not make the most sense, but that's ok!

Tips & Tricks & True Love from Ryan Durkin


How Should a Founder Run A Team Meeting?

September 28th, 2012

Entrepreneur asks: "Hey Durkin, I'd like to start holding a team meeting each week with my entire team. You know, like an all-hands-on-deck type meeting. Everyone in one room. Talking about the company. Where we're going. What we're doing. Goals. Success metrics. Etc. What do you recommend?"

Great question.

First off. I think team meetings are really important. I'm not "anti-meeting" like a lot of people I've met / read about / etc. I actually think productive meetings are a great way to accomplish a ton of shit in a short period of time. Are their opportunity costs? Sure. Switching costs? Sure. I get it. Poorly run meetings can be death. But, successful meetings can provide necessary structure, kills multiple birds with one stone, provide motivation, or even reinvigorate an entire company!

I encourage people to switch up the way they conduct team meetings every six months or so. This seems like a long enough time for people to get into a routine of what to expect in team meetings, and also long enough where after six months people desire a change in pace. Change is good!

Here are two of my favorite ways to conduct team meetings:

Type A Meeting: (20 minute meeting)

1. CEO talks for 3 - 5 minutes about the business.

2. Exec team members talk for 60 seconds each about important projects in their respective departments (VP Sales talks sales, VP Marketing talks marketing, VP Engineering talks tech, etc).

3. Team members are invited to speak about interesting projects they are working on for five minutes.

4. Props: people on the team are invited to give praise to other individuals on the team who have helped them.

5. Who Needs Help?: this question is asked to the team, and team members are invited to say a project that they need help on from other people on the team publicly, providing accountability cross departments.

Type B Meeting: (20 minute meeting)

1. Moderator opens up team meeting with the "Theme of the Week."

2. One team member from each department is asked to submit a three-bullet-point update to the team.

3. Props

4. Who Needs Help?

I have attached a number of examples below of a Type B meeting. I prefer it because it allows more people on the team to talk, and is less "top-down" (CEO --> Exec Team --> Team). I also like it because it allows the entire team to rally behind a theme each week. Sometimes the theme of the week is focused around sales. Sometimes the theme of the week is focused around product. Sometimes it can be a word like "Execution," other times will be something motivational, and other times will be totally wacky and fun. The point is to send a message to the team that "This week we need to focus on our Q3 sales goal HARD." Orrrr "This week we should celebrate our successes from last week." Orrr "This week we need to pay attention to testing our platform." Etc. You get the idea.

Check out the team agendas provided below (I deleted sensitive information and all numbers are fictitious).

Each one of these is typed up the night before the meeting and is printed out and handed to team members at each team meeting. Hope this helps!

2012.09.17 - Agenda for Tuesday Morning Meetings test

2012.09.05 - Agenda for Tuesday Morning Meetings test

2012.08.21 - Agenda for Tuesday Morning Meetings test


The Next Future President of the U.S.A. Must Be Able to Do THIS

September 20th, 2012

I've been thinking a lot about the upcoming presidential election. It does seem like this election has significantly more weight behind it than any election in my lifetime, although I'm sure people could argue that either way. I do think this election is a real important one. That's why I encourage everyone in my office to vote! One site that allows you to do it is: If you haven't registered yet, do it so you can vote on election day. I hope all entrepreneurs in town encourage their team members to vote.

When I think about what's important to me in a candidate, a whole long list comes to mind. I want that person to be smart, aggressive, a great negotiator, respected and respectful. I care about making sure my life is the best it can possibly be. I care about my family and my friends and their lives. I care about causes I care about. I'm like 99% of people in that I have my own strong views on certain things, and other things I don't seem to give a shit about. There are a solid 10-20 core issues I've found people are taking into consideration for their decision on this upcoming election.

It turns out, most people I talk to are pretty well decided on who they are going to vote for for President. Out of the 30 people I asked "Who are you going to vote for in the next presidential election?" each one of them had a definite answer on one candidate or the other. I then asked whether or not they would entertain the idea of switching their vote to the other candidate. 29 out of the 30 said flat out "no."

Which got me to thinking...

I'm not on the inside of President Obama and Governor Mitt Romney's campaigns, but I imagine they are likely no longer focused on SWITCHING votes but are instead focused on inspiring their followers to do two things:

1. Show up, and

2. Bring their friends, neighbors, and family to the election booth with them. 

This election is going to be about showing up. Not switching votes.

If you are to expand any energy at all, it should be to drive/walk/run/bike to the election booth. If you have any interest in expanding any MORE energy at all, it should be to drive/walk/run/bike your friends, neighbors, and family to the election booth.

Romney will have to inspire this intense passion and feeling in people to do this if he wants to win the WhiteHouse. And Obama will have to do the same to keep it.