How to Increase Property Value as a Real Estate Investor

As a real estate investor, you want to be able to increase the property value of your properties as much as you can. If you make use of specific methods, you should be able to get the most out of your investment. Read on to explore how you can increase your property value as a real estate investor. These methods won’t be too hard to implement, and they should really pay off in the end. 

Clean the Property Thoroughly

Cleaning the property thoroughly is the first thing that you should do when you’re looking to make improvements. Clean the home on the outside and the inside to make sure that it looks great. Some investment properties might have issues that will need to be addressed. Make sure that you take the time to clean things up before you start thinking of selling it or renting it out. 


A little bit of paint can transform a home into something more beautiful. If you want your property to increase in value, then you should always try to make it as presentable as possible. Take the time to paint the home so that it looks the best that it can. This will help you to get more out of the property when it comes time to sell it off. 

Give the Property More Curb Appeal

You want your property to stand out in a positive way from the road. Taking the time to increase the curb appeal of your property will make a difference. Plant some flowers and plants to add a bit of charm to your property. You can also consider how the shutters look, whether the deck is presentable, and other options that can help to increase the curb appeal. 

Update Flooring

If your property has older flooring at the moment, then you might want to make some changes. Get rid of the old carpeting and buy something new that will look visually appealing. You could also consider buying hardwood flooring or some other type of flooring. Improving the flooring situation in the home will increase property value, and it’ll make it easier to get buyers interested in the house when you’re looking to sell. 

Get New Siding

Getting new siding can be very helpful as well. If you want the value of your property to increase, then new siding will help you to accomplish just that. The house will look a lot nicer with new siding, and it’ll add a lot to the value of the home. This will cost you a bit of money, but it should be worthwhile since it adds value to the house while making it something that will appeal more to the buyers. 

from Moss Sidell | Real Estate Attorney

Increasing Your Productivity as an Entrepreneur

Moss Sidell Attorney Productivty

Every entrepreneur wants to be able to stay as productive as possible. The problem is that many entrepreneurs struggle with productivity for various reasons. If you are hoping to increase your productivity, then there are certain things that you should be doing. Keep reading to examine methods for becoming a more productive entrepreneur. 

Use Your Time Intelligently

Using your time intelligently is going to be the best way to increase your productivity. Some entrepreneurs get too wrapped up doing several small things that they don’t get the most important tasks completed. Try to prioritize the things that need to be finished right away and then focus on little tasks once you are done. It might be a good idea to create a list of tasks that you need to prioritize and then work your way through them in order. 

Eliminate Distractions

Many entrepreneurs have a difficult time and become too distracted. You’re the boss and this means that you have a lot going on. You also might be distracted by everyday life stuff just like anyone else would be. Keep your personal phone turned off during work hours, if possible, and eliminate distracting elements from your office that will keep you from getting work done. 

Maintain Your Health

If you aren’t maintaining your health properly, then you’re going to encounter many productivity issues. People who don’t eat right won’t have the energy that they need later on in the workday. Also, it can be helpful to exercise regularly so that you have the stamina to handle the long hours you’ll need to put in as an active entrepreneur. Try to focus on your fitness and diet so that you will have the necessary tools to get the job done. 

Stop Being a Perfectionist

Being a perfectionist can actually hurt your overall productivity. If you get so wrapped up in little details that you can’t finish things on time, then you’re going to fall behind in your set schedule. It’s essential to do good work, but you can’t be so meticulous that you aren’t able to wrap things up. Understand that nothing will ever be completely perfect so that you can be a more productive entrepreneur. 

from Moss Sidell on Business

How to Build a Modern Digital Office Space That You Will Love

There was a time when a new worker required a desk, a computer, an expensive phone, and four walls. That time is gone. Whether you hire contracted freelancers or host remote workers at your company, today’s digital environment makes it possible to eschew the usual trappings of office life for a far more digital, remote experience. With the right structure in place, you don’t have to give up the collaboration or personal touch of a traditional office. Here are some of the tools that can help you build that office:

Cloud Storage and Office Management

It starts with your digital infrastructure. How will you store the key documents and files that you share with your co-workers and employees? How can you collaborate on these same documents to ensure that work gets done on time? Here are a few suggestions:

  • Google Drive and Google Docs. Whether comparing notes on content for your blog or building group projects for business presentations, you’ll have just about everything you need for remote word processing and more with free Google accounts. Google Calendar syncs neatly with plenty of apps these days so you can automatically schedule meetings and tasks without having to take on additional steps.
  • Dropbox. Many business owners today choose to supplement their cloud storage with at least one Dropbox account—just to have a backup. Dropbox’s free account currently offers enough storage for most people to handle the demands of a modern business, but there’s also a Dropbox Business account for more robust team needs.
  • Microsoft OneDrive. People who use PCs often find that OneDrive fits in neatly with the infrastructure they already have in place. OneDrive’s easy offline access features also make it possible to handle a variety of business needs even when the Internet’s down—though if you have remote workers, this isn’t usually a concern.
  • Use Zapier to automate your most common processes; for example, you can use new tasks on Trello to automatically create Google Calendar reminders for new project assignments.

Meetings and Online Conferencing

What defines a modern digital office is that it’s not limited to the four walls around your computer. But to keep tabs on a remote team, you’ll have to be able to check I from time to time. That means online meetings and conferencing:

  • GoToMeeting. GoToMeeting is one of the most popular solutions for handling remote workers, with some 18 million users per month across the globe. They offer easy screen sharing, high-quality video/audio, and great features like commuter mode, voice commands and cloud recording.
  • This easy-to-use meeting tool allows for one-click screen sharing, personalized URLs, and the everyday features you rely on such as audio, recording, scheduling and remote control.
  • Calendly is a nice tool for avoiding the game of email tag that usually happens when you’re trying to match schedules with someone else.

Phone Calls and Voicemail Systems

You no longer need a landline in the modern digital office. But that doesn’t mean a smartphone alone will suffice, either. We recommend that you split up your personal and business calls with a phone system that easily delineates between the two, giving you a separate business phone number.

Grasshopper’s solutions include a separate toll free number for your business, a voicemail system, multiple extensions, call forwarding, and even business texting through your usual phone.

Strategies for Remote Working

A modern digital “office” means you’re not always tethered to one specific location. As long as you have the software and infrastructure in place to handle it, you can simply use an Internet connection to get most of the work done. Zapier has highlighted a wide range of different home offices where many people can get by with a simple Internet connection and a laptop.

But just because it’s easy doesn’t mean you shouldn’t plan effectively. Here are some tips for keeping work going while you’re handling business from the home or on the road:

  • Get off of paper as much as possible. Even if you have a business presence that requires a lot of paperwork, there are still some ways to reduce paper usage, including software that tracks printer usage and arranging for as many paperless statements as possible. It’s also a good idea to digitize essential documents to have electronic backups in the case of emergencies.
  • Set clear rules and guidelines for remote workers. If you hire a remote worker, make sure that you work with them early on in the process so they understand the expectations of a remote office. How much work will you expect them to do? What are your policies on sick days? Vacations? One rule of thumb is to keep your business running like a traditional business, even if many of your workers now handle their job from a remote location.
  • Find co-working spaces when you can. If you work in a digital office from home, you might find it beneficial to find co-working spaces when you can, such as working out of coffee shops with free WiFi or seeking out a co-working space in your area.
  • Use an “upside-down pyramid” schedule. In other words, start with the foundation of your work as soon as you can. Begin with the most important task of your day. If you work out of a mostly digital office, it’s possible for your work day to run into all sorts of non-office issues that can derail your productivity. That freedom can be a great thing. But it also means you’re responsible for getting things done without the traditional 9-5 structure. Get the most important work out of the way first to ensure that even if your day gets disrupted by mid-afternoon, you can still recover the next day.

Building a Flexible Digital Office

There is enough technology out there that you can handle most work with a laptop and an Internet connection. But if you want to maintain the standards and function of a larger office, it helps to supplement these basic tools with the infrastructure to maintain the appearance of a full corporate presence—without all the expense.

from The Grasshopper Blog – Insights for Entrepreneurs to Build a Modern Digital Office Space That You Will Love/

No More Lost Leads: How to Capture and Keep Potential Leads

How many leads did you lose last month?

Trick question. It’s hard to tell the opportunity cost when those leads never went your way to begin with.

But there is a type of lead that companies too often ignore: the potential leads that for some never became full-blown leads for your company. This can happen for a few reasons:

  • Leads might jump into an order form and fill up a “shopping cart” only to abandon the cart and close out the window.
  • Some leads may come to the cusp of signing up for a newsletter, only to decide at the last minute that they’d rather keep surfing the web.
  • Other leads might bookmark your lead page for later—only to never return.

In each case, you’re capturing potential leads, but for some reason or another you’re not keeping them as genuine leads for your business. Here’s a guide for rectifying that situation:

Evaluating Your Current Lead Strategy

The first step is to better understand what your current lead strategy is—and how well it might be working out for you. Here are a few tools to help in that process:

  • Use a tool like Website Grader to get a sense of how you’re currently doing with potential leads. This will yield you insights like your page size, page speed, and mobile responsiveness to ensure that you’re not turning away leads before they ever happen.
  • Supplement your Google Analytics with tools like Leadfeeder or Ahrefs. Leadfeeder gives you more insight about who’s visiting your website, which helps you craft a strategy for capturing these leads more specifically. With Ahrefs, you’ll get more insights as to the strategies your competition is using to capture more data-driven leads.
  • Integrate A/B testing into your lead strategy. If you have multiple ways of capturing leads, it only makes sense that you’ll want to test which ones need optimization and which ones are delivering the kind of performance you need. For example, you might start with multiple versions of a “contact us” page to see which one tends to yield more results. The key to testing effectively is that you’ll identify the “invisible” leads you could have captured with a better lead form, but never knew because you never tested alternative pages.

Optimizing Your Website to Point Your Audience Toward Lead Conversion

Once you have a sense of where your opportunities may be lost, it’s time to create new strategies to capture the leads you’ve been missing. Here are a few to consider:

Create more landing pages.

According to HubSpot, companies with 30+ landing pages tended to generate about 7 times as many leads as companies with only 1 to 5 landing pages. This doesn’t mean that more is necessarily always better, but it does suggest that the companies that are actively creating landing pages and testing them for specific purposes are finding better results. If you only have one landing page that you never test, now’s your wakeup call.

Consider integrating live chat.

Live chat (42%) is beginning to outpace even email (23%) and social media (16%) as the “leading digital content method.” That means that it’s also expressing its potential to drive visitors to transform into leads. As visitors ask questions and explore the live chat feature, they can easily be swayed toward a landing page of the company’s choice—preferably one that’s already been optimized for someone asking those same questions.

Give your leads something to do.

Evaluate your site from the audience’s perspective. Live chat (see above) works because it gives customers something to do. But there are other ways to encourage people to move through your lead funnel, including:

  • Download incentives. One of the most popular lead capture tools in the world is to create a factsheet worth downloading and encourage people to trade their email address in exchange. Download incentives are popular for a reason: they work.
  • Create valuable content. Whether that valuable content comes in the form of an insightful blog post or an online tool visitors can use for free, it doesn’t matter. What’s key is that you create something that people will find worthwhile and use that content to drive their attention toward your lead generation funnel.

Add a personal touch.

With personalized calls-to-action converting some 42% more people than the basic CTA, one thing is clear: we like the sound of our own name. That’s one reason that personalized email headlines tend to do better, even if we already know as the recipients that it was an electronic form that enabled that level of personalization.

How to Retarget Leads that Never Became Leads

Sometimes, you’ll just lose out on leads. It happens. You may not have any explanation for it. Heck, even your leads may not be able to explain why they clicked away.

In that case, you can use a strategy of retargeting to influence how many of these leads you retain.

For example, Google Adwords Remarketing allows you to create advertising for very specific cases. You can create advertisements tailored to those who might have browsed your website but never fully made a decision one way or the other.

You can also use Custom Audiences on Facebook to reach out to highly specific customer segments. By implementing a Facebook pixel on your site, you can even create a custom audience of people who have already visited your website. As is the case with Google Adwords Remarketing, you can then construct advertisements specifically tailored to those who didn’t pull the trigger on an order.

Retaining More of the Leads You Worked Hard to Create

Before you go out and spend money on advertising or SEO, you should focus on making your site a better place for the people already visiting it. Retarget your customers, increase the personal touch, and begin testing your lead funnel solutions to ensure that you retain more of your visitors and turn more of them into leads. Then, the next time you spend a dollar on advertising, you’ll be confident that your site has what it takes to generate a worthy ROI.

from The Grasshopper Blog – Insights for Entrepreneurs More Lost Leads How to Capture and Keep Potential Leads/

How to De-Clutter Your Business Life

Clutter comes in many forms. It’s tempting to look at the pile of papers on your desk and view that as the only clutter weighing you down—but chances are, it’s the least of your problems.

Anyone who runs a business knows that clutter can be more substantial than that, including:

  • An email inbox with hundreds of messages that need sorting
  • A schedule that overwhelms you and forces you to cancel meetings
  • Taxes that are so complicated that they start to take over your life
  • A list of voicemails to which you have yet to respond

Just as you’d sweep away the cobwebs in the corner of your basement, your business needs its occasional spring cleaning, too. Here’s why.

Why You Need to Reduce Mental and Physical Clutter

Psychology Today once tallied the mental costs of clutter, pointing to eight distinctive negative effects clutter can have on our lives. From creating feelings of guilt and embarrassment to the constant stressor in the back of your mind that your workday isn’t officially done, clutter can place an enormous mental burden.

The same is true of both physical and mental clutter. A physical mess is another chore we have yet to do, so it becomes a mental challenge. And mental clutter can pile up in physical ways, weighing visibly on our email inbox or piling up in a list of expense receipts you have yet to go through. After a certain point, these tasks lose all meaning and simply become part of an overwhelming stressor weighing on our everyday lives.

Strategies for Reducing Business Clutter

With that in mind, how should you approach the “business” clutter in your life? It’s tempting to go the route of Marie Kondo and the KonMari method. But these systems focus on domestic clutter. What happens when your business life needs cleaning, too?

Here are some suggestions to help you get started:

  • Identify the clutter. If you have only a vague sense that something in your work is weighing you down, but you don’t know what it is, get clear about what you want to remove from your work life. Write down a list of the thoughts that are more stressful to you at work and ask yourself if you notice any common themes.
  • Delegate when possible. However frugal you might be, whenever you can delegate a task that’s weighing heavily on you, you should try to see if there’s a way you can do it. Whether that means hiring an accountant to handle your increasingly-overwhelming taxes or simply having someone come in and clean your desk, you don’t have to add to your daily tasks. Outsource it.
  • Always keep your business and your personal separate. According to, the blurring of personal and work lives is the main cause of stress for 20% of those in the workforce. Consider that one of the problems business owners have is looking up a wide range of expenses when they’re not sure which ones were for business and which ones were personal. Try to create systems that handle the sorting for you. Use a unique business checking account and unique business credit cards. Combined with proper bookkeeping software that logs every transaction, you’ll never have to worry about collecting and sorting huge piles of receipts again.
  • Start small if need be. Sometimes the overwhelming idea of tackling a huge task like our email inbox can prevent us from taking any action at all. Who wants to start a four-hour task when they can spend the next ten minutes doing something more fun? That’s why it’s important to chip away at the clutter even when you know you won’t get to it all in one day. If you can keep the arrow pointing in the right direction, you’ll eventually arrive at a point in which the clutter no longer overwhelms.

Avoid these Key “Business Clutter” Mistakes

After taking steps to reduce your clutter, it’s important not to let it happen again with a few preventative measures:

  • Build a replacement system. Even if you go through and delete every email in your inbox, failing to replace your old system with a new one just means you’ll get back in the same old habits. This is a great time to investigate apps like Newton that you can use for long-term inbox maintenance. Do similar research with the other areas in your life that you need to improve upon. If you’ve struggled with your invoicing, is it time to invest in a solution like FreshBooks?
  • Schedule regular time for clutter maintenance. As long as clutter remains a problem for you, it’s important to put aside some time every so often to handle your clutter—even if it means simply emailing someone who can help you. Schedule regular maintenance time to sit down and focus solely on decluttering your business life.
  • Stop adding to your workload. If you can master the word “No” when you’re overloaded, you’ll do a lot to keep your business running smoothly. For new businesses, turning down additional clients can feel like a major mistake—until you realize that biting off more than you can chew is just as bad a habit as doing too little at work. Stop adding to your workload and give yourself some freedom by saying the occasional “no.”
  • Separate your business and your personal life with effective systems. For example, using Grasshopper’s business number allows you to filter out business calls from personal calls, operating both seamlessly on the same device.

Building a Better Way of Handling Business Clutter

De-cluttering your business life requires a great deal of introspection. It requires being honest about yourself and the way you approach your business every day. It requires a little work to get started. But it will be well worth the investment of time and effort it takes, because you’ll be better able to handle your daily workload—as well as build stronger systems for managing growth in the future of your business.

from The Grasshopper Blog – Insights for Entrepreneurs to De-Clutter Your Business Life/

A Step-By-Step Guide to Catching Up On Your Bookkeeping

Tax season is coming—it’s inevitable. Getting your books tax-ready ensures you’re compliant with the IRS recordkeeping requirements, meaning no late fees, no surprises, and a successful tax return that won’t cost you extra time later on (we know you’re busy). 

Bench was started so you wouldn’t have to do your own catch up bookkeeping. But for the do-it-yourselfers, this step-by-step guide will help you get through your bookkeeping backlog in no time. 

Step 1: Collect Receipts & Invoices

Start by collecting all receipts and invoices related to your business expenses. There are many different types, so we’ll outline the most important ones. 

Customer Invoices

Review your customer accounts and double check that you’ve collected all customer invoices for the tax year. Depending on whether you’re using a cash or accrual method, you’ll record these differently. 

Debt Collections

Review your customer accounts for any bad debt expenses. In order to deduct the cost of bad debt from your tax return, you will need to prove to the IRS that you have taken reasonable steps to collect the debt. Bad debts can be claimed by using either the specific charge-off method or the nonaccrual experience method

Business Expenses

Collect receipts from all business purchases you have made during the tax year. Use this handy list of small business tax deductions to double check that you’re tracking and claiming every deduction available to your business—because who doesn’t love saving on taxes?


Vendor Accounts

Review your vendor accounts to ensure that you have paid them all in full. Make sure you have a copy of every bill from each vendor activity and, if you don’t, contact the vendor and ask them to send you a copy.

Important to note: Vendor accounts include bills for business activities that are still currently operating in your business’s closing period.


Step 2: Reconcile Your Bank Records

Reconciling your bank records accomplishes two things: 1) It ensures you don’t miss any business expenses or important records from Step 1, and 2) It helps you catch any mistakes your bank may have made.

You can do this by comparing each transaction from your bank statement with the same transaction in your company accounting records. If the transactions don’t match, identify and fix any errors to ensure they balance out.

Step 3: Separate Personal and Business Expenses

Keeping your personal and business expenses in the same account is known as piercing the corporate veil—which may result in you being held personally liable for your business’s debt and actions. The sooner you separate your business and personal expenses, the better. Learn how to open a small business bank account and keep your finances separate.  


If you’re unsure about whether a purchase qualifies as a deductible business expense, learn how the IRS differentiates personal and business expenses.

Step 4: Create Digital Records

If you haven’t done so already, there are countless benefits to making your business paperless. As you process your paperwork, create digital records of receipts and important documents. Here are a few of our favorite tools to help you go paperless:

Step 5: Submit Forms for Contractors & Employees

If you paid independent contractors and/or employees during the tax year, there’s a good chance you’ll need to file the following forms:

Independent Contractors: Form W-9 & Form 1099-MISC

If you paid an independent contractor more than $600 for work during the year, you’ll need to submit a Form W-9 and a Form 1099-MISC. A W-9 requests a contractor’s taxpayer information. The contractor completes this and returns it to you. You then use the information on the contractor’s W9 to issue a 1099 to the IRS. If you’re new to the process, and unfamiliar with the deadlines, read How (and When) to File a 1099 first. 

Employees: Form W-2

You’re required to file Form W-2 for all employees.

Step 6: Review Your Books With a Professional 

When you’re a small business, doing it yourself is often the least expensive option. But tax professionals can help eliminate errors, help you claim all of the deductions available to your business—which may end up saving you money in the long run—and can also represent you in the event of an audit. Developing a relationship with a financial pro, well before you need their help, will prevent last-minute scrambling and bring you peace of mind that your books are in order.

CTA: If you’re a small business owner who could use a helping hand—the expert bookkeeping team at Bench can get you up-to-date with their Catch Up Bookkeeping Service. 

from The Grasshopper Blog – Insights for Entrepreneurs Step by Step Guide to Catching Up On Your Bookkeeping/

Easy Guide to a Painless Tax Season

Do the words “tax season” make you shudder? You’re not alone. Over half of US adults say tax season stresses them out. And when you run your own business, your tax time heebie jeebies are bound to be even more severe. 

Tax season is faster and easier when your bookkeeping is organized. And our partners at Bench will handle all your small business bookkeeping, and even file your taxes for you.

But if you’re filing your own taxes, read on. We’ll cover all the forms you need to file and deadlines you need to meet—plus how to file on time or get an extension. 

The Documents You Need to File Taxes

When you file your tax return, you must be able to prove what you earned and what you spent —for the sake of reporting income, as well as claiming tax deductions. These records don’t get sent in with your return, but you’ll use them to calculate your total income and expenses for the year. And you need to have them on hand in the unlikely event you’re audited. 

Basic Info for Filing Small Business Taxes

  • Personal and business info: Your address, the address of your business, your full name, and your Social Security Number (SSN).

  • Last year’s filing: Having your previous return on hand makes it easier to complete this year’s return and keep track of info like depreciable expenses.

  • A tax ID number: There are a variety of different numbers you may use as a tax ID number—from your SSN to your employer identification number (EIN). Not sure which to use for your business? This article on tax ID numbers offers a handy rundown. 

Records of Small Business Revenue

  • Invoices you sent to clients: Keeping copies of sent and paid invoices helps you track your revenue, and can support your case if your revenue or income are ever called into question by the IRS.

  • Records of goods sold: Cash receipts, or transaction lists from an online store or point of sale, can serve as a record of revenue you’ve earned.

  • Other sales records tracking revenue: It’s smart to hold on to any records of revenue you’ve got. In lieu of organized bookkeeping and regular income statements, you can use them to calculate your revenue for the year.

Records of Expenses

By subtracting your expenses from your revenue, you get your total income for the year. That’s essential for filing. Also, many expenses are deductible—and if you make deduction claims, you’ll need to back them up.

Be sure to hold on to: 

  • Rent receipts

  • Office supplies receipts

  • Employee salaries

  • Mileage records

  • Other deductible expense receipts 

Annual Financial Statements

An income statement, balance sheet, and (if you use accrual accounting) cash flow statement for the year will make filing easy. Comprehensive financial statements give you all the info you need to file. If you don’t have financial statements for your business, now may be the time to hire a bookkeeper.

Essential Tax Forms and Deadlines

Once you’ve got your documents in order, get the forms you’ll need to file. The exact forms you’ll use, and the deadlines for filing, depend on your business structure.

Tax Forms and Deadlines for Sole Props

Filing Deadline: April 15, 2019 (the same as your personal taxes)

There’s no need to file a separate return for your business. Report your business income and expenses on Schedule C of your personal tax return. To claim itemized deductions, list them on Schedule A.

The IRS instructions will walk you through the process of tallying your expenses and revenue for the year, and determining your income. 

Tax Forms and Deadlines for LLCs

Filing Deadline: April 15, 2019 (single member)

Filing Deadline: March 15, 2019 (multi member)

If you’re a single member LLC, you’ll file your taxes the same way you would as a sole prop. 

If you’re a multi-member LLC, you elect to file taxes as either a partnership or an S corporation.

Tax Forms and Deadlines for Partnerships

The partnership files Form 1065, and each individual files a Schedule K-1 to report what they’ve made and lost during the year. Partners claim unreimbursed business expenses on Schedule E.

Partnership filings, and Form 1065, can get pretty complex. For this reason, we recommend working with a tax professional to file your taxes.

Tax Forms and Deadlines for C Corporations

Filing Deadline: March 15, 2019

In addition to your personal tax return, you’ll file one for your corporation using Form 1120. This form is similar to Schedule C of your personal tax return, but more complex—and separate from your personal finances. Most business owners hire an accountant to help with Form 1120. 

Tax forms and deadlines for S Corporations

Filing Deadline: March 15, 2019

You’ll file a Form 1120S for your corporation, and each shareholder will need to report their profits and losses with Schedule K-1. Similarly to a C corporation return, most S corps get help from an accountant to file taxes

Tax Forms and Deadlines for Businesses that Hire Contractors

Filing Deadline: Sent to recipients by January 31, 2019

If you’re paid $600 or more to a contractor, you need to file Form 1099. Once copy of this form goes to the IRS, for the sake of filing your own taxes; another copy goes to the contractor, so they can use it to file their taxes. You need to file a separate Form 1099 for each contractor.

How to File Taxes Online

Gone are the days of paper filings. The most efficient (and popular) way to file taxes with the IRS is online. 

To file your taxes online, you have two options: Free File, or Free File Fillable Forms.

IRS Free File

The IRS has partnered with 13 providers who offer free versions of their accounting software that you can use to file your taxes online. You’re automatically enrolled in Free File once you sign up with one of these providers—you don’t sign up through the IRS website.

Most providers offer a basic software package for free. These typically aren’t able to cover all the needs of a business—such as filing itemized deductions. You’ll need a paid version for that; the packages recommended for sole props range from $54.95 ( to $94.99 (H&R Block).

IRS Free File Fillable Forms

Essentially, Free File Fillable Forms lets you complete IRS forms online, through the IRS website. These forms will do basic calculations for you, but they don’t check for errors.

Fillable Forms will automatically calculate your tax refund, and you can elect to have it transferred directly to your bank account. You can also pay your taxes online.

If your business is small and relatively simple—like a sole prop—and you’re already experienced with filing taxes for your business, Fillable Forms may be a good choice. 

Otherwise, the process could take a while, and you’ll run the risk of making errors. In that case, you may be better off having someone file your taxes for you.


If you’re short on time and energy this tax season, and don’t want to wade into the depths of filing by yourself, consider BenchTax. With BenchTax, a team of professional bookkeepers will get your books caught up to the current month; then, they’ll work with tax experts to get your taxes filed accurately and on time—taking advantage of as many itemized deductions as possible.

How to Get an Extension

If it looks like you’ll be late filing taxes, file for an extension ASAP. It will save you from IRS late filing penalties, and getting an extension is pretty straightforward.

Filing a tax extension for your sole proprietorship or single-member LLC

If you plan to pay your taxes online, you can get a six month extension through the IRS payment portal.

Otherwise, you can request an extension by filing IRS Form 4868.

Filing a tax extension for your multi-member LLC, partnership, or corporation

You can file for a six month extension using IRS Form 7004

File Early, Rest Easy

If you can, file your taxes early—meaning, well before the deadline. This may take some prep, but it has advantages.

First, you’ll get your tax refund earlier. Remember, a tax refund is your money—you just happened to overpay it to the IRS, and they’re holding on to it. Your money isn’t collecting interest while the IRS holds it. The sooner you get it back, the sooner you can put it to work for your business.

Second, you’ll have the info you need to start planning your estimated taxes for the coming year—ticking one more item off your tax to-do list.

To file early, you’ll need tip top books. The more organized your books, the easier it is to get the numbers you need to file your return. The best way to stay organized is to do your bookkeeping throughout the year, rather than handling it all in one mad scramble come January.

Ready to get your books in order? Check out Bench. They’ll do one month of bookkeeping for you, free.

Tax time doesn’t have to be stressful. And it won’t be, so long as you have everything you need to approach it in an organized way. Your filing date, and the forms you need, vary according to your business structure—so make sure you know what’s what before the deadline comes.

from The Grasshopper Blog – Insights for Entrepreneurs Guide to a Painless Tax Season/