Complete Guide to Launching Your First Side Business

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Sure you could probably start a side business in a few hours. But if you want to make it a sustainable source of income, you need to do some extra work.

The U.S. federal government views any earnings you bring in from your gig as taxable income, even when it’s on top of your full-time job.

So when you’re starting a side business, it’s important to treat it like a real company. You’ve got to follow the appropriate local and federal laws as well as guidelines when you’re setting it up.

Taking the proper precautions early on can save you a lot of headaches later on. Most importantly, it can prevent you from receiving a massive tax bill or penalty come tax season.

How to start a side business in 8 steps

If you plan on becoming a Shipt shopper or working with another established company, the good news is the business has already done a lot of the work for you.

The company has already taken care of the logistics of insurance and permits, and you’re considered an independent contractor. All of that groundwork makes it easier on you when you’re filing your taxes later on.

However, if you want to go it alone and start a side business on your own, a lot more work is involved on your end.

Whether you plan on dog-sitting or dream of launching a career as a freelance writer, by starting your side gig you are essentially becoming a business owner.

Even if it only makes a fraction of the money you make at your full-time job, you are still subject to laws and taxes governing small businesses.

Here are eight steps you may need to take when launching a side business, depending on your state and county.

1. Decide if you need an Employer Identification Number (EIN)

Most side hustles do not need an EIN. At least, not at first. However, that can change as your business grows and if you decide to hire staff.

For example, if you start a business cleaning houses, you might start out as your sole employee. In that situation, you do not need an EIN at all.

But, if your business expands beyond what you can manage on your own and you decide to hire help, then you will need to open an EIN to file taxes appropriately. It’s also important for identifying what you pay your employees or contractors.

One other caveat. If you’re working as a contractor for your side business and you don’t want to use your social security number on W-9 forms, then getting an EIN number is a smart idea. You can use that on your paperwork instead.

2. File the appropriate business licenses and permits

To run a side business legally, there are licenses and permits you need. Some companies, like those that sell liquor or firearms, require a federal license and permit.

But according to the U.S. Small Business Administration, it’s not just liquor and arms dealers that need to worry about permits. On their site, they state that nearly every business needs some form of permit or license to operate.

Rules vary from state to state and depend on what kind of business you run. For example, in some areas, you need a permit to run a business out of your home. Even if you are just working at your computer.

Here are some of the most common licenses and permits.

Home business license

Most states and counties require a home business license if you do any work from home.

It provides revenue to the local government and notifies authorities about your activities. Most home licenses cost between $25 and $50.

Occupational permit

Depending on what your business is, you may need an industry-specific permit.

For example, if you intend to sell baked goods, you’ll need a food processing and safety permit. Salons, daycare facilities, dog-sitters, and more all need occupational permits.

Doing Business As (DBA)

If you are doing business under a name other than your own, your city or state will require you to file a DBA application, which usually has a fee.

To find out what licenses and permits your particular business needs, visit the U.S. Small Business Administration site and click on the appropriate state.

3. Select a business structure

Most freelancers and side hustlers start out as sole proprietors. And when starting a side business, that’s usually a smart option.

But over time, your needs may change. You may eventually want to consider switching to either a limited liability corporation or incorporating the business. Here’s a breakdown of your options.

Sole proprietorships

Under a sole proprietorship, one person is in business for themself.

It’s pretty much the easiest type of business structure to take on. You don’t have to file any extra paperwork, and there are no legal formalities when you want to change up your business.

However, as a sole proprietor, you are completely responsible for any debts you take on due to your business dealings.

For example, if you get into a dispute with a client and he sues you, because you are a sole proprietor, your personal assets are fair game in a suit.

When you want to expand, raising capital can be difficult, too. There’s only one share of the business–yours–so there’s nothing to portion out to investors.

So if you intend to grow your business beyond a one-person operation, you may want to look at other options early on.

Limited Liability Corporation (LLC)

An LLC is one of the newest business structures, but it’s becoming increasingly popular.

Essentially, an LLC protects your personal assets from business debts. Earnings and losses are reflected on your personal income tax returns. Therefore, LLCs have fewer paperwork requirements than other structures.

Many freelancers, especially freelance writers or designers, opt for an LLC to protect themselves in case of lawsuits.

How the government taxes LLCs differs from state to state. So if you have clients located throughout the country, the different taxation rates can make managing your business finances more complicated.

Forming an LLC can also be more expensive since you often need to hire a lawyer or legal service to do it for you. And some states require that an LLC have at least two or more partners.


If you plan to grow your business into a multi-person, full-time operation with shareholders and investors, incorporating your business may be for you. New businesses can incorporate as either a C class or S class company.

The government taxes C corporations twice. First on its profits, then on the distributions given to shareholder. By contrast, S corporations are taxed just once. However, they cannot offer stock options.

4. How to file as a sole proprietor, LLC, or incorporate

Filing your business structure can cost anywhere from $200-$1,000, depending on your state’s fees.

And depending on how complex your state’s laws are, it may be a good idea to hire a lawyer to handle it for you since the system can be difficult to navigate on your own.

Fun fact: legal services like LegalZoom can help you file appropriately for far less than it would cost hiring a private attorney.

5. Get insurance

While many side gigs can be started without a lot of upfront investment, one of the things you should consider before going too far into developing your business is insurance for your side hustle.

Whether you are a dog-sitter, driver, cleaner, or computer repair-person, insurance can go a long way to protect you in the case of an accident or mistake. While you may think that sounds like overkill, accidents happen all the time.

Imagine if you bake gourmet cookies and a child has an allergic reaction. Or you’re walking a dog for a client and the dog bites another dog.

Or better still, if you’re a writer and your laptop is stolen, your clients’ data could be compromised. You could end up in court and liable for thousands of dollars in damages.

Insurance is an essential safeguard for both you and your side business. Trust me.

But insurance for a side gig doesn’t have to wreck your budget. You can get a policy for $300-500 a year. If you’re not sure where to start looking for one, talk with an independent insurance provider about your needs and to get a quote.

6. Develop a system for tracking expenses and profits

Managing taxes and income can be difficult. If you want to make your life (and your accountant’s) much simpler, you should come up with a system for tracking your expenses, profits and managing receipts ASAP.

Start by doing the following.

Open a business bank account

While the IRS doesn’t require you to have a business bank account if you have a side business or freelance, it can make things much easier for you.

With a business bank account, you can just look at your bank statements and get a complete snapshot of all of the income that came in and all of the expenses you paid.

Those statements are invaluable and will make preparing your taxes a more streamlined process.

Open a business credit card

Similarly, opening a business credit card to use for expenses related to your side business can be a huge help.

If you use your personal card, it can be easy for expenses to get lost and for you to lose out on important deductions. Having a designated card just for your business costs will make managing your finances much easier.

Keep receipts

You should always keep copies of your receipts to help you during tax season when you file your returns.

And, those receipts can also help protect you in the case of an audit. However, managing a bunch of loose receipts can be burdensome and take up a lot of space.

The good news is there are receipt-management systems that are affordable to help you organize and electronically store your receipts. Wave, NeatReceipt, and Shoeboxed are just a few options you can use to manage your records.

7. Figure out how you will handle taxes

One of the most overlooked parts of running a side business is paying taxes on your side income.

But remember, all of your gig earnings are taxable. And it’s important to plan ahead so you don’t get hit with a surprise tax bill in April.

As a side hustler or freelancer, you have two options for managing your taxes: submitting estimated or quarterly taxes, or adjusting your W-2 withholdings.

Estimated taxes

If you have a full-time employer, they withhold federal and state taxes for you.

But with a side gig, setting aside money for taxes is entirely up to you. And if you don’t pay enough taxes throughout the year, you can get hit with a hefty underpayment penalty.

If you expect to owe more than $1,000 in taxes for the year due to your side gig, then you need to file estimated taxes. To figure out what you owe, estimate what you think you’ll make for the year. Then, send in four payments throughout the year.

To prepare for those regular payments, set aside 20 to 30 percent of everything you earn and put it in a tax savings account that you touch only when making tax payments. That way, you don’t have to scramble to come up with the money for your tax bill.

If this sounds complicated–and it is–you may want to hire a tax professional. Alternatively, you can use TurboTax Self-Employed software to manage quarterly taxes.

Adjust W-2 Withholdings

If estimated taxes sound like way too much work and you have a full-time job, you can skip quarterly payments and just adjust your W-2 withholdings.

Calculate how much you owe in taxes for your side gig, divide that number by the number of paychecks you get in the year, and set up a meeting with your human resources department.

You can fill out a new W-2 where you withhold extra amounts of your income for federal and state taxes, eliminating the need for estimated taxes.

While you’ll see less money in your core paycheck, it will save you the time and stress of managing quarterly taxes and setting aside money in a separate tax account.

8. Launch your side business

While getting your side business off the ground the right way may be more time consuming than you originally thought, it’s well worth the effort.

Doing your research and filing the appropriate paperwork ensures your business will succeed in the long run and allows you to focus on growing its earning potential.

With your business making money, find out how much your side gig can help you save on your student loans with our prepayment calculator below. Moonlighting just a few hours a week can make a huge difference.

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Here are the top 8 lenders of 2020!
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1 Important Disclosures for Earnest.

Earnest Disclosures

To qualify, you must be a U.S. citizen or possess a 10-year (non-conditional) Permanent Resident Card, reside in a state Earnest lends in, and satisfy our minimum eligibility criteria. You may find more information on loan eligibility here: Not all applicants will be approved for a loan, and not all applicants will qualify for the lowest rate. Approval and interest rate depend on the review of a complete application.

Earnest fixed rate loan rates range from 3.20% APR (with Auto Pay) to 6.99% APR (with Auto Pay). Variable rate loan rates range from 1.99% APR (with Auto Pay) to 6.89% APR (with Auto Pay). For variable rate loans, although the interest rate will vary after you are approved, the interest rate will never exceed 8.95% for loan terms 10 years or less. For loan terms of 10 years to 15 years, the interest rate will never exceed 9.95%. For loan terms over 15 years, the interest rate will never exceed 11.95% (the maximum rates for these loans). Earnest variable interest rate loans are based on a publicly available index, the one month London Interbank Offered Rate (LIBOR). Your rate will be calculated each month by adding a margin between 1.82% and 5.50% to the one month LIBOR. The rate will not increase more than once per month. Earnest rate ranges are current as of December 13, 2019, and are subject to change based on market conditions and borrower eligibility.

Auto Pay discount: If you make monthly principal and interest payments by an automatic, monthly deduction from a savings or checking account, your rate will be reduced by one quarter of one percent (0.25%) for so long as you continue to make automatic, electronic monthly payments. This benefit is suspended during periods of deferment and forbearance.

The information provided on this page is updated as of 12/13/2019. Earnest reserves the right to change, pause, or terminate product offerings at any time without notice. Earnest loans are originated by Earnest Operations LLC. California Finance Lender License 6054788. NMLS # 1204917. Earnest Operations LLC is located at 302 2nd Street, Suite 401N, San Francisco, CA 94107. Terms and Conditions apply. Visit, email us at, or call 888-601-2801 for more information on our student loan refinance product.

© 2018 Earnest LLC. All rights reserved. Earnest LLC and its subsidiaries, including Earnest Operations LLC, are not sponsored by or agencies of the United States of America.

2 Important Disclosures for SoFi.

SoFi Disclosures

  1. Student loan Refinance: Fixed rates from 3.46% APR (with AutoPay) to 7.61% APR (without AutoPay). Variable rates currently from 2.31% APR (with AutoPay) to 7.61% (without AutoPay). Interest rates on variable rate loans are capped at either 8.95% or 9.95% depending on term of loan. See APR examples and terms. Lowest variable rate of 2.31% APR assumes current 1 month LIBOR rate of 2.31% plus 0.75% margin minus 0.25% for AutoPay. If approved for a loan, the fixed or variable interest rate offered will depend on your credit history and the term of the loan and will be within the ranges of rates listed above. For the SoFi variable rate loan, the 1-month LIBOR index will adjust monthly and the loan payment will be re-amortized and may change monthly. APRs for variable rate loans may increase after origination if the LIBOR index increases. The SoFi 0.25% AutoPay interest rate reduction requires you to agree to make monthly principal and interest payments by an automatic monthly deduction from a savings or checking account. The benefit will discontinue and be lost for periods in which you do not pay by automatic deduction from a savings or checking account.

3 Important Disclosures for Figure.

Figure Disclosures

Figure’s Student Refinance Loan is a private loan. If you refinance federal loans, you forfeit certain flexible repayment options associated with those loans. If you expect to incur financial hardship that would impact your ability to repay, you should consider federal consolidation alternatives.

4 Important Disclosures for College Ave.

College Ave Disclosures

College Ave Student Loans products are made available through either Firstrust Bank, member FDIC or M.Y. Safra Bank, FSB, member FDIC. All loans are subject to individual approval and adherence to underwriting guidelines. Program restrictions, other terms, and conditions apply.

1College Ave Refi Education loans are not currently available to residents of Maine.

2All rates shown include autopay discount. The 0.25% auto-pay interest rate reduction applies as long as a valid bank account is designated for required monthly payments. Variable rates may increase after consummation.

3$5,000 is the minimum requirement to refinance. The maximum loan amount is $300,000 for those with medical, dental, pharmacy or veterinary doctorate degrees, and $150,000 for all other undergraduate or graduate degrees.

4This informational repayment example uses typical loan terms for a refi borrower with a Full Principal & Interest Repayment and a 10-year repayment term, has a $40,000 loan and a 5.5% Annual Percentage Rate (“APR”): 120 monthly payments of $434.11 while in the repayment period, for a total amount of payments of $52,092.61. Loans will never have a full principal and interest monthly payment of less than $50. Your actual rates and repayment terms may vary.

Information advertised valid as of 1/1/2020. Variable interest rates may increase after consummation.

5 Important Disclosures for Laurel Road.

Laurel Road Disclosures

Laurel Road is a brand of KeyBank National Association offering online lending products in all 50 U.S. states, Washington, D.C., and Puerto Rico. Mortgage lending is not offered in Puerto Rico. All loans are provided by KeyBank National Association.
As used throughout these Terms & Conditions, the term “Lender” refers to KeyBank National Association and its affiliates, agents, guaranty insurers, investors, assigns, and successors in interest.

This term represents the actual cost of financing to the borrower over the life of the loan expressed as a yearly rate.


There are no origination fees or prepayment penalties associated with the loan. Lender may assess a late fee if any part of a payment is not received within 15 days of the payment due date. Any late fee assessed shall not exceed 5% of the late payment or $28, whichever is less. A borrower may be charged $20 for any payment (including a check or an electronic payment) that is returned unpaid due to non-sufficient funds (NSF) or a closed account.


For bachelor’s degrees and higher, up to 100% of outstanding private and federal student loans (minimum $5,000) are eligible for refinancing. If you are refinancing greater than $300,000 in student loan debt, Lender may refinance the loans into 2 or more new loans.
For eligible Associates degrees in the healthcare field (see Eligibility & Eligible Loans section below), Lender will refinance up to $50,000 in loans for non-ParentPlus refinance loans. Note, parents who are refinancing loans taken out on behalf of a child who has obtained an associates degrees in an eligible healthcare field are not subject to the $50,000 loan maximum, refer to for more information about refinancing ParentPlus loans.


Borrower, and Co-signer if applicable, must be a U.S. Citizen or Permanent Resident with a valid I-551 card (which must show a minimum of 10 years between “Resident Since” date and “Card Expires” date or has no expiration date); state that they are of at least borrowing age in the state of residence at the time of application; and meet Lender underwriting criteria (including, for example, employment, debt-to-income, disposable income, and credit history requirements).

Graduates may refinance any unsubsidized or subsidized Federal or private student loan that was used exclusively for qualified higher education expenses (as defined in 26 USC Section 221) at an accredited U.S. undergraduate or graduate school. Any federal loans refinanced with Lender are private loans and do not have the same repayment options that federal loan program offers such as Income Based Repayment or Income Contingent Repayment.

All loans must be in grace or repayment status and cannot be in default. Borrower must have graduated or be enrolled in good standing in the final term preceding graduation from an accredited Title IV U.S. school and must be employed, or have an eligible offer of employment. Parents looking to refinance loans taken out on behalf of a child should refer to for applicable terms and conditions.

For Associates Degrees: Only associates degrees earned in one of the following are eligible for refinancing: Cardiovascular Technologist (CVT); Dental Hygiene; Diagnostic Medical Sonography; EMT/Paramedics; Nuclear Technician; Nursing; Occupational Therapy Assistant; Pharmacy Technician; Physical Therapy Assistant; Radiation Therapy; Radiologic/MRI Technologist; Respiratory Therapy; or Surgical Technologist. To refinance an Associates degree, a borrower must also either be currently enrolled and in the final term of an associate degree program at a Title IV eligible school with an offer of employment in the same field in which they will receive an eligible associate degree OR have graduated from a school that is Title IV eligible with an eligible associate and have been employed, for a minimum of 12 months, in the same field of study of the associate degree earned.


The interest rate you are offered will depend on your credit profile, income, and total debt payments as well as your choice of fixed or variable and choice of term. For applicants who are currently medical or dental residents, your rate offer may also vary depending on whether you have secured employment for after residency.


The repayment of any refinanced student loan will commence (1) immediately after disbursement by us, or (2) after any grace or in-school deferment period, existing prior to refinancing and/or consolidation with us, has expired.


After loan disbursement, if a borrower documents a qualifying economic hardship, we may agree in our discretion to allow for full or partial forbearance of payments for one or more 3-month time periods (not to exceed 12 months in the aggregate during the term of your loan), provided that we receive acceptable documentation (including updating documentation) of the nature and expected duration of the borrower’s economic hardship.

We may agree under certain circumstances to allow a borrower to make $100/month payments for a period of time immediately after loan disbursement if the borrower is employed full-time as an intern, resident, or similar postgraduate trainee at the time of loan disbursement. These payments may not be enough to cover all of the interest that accrues on the loan. Unpaid accrued interest will be added to your loan and monthly payments of principal and interest will begin when the post-graduate training program ends.

We may agree under certain circumstances to allow postponement (deferral) of monthly payments of principal and interest for a period of time immediately following loan disbursement (not to exceed 6 months after the borrower’s graduation with an eligible degree), if the borrower is an eligible student in the borrower’s final term at the time of loan disbursement or graduated less than 6 months before loan disbursement, and has accepted an offer of (or has already begun) full-time employment.

If Lender agrees (in its sole discretion) to postpone or reduce any monthly payment(s) for a period of time, interest on the loan will continue to accrue for each day principal is owed. Although the borrower might not be required to make payments during such a period, the borrower may continue to make payments during such a period. Making payments, or paying some of the interest, will reduce the total amount that will be required to be paid over the life of the loan. Interest not paid during any period when Lender has agreed to postpone or reduce any monthly payment will be added to the principal balance through capitalization (compounding) at the end of such a period, one month before the borrower is required to resume making regular monthly payments.


This information is current as of November 8, 2019 and is subject to change.

6 Important Disclosures for Splash Financial.

Splash Financial Disclosures

Terms and Conditions apply. Splash reserves the right to modify or discontinue products and benefits at any time without notice. Rates and terms are also subject to change at any time without notice. Offers are subject to credit approval. To qualify, a borrower must be a U.S. citizen or permanent resident in an eligible state and meet applicable underwriting requirements. Not all borrowers receive the lowest rate. Lowest rates are reserved for the highest qualified borrowers.

7 Important Disclosures for CommonBond.

CommonBond Disclosures

Offered terms are subject to change. Loans are offered by CommonBond Lending, LLC (NMLS # 1175900). If you are approved for a loan, the interest rate offered will depend on your credit profile, your application, the loan term selected and will be within the ranges of rates shown. All Annual Percentage Rates (APRs) displayed assume borrowers enroll in auto pay and account for the 0.25% reduction in interest rate. All variable rates are based on a 1-month LIBOR assumption of 1.76% effective November 10, 2019.

8 Important Disclosures for LendKey.

LendKey Disclosures

Refinancing via is only available for applicants with qualified private education loans from an eligible institution. Loans that were used for exam preparation classes, including, but not limited to, loans for LSAT, MCAT, GMAT, and GRE preparation, are not eligible for refinancing with a lender via If you currently have any of these exam preparation loans, you should not include them in an application to refinance your student loans on this website. Applicants must be either U.S. citizens or Permanent Residents in an eligible state to qualify for a loan. Certain membership requirements (including the opening of a share account and any applicable association fees in connection with membership) may apply in the event that an applicant wishes to accept a loan offer from a credit union lender. Lenders participating on reserve the right to modify or discontinue the products, terms, and benefits offered on this website at any time without notice. LendKey Technologies, Inc. is not affiliated with, nor does it  endorse,  any educational institution.

Subject to floor rate and may require the automatic payments be made from a checking or savings account with the lender. The rate reduction will be removed and the rate will be increased by 0.25% upon any cancellation or failed collection attempt of the automatic payment and will be suspended during any period of deferment or forbearance. As a result, during the forbearance or suspension period, and/or if the automatic payment is canceled, any increase will take the form of higher payments. The lowest advertised variable APR is only available for loan terms of  5 years and is reserved for applicants with FICO scores of at least 810.

As of 12/019/2019 student loan refinancing rates range from 1.90% to 8.59% Variable APR with AutoPay and 3.49% to 7.75% Fixed APR with AutoPay.

1.99% – 6.89%1Undergrad
& Graduate

Visit Earnest

2.31% – 7.36%2Undergrad
& Graduate

Visit SoFi

2.06% – 6.81%3Undergrad
& Graduate

Visit Figure

2.62% – 6.12%4Undergrad
& Graduate

Visit College Ave

2.29% – 6.65%5Undergrad
& Graduate

Visit Laurel Road

1.99% – 7.06%6Undergrad
& Graduate

Visit Splash

1.81% – 6.29%7Undergrad
& Graduate

Visit CommonBond

1.90% – 8.59%8Undergrad
& Graduate

Visit Lendkey

Our team at Student Loan Hero works hard to find and recommend products and services that we believe are of high quality. We sometimes earn a sales commission or advertising fee when recommending various products and services to you. Similar to when you are being sold any product or service, be sure to read the fine print to help you understand what you are buying. Be sure to consult with a licensed professional if you have any concerns. Student Loan Hero is not a lender or investment advisor. We are not involved in the loan approval or investment process, nor do we make credit or investment related decisions. The rates and terms listed on our website are estimates and are subject to change at any time.

Published in Big Money Decisions, Budgeting & Expenses, Make More Money, Side Hustles, Taxes