3 Proven Side Hustles for Startup Founders (Generate Cash Fast)

by Accessory To Success June 06, 2021

3 Proven Side Hustles for Startup Founders (Generate Cash Fast)

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Side Hustle Is Necessary

If your dream is to start your own business and become an entrepreneur, you may want to think about keeping yourself afloat financially while waiting for your business to hit the big time. Your dream may be financial independence or to dominate an industry globally, but you will need a way of supporting yourself while your startup is becoming established. A side hustle is a great option for you when you want to keep money coming in while you are waiting for your startup to become profitable.

If you are inspired by an entrepreneur, you should research their first job to become inspired every day. The rise of Jeff Bezos from selling books online from his garage is a dream for many of you who aspire to create a global business. What is less well known is the time Bezos spent learning about automation in a McDonald's restaurant. David Geffen, the entertainment entrepreneur, started his career as a mailroom clerk at the William Morris Agency in Hollywood. Geffen was able to learn about the entertainment industry while earning money and making the contacts that allowed him to establish his first record company.


Set a Timeframe for your Goal

Whether you are young and want to establish your financial freedom early in your career or have an idea you have been sitting on for many years, there are steps to follow when you are looking to become an entrepreneur. Your belief in the business idea you have created may not be shared by your potential customers, leaving you in a difficult position. Read Perfectly Confident for a more realistic mindset.

The eight-time Major League Baseball batting champion, Tony Gwynn, was drafted in the third round of the 1981 MLB draft by the San Diego Padres. For Gwynn, the success he had achieved at San Diego State College was a stepping stone on a much longer journey. The Padres sent their recruit to the minor leagues to gain experience leaving Gwynn to set himself a target for making his way to the big leagues in three years. Despite his obvious talent, Tony Gwynn was willing to retire from baseball if he failed to achieve his dream within a specific timeframe.

As an entrepreneur, you should be thinking in a similar way to Tony Gwynn, because you will need to stop the losses you will see when building your business. Starting a business costs money and you need to do two things if it is going to succeed: generate cash & make a profit. More on that in the book The Great Game of Business.

Until your business is driving revenue, a side hustle would help you pay your bills while your startup is getting off the ground. The best side hustles allow you the time to work on your passion project and allow you to learn about how a successful business operates. The career of Jeff Bezos was affected by the way he saw McDonald's working during his time working at the fast-food chain. Another great book on this is kind rise story is about the founder of Home Depot in his book I Love Capitalism.


What to Look for in a Side Hustle?

Before you decide to accept a job or to invest in a small business, you need to consider how the role will affect your life. The first question you need to ask yourself is, will your side hustle leave you with time to chase your entrepreneurial dream? A good side hustle will allow you the time to work on your long-term business goals while bringing in an income.

As an entrepreneur, you should be looking for income that gives you the time to build your startup. Driving enough revenue to support yourself is not going to come passively. That said, our suggestion is to be thinking of what your side hustle is teaching you about the business sector. If you can generate cash and learn about business that is a perfect situation.


Some Side-Hustles to Consider

Own a Vending Machine

When you are looking for a side hustle to generate cash and learn about business, a vending machine operation is a great option to explore. You can look at a vending machine as a nickles and dimes business, but your profit levels will be high with this option if you are willing to learn about your customers.

There are many important subjects you can cover when owning a vending machine, including:

  • Profit and Loss
  • Cashflow
  • Insurance
  • Inventory Management
  • Customer Service

The first part of owning a vending machine that makes it an excellent side-hustle is the low startup and maintenance costs you face. If you are looking for a way of bringing in extra money, a vending machine can be purchased for less than $5,000 in a brand new condition. If you choose to seek out a used one, you can purchase a refurbished machine for half that.

If you are looking for the cheapest available option, you could look for a used machine without any certification, although this is a dangerous option to take. A used machine could set you back more money to repair and keep in good working order.

Choosing a site can begin before you buy a machine because you will want to discuss your options with local business owners and schools. Many of these organizations will look to include your vending machine at their site to provide employees and students with snack options to keep them happy throughout the day.

The low overheads of a vending machine can be lower when you get the chance to position your machine in a location without the need to pay any rent to the owner. By finding a friendly property owner, who does not charge you rent, you will move towards profit faster.

One of the most important lessons you need to learn as an entrepreneur is a difference between cashflow and profit. A vending machine is a good starting point for understanding profit and cashflow, which will serve you well in the future. Your vending machine may have a high level of cashflow each week, but you will not make a profit until you have paid off your overheads, including the purchase of your machine. If you are paying rent for the space your machine occupies, this cuts into the potential profit you will make and the time when your vending machine will bring you profits. The best book for this is Profit First.

If you are looking for a side hustle that gives you regular payments and very little customer interaction, a vending machine is a good choice. Let's say your vending machine does not give out change or a packet of chips is stuck, you will get a call from a customer to ask for their money back. This is an opportunity to learn how to manage customers. You can systematize your responses and even learn to work with virtual assistants. Its very important to have an idea about how you want to handle customers. Try reading the book Give Em The Pickle.

One of the most important lessons you will learn when you choose to operate a vending machine as your side hustle is to listen to your customers. To operate a profitable vending machine, you need to provide your customers with the snacks and drinks they want each day. You should quickly notice the items that sell out quickly and those that are left behind each day, which is known as supply and demand. Boosting the number of products your customers enjoy most and limiting those that are not as popular is a lesson that will be important for you to learn as an entrepreneur. More on the importance of customer feedback can be found in a book for entrepreneurs: Ready Fire Aim.


Become a Personal Trainer

As an entrepreneur working towards building your brand, you need to have the time and flexibility to work on your business each week. Few side hustles are offering flexibility for your time like that more than becoming a personal trainer. The majority of your clients as a personal trainer will want your help for short periods of time each week: 30 minutes to an hour.


The majority of your clients will want to obtain your services as a trainer during the mornings and evenings, leaving the majority of your days free to work on the project you are passionate about. Perfect!

Some gyms require a certification in personal training and this can be achieved with an online course. Others don't. Just get the certification though, you'll make the couple hundred dollars back very fast.

One of the benefits of working as a personal trainer is the number of different people you will meet in this role. If you want to make contacts for the future of your entrepreneurial career, you will work with a range of different people from all walks of life. If you are working towards building a tech startup and begin working with a financial expert, you can discuss your financing options with your client as you work out.

When you choose to work as a personal trainer, you are working a side hustle that brings you very little stress. As a personal trainer, you do not need to rent a space to work alongside your clients. Your skills will be utilized in the homes of your clients and parks around your home area. And since this is a time for money exchange you get the cash quickly.

Unlike other options, you will not need to think about the job you are doing outside of the hours you spend working as a personal trainer. The ability to leave this job behind at the end of each session will keep your mind free to work on your entrepreneurial project each day.

Alongside your ability to concentrate on the work you are doing as an entrepreneur, you will learn about scheduling clients and organizing your time and equipment each day. If there is one aspect to starting a business every entrepreneur needs it is this kind of discipline. For more on this read the amazing book Discipline Equals Freedom.


Become a Freelance Writer

Another side hustle that gives you many benefits is that of a freelance writer. You may not have the freedom throughout the day of a personal trainer or the operational education and potential passive income of a vending machine owner, but you will learn about different subjects. Freelance writing sites and communities can be found all over the Internet, with members of every industry looking for work or help.

Freelance writers with expertise in specific areas of the industry are always in demand. If you are building a startup in an industry, you should be an expert in your chosen area of entrepreneurship. Being classed as an expert in your chosen field will lead to members of your industry looking for you to create articles and increase the number of views of their websites and social media posts. And more importantly, improve your chances of making good decisions about how to run and grow your own business.

You should consider freelance writing to be more intensive and time-consuming than the other side-hustles already discussed. But you can network with clients and make contacts in an industry you hope to break into as an entrepreneur. Once you are in the rhythm of working as a writer you will find the time it takes to complete an article is very short, with your earning power limited only by the time you are willing to commit, all while your knowledge in a particular subject compounds.


Social Media Expert

When you are hoping to build a career as an entrepreneur, you will be spending a lot of time on social media platforms researching your chosen sector. You will quickly find yourself understanding the ins and outs of achieving success on social media. The ability to manage social media accounts can be turned into a side-hustle bringing in $500 to $3,000 each month.

The usual practice for a social media manager is to make at least one post per day per platform, per client. If you work with four companies to create this side-hustle that should generate enough cash to keep you afloat. If we assume one hour per client, it should give you the time you need to work on your entrepreneurial project.

As this is not a direct time for money exchange this side hustle gives you the chance to make money with less time spent working. The benefits of working as a social media manager are easy to see. Your work would bring you into contact with clients from different sectors and companies. It would allow you to learn how to present yourself correctly online when you are working on your own business.

Three Steps To Succeed:

  1. Use the contact us section of a website with a weak social following telling them you can grow their following.
  2. Win the businesses (you need to know how to close, yes)
  3. Hire a freelancer from Fiverr or Upwork to do all the work for you.
  4. Your role will be to manage the client relationship and freelancer.

Side-Hustles you Should Avoid

The choice of side hustle for entrepreneurs can be a tough one when you are looking for a way of keeping yourself afloat financially while you work on your startup. There are some excellent opportunities available to you, but the wrong choice can limit the time you spend as an entrepreneur.

Side hustles you should avoid include:

  • Uber/Lyft
  • Door Dash
  • Cold Calling
  • Bartender
  • Amazon reseller

The consistent nature of the jobs you should avoid is the time they take out of each day. When you want to focus on a career as an entrepreneur, you should look for side hustles that will not limit the time you have available for your passion.

A side hustle should give you a high level of financial return for the number of hours you are willing to invest OR an increase in your education while you gat paid.

The ideal side hustle provides you with a high financial return for little effort when you focus your energy on them for a short period of time. No matter what stage your entrepreneurial project is at, you will need to pay your bills while establishing a startup you are proud of. By choosing a side hustle from our list, you will be able to focus your energy on taking control of your career as an entrepreneur.

Accessory To Success
Accessory To Success



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