How To Start The Right Online Business To Match Your Personality

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Part of the series “Leading Entrepreneurial Success Today”

How many times have we heard that approximately half of all small businesses fail by the fifth year mark? There have been hundreds of articles written and entrepreneurial training programs developed to address this phenomenon, but one factor that isn’t discussed as frequently as it should be revolves around two core questions:

1)  Is the business you’ve started a true match to your personality?

2)  Will this business model be personally rewarding and fit the way you want to work, so you can invest the necessary time, energy and money to sustain and grow this business over the long haul? Today In: Leadership

To explore more about these critical questions, I caught up recently with Jill Stanton, the co-founder with her husband Josh of Screw The Nine To Five—a slice of the web where the Stantons work to transform unsatisfied employees into successful entrepreneurs. Screw The Nine To Five is a destination for up-and-coming online entrepreneurs to obtain the information and inspiration they need to start and growth their business. According to Jill Stanton, Screw The Nine To Five has generated over $1.7 million since it became a full-time focus for Josh and Jill in 2014.

Stanton believes that the high rate of failure of small businesses is in great part due to the fact that most people pursue the first business model they come across (which isn’t always the best fit for their strengths and lifestyle goals) and therefore end up burnt out, unaligned with what they’ve built and sadly, find themselves back at square one once they realize they have to start all over again.


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To help people bypass this pitfall, Jill and Josh have developed a simple strategy for ensuring new entrepreneurs start the right business straight out of the gate, ultimately saving people an enormous amount of time, energy and money. 

Here’s what Jill Stanton shares:

Kathy Caprino: Jill, you and Josh have been running online businesses together for over seven years and I heard you got started with a skincare blog. Not exactly the kind of business you would expect to make money. What made you choose that as your first business together?

Jill Stanton: I know, it sounds totally random. However, there was a method to our madness.

Back in 2012 Josh had just ended his business partnership and I was quickly starting to feel burnt out and disenchanted with my social media management business.

At the time we were living in Toronto and we both knew we didn’t want to suffer through the winter, so we decided to start a business together that would allow us an abundance of time and location freedom.

Since Josh already had some experience with running online businesses, we decided to jump in with both feet.

At that point in our lives we both didn’t really have a “passion” (other than building and growing this business of ours), so we did some basic research and decided to start a skincare blog. Why skincare? Because we knew it was a booming industry and millions of people were already purchasing skincare products online.

It seemed like a no-brainer to us so we dove in head first and quickly got a crash course in content marketing, traffic generation and what it looks like to run a business with your significant other.

Caprino: How did you make money from a skincare blog?

Stanton: At the time blogging was huge and fortunately, Josh had spent a couple years learning about SEO and how to use it rank on Google to attract free, targeted traffic to a website.

We found products that people were already searching Google for (using a process called Keyword Research), tested them out on ourselves and then started writing in-depth product reviews around those products.

After only four months of creating consistent content for our website (through a mix of product reviews and DIY skincare recipes), our little website hit the coveted $1,000 a month mark. We did this by leveraging the affiliate marketing revenue model, which at its core breaks down to this: You get paid commissions for referring leads and customers to other brands and product owners.

In other words, we served as the “middle man” who connected our audience to the skincare products we used, liked and believed in. It was a simple business model that wasn’t timezone dependent, didn’t require any fulfillment on our end and simply relied on our ability to create top-notch content.

This is yet another reason why we love affiliate marketing–because almost anyone can do it.

Caprino: You mentioned in our conversation that you feel having a passion isn’t a core requirement for starting a business? If so, what is?

Stanton: It sounds counter-intuitive, and to clarify, we do believe that you need some sort of passion for what you’re doing, otherwise when things get hard it will be easy to walk away.

However, we don’t believe you need to have a passion for the specific niche you’re in. Instead, here are two critical considerations we believe are required for starting a business online:

  1. There needs to be a market of people who are buying products in the niche you want to enter.
  2. Your business model needs to be a match for your personality

Think of it this way: If you aren’t taking into account your specific strengths and weaknesses and the goals you have for your specific lifestyle, you may find yourself feeling trapped inside a business that doesn’t align with your core values. We’ve seen this happen in our own business and to so many of our members inside our communities, and it’s completely avoidable.

All you have to do is put some conscious thought into the type of business you believe serves you, your personality and your lifestyle goals best so that you can show up and serve the people you’re meant to impact.

Caprino: How do you suggest that someone figure out the best type of business that suits their personality if they’ve never launched one before?

Stanton: This is easier than people may think and there are a few personality tests online that can help you get clear on where you shine and what your weaknesses are.

Our three favorite tests for this are The Enneagram Test (I’m an 8 and Josh is a 5), The Fascination Test (I’m “The People’s Champion” and Josh is “The Diplomat”) or The Myers Briggs profile (I’m an ESFJ and Josh is an INTP).

What is so useful about these tests is they allow you to get a deeper understanding of your personality so you can choose a business model that compliments your strengths and avoid the ones that will leave you feeling unaligned and resentful.

For example, say you are a charismatic extrovert who currently works in sales. If you decided to start a software business, you would likely find yourself feeling bored, overwhelmed and isolated. Whereas if you were to create a personal brand where you taught what you knew (ie. sales) through a business model such as coaching or even creating online courses, your business may likely do well because you are playing to your strengths and using them to create a big impact (and income).

Caprino: Aside from matching the right personality to the right business, is there anything else you’d suggest considering?

Stanton: Yes. This boils down to getting clear on your values and how you want to live your life outside of your business.

Think about it: You can have an undying passion for your business, but if you aren’t taking time to nurture your other interests or the people closest to you, all the money in the world isn’t going to matter because you will be left feeling empty.

Instead, get clear on the things, people or hobbies that bring you joy outside of your business so you can work them into your schedule. For Josh and me, one of our biggest values is freedom. To us, that means both time and location freedom.

If we were to create a business that requires us to be on a specific timezone 24/7/365 we would show up in a poor way and our business (and therefore lifestyle, relationship and finances) would suffer.

This is why we always encourage up-and-coming entrepreneurs to sit down and do the deep work at the start so they don’t find themselves a year or two into their business feeling like they have a job and sabotaging their success…and no one wants that.

Caprino: It sounds like you’ve cracked “the secret,” but we all know succeeding in business isn’t really that simple, right? What other suggestions do you offer new entrepreneurs to become more successful?

Stanton: Absolutely. We’ve had to learn how to run a business online the hard way by doing things that don’t work so we can figure out what does. We’ve battled it out in the areas of operations, hiring and firing team members, learning how to manage money and building the right kind of traffic and attention to our brand.

It wasn’t easy, but it most certainly has been worth it and it’s why we are so driven to help unsatisfied employees and up-and-coming entrepreneurs get clear on which business is right for them so we can give them the tools and skills they need to bring it to life.

It’s our version of the “fast track” (if there ever was one) to success and it’s how we help transform unsatisfied employees into dangerously-successful entrepreneurs in a way that doesn’t sacrifice the things that matter most to them.

Here are our top suggested steps for going from building revenue as effectively as possible in the first year of your new business:

Step 1: Identify the type of online business that best matches your personality and the lifestyle goals you have

This can be anything from e-commerce (i.e. selling physical products online) to digital products (i.e. creating and selling online courses or membership sites) to coaching and consulting (either one-on-one or inside a group program) or affiliate marketing (i.e. getting paid a commission for any leads and customers you send to a merchant).

The key here is to examine the different options you have and choose the business model you believe best aligns with your strengths.

Step 2: Invest in yourself and focus on building the skills necessary

Enroll in training courses designed to accelerate your journey and teach you the strategies you need to get your business off the ground and profitable. 

Do you have to enroll in courses? No, but, we’re big believers in learning from experts who are where you want to be in order to accelerate your results.

Step 3: Choose a profitable niche that you know will generate revenue

How do you know if your niche is profitable? Look to see who is selling products in that market, what they are selling and if there is a high demand for it and then use that information as inspiration to dream up your own offers so you can get started generating revenue.

Step 4: Build your audience and email list

If there is one thing that will help you make money fast online, it’s getting in front of the people who are aligned with what you have to say and sell and giving them an opportunity to connect with you through a free offer that helps you build your email list.

To do that, identify key podcasts, video interview shows, magazines and online publications that are looking for content and contributors and then pitch relevant topics that lend massive value to their audience.

Not only will these features and interviews give you and your business credibility, but it will also help you position yourself as a go-to expert in your space, ultimately allowing you to make money faster than sitting around and hoping the right people find you.



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