How to Start an Online Business, Move to Thailand and Earn $500K a Year: Interview with Jill from Screw The Nine to Five

This is an interview-style post with Jill Stanton from ScrewTheNinetoFive.

Hey Jill. Tell us a bit about yourself and what you do.

I’m one half of (my husband Josh is the other half) and we help transform unsatisfied employees into successful entrepreneurs by giving them the inspiration, skills and resources they need to grow their online business so they can work whenever they want from wherever they want!

What was your first online business and how did it work out?

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Short answer? Not that well! LOL 

In all seriousness though, my first attempt at an online business was actually an online TV show I created and co-produced with a partner called TwentySomething TV. 

Basically, it was an online show for women in their 20’s that covered all things relationships, health and career. 

The only drawback was I started it in 2006 when online TV shows weren’t really a thing…which meant we had trouble attracting sponsors or even monetizing it at all. 

2.5 years after we started (and over 2 million views), we aired our last episode and went our separate ways which eventually led me to start my first profitable online business which was a social media management service in the hospitality industry. 

Finally, after almost 2 years of running that, I fired my clients and started my first business with Josh — a skincare affiliate site. 

I know. So random! But it brought us to where we are now and for that I’m forever grateful for the sometimes messy and always evolving journey. 

Read also: How to Make $50000 a Year from Your Blog

What does one need to quit their job and relocate to a place like Thailand?

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The guts to do it!

That’s pretty much it. 

I mean, there are more logistics that go into the process (which I’ll quickly break down), but it ultimately comes down to this: Do you WANT to figure out a way to quit your job and make it happen? 

If you’re nodding your head “yes” at the screen then you’ll take the actions to make it happen. 

So, what are the tangible things you need

Two things: 

An Audience

Here’s a simple truth: If you want to build a business online, you need to build an audience of people who are aligned and resonate with what you have to say and sell. 

And honestly, when you have an audience (or attention to your brand in general) everything becomes easier!

Which brings me to the second thing…

An Offer 

If you want to be able to quit your job, build a business online and work from anywhere you want, then you need something to sell. 

This can be anything from a done-for-you service, coaching, consulting, a course, a membership site, a physical product to sell, or hell, promoting someone else’s product(s) like we do on ScrewTheNineToFive!

The point is there is no shortage of opportunities to make money online. 

It simply comes down to your desire to take action and make it happen. 

Read also: Want to Live The Travel Life: Here’s Where to Start

How was ScrewTheNinetoFive born?

How Guest Blogging Will Grow Your Business

This is kind of a funny story because we never started ScrewTheNineToFive with the intention of turning it into a business. 

You see, at the time Josh and I were running an affiliate marketing business with sites in all different niches (from skincare to beauty to weight loss to personal hygiene to supplements). 

And at the time we were getting a ton of questions from friends and family on how we were able to travel so much if we didn’t have “a real job”. 

(Sound familiar?) 

So we wanted a way to share our travels with them (as we were about to move to Thailand) and explain what we were doing and how we were doing it. 

From there, word started to spread and we had people reaching out and asking us if we offered coaching services. 

And from there it all started to snowball!

Fast-forward to today and we’re going into our sixth year with ScrewTheNineToFive and are even more hell-bent on helping transform unsatisfied employees into happy, fulfilled and successful entrepreneurs!

Read also: How This Girl Quit Her Job and Started Earning $15K/Month from Her Blog

What turned it from a site sharing your journey into an online community inspiring and educating people?

Truthfully, we weren’t really enjoying the time or energy commitment of coaching and so we started looking for ways to create more leverage and help more people.

That then evolved from ScrewTheNineToFive into an online course which then turned into our monthly membership community, Screw U. 

And here is where the story takes a bit of an interesting turn… 

About 3 months before doing this interview we sat in front of our members at our members-only live event in Vancouver, Canada (Screw U Live) and told them that after 4 years of having the community we were closing the doors to it as of December 31st. 

It’s been such a fulfilling journey having this community and getting the chance to impact and serve these up and coming entrepreneurs.

However, it’s time for us to close this chapter in our journey to make way for the next one which is dedicated to making ScrewTheNineToFive the #1 destination for online entrepreneurs looking for high-impact free content that helps them get results in their business. 

What’s your favorite website monetization method and why?

For us, it’s affiliate marketing!


Because we love connecting our audience with other entrepreneurs creating rad educational experiences in the online business world!

We also love the fact that this revenue model allows us to focus 90% of our time creating the best free content in our space and spreading the word on the mission that is ScrewTheNineToFive! 

We also relish in the fact that this monetization method allows us to go all-in on creating engagement, impactful free bonus experiences for anyone in our audience who chooses to invest in a product or program through our affiliate link. 

Read also: 4 Most Profitable Blog Monetization Methods

What helped you increase your income?

We’ve done a few things over the years that have helped us achieve the success we have. But I’d say the biggest one (that has had a direct and staggering impact on revenue) has been creating purposeful free content and amplifying it with Facebook Ads for the different promotions we do. 

Here’s how we do it…

Anytime we are looking to promote something, we follow these 7 steps: 

1. Brainstorm  

You likely already know what it is you want to sell or promote. So in this step what you’re doing is brainstorming 4-6 weeks of pre-launch content you can create for your audience to build anticipation around what it is you’re offering. 

To do this, pull out a piece of paper (or, you know, open a Google Doc) and brain dump 10-15 micro topics that you can create free content around (ie. Facebook Lives, podcast episodes, blogposts, videos etc..) AND are related to your offer.

Think of these topics as touch points for you to serve your audience, warm them up and build anticipation for what is coming. 

The key thing to ensure in this step is that the content you are going to be releasing is congruent with your offer. 

2. Cull

In this stage you are going to go back through your topic list and cull it down to 4-6 topics that you can create high-impact free content around and release once a week for at least 4 weeks. 

3. Plan  

Next up? 

The planning stage!

Now that you’ve identified the 4-6 best topics you want to cover, it’s time to plan out what you’re going to cover in each piece of content so you stay on track and deliver as much value as possible. 

Don’t overthink this stage, simply list out talking points you can use to either riff on (if you’re doing it on Facebook Live) or expand on in a blogpost, podcast or video. 

4. Schedule 

From there, we start assigning dates for when each piece of content goes live on ScrewTheNineToFive or another platform.

Why is this such a big piece of the plan? 

Because if you don’t assign due dates you will push it back, things will get overlooked and excuses will pop up as to why you can just “do it later”. 

Want to avoid that from derailing your promotion? 

Add due dates, schedule it into your calendar and don’t mess with it. 

5. Create 

Okay, so you’ve brainstormed topics, culled them down, planned them out and scheduled them into your calendar…what’s next? 

Create each piece of content so you don’t fall into the last minute trap where you scramble to get everything done in the final few days before it goes live. 


Because when you operate from a last minute mentality, you add in a level of unnecessary stress and create lacklustre work. 

Harsh, but true. 

Now, almost every piece of content (outside of live broadcasts) can be created well ahead of your promotion or launch!

The beauty of that is you now have ample time to show up and be present during your actual promotion so that you can connect with your audience, serve them even more and close like a mofo!

6. Amplify

This is my favourite piece of this whole plan. 


Because this is where you get to amplify the heck out of your content so that you can get it in front of the people who need it most and set the stage for your upcoming offer. 

How do we do this? 

Well, of course you can use your email list and social media platforms, but the real magic happens when you layer in some paid traffic

And here is why I love amplifying pre-launch content: Because it allows you to serve your new AND existing audience in such a huge way, without asking for anything in return. 

Another bonus? 

You can get hella targeted with paid traffic and make sure that anyone who is seeing your free content is perfectly aligned with what you have to say and sell!

7. Close

Alright, once you’ve created, published and amplified your free content to both a warm and cold audience, now you get to double down, make your offer and retarget anyone who has interacted with your content, lead magnet or offer and go for the close!

How do we do this? 

Ads, of course!

But not just any old ads. 

Ads that communicate the transformation someone will get when they invest in your offer. 

Ads that highlight your existing customers and the results they’ve seen from working with you. 

Ads that overcome objections. 

Ads that communicate urgency. 

And ads that move people to make a decision to invest in your offer or pass on it. 

Forgo this piece of the puzzle and you may watch your conversions and sales fizzle. 

*thumbs down*

Read also: How to Make $1000/Month with Ads on Your Blog

Would you advise anyone to start a business with their partner and why?

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Of course! I have nothing but amazing things to say when it comes to working with your partner!

Now, obviously, there will be some growing pains, a few complications and a whole lot of honest conversations you will have to have in order to figure each other out and how you best excel in the business. 

However, there is nothing better than building a dream (and achieving it!) with the person you love the most!

The thing that has worked best for Josh and I is to identify our individual strengths in the business, own that side of the business and trust that the other has their side. 

That way you aren’t constantly trying to battle over who is doing what, who is right, who is wrong and if they are doing it “right”…because trust me, that NEVER works! *wink*

Instead, stay committed to honest, transparent conversations and you will figure out your flow together

What are the characteristics of a lifestyle entrepreneur?

Ohhh this is a good one because there are so many!

I think the biggest ones are: 

  1. Resilience
  2. Patience
  3. Consistency
  4. A tolerance for risk and the unknown 
  5. A strong inner game 

I mean, sure, there are likely more, but these 5 characteristics or traits are always the most common ones I notice amongst the most successful lifestyle entrepreneurs!

Read also: What is a Lifestyle Business and 3 Solid Reasons to Start One

What’s next for you and Josh?

We are hell-bent on turning ScrewTheNineToFive into the #1 destination for online entrepreneurs, which means going into pure content creation mode for the next few years!

We are increasing our podcast up to 3 episodes a week in the new year, plus releasing a new high-impact blog post each week, rolling out a pitch-free 5 day challenge (the Employee To Entrepreneur Challenge) and a couple of hella-fun and engaging free popup FB Groups throughout the year!

I don’t know if it’s just me, but I can’t help but feel like next year is gonna be one of those years that oozes unstoppable momentum and feels wildly exciting!

Jill and Josh from ScrewTheNinetoFive share how they turned their site into a real business, built a community and grew their income to $500K: #screwtheninetofive #howtomake500k #makemoneyblogging #sidehustleideas #sixfigureincome #moneymakingideas #startanonlinebusiness #makemoney