What it Takes to Build a FREEDOM FIRST Business with Rachel Kelly

If you’ve been following me for some time, you’ll know that a freedom-based business is my favorite thing to talk about. A big value that we have in the Chillpreneur company is freedom. Having the freedom to be able to travel the world, pursue hobbies, spend time with loved ones, and not selling your soul to the idea that you have to hustle and grind in order to be really successful.

Whatever it means to you, whatever your freedom-based business looks like, it’s the freedom to have a choice about how to spend your time.  It’s not just luxurious travel, it’s not just luxurious lifestyles. It’s actually having the freedom to enjoy your life while simultaneously growing and scaling a business.

So let’s dive into what a freedom-based business really looks like. 

Is having a freedom-first business for everyone? No. Because you need to have a strong drive and a strong value for the need for freedom. 

[00:07:00] WHO IS RACHEL?

Rachel has had a seriously long career in entrepreneurship. She started in 2012 when she was 16 because she decided to launch an international clothing brand.

“At the time, I had, zero experience, like did not know anything about the industry, did not know anything about the moving parts. Just knew that it was something that inspired me in an industry that I really wanted to be a part of. And I was like, fuck it, I’m gonna do it.” 

She taught herself pretty much every aspect of moving the business forward – from coding websites in her little tiny one-bedroom to learning how to build a loyal audience and customer base to outsourcing to importing. All the sort of moving parts of the business. 

“That’s where things really, really blew up for me. I was so young. All my friends were going out and living their life and partying, and I was at home doing all-nighters in between my job to work and grow my business.” 

Within six months, she had built an audience of 13,000 people, had been published in two massive magazines [00:08:30] in Australia, had really good contracts with a lot of stylists and photographers, and was receiving invitations to meet with people around the world to stock her stuff. 

“But there came a point where I realized I was so in over my head. I got this really great success quickly, but it turned into a huge mental [00:09:00] health crisis. I had a massive breakdown with the weight of everything. The responsibility. The imposter syndrome. And that fear of failure.” 

So, in 2014, she made the really hard decision to actually close that business down to focus on her mental health.

Her second business was focused on helping other business owners to scale and grow their businesses. 

“I wanted to find a way to help other business owners not feel alone. It’s really, really hard when you’re a solopreneur. You’re wearing every single hat, and you also have no fricking [00:10:00] idea what you’re meant to be doing.” 

Having done the hard yards to set herself up for success when it came to her mindset, her social media & marketing agency quickly grew to six figures.

“And then there was a point, I think about a year and a half, two years into that where I just, everyone was asking me for [00:11:00] business advice and consulting advice. And that’s where Rachel Kelly International was born. So yeah, it’s been a while, and that is now almost eight years ago.”


Experience and failure. Honestly, that is where I’ve learned the most. Through all my successes that I’ve had in my career, it’s always been my biggest failures that have been the biggest teaching moments for me. 

It doesn’t always have to be this traditional methodology of reading all the books, doing all the courses. Experience-based learning is really powerful, but to get the most out of those experiences, you need to pay [00:13:00] attention, analyze, and strategize. 


A lot of other people who go down the path of speaking about a freedom-based business speak to it from the perspective of passive strategies. But, for so many people, this definition feels really stifling. 

There is alot of misconception about what it really is. 

But a freedom first business is a business that can operate at any time from anywhere in the world without you having to sacrifice your time, your values, your health, or your sanity to actually have that. Yeah. So it’s a business that can generate sales and grow at any time. So while you travel, while you [00:15:30] sleep, or even while you binge watch reality TV with an amaretto sour in hand. 


A freedom-based business has many different moving elements and moving parts to it. A huge part of it is obviously your visibility and taking up your online real estate. Building an audience, getting in front of as many eyes as possible and really building that brand awareness. That’s where having a really great content strategy comes into it as well. 

But in more of the mechanics side of things, it’s having [00:17:00] scalable offers. So having an offer that’s not limited to a time or how many people you could have or when it could be purchased or enrolled into. So something that can have enrollments or sales made every single hour of the day, which is where passive products come into it. So online classes, online courses, masterclasses, workshops, anything like that that can kind of run on autopilot all the time, that doesn’t involve you trading your time for it. 

A huge part of it is team. I don’t know one person that has a freedom first business or freedom based business that is solo. 

“I have a very small team, but when I travel, these are the guys that hold down the fort for me while I am away. So they’re the ones are checking the emails, responding to inquiries, making sure all the tech’s working, making sure that everything.” 

You need to learn to like release the need to wear all of the hats.


Is having a freedom first business or freedom based business is for everyone? No. Because you need to have a strong drive and a strong value for the need for freedom. 

“I don’t think that any two people have the same definition of success. Some people, like me, wanna drink cocktails and be paid and peaceful.” 

Is it achievable for anyone that does have that value? Absolutely. It does take time to understand all the different aspects of it and get everything up and running. It won’t happen within a couple of months, but dedicate yourself for a year and its absolutely possible for you.


You can still provide a really amazing client experience and have freedom as your number one value. It simply requires you to over prepare and plan. 

Question to ask yourself:

From everyone that I’ve worked with throughout my career, what have been the common themes throughout their evolution of growth? 

They all need different things and they all experience different struggles. Even though they have different
stories or different experiences, the emotions are very similar. 

If you’re just building offers and not caring about the people that are taking those offers, how are you ensuring that they’re getting results? 

Which each client, ask yourself:

  • Where are the possible limitations for you gonna be? 

  • How are they gonna learn the best? 

  • How are they gonna feel the most accountable or the most guided or the most supported throughout this? 

Then build your techniques of how you support them fully centered around that perspective. 

Its simple really…Genuinely care.

 [00:33:00] IT PAYS TO BE YOU

“You can make a fortune by being yourself, but you can lose a fortune by trying to be someone else.”

If you have the confidence and the ability to be vulnerable enough to show up as exactly who you are, then you’re actually allowing people to know you, like you and trust you. And those are three key ingredients to success – Making sales.

It’s about being authentic and being yourself. Its about becoming your own muse and finding your own unique voice and your own unique selling points and your own uniqueness in your industry. Then putting that on display for the world to see it and not being afraid of that. 

We are just completely hardwired to fear judgment. The number one thing that we wanna do as humans is be loved and survive. That’s all that we wanna do. So if you couple that with starting a business and putting yourself out there it’s just gonna trigger all of those emotions within you. If you are someone that has ever experienced any sort of bullying or harassment or trauma, yours is heightened. 

“A huge part personally of me allowing myself to be authentic and be vulnerable is reregulating my nervous system and understanding what my trigger points are and why my body responds and acts the way that it does. Why my mind thinks the way that it does. And then kind of using that as a blueprint of how to manage things moving forward.” 

It’s incredibly powerful to have awareness around your story and your body. To know how you’re gonna respond. To know how you’re gonna feel in your body,  what the next step of your default mechanism is. That way you can use that information to your advantage and do things that will quiet your nervous system.

Because when your nervous system’s you out of whack or is in fight, flight, fawn, or freeze that is when resistance, procrastination, excuses, etc appear.

The first very basic level of moving past that state (ego) is acceptance and acknowledgement. Being able to listen to that voice inside you, rather than just being on autopilot, and letting it guide the way for you.

“If you can acknowledge something, then you can start challenging it. You can start challenging that voice to be like, why? Why do I feel that way? Where is that part of me coming from? Where in my life have I ever felt these sorts of emotions before? Because most of the time it’s not really our current reality that’s scaring us. It’s the lens of the past that is actually scaring us.” 


There’s this misconception with coaching where people believe they’re gonna hire this mentor and that mentor is gonna transform their life. Where we believe that every session we attend, every time we talk to them, it’s gonna be transformative. But the biggest transformation actually comes outside of the coaching container when you’re implementing. 

When you’re working on everything by yourself. Because it’s just you, there’s no one else to hold you accountable. That’s where you grow. 

It’s very much about blending your mindset and blending the strategy stuff together. We can only ever go as far as our minds will let us. You can’t bypass it. Mindset is a continuous thing. It’s not something that you can just do a little bit of work on for a couple of months and then you’re saved, you’re saved, you’re healed, you’re ready to go. Absolutely not.

“So having the balls to declare, I’m not gonna live in default mode. I’m not gonna live on autopilot. I’m actually gonna take the time to take stock of what my beliefs are, what my limitations are. What do I think about money? What do I think about receiving? What do I think about giving? What do I think about showing up, being vulnerable? Growing? Take stock, actually write it down and sit with the beliefs you hold. 

Then working back from there. Where did this one come from? Was it a learned behavior? Was it a experience or was it something that was taught to me or I learned from a mentor? 

It’s about taking stock of how you think and how you feel and where those beliefs have come from. And having the balls to say to yourself, no that doesn’t actually sit with me, that doesn’t feel aligned for me anymore. That’s not what I want. How do I now change this?” 

Give yourself permission to start small and grow from there.

Make sure to tag us with this episode #chillpreneurpodcast @ERINMAYHENRY

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