MY STORY: From Bartending To $300K Freelance Copywriter To 7-Figure CEO

I’ve shared bits and pieces of my story here online over the years… 

But you’ve never heard the WHOLE story.

Until now. 

Hey Posse, what’s up? It’s Alex. 

A couple of weeks ago, I shared what I call my “falling from grace” moment with thousands of the Posse community during a LIVE online masterclass. 

It’s always a little terrifying to be so open about the hardest and lowest point of my life… 

Especially with strangers on the internet.

Because let’s be honest… 

Most of you who read these blogs are super rad humans and very supportive…

But I do get less-than-supportive-internet-troll comments from time to time…

And I’d be lying if I said the comments don’t get to me sometimes… 

And to be honest, I guess that’s why I’ve never really WANTED to share my whole story on a public platform. 

I don’t want a vulnerability hangover tomorrow…

But I was inspired to share my story – because after sharing it during the masterclass, I received some really heartwarming messages from people all over the world telling me how encouraging it was to hear my story.

So I’m going to share that story here today.

I hope it will help, inspire, or encourage you as you inevitably encounter your own struggles, hard times, and low points. 

But before we get into it, if you’re new around here, make sure to join my newsletter for more real talk about digital marketing and what it’s like navigating this wild world of entrepreneurship. 

Now let me tell you a story… 

Something you might not know about me is that – even though my YouTube Channel and my brand (the Copy Posse) are only about 4 years old…

I’ve been in this world – the world of copywriting and digital marketing – for like… over 16 years.

I started off as an intern at Mindvalley, one of the world’s leading online publishers, and went on to become the Creative Director and then the Director of Mindvalley’s annual event Afest.

I’ve been lucky enough to meet and learn from so many incredible people who I know call friends and peers…

People like Brendan Burchard, Vishen Lakhiani, Marie Forleo, Jim Kwik, Lisa Nichols, Bob Proctor Joe Sugarman, Frank Kern and Jeff Walker… even Matt  Mullenwag, the guy who developed freaking WordPress.

I learned everything I know today from these people and I wouldn’t be who I am or where I am today without their influence in my early career. 

But let’s rewind a bit because the story starts YEARS before any of this. 

March 17th, 2008

I remember it well. It was St Patrick’s Day. This is what I would consider the FIRST “low point” in my life…

And it wasn’t because I was rocking horrible bangs.

I was 23 years old, living in my parent’s basement, bartending, and serving at a restaurant to earn a little cash. 

EVEN THOUGH I had a business degree. 

I had no idea what the hell I wanted to do with my life. 

My twin brother was off to Med School and I felt all this pressure to do something equally as great, to measure up and prove myself. 

I had my business degree and thought Law School was the best next step. 

It’s what everyone was expecting me to do…

It’s what I SAID I was going to do… so I started studying for the LSAT and researching law schools.

The problem was I had this nagging feeling that Law School was not for me.

I didn’t know WHAT I wanted to do, but I knew deep in my bones that Law School wasn’t it and the corporate grind was not for me. 

So one night, I went down the rabbit hole online, and I found a 6-month customer support internship for a little startup company – called Mindvalley – in Malaysia. 

I thought “Well, spending 6 months in Malaysia while I figure things out sounds pretty damn nice”…

So I applied and…

I got the job.

Within a few weeks, I had:

• Sold my car
• Quit my job
• Packed up my life into two bags.
• And was off to Malaysia. 

I didn’t know it at the time…

But I was about to dive both feet in to the world of sales, online marketing and personal development. 

And my life would never be the same. 

2008-2011

Suffice it to say…

I quickly became OBSESSED with everything I was immersed in. 

And that short 6-month internship to “figure things out” turned into an amazing 3 year career of massive growth and learning. 

At the time when I joined the team, Mindvalley was not the massive company it is today. 

We were a very small team.

It was a scrappy startup environment and “all hands on deck” was the philosophy. 

And I loved it. I jumped at any and every opportunity I could to take on more responsibility.

And it paid off. 

During my time at the company, I was promoted 3 times…. 

First from customer support intern to project manager…

Then project manager to business manager… 

Then business manager to Creative Director & Event Director of A-Fest. 

The company grew rapidly during my time there. 

From a scrappy start-up no one had heard of…

To a multimillion-dollar company leading the way in personal development and digital marketing. 

It was a wild 3.5 years. 

During this time of my life, I felt like I had “made it”. 

I was 26 years old…

The Creative Director of a multimillion-dollar company… 

I was traveling to the most gorgeous “Instagram-worthy” places nearly every single weekend – Bali, Singapore, Thailand, Australia, Cambodia… 

Island hopping, scuba diving, and having the best adventures on the regular.

I was surrounded by hundreds of like-minded, incredibly inspiring, and passionate entrepreneurs every single day… 

I worked directly with some of the hottest transformational authors on the planet and regularly networked with the giants of the marketing industry.

From the outside looking in, I had it all…

But what you would never have known looking at all these pictures is…

I was very, very sick. 

2011

I was having severe health issues. 

Fatigue, panic attacks, severe nightmares, allergies, gut issues, and the list goes on and on. 

It was hard to function on a day-to-day basis. 

My brain and body were going haywire ALL the time. 

I was on the brink of a complete mental and physical collapse. 

So I made the tough decision to quit the job I loved so much.

Even though I was incredibly successful…

Even though I was making more money at 26 than I ever thought I would in my lifetime…

Even though everyone thought I was living the perfect life… 

Even though I had been involved in growing this incredible company into a multimillion-dollar success…

Even though I had a huge network around me… 

Even though my parents, my family and my friends were all so proud of me…

I quit my job.

I gave it all up. 

And I moved back to Canada into a small bedroom apartment – sleeping on an air mattress in my friend’s spare room.

I had a very small savings account, a ton of health issues to figure out, I had no idea what I was going to do moving forward. 

AND the icing on the cake was that I was also going through the worst breakup of my life. 

It was a TOTAL starting from scratch moment. 

My Fall From Grace

This was my fall from grace era. 

It was a really tough transition period for me. 

I was diagnosed with Celiac Disease – and figured out that was the cause of all my health issues.

Now this was back in 2011 and no one was talking about Celiac Disease back then like they do today! 

You’d think getting my diagnosis and healing my symptoms would have been the happiest moment of my life…

But I was miserable. 

I beat myself up and was sooooo hard on myself. 

“If only I had gotten my diagnosis earlier, I never would have needed to quit.”

I felt like I had just ruined my life.

And it didn’t help that EVERYONE who knew me thought I had lost my damn mind. 

To leave behind that cushy salary, the career, the title, the connections, and the luxurious lifestyle. 

I was devastated. 

I felt like I had made the wrong decision. 

I cried myself to sleep a lot – like every single night. 

I’ll never forget the night I took this photo…

I had just got off the phone with a good friend of mine. 

He told me, “Take a picture of yourself right now because one day you’ll back and think ‘dang girl, look how far you’ve come’”.

Of course, I was annoyed with that advice at the time. 

But I took the picture. 

And I’m so glad I did. 

This night was a turning point for me. 

Okay. That’s enough. You made the decision. Now it’s time to figure this out. 

2011-2017

So I started my freelance consulting & copywriting business. 

I had just spent the last 3 years working in digital marketing, learning from some of the GREATEST marketing minds. 

So the logical thing to do was to start my own marketing business and put all that knowledge to good use. 

The only problem was… I didn’t have any clients. 

And the only connections I had were part of the company I had just left – so no way to get clients from there.

Plus, I was embarrassed and felt very ostracized from that whole world…

And I was too proud to ask for help. 

I wanted a fresh start. And I was determined to do it on my own. 

So I started networking like crazy. 

I went to EVERY marketing conference and event I could find. 

I started getting a few projects here and a few clients there… 

But nothing major happened for a while. 

After a few months of doing this – I was barely scrounging up enough money to pay my rent and my savings account was totally empty. 

Then I went to THIS event. 

And it changed everything for me.

I met this couple – who owned a company and happened to be looking for some copy support. 

We hit off right away and they decided to hire me for a $750 project to update a sales page…

Shortly after that, they became a $1500/month client…

Then $4500/month…

Then $8000/month…

Then a 6-figure a-year client. 

I worked with them throughout my ENTIRE freelancing career. 

They were the first people to really bet on me and trust me. 

Because of this ONE client, I was able to get some good experience under my belt and grow my confidence. 

I got a ton of referrals by working with them. 

My first year as a freelancer I made $43,000…

In the second year – my confidence and momentum really started to pick up. 

I was getting referrals and getting more clients without having to network. 

By my third year, I was making over $300k as a freelance copywriter. 

And I kept that up for 5 more years. 

Just me, my laptop, and a handful of clients. 

I started traveling again… 

I started to feel like I had  “made it” again. 

By this point, I had really established myself as a copywriter in the personal development digital marketing space. 

I helped launch several successful brands and was the driving force behind many multi-million dollar launches…

I became co-host of a high-end mastermind event that gathers the world’s leading internet marketing entrepreneurs…

Everything was great. Life was good. 

But then… it happened…

2017

I was about 6 years into my freelancing career when it happened…

That nagging feeling came back. 

While I LOVED what I did – I loved digital marketing, copywriting, and helping brands scale. 

But being in the industry for so long, I started to notice a dangerous divide…

There were businesses out there with empowering messages that were selling products that genuinely helped people…

And then there were the other people – the ones who gave marketing and online sales a bad reputation.

There were so many marketers and copywriters who were using manipulative, scammy, and severely outdated sales tactics…

I was seeing things being pushed through that I refused to put my name on because I believed it to be unethical. 

I was really lucky that most of my clients were awesome people who loved my approach to marketing…

But it was starting to feel like everywhere I looked, something shady was going on. 

And I was guilty by association – or at least that’s how it felt. 

I remember one time at a party, some guy asked me what I did for a living…

When I told him “I’m a copywriter”…

He said, “Oh – so you’re one of those people who sends me spam emails.”

Spammy emails and scammy sales were everywhere. 

It was embarrassing. 

And I didn’t want anything to do with it anymore. 

I couldn’t understand why NO ONE was talking about this…

So I decided that I would do something about it. 

I decided to start a YouTube channel…

I posted my FIRST VIDEO in January 2017…

It was HORRENDOUS…

And then for TWO WHOLE YEARS…

I did nothing.

2019

So I had this message I wanted to share and I was really passionate about it…

But I was also terrified and dipped my toe in the water back in 2017 and gave up completely. 

There were so many doubts and negative comments in my head about going all-in on my YouTube Channel…

• “Who do you think you are to teach people about copywriting?”
• “What if your colleagues from Mindvalley see these videos?”
• “What if Jeff Walker, Frank Kern, JOE SUGARMAN or all these people you learned from see these videos?! They’ll laugh at me”

And on and on…

Oh imposter syndrome. WHY?!

So I found ANY and EVERY reason to “delay” starting my channel…

My background wasn’t “professional” enough…

I didn’t have all the right gear and equipment… 

I was terrible on video…

That’s what I was telling myself. 

But the reality is – I was playing small. 

I was procrastinating and putting it off because MASSIVE CHANGE IS HARD AND SCARY. 

And this is something I bet every single person watching this video can relate to…

How long have you been: 

• Waiting
• Hesitating
• Playing small
• Or letting fear stop you from pursuing your dream?

Comment below and let me know!

I was IN IT. 

But finally… I did it. 

February 13th, 2019

I published my first “official” YouTube Video. 

I was still working full-time with clients and was doing this “on the side”. 

My first few of videos sucked. Not as bad as the one back in 2017 because at least I had my lighting on point, but they weren’t great.

But I still did it.

I continued to show up every single week…

Even though it felt like no one was watching. 

August 9th, 2019

I hit 1000 subscribers. 

FINALLY. 

6 whole months after starting my channel, posting a new tutorial every single week…

I hit 1,000 subscribers. 

People were starting to leave comments on my videos and sliding into my DMs to tell me what they were struggling with. 

They wanted freedom, they wanted to learn how to write, they wanted to learn how to use their passion and creativity to make an impact in the world. 

And so I decided to create something to help them…

Even though, at this time, I had a VERY SMALL following. 

January 29th, 2020 

I launched my first product – the Copy Posse Launch Pad.

An 8-week program I designed to help learn how to write copy and start a copywriting business from scratch. 

Like I said, my following was very small. 

My email list only had 2300 people on it. 

I’ll never forget thinking that if just ONE person bought the course, it would be worth it… 

But it wasn’t just one person who joined…

44 people joined. 

I just remember thinking: “Wow, people really CARE about this. People WANT to know how to sell ethically and have empathy and integrity.”

The Copy Posse was officially born.

And the rest was history… 

Over the past 4 years, I’ve created several more offers…

• The Write & Ignite Challenge – teaching my sales pages formula…

• Own The Inbox – my email marketing program…

• The Posse Eye – helping you create a brand voice guide that stands out…

• My Look Legit Website Toolkit – containing all my website formulas…

• STORM – a full marketing course for business owners…

• I launched REIGN – my high-level mastermind for copywriters and entrepreneurs…

• And most recently… SPARK – a membership for copywriters who want to make $10k/month. 

I’ve spoken and presented at hundreds of events all over the world…

I’ve made dozens of new friends, mentors, and colleagues…

I’ve been featured in Forbes magazine…

Named 2022’s Digital Marketer of the Year…

In 2023, I was voted the #1 most popular copywriter…

I was the winner of the “game changer” award at 2024’s Women of Inspiration Ceremony…

Image from Copy Posse Instagram

And the Copy Posse has served over 7,000 customers. 

For all the incredible high moments I just listed…

There have been plenty of lows along the way too. 

Days I’ve felt like I disappointed myself and the people I love most… 

Times I’ve received really hurtful comments…

Months I’ve worked myself to complete burnout… 

And many moments where I feel like I have NO IDEA what I’m doing…

I have to fight the urge to not compare myself to other creators and entrepreneurs online…

There are days when I feel like I’m getting it all wrong (hello imposter syndrome!!!)… 

I spend nearly $100,000 on high-level masterminds every single year and I REGULARLY feel like I don’t belong or that I have nothing of value to contribute… 

I often feel like my success so far was just a “fluke” and that any day I could lose everything I’ve worked so hard for and let everyone down…

And there are plenty of days when I miss being “just a copywriter”. 

Running a business, being a boss and being responsible for the livelihood of so many others feels like a lot. 

But I am SO PROUD to be where I am today.

I am SO PROUD of the Copy Posse and everything it stands for. 

I am SO PROUD to have helped thousands of people live a life they love. 

It hasn’t been an easy journey…

But it has been worth it. 

And if you’ve gotten this far the main thing I want you to walk away is this…

YOU CAN DO IT TOO. 

Whatever it is that is on your heart and in your mind…

You can do it. 

It probably won’t be easy…

But I hope hearing my story helps you realize that it’s not easy for ANYONE. 

Everyone struggles and has their low moments. 

All it takes is ONE decision…

ONE client…

ONE moment of courage to change your life forever.  

Always trust the process. 

I hope you found this article inspiring, comment below and let me know what dream you’re chasing…

Until next time, I’m Alex. Ciao for now.

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