Lisa Messenger x Girlboss: A Binge-Watcher’s Guide to Business


Can't. Stop. Streaming.


I’ve always been intrigued by Sophia Amoruso’s story, which, as you probably know, debuts today as a brand-new series on Netflix. It’s an adaptation of her journey from dumpster-diver to e-commerce fashion queen. Luckily, we were granted early access to all 13 episodes. As there are numerous parallels in our stories, I really wanted to offer up my own commentary on the series, with a business eye and as someone who’s trodden a similar entrepreneurial path.

If you know me, you’ll know I don’t do things in half-measures. So when Girlboss loaded up on my tablet, I devoured it hungrily. The show is an absolute delight – it’s achingly funny, heartfelt and, most of all, loaded with lessons for all you entrepreneurs-in-the-making. Instead of straight episode reviews, I’ve scoured each for pertinent quotes or insights into being more business savvy. Also note: any references to Sophia are to the show’s character, of course, not the real-life Girlboss we all know and love.

Here we go!


Lesson 1 | Everyone has wisdom to impart

I liked the scene in which Sophia is down on her luck and sitting beside an older lady on a park bench. The woman imparts wisdom way beyond Sophia’s years. It’s a great juxtaposition of millennials thinking they have all the answers and the elderly with their pearls of wisdom. Personally, I love, love, love, in business, listening to people across all generations, from all walks of life there is wisdom in everyone. In fact, Iris Apfel at age 94 has been one of our best selling cover stars yet.

Lesson 2 | Everyone starts somewhere

From Sophia running out of petrol and having to push her beaten-up old car up a hill, to working in a dead-end job that annoys the crap out of her, and also dumpster diving to get a half-eaten burger which she then proceeds to eat sitting on a stolen rug… she does display a bit of the old, “the world owes me” attitude.

When I started my first business, I literally had a desk that someone “gifted” me. It only had one leg, so the rest of it had to be propped up with telephone books – well, it was 2001; telephone books still existed! I had a Mazda 121 that looked like a jellybean. The driver-side door was broken, so I ended up having to climb through the window. I worked in “jobs” before I started my own business, where I always thought I knew better, wanted equity (even though I didn’t know what that meant at the time). Just like Sophia got fired from her shoe-shop job, I pretty much got fired from the last job I held in 2001 because I wouldn’t toe the line – in hindsight, it was the best thing that ever happened.

So the lesson is: however “big” you think anyone is – always remember they all started somewhere and it’s normally pretty unglamorous. Just remember: one day this will be great fodder for your own “start up story”.

Lesson 3 | Using your frustration to push you into something better

Like everything in life – flip it to see the opportunity, not the obstacle. While Sophia worked in a dead-end job that was driving her nuts – it was this frustration and rigid way of doing things that ultimately amped her up enough to push into doing her own gig. Like so many of us, she wasn’t cut out for the status quo or doing things according to small thinkers with rigid rules.


Lesson 1 | The art of mark-ups

OK, buying something for $9 and selling it for $650 – that’s one hell of a mark-up for your first business deal. So don’t get ahead of yourself and expect that this is going to happen to you on Day 1, but it just takes one little win to put that fire in your belly to keep going.

I always say that when I launched Collective Hub, I knocked on at least 80 corporate doors before I got one ‘yes’. It actually didn’t matter if the yes was for $20 or $2 million dollars (as an aside, it was for a sweet $200K). The fact was someone other than me believed in the idea, and that was enough at the time to give me the tenacity and fire to keep going. And so, just like Sophia’s business was seeded with one single eBay sale, so was Collective Hub – with one corporate ‘yes’.

Lesson 2 | Do something you love

“You found something that you like doing and you are actually doing it”

Watching this show is getting me excited. I can literally feel that drive and excitement all over again – when you get even the smallest whiff of, “I’m on to something”, it’s just a big fat “f*ck yeah!” When you love what you do, the synchronicity and serendipity all just seem to take care of themselves. The universe digs confidence!

Lesson 3 | Don’t underestimate just how big you can get

“I just want to spend all day in my undertrunks in bed … it’s a lifestyle, not a business”.

When you truly find something that’s a pain point for you, chances are others feel the same way, so what starts out as something fun to pay the rent and offer a good lifestyle, may actually start to gain momentum of its own and grow into something bigger than you could ever expect.

In the case of Sophia and Nasty Gal, and my own parallel journey with Collective Hub (which incidentally was never meant for the consumer market or to be sold through news stands; I was just intending on doing a few bulk sales into corporates… 37 countries and 18 or so revenue streams later…).  All I’m saying is just make sure you’re ready, because having chatted to Sophia herself extensively on this subject, both of us just started our businesses to have a little fun – we had no idea just how big they could get. And, quite frankly, neither of us were prepared for the responsibility, the systems and processes, and operational and organisational structure that would be required… so take a leaf out of our books and don’t gear up for or be afraid of failure – instead, gear up for success!


Lesson 1 | Naming your business

There are so many things to think about when doing your first start-up. In my experience, it’s the simplest of things, like naming your business or getting a website or registering a business name, that we completely overlook. OK, this is really embarrassing (and you can read about it more in Issue 3 of the mag), but when we started, the mag was called Messenger Collective. For a few reasons – a quick search told me that I would never be able to trademark the name “Collective” on its own, so I thought it was a safe way to add my name (in little letters to avoid ego) at the top of the masthead. Very quickly, someone threatened to sue me as there was an existing newspaper chain called “Messenger”.  I then changed it to Renegade Collective. Then that wouldn’t fit on any of our social channels, so we called everything Collective Hub across our social profiles. But what I forgot to do, until about two and a half years in, was to register the business name Collective Hub (even though we had it trademarked.).

That could have cost me a fortune. But, luckily, the person who had actually registered the name Collective Hub was kind enough to sell it to me at a reasonable price. Never underestimate the power of a name and the due diligence associated with it. We never really worry when we’re little, but as you start to grow – trust me, you want to be protected in every way possible. Brand is everything!

Lesson 2 | Get out of your apartment (or out of the familiar)

Throw yourself into different places and spaces. Get comfortable being uncomfortable. There is inspiration everywhere, and just like that, out of the most unexpected of places – in a club in the middle of the night screaming the words “Nasty Gal” to a song and feeling totally in your element – a business name is born.

Lesson 3 | Always have fun

The character of Sophia has this in spades… mostly to do with stealing random items, but she has serious attitude and grit and I like that. “Crazy, tough, cool, brash, spontaneous, beautiful, fun…” words her new lover describes her as … good qualities to have. It’s so important (I can’t stress just how much) to have someone or something to distract us. When we love what we do and are on purpose, we want to do it 24/7, which is neither healthy or sustainable, so it’s awesome and imperative to have someone or something to distract us!


Lesson 1 | How to deal with customer complaints and scathing reviews

“This isn’t about me being right or about her being a lying sack of shit”.

Always, always, always protect your brand and go the extra mile for a customer… They won’t always be happy, but do what you can – Sophia goes above and beyond to make “Lady Shopper 99” happy, but it seems it all still ends in a flood or tears, until it doesn’t. We all want repeat customers and great word of mouth. So much of Collective Hub has been built (thanks to our amazing community) on word of mouth and recommendations.

Lesson 2 | Beware of third-party intermediaries / take responsibility over quality control

This is a great in-cheek comical piss-take. The stained dress is dropped off by Sophia at a drycleaners called “the best dry cleaners”. The guy who works there assures her that the stain will absolutely be removed. Sophia leaves it completely in the hands of the dry cleaner (who she has not previously dealt with) and doesn’t leave herself a buffer in terms of the return. It’s an early-stage rookie mistake and trust me – we’ve all been there. In so many aspects of any business, we deal with customers and suppliers, and we are just the intermediaries – as in, we produce products, but we rely on suppliers to give us the goods which we then give to the customers. In my early days of business, I made multiple (costly) mistakes in this area.  

One of my businesses was a book-publishing business. So we had a client wanting to write a book and then we had suppliers who would edit, proof-read, design and print the product. There were several disasters, but a memorable one was when a printer completely printed a wrong (old unedited version) part of a chapter… we had no recourse – we were, after all, delivering the product and the client had no direct contact with the printer. It was our fault completely. From that point on, every single contract we had with a printer (or any supplier) emulated exactly the contract we had with a customer. So if we had to sign off on every page of a book before it got printed, the client had to sign off on every page of the book. That way, we removed ourselves from liability and expensive mistakes from which we would have no recourse.

Lesson 3 | When you’ve got your back up against a wall, time is everything

Time is our only finite resource and while we can trade just about everything in business and life, we cannot trade or buy more time. This is cleverly demonstrated as the pressure mounts and there is a countdown from how ever many days till Sophia’s customer’s wedding until, suddenly, there is a countdown in hours and minutes and then minutes. We can literally feel the pressure through the TV screen – and trust me, we’ve all been there, and no excuse in the world is going to save you when you’ve got an angry or desperate client.


Lisa Messenger



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