The Bootstrappin' Journey

“Be the kind of person that jumps off a cliff and learns how to fly on the way down.”

Last week, I quit one of the best jobs in the Australian startup scene, managing the marketing for Hometime, to purse my ‘side hustle’ Bootstrap Marketing, full time.

Over the last 2 years at Hometime, I’ve helped increase revenue by 750%, grown the team from 5 to 130, secured a partnership with Airbnb and worked side-by-side with their marketing team. Oh, and I got travel with the founding team to Europe as well as relocate myself to the Gold Coast - because… I could.

Dream job, right?

So why would one leave such an epic position at such a fast-growing start-up?

I quit because I’m crazy.

I quit because I believe SO MUCH in the concept of Bootstrap Marketing that I want to see many businesses benefit from this philosophy.

I want to share with you what it means to Bootstrap Your Marketing.

But first, it may be helpful for you to understand my background of trial & error.

** If you want to skip straight to “How to Bootstrap Your Marketing” click here.**

THE BACKGROUND - Nature, nurture or just dumb luck?

In 2011 I was accepted into a ‘guinea pig’ degree (nope, I wasn’t previously a small furry rodent).

It was a degree called “Bachelor of Marketing & Media” at Macquarie University and it had never been done before (crazy, right?).

They took 30 eager students, a rough idea of a curriculum and stirred it all together and viola! 3 years later the degree had birthed graduates who now had a taste for the unknown - and a little bit of naive cockiness.

During this degree I interned at a tech company selling business process models to government departments (fyi - I still don’t know what this is).

At the end of this internship they offered me the sole marketing role in the company and I freaked out.

I asked Lawrence Ang, the Professor of Marketing at Macquarie for some advice:

19 Year old Me:

"Lawrence, I’ve been offered the sole marketing role at a tech business in North Sydney. But I have no idea what I am doing and I am scared that I will screw it up. What should I do?"


“Rosa, you will definitely screw it up.
You have no experience in the industry or in this position.
But take it anyway. You need to learn on someone's time."



I took the role and I DID screw up a few times.

I sent some terrible email blasts, set up some uncapped AdWord campaigns and hosted a couple of expensive events….

My last day of High school. Pictured: Dad being totally sceptical of my future and me being overly confident. 😂 - Ps, I was expelled on my last week and wasn’t allowed to go to my graduation ceremony. Lol.

My last day of High school. Pictured: Dad being totally sceptical of my future and me being overly confident. 😂 - Ps, I was expelled on my last week and wasn’t allowed to go to my graduation ceremony. Lol.


In 2016 I ended up moving into account management at Havas; a leading creative agency. I was only there for 6 months before the next biggest milestone in my career occurred.

An ex-colleague from the tech business that I interned at came to me with a bold proposition…

"I'm co-founding a travel startup and we're looking for a marketing manager to join. You have no dependents, no mortgage and no real reasons not to jump ship. Are you up for it?"

Yes. 1,000 times over. Yes.

Was I scared that I had no idea what I was doing? Yep.

But I had the words (again) of Lawrence Ang still ringing in my head.


Me pretending like I know what I am doing. I don’t. Leezair, 2017

Me pretending like I know what I am doing. I don’t. Leezair, 2017

So it's 2016, I’m 22 and I am working in Fishburners in Sydney for a travel and experiences app called Leezair.

We had $1 million in funding, an incredibly capable team and BIG BIG visions. Leezair was the first time I'd ever seen an idea turn into a real product. It was awe inspiring to see a group of people working together to make something happen.

It was also the first time that I truly saw that the start-up 'struggle' isn't bringing an idea to life. It's bringing the idea to the market.

Working at Leezair was fun, emotional, hard and seriously significant in shaping the marketer I am today.

I learned many valuable lessons about running a startup. (I plan to write a blog on this another day...)

I was at Leezair for just over 12 months when I decided I would make the jump and start to work for myself as a freelance marketer.

…another turning point in my career.

At Fishburners I sat next to a crew called Kayla. Kayla was a housekeeping service for Airbnb and was run by two hustlers, Dave & Billy.

The guys were just closing their first round of investment and were looking for a marketer.

I asked them if they wanted to be my first client.

They said no.

Instead, they asked me to be their Marketing Manager.

The founders pulled on my heart strings and sold me the dream (they're really good at that). So I joined the team, we re-branded to Hometime and unknowingly set ourselves out for an epic journey ahead.

In just two years we raised over $12 million, grew from a team of five to a team of 130+. We partnered with Airbnb, grew our revenue by 750%, expanded nationally and internationally to 7 cities. Andddddd we sell over 11,000 nights every month to guests across Australia & New Zealand.


What an experience.


As I mentioned, we grew our team to 130 people. However, until 5 months ago our marketing team was made up of just one - yours truly.

Even though I look back now and think that I was CRAZY not to have hired support earlier, it made me realise how possible it is to bootstrap your marketing yourself. No agencies, no expensive team hires, no lost cash.

In 2018 I moved to the Gold Coast for a change of scenery and to help form the Queensland arm of Hometime.

For a while, I travelled back to Sydney almost every month to hold a digital marketing workshop. A good friend of mine was teaching illustration online and she inspired me to “have a crack’” at teaching my workshops online too.

I did, and it worked. 🤑🤑🤑

Now, 12 months later I have left my incredible job as Head Of Marketing at Hometime and I’ve turned my side hustle into a FULL-TIME hustle, helping others to make the leap themselves.

How good.

So, nurture, nature or luck? Bit of everything I think.

Mostly, it just comes down to having the right people around you. If I wasn’t surrounded by such awesome people who believed in me, plus others leading by example (my big sis Tar has founded multiple businesses) then I may never have taken all these “risks” and now be running my own show.

** please note, it’s very early days. So if I fail miserably, I will write another blog on how all these people ruined my life. **


If you don’t know what you want yet, just say yes to everything.

Someone once told me that we should live our lives as if it is going to be turned into a book.

Whenever you’re presented with an opportunity or a cross-roads ask yourself:

“Which decision will make for a more interesting chapter in my book?”

Follow that one.

Warning - my book will be filled with many tears and lots of “wtf were you thinking” mini chapters.

Even though I have just written an incredibly self-indulgent post on ‘my short story’, I want you to know that I am under no illusion that any one cares about what I do every day.

Chances are that no one is going to remember me and no one is going to remember you. So you might as well take some risks and live a wild life, comprende?

As one of my favourite mentors in this space, Tommy Griffith says:

“There’s basically only two choices:

  • Nothing matters. Why do anything?

  • Nothing matters! Why not do everything!

You can either opt-out, or strap the fuck in, and participate in the absurdity of this miracle we have all been given.”

So, what are you thinking?

One day? Or day One.

Here’s some practical advice on Where To Start With Your Own Business.

A “stoked AF” face after my “last day ever” working for someone else…

A “stoked AF” face after my “last day ever” working for someone else…


Rosa-Clare 💗

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