11. A Graduate Story.

Before you all head off into the real world to start this crazy ride for yourselves, I want to share with you a very true — and very realistic — grad experience.

Meet Kylie, she trusted me enough to attend my very first class — a small group of just 10 ladies — when the ink was still wet on a little cottage she had bought in another state, without having even seen it. I’ve had the pleasure of watching her journey from newly-acquired-empty-home-on-the-other-side-of-the-country to (I think) the most iconic Hobart Airbnb, all within nine months. As you can imagine, I have a special connection to Kylie and think she is such a lovely example of most of us: a limited budget, an Airbnb in another state or city, unsure with our creative selves, anxiety around putting ourselves out there, using Instagram…

…but she trusted me, and she trusted me enough to follow my ways, step by step, with unfailing faith. Needless to say, I am so glad she did.

So! I invite you to look in on Kylie's journey with Captains Cottage. Hers is a ride we’re all on and, at times, we can feel quite alone. My dearest hope is to show you what is next for you after this chapter closes and to prepare you for every challenge that surely will happen.

Captains Cottage, Hobart — Tasmania.

Captains Cottage, Hobart — Tasmania.

11. Dear Fellow Students,

Oh my, what a beautiful journey you are about to continue on. A magical journey of self-discovery, heart-beat skips, and big proud moments! Don’t get me wrong, not everything is rainbows and snowcaps, but pretty close. I was so delighted when Sarah asked me to share my journey with you. We can be given the tools and taught the beautiful lessons, but we have to sail our own ship if we are to be truly authentic.

As it’s best to start at the beginning, I’ll tell you how we became custodians of a small heritage listed cottage in Hobart, Tasmania, and (like all good stories) of course it starts with a dream! My husband and I had been longing to purchase a small house in Hobart for a couple of years and were looking for a Hobart bolthole: something our family could use, but also rent as holiday accommodation. So it became daily looking on real estate websites, calling real estate agents, and going to open homes whenever we were in town. We submitted several offers on various properties, but were always outbid. We had almost given up on our dream when, out of the blue, an agent called to tell us about a cottage she was listing. We put an offer in that day, sight unseen! We then waited two long weeks for the seller to accept. When we received the signed contract we were so excited and couldn’t believe our luck! And it’s there my journey began.

After settlement, we had eight days and a small budget to complete a few cosmetic changes and furnish the cottage. Living out of state comes with big challenges but, thankfully, I was able to order most of the furniture online and have it delivered (the rest we were able to purchased in Hobart). As you can imagine, didn’t sleep much that week! 

A short while later, we commissioned Sarah to style the cottage and, wow, that’s when the beautiful Captains Cottage came to life, shining like a bright, beacon in the night!. Afterwards, I attended the very first face-to-face Masterclass in Queensland and my life changed forever.

When we opened Captains Cottage I knew nothing about inn-keeping, absolutely nothing! What I did know, however, was what I loved and didn’t love about all the different accommodations I have been lucky enough to stay in across the world. This I think was a good place to start. Fortunately, attending The Hosting Masterclass came at perfect timing as we had not been open long and class taught me everything I needed to know about running a successful Airbnb. Such a treasure trove of information! I often refer back to my workbook and notes as it’s the backbone of my business plan.

I am passionate about providing beautiful accommodation and the Masterclass made me realise just how beautiful everything should be. This was a light bulb moment, probably the biggest mind shift. I’ve always had a great appreciation for beautiful things but I am now able to make the connection between the emotional feelings I have when viewing them and the guest’s experience. Captains Cottage is not just a holiday accommodation, it’s a unique experience that only those who visit truly get. Everything in the cottage — from vintage silver cutlery to our handsome gentleman who adorns our loft — must be thoughtful and embedded in the rich story that is Captains Cottage. I’m very passionate about our guest experience and want them to feel how I feel when I’m there. I also want them to feel like they are my only guests.

Running an accommodation business can be stressful…if you let it. It takes time and patience as nothing is instant! I was very conscious of not allowing my expectations to run away with me and I understood that after completing class, Captains Cottage was not going to become an overnight success. I have had to work at it and, as time goes by, I can see I will spend less and less, never zero, but always less.

In the early months failure was a real fear. I knew in my heart that Captains Cottage was special but how was I going to convince a group of people I didn’t know? Also, the reality was, financially we couldn't afford to have the cottage sitting empty. My fears were around bookings, guests not loving the property and, of course, the fear of someone leaving a bad review. What if we don’t get bookings? What if we have this cottage and it sits empty? What if…what if…what if… As you’ve learned, it takes time for a business to grow and be successful so calculate how many nights you need to be booked to cover expenses and begin there. That takes the pressure off and it helps you worry less about bookings (especially once you get in the black month after month, like us).

As much as I love the great romance stories, and I do get a little swept up in the romance of Captains Cottage, I’m not wearing my rose-tinted glasses. I have been and still am very realistic. I did have a magical idea in my head, though, that we would be completely booked out. Well, I very quickly came back to earth from my fantasy daydream! We have organically grown since the arrival of our first guests and I’m very comfortable with that. We are not booking out every single night of the year (yet). but we have bookings every month, for the next nine months. That’s nearly as long as we have been operating!

Reaching Airbnb Superhost was a big milestone. The pressure was on to meet all of the Superhost criteria and those reviews needed to be good! I’m still a tiny fearful of a bad review, but I’m confident that I can manage whatever is thrown at me (like organise an electrician at short notice to be in and out in an hour and line up a complimentary breakfast for our guests, all from 2,800 km away!). Three Superhosts later, I feel I am now rocking it.

This first year I am also learning the seasonal booking patterns of my area and will know when to expect quieter months for next. I think that’s when we may book our own time at the Cottage and get things done.

Other than the out of state challenges, housekeeping was very difficult in the early months. My original housekeeper resigned after a short period and I nearly went into meltdown mode (how will I ever find a new housekeeper while 2,800 km away?!). Then she came back, but needed time off, so she offered the services of a friend, took about three months off, popped her head in and out, then returned! You can imagine we had lots and lots of teething problems. I think if we were living in the same state, I may have looked elsewhere but I persisted and am grateful, as she is doing a wonderful job.

Captains Cottage is a work in progress and I expect it will be a little while yet before we realise the full dream. We have plans to renovate our bathroom and build a beautiful courtyard garden but these have high costs associated with each so we are slowly making improvements as income is generated. It’s a juggle between making good business decisions and following your heart. I never forget that Captains Cottage is a business but I want her story to be authentic and, for that, my heart must sometimes guide.

Instagram has been an amazing business tool and we have new followers join everyday. Consistently showing up on Instagram, using the app as a marketing tool and learning the art of storytelling has been fun and exciting. I don’t get too caught up in the number of followers, although I get a little excited and still tell my husband how many new ones we get (I mention it about every 100!). I wasn’t an active social media user and I’m quite a private person so had to learn to be more open and ‘public’ and tell a story took me out of my comfort zone. Also! What a challenge figuring out who my dream guests are. Who are they? What do they like to do? Where do they hang out? Guests don’t book Captains Cottage because of me, I think they book because I share how it will make them feel when they’re there. Captains Cottage is a sweet, beautiful stay in the middle of a city, romantic and easily swept away.

Using Instagram to offer influencers a stay has also been really successful and they completely fall in love with Captains Cottage, too. The beautiful guest reviews are magical moments for me and I’ve been so fortunate to have many.

I have tried a couple of different things to encourage bookings. I experimented with dropping our night rate for last minute bookings. This didn’t make any difference, which makes sense now as I’ve learnt that Hobart is a planned destination. I also ran a competition and was giving guests a bottle of local Tassie gin. I thought this was the ultimate! I hate to say it - fail. Apparently nobody cares about free gin!

So we are 10 months in now and really gathering momentum. Bookings are coming in more frequently and guests are planning further ahead. We have created a place that has a soul and a unique story to tell and Captains Cottage is becoming an iconic Hobart stay. Many of our guests already know about us, have been referred by a friend, or follow us on Instagram. This is the place I have been working hard to get to. It takes time but is very worth it. It’s about lots of patience and believing in the magic. 

There have been so many magical moments and heart-beat skips since my journey began and it has far exceeded my early expectations. Working full-time at my day job, renovating a home (the one we live in), juggling guests, posting on Instagram, running housekeeping, and growing Captains Cottage has been beautifully exhausting. But now I’m starting to spend less time doing things for the business. Perhaps the hard work is coming to fruit. I still pinch myself that we are the custodians of Captains Cottage. She’s very special, one of those kinds of places that has to be experienced to really feel the story and I never take that for granted.

Next for us is creating a second story: a small waterfront shack south of Hobart. Tiny, with a big, rich story, I am so excited to getting started. My Captains Cottage and Masterclass journey is a wonderful foundation to guide me through this next project and I have no doubt it will grow up to be just as beautiful and unique.

So, for you, I have three key points . . .

  1. Don't expect overnight success. It really is an exponential curve when it comes to opening and then your bookings. People book holidays ahead, then they tell their friends, who also book holidays ahead. It takes anywhere between 6 - 12 months before you really get going, purely because of how people book, travel, and talk about places. 

  2. It's a lot of work to start, then you troubleshoot. Then it gets easier and, one day, it’s pretty bloody easy! Problems that arise are good opportunities to nut out the issues forever!

  3. Follow the process Sarah outlines when it comes to marketing. The methods she teaches for growing your business really are so powerful and you can do them! 

A last thought from me . . . giving all the love, with no expectation, is truly the most rewarding. I wish you all a magical journey.

Kylie X

11. Before The Hosting Masterclass.

11. After The Hosting Masterclass.


11. Watching Kylie Grow.

I am so proud of Kylie. I don’t think many people’s journeys are easy, or success is instant (even though it might appear that way looking in). I invite you all to watch Kylie via her Instagram - @captainscottagehobart — she was so apprehensive about starting out on social media but she tells her story so well, no one else could do it for her. I think she could be an inspiration for a lot of you who live interstate, don’t have confidence with photography (yet), or don’t want to put yourself in the frame like I do with my property.

Something I also love about Kylie’s journey is that it wasn’t perfect right off the bat. I helped her with styling for a few days on a limited budget so she could get going and, over time, she has added pieces herself, modifying storage solutions to efficiently work with housekeeping; she has upgraded the bedding and towels, bought a bigger heater, and so on. She has swapped stays with photographers, stylists, influencers, florists, and all sorts to improve things or spread the word. Kylie has made it work and she has grown as it’s gone, with no more skill or nerve than the rest of us.

I dearly hope you hear what I am saying: you are already wise, brave, smart, and should have the confidence in yourself to tackle what is next.

All my love,

Sarah X