We recently connected with Rosanna Diogini and have shared our conversation below.

Rosanna, thanks for taking the time to share your stories with us today Coming up with the idea is so exciting, but then comes the hard part – executing. Too often the media ignores the execution part and goes from idea to success, skipping over the nitty, gritty details of executing in the early days. We think that’s a disservice both to the entrepreneurs who built something amazing as well as the public who isn’t getting a realistic picture of what it takes to succeed. So, we’d really appreciate if you could open up about your execution story – how did you go from idea to execution?

My travel industry career started post- summer 2020 when I designed my first website promoting FindYourSail@, my signature women-only, chartered sailing retreat.

Right at the beginning of the pandemic, I found myself sailing with 4 girlfriends through the Ionian Greek Islands, and that time away from land gave me real moments of solitude and self reflection. As women we away so much of ourselves in life and I just needed space to think at a moment of change in my personal life.
As I stared at fish swimming through my legs in clear blue green waters, I had the idea of giving that same opportunity for ‘me time’ to other women and combine it with career/ business mentoring.

As soon as I was back on dry land, I started researching online everything from ‘how to start your own retreat businesses’ to ‘how to design a website’. at 40+ I have years of experience in corporate tech and programme management, so very quickly I organized my branding, my website, my retreat & coaching program, my systems and processes….. and then I got stuck! Corporate did not teach me how to find my own voice & how to sell myself online via social media.

I am reserved by nature and never had much of an online presence, so that was a real challenge for me, and one I am still working on. I had a real issue ‘going public’ with my idea and product and I really worried about what my corporate colleagues, family, friends would think. I also carried a lot of guilt! I have young-ish children, and i felt guilty for spending time away from them to develop this idea, and for even considering giving up a well paid corporate tech role to launch a travel business at the start of a pandemic which had grounded everyone.

Investing in coaching really helped me move forward: finding the right online communities, joining relevant masterclasses or 1:1 coaching – all helped me get to where I am today.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

My name is Rosie and I’m the Retreat Lead & Business Mentor behind FindYourSail@, a women-only boutique (chartered) sailing retreat that gives you the space, time and support you need to find clarity at times of personal and professional change.

FindYourSail started taking shape in summer 2020, when I serendipitously found myself sailing in the Mediterranean sea with 5 women. Sailing allowed me to physically leave my life ashore and gave me real moments of solitude and self-reflexion. On my return I researched and read plenty of scientific articles on the benefits of spending time in ‘blue spaces’ and I took time to qualify as a Travel and Group Coach. In summer 2022 (had to wait post-Covid restrictions) I welcomed my first clients on board!

The journey starts before setting sail, and I encourage women to spend time thinking about what their ultimate goal is for joining the retreat: what lasting changes are they wishing for? I give them tools and guidance on how to prepare for the trip and what to expect from life on board and the group mentoring sessions. I like to call FindYourSail@ a Clarity Mastermind Retreat; I like to think that It provides a safe space for women at personal and professional/personal crossroads to press pause, journey within and explore what change means to them as they approach a new phase of life.

FindYourSail is a boutique retreat and an intimate experience: there are only a maximum of 6 clients on board at anyone time and I only run 3 retreats per year. My intention is to offer a personal experience and by keeping the numbers low I can be fully committed and present.

Let’s move on to buying businesses – can you talk to us about your experience with business acquisitions?

A few years back I bought a bar in Fiskardo, Kefalonia (a gorgeous Ionian Greek Island and where my retreats sail from).

I was solo-travelling off-season, it was March time: Fiskardo was still closed for the most part, aside from the supermarket and the pharmacy nothing stays open there in winter! I walked past ‘The Fishbone Bar’ and it was love at first sight.
The bar sits at the bottom of the prettiest white stone stairs and has the loveliest balcony looking over the harbour and above a row of outside tables. Inside it has a wall of whiskies and a proper bar to sit at on rainy days.

A week later I had found out who the current owner was and I made him an offer: he accepted and that’s how I became an accidental bar owner!

Note that I’m an ex-corporate girl and at that point I didn’t even know how to pull a pint of beer, let alone run a bar. I had to find a local accountant and lawyer, set up a local limited company, negotiate a pile of paperwork in Greek with dubious English translations. Once I owned the bar, I had to negotiate local suppliers and vendors & the police – all of whom looked at me suspiciously, wondering why a London based Italian woman would want to buy a bar in Fiskardo, Kefalonia :)

As a foreign (female!) business owner, It was not easy to be accepted in the local community, but I did my best to get to know everyone and I made an effort to learn Greek (I’m still trying).

I bought the Fishbone Bar on a whim, but it was somehow a calculated risk: it didn’t take me out of my financial comfort zone, the business is only open a few months a year and I have staff handling the day to day – but! I very much believe that we define who we are and what we want to change by the actions we take (or don’t take) everyday. The bar for me was the beginning of acknowledging my need to change how I lived my life.

What’s been the best source of new clients for you?

So far my best source of new clients has been LinkedIn.

I’m yet to master a consistent social media presence, and my business is still in its infancy; I’m still to really establish my social media presence in general – but because of my corporate background I had a LinkedIn account with a decent network built over 17 years.

My clients to date have come from that network.

Contact Info:

• Website: www.timeandtide.co
• Instagram: https://www.instagram.com/timeandtide.co/
• Facebook: https://www.facebook.com/timeandtideclarityretreats/
• Linkedin: https://uk.linkedin.com/in/rosannadiogini