crooked compass tours

Q&A with Travel Expert & Entrepreneur, Lisa Pagotto

Throughout the last few months, I've interviewed dozens of female entrepreneurs but none in the travel and tourism space until I connected with Lisa Pagotto of Here's is what she had to say. 

Please tell our readers about your background.

I started my career in the travel and tourism industry in 2003, straight out of high school. After completing travel college, I entered into the industry as a retail travel consultant. Over the next few years, I worked my way through various roles trying to find my ‘fit’. I moved into wholesale, worked on the road as a tour leader for several years before being offered a position to start up a new arm of an existing business to see if there was a hunger in the marketplace for private customized tours. It was very much a trial and error role – I was advised if it didn’t take off, I wouldn’t have a job in 6 months.

I ummed and ahhed about taking the role as it meant a significant pay cut but took the chance that I could really create something and make it my own. Within two years, I had turned that ‘new arm’ of the business into a $2.2m sector of the company and was promoted to be National Sales Manager. I was 24 at the time and suddenly found I was managing 7 sales managers across Australia and New Zealand. I was in the role only six months before the parent company folded and we all lost our jobs.

From there, I was employed by another tour company to start a new brand for them. I spent the next 12 months constructing and contracting 400 new tours, as well as launching the brand and getting it producing revenue. Whilst doing this, I was also looking after the national sales and marketing for two other tourings owned by this same company. It was at this moment where I had my light bulb moment. I had literally spent the past few years building brands and business for someone else. This is when I started Crooked Compass on the side - building it up and getting it right whilst I was still working full time. There were still significant gaps in my knowledge and experience so I searched for a more strategic role which I successfully landed.

I convinced my husband that my business idea was so good that we should sell our house so I could really make it happen; so that I would have funding behind me to get it off the ground, surprisingly and not surprisingly, he said yes and within two weeks our house was up for sale. We gave up everything – our house, our lifestyle, and my salary. After some time in the strategic world, it was time to take the plunge and I moved into Crooked Compass full time and have never looked back.

Why did you start your business?

I started the business because I saw an opportunity in the marketplace for showcasing emerging destinations and lesser-known side of common destinations. I saw a niche for an experiential travel product that was outside the norm and this paired perfectly with the moving trend of personalization that has been coming for some time. The style of travel I personally do is all about discovering and sharing the unheard of and when I saw others wanted to do what I do but couldn’t find a way to execute and make this happen, that’s when I saw the need for my expertise.

What market does your business serve?

Crooked Compass caters to those who are well traveled, those who have been there, done that and are seeking something more rewarding from their travels. We cater for the 40-70-year-old travelers who have a little more time and money and those who are seeking a deeper level and educational element to their style of travel.

What's the largest challenge you've encountered as a business owner?

The largest challenge is definitely managing cash flow.

What's your best piece of business advice?

My best piece of advice is that starting your own business is tough. We’ve all heard the saying ‘keep emotions and business separate’ but when it is your startup or your baby that you have given everything up for, emotions do come into play, and often this is hard to manage in the early days.

If you are passionate about what you do, people cannot help but be intrigued and want to listen and help. Passion and ambition are addictive. Surround yourself with people who you want to be like.

How do you like to relax?

Believe it or not, by traveling! But when that isn’t possible, I do like to read – usually books about travel or weird far-flung destinations that I may be able to create some sort of amazing travel product in.

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