Jessy Lipperts

Educate yourself constantly, read books from those you admire, always try to connect with people in a meaningful way and see how you can be of service.


Jessy is a solopreneur who accepted a 5 month ‘gig’ in Cape Town, South Africa in 2003 after losing 8 jobs in 3 consecutive years in her home country The Netherlands. The ‘gig’ was the pre-opening of a 5 star hotel in Cape Town and the Cape Town International Convention Centre. Upon arrival she KNEW she was not going to leave after 5 months.
5 months turned into 15 years when she set up her boutique travel agency and blog in Cape Town. Her mission in life is to create positive ambassadors for South Africa by giving travelers the most amazing experience they could wish for.

She’s passionate about education, languages, travel and community development. Jessy is an adoption activist, has traveled to over 40 countries and enjoys connecting people to make the world a better place. Jessy has a Bachelor’s Degree in Hotel Management but having said that, she’s always enrolled in some workshop or program to improve herself. Currently she’s about to complete a transformational leadership program with Partners for Possibility ( where business people are linked to school principals of under-resourced schools to find creative solutions for the education crisis in South Africa. Jessy lives in Cape Town together with her 5 year old daughter who has traveled to 6 countries so far. Together they enjoy going on road trips all over South Africa. Jessy speaks 6 languages and her daughter already 3.

Where did the idea for PlanetPigrims come from?

I was working as a tourist guide for a Dutch company in South Africa. The tours were very long and quite rushed. A lot of people on my tours told me they would love to stay a bit longer in certain places. I then had the idea to start creating tailor made trips to Southern Africa for those travelers who would like something special.

What does your typical day look like and how do you make it productive?

My typical day starts at 6am in the morning when I make breakfast for my daughter and me and make her lunch box. I then bring her to school at 7am. Then I go on my morning walk along the sea and hope to spot a whale or dolphins. I usually start work at about 9am. This can be at home or at a close by coffee shop or when we are traveling it can be anywhere with internet. I work best when I have a simple to-do list which should always start with 3 income generating tasks so either send out an invoice, a quotation or follow up with a prospect.

How do you bring ideas to life?

Curating tailor made programs and experiences is a wonderful creative process. Since a couple of years I create Global Citizenship Internships for schools and universities. It took me about 2 years of networking and connecting with NGOs, organizations, schools , projects etc etc and I guess this is always how I start: connecting with people or organizations who might be able to help create a meaningful program.

What’s one trend that excites you?

Travel is no longer just a holiday. From experience travel we are now moving more and more towards travel where people want to give back, use their skills and knowledge and truly make a difference in a meaningful way and yes this can be combined with a safari and wine tasting too.

What is one habit of yours that makes you more productive as an entrepreneur?

Making to-do list, always learning, there’s always some course or some workshop that I attend to learn and educate myself.

What advice would you give your younger self?

Don’t worry about university degrees, follow your passion. It sounds really silly and cliché but as a child I wanted to become a truck driver because I could imagine all the countries they travel to and through (I’m from The Netherlands) and I thought that would be so exciting. I was always told, you can’t make money in travel so I choose to go to Law School instead… What was I thinking?? It took me many years and many horrible jobs before I got into travel and started my business on the other side of the world in South Africa by following my heart and saying ‘yes’ to a project that was supposed to take me back to The Netherlands after 5 months. Instead I’m now here since 15 years!

Tell us something that’s true that almost nobody agrees with you on.

God is Great! I’m on my own with this one in my circle of non-believing friends.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Educate yourself constantly, read books from those you admire, always try to connect with people in a meaningful way and see how you can be of service. Don’t just throw around your business card, first see if you can connect the person with someone in your network and help someone else.

What is one strategy that has helped you grow your business?

Word-of-mouth has been the best marketing for me. The big advantage is that people will already have trust in you so in 98% of the time the inquiry will become booked business. Sharing all my wonderful travel experiences on my personal Facebook page, in a way it is also word-of-mouth I guess. Picked up my biggest client that way as well as many people refer me to their friends once they know they’re planning a trip to Southern Africa.

What is one failure you had as an entrepreneur, and how did you overcome it?

I had to liquidate my company at some point. It felt as failure but at the same time I had the most clients ever so I had to trade in my own name for a while. It was a weird time and I needed to find help with something I had no clue of how to do it. Luckily I found the perfect person to help me and that I trusted completely but this was only after meeting many dragons who just wanted to send me massive invoices for no work done. It was pretty awful.

What is one business idea that you’re willing to give away to our readers?

Start a niche web site about something that sells well on Amazon.

What is the best $100 you recently spent? What and why?

I signed up for a course about SEO, affiliate marketing and creating an income generating web site. Each month I pay USD100 for an incredible amount of course material so it is really well worth the money. Bookings to Cape Town went down in 2017 because of so called water crisis, it was so badly communicated so I want to change my business model in such a way that my web site itself can also generate income. Until now it was just a showcase of all the trips I’d organized but now I’m learning to write content in a different way and sign up with affiliate partners and have given myself till the end of 2018 to make it work.

What is one piece of software or a web service that helps you be productive? How do you use it?

That would be the Build Blog Freedom online course that I talk about in question 12. It is very practical so whenever you learn something new you can implement it on your web site and then watch the progress. I already ranked #1 in google for 1 key word so it is great that you can track your own results because it is all part of the course.

What is the one book that you recommend our community should read and why?

Any book about gratitude. I only learned about gratitude well in my 30s and it changed everything, not only in working life but in daily every day life as well.

What is your favorite quote?

It always seems impossible until it is done, Nelson Mandela.

Key learnings:

  • By starting your day with 3 income generating actions, you already win.
  • Invest in yourself by educating yourself continuously by reading books, attending workshops, participate in a leadership program. Not only will you gain knowledge, you will also extend your network of people with similar interest and / or businesses.
  • Count your blessings each day. There’s a LOT to be grateful for. Not only big things.
  • Be a connector, see how you can connect people who might benefit from each other. People will do the same for you.
  • Find your passion and see how you can turn this into a business model that works for you, your family and your life style.

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