An entrepreneurial family does not always teach enterprise through formal lessons. Sometimes the most powerful learning happens around the dinner table.
In our family, dinner often began with gratitude, a few stories from the day, and a celebration of what people had achieved. But quite often, the conversation would shift into business, money, social media, investing, websites, ideas and opportunities.
Editor’s note: This article was originally written during an earlier stage of our family’s Enterprise for Kids journey and has been refreshed with updated formatting, links and reflections. Some examples are historical, but the bigger lesson is still very relevant: children learn a great deal from the conversations, questions and opportunities they grow up around.
What Does an Entrepreneurial Family Talk About?
What do you think the Howitts talk about around the dinner table?
It always begins with each member of the family sharing a gratitude. Usually the events of the day are told, small wins are noticed, and achievements are celebrated. But what often happens next is that topics of business, enterprise, finance and investing begin to govern the conversation.
That might sound unusual, but for us it became part of family life. We were not trying to lecture the children. We were simply talking openly about ideas, opportunities, risks, mistakes and what people were learning.
This is one of the quiet strengths of an entrepreneurial family. Children begin to hear the language of possibility. They hear adults and siblings talk about ideas, value, money, creativity, customers, digital skills and problem-solving. Over time, those conversations can shape the way children see the world.
Some of the topics around our family table have included social media opportunities, digital assets, eCommerce and online business. Let’s look at how these conversations can present opportunities for kids and teens to think more entrepreneurially.
How Social Media Became a Learning Opportunity
Our older children, Kaitlin, Jai, Flynn and Amber, all discovered social media when they were in their mid-teens. It started with Facebook, then Instagram, and later platforms such as TikTok and Snapchat.
They learned how to grow a real following by posting regular, quality content about their lives, interests and adventures. It probably helped that we were living on a tropical island atoll in the middle of the Indian Ocean. Photos and videos from Cocos Islands always looked pretty fabulous, and those early creative skills helped shape things like Flynn’s photography and creative work.
As their following grew, so did their opportunities for enterprise. It began with simple things like shoutouts. Other people or companies would pay them to mention a product, page or service in a post. This helped those people grow their followers or promote what they were offering, and our enterprising kids were happy for the cash.
Next came real products. Companies sent clothing, watches, surf gear and jewellery for them to wear and share on their accounts. The kids were able to keep the gear, and in some cases they were also paid for the promotion.
Looking back, this was an early lesson in digital entrepreneurship. The children were learning that attention, trust, creativity and consistency could create opportunities. They were also learning that a following is not just about numbers. It is about connection, value and communication.
Turning Digital Skills Into Real Business
As time went by and their social media followings grew, their creative ideas began to grow as well. Bigger opportunities started to appear.
Kaitlin, along with Tully, began building multiple streams of income using social media, connection and online platforms. Their work included coaching, network marketing and online courses.
Jai took a few years to build momentum, but his early interest in social media and content creation eventually became a real business path. He began creating content for clients and using his digital skills to generate leads and opportunities.
That is one of the things I find interesting as a parent. The small things children play with, practise and explore as teenagers can become the early foundations for future work.
An entrepreneurial family does not need to have all the answers. What matters is creating an environment where children are allowed to explore ideas, test things, ask questions and see real examples of enterprise in action.
That connects closely with our broader reflections on how to raise entrepreneurial kids. Children do not only need theory. They need conversations, experiments, encouragement and real-world opportunities.
Talking About Crypto and Digital Assets Carefully
Another topic that entered our family conversations was crypto. You would have heard about Bitcoin, but many people still do not fully understand what it is, how it works, or why people are interested in it.
For our family, the useful part of the conversation was not “everyone should buy crypto”. It was the opportunity to talk about technology, risk, research, hype, long-term thinking and the difference between speculation and investing.
Important note: This section is not financial advice. Crypto assets are volatile and risky. This article is simply reflecting on how one family used the topic as a learning conversation about technology, money and decision-making.
In simple terms, Bitcoin is a digital asset built on blockchain technology. It was created in 2008 and has a limited supply. People are interested in it for many reasons, including decentralisation, borderless transactions, digital scarcity and the potential of blockchain technology.
But the more important family lesson was this: children and teens need to learn how to think, not just what to buy.
When topics like crypto come up, parents can ask useful questions:
- What problem is this technology trying to solve?
- Who benefits if people buy into it?
- What could go wrong?
- Is this investing, speculation, gambling or learning?
- What would proper research look like?
- How much risk is too much?
Those are powerful dinner table questions. They help children think about risk, evidence, emotions and decision-making. That is far more valuable than simply telling them something is good or bad.
This also links with our article on financial education for kids, where we explore how children can begin to think about assets, liabilities and wiser money choices.
eCommerce and Website Building at Home
Another topic we explored as a family was eCommerce and website building. We were learning how websites could be built, improved, monetised and sometimes bought or sold as digital assets.
Websites can be monetised in many ways. Some common methods include affiliate marketing, advertising, directory listings, services, digital products and online courses.
For enterprising kids and teens, the bigger lesson is not that every child should rush out and build a website. The lesson is that digital skills matter.
When a young person learns how websites work, they begin to understand:
- how online businesses attract attention
- how content can create value
- how products and services are sold online
- how audiences are built
- how digital assets can be improved over time
- how creativity, writing, design and technology can work together
At the time of the original article, some of the younger Howitt kids were building websites. Amber had started a site about sustainable period products. Chayse had bought a site called Baby Client and was working on improving it. Other projects were still a work in progress.
Some of those early projects worked. Some did not. But every one of them created learning.
That is the value of an entrepreneurial family. The goal is not to make every child successful at every idea. The goal is to build initiative, curiosity, problem-solving and the courage to keep learning.
What Parents Can Learn From an Entrepreneurial Family
Our dinner table conversations may be a little different to the average family. We gain inspiration from one another through these conversations and through mentors who support us on our entrepreneurial journeys.
We are building skills, gaining knowledge, creating assets and, most of all, strengthening a mindset for enterprise.
If you want to encourage more enterprise in your own family, you do not need to start with a big business idea. Start with better conversations.
You might ask your children:
- What problem did you notice today?
- What could make that easier, better or more useful?
- What skill would you like to learn?
- What do people already ask you for help with?
- What could you create, sell, improve or share?
- What does this teach us about money, value or responsibility?
Those questions help children see the world differently. They begin to notice opportunity. They begin to understand value. They begin to realise that enterprise is not just something adults do. It is a way of thinking.
Key takeaway: An entrepreneurial family can use everyday conversations about business, money, digital skills, investing and ideas to help children build confidence, curiosity and real-world enterprise. The dinner table can become one of the most powerful classrooms in the home.
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