It’s often difficult to explain what it means to be an entrepreneur. Particularly to families whose livelihoods are based on traditional vocations.

Here are some thoughts on this as families start to converge over the holiday season. It’s a time where families casually enquire about the year that was and what the future holds. That enquiry can yield a mix of interest, encouragement and judgement.

This post is for those who think judgement is coming or is a foregone conclusion. Especially for those people with side hustles contemplating a full-time commitment to the product they are building.

Family is complicated at the best of times and the judgement they can cast directly or passively, intentionally or unintentionally can make entrepreneurs second guess themselves.

Four assumptions about family

When it comes time to explain what I do to my family, I use it as an opportunity to pitch and educate. The way I position that pitch is different from how I would pitch an investor or partner. And that’s because I make three assumptions about family.

The first assumption is that they think I have flexibility because I ‘work for myself’. There’s a lot to unpack with this assumption because family members often chose a conventional vocation. These well-worn paths come with apprenticeship models and hierarchies where people have to ‘do their time’ before moving to the next level of seniority. With fixed shifts and working hours, this can feel inflexible compared to entrepreneurs who can work at whatever time they need to.

We know that we work many more hours than a standard working week. But this perceived flexibility can be met with a degree of envy and potential resentment because they didn’t have the chance (or courage) to pursue a similar path.

While these emotions may not be factors affecting the conversation, I dial up the empathy and pitch as if it’s an issue.

The second assumption is that employees of companies don’t often realise that their companies were startups once too. It’s not part of their psyche that at some point in history, an entrepreneur took a bold decision and likely risked it all to build the brands they take for granted today.

They are not my target customer is the third assumption. Using a sales pitch to family and friends for a product they may never use won’t help this conversation.

And the final assumption is one of optimism. If family understand what I’m trying to achieve, they can become an evangelist of my company.

I believe in the notion that practice makes perfect and to always go a little further. So when it comes to family occasions, like Christmas, I look at pitching family, when they ask about my work, as an opportunity to get better at telling Drop’s story.

I’m also ready for what comes next. The anecdotes and ideas that come back at me as the person I’m speaking with tries to internalise and make sense of Drop in their context. I admit that I take their comments with a grain of salt. However, I also listen for any confusion that comes as a result of my delivery. Herein lies opportunity to improve.

A template to pitch family

Here is the model I use to describe what it means to be an entrepreneur to family.

So I’m building a company called [Name]. We help [customer type] [pain point that the company solves]. There are [number of people with this problem]

Because it’s me and a team of [number of team members or freelancers], the days are long, we often work [number of hours worked per week], but we are making solid progress, and I’m really interested in this area. We have [add traction statistic you are most proud of] and next year we plan to [add one key grown objective for the following year]. 

Let me send you some information about [company name], so you can read about it later.

I immediately send an SMS / WhatsApp with a link to my company’s website, and then I listen to what they have to say.

This approach has helped me share the name of the company, who we serve and the problem we are solving. The effort invested and traction achieved is described humbly, and the future is bright and demonstrates that you are in motion on the business model. Importantly, you make it personal by you sending a link to their device. That one gesture has paid dividends for me in the past.

By way of example, here is what I’ll be saying this holiday season:

So I’m building a company called Drop. We measure inflammation, over time, using finger-prick blood taken at home to empower people to understand changes in their health because chronic inflammation plays a central role in health and disease, in fact, it’s the bodies natural early warning system. We think we can help more than 500M people in the next decade. 

Because it’s a team of six and me, the days are long, we often work 80-90 hour weeks, but we are making substantial progress, and I love it. We are nearing the end of an important proof-of-concept study to which we attracted over 600 participants in 10 days. We were only looking for 50 people. In 2020 we will start supporting women on their pre-pregnancy journey and enter the Singapore market as a gateway to Asia. 

Let me send you some information about Drop so you can read about it later.

The irony is that you will get better the more you pitch!

And because I can’t help myself, I often send a follow-up SMS / WhatsApp asking if they have any questions a week or so later.

One last thing…

Don’t hide from the fact that your family might not understand what you do as a founder. Get over the idea that they won’t understand.

Teach them.

Set yourself the challenge to convert them into evangelists.

Pitching is the last thing you might feel like doing after a big year. But if family understand what you do, there is an excellent chance you will unlock latent support.

The best-case scenario is that they tell everyone one they know and you receive the next level of support from the people closest to you. The worst-case scenario is you receive less judgement for being a pioneer.

That feels like a win: win to me.