My favourite startups (or should I say children)


As an investor, should you have a favourite startup?

It’s a big question, and one worth discussing.

Before I get to talking about my favourite startups though, let’s talk quickly about being a parent. I believe there’s a bunch of parallels. For any of us with more than one child, while we love them all equally, at certain times of the day you might find you love one a little more. 

The catalyst could be that drive across the city at 7am on a Saturday morning to the latest sporting commitment, only to have to criss-cross back the other way at 10am in what has now become peak hour traffic to deliver said child to a party, and then pick them up three hours later and get into a battle over homework, house chores, tidying their bedroom (the list goes on). 

It’s usually at some point along this journey where you start thinking about the other child. The one that is self-sufficient, gets themselves across the city, comes home to start and complete their homework and greet you with a welcoming hug. They might be the favourite at that point in time!

You provide your children with emotional support, mentoring, advice and a safe environment in which to challenge each other’s ideas. You also provide financial support more regularly than expected in what sometimes feels like a bottomless pit, wondering when we might see a return on this ‘investment’. 

There’ll be a child that is great with their money, keeping a budget, and doing chores to earn pocket money, allowing them the self-satisfaction of saving for big purchases (Apple watch, sporting equipment, musical instrument — whatever they’re focussed on at that point in time). And then there’s the child that has their hand out just about every week, buying lollies on the way home from school, who always seems to leave the house with either no money or having misplaced their Opal card.

Having a portfolio of startups seems very much like being a parent.

There are the ups and downs, constant challenges and robust conversations — and at certain times or on certain days, one of those startups may be a favourite. 

I love being involved with startups that take my advice, put it into practice, learn from a range of people along the way and positively improve how they operate through continual learning. They show real focus on what they’re trying to build, and how they’re strategically partnering with their clients and engaging with their respective industry.

There are the startups that present a fantastic strategic plan, back it up with a financial model outlining the unit economics of their business, how they’re going to attract, convert and retain their clients with associated costs. And at the same time tell you exactly what their sales pipeline looks like, what’s going to close that month and how the latest product sprint will add further opportunities for their clients. They’ll balance this with an objective view of the challenges they’re encountering, where there’s risk, and the help they need to navigate through this. These startups are not scared to present ‘bad news’, as it’s done in a constructive way asking for help and direction to succeed.  

It’s like the kid that comes home from school, tells you they got into a heap of trouble for being stupid, accepts they were in the wrong and explain what they learnt from the experience so they can avoid doing it again.

The startup that seems to have ‘easy’ success and always delivers good news is awesome! But you need to make sure this is actually good news. Recently, I had an experience where a business was delivering positive reports on how they were operating, but without warning, seemed to run out of money. Trigger a quick fall from favourite to least favourite almost immediately. As a founder, you need to be objective with how you present details about your business, it will instil trust and further develop the relationship you have with your mentors and investors.

So, when it comes to your startups, should you have a favourite?

I could be politically correct and say no, but bugger that, I absolutely have my favourites. And my favourites change on a daily, weekly and monthly basis. 

But I typically love them all equally and expect they’ll all mature into thriving businesses. You want them all to succeed and expect that there’s a good chance this will happen with the right support.  

Having a robust discussion with your startups (or your kids) doesn’t make you love them any less, if anything, it provides the growth and development for each of you and an opportunity to learn. Embrace these challenging conversations and situations — don’t worry about affecting the relationship, but focus on improving it.

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