Starting & Selling a Start-up in my Teens: My 5 Biggest Lessons

I was having a drink with Greg Sheehan last week, the co-founder of RightWay, and we were chatting about what it takes to succeed in business. We agreed perhaps the most important thing, summed up in one word, is hunger.

Hunger is one of the most beautiful things to have, but hardest things to describe. It’s that burning fire inside you that constantly tells you that you can be the best in the world, and that nobody is going to step in your way. It’s the thing that keeps you going when if you looked at the situation logically, you would probably stop. It’s the thing that drives you when the credit card is maxed out.

I’ve put together a list of my 5 biggest lessons from starting and selling OOMPHER in my teens. Number 1 will help you build your hunger:

1. Work out your 30 year plan, and work backwards:

This is a gem of advice that Sir Michael Hill gave me. Even today, Sir Michael pulls out his life plan and looks at it every day. The secret is to get past the material objects, and think more aspirationally. What do you really, really, really want in life?

I sat down with a pen and a clear mind, and I worked it out. What I want is family, friends, fun, finances, fortune (good health/luck), influence, and above all, total freedom. The most aspirational level possible for me at the present time is to have total freedom across all aspects of my life, and to be able to help those people out who have helped me.

I literally close my eyes and imagine myself sitting on my private island, with all of my family, friends and mentors there, swimming, jet-skiing, building relationships and having the best time of their lives. It’s got to be totally aspirational.

2. Fix a painful problem in a specific market, and do a 4-step plan of idea validation:

Perhaps the most important thing I’ve learnt in business so far, and something I didn’t do with OOMPHER, is that the best way to guarantee your business is going to be a huge success is to really nail the solution to an unbelievably painful problem that people have within a specific industry. This should be the kind of problem that people wake up in the middle of the night sweating about. I have a four step plan of market validation that I learnt from one of my interviewees, Sam Ovens, that I now use when analysing any opportunity. This is particularly relevant for tech; it goes like this:

1. Number one: Find a painful problem in a specific industry, and remember, it doesn’t have to be sexy. Some of my friends here in Auckland are developing a startup called Boardingware which helps boarding schools better manage their students. I mean, boarding schools aren’t exactly riveting! But their solution solves a very painful problem for boarding school managers, in a very specific market.

2. Number two: So you think you’ve got an awesome idea? Good, firstly, don’t get too excited, as it probably won’t be. The number of times that I have gotten super excited about an idea only to find out that the market doesn’t actually want it, is crazy. So in a very level-headed and completely emotionless way, start talking to the market directly. Start door knocking. Talk to the potential customer. Ask them if they would pay for your product, get their advice and then develop your product and sales plan accordingly. If you’re in a sweet spot, pretty quickly you’ll have a viable product. Research, research, research.

3. Number three: I can’t stress this enough. If you have a product people want, make them commit to paying for it before you actually build it. Get your sales shoes on and literally get the prospective client to sign on the dotted line, saying that they will indeed pay for your product if it is as you’ve sold it once delivered.

4. Number four: Depending on the size of the sale, once you’ve got 12-20 confirmed sales, invest your or other investment resource into building the product. Remember, by this stage you 100% know that your product is a good idea, and there is no shortage of investment for good ideas, so don’t go giving away too much equity too early.

If you get through all of these 4 steps, presuming you work like a racehorse, you’ve almost guaranteed your success.

3. Invest… Even if you’ve got nothing to invest:

While I was building OOMPHER, there were times in 2014 when I literally ran out of cash flow.

One time in particular I was driving in Christchurch, and I ran out of fuel. I made it to the gas station but I only had $0.40c in my bank account. I rang Mum to see whether she would bail me out, and she didn’t answer. I ran my brother, no luck there either. I was literally sitting at a gas station in Riccarton, with all the hunger in the world, but no cash to my name; only negative balances on my credit card. I literally text a family friend and asked her if she would kindly lend me $20 through bank transfer.

In the end I got my $20 bucks, put some fuel in my car, got back to my house, and then used my remaining credit to book a trip to Auckland as I thought there might be a small chance that I could sign a new sponsor if I got up there and started selling my vision. I invested in the trip even though I literally had nothing to invest.

4. Don’t network, make friends

A few days ago I got back from the USA where I’ve been for the past 6 weeks, primarily in New York City. Over in the States I hung out with some absolutely mind-bogglingly amazing people such as Suzy Amis-Cameron, James Cameron, Josh Bayliss, Chris Liddell, Craig-Nevill Manning, Victoria Ransom, Jack Tame and Shazi Visram. Over my USA tour, all of these people were delighted to meet and chat business (check out my last column on for more information).

The point I’m trying to make by mentioning all of these incredible folks is that people always say to me, “Jake, you’re awesome at networking.” And I say, “no,” “no, I’m not,” “I don’t network.” “I hate networking.” “I just like to make friends.”

There is a massive difference in strategically trying to meet someone because of how they can help you, and meeting someone because you’re genuinely interested in them as a person.

I can’t stress this more clearly: all of the people I surround myself with are people who I am genuinely fascinated in as the individuals that they are.

5. Talk to the taxi driver

It was 2013 and I was the head boy at my boarding school (Adams House of Christchurch Boys’ High School). A few of us had been in Hamilton at a boarding schools conference, and it was time to fly back to Christchurch.

I was sitting in 1A and I was trying to put my headphones on before the person next to me could start a conversation. Anyway, as I’m about to put my headphones on, she goes: “How’s it going?” I remember wondering why I didn’t move faster.

The person next to me was a lady by the name of Erica Amon, who is the Area Manager of Healthcare of New Zealand in the Waikato region. Erica was a totally fascinating person and we discussed her investments, her love for golf and my latest business ideas. Despite our corresponding interests, we still had different focuses. But that didn’t matter. I was genuinely interested in Erica as a person, and she seemed genuinely interested in me as a person. Needless to say we talked for the whole flight and are very good friends today.

That night Erica added me as a friend LinkedIn and pretty soon after introduced me to her good friend, Shelley Campbell, the CEO of the Sir Peter Blake Trust. Shelley and I became good friends too.

Pretty soon after I met Shelley, she put me in touch with her good friend Keith Marshall, the recently appointed CEO of a Crown Entity… That very Crown Entity was called Careers New Zealand… And they ended up buying my business, OOMPHER.

If I had put my music on in 1A and not talked with Erica, there is an almost a 100% chance that things would be totally different today.

Never underestimate the power of making friends.

Want to expand your business to the U.S.? Read these 7 tips.
21 years. 21 things I have learnt.

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