Rowan Simpson wrote a post detailing the track record he’s seen over the seven or so years he’s been an active investor. For those who don’t know Rowan, he’s a TradeMe alumni and, because of the sheer size TradeMe exit, has significantly more money to spend on these deals than I do.

That said, investment isn’t so much about the quantum involved as it is about the percentage results obtained so, in answer to Rowan’s call for more investor transparency I decided to compile a similar list detailing my investments and how they’ve performed. Without any further ado then:

  • Cactus Outdoor – my first investment nearly 20 years ago and still going strong. Not making anyone rich but I credit it with giving me the skills and the freedom to do what I do now
  • Connect2Field – sold to US listed Fleetmatics
  • Cloudability
  • Appsecute – sold to North American company ActiveState
  • WIP videos
  • LearnKo
  • Publons
  • Cloud66
  • ClusterHQ
  • Credii
  • Tylr Mobile – Folded
  • Pasiv – missing in action at this stage
  • CommonLedger
  • Mindscape

The first investment, Cactus, wasn’t really one focused on return – it was more about skills, lifestyle, doing something good and building great product. For the purposes of a return on investment analysis it can be discounted.

Connect2Field was a great performer – I was an early investor and also on the board and part of the team that took it to its eventual exit. Details are obviously confidential but the return was around 7x and it alone made my portfolio profitable.

Cloudability was my first angel deal and I was one of the first couple of external investors. I’ve seen the company go on to get significant (8 figure US) venture funding and build a very successful business.

Appsecute was something of a disappointment, not so much because of the exit size but because it was a shame to sell mid-way through the project. But as part of a bigger team the Appsecute folks had a bigger stage to launch from – from a financial position the jury is out on how well the investment paid off for me.

WIP Videos, LearnKo and Publons were all in the 2013 Lighting Lab incubator cohort – they’re all still going and, despite a few initial setbacks, are all doing good things. I only invested in the initial round for all three – the fact I didn’t participate in follow on rounds has much more to do with me than it does with them.

Cloud66 was a fortuitous investment – I first came on as an adviser and later invested. The company is growing fast and looks like it has something of real value.

ClusterHQ was another early stage investment and I’ve had a ton of fun helping the company get to where it is today. Luke and his team have done an awesome job so far and look for some big news from them soon.

Credii is another company that I’m passionate about – democratizing industry analysis is a big problem, but a big opportunity and Credii is executing well so far.

Tylr Mobile was a great idea, and one whose time will eventually come. But it was perhaps a little early. Either way it is no longer.

Pasiv is one that I’m not so happy about. The best thing I can say is that it’s a perfect example of Rowan’s comments re startup founder communications with investors.

CommonLedger and Mindscape are two recent investments. CommonLedger has done perhaps the best job of all of my portfolio companies in terms of building a professional team. Their communication, seriousness, mutual respect and execution are amazing. Time will tell how well that converts into investment returns however. Mindscape is also executing really well – they have a massive international opportunity and I’m bullish about their chances.

On top of these investments, I hold a small stake in a number of companies as a formal adviser – Fileboard, MadeiraCloud, ActiveState and Learning Source are all still going. CloudImmunity and billFLO are dead.

Investing is less about financial returns for me than it is about having fun, being involved and giving entrepreneurs a hand to get going. Like Rowan I tend to have a fairly hand-on role with the companies I invest in – I’m in the process of finalizing another couple of investments, both of which I will have significant involvement with either as a director or adviser.

So there you have it – the low down on my investment history. It’s been a fun few years!

Post script – In an indication of some of the structural issues that indicate the problem with the New Zealand economy, I have to add that I’ve made significantly more money out of property than I ever have with investing in businesses. Unfortunately the decades of property prices spiraling ever upwards have meant that investment in land and building has been the most attractive option for many.

Post post script – As I said in the introduction, the money I’ve invested has paled in comparison to that invested by more cashed-up investors. That said, and just for clarification, I’ve invested around $500,000 across the entire portfolio.

Ben Kepes

Ben Kepes is a technology evangelist, an investor, a commentator and a business adviser. Ben covers the convergence of technology, mobile, ubiquity and agility, all enabled by the Cloud. His areas of interest extend to enterprise software, software integration, financial/accounting software, platforms and infrastructure as well as articulating technology simply for everyday users.


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