Investor Talk: What were your best and worst investments?


Most of us wonder just how successful each investor is. Most of us are curious about the highs and lows of an investor’s portfolio. What have their best decisions been? What do they regret? In this episode of Investor Talk, Disrupt Africa asks four investors to let us in on their best and worst investments.

Justin Stanford, co-founder and managing director of 4Di Capital:

“My most challenging investments have been:

  • Where I don’t understand the industry or space deeply enough;
  • Where I have incorrectly or insufficiently assessed the founders / jockeys;
  • Where market timing has been sub-optimal for the product offering.

My best have typically been when there is an excellent founder / jockey team. This seems to have the highest correlation with success. Also, good timing for the intersection of market readiness with the product offering is important.”

Permjot Valia, founder of MentorCamp:

“Best investments – probably ones I have done myself – where I have invested in my own idea or business (MentorCamp and Flight and Partners being good examples) other investments that worked out well for me were EUPhotonics – it floated within two years of me investing and a restaurant chain called Tortilla.

They were good for different reasons. I was a consultant to EU Photonics – so knew the business had the potential to do very well. I had real knowledge of the pipeline etc. And I was just very, very impressed with the CEO running Tortilla – very bright – young guy – who totally understood the metrics driving his business.

My worst ones – way too many to mention – but there was one – where what we were doing was against the law! Another which I was an idiot for investing in as there were simply no controls in place.”

Sean Obedih, founder of NewGenAngels:

“To be honest we have only started this journey properly in the last 12 months but I have done personal deals,having said that the average angel investment is around 7-10 years and some people have held their investment for longer, so this is a long term game.

Without mentioning any names in particular, my worst investments have been the ones I did without knowing the team dynamics too well. Every startup has it’s own ups and downs, the ones that usually make it are the ones led by hardcore founders. Using a football analogy, some founders play like amateurs in a Sunday league while others are professional who aspire to be nothing but the best and want to stay in the premier league.

The most successful have been the ones that are eager to learn and aren’t afraid to try new things because they always find a way to learn more from failed experiments and their sole focus is to delight their users.”

Bunmi Akinyemiju, chief executive officer of Venture Garden Group:

“VGG, as an investor in early-stage startups, is still relatively young. We go in for the long term, so it’s a little too early to definitively assess the performance of our portfolio. We invest in highly-talented teams though, and doing that ensures that we can create value with every one of our investments from day one, even outside of the standard business metrics.”


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Inspired and excited by the African tech entrepreneurial scene, Gabriella spends her time travelling around the continent to report on the most innovative tech startups, the most active investors, and the latest trends emerging in the ecosystem.

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