Switching sides – the entrepreneurs who became investors, and some who went back again


Emilian Popa started as an entrepreneur, building Groupon South Africa in 2010, before working with Rocket Internet in Asia, India, Russia, South Africa and Nigeria, and building further ventures in South Africa with Naspers’ funding.

He then followed a tried and tested path, becoming an investor himself, working for VC firm DiGAME for four years before returning to entrepreneurship with current venture Ilara Health. Popa is by no means alone in taking a journey like this, but he believes there are lessons to be learned from entrepreneurship that inform investment, and vice versa.

“Being an entrepreneur helps tremendously in making the right decisions when investing in entrepreneurs – identifying the right entrepreneurs, the right ventures and helping those ventures to grow. As an entrepreneur, I have been able to see what works, and what doesn’t work. I’m able to understand business models and operations, and can identify where the issues are and apply this knowledge and experience to investing,” he said.

“I’ve learned that building a successful venture is very much about the team and execution. Finding the right people, growing them and empowering them is key in the success of the venture, alongside flawless execution and being extremely driven. Having a deep passion for what you are building, being able to translate a market need into a product which can fulfill this need, being able to monetise that product, are just a few other key success factors in building a venture.” 

Having been there a few times, learning these lessons and both failing and succeeding, helped Popa immensely when he started to invest in peer entrepreneurs.

“On the other hand, having the investor mindset, the governance experience, and the connections in the venture capital world helps a lot when raising money for a venture and structuring it for growth,” he said.

Popa’s path is similar to that of Yele Bademosi, who also started out in entrepreneurship before moving into the world of VC, and then going back again. But Bademosi believes he has always been an entrepreneur. 

“My first venture into tech was starting a venture in the UK, which wasn’t successful, and with Microtraction although it wasn’t a venture-backed company it was still really about building something new,” he said. 

“Entrepreneurship for me has always been something that I’m really passionate about. I like the idea of coming up with solutions to problems and figuring out how to create value. I can’t say I was always going to go back to entrepreneurship, but what really drove that transition was the belief in the vision of what I’m trying to do with Bundle.”

Bademosi believes he has improved as both an entrepreneur and an investor from experiencing life on the other side of the table.

“They have definitely informed and sharpened each other in their own way. From an entrepreneur perspective I think being a VC really allows you to understand what “venture-scalable” means, and really understand what investors think when it comes to fundraising. And being able to think very holistically about markets. As an investor you need to be very good with macro factors that can affect the success of the business, and how you think about your go-to-market strategy, your product strategy, revenue strategy… And that has really helped me think about day zero to 100,” he said.

Dotun Olowoporoku exited his startup in 2015, and has since moved into the world of investment with Novastar Ventures. He says key to it all is empathy. 

“Being an ex- founder enables me to identify better and appreciate the struggles and personal challenges startup founders go through, especially in challenging environments. I can see myself in many of the founders I meet, which shapes how I give them feedback, even when it’s not favourable,” he said. 

“Empathy is quite critical in an investor-entrepreneur relationship, especially given that the relationship dynamics will change over time.” 

Bademosi shares this view.

“On the investor side it has made me realise how difficult it is to build venture scalable businesses, and the quality of the entrepreneur and the team, and how different Nigeria, and I guess Africa, is. You realise how fragmented the digital infrastructure is, and just how much we need to do. Even things like user education and customer support. So I am definitely grateful to have had the experience to see it on both sides of the table.”

Justin Stanford, who was an entrepreneur before moving into investing with 4Di Capital, also cites empathy as a key benefit of having experienced life in the trenches.

“I am able to truly understand and appreciate the position of an entrepreneur, and what it’s like to fight those battles. This empathy makes for the easier establishment of a genuine partnership-like relationship with an entrepreneur, as well as assisting in fostering mutual respect and credibility. It helps when you have done it before, and you can talk the same language from a place of experience, with a real grasp of the challenges being weighed and the agility required. I believe that it also engenders for us a reputation as founder friendly investors who “get it”,” he said.

“Furthermore, it enables you to offer practical advice based on your own experiences of what works and what doesn’t. When assessing opportunities, it also helps me to see through questionable claims or perhaps identify the less obvious challenges that might present themselves down the road.”

However, though there are overlaps, Stanford says the requirements for life as an entrepreneur and life as an investor are very different.

“As an entrepreneur, you think that you know all that’s needed to be an investor,” he said. “But that couldn’t be further from the truth. It’s really a completely different, standalone discipline with a whole learning curve of its own.”

So what are those key differences? Popa says the key one is that, as an entrepreneur, one needs to focus exclusively on the venture in order to succeed. 

“It’s all about the execution. As an investor, one needs to look at many opportunities to find the right ones; this involves a lot of networking, market research, and attending conferences to see what’s out there. As an investor, I was traveling 4 times a month. Now, I stay put and focus on building Ilara Health,” he said. 

“Sometimes I miss being “everywhere always”, as someone once put it some time ago, but I always tell myself that focus is key to success. Anytime I need to step away, for example to travel or do anything else not directly related to executing, I rethink 10 times and ask myself “do I really need to do this?”, to ensure it does not stop me from focusing exclusively on the venture.” 

Bademosi agrees on the different focuses of investors and entrepreneurs.

“As an investor you have a wide berth of things you are focused on. You are working with various entrepreneurs, your LP relationships, and even when you are working with a company you are still in an advisory or strategic role. You are not the one that is slogging day to day, working on a single idea,” he said. 

“That variability and being able to move from project to project is quite different. As an entrepreneur you are only focused on one thing, and you don’t have a lot of optionality.”

So do entrepreneurs make better investors? Not necessarily, says Popa, but he thinks having experience as an entrepreneur does help a lot. 

“At least it has helped tremendously in my VC career and as I continue to invest as an angel. Most of the ventures I invested in as a VC investor came from my close or larger network or entrepreneurs in the markets where I had already built entrepreneurial ventures. I not only knew the founders directly, but I was able to learn more about them from my network, and follow those companies for years before making an investment,” he said. 

“I still remember what an entrepreneur told me once about the investors she was meeting, who came dressed in a suit and tie. She said: “they don’t speak the same language as me, they don’t come from the same world”. I feel privileged for having experienced both worlds and being able to adapt to different cultures and situations – I would not have been able to be as effective in my role as investor, nor in my current role, without experiencing both sides.”

Bademosi believes experience in entrepreneurship is not a guarantee of success, as there are entrepreneurs that do not make good VCs, but agrees with Popa that it can certainly help.

“When you do have that intersection of a good entrepreneur and a good VC then it is a win-win situation,” he said.

But which job is harder? Popa has the last word.

“I find starting and building a business, and making it work, much harder and riskier than investing. I worked very hard as a VC investor, and I continue to invest small tickets in startups, to stay connected and be part of the game, but not to the level of mental and physical stress I’ve experienced while building ventures.”


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Passionate about the vibrant tech startups scene in Africa, Tom can usually be found sniffing out the continent's most exciting new companies and entrepreneurs, funding rounds and any other developments within the growing ecosystem.

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