Stories from Sherpa Fellows: Hear about Tiffany and Nanthini’s Experiences!

Jordan Wolken
Sherpa Ventures
Published in
7 min readDec 9, 2021

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Before the year comes to a close, we spoke with Sherpa Investment Associate Fellows Nanthini Kumarajan and Tiffany Monthe-Siewe about their backgrounds, experience working with Sherpa, and tips for breaking into the African VC space. Nanthini and Tiffany joined us in May and were part of the first batch of fellows to join the team. They are both MBA students at The Wharton School and are also pursing a joint MA degree in International Studies at the Lauder Institute.

***Want to hear from Nanthini and Tiffany directly and learn more about the Sherpa Fellowship? Register for our Sherpa Fellows Webinar in January here! https://forms.gle/6aSGoLoNm9b6LEeX9***

Could you share a little bit about your background and what you were doing before working at Sherpa?

Nanthini: I grew up in Singapore, studied at Oxford for my undergrad and then started my career in consulting at McKinsey in London. Later, I really wanted to get more experience working on the ground in Africa, so I worked at M-KOPA in Kampala for one and a half years before starting business school at Wharton.

Tiffany: I grew up in Cameroon and have a corporate finance background. I studied finance at Carnegie Mellon for my undergrad and then worked at JP Morgan for two years. Afterwards, I spent two years at Twitter before now pursuing my MBA with an intended concentration in entrepreneurship and innovation.

How do you feel like those experiences helped prepare you for working with Sherpa?

Nanthini: I think working for McKinsey helped to build my strategic thinking and analytical skills. So, that's helped me evaluate companies in a structured way. It also obviously taught me the core skills in PowerPoint to make and evaluate decks, as well as strengthen my skills in Excel, which I use to look at the financial models that companies send during the Sherpa due diligence process. And then working for M-KOPA helped me understand the operational challenges on the ground, which made me have a much better understanding of the context that African startups are operating in. As a result, I’m now able to foresee some potential challenges startups may face, as well as which parts of their go-to-market strategy or big plans could be a bit more tricky to achieve.

Tiffany: My current focus has been about being a good communicator, be it with the rest of the Sherpa team or with the founders, and being very objective as well. Because we have so much information from so many different parts of the continent – there are 54 countries at the end of the day – not trying to put one thing, or one person, or one venture, or one problem in a box has been fundamental. That mindset, I think, has come from my experience at Twitter, which was a very open-minded space and company culture. They really encouraged everybody to just bring their true self to the office, and so that has manifested as more of a qualitative, personal trait that has brought more value to my experience.

Nanthini (left) and Tiffany (right) posing with their Sherpa team hoodies

What is your role at Sherpa, and what types of tasks have you worked on?

Nanthini: I've done two main things at Sherpa. One has been helping to carry out due diligence on companies that we already have significant interest in. I've done that with three companies now, which is cool. Those included Money254 and then Payhippo, as well as HustleSasa. I reviewed all their documents, their pitch deck and their financial models, and then I had calls with the founders before preparing the materials to take to the Sherpa Investment Committee – and then I’ve also gotten the opportunity to present in the Investment Committee, as well. So, that's been one core thing that I've done.

The second thing has been reviewing the “open call” applications from startup founders that come through our website and presenting them in our weekly open call review meetings. It’s been fun to identify interesting startups that we might want to look into further.

I think a couple of things that I might get to work on more are doing some market analysis, potentially developing an investment thesis in a particular sector, and providing support to portfolio companies.

Tiffany: Open call has been a major part of my time at Sherpa, by which we are reviewing all the applications for funding that have come in from founders, and driving the conversations that we, Sherpa, have as a team about them. This entails reviewing applications, filtering some, understanding which are the most compelling, bringing those to the table, and answering any questions that the greater team may have. Despite how time-consuming the task can be, our goal is to remain active within the entrepreneurship space on the continent, and to ensure that we don’t miss a great venture out there that would be a good fit for our portfolio.

Another task of mine is what I would call portfolio diagnosis. This entails communicating with all founders of our portfolio companies and understanding how the last 12 to 24 months have been for them, as well as what is next to come. My task is to identify any recent challenges they’ve gone through and see how Sherpa can be a source of support.

How has your experience with Sherpa been thus far?

Nanthini: I’ve had an amazing time at Sherpa. It’s been great to get exposure to early-stage startups on the continent and get involved with investing in them! I've especially enjoyed being able to attend the Investment Committee meetings. The Sherpa Investment Committee is really cool – it’s made up of a lot of former founders who are very interesting people. I've really enjoyed seeing how they think about companies, what feedback they give, etc. That's been a great experience as I start to think about a career in VC in Africa.

Tiffany: The experience with Sherpa has been phenomenal. It's allowed me to discover a new sector in which I now know I can thrive. Today, I am actually considering a career in venture capital post-MBA. I am incredibly grateful for this opportunity that the Sherpa team allowed me to experience.

Do you have any tips for people looking to break into African VC or another startup-related job on the continent?

Nanthini: I’m not sure if I’m the best person to share tips, but my main suggestion would be to just try and look out for opportunities. The Sherpa Fellowship is a great one, and then there might be other opportunities too. Reach out to VCs and offer to work part time, especially if you're in school, since I think VCs might be open to that. It's that practical experience that really helps. Adjacently, I think being aware of what's going on in the tech space, especially in Africa, is helpful. So, yeah, following the latest news on that stuff, and then also just having your own interests that you become knowledgeable about can be helpful as well.

To answer the question in a more structured way, I'd say there are three key areas to work on: skills, knowledge or experience, and then network and exposure. On the skills piece, I think it's primarily just being able to think in a structured and analytical way, both in terms of qualitative and quantitative analysis. Then it helps to also be proficient in PowerPoint and Excel, of course. Then on the knowledge side, it's more about just keeping track of what's going on in the VC industry in general, and then maybe a couple of sectors that you're interested in. And even having on-the-ground experience working at a startup helps. Then the last part about your network is just about knowing people who are doing cool stuff, basically.

Tiffany: I would say, be curious and talk to people. Especially those who already have some professional experience on the continent. That is exactly how I ended here.

For example, our very own Aaron! If you reach out to someone like him for help, he will go out of his way to support you, let it be through advice, introductions, and more. That’s why I think it is important to clearly communicate your goals and desires to people in your network, in your circles, whatever it is. And I feel like the VC space in Africa, particularly, is a very friendly community where people just want to help others.

In terms of important skills to develop, I would say that analysis is a big one. Analysis and synthesis where you are able to take in a lot of information and synthesize it into a digestible format for people of different backgrounds. That would be a major one.

A final piece of advice that a Wharton alumni once shared with me is to develop master the in’s and out’s of one industry. If you can be an expert in one sector, you will have valuable insight to share and you will gain a lot of credibility. And when your industry comes up in any meeting or any founder conversation, you are the owner.

Nanthini and Tiffany with Aaron Fu, Sherpa General Partner, in Philadelphia earlier this year

More information about the Sherpa Fellowship positions can be found on our website. For those looking to join the Sherpa team, we review applications on a rolling basis. If you think you have the chops to make a difference in the African startup community, no matter your background, we’d love to hear from you.

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Jordan Wolken
Sherpa Ventures

Sherpa Ventures | Bridges for Enterprise | Empowering startups in emerging markets