The FM chats to Gladwyn Leeuw, CEO of E Squared Investments
16 January 2025 - 05:00
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Understand that the biggest risk in early-stage investing is founder risk. People drive products and services, thus it’s essential to assess what makes the founders and leadership teams uniquely equipped to solve the problem at hand. I often ask three specific questions: Are you obsessed with the problem you are solving or merely with the product you’ve created?; How sustainable is your motivation?; What makes you the best team to exploit the opportunity?
What was your first job?
I worked part-time in clothing retail for Mr Price between completing matric and starting university.
How much was your first pay cheque, and how did you spend it?
For the temp retail work I was paid about R14 per hour, but my first official pay cheque as a business analyst intern at Deloitte was for R6,000. I spent it on fuel, airtime and data, savings, food and social outings with my girlfriend and other friends, and it surprisingly went a long way.
What is the one thing you wish somebody had told you when you were starting out?
Don’t live beyond your means or overextend your finances, whether in your personal life or in business. As US personality Dave Ramsey says: “We buy things we don’t need with money we don’t have to impress people we don’t like.” There is significant reward in practising delayed gratification.
If you could fix only one thing in South Africa, what would it be?
I would revamp the education system to create an irrefutable talent advantage, using the African demographic dividend. A robust education system fosters critical thinking, technical skills and entrepreneurial training, empowering young South Africans. By investing in education, we can reduce inequality, drive innovation and transform South Africa into a knowledge-based economy, fostering sustainable development and social progress.
What’s the most interesting thing about you that people don’t know?
I initially aspired to be a professional rugby player, with finance and investment as my fallback plan.
What’s the worst investment mistake you’ve made?
It was investing in something I didn’t fully understand — simply that it was popular and endorsed by prominent investors. As the saying goes: “If you can’t explain it simply, you don’t understand it well enough.”
What’s the best investment you’ve ever made? And how much of it was due to luck?
It was an investment in South Africa’s leading on-demand grocery delivery service in December 2019. The onset of Covid in March 2020 led to exponential growth, resulting in a successful exit to an African retail and wholesale group in 2021 at a five times return on our initial capital.
What’s the best book you’ve read recently and why did you like it?
Ikigai: The Japanese Secret to a Long and Happy Life by Francesc Miralles and Héctor García. It explores finding your purpose through the lens of the world’s longest-living people. The book shows how aligning what you love, what you are good at, what the world needs, and what you can be paid for can lead to a fulfilling life. I appreciate how it challenges conventional notions of success and encourages meaningful, sustainable practices for business leaders, enhancing employee engagement and balancing professional ambitions with personal wellbeing.
What’s the hardest life lesson you’ve learnt?
As a young leader in the high-stakes world of venture capital and private equity, the hardest life lesson I’ve learnt centres on impostor syndrome and the relentless drive that led me to the brink of exhaustion and burnout. In the pursuit of proving my worth and capabilities, I pushed myself beyond my limits. This resulted in severe physical and mental health consequences.
I learnt that leadership is about sustainable performance, resilience and fostering a supportive environment where delegation and collaboration are paramount to collective success and progress.
What phrase or bit of jargon irks you most?
“I’ll sleep when I’m dead.” This phrase glorifies overwork, neglecting the importance of rest and recovery. True success lies in balancing ambition with self-care.
What is something you would go back and tell your younger self that would impress them?
“You will achieve more than you think possible.” Reflecting on my journey, I would impress upon my younger self that stepping outside my comfort zone and embracing challenges would unlock opportunities I never imagined.
If you were President Cyril Ramaphosa, what would you change, or do, tomorrow?
I would address the exchange controls and intellectual property (IP) ownership restrictions. The Reserve Bank’s stringent exchange controls complicate foreign direct investments, loans and the repatriation of capital. Moreover, IP ownership restrictions often push founders to register their IP abroad, where they find more robust legal frameworks and protections. By reforming these regulations, we can boost investor confidence, facilitate access to venture capital and support South African start-ups in global markets.
Support our award-winning journalism. The Premium package (digital only) is R30 for the first month and thereafter you pay R129 p/m now ad-free for all subscribers.
BACKSTORY: Gladwyn Leeuw of E Squared Investments
The FM chats to Gladwyn Leeuw, CEO of E Squared Investments
What’s your one top tip for doing a deal?
Understand that the biggest risk in early-stage investing is founder risk. People drive products and services, thus it’s essential to assess what makes the founders and leadership teams uniquely equipped to solve the problem at hand. I often ask three specific questions: Are you obsessed with the problem you are solving or merely with the product you’ve created?; How sustainable is your motivation?; What makes you the best team to exploit the opportunity?
What was your first job?
I worked part-time in clothing retail for Mr Price between completing matric and starting university.
How much was your first pay cheque, and how did you spend it?
For the temp retail work I was paid about R14 per hour, but my first official pay cheque as a business analyst intern at Deloitte was for R6,000. I spent it on fuel, airtime and data, savings, food and social outings with my girlfriend and other friends, and it surprisingly went a long way.
What is the one thing you wish somebody had told you when you were starting out?
Don’t live beyond your means or overextend your finances, whether in your personal life or in business. As US personality Dave Ramsey says: “We buy things we don’t need with money we don’t have to impress people we don’t like.” There is significant reward in practising delayed gratification.
If you could fix only one thing in South Africa, what would it be?
I would revamp the education system to create an irrefutable talent advantage, using the African demographic dividend. A robust education system fosters critical thinking, technical skills and entrepreneurial training, empowering young South Africans. By investing in education, we can reduce inequality, drive innovation and transform South Africa into a knowledge-based economy, fostering sustainable development and social progress.
What’s the most interesting thing about you that people don’t know?
I initially aspired to be a professional rugby player, with finance and investment as my fallback plan.
What’s the worst investment mistake you’ve made?
It was investing in something I didn’t fully understand — simply that it was popular and endorsed by prominent investors. As the saying goes: “If you can’t explain it simply, you don’t understand it well enough.”
What’s the best investment you’ve ever made? And how much of it was due to luck?
It was an investment in South Africa’s leading on-demand grocery delivery service in December 2019. The onset of Covid in March 2020 led to exponential growth, resulting in a successful exit to an African retail and wholesale group in 2021 at a five times return on our initial capital.
What’s the best book you’ve read recently and why did you like it?
Ikigai: The Japanese Secret to a Long and Happy Life by Francesc Miralles and Héctor García. It explores finding your purpose through the lens of the world’s longest-living people. The book shows how aligning what you love, what you are good at, what the world needs, and what you can be paid for can lead to a fulfilling life. I appreciate how it challenges conventional notions of success and encourages meaningful, sustainable practices for business leaders, enhancing employee engagement and balancing professional ambitions with personal wellbeing.
What’s the hardest life lesson you’ve learnt?
As a young leader in the high-stakes world of venture capital and private equity, the hardest life lesson I’ve learnt centres on impostor syndrome and the relentless drive that led me to the brink of exhaustion and burnout. In the pursuit of proving my worth and capabilities, I pushed myself beyond my limits. This resulted in severe physical and mental health consequences.
I learnt that leadership is about sustainable performance, resilience and fostering a supportive environment where delegation and collaboration are paramount to collective success and progress.
What phrase or bit of jargon irks you most?
“I’ll sleep when I’m dead.” This phrase glorifies overwork, neglecting the importance of rest and recovery. True success lies in balancing ambition with self-care.
What is something you would go back and tell your younger self that would impress them?
“You will achieve more than you think possible.” Reflecting on my journey, I would impress upon my younger self that stepping outside my comfort zone and embracing challenges would unlock opportunities I never imagined.
If you were President Cyril Ramaphosa, what would you change, or do, tomorrow?
I would address the exchange controls and intellectual property (IP) ownership restrictions. The Reserve Bank’s stringent exchange controls complicate foreign direct investments, loans and the repatriation of capital. Moreover, IP ownership restrictions often push founders to register their IP abroad, where they find more robust legal frameworks and protections. By reforming these regulations, we can boost investor confidence, facilitate access to venture capital and support South African start-ups in global markets.
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