My VC journey: Lessons learnt in the trenches of investment and operations

My career has been a journey shaped by bold decisions, unexpected opportunities, and big failures - serving up invaluable lessons learned in the trenches of investment, operations, and leadership. 

Over time, I developed a unique perspective on capital allocation, human capital management, business growth, and governance - one that serves me well in the richly layered world of venture capital (VC).

Entrepreneurial beginnings

The foundation of my career in VC was laid in high school when I co-founded an investment partnership in 2003. With capital from friends, family, and anyone daring enough to trust high school kids, we navigated the public markets with surprising success. 

Seven years later, we had achieved a compound annual growth rate of over 30%. This early experience not only taught me about the responsibility of managing other people’s money but also how to identify excellent investment opportunities. 

I developed a long-term mindset and learned the importance of prioritising sustainable growth over short-term gains. My exposure to public markets at such a young age gave me a keen understanding of investor expectations, performance measurement, and transparent reporting.

Inspired by the dynamics of horse racing, our strategy was built on four key principles.

• The horse (The company) - Identifying businesses with the right fundamentals and an enduring competitive advantage that compounds value over time.

• The jockey (The CEO) - Backing leadership teams that are open to strategic input and prioritise a strong company culture and thriving employees.

• The track (The market) - Ensuring a large enough target audience with ample opportunities for market players of all sizes. Even if the company doesn’t dominate, capturing just a fraction of the market would still be significant.

• Price discipline - Understanding that investment returns are determined at the point of entry, not exit. Through experience, we learned that maintaining a disciplined approach to valuation - paying the right price and ensuring a margin of safety - was critical to achieving strong returns without the need to chase them.

Embracing a global perspective

Determined to raise capital in one of the world’s most competitive financial markets, we took our partnership to New York in 2010. Despite visa issues and grappling with the cultural nuances of American investors, we managed to secure significant funding from a family office. 

The experience taught me resilience in a city that takes no prisoners. The sting of hearing ‘no’ over and over again taught me more than dealing with rejection - it laid the foundations for learning the art of negotiation. I got to know a lot about financial structuring and the critical importance of strategically aligning with investors. 

By establishing an onshore structure in Delaware and managing capital across borders into South African equity markets, I gained deep insights into international finance as well as compliance and governance. 

My exposure in New York helped me cultivate a global perspective, which is hugely instrumental in helping startups understand and navigate raising capital across different geographies and cultures in my current role at HAVAÍC.

Mastering strategic leadership

In 2016, I became one of the youngest non-executive board members of multiple JSE-listed companies. 

Subsequently, I moved from a passive shareholder to an active investor in one of these businesses. The role was a baptism of fire, but I wasted no time identifying gaps in the company’s business model and governance structures. 

After negotiating debt restructuring and stepping into the role of interim CEO, I was tasked with turning around a struggling business that held the master franchise licenses for international brands like Domino’s Pizza and Starbucks in South Africa. Exposure to these global brands at the threshold of their digital transformation journeys whetted my appetite for the world of tech startups. 

The role was an intense learning experience in managing internal stakeholders. Working with people - many older and more experienced than myself - requires an entirely different set of skills from financial modelling or strategy execution. 

I learnt how to lead teams, make difficult personnel decisions, and align diverse interests to drive performance. Each mistake I made reinforced a critical truth: financial and operational success is ultimately driven by people.

The experience set me up for my next role as COO of an insurance company. It also prepared me for a subsequent restructuring due to regulatory hurdles and financial constraints. But this time, I approached it with a renewed focus on culture, team dynamics, and adopting startup technology to work smarter and maximise resources.

Instead of cutting costs, I created a lean, high-performance team that embraced the challenge ahead. The result was a cultural revolution. Despite not being able to ultimately save the business, operationally we built a team that was more engaged, more accountable, and ultimately more effective. The transformation proved that people's performance precedes operational performance, which precedes financial performance - wise words from a mentor and CEO of a blue-chip, JSE-listed company. 

This belief is central to how we support our portfolio companies at HAVAÍC. Startups don’t just need capital, they need leaders who can build strong teams, foster the right culture, and create environments where people can perform at their best. 

Returning to my roots

Eventually, I returned to my roots in capital allocation - this time with a nuanced operational perspective. My journey from an investor to an executive operator gave me a unique vantage point: I now understand both the capital allocator's requirements and the operational challenges that startups face.

It is a journey of continuous learning and adaptation that has equipped me with a diverse arsenal of skills, including raising capital across different stages and global markets, navigating business challenges, building a culture of accountability, making decisions at the board level, leading strategically, and leveraging technology to drive growth and efficiency. 

At HAVAÍC, we bring these complementary skills together to offer startups not just capital but strategic partnership, operational guidance, and international networks. For limited partners (LPs), we provide trusted governance, a strong track record, and a focus on impactful investments that drive sustainable returns.

My journey reflects this ethos. By leveraging my experience, I am committed to helping startups navigate growth challenges and delivering sustainable value to our LPs.

About Tyrone Moodley

Ty is a curious self-starter motivated by problem-solving. He co-founded an investment partnership in his teens and went on to become a partner of a South African-focused, US-based investment fund and one of the youngest directors on the Johannesburg Stock Exchange. 

In 2016, Ty was recognised as one of the 30 Most Promising Entrepreneurs in Africa under 30 by Forbes. His skills add a strategic, operational, and entrepreneurial lens to the team and portfolio companies. This compliments his focus areas within HAVAÍC, which includes investment origination, post investment management and support, and creating realisations and exits across our portfolio.