Raising capital isn’t just about having the right numbers—it’s about aligning your story with how investors think. Behind every funding decision is a mix of mental models, market assumptions, and personal judgement.
In this Growth Spotlight episode, we interviewed Akash Maharaj, an investor and advisor with over 25 years of experience spanning structured finance, equity investments, and venture capital. Originally from South Africa, Akash built and led VC investment teams within major banks, working across multiple regions and sectors. He’s evaluated early-stage ventures, structured complex deals, and presented to high-stakes committees—often under pressure to justify decisions in uncertain conditions.
Now based in the Netherlands, Akash works closely with startup teams—mainly in Africa, but increasingly in Europe—helping founders shape their capital-raising strategy and communicate more effectively with investors. With experience on both sides of the table, he offers founders a clear understanding of how investment decisions are really made.
In this conversation, Akash shared the mental frameworks he uses to evaluate startups, how he weighs risk and reward, why biases matter in VC, and how intuition plays a bigger role than most people think.
Before evaluating traction or pitch decks, experienced investors apply specific mental frameworks to judge a startup’s potential. These frameworks aren’t just theoretical—they shape how an investor interprets risk, growth, and long-term success.
Yagmur: What are the key mental models or frameworks that guide your investment decisions?
Akash:
Akash explained that first principles thinking is central to how he evaluates startups. Rather than relying on what’s worked before, he breaks down problems to their core elements and reconstructs them from the ground up, especially in unfamiliar or rapidly evolving markets.
He also emphasised the power of network effects, particularly in platform businesses where each additional user increases the value of the product. For him, it’s not just about user acquisition—it’s about how each user contributes to long-term defensibility.
Another important lens is market power and moats—barriers to entry and the ability to scale sustainably. Akash also applies second-order thinking, evaluating not only what will happen next, but what could happen after that.
Investors don’t all view risk the same way. Their expectations are shaped by the size of their fund, the markets they operate in, and even personal experience. Understanding this context is critical for founders trying to raise capital.
Yagmur: How do you balance risk and reward when evaluating a potential investment?
Akash:
According to Akash, risk-reward profiles vary widely, and one of the most common founder mistakes is assuming all investors are looking for the same outcomes. For early-stage investors, high risk is acceptable—but only if the upside is compelling.
One of the most important factors he considers is portfolio fit. It’s not just about whether a business is investable—it’s about how it complements the rest of the portfolio. A great founder with the wrong profile for that fund might still be passed over.
He also stressed the importance of downside protection—unit economics, realistic paths to cash flow, and clarity around how capital will be used. Beyond the numbers, founders should demonstrate an awareness of the macro environment and how their business aligns (or thrives) within it.
While venture capital is often presented as rational and data-driven, it’s still driven by people, and people carry biases. Recognising these patterns can help founders position themselves more effectively.
Yagmur: Investors often have natural biases when evaluating investments. How can founders approach these and seek to overcome them?
Akash:
One of the most common biases Akash highlighted is pattern matching—investors gravitating toward startups that resemble past successes. If a business looks unfamiliar, it may require more effort to build conviction.
He also noted confirmation bias, where investors subconsciously seek data that reinforces their first impression, and short-term thinking, where a lack of early traction may be interpreted as a lack of potential.
To counter this, Akash encourages founders to do their homework. Understanding not just the fund thesis but the individual investor’s worldview, portfolio, and public presence is key. Founders should speak to others who’ve pitched the same investor and tailor their narrative accordingly, because you’re not pitching to a firm, you’re pitching to a person.
Startups are long games. And for investors like Akash, deciding whether to get involved means looking beyond metrics and forecasts—it means evaluating the founder’s capacity to grow alongside the business.
Yagmur: How do you assess the long-term potential of a startup before investing?
Akash:
Akash often notes that investor-founder relationships can last longer than some marriages. That’s why he places strong emphasis on the founder’s qualities. Beyond the model and metrics, he looks at founder–market fit, long-term vision, and the ability to execute on that vision.
He also considers resilience and adaptability—how a founder handles feedback, navigates challenges, and leads through uncertainty. For Akash, it’s not about being perfect, but about showing the ability to learn, adjust, and keep leading when things go wrong.
Product differentiation and scalability still matter, but the human side of the business is often the clearest indicator of long-term success.
While many investors rely on models and metrics, some of the most important decisions come down to instinct. For Akash, intuition isn’t mystical—it’s something learned through experience. In fact, it’s often what prevents him from making the wrong move.
Even with all the data and strategy in place, some investment decisions are guided by something harder to define—and for Akash, intuition is one of the most powerful tools an investor can develop.
Yagmur: What role does intuition play in investing, and how do you refine it over time?
Akash:
Akash described intuition as an internal compass, shaped by experience, but most valuable when navigating uncertainty. While experience helps make sense of known variables, intuition helps investors deal with unknowns.
He shared that some of his most important decisions came from walking away from deals at the last moment—not because the numbers didn’t add up, but because something didn’t feel right. Over time, he’s learned to trust those instincts.
He encourages both founders and investors to create space for reflection—quiet moments where gut instinct can rise above the noise and help guide better decisions.
Akash Maharaj brings clarity to a process that often feels opaque. Through thoughtful reflection and decades of experience, he shows that investing isn’t just about spreadsheets—it’s about signals, storylines, and the people behind them.
This conversation pulled back the curtain on how investors really think. From analytical models to personal instinct, funding decisions are rarely black and white, and founders who understand that are far better positioned to secure the right support.
Stay tuned for our next Growth Spotlight episode, where we continue sharing real-world insights from experts!
