TORONTO — A new book by Canadian investor Henry Fiorillo is taking aim at the growing hype surrounding startup investing, offering a candid look at the risks and realities behind angel investing.
In Fool’s Gold: Angel Investing and the Fine Art of Losing Money, released on May 19, 2026, Fiorillo draws on six decades of experience to examine why many early-stage investments fail — and what investors often overlook in the pursuit of high-growth opportunities.
The book positions itself as a counterpoint to the success-driven narratives that dominate startup culture, focusing instead on the financial and psychological pitfalls that can lead to losses.
A growing but high-risk investment landscape
Angel investing — the practice of investing personal capital into early-stage startups in exchange for equity — has become increasingly accessible in recent years. The rise of social media, online investment platforms, and startup ecosystems has broadened participation, but also amplified risk.
According to the book’s premise, the widespread pursuit of high-return opportunities has led to an environment where hype, fear of missing out (FOMO), and polished presentations can overshadow due diligence.
Fiorillo argues that this dynamic has contributed to a pattern in which many investors underestimate the likelihood of loss.
Lessons from decades of investing experience
Drawing on thousands of investment evaluations over his career, Fiorillo outlines key factors that can influence investment outcomes, including behavioural biases, founder assessment, and decision-making frameworks.
The book emphasizes the role of cognitive bias in investment decisions, suggesting that emotional and psychological factors often play a larger role than financial metrics alone.
It also highlights the importance of evaluating founders beyond their pitch, focusing on traits such as integrity, resilience, and execution capability.
A Toronto-linked voice in a global investment conversation
While angel investing is a global practice, the themes explored in Fool’s Gold are particularly relevant to Canada’s growing startup ecosystem, including the Greater Toronto Area, which continues to attract early-stage capital and entrepreneurial activity.
The book contributes to an ongoing discussion about sustainability in startup funding, investor education, and the long-term viability of early-stage investments.
Industry perspectives support a more cautious approach
The book has drawn attention from figures within the investment and business community, who describe it as a grounded and experience-based perspective on early-stage investing.
Commentary included in the release highlights the importance of understanding cognitive bias, maintaining discipline in decision-making, and recognizing the inherent risks of startup investment.
A shift toward transparency in startup investing
With its focus on losses and lessons learned, Fool’s Gold reflects a broader shift toward transparency in discussions about venture and angel investing.
Rather than focusing solely on success stories, the book aims to provide a more balanced view of the investment landscape — one that acknowledges both opportunity and risk.
As startup ecosystems continue to expand in Canada and globally, Fiorillo’s work adds to the conversation around how investors can better navigate an increasingly complex and competitive market.
GTA Weekly covers business, investing, and entrepreneurship through a Toronto lens.
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