Henry Fiorillo

I write about the successes and failures of early-stage startup investing. I hope that by sharing mistakes, others can avoid them, and that the good decisions leading to positive outcomes will provide valuable insights.
– Henry Fiorillo

Henry Fiorillo’s has had a long and varied career in a variety of corporate roles encompassing market research, corporate planning, and line marketing. He has lectured at the University of Toronto and York University in the field of marketing and co-authored a leading reference text titled Market Segmentation: Concepts and Applications that was required reading in business school programs in the US and Canada.

Henry obtained a Bachelor of Arts in Economics and Psychology from the University of British Columbia followed by an MBA degree from the University of California at Berkeley with a focus on consumer research and buyer behaviour and a core interest in finance.

He has published articles on technical approaches to understanding consumer behaviour as well as on broader topics such as investor relations communication strategies and advertising effectiveness.

Recognized as a leading expert at understanding buyer behaviour, whether at the consumer or industrial level, Henry has earned recognition as a Trusted Advisor to CEOs and Boards who have sought his counsel in the areas of branding and marketing strategies.

Research Management Group (RMG), the market research firm he established, has for over 47 years provided sought after marketing and strategic planning advice by a wide range of Canadian, US, and European clients.

Given his long-standing interest in business innovation, Henry has earned a well-deserved reputation as a successful startup or Angel investor with many of his venture exits resulting in 10 to 50 or more times invested capital.

He has often provided mentoring advice to anyone seeking his views on the do’s and don’ts when contemplating early stage investing.

Currently, he’s hoping to have successful exits from his remaining positions.

Fool’s Gold:
Angel Investing and the Fine Art of Losing Money

Avoid being blinded by the shimmer of FOMO, polished performers, or overconfidence that lead to fool’s gold investments. Instead, take advice from an investor behind storied startups as he teaches you the fine art of losing money, so you can master the finer art of making it.

“Fool’s Gold is a bracing antidote to the hype and mythology surrounding angel investing. With uncommon honesty, Henry Fiorillo shows how cognitive bias, misplaced trust, and overconfidence quietly destroy capital. This is not a how-to-get-rich book. It’s a how-to-survive one. Required reading for any serious early-stage investor.”

– J.B. Handley, Founder of Bochi Investments

“A brutally honest acknowledgement by a veteran investor of the pitfalls of startup investing, rich with the details of errors made and insights gained over decades of experience making and (mostly) losing money in the startup ecosystem. A valuable reality-check for anyone planning to commit capital to this high-risk asset class.”

– Bev W. Tudhope, Former Co-Chair, National Angel Capital Organization (NACO)

“Henry Fiorillo’s Fool’s Gold is a refreshingly honest solution to the hype-driven narratives that dominate startup investing. With wit, hilarity, candor, and hard-won wisdom, Fiorillo exposes the cognitive biases and common traps that lead even experienced angels astray. This is essential reading for anyone considering early-stage investing—or anyone who wants to understand why most startups fail.”

– John Ruffolo, Founder & Managing Partner, Maverix Private Equity

“This book is what happens when a seasoned angel investor stops celebrating luck and starts documenting labor. Fiorillo strips away the mythology to reveal angel investing for what it really is: hard work, slow learning, frequent losses, and the occasional well-earned win. Fools’ Gold is an entertaining, clear-eyed reminder that in startup investing, losses are common, humility is earned, and luck is often mistaken for skill. A must read for any aspiring angel.”

– John Eckert, Co-founder of Round13 Capital

“Fiorillo has written a comprehensive book on angel investing which reflects his extensive and sadder but wiser experiences. For anyone engaged in this activity, the hard-earned lessons and resulting suggested guidelines enumerated in the book would serve as an invaluable check and balance on their own inclinations, impulses and judgement.”

– David Kassie, Executive Chairman, Outcome Metric Asset Management and Chairman Emeritus, Canaccord Genuity

“Fool’s Gold is an engaging, experience-based guide for investors seeking the unvarnished truth about early-stage investing. Fiorillo provides sharp insights on how to spot the real thing over “fool’s gold.” It is a deeply personal, practical resource for both aspiring and seasoned angel investors.”

– Ron Farmer, Managing Director of Mosaic Capital Partners, Senior Partner Emeritus of McKinsey & Company

“I’ve had the pleasure of watching Henry assess and make angel investments for more than two decades. His practice of surrounding himself with smart, independent thinkers to rigorously evaluate opportunity was one of my earliest and most enduring lessons in investment decision-making. Fool’s Gold is rich with practical advice, candid stories, and hard-won lessons from the high-risk pursuit of backing winners—and learning from the losers.”

– Bruce Croxon, Co-founder Lavalife, former Dragon on CBC’s Dragons Den, Founding Partner Round13 Capital

“Henry pulls back the curtain on angel investing with rare candor. Fool’s Gold reframes the craft at its core: you are not backing a pitch deck—you are backing a person. For those serious about becoming angel investors, this is the education most earn only after costly mistakes—Henry spares you the tuition.”

– Julie McClure, serial entrepreneur and investor, founder of UN-PAUSE, Advisor, Price Center for Entrepreneurship & Innovation, UCLA Anderson School of Management

“Anyone picking up Henry Fiorillo’s book Fool’s Gold and has an interest in the world of early-stage startup investing will be duly rewarded by reading this important book. Fiorillo delivers an immensely interesting and engaging tale that illustrates the complexity of Angel investing, where the investor can be tripped up by the many moving parts and the need to verify fact vs fiction when founders make claims that are often more fanciful than factful. The reader will benefit from the mistakes Fiorillo made and the knowledge he has acquired, offering those interested in this type of early stage investing a handbook on what to watch for when considering Angel investments, or for those who have previously made early-stage investments with an unhappy result and are looking to increase their chances of winning at this difficult and risky game.”

– Garrett Herman, Chairman and CEO, Loewen, Ondaatje McCutcheon Limited