My Worst Investment Ever Podcast Edwin Endlich – Early Doesn't Always Mean Right
BIO: Edwin Endlich is the Chief Marketing Officer of Wysh and President of the National Alliance for Financial Literacy and Inclusion.
STORY: Edwin’s worst investment was buying Tilray stock at $143 during the early hype of legal cannabis investing. Swept up in the excitement of a “new frontier,” he held on as the price crashed—eventually selling at around 30 cents and losing over 99% of his investment.
LEARNING: The fundamentals always apply, even in new or exciting industries. Don’t let hype replace due diligence.
“We’re in this AI conversation, let’s not forget the fundamentals of the market. Learn from what has happened in this space before. And don’t get too cocky.”
Edwin Endlich
Guest profile
Edwin Endlich is the Chief Marketing Officer of Wysh and President of the National Alliance for Financial Literacy and Inclusion. Edwin has spent his career at the intersection of marketing, fintech, and AI, helping financial institutions tell more human stories in an increasingly digital world. He’s passionate about making financial protection simple, accessible, and even a little more fun — proving you don’t need buzzwords or hype to make banking and technology relevant.
Worst investment ever
There’s nothing quite like the rush of feeling early—early to a trend, early to a movement, early to a once-in-a-lifetime opportunity. That’s precisely what Edwin felt in 2015–2016, when investing in legal cannabis became possible in parts of the United States.
For the first time, regular people could invest in a newly legalized industry. It felt like history happening in real time, a frontier market ready to explode. Edwin and his friends didn’t want to miss out, especially when companies were going public, and their share prices seemed destined to skyrocket.
One of those stocks was Tilray. At $143 a share, Edwin was convinced he was buying the future. He imagined stock splits, booming demand, and a cannabis empire rising from the ground floor. Instead, he watched that $143 tumble month after month, until he finally sold it for around 30 cents. The emotional rollercoaster of hope, disappointment, and finally acceptance was a journey Edwin will never forget.
A 99.3% loss.
He now calls it his worst investment—not just because of the financial hit, but because of how powerfully excitement and hype clouded his judgment.
Lessons learned
- Every investor thinks their situation is unique. But in reality, the same patterns repeat again and again.
- Markets take time to mature.
- Regulation can shift overnight.
- Early doesn’t always mean right.
- Excitement is not a strategy.
Andrew’s takeaways
- A portfolio isn’t just about diversification by industry or geography; it’s also about diversifying across stages of maturity.
- Stable, well-regulated companies like Coca-Cola or Pepsi behave very differently from early-stage, hype-driven industries, such as the cannabis sector.
- Even large companies, with teams of top analysts, often get it wrong.
Actionable advice
If Edwin could offer one piece of advice to anyone starry-eyed over the next big thing, it would be this:
Do your due diligence. Seriously.
Before you invest in anything—especially something exciting, futuristic, or rapidly trending—slow down and ask:
- Has this been done before?
- What can I learn from past bubbles?
- What does history say about similar innovations?
- Am I investing in fundamentals—or feelings?
Whether it’s cannabis in 2016 or AI in 2024, the pattern is the same. Booms become bubbles. Investors overestimate how fast an industry will mature. And emotion often wins over discipline. But with the right mindset and discipline, you can avoid these pitfalls.
Edwin’s recommendations
Edwin encourages people to empower themselves with real financial knowledge. That’s why he co-founded the National Alliance for Financial Literacy and Inclusion (NAFLI)—a nonprofit dedicated to helping individuals understand money, investing, and financial products.
Whether you’re new to investing or leading a financial institution, NAFLI offers education, tools, and resources to help individuals make more informed financial decisions.
No.1 goal for the next 12 months
Edwin’s goal for the next 12 months is to have a full, uninterrupted conversation with his daughter, one that lasts longer than 10 minutes and isn’t broken by phones, notifications, or distractions. Edwin wants to rebuild community and presence—starting at home.
Parting words
“Stay focused and look to the past.”
Edwin Endlich
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Connect with Edwin Endlich
Andrew’s books
- How to Start Building Your Wealth Investing in the Stock Market
- My Worst Investment Ever
- 9 Valuation Mistakes and How to Avoid Them
- Transform Your Business with Dr.Deming’s 14 Points
Andrew’s online programs
- Valuation Master Class
- The Become a Better Investor Community
- How to Start Building Your Wealth Investing in the Stock Market
- Finance Made Ridiculously Simple
- FVMR Investing: Quantamental Investing Across the World
- Become a Great Presenter and Increase Your Influence
- Transform Your Business with Dr. Deming’s 14 Points
- Achieve Your Goals