When a Founder Doubles Down: Why I'm Grateful for My Past Mistakes and Bullish on Tomorrow's Winners

The Thanksgiving Lesson Most Investors Never Learn

As I reflect on my investment journey, I’m deeply grateful for something unexpected: my most expensive mistakes. They’ve proven to be my greatest teachers. There’s a quote often attributed to Warren Buffett that captures this perfectly: “It’s good to learn from your mistakes. It’s better to learn from other people’s mistakes.” But the reality is, some lessons stick harder when they’re your own.

Today, I want to share two investment stories that perfectly illustrate this. One taught me what NOT to do. The other is showing me what TO do. And the bridge between them reveals a principle that separates long-term wealth builders from perpetual market chasers.

The Telecom That Changed Everything: My Amazon Miscalculation

Rewind to 2014. I was riding high as an Amazon (NASDAQ: AMZN) shareholder. The stock had nearly tripled in just a few years—the kind of move that makes young investors feel invincible, like they’re playing with “house money” rather than real capital.

Then came the Fire Phone.

When Amazon announced this device in June 2014, my reaction was immediate and visceral: this is a terrible idea. The logic seemed airtight—if this product fails, why hold the stock? So I sold.

Here’s where my analysis was precisely 50% right and 100% wrong.

The Fire Phone was indeed a catastrophic failure. I nailed that call. But I was spectacularly wrong about Amazon itself. While the device flopped, Amazon became a 14-bagger. The company expanded into cloud computing (AWS), retail acquisitions (Whole Foods), advertising infrastructure, and membership ecosystems (Prime) that transformed the global economy.

The real mistake wasn’t my judgment about the product. It was my blindness to three critical principles:

First, founder-led companies deserve the benefit of the doubt. Jeff Bezos had earned that trust through a decade of long-term thinking.

Second, innovation requires permission to fail. Companies that fear losing every battle lose the war.

Third, short-term product failures tell you almost nothing about long-term business trajectory.

Fast Forward to 2023: Testing My Lessons

I bought TransMedics Group (NASDAQ: TMDX) at the beginning of 2023 with renewed conviction. The company’s Organ Care System (OCS) represents a genuine breakthrough: preserving donated organs in living condition during transport, rather than relying on ice storage. The addressable market is massive, and the founder-led vision seemed crystal clear.

Early gains felt good. Then, in August 2023, management announced an acquisition of Summit Aviation.

My initial instinct screamed danger. An aviation company? Capital-intensive? Margin destruction incoming? The market agreed—TMDX stock was cut in half over the next few months.

Here’s where the Amazon lesson actually protected me: I did nothing.

Instead of panic-selling to recoup quick gains, I gave founder Waleed Hassanein space to execute. By year-end, his vision crystallized: a nationwide logistics network that would exponentially improve organ utilization rates and transplant outcomes.

Two years later, the numbers speak for themselves.

The Vision Delivered

TransMedics’ stock has tripled from its 2023 lows. Revenue metrics have exploded:

• Transplant revenue: up 32% in the most recent quarter
• Logistics revenue: up 35%
• Net profit margin: 17%
• In-house aviation utilization: 78% of all National OCS Program transplants

The aviation acquisition didn’t destroy margins as feared—it actually slightly compressed gross margins while simultaneously unleashing free-cash-flow margins that ballooned beyond expectations. This is the hallmark of a founder thinking in decades, not quarters.

Management now targets over 10,000 transplants within the next several years (up from current levels), with expansion into kidney donation and international markets representing multiples of the existing business.

The Grateful Investor’s Framework

Yes, new uncertainties loom. Will the next-generation heart and lung systems succeed? Can the company scale kidney donation? Is the international expansion realistic? These aren’t rhetorical questions—they’re legitimate risks.

But they’re also the exact same questions that could have been asked about AWS in 2004, Amazon Prime in 2006, or Whole Foods in 2017. And at each juncture, Amazon kept innovating despite skepticism.

The principle here transcends any single stock. When a founder-led company demonstrates long-term thinking, executes against an expanding vision, and compounds value across multiple business lines, short-term volatility becomes white noise. The grateful investor isn’t the one patting themselves on the back for one good quarter. They’re the ones patient enough to let the best founders prove themselves across multiple market cycles.

I’m holding TransMedics and adding to the position. Not because it’s guaranteed to work—no stock is. But because the founder has earned the benefit of my hindsight, my mistakes, and my gratitude for all the lessons in between.

The most valuable investment education rarely comes from your wins. It comes from your past mistakes, and the wisdom to recognize when you’re seeing the same pattern play out differently the second time around.