The Second Million

My Journey to Becoming a Multi-Millionaire

Reaching my first million in 2018 was a milestone that changed everything. What happened next surprised even me: in just three years, I doubled that initial fortune. The journey from disciplined saver to aggressive investor taught me lessons that transformed not just my wealth, but my entire perspective on life.

  • The Power of Concentration: I allocated over 50% of my portfolio to a single asset class—a strategy that would terrify most financial advisors but delivered extraordinary returns.
  • Timing the Market: During parental leave, I discovered that short-term stock market trades could accelerate wealth accumulation far beyond traditional long-term investing.
  • Exponential Growth: The first million came through years of disciplined earning and saving. The second million came through strategic risk-taking and the magic of compounding.
Net Investable Assets Growth Chart

The graph tells a fascinating story: eight years of steady, linear growth followed by an explosive acceleration once I crossed the million-dollar threshold. This wasn’t luck—it was the mathematical reality of compound growth finally reaching critical mass. When money starts working for you instead of you working for money, everything changes.

Gross Income Growth Chart
  • Beginning in 2020, income from stock trading is included and reported as 1099-B income.

My investment strategy evolved from traditional stocks to alternative assets through Reg D 506(c) platforms: peer-to-peer lending, small business loans, real estate crowdfunding, and most recently, litigation finance. While passive income grew steadily, I learned a crucial lesson: concentration is the path to getting rich, while diversification is the path to staying rich.

How Wealth Transformed My Behavior and Beliefs

Money doesn’t just change your bank account—it changes your mind. As I climbed the socioeconomic ladder, uncomfortable truths emerged about human nature, relationships, and what truly matters in life.

The Uncomfortable Reality: As we rise in status, we often leave people behind. This isn’t intentional cruelty—it’s the natural consequence of different life trajectories. The friends who once shared your struggles may not understand your new challenges, and vice versa.

The Great Digital Cleanse

I’ve systematically eliminated digital connections that no longer serve me, creating space for what matters:

  • Phonebook Strategy: I change my number with every job change or phone upgrade. This simple tactic keeps recruiters at bay while ensuring my contact list stays current and meaningful. My personal contacts have dwindled to just one non-business relationship—including the painful decision to remove a childhood friend of decades.
  • Email Evolution: I periodically refresh my email addresses, though less frequently than phone numbers due to the complexity of updating primary accounts. Recently, I deleted an email address that had served me for over a decade.
  • Skype Cleanup: I closed all personal and business accounts, creating a new one solely for the few people who still actively use the platform.
  • Discord Community: This gaming platform became my primary tool for managing a private investor group—proof that the best solutions often come from unexpected places.
  • LinkedIn Liberation: With my current position likely lasting until retirement, I closed my LinkedIn account along with other job platforms. When you’re not seeking employment, maintaining a professional online presence becomes unnecessary overhead.
  • Facebook Exit: After a data breach affected 50 million users, I immediately deleted my account. Sometimes the best security strategy is complete elimination.

The Friendship Paradox

I’ve learned to identify and avoid people who view success as a zero-sum game. These individuals become jealous or angry at others’ achievements, revealing their scarcity mindset. While I’ve lost many friends through natural attrition, there’s comfort in knowing that those who remain genuinely celebrate success rather than resent it.

A Warning About Empathy: As we rise in socioeconomic status, we risk losing our ability to connect with others’ struggles. Our body language can betray disinterest, creating negative impressions. Even when we can’t relate, we should show respect and gratitude for human connection.

Personal Relationships: Quality Over Quantity

I’ve invested heavily in self-education rather than relationship-building. This choice has made me more selective about social interactions. I now seek people who either have something to teach me or can learn from me—creating mutual value exchanges that make relationships meaningful rather than obligatory.

Over the years, I’ve learned to ignore what others say until they earn my trust. Everyone has strong opinions, but few have results to back them up. Trust is earned when actions align with words.

Corporate Life: The Great Disillusionment

My relationship with corporate work has fundamentally shifted. When your full-time income represents only a small fraction of your net worth, staying motivated becomes increasingly difficult. Climbing the corporate ladder for incremental salary increases becomes mathematically irrational when it requires greater responsibilities, longer hours, or unpredictable schedules.

In the long term, careers become rounding errors. The corporate rhetoric about “passion” and “loving what you do” will never make anyone wealthy. These are feel-good platitudes designed to keep employees engaged in a system that benefits shareholders far more than workers.

The Ultimate Realization

Life fundamentally changes when we choose time over money and value over price. Once you reach your financial goals and recognize the point of diminishing returns, stress becomes a choice rather than a necessity.

Think of it like thirst: water becomes infinitely more valuable when you’re dehydrated. Similarly, accumulating wealth beyond the point where additional money makes only marginal differences in life quality becomes meaningless. Instead, we could invest our time, effort, and energy in pursuits that matter more than money: relationships, experiences, personal growth, and contributing to something larger than ourselves.

This is the true freedom that wealth provides—not the ability to buy more things, but the ability to choose what matters most and pursue it without financial constraints.