I genuinely believe much of my success comes down to luck rather than intelligence. I grew up as a white male in a working-class family in a top Western country in the 80s. My parents, both school teachers, valued education and encouraged me to explore academics, sports, and culture. I had access to a free schooling system and affordable university, enabling me to complete a double degree. These factors were crucial to my journey—ingredients that 90% of the global population simply doesn’t have.
Often, people who experience financial windfalls—whether from selling a company, stock gains, crypto profits, or real estate—attribute it to their skills as investors. While they may have made some smart decisions, luck and timing often play a larger role than they realise. Don’t mistake skill with luck is a principle I attempt to follow.
Here are some personal examples that illustrate this point.
In past crypto boom cycles, I’ve seen returns simply from following the hype. During euphoric phases, you could buy nearly any top-100 coin, and prices would likely rise. Without any real understanding of the fundamentals, I felt like a “crypto expert” as my picks shot up by 200-300% in months. But, without solid insights, these gains quickly evaporated. When I reinvested, I faced losses as high as 80% as outlined here in lessons learnt in crypto investing.
A similar story unfolded with my NVIDIA stock purchase in 2021. I initially invested in NVIDIA because it was producing chips for crypto mining. During the crypto surge, my stake rose nearly 200% before the market crashed in 2022, and so did NVIDIA’s value. I held on, thinking NVIDIA might still be valuable in other sectors. Fortunately, the AI boom arrived, NVIDIA pivoted, and my investment rebounded dramatically. It wasn’t foresight—I just got lucky.
Another example is an NDIS property investment. Our initial thesis didn’t pan out, but we exited with a profit due to COVID-19’s impact on supply and demand. Again, it was being in the right place at the right time rather than strategic foresight.
I’ve observed similar patterns in successful entrepreneurs who assume every new venture will thrive after an initial win. Recently, I met a founder who made a significant exit in SMS tech but then launched a mediocre proptech product aimed more at his millionaire lifestyle than the broader market. I explained that his product lacked a go-to-market strategy, but he disregarded this advice, blinded by his past success. Unfortunately, his new venture ultimately failed, costing him both time and money.
In hindsight, I see that timing and circumstances often play a bigger role in success than we’d like to admit. Luck isn’t a skill, but it’s an ingredient we often overlook when reflecting on our achievements.
Take, for example, the sale of my first two tech businesses. Their success was more about fortunate timing than a carefully crafted exit plan. While both businesses were profitable, they weren’t exactly high-growth ventures; they were closer to steady, cash-flow operations. The eventual exits were driven by long-standing partnerships that developed over a decade, with those partners ultimately deciding that each business would be a good fit for their own companies at just the right moment.
Reflecting on Outcomes
There’s no more humbling moment for a big loss than right after a substantial windfall. One practice I’ve developed after any successful gain is conducting an objective review of the investment and analysing the factors that led to its success. I try to identify which elements aligned with my initial assumptions and which were influenced by circumstances or luck. This reflection helps me refine my approach, evolving the process I use to select and manage future investments.
Remember, nothing is as Good or as Bad as it seems. Meaning the good times can quickly change into bad!!!
Conclusion
Reflecting on my journey, it’s clear that luck, timing, and circumstances have played significant roles in my success. While skill and effort are important, acknowledging the influence of luck keeps me grounded and aware of the unpredictable nature of success. This mindset not only prevents overconfidence but also reminds me to approach future ventures with humility and realism.
For anyone riding a wave of success, remember that not every win is purely a result of skill. Recognising the role of luck in our achievements keeps us open to learning, grounded in our decisions, and better prepared for whatever the future holds.
TheBucket 