COMMENTARY| Like trips to Paris, each journey to Bubbleville is different. I’m a firm believer that places get better each time you go. Yet there is nothing like your first time and I still look back on first timers and feel some admiration. Everything is shiny and new, and nothing could possibly go wrong. Yes, Bubbleville changes as Tulips get washed away by the South Sea and Railroads become SPAC backed flying taxis. But the fundamentals, or lack thereof, remain the same. Greed replaces rationality and easy money lures investors with a sirens’ song. The real change to Bubbleville is not it, but you.

The ghosts of bubbles past

It is early 2000 and I’m sitting in my university dorm room in Connecticut. The NASDAQ is going through the roof and I’m on getting ready to make some money. I don’t know what I’m doing. But that's ok because I don’t know, that I don’t know, what I’m doing. What I do know is we are in a “new” economy and technology is going to increase productivity – forever. That seems to be enough knowledge to know to buy Global Crossing, to buy Cisco.

 I fly off to Cancun for spring break in March 2000 oblivious to what became obvious only after the bubble burst. That IPOs were at all-time highs that would not be seen until 2020 and the first quarter of 2021. Oblivious that tech insiders were cashing out by selling 23 times more shares than they bought. Oblivious to the pronouncements that earnings didn’t matter would become a joke. Despite investment results that were fitting of my ignorance, it was an opportune time in my life. I was young, the losses had little impact on my day to day life and the opportunity cost of my meagre losses paled in comparison to the lessons I learned.

 I am walking home from work in Boston during the frigid winter of 2008. My job is consulting for the financial services industry. The markets are in a freefall and my boss and the person directly below me have been laid off. My suspicion that I am next is rational even in retrospect. My wife is in the middle of her PHD program in year three of seven where her yearly earnings could be generously described as modest.

 I have a couple of things going for me though. I have experience from the .com crash. I have the knowledge I picked up getting my MBA and through the CFA program. I have read extensively on investing with a vow that my ignorance during my first trip to Bubbleville will not be repeated. I make some mistakes – Citigroup, Washington Mutual - but I hold my nerve and I put money into the market when the newspapers are predicting the demise of capitalism.

 There are a lot of things in this version of Bubbleville not to like. There are finfluencers masquerading as experts. There is a celebration of ignorance that is personified in the mantra that ‘stonks only go up.’ I’ve taken a snarky journey through Bubbleville but I know more than anyone that most investors are just trying to build a better future for themselves and their families. They are confused, they are worried, and they are buffeted by the constant stream of stories of people getting rich. In Bubbleville the business section moves to the front page and nobody is immune from FOMO.

Thursday, Jan. 8, 2009, a newspaper vendor sells papers outside the Bank of England in the City of London

I do a webinar twice a week and I can hear this mix of fear and FOMO in the questions, I get from attendees. A strange thing happens when we start crawling through this wall of greed. We like to pretend that people are ignorant sheep during bubbles. The thing is that most people know what is happening isn’t real and isn’t going to last. They just think they can get out in time. Bubbleville is an illusion. We are all dancing to Chuck Prince’s proverbial music, but nobody knows when the song ends. And nobody wants the music to stop and that is why there is such a virulent reaction to anyone that dares questions Bitcoin at $60k or a publicly traded flying taxi company valued at $6.6 billion despite missing a couple of key elements like a finalised prototype for a flying taxi, a factory to build the flying taxis or government license to operate an aircraft. I’ve spent six and a half years living in Australia bemoaning the state of local sandwiches, but I don’t care what level interest rate is, no single deli in New Jersey is worth $100 million USD.

If past trips to Bubbleville teach us anything it is that the subsequent crashes do more than just impact people financially. Whole generations of investors lose more than money, they lose confidence. Markets go up and markets go down but the true damage from Bubbleville and the hype that is perpetuated by Facebook boards and finfluencers is that impossible expectations are being set. Expectations of the perfect life and the investment returns that will fund that life. Seemingly flippant comments about diversified portfolios returning 12 per cent a year are setting people up for failure.   

I have jokingly referred to myself as the lonely bear in this series. However, I did not write these articles because I wish any ill will to the citizens of Bubbleville. I work for a company that is inexorably linked to the fortunes of the stock market. My team sells a product that is in large part driven by the fortunes of Australian investors. As I said in the first piece, 70 per cent of my net worth is invested in stocks. I am writing these articles because I know what it is like to live through a brutal bear market. I am writing these articles because I can vividly remember what I was feeling walking home from work in Boston during that frigid winter of 2008 when I struggled to do what I absolutely knew was right.

I have the intellectual modesty to know that I have no predictive power over the future. To paraphrase a reader that emailed me after the first article, none of us knows if this bull market will last for weeks or years. That fact doesn’t stop me from being ready. My portfolio is filled with names that I bought in 2002 and in 2008 / 2009 so I know the opportunity that may be ahead of us. I built core positions after the GFC that I hold to this day in Pepsi, ADP, Johnson & Johnson and Diageo. This list is enhanced by survivorship bias but that doesn’t obscure the fact that you can build positions in great companies at fire sale prices during a bear market. I’ve let some cash build up and I have my list of the wide-moat companies that I want to own. I’m ready to turn back on the dividend reinvestment plans in my accounts. Now I just need to summon the nerve to buy when the inevitable fall comes and the whole world is once again lined up and telling me that I’m crazy.   

I’ve heard a bunch of great feedback from readers after Part 1 and Part 2 of this series. Stories about mistakes they’ve made and the resilience it takes to get up, dust themselves off and use those mistakes to become better investors. I started this series by talking about how my job has made me intimately familiar with Bubbleville. It has also strengthened my fervent belief that investing can transform lives. It is the story of Margaret, Patricia and Robert. Their stories and countless others give me the hope that my snarky journey through Bubbleville will inspire people to keep investing regardless of what happens. The paradox of Bubbleville is that the illusion only becomes real when a crash proves its existence. 

I want to hear your own stories from Bubbleville. Email me at


My journey through Bubbleville: