Losing Money

Embarrassed and ashamed

It’s possible to make a lot of money so quickly that you don’t realise the import and scale of what you’ve accomplished. Because of this it’s possible to lose it quickly, too. That’s embarrassing. It’s embarrassing enough to make it difficult to admit what’s happened, even to yourself.

Denial and Isolation

I MADE A MILLION dollars when I was fifty-one years old. It had taken only four years from a standing start. I was also collecting unemployment insurance, having only a few months earlier left the Swiss bank where I had worked for years.

The money was tied up in protected retirement accounts that couldn’t be accessed without heavy penalties and taxes in two countries. Yet there were immediate obligations, rent and living expenses, that had to be paid. As my unemployment insurance ran out I found myself in the paradoxical situation of being wealthy on paper while effectively being broke at the same time.

I took an early dispersal of a large part of the money and I had my broker withhold funds for the associated penalty and taxes. I thought that having made money once already, I could make more — that was stupid.

Looking back it’s easy to see what I might have done differently: the tax rules that I might have invoked and the forms that I could have filled out to avoid what ensued. Learning these things, too late to make a difference, isn’t the same thing as having learned from my mistakes.

Though unable to find a new position in one of the big banks I was able instead to make money by traveling Europe and the Middle-east teaching corporate and government clients the skills that I used to utilize in the bank. I was able to secure Swiss citizenship for my family and myself, partly on the strength of my high net worth. But, I had started down a path of lying to people about my reputed success.

Anger – Superego and Id

I briefly considered and then chose not to put a meaningful portion of the money into Berkshire Hathaway, a bargain at the time, selling for one hundred twenty thousand dollars per share. Instead I reinvested most of 1.4 million dollars into the same highly leveraged instruments with which I had initially grown it from less than seventy thousand dollars.

I embraced a fixed mindset built on the presumption that my high IQ would continue to give me an advantage over most of the market. But this time, in spite of a chorus of cable news pundits enthusiastically cheering along with my analysis of the fundamentals underpinning my investment, the prices inexorably fell and kept falling.

Only those who will risk going too far can possibly find out how far one can go.


Within two years my portfolio had contracted to less than one hundred thousand again. Yet my ego kept me convinced that I was right. Being right isn’t good enough. Eventually share prices did recover to new all time highs and my analysis proved out but I was already out of the game by then and being right doesn’t get you your money back.

In a short, frank conversation in an elevator in New York with a billionaire who’d earlier in the day fielded my pitch for an app startup, I learned of the simple concept of a personal floor – an arbitrary amount of money that you’re not willing to risk having your assets fall below. I had to admit to myself that I’d foolishly risked and lost more than enough money to have lived modestly yet comfortably off of the interest income for the rest of my life.

Bargaining – Once More with Feeling

I took a step back and deconstructed what had happened. I took the time and put in the effort to genuinely understand how I had been able to make the money in the first place and how I had lost it. I studied in earnest and learned many new things that I simply hadn’t known the first time around.

Starting again, I regrew my assets to within a hair’s breadth of a million dollars – roughly three quarters of a million in an IRA and a Roth IRA in the states and another two hundred thousand francs untouchable and unusable, as cash in a Swiss pension account. And there I was again, unable to meet our living expenses on only my income from teaching, yet with a small fortune in my name sitting tantalisingly out of reach.

Thinking outside of the box I wrote, illustrated, and self published a pair of children’s books which each briefly went to number one in their category on amazon.com in several countries. I felt like a genius again but it turns out that even successful books don’t usually generate much money.

Classic Underwood typewriter

And then while I was offline kayaking a river in the south of France the market experienced a black swan event and my American accounts were decimated again. I conceded to myself that I didn’t know what I didn’t know – and that that was a dangerous situation.

Depression – A Hero’s Journey

I enrolled in a course offered by an author and investor whose writing had proven valuable to me previously. I learned about the Kelly formula, a mathematical idea that yields an asset allocation strategy maximizing return on investment while mitigating the likelihood of a total loss.

And, then I did something stupid again: I bet, and that’s the only word for it – “bet,” more than I could afford to lose on an investment that I didn’t really understand. I followed my hero, who it turns out was following one of his heroes, into what he termed at the time – “perhaps the best investment of my life.” To be clear, I don’t blame him or anyone else for what unfolded next. My choices were my own.

A man alone before a precipice

We all fell prey together to an investment group who unscrupulously, if technically legally, acquired control of our company’s debt, forced a bankruptcy, and wiped out our equity, seizing ownership of the reorganised corporation and reaping outsized profits for themselves at our expense.

Watching the drama of the bankruptcy trial unfold I found someone new to learn from, a new champion to cheer for, a well grounded yet somehow larger than life investor who had the means and the temperament to team up with my hero and to fight against the injustice being perpetrated against us.

Because of the combined efforts of these two together we almost prevailed – almost. But, like the heroic Red Viper in his epic battle against The Mountain in Game of Thrones we were undone. And, the money was lost – again.


This is what imposter syndrome feels like. It feels like being ordinary: not heroic, not a genius, not special. It’s hearing the voice in your head say, “a fool and his money were lucky just to get together in the first place.” It feels like losing.

I apologize to the people that I feel that I let down: to the friends who admired me and modeled my success, to my would be mentors who I wanted to impress, to my wife, and to myself. Why we do things matters. After a lot of reading and thought, I’ve found new reasons to do what I’m about to undertake once more.

It made a difference for that one!


The fable of my success, carefully curated before now, has actually helped some people to succeed themselves. Like the small child in Loren Eiseley’s The Star Thrower, I made a difference to some.

What would happen to the many problems rooted in income inequity if more people understood the origins of wealth in business ownership? What would happen to our society if more decent and generous people became sustainably wealthy, if people figured out that life isn’t a zero-sum game? That’s what I want to find out.

I’m starting again. The return so far this year on what remains in my US accounts is prodigious as a percentage but it doesn't yet amount to much money in real terms. Swallowing hard and assessing where I am now, I’m more optimistic than fearful.

I’m going back to work full-time as I take the time to regrow my assets again. In this moment I’m reminded of words from one of my favorite movies: “I don't know the future. I didn't come here to tell you how this is going to end. I came here to tell you how it's going to begin…”


published by                        James Boyer


  1. Nate johnson 15 March 2017

    Hi James
    Been going thru a bit of a challenge myself. This gave me a ray of hope. Thank You for sharing…

    • James 17 March 2017

      Thanks, Nate. I’m glad that you found it helpful. It was a difficult piece to write.
      I hope that you’ll find a way through your own difficulties, too. Sometimes we win; sometimes we learn…

  2. B Koranache 24 March 2017

    Wow _ well done, James! And very much in the ‘banker voice’ if u like! Although I’ve known you for over 25yrs, we’ve only had a brief, 3 yr friendship whilst working as colleagues in Detroit. You were a brilliant, quantitative mind then-tempered with a flair for tasteful design! 🙂 I’m not surprised you’ve become a Swiss banker! I’ve actually become more sophisticated with maths, financial strategies and mastery in the second phase of my life. I went thru a rollercoaster sojourn of my own with Internet properties and risks with minimal to no reward. I did learn a lot from the losses and after reading that famous ‘Who Moved My Cheese’ tome-I redirected my resources much like you have-to critical path successes.

    Tragedies happen and I’ve learned I have to factor the worst possible personal scenarios into my lifes scheme as well. Most folks clumsily stumble thru life trying to find portent in their repetitive missteps. Few come any where near the remarkable, clear and focused thinking you’ve exercised here in your post.

    I thank you for this advise, good sir!

Leave your comment