About Sam Sivarajan
I’ve spent my career in places where decisions had real consequences. Now I help others make them.
For three decades I worked in places where being wrong was expensive—as a lawyer, an investment banker, and the person running the firm.
The hardest calls were never the ones with the easy answers. They were the ones you had to make anyway—before the picture was resolved, with real money and real people on the line.
That’s the work I care about.
And it’s the work I now help others do.
My path
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I started as a corporate lawyer, structuring complex banking transactions.
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I moved to investment banking in London, advising on more than $40B in cross-border M&A across telecoms and technology.
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Then in Canada I built and led three wealth-management firms responsible for over $80B in client assets—through dislocations, crises, and large-scale transformation.
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Along the way I earned a doctorate in behavioral finance—to understand why even very capable people struggle to decide well when certainty disappears.
And I’ve been early to the shifts now reshaping the industry—AI in advice, new retirement products, and new models of investment advice.
Today I work with wealth and private-client firms on the decisions that determine whether they endure.
Where the thinking happens.
Two Newsletters
The Uncertainty E.D.G.E.™, on decision-making under uncertainty.
The Good Human Practice, on character and meaning.
Each published every two weeks.
A Monthly Column
A regular column in The Globe & Mail on making better investing and personal-finance decisions.
Five Books
Written over the last decade, exploring decision-making, behavioral finance, and the human side of leadership.
Away from the desk.
As in my career, I’ve been drawn to places where certainty is limited and consequences are real. The Himalayas, the Andes, the Alps. The Boston Marathon. Long distances on a bike. Extended silent meditation.
I’ve tackled these challenges not so much for the achievement, but for what they teach me about judgment, pacing, and responsibility when conditions change without warning.
Q&A
The Proust Questionnaire
Answers to classic questions on personality and perspective.
What is your idea of perfect happiness?
Enjoying a good meal, some wine, and a few laughs with friends and family.
What is your greatest fear?
Living someone else’s life.
What is the trait you most deplore in yourself?
Impatience.
What is the trait you most deplore in others?
A sense of entitlement.
Which living person do you most admire?
Angela Merkel.
What is your greatest extravagance?
Used to be ties – thanks to Covid, no longer an issue.
What is your current state of mind?
Contemplative.
What do you consider the most overrated virtue?
A neat desk or work area.
On what occasion do you lie?
When a loved one asks me what I thought of something they made that I didn’t like.
What do you most dislike about your appearance?
Nothing – stoicism teaches me to accept what I cannot control.
Which living person do you most despise?
Anonymous social media trolls attacking others not in their tribe.
What is the quality you most like in a man?
Character – doing the right thing at the right time for the right reason.
What is the quality you most like in a woman?
Character – doing the right thing at the right time for the right reason.
Which words or phrases do you most overuse?
Like. Look.
What or who is the greatest love of your life?
My wife and daughter.
When and where were you happiest?
Coming home from work to have my young daughter run into my arms, excited to see me.
Which talent would you most like to have?
Sing on-key.
If you could change one thing about yourself, what would it be?
Better able to stay in the moment.
What do you consider your greatest achievement?
Convincing my wife to marry me.
If you were to die and come back as a person or a thing, what would it be?
An eagle or falcon.
Where would you most like to live?
I am fortunate enough to be able to split my time between Toronto and Vienna.
What is your most treasured possession?
Physical and mental health.
What do you regard as the lowest depth of misery?
Self-pity.
What is your favorite occupation?
Reading, writing, talking (not necessarily in that order).
What is your most marked characteristic?
Goal-setting, planning, and execution.
What do you most value in your friends?
Loyalty. Fun. Shared Values.
Who are your favorite writers?
Will Storr, Malcolm Gladwell, Erich Fromm, Alexandre Dumas, Margaret Atwood.
Who is your hero of fiction?
Edmond Dantes – The Count of Monte Cristo.
Which historical figure do you most identify with?
Hector of Troy.
Who are your heroes in real life?
Terry Fox, Nelson Mandela, Mother Teresa.
What are your favorite names?
Isabella, Matthias.
What is it that you most dislike?
Wasted talent.
What is your greatest regret?
No regrets – I am blessed with what I have and what is in my control.
How would you like to die?
Of old age, having made a difference, with friends and family sadder for my passing, but happy for the life I have lived.
What is your motto?
“There is nothing noble in being superior to your fellow man; true nobility is being superior to your former self.” Thank you, Ernest Hemingway.