About The Other Side of Obvious
This channel explores investing and what lies on the other side of easy answers. Each week, I share content on money and investing that explore the ideas, clichés, assumptions and narratives that remain unquestioned.
It’s for self-investors who feel like “obvious” isn’t working. For those of us who, for one reason or another, become too busy, distracted or settled to pause and ask…“Wait a second! What?!”.
Why subscribe?
First, you will receive the tools needed to develop your own investment plan, launching and propelling you towards success.
Second, you will have access to over two decades worth of investing know-how. I’ve been fortunate to achieve 25% annual rate of return by learning (and practicing what I learned), from some of the best minds in the industry, how to become a long-term investor. By identifying and dealing with the psychological drama that every investor goes through. And by understanding what risks are appropriate for my situation.
Third, track along with live model portfolios tailored to investors of all stages.
Subscribe to get full access to this knowledge—weekly articles, select publication archives, trackable portfolios and plenty of “aha!” moments.
👉 You can also level-up to a Paid or Pledged Subscriber and in addition to receiving all articles and archives, you will benefit from additional long-form articles, bonus content and special features.
What to Expect
Weekly posts (sometimes twice weekly) on the relevant investing topics to help you build and sustain a successful portfolio. Weekly portfolio tracking updates.
Many posts will be free. Certain content will be available to paid or pledged subscribers.
Who’s Behind This?
I’m a recovering over-explainer. Excessive question-asker. In OSOO, I explore what happens when we stop accepting obvious answers and start asking better questions about our money and investing.
I’ve lived long enough to know that my assumptions don’t always serve me well. So I started The Other Side of Obvious to explore ideas that are more reliable than impressive.
I spent the majority of my career in technology (10+ yrs) and investments (25+ yrs). For the past 20 years I worked for one of the best investment advisors in the world (IMHO)!
So, The Other Side of Obvious is as much an outlet for me (a place for ideas to live), as it is a confessional. Every topic covered is one which I failed miserably to understand and to consistently live by!
So, this is for people who still believe clarity is possible, if we’re willing to look again. My goal is simply to point towards the best.
I value your time and input, and welcome the chance to go on this journey together.
Best,
Sean
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Important, Please Read.
This publication is for brains, not bets. The Other Side of Obvious shares ideas, stories, and general financial information - not personalized investment, tax, or legal advice. Investing comes with risk (including losing money). Talk to a pro before you act. Please take time to read these important disclosures before you get started.

