Secrets of the Self-Made: investing lessons from classic books (and the final chapter)

September 13, 2023 | Colleen O’ Connell-Campbell


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As entrepreneurs, we often feel like we're on a rollercoaster. Fully immersed in the thrills and challenges of building our businesses. Every rollercoaster needs a strong foundation to function safely. The same goes for our business finance foundations. An evidence-based investment philosophy provides crucial grounding as we grow our companies and assets.

Over the past few months, I've explored foundational investing books with guest Alicia Castelino on my podcast, “I’m a millionaire. So, now what?”. We covered classics like The Intelligent Investor  - The Definitive Book On Value Investing by Benjamin Graham, A Random Walk Down Wall Street by Burton G. Malkiel, and Trillions by Robin Wigglesworth. The key takeaways from a philosophy focused on embracing market wisdom, tuning out hype, separating emotions from evidence, and diversifying globally.

Adopting an investment framework based on facts over predictions can seem obvious, and boring at first. But it works. As Warren Buffett has demonstrated, index funds tend to outperform active stock picking over the long haul. A thoughtful structure you stick with through up and down markets can ultimately help you reach your financial goals.

So here, to round out this series, is a list of core investing principles to bear in mind as you build your business with a cash-rich exit in mind.

  1. Embrace market pricing as an effective information processing system: The market price reflects the collective knowledge and perspectives of millions of buyers and sellers. Trying to outguess the market is difficult. Instead, let market wisdom guide investment decisions.

  2. Avoid trying to "time" the market through stock picking: Selecting specific stocks or making changes based on market predictions rarely stacks up well against a buy and hold approach over the long run. Resist the temptation to constantly trade in and out.

  3. Resist chasing past returns: Past performance is not indicative of future results. Don't choose investments solely because they did well in the past. High returns last year do not guarantee high returns next year. Focus instead on dimensions of expected returns.

  4. Let the markets work for you over the long-term: Financial markets have rewarded long-term investors who can ride out ups and downs. Keep a long-term horizon measured in decades, not days or months.

  5. Consider dimensions like size, relative price, and profitability when evaluating stocks: Research shows stocks with certain characteristics like small size, lower valuations, and high profitability have offered higher returns. Target stocks aligned to these dimensions.

  6. Diversify globally to take advantage of opportunities: Diversifying across global markets provides access to more investments and reduces risks concentrated in one country or region.

  7. Manage emotions and remain disciplined: Don't let fear or greed push you into irrational decisions. Have a plan and stick to it; even as markets fluctuate.

  8. Focus on what you can control in your business: As a business owner, put your energy into high-impact decisions within your control rather than trying to predict macro events.

  9. Work with an advisor to create a plan tied to your goals: An advisor can help develop and execute a plan tailored to your objectives and risk tolerance, not chase market trends.

Follow those 9 principles, and they will serve you well.

Self-Made Nation, this article marks the culmination of a five-year journey with my podcast under the banner: "I'm a Millionaire, So Now What?" after 277 shows! The podcast will relaunch under a new banner, at the end of September 2023, with a continued focus on supporting entrepreneurs.

I want to take this opportunity to thank you! It's been an honor to engage with thousands of listeners and connect with outstanding entrepreneurs, like you, through the publishing that comes out of my podcast. Your support over 277 episodes and counting has exceeded my wildest expectations.

While one chapter is drawing to a close, the mission continues.

In fact, exciting new horizons are unfolding.

I can't give away all the details yet, but let's just say the show is evolving to fully invest in serving self-made business owners.

The rollercoaster ride is far from over!

I'll meet you at the next twist!

TTFN (ta-ta for now),  Colleen