Podcasts > The School of Greatness > From Broke to Millions: 3 Experts Reveal Their Investing Secrets

From Broke to Millions: 3 Experts Reveal Their Investing Secrets

By Lewis Howes

In this episode of The School of Greatness, three investment experts share their strategies for building wealth. Chris Camillo covers the psychological aspects of investing, including how to handle potential losses and maintain emotional control, while explaining why a disciplined approach with consistent contributions to low-cost index funds can be an effective path to long-term returns.

The discussion also features Glennda Baker's insights on real estate investment, including tips for identifying promising properties and avoiding common pitfalls. Throughout the episode, the experts emphasize the role of financial education in preventing costly mistakes, explore the concept of compound interest, and discuss finding the right balance between saving for the future and enjoying the present.

Listen to the original

From Broke to Millions: 3 Experts Reveal Their Investing Secrets

This is a preview of the Shortform summary of the Jun 20, 2025 episode of the The School of Greatness

Sign up for Shortform to access the whole episode summary along with additional materials like counterarguments and context.

From Broke to Millions: 3 Experts Reveal Their Investing Secrets

1-Page Summary

Investing Mindset and Psychology

Chris Camillo shares insights on the psychological aspects of successful investing. He emphasizes that investors should be mentally prepared for potential significant losses—up to 70% in worst-case scenarios—while maintaining emotional control. Rather than trying to time the market, which often leads to poor decisions, Camillo advocates for a disciplined approach where consistent contributions and frugal choices can lead to steady returns over time.

Investment Strategies and Asset Allocation

When it comes to building wealth, Camillo stresses the importance of portfolio diversification, suggesting investors strategically divide their money between "risk assets" and "safe assets." He particularly recommends low-cost index funds, such as S&P 500 ETFs, as effective vehicles for long-term returns. Notably, Camillo argues against the need for complex wealth-building strategies, suggesting that consistent investment in index funds can be sufficient for most individuals.

Real Estate Investing

Glennda Baker provides practical advice for real estate investment success. She recommends thorough research of growing neighborhoods and targeting properties requiring only cosmetic improvements. Baker warns against over-leveraging and emphasizes the importance of buying properties you can hold long-term. She illustrates this with examples, such as how a $150,000 house purchased in 1975 could appreciate to a million dollars while providing rental income.

Financial Education and Avoiding Mistakes

The experts discuss how a lack of financial education can lead to costly mistakes. Baker shares her personal experience of mishandling profits from a house sale due to insufficient financial knowledge. Camillo emphasizes the power of compound interest, suggesting viewers should see each dollar as potentially worth $100 in the future. Meanwhile, Perkins highlights the importance of balancing present enjoyment with future savings, drawing from his experiences with both over-saving and overspending.

1-Page Summary

Additional Materials

Counterarguments

  • While being mentally prepared for losses is important, suggesting that investors should be ready for up to 70% losses might be overly conservative and could deter some from investing at all.
  • A disciplined approach is beneficial, but some investors have successfully timed the market or used active trading strategies to achieve higher returns.
  • Diversification is key, but too much diversification can lead to dilution of returns, and some investors may benefit from a more concentrated portfolio in areas where they have specific expertise.
  • Low-cost index funds are generally effective, but they may not always outperform actively managed funds or other investment strategies, especially in non-efficient markets.
  • Consistent investment in index funds may be simple, but it may not be sufficient for all individuals, especially those with higher risk tolerance or those seeking to beat the market.
  • Real estate investment advice often emphasizes research and cosmetic improvements, but some investors have found success in developing properties or investing in distressed assets.
  • While over-leveraging is risky, the use of leverage in a calculated manner can amplify returns and can be part of a successful real estate investment strategy for experienced investors.
  • Financial education is crucial, but even well-educated individuals can make mistakes due to behavioral biases or unpredictable market conditions.
  • The concept of viewing each dollar as potentially worth $100 in the future can encourage saving, but it may also lead to excessive frugality and a failure to enjoy the present.
  • Balancing present enjoyment with future savings is important, but the optimal balance can vary greatly among individuals based on personal values, goals, and circumstances.

Actionables

  • You can create a "market turbulence" savings account where you deposit a small percentage of your monthly income to psychologically prepare for potential investment losses. This fund acts as a buffer, reducing the stress of market downturns because you've allocated money specifically for this scenario. For example, if you're saving $1,000 a month, putting $50 into this account can build a reserve that you're mentally prepared to lose, softening the emotional impact of a market dip.
  • Develop a habit of monthly "financial date nights" where you review your investment contributions and spending habits. This regular check-in ensures you're making consistent contributions and staying frugal. For instance, on the first Friday of each month, you could sit down with your favorite beverage, review your budget, and transfer funds to your investments, turning a disciplined approach into a pleasant routine.
  • Start a "future value" journal where you record all non-essential purchases and calculate their potential future value if invested instead. This practice can help balance present enjoyment with future savings. For example, before buying a $50 video game, write it down and calculate what that $50 could grow to in 20 years at a 7% annual return, helping you decide if the immediate pleasure is worth the long-term opportunity cost.

Get access to the context and additional materials

So you can understand the full picture and form your own opinion.
Get access for free
From Broke to Millions: 3 Experts Reveal Their Investing Secrets

Investing Mindset and Psychology

Chris Camillo advises on how to approach investing from a psychological standpoint, emphasizing the importance of preparation, emotional control, and maintaining a disciplined strategy.

Prepare For Risk Asset Downsides

Camillo suggests that investors should brace themselves for substantial downsides in risk assets and be mentally ready to handle a 70% loss in a worst-case scenario. Although the specifics of acceptancing the risk are not discussed, the underlying message is that a significant loss is within the realm of possibility when investing in higher-risk assets.

Investors Should Control Their Emotions and Mindset

The podcast stresses the significance of a mindset shift when it comes to investing. Camillo implies that seeing money solely as something to spend, instead of a tool for investment, can be counterproductive. Valuing even small amounts of money for their investment potential can act as a catalyst for financial growth through the power of compounding.

Investors Timing the Market Often Make Poor Decisions and Lose Money

While specific details about the pitfalls of market timing are not mentioned, a general understanding is that investors who attempt to time the market often end up making decisions that can lead to financial losses, suggesting the need for a more thoughtful and measured approach to investing.

Maintain a Disciplined Investing Approach for Consistent Returns

Camillo advises on taking a disciplined approach to investing, where consistent contributions to an investment account, born from the savings ...

Here’s what you’ll find in our full summary

Registered users get access to the Full Podcast Summary and Additional Materials. It’s easy and free!
Start your free trial today

Investing Mindset and Psychology

Additional Materials

Counterarguments

  • While preparing for substantial downsides is prudent, some might argue that a 70% loss threshold might be too extreme for certain investors, especially those closer to retirement or with lower risk tolerance.
  • Emotional control is important, but some critics might point out that completely removing emotion from investing is unrealistic and that emotions can sometimes provide valuable gut instincts.
  • Viewing money as a tool for investment is a powerful mindset, but it's also important to balance this with quality of life considerations and not undervalue the present moment's enjoyment.
  • While market timing is often criticized, some investors have been successful with this strategy, and there are methods like technical analysis that aim to improve timing decisions.
  • A disciplined investing approach is generally sound, but it may not be suitable for everyone, as it assumes a one-size-fits-all strategy without considering individual financial goals and circumstances.
  • The concept of investing as a "life hack" may oversimplify the complexities and risks involved in invest ...

Actionables

  • Create a "stress-test" savings account to simulate investment losses and build emotional resilience. Open a separate savings account and periodically transfer a percentage of your investment funds into it, mimicking a market downturn. This practice helps you acclimate to the feeling of seeing your investment balance drop without the actual risk, training you to manage emotions during real market volatility.
  • Use a "money purpose" jar system to tangibly separate spending from investing. Label multiple jars or envelopes with different financial goals, such as "Emergency Fund," "Vacation," "Retirement Investment," etc. Allocate a portion of your income to each, with a clear emphasis on investment. This visual and physical separation can reinforce the concept of money as a tool for growth rather than immediate consumption.
  • Implement a ...

Get access to the context and additional materials

So you can understand the full picture and form your own opinion.
Get access for free
From Broke to Millions: 3 Experts Reveal Their Investing Secrets

Investment Strategies and Asset Allocation

Camillo discusses various investment strategies focused on growing wealth through diversified portfolios and simplifying investment approaches.

Diversified Investment Portfolio Critical for Wealth Growth

Camillo reinforces the importance of having a diversified investment portfolio as a key strategy for wealth growth.

Divide Money Between "Risk Assets" and "Safe Assets" to Manage Risk

He delves into the concept of "bucketing money," suggesting that investors should decide how much of their money to allocate to risk assets like stocks or bonds and how much to safer options like treasury bills or treasury-backed cash. A gist of his advice indicates a strategic allocation of money specifically for growth-oriented investments. However, he emphasizes the role of investment accounts for risk assets without explicitly mentioning how money should be divided between risks and safe assets.

Investing In Low-cost Index Funds: An Effective Strategy

Index Funds Provide Diversification and Long-Term Returns

Camillo points to low-cost index funds, such as the S&P 500 ETF, as primary vehicles for diversification and potential long-term returns. He underscores that these funds can provide effective growth for i ...

Here’s what you’ll find in our full summary

Registered users get access to the Full Podcast Summary and Additional Materials. It’s easy and free!
Start your free trial today

Investment Strategies and Asset Allocation

Additional Materials

Counterarguments

  • Diversification does not guarantee wealth growth; it is a risk management strategy that can sometimes lead to mediocre performance compared to concentrated investments in high-performing assets.
  • Over-diversification can dilute potential returns and may result in average performance that barely outpaces inflation.
  • The division between "risk assets" and "safe assets" is not always clear-cut, as the risk profile of assets can change over time due to various economic factors.
  • Some argue that treasury bills and similar "safe assets" may not be entirely safe in certain economic conditions, such as during periods of high inflation or when there is a risk of government default.
  • Low-cost index funds, while providing diversification, may not always be the best choice for all investors, especially those with specific financial goals or those who are capable of achieving higher returns through active management.
  • The assumption that ordinary people do not need complex wealth strategies may overlook the unique financial situations and goals of individuals that could benefit from more tailored advice.
  • The advice to start investing without advanced strategies may not be suitable for everyone, as some individuals may require more soph ...

Actionables

  • You can create a visual map of your current investments to identify gaps in diversification. Draw a pie chart or use an online tool to categorize your assets visually. This will help you see if you're too heavily invested in one area and need to rebalance. For example, if you notice that 70% of your investments are in high-risk stocks, you might decide to shift some funds into bonds or treasury bills.
  • Set up automatic monthly transfers to an investment account dedicated to growth-oriented assets. Determine a fixed percentage of your income that you're comfortable with, say 5% or 10%, and automate the transfer from your checking account to your investment account. This ensures you're consistently allocating money for growth without having to remember to do it manually.
  • Engage in a monthly 'investment exploration day' where you research one new low-cost index fund or other diversified inv ...

Get access to the context and additional materials

So you can understand the full picture and form your own opinion.
Get access for free
From Broke to Millions: 3 Experts Reveal Their Investing Secrets

Real Estate Investing

Glennda Baker shares insights on how real estate investing can be a pathway to building wealth when approached with strategy, patience, and discipline.

Real Estate Builds Wealth With Strategy

Investors are advised to do thorough research and build their strategies on solid principles.

Investors Should Target Properties In Growing Neighborhoods That Need Only Cosmetic Improvements

Glennda Baker explains that it is critical to understand what you're buying, urging investors to get in the weeds by driving through neighborhoods, dining in local restaurants, shopping in stores, and even assessing the quality of local produce, all of which can indicate a neighborhood's prosperity and condition. She also recounts inspiration from another investor who succeeded by investing in small houses, fixing them up, and then selling or renting them out in growing neighborhoods.

Avoid Over-Leverage; Buy Properties You Can Hold Long-Term, Even In Downturns

Baker warns against overleveraging and buying in risky or transitioning areas, which can lead to loss. She suggests buying properties in such a way that you are never in a position where you have to sell, increasing your chances of selling for a profit. Baker discusses the pitfalls of purchasing overly expensive properties to impress others rather than investing in multiple properties that could build generational wealth, using the example of Trey Young’s $20 million house to suggest that he could have bought a less expensive home and several investment properties to build wealth.

Maximizing Real Estate Value Requires Patience and Discipline

Being patient and disciplined in strategy is key to maximizing real estate value.

"Market Timing Leads To Loss; Buy and Hold Long-Term"

Although Chris Camillo does not explicitly discuss real estate, he brushes on the perception that f ...

Here’s what you’ll find in our full summary

Registered users get access to the Full Podcast Summary and Additional Materials. It’s easy and free!
Start your free trial today

Real Estate Investing

Additional Materials

Clarifications

  • Over-leveraging in real estate investing occurs when an investor borrows too much money to purchase properties, leading to high levels of debt relative to the property's value. This can increase financial risk, especially if property values decline or rental income decreases. It may result in challenges meeting mortgage payments, maintenance costs, or other financial obligations, potentially leading to financial distress or even foreclosure. Balancing leverage appropriately is crucial to mitigate risks and ensure sustainable long-term investment success.
  • Understanding the importance of rental cash flow over market timing for capital gains in real estate investing is crucial. Rental cash flow provides a steady income stream, ensuring financial stability regardless of market fluctuations. Focusing on cash flow from rentals allows investors to generate consistent profits over time, reducing the reliance on unpredictable market appreciation for wealth accumulation. This strategy emphasizes the long-term sustainability and profitability of real estate investments, offering a more reliable and resilient approach to building wealth in the real estate market.
  • To identify properties in growing neighborhoods, investors should conduct thorough research on local market trends and economic indicators. Visiting the neighborhood, exploring local amenities, and assessing the overall condition can provide valuable insights into its potential for growth. Additionally, focusing on areas with upcoming developments, improving infrastructure, and increasing demand can be indicators of a neighborhood's growth potential. Lastly, seeking properties that may only require cosmetic improvements in already desirable locations can be a strategic approach to capitalize on the neighborhood's growth trajectory.
  • A long-t ...

Counterarguments

  • While targeting properties in growing neighborhoods can be a sound strategy, it may not always be feasible due to high competition and inflated prices in such areas. Additionally, some investors have found success in gentrifying or stable, established neighborhoods where growth potential is less obvious but still present.
  • Buying properties to hold long-term is generally a good practice, but it may not be suitable for all investors, especially those looking for quicker returns or who are skilled in short-term trading of real estate.
  • The advice against over-leverage is prudent, but some investors may have the experience and risk tolerance to manage higher leverage effectively, using it to amplify their returns.
  • The "buy and hold" strategy may not always be the best approach in every market condition or for every investor's goals. There are times when market timing and strategic selling can maximize profits, especially in volatile or peak market conditions.
  • Focusing on cash flow from rentals is important, but ...

Get access to the context and additional materials

So you can understand the full picture and form your own opinion.
Get access for free
From Broke to Millions: 3 Experts Reveal Their Investing Secrets

Financial Education and Avoiding Mistakes

Experts discuss the crucial role of financial education in avoiding pitfalls and emphasize the importance of cultivating a long-term mindset for building wealth.

Lack of Financial Education Leads To Costly Mistakes

Perkins highlights the need for proactive thinking about one's financial future, tailoring saving and spending to individual circumstances, and making intentional decisions to secure financial stability. Baker shares her costly mistake of not understanding financial responsibilities, such as taxes, which led to severe consequences after making a significant profit on a house sale. This lack of awareness stemmed from her upbringing without financial guidance, resulting in spending on luxuries like a Mercedes and a Rolex, and subsequently pawning possessions during financial hardship.

Cultivating a Long-Term Mindset and Regular Saving Builds Wealth

Camillo advocates for the power of compound interest, urging individuals to see each dollar as potentially $100 in the future. By saving and investing thoughtfully, one can cultivate a long-term investment strategy. Living below one's means and focusing on regular savings and investments is fundamental, avoiding the lure of immediate gratification for future financial growth. Camillo also suggests that investing in an index fund like the S&P 500 ETF is a more successful wealth-building strategy than attempting to time the market.

Baker outlines the importance of learning from past ego-driven mistakes. She now focuses every day on actions that move her from her current position to ...

Here’s what you’ll find in our full summary

Registered users get access to the Full Podcast Summary and Additional Materials. It’s easy and free!
Start your free trial today

Financial Education and Avoiding Mistakes

Additional Materials

Counterarguments

  • While proactive financial planning is important, it can be challenging for individuals with low income or unstable employment to save and invest.
  • Not everyone who lacks financial education will necessarily make poor financial decisions, as some may have a natural or intuitive understanding of money management.
  • The power of compound interest is significant, but it also requires a stable and favorable economic environment to work effectively; during times of high inflation or market downturns, the benefits can be eroded.
  • Living below one's means is a sound principle, but it may not account for the complexities of individual situations, such as high cost of living areas or unexpected healthcare costs.
  • Investing in an index fund like the S&P 500 ETF is generally a good strategy, but it may not be suitable for all investors, especially those with a low tolerance for risk or those who are nearing retirement and need less exposure to market volatility.
  • Learning from past mistakes is valuable, but it's also important to recognize that not all financial outcomes are the result of personal choices; external factors such as economic recessions can have a significant impact.
  • Prioritizing long-term wealth over short-term pleasures can lead to a more secure financial future, but it's also important to find a balance that allows for enjoyment of life and mental well-being in the present.
  • The idea of balancing ...

Actionables

  • You can create a "Financial Autobiography" to reflect on your spending habits and identify patterns that don't align with your long-term goals. Start by writing down all significant financial decisions and purchases you've made over the past year. Review this autobiography to spot where emotions rather than logic may have driven your spending. This self-awareness can help you make more financially sound decisions moving forward.
  • Develop a "Future Self" savings challenge where you save a small amount of money each week, pretending it's a bill owed to your future self. For example, treat a $20 weekly savings deposit like a utility bill that must be paid. Over time, this habit can help you prioritize long-term wealth without feeling overwhelmed by large sums. It's a practical step towards living below your means and saving regularly.
  • Engage in a "Luxury Audit" by listing all non-essential items or s ...

Get access to the context and additional materials

So you can understand the full picture and form your own opinion.
Get access for free

Create Summaries for anything on the web

Download the Shortform Chrome extension for your browser

Shortform Extension CTA