Podcast Summary: Money Guy Show – "The 5 Biggest Investing Mistakes"

Hosts: Brian Preston and Bo Hanson
Episode Date: January 2, 2026

Episode Overview

This episode of the Money Guy Show tackles "The 5 Biggest Investing Mistakes," with hosts Brian Preston and Bo Hanson guiding listeners through the common pitfalls that can sabotage wealth-building. The duo shares personal stories, actionable data, and practical frameworks to empower listeners to use simple, time-tested investment strategies—debunking the myths and mistakes that so many rookie and seasoned investors alike fall into. The goal: build confidence, avoid costly errors, and help your assets work harder, so you can quit worrying and start enjoying life.

Key Discussion Points & Insights

1. Mistake #1: Not Starting to Invest Soon Enough

[00:36 – 04:28]

• Most Americans don’t begin investing until their early thirties—average age 33—while 40% have nothing invested at all.
• The Cost of Waiting:
  • Investing just $95/month starting at age 20 could make you a millionaire by retirement.
  • Delay to age 30, and you must save $340/month; wait until 40, and it’s over $1,000/month.
• The Power of Compounding Growth:
  • “Do you want it to be you and your savings rate, or do you want to give it the power of time so that the compounding growth actually does the heavy lift for you?” – Brian [02:55]
  • Delaying means a greater share of your wealth must come from your own contributions, not growth.
• Memorable Quote:
  • “The absolute best time to start investing was yesterday. Which means by default, the second best time to start saving and investing is right now, today.” – Bo [02:33]

2. Mistake #2: Starting to Invest Too Soon

[04:28 – 07:23]

• Surprise Point: Starting to invest before establishing a solid financial foundation can be dangerous.
• Cover your risks first: insurance, emergency funds, and pay off high-interest debt.
• “Don’t build your financial foundation on a fragile basis.” – Bo [05:01]
• The solution is the Financial Order of Operations (FOO):
  • Step 1: Cover deductibles/insurance.
  • Step 2: Employer retirement plan match.
  • Step 3: Pay off high-interest debt.
  • Step 4: Emergency savings.
• Only after these should you start aggressively investing.
• Memorable Quote:
  • "If you're not covering the basics ... you could have an emergency that could derail your financial life forever." – Brian [05:29]

3. Mistake #3: Investing in the Wrong Things

[07:23 – 14:48]

• Trendy Temptations: Crypto, single stocks, sports betting, and gamifying finances capture attention but often hurt long-term returns.
• Most millionaires built wealth via mundane employer retirement plans, index funds, and steady contributions.
• The S&P 500 and target date index funds are suggested simple vehicles for long-term success.
• On Speculative Investing:
  • “It’s kind of like doing sports fishing versus fishing with nets. If you know that you have to feed your family, you know you’re going to act differently than if you’re just doing this for the fun of it.” – Brian [08:37]
• The Benefit of Index Funds & Target Date Funds:
  • Diversified, low-cost, "set it and forget it" solutions for most investors.
  • “How much can I save? And when do I think I need the money?” If you can answer those questions, a target retirement index fund can be the solution.” – Bo [12:31]
• Memorable Quote:
  • “You don’t have to try to pick the next, latest, greatest individual stock. You just need to be the market.” – Brian [10:14]

4. Mistake #4: Investing in the Wrong Place

[14:48 – 19:06]

• Many new investors skip over tax-advantaged accounts and go straight to regular brokerage accounts.
• The “Financial Order of Operations” ensures tax efficiency: maximize employer-sponsored accounts, contributions to Roth/HSAs, and only then use after-tax brokerage accounts.
• The Three Bucket Strategy:
  • Tax-deferred: Traditional 401(k)s/IRAs—grow tax-free, taxed upon withdrawal.
  • Tax-free: Roth accounts—no deduction up front, but tax-free growth and withdrawals.
  • After-tax (taxable): Flexible, good for dividends and capital gains, but less tax-efficient.
• Memorable Explanation:
  • “The government’s trying to incentivize this behavior. They give you a deduction not only on the contribution, not only do they not tax you on the growth, they not only don’t tax you as you pull the money out. These [HSAs] are incredibly valuable.” – Brian [17:50]

5. Mistake #5: Not Asking for Help When Needed

[19:06 – 26:42]

• As accounts and options grow, so does complexity—plus emotional decisions can sabotage results.
• Behavioral Risk: Most finance mistakes are behavioral; sell-offs in panic (“panic sell”) can devastate your plans.
• Missing the Best Days Costs You:
  • $10,000 invested in the S&P 500 (1988–2023) becomes $418,000 if untouched; miss the 5 best days, and it drops to $264,000. Miss the 50 best, $32,000. – Bo [20:43]
• “When in doubt, zoom out. Even these things that seem catastrophic in the moment ... if you can just hang on ... you’re going to be a-okay in the long term.” – Brian [21:53]
• When Should You Hire an Advisor?
  1. Complexity: “When complexity has found you.”
  2. Busyness: “You ... don't have the time or the attention to ... give your financial life the focus that it deserves.”
  3. Gravity: “When the gravity of your decisions has become so big ... I don’t want to begin making them on my own.” – Bo [24:44]
• “Success creates complications. And when those complications happen, once again, the porch light will be on. We'll be waiting for you.” – Brian [25:28]

Notable Quotes & Memorable Moments

• On time and compounding:
  • “Time can be your absolute best ally. But if you wait, it begins working against you. And the numbers show that.” – Brian [04:28]
• On resisting trends:
  • “While there may be a case for cryptocurrency ... that's probably not where your first dollars ought to be going.” – Bo [08:17]
• On setting and forgetting:
  • “Target date index funds ... create a set it and forget it type solution.” – Bo [12:31]
• On emotional investing:
  • “If there is, the market is going down 20, 30, 40% like it did in 2008. You buy, panic, sell. That is an absolute disaster.” – Brian [19:34]
• When to seek help:
  • “The best thing that I do for clients ... I protect them from themselves.” – Brian [19:34]

Key Takeaways

• Start investing as early as possible to let compounding work for you.
• Lay your financial foundation first: insurance, debt, emergency fund, THEN invest.
• Avoid trendy temptations; stick to proven strategies like index funds and target date funds.
• Be strategic with account types: leverage tax-advantaged accounts for long-term gains.
• Recognize when you need help, especially as your finances become more complex.

Segment Timestamps

• Mistake #1: Not Starting Early – [00:36 – 04:28]
• Mistake #2: Starting Too Soon – [04:28 – 07:23]
• Mistake #3: Wrong Things – [07:23 – 14:48]
• Mistake #4: Wrong Place – [14:48 – 19:06]
• Mistake #5: Not Asking for Help – [19:06 – 26:42]

By following the advice in this episode, listeners can avoid classic pitfalls, maximize their investment success, and build a more confident, worry-free financial future—knowing exactly what to do next and when to seek expert guidance.