Uploaded May 2026 | Updated September 2026, 2 weeks ago
When is the right time to invest in the market? While we believe time in the market beats timing the market, recent data shows the average equity investor has underperformed the overall market by roughly 5% per year. Financial Advisors, Brian Preston and Bo Hanson, break down the behavioral patterns behind that gap, from loss aversion to overconfidence, and share what a smarter investment strategy can look like in 2026.
Then we answer your personal finance questions live! We cover FOO Step 7, the benefits of ABLE accounts, and rapid fire questions on FIRE paths, company stock purchase plans, and more.
Timestamps
0:00 Everyday Investors Are Beating Professional Money Managers?
10:21 Q&A: Paying Extra to Remove PMI?
13:33 Q&A: Does the 25% Savings Rule Apply to Overtime Pay Too?
19:38 Q&A: I Feel Guilty About a $5K Moose Hunting Trip With My Dad. Should I Go?
25:15 Q&A: Should I Use the Same Index Funds Across My HSA, 529, and Roth IRA?
29:02 Q&A: Can I Front-Load My 401(k) Contributions to Take Summers and Holidays Off?
32:51 Q&A: How Do I Know When I Move From Step Six to Step Seven?
38:55 Rapid Fire: It Does Not Depend
48:45 Maybe It Does Depend: Deeper Dives on the Rapid Fire Questions
58:21 Q&A: When Are ABLE Accounts Appropriate for Families With Disabled Children?
🔗 Financial Order of Operations (FOO) → moneyguy.com/guide/foo
🔗 Millionaire Mission → moneyguy.com/millionairemission
🎓 Brian Preston (CFP®, CPA) and Bo Hanson (CFA®, CFP®) share professional insights to help you own your financial future.
Jump start your journey with our FREE financial resources: moneyguy.com/resources
Subscribe on YouTube for early access and go beyond the podcast: youtube.com/c/MoneyGuyShow?sub_confirmation=1
Connect with us on social media for more content: moneyguy.com/link-in-bio
Take the relationship to the next level and become a client: moneyguy.com/become-a-client
#WealthBuilding #PersonalFinance2026 #RetirementPlanning #FinancialFreedom
When is the right time to invest in the market? While we believe time in the market beats timing the market, recent data shows the average equity investor has underperformed the overall market by roughly 5% per year. Financial Advisors, Brian Preston and Bo Hanson, break down the behavioral patterns behind that gap, from loss aversion to overconfidence, and share what a smarter investment strategy can look like in 2026.
Then we answer your personal finance questions live! We cover FOO Step 7, the benefits of ABLE accounts, and rapid fire questions on FIRE paths, company stock purchase plans, and more.
Timestamps
0:00 Everyday Investors Are Beating Professional Money Managers?
10:21 Q&A: Paying Extra to Remove PMI?
13:33 Q&A: Does the 25% Savings Rule Apply to Overtime Pay Too?
19:38 Q&A: I Feel Guilty About a $5K Moose Hunting Trip With My Dad. Should I Go?
25:15 Q&A: Should I Use the Same Index Funds Across My HSA, 529, and Roth IRA?
29:02 Q&A: Can I Front-Load My 401(k) Contributions to Take Summers and Holidays Off?
32:51 Q&A: How Do I Know When I Move From Step Six to Step Seven?
38:55 Rapid Fire: It Does Not Depend
48:45 Maybe It Does Depend: Deeper Dives on the Rapid Fire Questions
58:21 Q&A: When Are ABLE Accounts Appropriate for Families With Disabled Children?
🔗 Financial Order of Operations (FOO) → moneyguy.com/guide/foo
🔗 Millionaire Mission → moneyguy.com/millionairemission
🎓 Brian Preston (CFP®, CPA) and Bo Hanson (CFA®, CFP®) share professional insights to help you own your financial future.
Jump start your journey with our FREE financial resources: moneyguy.com/resources
Subscribe on YouTube for early access and go beyond the podcast: youtube.com/c/MoneyGuyShow?sub_confirmation=1
Connect with us on social media for more content: moneyguy.com/link-in-bio
Take the relationship to the next level and become a client: moneyguy.com/become-a-client
#WealthBuilding #PersonalFinance2026 #RetirementPlanning #FinancialFreedom
