When Should You Turn Bearish on the Stock Market?
Jul 29, 2026 · 50 min · 13 segments
On episode 233 of Ask The Compound, Ben Carlson, Duncan Hill, and Josh Brown tackle your investing and financial planning questions, including whether Shake Shack's recent collapse is a buying…
On episode 233 of Ask The Compound, Ben Carlson, Duncan Hill, and Josh Brown tackle your investing and financial planning questions, including whether Shake Shack's recent collapse is a buying opportunity, how active management fits alongside indexing, what would actually make a long-term bull turn bearish, how to promote disciplined investing in a speculative market, and whether an expected inheritance should influence your financial plan. They discuss: - Is Shake Shack a value opportunity after its earnings collapse? - Why active management and indexing aren't mutually exclusive - What would make a long-term investor turn bearish? - Teaching long-term investing in a market driven by speculation - How to think about a future inheritance without letting it change your financial decisions today This episode is sponsored by Betterment Advisor Solutions. Learn more at: https://betterment.com/advisors Compound Merch: https://idontshop.com/ Submit your Ask The Compound questions to [askthecompoundshow@gmail.com](mailto:askthecompoundshow@gmail.com)! Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get updates on the latest merch drops, and more! https://www.thecompoundnews.com/subscribe 🎥 Watch this episode on YouTube: https://youtu.be/QwGFC5M14fU Talk with us about your portfolio or financial plan here: http://ritholtzwealth.com Investing involves the risk of loss. This podcast is for informational purposes only and should not be or regarded as personalized investment advice or relied upon for investment decisions. Ben Carlson, Duncan Hill and Bill Sweet are employees of Ritholtz Wealth Management and may maintain positions in the securities discussed in this video. All opinions expressed by them are solely their own opinion and do not reflect the opinion of Ritholtz Wealth Management. See our disclosures here: https://ritholtzwealth.com/podcast-youtube-disclosures/ The Compound Media, Incorporated, an affiliate of Ritholtz Wealth Management, receives payment from various entities for advertisements in affiliated podcasts, blogs and emails. Inclusion of such advertisements does not constitute or imply endorsement, sponsorship or recommendation thereof, or any affiliation therewith, by the Content Creator or by Ritholtz Wealth Management or any of its employees. For additional advertisement disclaimers see here https://ritholtzwealth.com/advertising-disclaimers Learn more about your ad choices. Visit megaphone.fm/adchoices
On episode 233 of Ask The Compound, Ben Carlson, Duncan Hill, and Josh Brown tackle your investing and financial planning questions, including whether Shake Shack's recent collapse is a buying…
