Chit Chat Stocks – Our First AMA Episode

Date: November 12, 2025
Hosts: Brett Schafer & Ryan Henderson

Overview

In this special Ask Me Anything (AMA) episode, Brett Schafer and Ryan Henderson answer listener-submitted questions spanning AI market bubbles, investing regrets, personal philosophies, and even a little Premier League banter. The episode provides thought-provoking discussion on investing strategy, major market trends, personal routines, and the challenges (and humor) of finding stock market outliers. The conversation is candid, analytical, and peppered with practical firsthand experience.

Key Discussion Points and Insights

1. Is There an AI Bubble in the Market?

(02:45-15:49)

• Main Concern: Both hosts see parallels to historical bubbles, especially the dot-com and telecom booms. There is a disconnect between current AI infrastructure spending (trillions) and present end-market software revenue (tens of billions).
• Leading Indicators:
  • Watch for moderation in capex growth among hyperscalers (Meta, Amazon, Microsoft, Google). A pullback suggests lower anticipated demand, which will trickle down to infrastructure suppliers like Nvidia, AMD, Broadcom, etc.
  • OpenAI’s aggressive infrastructure investments could also be a bellwether—if revenue targets aren’t hit, expect broader impacts.
• Categories of AI Companies:
  • Levered Players: e.g., CoreWeave—high risk, possible bankruptcy if demand falls.
  • Pure Plays with Strong Balance Sheets: e.g., Nvidia—could still see significant drawdowns in a bust.
  • Diversified Players: e.g., Amazon, Alphabet—less risk of existential threat, but may still have substantial earnings volatility.
• Market Psychology: Overconfidence in near-term AI revenue growth feels ominous.
• Historical Parallel:

  "It's a classic, the music is playing, you gotta dance situation." (Brett, 04:11)

• Memorable Moment:

  “There will be companies…that get devastated and go bankrupt and there will be companies that’ve got a rough five to 10 years. That’s my forecast.” (Ryan, 04:45)

• Advice: Consider shifting away from infrastructure bets to likely beneficiaries once the hype fades, e.g., digital platforms that leverage rather than build AI infrastructure.

Notable Recommendation:

• Read Sparkline Capital’s research on the AI bubble (13:40).

2. Biggest Investing Regrets

(15:49-21:36)

• Brett’s Regrets:
  • American Express: “Patting the table” in 2023 (~$150) but failed to pull the trigger; now >$362.

    “Missed a great opportunity to hop on a never sell train.” (Brett, 15:54)

  • Rocket Lab: Early bull, didn’t buy due to hesitancy over speculative positions. Now the stock has massively appreciated.
• Ryan’s Regrets:
  • Uber: Understood the business, watched Dara’s leadership, but was scared by prior narrative of spending and missed the turnaround.
  • Interactive Brokers: Guest Luis Sanchez pitched at market bottoms in Jan 2023. Ryan liked the thesis but didn’t act. Now, it’s up 259%.

    “People come on as podcast guests and pitch these ideas, they serve them to us on a platter.” (Ryan, 18:41)

3. Most Attractive Non-AI Trends

(21:36-24:53)

• Brett: Neobanks stealing market share from legacy banks thanks to higher-yield savings and digital presence. Big banks slow to adapt, branches increasingly irrelevant.
• Ryan: Digital remittances; the shift from cash to app-based global money transfers. Remitly and Wise poised to win as borderless work picks up.

  “Still a huge portion of remittances today are cash transfers. I cannot imagine that’s true a decade from now.” (Ryan, 23:44)

4. Stocks the Market Has Bafflingly Wrong (Both Long and Short)

(24:53-33:17)

• Brett (Bullish): Airbnb—can’t understand the hate; sees clear margin expansion, global diversification, strong buyback program.
• Brett (Bearish/Confused): Apple, Tesla, Palantir, “quantum players,” EVTOLs, nuclear startups—massive valuations with little or no revenue.
• Ryan (Bullish): Google (six months ago), but now also likes Philip Morris International (PMI)—expects growth in reduced-risk products with all the scale and advantages of traditional tobacco.
• Ryan (Bearish/Confused): Apple, for its “set it and forget it” status.

  “People buy without even looking—Apple is such a large component of so many retirees’ portfolios... I just don’t think growth is as high as people think.” (Ryan, 32:12)

• Memorable Exchange:

  “I don’t get the hate for Airbnb… clear path to steadily grow revenue… I’m surprised it isn’t trading 40 or 50 times earnings.” (Brett, 25:56)

5. Buy/Sell Process: Theses & KPIs

(33:17-39:30)

• Brett: Writes a 2-3 paragraph thesis answering:
  1. Do I trust management?
  2. Is there a (potentially widening) moat?
  3. Is it cheap?
  • Tracks 2-4 KPIs per business quarter-to-quarter (ex: for Airbnb, monitors supply, nights booked, gross booking value).
• Ryan: Focuses on projected 5-yr out earnings; only interested if trading at <10x those earnings. KPI tracking is typically functionally the same, using tools like Fiscal AI.

“Once you can succinctly write your entire thesis in less than a page, you know it very well.” (Ryan, 39:30)

6. The Crypto Leverage Question

(40:09-42:42)

• Both respond with disinterest: Crypto leverage doesn’t concern their investing universe. Speculators will lose money; lesson for others.
• Simple advice: “Never go on huge amounts of margin…please do not go 20x margin if a broker lets you do that.” (Brett, 42:42)

7. Portillo's Update (Down Stock, Staying Put?)

(42:42-44:33)

• Brett: Still holding; thinks it’s cheap, likes management changes, sees activist potential but acknowledges sector-wide malaise and risk of a “take under.” Not adding, but content to let position ride.

  “A couple are going to be losers. That’s fine. I’m just going to hold on to the ones that… turn into huge winners.” (Brett, 44:33)

• Ryan: Not an owner but sees it as a “compelling setup.”

8. Time Management: Work, Pod, and Stock Research

(44:47-48:10)

• Ryan: Main job at Fiscal AI (≈8 hours/day); pod management (1-2hrs avg.); 30-60min nightly research plus deep dives on weekends. Finds strong overlap between work, pod, and personal investing research.
• Brett: Writes 2-3hrs/day for Motley Fool, spends 3-4hrs reading/researching for all pursuits, and 2hrs working on podcast production—notes efficient workflow as DIY podcasters.

9. The Vision with Nelnet

(48:10-51:31)

• Brett: Sees Nelnet as a “future Berkshire Hathaway,” compounding book value/dividends at double-digit rates for 20 years. Management focused on long-term compounding, indifferent to short-term stock price or value realization.

  “The vision…is I never sell and…pass it on for generations.” (Brett, 49:33)

• Ryan: Praises steady capital allocation, “day by day” opportunity-seeking, and focus on circle of competence.

10. Favorite Investing Resources

(51:48-54:30)

• Podcasts:
  • Yet Another Value Podcast
  • Business Brew
  • Acquired
  • Invest Like the Best
• Newsletters:
  • Ian’s Insider Corner
  • TSOH Investment Research
  • Asian Century Stocks
  • Bardi Ideas
  • Liberty’s Highlights
  • Investing for Beginners / Value Spotlight
• YouTube: The Plain Bagel for general finance education.
• Tip: Keep a dedicated investment research email inbox.

11. Listener Pitches & Community Involvement

(54:30-56:44)

• Hosts are open to call-ins and written pitches for Power Hour, preferring pre-recorded submissions or elevator pitches instead of live calls.

12. Vibes Investing and Anecdotal Evidence

(56:44-59:33)

• Both do it occasionally, but only if anecdotes can be meaningful and later backed by data. They recall successful “vibes investing” on products like ZYN (nicotine pouches); warn of biases in consumer/apparel investing.
• Wisdom:

  “Take the anecdote, back it up with the data. Those can be some good investing opportunities.” (Brett, 59:33)

13. How Did the Hosts Meet?

(59:48-61:24)

• Met as kickers at Washington State University football team; bonded over investing talk during the 2017 crypto bubble.
• Started the podcast as a way to differentiate from the limited stock research pod landscape at the time.

14. Professional Goals

(62:03-64:15)

• Brett: Long-term goal to grow the podcast/newsletter into a full-time business, possibly with other entrepreneurial ventures later on.
• Ryan: Also enjoys Fiscal AI work but sees value in building the community, funneling ideas through the podcast, and potentially exploring small business ownership in the future.

15. Premier League Predications (For Fun)

(64:15-65:10)

• Ryan: Arsenal as a realistic winner, “Bournemouth” as a dark horse.
• Brett: Leeds United, in jest.

Notable Quotes

• “Industrial bubbles: overestimate the impact in the short term, underestimate in the long term. I see no reason why this is different.” (Ryan, 04:32)
• “If you know exactly what the leading indicator is going to be, you could have a very good time shorting these companies.” (Brett, 07:01)
• “Buy attractive investments as they come along, assuming they fit within the circle of competence.” (Ryan, 50:33)
• “Investing is just really about understanding the world around you.” (Ryan quoting Jason Moser, 57:27)

Timestamps for Major Segments

• [02:45] – AI Bubble Risks & Leading Indicators
• [15:49] – Biggest Investing Regrets
• [21:36] – Bullish Non-AI Trends
• [24:53] – Market Mispricings (Bullish/Bearish)
• [33:17] – Writing Investment Theses & KPIs
• [40:09] – Thoughts on Crypto Leverage
• [42:42] – Portillo’s: Down But not Out?
• [44:47] – Daily Work & Research Routine
• [48:10] – The Long-Term Vision for Nelnet
• [51:48] – Favorite Investing Channels & Newsletters
• [54:30] – Listener Involvement on the Podcast
• [56:44] – Vibes (Anecdotal) Investing
• [59:48] – How the Hosts Met
• [62:03] – Professional Goals
• [64:15] – Premier League Predictions (For Fun)

This summary captures all the essential discussion points, reflects the hosts’ original conversational style, and provides both philosophical and practical takeaways for listeners, whether new or long-time fans.