Market Mondays Ep. 297: The Investor’s Roadmap to Winning in the Stock Market

Date: February 17, 2026
Hosts: Rashad Bilal, Troy Millings (“Mike”), Ian Dunlap
Podcast: Market Mondays | Earn Your Leisure (EYL) Network

Episode Overview

This episode focuses on the essential strategies for building wealth and achieving investing success in any market condition. With a big-picture perspective, the conversation covers everything from the discipline and psychology of trading to sector rotations, investment opportunities in AI, the current state of the market, and practical tactics for both beginners and experienced investors. They also answer live listener questions, breaking down real-life dilemmas and investment scenarios.

Key Discussion Points & Insights

1. Community Reflections and Recent Events

Timestamp: 02:35 – 06:45

• The hosts reflect on their return from D.C. and recent EYL community events.
• Emphasis on the value of community, trust, and curating high-quality, educational, and networking experiences.
• Announcements for upcoming Invest Fest and EYL University events, featuring high-profile, hard-to-access speakers.

Rashad (05:55): “We've been blessed again to create that place of trust for people in the community that have something they want to get off their chest.”

2. Key Market Updates & Trading Tip of the Week

Timestamp: 07:09 – 09:44

Market Happenings

• OpenAI acquires Peter Steinberger, keeping OpenClaw open-source.
• Amazon down 17%—worst month since April 2022.
• Nasdaq’s call-to-put ratio at a high, suggesting a possible larger market pullback.

Trading Discipline—Contract Sizing

• Ian stresses the importance of gradually increasing contract size after substantial practice for real market freedom.
• Rule of thumb: 300 practice trades before going live.
• “You can't put a Basquiat on your wall trading one to four contracts.” – Ian (08:37)
• Sizing up should be deliberate, after building discipline and comfort.

3. Discipline & Emotional Intelligence in Trading

Timestamp: 09:44 – 15:50

• Rashad and Ian share hard-won lessons about trading psychology:
  • The urge to go bigger after a win and the need to stay disciplined.
  • Don’t let big gains or losses disrupt your risk management.
  • Maintain a consistent risk profile and avoid over-leveraging even after significant profits.
  • Experience and “preparing for the moment” are crucial—embrace the process before sizing up.
  • Long-term consistency trumps chasing short-term windfalls.

Rashad (11:31): “You should prepare yourself for that moment...it will teach you about grit, about financial intelligence mixed with emotional intelligence.”

4. The Perils and Lessons from Short-Term Trading: Coinbase Example

Timestamp: 15:54 – 22:46

• Rashad details losing a put option on Coinbase despite all indicators predicting a negative outcome.
  • Lesson: Even with perfect research, short-term trades can backfire due to unpredictable after-hour moves and market manipulation.
  • Emphasis on using longer timeframes for puts (month plus) and being careful with catalyst betting.
  • Sometimes the market “punishes” short-term traders regardless of the logic.
  • Connection to futures and the importance of backtesting and stop-loss placement to avoid being “whipped out.”

5. When Should You Sell a Long Term Position?

Timestamp: 24:18 – 27:40

• Only sell if you’ve hit your “freedom number” (your life-changing financial goal).
• The coming years will likely require more capital due to debt/inflation; don’t sell assets prematurely unless there are fundamental, structural changes in the company.
• Use trailing stop-losses (suggested: 25%) to protect against large drawdowns, especially if a company loses its edge or “moat.”
• Example: PayPal down 89% from its peak due to loss of competitive positioning.

6. The Next Big Opportunity: Electronic Design Automation (EDA) Software

Timestamp: 28:05 – 34:02

• The “next AI” opportunity is in the software that trains and powers GPUs: Electric Design Automation (EDA).
  • Core players: Synopsys (SNPS) and Cadence (CDNS).
  • These tools are essential to the continued AI/data center/gaming revolution.
• Rashad: “Write this down: EDA, Electric Design Automation software...that software is what provides a GPU to actually be able to be trained.” (29:58)
• Pullbacks in these software names are buying opportunities, as they have “must-have” status in the semiconductor ecosystem.
• Analogy: Similar to owning both Nvidia and AMD, own both Synopsys and Cadence to cover the full opportunity.
• Example: Following previous “themes”—GPUs, memory (Micron, Western Digital), power (GE Vernova, Caterpillar), EDA software is next.

7. Trading & Investing Education: Community, Dedication, & Realistic Returns

Timestamp: 34:02 – 40:45

• Mike emphasizes the benefit of trading education, options classes, and practical trading calls offered by EYLU.
  • Real trades, transparency on wins and losses, and open community discussion are vital.

Mike (36:59): “One thing about getting rich is that there’s no such thing as getting rich quick. You have to get rich with dedication. But you can get rich if...you are surrounded by the right people.”

8. Risk Management & Portfolio Construction

Timestamp: 40:45 – 43:05

• Set return targets: 100%, 500%, 1000%. Hold long-term, especially to build multi-generational security.
• Anticipate that you’ll need to help family/community in a tumultuous economy.
• Only rotate into “quality” international stocks—stick to proven winners unless you have a compelling thesis.

9. Are There Great $20-and-Under Stocks?

Timestamp: 43:13 – 48:40

• Pushback from listeners wanting cheap, sub-$20 stock ideas.
• Ian strongly advises against chasing low-priced stocks lacking quality leadership, margins, or global strategy.
• He recommends conservatism and seeking value in quality bigger names instead. Most $20-and-under stocks today don’t match past outliers (like AMD at $11 or Palantir).

Ian (45:36): “I'm here to tell you: a lot of these [cheap stocks] are not. They don't have the leadership, the product, the profit margin, the global strategy to do so.”

10. International Stocks in Today’s Market

Timestamp: 48:40 – 52:04

• Now is not the time for aggressive sector rotation into international stocks.
• Most world-class companies are US-based multinationals anyway (with exceptions: ASML, TSMC, Alibaba, Mercado Libre, SK Hynix, Samsung, etc.)
• Emphasize quality, multi-market leaders only; don’t try to “escape” a US pullback by rotating abroad.
• Sector rotation is for large funds, not retail investors managing their own portfolios.

11. Dow 50,000: Has the Market Peaked?

Timestamp: 52:26 – 56:23

• Dow hitting 50,000 is a milestone, but unlikely to be “the” peak—more growth to come.
• Dow composition (industrials, energy, financials, healthcare) makes it robust for the current era.
• Major corporate CapEx (Amazon, Google, Microsoft) suggests ongoing support for related sectors.

Rashad (54:12): “All those things are leading the Dow, and I think the spend, the capex on those things are going to increase.”

12. The Top 10-Only Strategy & Portfolio Diversification

Timestamp: 57:51 – 67:32

• Mike advocates mainly investing in top 10 market cap companies for long-term, big-dollar positions; uses smaller positions/options for up-and-comers.
• Ian and Rashad note that sometimes the next big grower isn’t in the top 10, and it’s important to allow for some calculated risk.
• Keep separate buckets for long holds, trading, retirement, and speculative plays to avoid "contagion" in the portfolio.

Mike (67:32): "It takes a long time to get rich. It takes a short time to blow it."

13. The India AI Impact Summit & Global Tech Shifts

Timestamp: 84:11 – 87:11

• India is on the rise as a major technology hub: hosting the first major AI summit in a developing (emerging) nation, attracting heavyweights (Google, OpenAI, Nvidia, Anthropic).
• US–China tensions lead companies to diversify talent and manufacturing bases to India.

14. Norway’s Tax on Unrealized Gains: A Warning?

Timestamp: 87:11 – 88:31

• Norway institutes a 36% tax on unrealized gains—hosts discuss global experimentation with wealth and capital controls.
• Warn retail investors to watch how governments may respond to growing participation and profits in stock markets.

15. How to Improve Stock Picking & Entry Timing

Timestamp: 88:37 – 92:50

• Ian’s “stock picking” method:

  • Study obsessively (“read everything”), treat investing as a game/sport.
  • Use technical tools: 72 EMA, 200 EMA, 400 EMA for entries.
  • Focus less on finding “the next hot stock” and more on executing well at key market triage points.

• Mike’s “20/30/40 Rule”:

  • If a quality company drops 20%, start entering.
  • 30%: add more.
  • 40%: go heavy — these are rare opportunities in blue-chip names.

Rashad (92:09): “Anytime you buy a depreciating quality asset, the return is going to be greater...this is how you see a thousand, 2,000, 3,000%: you’re buying when it’s depreciated.”

16. Long-Term Simplicity: Just Four Companies?

Timestamp: 92:50 – 93:53

• Ian suggests most investors can build serious wealth by focusing on four first-rate companies and accumulating large positions over time.
• Avoid over-trading and "diversifying" into mediocrity.

17. Leveraging AI & LLM Tools for Investing

Timestamp: 94:32 – 97:53

• All hosts use AI platforms (ChatGPT, Claude, Gemini, Perplexity) for research and analysis and urge the audience to do likewise.
• Investing in premium versions is worth it for better data/privacy.
• Use AI to build custom research workflows and leverage memory features for compounding knowledge.

18. Return on Time: Focus on Your Zone of Genius

Timestamp: 99:01 – 100:52

• Hosts stress focusing on high-value activities—outsourcing tasks outside your core competency (e.g., don’t waste time hanging pictures if you could be earning or learning).
• Mike: “The biggest investment I can make is into myself…I want the highest level performance.”

19. Q&A: Stocks, Sectors, and Market Moves

Timestamp: 103:30 – 116:25

• Topics include:
  • Google’s 100-year bond: Not a major red flag, but warrants tracking.
  • Caterpillar and GE Vernova: Long-term bullish on both as core infrastructure plays—AI is accelerating demand (106:45).
  • Commentary on Palantir, Amazon leadership, and company-specific risks.
  • VRT (Vertiv): Key player in the data center cooling (AI/gpu) story, with recent earnings beats and strong outlook (112:16).
  • Risk considerations for stocks like MicroStrategy (debt-heavy).

Notable Quotes and Memorable Moments

• On the discipline of leveling up as a trader:

  “Once you get two years in, you need to be in that 10 to 15 contract range…You gotta size up.” — Ian (08:21)

• On emotional intelligence in investing:

  “You gotta stay as disciplined as you were when you…got those gains. Risk profile can’t change.” — Rashad (14:22)

• On “the next AI” opportunity:

  “EDA, Electronic Design Automation Software. That software is what provides a GPU to actually be able to be trained.” — Rashad (29:58)

• On dangerous cheap stocks:

  “If Microsoft and Apple are pulling back…this is not the time to play in the bucket of the stocks with deep decay.” — Ian (45:36)

• On only owning four companies long-term:

  “Just select four great companies and get a whole bunch of shares...Master four things to trade and four long-term hold for 10 years minimum—ideally 40.” — Ian (92:50)

• On leveraging AI for research:

  “Phone a friend for real should be your number one brainstorming partner every day for an amazing presentation.” — Ian (57:43)

• On life and wealth:

  “It takes a long time to get rich. It takes a short time to blow it. Remember that.” — Mike (67:32)

Timestamps for Important Segments

• 02:35 — Host reflections, D.C. event recap, importance of community
• 07:09 — Weekly market update / Trading tip: Contract sizing
• 09:44 — Trading discipline, emotional intelligence, sizing up
• 15:54 — Coinbase put option cautionary tale — short-term trading risks
• 24:18 — When to sell? Long-term positions and the “freedom number”
• 28:05 — The next AI sector: EDA software (Synopsys, Cadence)
• 36:59 — Building wealth through dedication, community, and education
• 43:13 — Are there good $20-and-under stocks? (Short answer: probably not)
• 48:40 — International stocks and why most investors should avoid rotating
• 52:26 — Dow 50,000: Market top or further to go?
• 57:51 — Top 10 market strategy & why allocation matters
• 84:11 — India’s AI summit & growing global tech hubs
• 87:11 — Norway taxing unrealized gains: a warning sign
• 88:37 — Blueprint for stock picking and optimal entry levels
• 92:50 — The case for owning just four core long-term companies
• 94:32 — Using AI for investing research and workflow
• 103:30 — Q&A segment (Google bond, industry calls, earnings preview)
• 106:45 — Enduring infrastructure names: Caterpillar, GE Vernova
• 112:16 — The Vertiv (VRT) story and the rise of liquid cooling
• 116:07 — Nvidia & Synopsys earnings preview

Actionable Takeaways

• Take your time and practice before sizing up in trading. Log 300 simulated trades before going live; then tactically increase exposure.
• Long-term success means holding winners for years, not weeks. Pick 4-6 core companies, build large positions over time, and resist the urge to “over-trade.”
• Study the story: Sector leadership, tech infrastructure, and AI enablement are the big themes now and for the next decade. (e.g., EDA software, GPUs, memory, data center cooling)
• Use advanced tools—AI and community—for research and workflow optimization. Pay for premium products; invest in your edge.
• Pay attention to macro risks: Government debt, inflation, and new tax policies can threaten wealth—we’re living in unique times.

This Market Mondays episode is jam-packed with actionable strategies, warnings, and sector spotlights—all designed to help investors build conviction, develop discipline, and capture major themes while avoiding common pitfalls.