Earn Your Leisure Podcast – Investor Daily: Is Now the Time to Buy Oracle? Cloud Profits & Risks

Hosts: Rashad Bilal and Troy Millings
Date: December 17, 2025
Episode Theme:
A deep dive into Oracle's recent stock pullback and the broader landscape of cloud profitability, with nuanced discussion on investment timing, cloud infrastructure growth, company fundamentals, and the role of corporate/government relationships.

Episode Overview

In this episode of Earn Your Leisure, Rashad Bilal and Troy Millings, joined by two Stock Market Analysts, break down Oracle's current position in the stock market following its recent pullback. The focus is on whether now is the optimal time to invest in Oracle, the timeline of profitability for cloud services, understanding the risks involved, and how Oracle fits among the cloud computing giants. The speakers also touch on the market’s evolving perception of Oracle and the impact of political connections and sentiment.

Key Discussion Points & Insights

Oracle’s Stock Pullback & Entry Price

• Immediate Sentiment:
  • Despite recent pullback, Oracle is not necessarily a buy right now—waiting for more favorable pricing is advised.
• Technical Analysis:

  “I think you definitely need to wait to … at least 160 before you are willing to pull the trigger.” — Stock Market Analyst 2 [03:58]

  • Uses Fibonacci retracement and the 400-day EMA (Exponential Moving Average) as guide markers.
  • Analyst suggests Oracle is “underneath that 50 mark ... not a good sign” but sees potential starting at $160/share.
• Cautionary Note on Expectations:

  “We have to stop looking for companies to give Nvidia-like returns that are not Nvidia.” — Stock Market Analyst 2 [04:27]

Cloud Profitability Is Future Dated

• Timeliness of Returns:

  “Cloud profitability is future dated … it takes time.” — Stock Market Analyst 1 [05:20]

  • Although Oracle’s cloud business is growing (from 32% to 39–40% of revenues), realized profits are lagged due to high capital expenditures (capex).
• Historical Comparisons:
  • Draws parallels to Amazon AWS and Google Cloud, noting both took years before cloud segments were profitable.
  • Oracle shifted to cloud in 2018; still in the capex-heavy, margin-thinning phase.

Oracle Among Cloud Giants

• Current Position:
  • Oracle sits as the #4 player in U.S. cloud, #5 globally.
  • Analyst compares Oracle’s present phase to Microsoft Azure’s earlier journey:

    “Their market was unsure if the company could really pivot from being a software to a cloud service. You know what that company’s name was?... Azure by Microsoft.” — Stock Market Analyst 1 [12:14]

• Forecast:
  • Oracle’s repeated reinventions (enterprise software → subscriptions → cloud, now AI-focused services) are highlighted as a sign of adaptability.
  • The strategic pivot is labeled “still in transition,” with future profitability contingent on continued execution in cloud and AI.

Technical Markers & Sentiment

• Key Levels:

  “Oracle is sitting at 183.82 [its 400-day EMA] ... which is a sign.” — Stock Market Analyst 1 [13:12]

  • The technical picture signals caution but not disaster.
• Market Sentiment Shift:
  • Discusses “negative sentiment around Oracle” vs. earlier positive buzz for names like Tesla.
  • Notably, credit default swaps have spiked, reflecting investor concern over Oracle’s ability to manage debt [13:40].

Corporate/Government Ties and Influence

• Larry Ellison’s Influence:

  “Will people be so pro-Oracle if he didn’t have Trump in his back pocket? … But the stock was not a tech darling.” — Stock Market Analyst 2 [14:22]

  • Oracle’s founder Larry Ellison’s political connections, especially his alignment with the Trump administration, have aided in landing major government cloud contracts (TikTok, OpenAI’s Stargate).
• Political Patterns:

  “Have we seen a clear pattern of how he makes sure that the people that are closest to him and take care of him are being taken care of? 100%.” — Stock Market Analyst 1 [15:13]

  • The panel suggests these connections are significant factors in Oracle’s recent business fortunes, particularly around federal cloud contracts.

Notable Quotes & Memorable Moments

• “I think you definitely need to wait to … at least 160 before you are willing to pull the trigger.” — Stock Market Analyst 2 [03:58]
• “Cloud profitability is future dated … it takes time.” — Stock Market Analyst 1 [05:20]
• “We have to stop looking for companies to give Nvidia-like returns that are not Nvidia.” — Stock Market Analyst 2 [04:27]
• “Their market was unsure if the company could really pivot from being a software to a cloud service. You know what that company’s name was?... Azure by Microsoft.” — Stock Market Analyst 1 [12:14]
• “Oracle is sitting at 183.82 [its 400-day EMA] ... which is a sign. … Oracle is not going anywhere.” — Stock Market Analyst 1 [13:12]
• “Will people be so pro-Oracle if he didn’t have Trump in his back pocket?... But the stock was not a tech darling.” — Stock Market Analyst 2 [14:22]
• “Have we seen a clear pattern of how he makes sure that the people that are closest to him and take care of him are being taken care of? 100%.” — Stock Market Analyst 1 [15:13]

Timestamps for Important Segments

• [03:41] - Oracle’s stock pullback and entry price discussion
• [05:20] - Cloud profitability timetables; investment patience required
• [10:51] - Historical evolution of cloud (Amazon, Google, Microsoft, Oracle)
• [12:14] - Parallel to Microsoft Azure’s cloud journey
• [13:08] - Oracle’s technicals and current chart position
• [14:22] - The Ellison–Trump connection, government contracts, and political influence

Tone and Takeaways

The hosts and analysts deliver their analysis in a pragmatic, data-driven tone, mixing technical stock commentary with accessible anecdotes and historical references. They repeatedly stress the importance of patience, realistic expectations, and the need to avoid chasing yesterday’s tech returns.

Summary Judgment:

• Oracle is in a necessary but challenging investment phase—growth and profitability in cloud will take time.
• Currently, a wait-and-see approach, potentially eyeing an entry at $160/share, is advisable.
• Oracle, aided by powerful political and corporate connections, is likely to remain a major player in cloud and AI, but immediate returns should not be expected.
• Investor caution is warranted both by technical indicators and shifting market sentiment.