Michael Burry Bets on PayPal and Other Software Stocks
Written by Emily J. Thompson, Senior Investment Analyst
Updated: Apr 23 2026
0mins
Should l Buy PYPL?
Source: Fool
- PayPal Investment: Michael Burry has initiated a 3.5% position in PayPal, which has fallen below $50 per share due to AI concerns; however, its prudent stock-based compensation policy and discounted valuation make it attractive in the competitive digital payments market.
- Salesforce Outlook: Burry plans to increase his stake in Salesforce, which has dropped nearly 30% this year, yet its 23% share of the global CRM market and AI-driven Agentforce product provide a competitive edge, with the stock currently trading at 14 times forward earnings.
- MSCI Potential: Burry also intends to buy MSCI, which has risen 6% this year; despite facing AI competition in financial research tools, its current price-to-earnings ratio of 31 is below the five-year average, indicating potential value.
- Market Dynamics Analysis: Burry views the recent sell-off in software stocks as a
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Analyst Views on PYPL
Wall Street analysts forecast PYPL stock price to rise
29 Analyst Rating
6 Buy
19 Hold
4 Sell
Hold
Current: 45.440
Low
51.00
Averages
72.86
High
100.00
Current: 45.440
Low
51.00
Averages
72.86
High
100.00
About PYPL
PayPal Holdings, Inc. offers a technology platform. The Company’s products are designed to enable digital payments and simplify commerce experiences for consumers and merchants to make selling, shopping, and sending and receiving money simple, personalized, and secure, online or offline, including mobile. It provides consumers with a digital wallet that enables them to send payments to merchants securely using a variety of funding sources, which include a bank account, a PayPal or Venmo account balance, its consumer credit products, a credit card, a debit card, certain cryptocurrencies, or other stored value products. It operates a global, two-sided network at scale that connects consumers and merchants with 434 million active accounts across approximately 200 markets. Its brands include PayPal, Braintree, Venmo, Xoom, Hyperwallet, PayPal Zettle, PayPal Honey, and Paidy. It offers financing products through the PayPal Working Capital (PPWC) and PayPal Business Loan (PPBL).
About the author

Emily J. Thompson
Emily J. Thompson, a Chartered Financial Analyst (CFA) with 12 years in investment research, graduated with honors from the Wharton School. Specializing in industrial and technology stocks, she provides in-depth analysis for Intellectia’s earnings and market brief reports.
- AI Training Initiative: PayPal's partnership with Anthropic introduces the 'AI Fluency for Small Business' online certification course, aimed at helping 82% of small businesses recognize the importance of AI and implement it successfully, despite 73% lacking training and resources, highlighting a significant market demand for AI education.
- Comprehensive Curriculum: The course consists of nine video lessons utilizing the '4D AI Fluency' framework to teach users how to use AI safely and effectively, reflecting PayPal's ambitious goal to provide digital skills training to 25 million people by 2030.
- New Tool Launch: The collaboration also introduces the 'Claude for Small Business' plugin, allowing Anthropic's AI assistant Claude to integrate directly with PayPal's platform, designed to automate administrative tasks like invoicing and refunds, although all financial transactions will still require human approval to ensure security.
- Accelerated Strategic Shift: Under CEO Alex Chriss, PayPal is transforming from a traditional payments processor to an 'AI-first' financial services company, having recently completed one of the largest data migrations in corporate history to Google Cloud, enabling real-time AI insights that drive business growth.
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- Course Launch: PayPal, in collaboration with AI giant Anthropic, has introduced a free online artificial intelligence course aimed at small businesses, targeting the empowerment of 25 million individuals with essential skills for thriving in the digital economy.
- Market Potential: Anthropic's launch of the Claude for Small Business model aims to tap into a market that has underutilized AI tools compared to larger enterprises, highlighting a strategic focus on supporting small businesses.
- Rich Course Content: The course comprises nine lessons delivered through videos by AI fluency researchers and small business owners, having already provided practical training to over one million learners, thereby enhancing small businesses' success in AI adoption.
- Fee Waiver Agreement: PayPal has agreed to waive $30 million in transaction processing fees to settle a Department of Justice investigation into its
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- Settlement Fee Waiver: PayPal will waive approximately $30 million in transaction processing fees to settle a Department of Justice investigation into its 'DEI Investment Program,' which aims to support minority-owned businesses, reflecting the company's proactive compliance stance.
- Launch of Small Business Initiative: As part of the settlement, PayPal is required to launch a new Small Business Initiative that excludes criteria based on race, national origin, or other protected characteristics, aiming to promote broader economic opportunities and enhance its competitiveness in the small business market.
- Background on Economic Opportunity Fund: The Economic Opportunity Fund, launched by PayPal in 2020 with a $500 million commitment to invest in black and minority-owned businesses, is not subject to fines in this settlement, indicating that the company was not found in violation of the Equal Credit Opportunity Act.
- Government Regulatory Warning: DOJ Acting Attorney General Todd Blanche warned that all American corporations will face aggressive enforcement if they use race or national origin to discriminate against qualified Americans, highlighting the government's heightened focus on corporate compliance.
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- Settlement Amount: PayPal has agreed to pay $30 million to settle a U.S. Department of Justice investigation into its investment program, which was deemed 'unlawful' and 'discriminatory,' directly impacting the company's financials.
- Investigation Background: The DOJ highlighted that PayPal's investment initiative aimed at Black and minority-owned businesses was implemented in a manner that exhibited systemic discrimination, potentially leading to long-term negative implications for the company's social responsibility and brand image.
- Legal Consequences: This settlement serves not only as financial restitution for past actions but may also compel PayPal to enhance compliance measures in the future to prevent similar legal issues, thereby influencing its operational strategy.
- Market Reaction: Although the settlement amount is relatively small, this incident could raise investor concerns regarding PayPal's social responsibility, potentially affecting its stock performance and market confidence.
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- Regulatory Framework Review: The U.S. Senate Banking Committee is set to meet on May 14 to discuss the 'Clarity Act', a move that could break the legislative deadlock between digital asset firms and traditional banks, and if passed, would provide legal certainty crucial for the industry's future.
- Stablecoin Provisions: A central feature of the bill involves dollar-backed stablecoins, prohibiting crypto companies from offering rewards on idle holdings to prevent similarities with traditional bank deposits, while allowing rewards for active use, which has sparked a last-ditch effort by banking lobbyists to garner Republican support.
- Political Support Requirement: To gain final approval from President Trump, the Act requires support from at least seven Democrats in the Senate, despite the House passing its version last year, with a deadline for Senate approval set for the end of 2026 to send it to the President's desk.
- Opposition Voices: Several Democrats oppose the bill, arguing that its anti-money laundering provisions are too weak and that more should be done to prevent political officials from profiting from crypto ventures, which could impact the bill's chances of passing.
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- Layoff Charges Expected: Cloudflare anticipates incurring charges between $140 million and $150 million due to layoffs, which will be reflected in Q2 earnings, indicating financial strain during its transformation process.
- Performance Beats Expectations: The company reported adjusted earnings of $0.25 per share for Q1, exceeding the expected $0.23, with revenue rising to $639.8 million from $479.1 million a year prior, showcasing strong market performance amid its AI transition.
- Upgraded Future Outlook: Cloudflare raised its 2026 adjusted earnings guidance to between $1.19 and $1.20 per share, significantly above the previous forecast of $1.11 to $1.12, reflecting management's confidence in future performance despite uncertainties from layoffs.
- Market Sentiment Analysis: While Cloudflare's stock has soared 111% over the past year, investor sentiment appears cautious following the layoff announcement, with some analysts suggesting that the cuts may introduce execution risks that could undermine investor confidence.
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