Stock Newsletter- Stock of the Day- Paypal

PayPal was the king of digital payments. In 2021, it hit a $360 billion market cap, trading at 60+ times earnings. Wall Street loved it. The stock couldn't go down.

Then reality hit. Growth slowed. Apple Pay, Block, and Stripe took market share. The stock crashed 80%+ to $67. By October 2025, PayPal trades at just 15x earnings—a quarter of its old valuation. New CEO Alex Chriss shifted strategy: forget hypergrowth, focus on cash generation and buybacks instead.

The turnaround plan looked solid. Google partnership for distribution. Sold $7B in buy-now-pay-later loans to clean the balance sheet. $6B in annual buybacks. Launched PYUSD stablecoin. The company generates $6-7B in free cash flow with a 10% shareholder yield and 13.8x forward P/E.

Then problems appeared. October 16, 2025: an 84-minute global outage. Third major system crash in under a year. Days before, partner Paxos accidentally created $300 trillion in PYUSD without reserves, causing the token to briefly lose its dollar peg. The stock dropped 5%, then 13% more. $8.2B in shareholder value vanished. The question changed from "Is this the next Apple?" to "Can PayPal even stay online?"

Why This Matters

This isn't just about one company. It's about whether a fallen giant can reinvent itself while fighting off real threats.

  • From growth stock to value play: PayPal traded at 60x+ earnings in 2021. Now it's 15x. The company gave up on hypergrowth and became a cash machine with massive buybacks—like Apple did.

  • From market favorite to reliability crisis: A $300 trillion crypto error and three outages in one year changed the question from 'How fast can you grow?' to 'Can you even stay online?'

  • From $360B to $71B: The 80% crash either created a massive buying opportunity—or exposed a company in terminal decline.

  • From angry shareholders to capital returns: PayPal now returns nearly 10% to shareholders annually through buybacks. But can it afford to fix its infrastructure and return cash at the same time?

The question: Is this an undervalued cash machine ready to double—or a company whose infrastructure problems will eat up all the cash bulls are counting on?

The Roundtable Debate

Opening Remarks

Couch Investor (YouTube Channel — Strong Buy):

"I'm holding shares and call options through January 2027—strikes at $90, $100, and $120. The market is wrong about PayPal. Active accounts hit all-time highs in December 2022 and recovered since. Transactions per user are climbing. Payment values are up year over year. The bearish narrative doesn't match reality. I'm expecting management to beat expectations and raise guidance—the bar is ridiculously low. Watch for Braintree growth, better Venmo monetization, and branded checkout returning to high single-digit growth. Those are the catalysts that change sentiment."

Smart Money Sense (YouTube Channel — Bearish):

"October 16th wasn't bad luck—it's the third major crash in twelve months. Before that: fraud system failure in Germany (August), Braintree API outage (November). This is systematic infrastructure rot. When users can't pay for 84 minutes, they don't wait—they switch to Zelle or Apple Pay. Payments have a six-minute trust window. Go past that and users leave permanently. Fixing this needs $200-370 million upfront plus $25-40 million yearly. That money comes from somewhere—either buybacks stop or growth spending gets cut. The market stopped asking about growth rates and started asking if PayPal can even function."

Valuation Battleground

Stone Fox Capital (Seeking Alpha — Strong Buy):

"The market overreacted to the Paxos error. The stablecoin market doubled recently, and PayPal's PYUSD can capture real share. This wasn't PayPal's operational failure—it was a partner issue that made scary headlines but didn't hurt actual customers. Meanwhile, the stock trades at 12x forward 2026 earnings with 400+ million users and one of the strongest brands in payments. The Google partnership alone could transform distribution. Every dip on technical noise is a buying opportunity."

Mehmood P. Bakhsh (Seeking Alpha — Strong Buy):

"My analysis shows fair value at $143 versus current $67—that's 113% upside. The math is simple: take the free cash flow, apply a reasonable multiple for mature payments companies, and factor in market share gains from omnichannel and Fastlane. The Google partnership validates the strategy. TerraPay opens emerging markets. Selling BNPL loans to Blue Owl means scaling without balance sheet risk. Share count is shrinking from buybacks. This is the best risk-reward in payments."

Arda Solmaz (Seeking Alpha — Buy):

"The narrative needs to change. This isn't 2020's hypergrowth fintech anymore—PayPal is a mature cash generator trading at 10x forward free cash flow. That multiple provides downside protection while the $6B annual buyback drives value regardless of revenue growth. Innovation might lag competitors, but when you're buying cash flows this cheap, you just need sustainability. The market is underpricing stability. Boring is bullish."

Technical vs. Fundamental Divide

MCO Global Equities & Commodities (YouTube Channel — Bullish):

"I bought a starter position as a turnaround play mixing fundamentals with Elliott wave analysis. The business quality is strong: revenue per share growing, EPS around $4.73, ROE near 23%, ROIC at 14.6%. Operating margins of 19% are healthy for payments. Debt-to-equity of 0.56 is conservative. Strong economics plus depressed sentiment creates classic asymmetry—limited downside, big upside if perception shifts. Elliott wave patterns show technical support building for a move toward triple digits."

Mackenzie Sagalos (CNBC Television — Neutral/Cautious):

"The PYUSD smart contract problems are concerning. Analysts found the contract gave one wallet unlimited minting rights—no rate limits, no multi-signature requirements. When Paxos accidentally created $300 trillion in PYUSD, the token lost its dollar peg. A major crypto lender froze all PYUSD activity. The broader crypto market sold off. Yes, this was a partner issue, but it raises questions about PayPal's technical oversight, auditing processes, and risk management. These aren't small concerns when building financial infrastructure."

Strategic Direction & Catalysts

The J Thesis (Seeking Alpha — Buy):

"The Google deal brings massive distribution—Cloud infrastructure, Play Store payments, Ads monetization. That's billions of users globally. Buy-now-pay-later keeps growing with Gen Z. My $95 price target is 43% upside, factoring in execution risk. Yes, regulatory compliance is tough, and PayPal plays second fiddle to Google's core business, but the long-term growth justifies the position."

Analysis Fundamental (Seeking Alpha — Strong Buy):

"PayPal is becoming more than payments—it's building a full commerce platform. Branded Checkout is 29% of payment volume and can return to high-single-digit growth. BNPL provides lending without balance sheet risk after the Blue Owl sale. Crypto enables pay-with-crypto. The most overlooked piece: digital advertising using PayPal's transaction data for targeted merchant ads. Despite leverage concerns and competition, the strategic shift from transaction processor to commerce solution creates multiple growth paths. Margins are improving, and valuation doesn't reflect this optionality."

Dilantha De Silva (Seeking Alpha — Buy):

"CEO Alex Chriss is running the Apple playbook—moving from growth-at-any-cost to disciplined capital returns. PayPal is asset-light and capital-efficient, prioritizing buybacks and potential dividend growth. This pivot from revenue maximization to cash generation is a re-rating opportunity. The market still prices PayPal as struggling fintech when it should be valued as a cash-rich financial utility focused on EPS growth through operational leverage. The Apple parallels from the mid-2010s are striking."

Competition & Market Position

Andres Veurink (Seeking Alpha — Strong Buy):

"CEO Alex Chriss is implementing AI cost optimization and margin expansion that haven't hit the numbers yet. Despite slower payment volume growth, the focus on ROIC and EPS through operational leverage is compelling. My 2026 target of $79-85 is 23% upside. The company is at historic valuation lows while business quality improves. Execution on the transformation will drive multiple expansion as investors recognize the mature model."

Smart Money Sense (YouTube Channel — Bearish):

"Competition fundamentally shifted against PayPal. Zelle hit $1 trillion in 2024—literally double PayPal's volume—and it's free, bank-integrated, and available to 200+ million users. Apple Pay is the default iOS wallet. Stripe owns developer services. Block dominates small business. Each PayPal outage forces users to try alternatives. When your platform is down 84 minutes, merchants and consumers test other options and many never return. Research shows six minutes is the trust threshold—anything beyond that causes permanent switching. PayPal's failures are doing competitors' customer acquisition for them."

Louis Gerard (Seeking Alpha — Hold):

"The $7B BNPL sale to Blue Owl was smart—removes balance sheet risk and shows management makes tough decisions. The scalable model and strong cash generation are positives. But margin compression from pricing pressure is real. I need proof PayPal can hold market share without killing profitability. The Google deal is encouraging, but execution risk is high. Until management shows sustainable competitive advantages through innovation or network effects, I'm neutral. This is a 'show results' story."

Retail Investor Perspectives

Anonymous Long-Term Holder (Cautiously Optimistic):

"Bought at $180, watched it fall to $67. Painful. But I'm not selling. My thesis hasn't changed—PayPal is still the dominant online checkout brand with massive scale. Yes, outages are frustrating, but I think CEO Chriss gets it and will fix infrastructure. The company has the cash to fix issues and keep returning capital. I've been buying small amounts monthly. My cost basis improved from $180 to $105. Options activity shows institutions positioning for upside. Put/Call ratios show excessive bearishness—usually marks bottoms. I'm playing the 3-5 year game."

Anonymous Former Holder (Bearish/Exited):

"Sold after the third outage. Value investing means buying quality at fair prices, not catching knives. The operational problems reveal technical debt that takes years and hundreds of millions to fix. During that time, competitors capture share with better uptime. Bulls focus on buybacks, but buybacks don't matter if you're losing customers to Zelle and Apple Pay. I'd rather pay 25x for a growing, reliable business than 15x for one with existential operational risks. Show me six quarters of flawless execution, then maybe I'll look again. Until then, this looks like a value trap."

Finance Newsletter-Investor Takeaways

Fundamentals

  • Market Cap: $71.2 billion (down from $360B+ peak in 2021)

  • Free Cash Flow: $6-7 billion annually with 8-10% FCF yield

  • Profitability: EPS of $4.73, ROE of 23%, ROIC of 14.6%, operating margin of 19%

  • Balance Sheet: Low debt-to-equity ratio of 0.56; sold $7B in BNPL receivables to Blue Owl Capital for asset-light strategy

  • Active Accounts: At all-time highs (peaked December 2022, since recovered); 400+ million users

Stock Performance

  • Peak: $360B+ market cap (July 2021)

  • Current: ~$67 per share

  • Decline: Down 80%+ from all-time highs; lost $8.2 billion in shareholder value in one week (October 2025)

  • Technical Support: Key levels around $60-65; potential resistance at $75-80

Valuation

  • Current P/E: 16x trailing, 13.8x forward (down from 60x+ in 2021)

  • Forward Multiples: 12-15x 2026 EPS estimates, 10x forward free cash flow

  • Analyst Price Targets: Range from $79 (conservative) to $143 (bull case), with $95-100 as modal estimates

Catalysts

  • Quarterly Earnings: Expected "double beat" with opportunity for aggressive guidance reset

  • Google Partnership: Multi-year deal integrating PayPal across Google Cloud, Play, and Ads platforms

  • Share Buybacks: ~$6B annually with 9-10% shareholder yield; billions authorized, shares outstanding declining

  • Braintree Re-acceleration: Growth without margin deterioration

  • Venmo Monetization: Continued improvement in Gen Z engagement

  • Branded Checkout: Return to high-single-digit growth (currently 29% of TPV)

  • Crypto/Stablecoin Growth: PYUSD expansion as stablecoin market doubles

Risks

  • Operational Reliability: Third major outage in <1 year (84 minutes on Oct 16, 2025); estimated $285-342M in lost payment volume, $8-10M direct revenue loss per incident

  • Infrastructure Costs: Estimated $200-370M upfront plus $25-40M annual to fix reliability issues—diverts cash from buybacks/growth

  • Customer Churn Risk: Even 0.5% user attrition from outages = $50-75M long-term revenue loss per incident

  • Intense Competition: Zelle processed >$1 trillion in 2024 (2x PayPal's volume); Apple Pay, Block, Stripe, Adyen gaining share

  • Stablecoin/Crypto Risk: $300 trillion PYUSD minting error by partner Paxos; smart contract had unlimited minting rights without safeguards; token briefly de-pegged

  • Growth Deceleration: TPV growth slowing; core branded checkout under pressure; margin compression concerns

  • Regulatory Uncertainty: Payments/fintech oversight increasing globally

Stock Newsletter- Reco(not advice)

I see PayPal as a bet on whether operational fixes can happen before competitors take too much share.

The bull case: At 15x earnings with 8% free cash flow yield and $6-7B annual generation, this looks cheap. Google partnership adds distribution. Clean balance sheet after BNPL sale. CEO Chriss running the Apple playbook of cash generation over growth. If infrastructure stabilizes over two quarters while Braintree and Venmo improve, the stock hits $90-100 in 18 months on multiple expansion alone—no heroic revenue growth needed.

The bear case: Three outages in twelve months isn't bad luck—it's infrastructure decay needing $200-370M to fix. That spending competes with buybacks bulls rely on. Zelle doubled PayPal's volume. Each reliability failure permanently converts users. Six-minute trust threshold means 84-minute outages cause lasting damage. Crypto governance issues show weakness in new initiatives. If market share erodes or infrastructure spending kills buybacks, stock drifts to $50-55.

My stance:

  • Momentum traders: Wait for proof. Need two clean quarters (no outages, beats, stable share) before entering. Watch for break above $75-80 with volume. Use 8-10% stops. Risk-reward doesn't favor early entry.

  • Value investors: Consider 2-3% position if you have 18-24 month horizon. Scale in: half at $65-70, add at $60-62. Watch quarterly earnings for infrastructure commentary and market share. If breaks below $58, thesis likely broken. Mental stop at $55.

  • Options traders: Long-dated calls (June 2026, Jan 2027) at $85-100 strikes give leverage if turnaround works. Binary outcome: infrastructure stabilizes and stock re-rates to $100+, or issues persist and options expire worthless. Max 1-2% portfolio in options.

  • Conservative investors: Skip until management shows sustained excellence. If PayPal fixes reliability, stock offers upside from $75-80. Let others take early risk. Revisit Q2 2026 if execution improves.

Bottom line: PayPal is either an undervalued cash cow preparing for $100+ re-rating—or a value trap where competitive losses and fix-it costs kill the thesis before it works.

The next 6-9 months decide. Size positions for the binary outcome: enough to benefit from bulls, not so much bears cause portfolio damage. In payments, trust isn't negotiable—it's everything. Watch management's actions on infrastructure spending versus capital returns for clues.

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