Value Investigator
Quality-Growth Investor, Fundamental Research & Portfolio Strategy
Shift4 is about five times cheaper than Microsoft on owner earnings. Owner earnings here are cash flow after stock-based compensation, deducting maintenance capex instead of depreciation and before growth capex, roughly what Shift4 could distribute to shareholders today if it skipped growth investment. x.com x.comÂ
Microsoft's 50% Azure growth and prospect of positive cash flow in 2027 make the stock look bulletproof. Headcount cuts, lower Anthropic spend, a better Copilot routed to cheaper tokens, and coming proprietary chips and model usage add to the case. It should get Apple's multiple plus recognition for cybersecurity. x.com x.comÂ
Shift4 Payments is about 55% undervalued against an estimated fair value near $105 while growing around 30%. It owns the full payment flow from point-of-sale hardware to software, supporting strong take rates and margins. Gross profit grew 34% in 2025, with about 30% guided for 2026, and margins keep expanding under strong management. Risks are integrating its many acquisitions, competition in a payments-only business and about $5 billion of debt that would bite if growth or profits falter. … Show more
Shift4 Payments may look cheap, but payment processing is a margin race to the bottom and a tough business. Companies with much stronger moats are a better use of capital, since paying fair value for a great business beats buying an OK business cheaply. @PronkDaniel notes it is growing strongly at 6.5 times estimated free cash flow while conceding its moat is questionable. x.comÂ
Shift4 Payments looks mispriced. The founder-led payments platform is growing more than 30% yet trades at a single-digit forward P/E. It posted record 2025 results and made major acquisitions in a massive payments market, but the stock is still more than 50% below its highs. x.comÂ
Microsoft is underpriced relative to its fundamentals, which is why Bill Ackman sold Google to buy it. Its P/E has compressed to 23x, the lowest in years, while Azure grows 39% year over year and AI revenue runs at $37 billion annualized, up 123%. A $625 billion revenue backlog supports demand, and $190 billion of capex points to future dominance, not recklessness. x.comÂ
Microsoft's problem is not cash but narrative: down 30% from its highs, it still generates $15B a quarter of free cash flow at peak capex. If Satya Nadella told investors when capex intensity will peak, that one sentence could be worth $500B in market cap. x.comÂ
Microsoft's valuation is starting to look attractive at about 22x forward earnings, a 4.5% earnings yield, for a pristine, wide-moat compounder with secular tailwinds. It remains a cash machine, funding heavy AI and infrastructure spending from its own operations while still generating plenty of free cash flow, without borrowing or issuing stock, even with shares down double digits this year. x.comÂ
Microsoft is a great business but still an expensive bet at $385, because heavy AI capex is eroding free cash flow. Capex was revised to $190B for the year, $43B above expectations, and free cash flow fell to $15.8B. Revenue grew 18% to $82.9B, operating income 20%, Azure 40% and AI run rate reached $37B, with a 47% operating margin. The average analyst target of $560 implies 45% upside only if the AI spending converts on schedule. x.comÂ
Microsoft, one of the best businesses in the world, now trades at 19x forward earnings, the kind of valuation where quality investors start buying. x.comÂ
Shift4 is too cheap at these levels, essentially a private-equity-style vehicle in public markets that is hard to appreciate but runs a good playbook; Jared Isaacman is not selling out down here. Its Global Blue acquisition was poorly timed as US-Iran tensions crush international travel, Fiserv's turmoil hit payments, and AI angst weighs on software. Public investors can also choose easier-to-model stories with cleaner KPIs and capital structures. x.comÂ
