Sasha Jovanovic
5 min read
Wall Street’s recent AI boom and the sharp $3.2tn sell off after the US midterm shock have highlighted one clear lesson: capital can move fast, conviction cannot. When sentiment swings, investors often crowd into whatever is fashionable. Founder led businesses are different. Their leaders built the mission and usually think in decades. This article breaks down three such stocks that fit that long haul mindset.
The three stocks highlighted here offer a compelling starting point if you want exposure to founder-led businesses where leadership is personally tied to long-term outcomes. However, if you want the pick of this theme, these 27 top founder-led companies are the best of the best.
Block (XYZ)
Block taps directly into the founder-led theme, with Jack Dorsey still closely identified with Cash App and the Square merchant ecosystem, even as the wider group stretches across payments, banking tools, hardware and crypto.
Block generates about US$9.4b from Square’s merchant services and roughly US$15.9b from Cash App’s consumer finance tools, plus a smaller US$377 million from other ventures, and carries a market value of around US$51.7b.
“The rapid acceleration in new product launches, now supported by an AI native operating model that has lifted code changes per engineer 150% since early 2026 and helped ship 130 Square features in the first half of 2026, points to sustained improvements in Cash App and Square feature velocity that can support higher revenue and operating leverage over time.”
The real swing factor is whether one quiet shift in how Block funds and prices its expanding financial services feeds through cleanly into future margins.
If that funding shift is the real story, the full narrative for Block shows how Block’s model could either quietly reset its risk profile or accelerate its upside.
Oracle (ORCL)
Oracle is a founder guided heavyweight in enterprise software, with Larry Ellison steering its push into Oracle Cloud Infrastructure and autonomous database while a broad portfolio of ERP, HCM, industry applications, hardware and services generated about US$62.8b from cloud and software, US$5.8b from services and US$3.2b from hardware. The group carries a market value near US$362b.
Oracle fits this founder-led theme through Ellison’s long-running grip on the product roadmap, especially around OCI and the autonomous database stack, which underpin how enterprises run critical workloads. That founder imprint matters most when the story hinges on long contracts, heavy data-center spend and multi-year AI infrastructure bets.
