In this episode of Stewart Squared, both Stewarts have a wide-ranging conversation that jumps from Claude and Anthropic’s aggressive move against OpenAI employees to the deep history of corporations stretching back to Rome and the East India Company, the mechanics of preferred versus common shares in venture capital, and the recent Figma IPO. Along the way, they contrast speculation and perception in tech markets with hard fundamentals, debate the trajectories of Meta, Apple, and Microsoft in the age of AI, and explore how accounting principles shape both businesses and governments. The discussion widens into geopolitics, from China’s centralized economic power to Israel’s struggle with soft power in the information age, before circling back to the personal lessons Stewart Alsop II learned entering venture capital in the late 1990s.

Check out this GPT we trained on the conversation

Timestamps

00:00 Claude and Anthropic cut off OpenAI employees, sparking a debate on passive vs active aggression, leading into Roman corporations and the East India Company.
05:00 Investors and management are separated through preferred vs common shares, with venture capital structuring conflicts across series rounds.
10:00 Figma’s IPO and Adobe’s blocked acquisition illustrate up rounds, preferences, and investor dynamics when companies succeed or falter.
15:00 Meta’s trajectory from social networks to Oculus, Ray-Bans, and AI labs shows Zuckerberg’s drive to stay relevant, paralleling Microsoft’s rebound under Satya Nadella.
20:00 Public markets, meme stocks, and Apple stock missteps highlight the contrast between speculation, Warren Buffett’s patience, and looming crash fears.
25:00 AI as chaos agent reshapes big tech relevance, with OpenAI’s billion-a-month revenue and Anthropic’s rise pressing Apple, Microsoft, and Meta.
30:00 Gross margins, operating costs, and GAAP reveal how accounting frames strategy, with capitalism vs socialism compared to U.S. government’s one-sided bookkeeping.
35:00 National interest and corporations shift into geopolitics: China’s central planning, Israel’s hard vs soft power struggle, and information age influence.
40:00 Lessons from entering VC in 1997, from missing Amazon and Netflix to early TiVo, reveal timing, firm politics, and venture capital’s internal power struggles.
45:00 Bureaucracies, Trump’s deep state capture, and Curtis Yarvin’s neo-feudal patchwork theory open a discussion on Bukele, Milei, and political reordering.
50:00 Democrats’ weakness, Kamala Harris’s 107 Days, and Project 2025 frame America’s polarization as Trump consolidates MAGA power with no clear opposition.

Key Insights

1. The conversation opens with Claude and Anthropic’s “active aggressive” move to shut off OpenAI employees from using their models, a small drama that sparks a larger reflection on how corporate power plays—whether in Silicon Valley or in Rome—reveal deeper tensions between insiders, outsiders, and the shifting lines of control. Stewart Alsop ties this to the Roman Societas Publicum and the East India Company, early examples of corporations as instruments of state survival and expansion.
2. A major thread is the distinction between investors and management, embodied in the structure of preferred versus common shares. Preferred shareholders gain first rights on exit, creating layered dynamics of power across funding rounds. This preference stack, while protective for early backers, also fosters conflict in down rounds where later investors may hold the leverage.
3. Figma’s successful IPO becomes the case study for how these mechanisms play out when a company is thriving. Blocked by regulators from being acquired by Adobe, Figma proved the strength of building independently. Its up-round IPO ensured all investors, early and late, came out ahead—showcasing the ideal trajectory where preferences resolve smoothly and common shareholders still benefit.
4. The Stewarts contrast perception and reality in markets. Social media companies thrived for two decades largely on speculative momentum, while Meta’s pivot into VR, AR, and AI shows the perpetual need to stay relevant. Zuckerberg’s obsession with avoiding irrelevance mirrors Microsoft’s revival under Satya Nadella, highlighting how tech giants survive through reinvention rather than stability.
5. Investing wisdom emerges in the contrast between venture capital and public markets. Stewart Alsop II admits losing money on Apple stock despite its meteoric rise, underscoring the unpredictability of timing in public equities. Venture capital, by contrast, thrives on entering early—before markets recognize value—while Buffett’s model of patient, long-term ownership represents another, equally elusive, discipline.
6. Accounting principles anchor much of the discussion. Gross margin, operating costs, and GAAP rules determine not just how businesses report health but also how they think strategically. By contrast, the U.S. government’s lack of double-entry bookkeeping shows how politics bends economic logic, treating capital expenditures as simple expenses without long-term allocation.
7. The dialogue crescendos with geopolitics and domestic politics. China is cast as bending capitalism into a tool of centralized control, while Israel demonstrates the limits of hard power when soft power erodes in the information age. Back in the U.S., Trump’s reshaping of the “deep state,” Curtis Yarvin’s neo-feudal visions, and Kamala Harris’s 107 Days underscore the fragility of American democracy, with a weakened Democratic Party unable to counterbalance MAGA dominance.