Investment Insights and Trends

Delivery is only part of the challenge and risk. That’s true of both the pizza business and healthcare. That insight hit hard at our HealthTech Pizza Tasting during NY Tech Week. With founders, investors, and operators gathered around, we considered key questions. Who’s ready to own the next big slice of risk? What slice of healthcare risk is actually worth owning? And when is one slice better than the whole pie?

Picture this: It’s 9:37 AM on May 14, 2025, and you’re standing in the New Mexico desert watching a small rocket lift off from Spaceport America. What you’re witnessing isn’t just another engine test: it’s history in the making. Venus Aerospace, led by Sarah “Sassie” Duggleby, just achieved what many thought impossible: the first U.S. flight test of her company’s Rotating Detonation Rocket Engine (RDRE). This compact, highly efficient propulsion system is designed to enable hypersonic flight — and redefine how we move through the world.

Courtrooms are slow. Contracts are messy. The workflows? Still rooted in the ’90s despite a few giants like Harvey entering the space. But this won’t be a winner-take-all market. A foundational shift is underway in the legal sector — driven by generative AI, rising cost pressures, and a new wave of founder-led innovation. From deposition prep to document review, automation is no longer a buzzword. It’s shipping and starting to scale.

The past five years have been brutal for cybersecurity leaders. The 2020 SolarWinds breach showed how nation-states could weaponize software supply chains, compromising thousands of organizations across public and private sectors. In May 2021, the Colonial Pipeline ransomware attack shut down nearly half the fuel supply for the U.S. East Coast, triggering widespread gas shortages and panic buying. Just a few months earlier, vulnerabilities in Microsoft Exchange gave attackers access to tens of thousands of email servers worldwide.

Last week, more than 1,500 investors squeezed into a San Francisco venue for a coveted seat at YC’s invite-only Spring 2025 Demo Day. Over six hours, 144 startups delivered rapid-fire, one-minute pitches, each launching just seconds apart. Investors furiously took notes, sized up founders, and fired off intros. Yet Demo Day has evolved beyond a pure deal-sourcing frenzy. By the time the curtain rises, many YC teams already have term sheets in hand from top firms and are well on their way to sealing seed rounds.

At The Greenwich Economic Forum’s inaugural London gathering, three entrepreneurs sat down to discuss what it really takes to build a company in today’s global landscape. What emerged wasn’t just another panel about startup success stories — it was a candid exploration of the fundamental challenges that define entrepreneurship across different markets, stages, and sectors.

Mundus sine caesaribus — Latin for “a world without emperors” — was boldly printed on Jay Graber’s shirt as she took the stage at South by Southwest this March. It wasn’t just Latin flair, but a pointed parody of Mark Zuckerberg’s infamous motto, “aut Zuck aut nihil” (“either Zuck [Caesar] or nothing”). One shirt imagines a world without emperors. The other suggests total domination.

The venture world has long recognized the outsized influence of alumni networks from breakout companies — none more famous than the PayPal Mafia. But today, we’re seeing the rise of a new and potentially more transformative force: the AI Mafia. At Alumni Ventures, we believe the dense networks forming within companies like OpenAI, Anthropic, and others represent one of the most compelling engines of innovation and venture opportunity in a generation. In this piece, we unpack how these “mafias” are forming, why they have structural advantages unlike any previous tech wave, and what this means for the future of startup creation, enterprise adoption, and investment strategy.