Sand Hill Road

Summary: Jack Leeney, partner at 7GC, shares insights from his career at Morgan Stanley — where he worked on IPOs for Tesla, LinkedIn, and Facebook — to his current role investing in AI. He breaks down how IPO pricing works, why the public markets have shrunk, and why smaller IPOs still matter. He discusses key 7GC investments including Hims (telehealth), Jackpocket (digital lottery, acquired by DraftKings), and Anthropic (enterprise AI). Jack explains why Anthropic's B2B focus gives it a compelling edge, and why true enterprise-wide AI adoption, currently only ~10% of Fortune 500 companies, represents a massive opportunity over the next decade.

Alice Bentinck discusses how Entrepreneurs First helps someone to go from “no team, no idea” to funded company. EF has helped create companies now collectively worth more than $10,000,000,000 and many participants go from zero to raising $2-15 million from top-tier VCs within months. Bentinck argues that capital is the easiest part of the journey, while co-founder fit, community, and early guidance are what really accelerate success.

AI may feel new to many investors, but Glasswing Ventures founder Rudina Seseri has been betting on it for more than a decade. In this episode, she breaks down how Glasswing evaluates AI startups, why workflow and productivity are key entry points, and what founders still get wrong. Plus, her unlikely journey from a teenage immigrant to a leading AI investor.

Adeo Ressi says his organization helps launch between 60 and 70 percent of new venture capital firms worldwide. In this episode, the Decile Group and VC Lab founder explains why starting a VC fund is far harder than most people expect, why big institutions rarely back first-time managers, and why fundraising is really a numbers-driven grind. Ressi also argues that venture capital remains concentrated in a small number of cities — and that expanding it to hundreds more could reshape who gets funded and where innovation happens.

Alex Halliday made his first fortune at 15 building fan sites in the early web. Now he’s back at the center of another digital reset — helping brands survive AI-driven search. In this episode, he explains why “information gain” beats spam, why Google is under threat, and how AirOps grew from Series A to B in record time as CMOs woke up to the danger.