Andy Chen: The Convenient Cofounder Penalty

Andy Chen of Outcast Ventures spent 15 years at Kleiner Perkins and Coatue studying what actually makes startups succeed — and the data surprised him. After analyzing every U.S. IPO and acquisition over $1 billion in the past two decades, Chen found that founders who didn't know each other beforehand built more valuable companies than those who did. He calls the trap the "convenient co-founder penalty." Now he's doing something about it: Catalyst, a co-founder formation program launching this week, brings together pre-vetted, high-caliber talent to find the right match before the company even exists. Chen also discusses the rise of AI-era solo founders, why elite schools don't predict bigger exits, and his own unlikely path — from CIA nuclear weapons analyst to venture capitalist. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

PR Yu is one of the largest solo GPs in the world — a sole decision-maker controlling hundreds of millions of dollars, with ~100 LPs heading into Fund IV who keep coming back. At Yu Galaxy, no partners means no committees, and deals can close in hours. His portfolio spans healthcare, robotics, and AI, anchored by contrarian bets like Leo Cancer Care — a hardware play Sand Hill Road largely passed on, now tracking toward a multi-billion dollar IPO. Yu calls it "ethical capital at speed": the fastest check on the table, without compromising on principle. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

David Spreng has spent a career in the gap between venture capital and the bank down the street. As founder of Runway Growth Capital, he writes $40 million loans to companies that are too established to be called startups and too unconventional to get a traditional bank loan. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Leah Solivan built TaskRabbit from scratch during the 2008 financial crisis, scaled it into a global platform, and sold it to IKEA — then crossed the table to become an investor. What she learned on both sides: venture capital is a system, it runs on incentives, and most founders don't understand it until it's too late. Solivan talks about the hidden competition inside your investor's portfolio, why the system isn't broken — it's doing exactly what it's paid to do — and how founders can use that knowledge as leverage. Plus: why she's looking for someone to build the AI-native version of TaskRabbit. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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.  Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Dr. Christina Smolke runs a brewery, except the yeast isn’t making alcohol. It’s making medicine. At Antheia, Smolke has turned a long-shot Stanford research project into a new way to manufacture critical pharmaceutical ingredients, using biology instead of traditional chemistry.The approach is already being used to produce opioid precursors for Narcan, with more drugs in the pipeline aimed at chronic shortages and supply-chain failures. Smolke talks about regulation, security, and why some of the hardest problems in science are worth chasing—especially when everyone says they won’t work. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.