James Hawkins is the co-founder and co-CEO of PostHog, the open-source product analytics platform built for engineers. He pivoted five times inside Y Combinator's W20 batch before landing on PostHog, then turned a Hacker News launch and a single tweet into a developer cult following and a $1.4 billion valuation. A former marketing operator and self-described 'very bad developer,' Hawkins runs PostHog on radical transparency, tiny autonomous teams, and a refusal to be boring.
Beth Gerstein co-founded Brilliant Earth in 2005 after a personal search for an ethically sourced engagement ring turned up nothing worth buying. An engineer by training (Duke BS at 19, MIT MS, Stanford MBA), she built a company that now generates $422 million in annual revenue and trades on Nasdaq (BRLT). Brilliant Earth is the rare luxury brand that treats supply chain transparency as a marketing advantage rather than a compliance headache - offering Beyond Conflict Free diamonds with traceable origins, lab-grown stones, and recycled metals. Under Gerstein's leadership, the company has donated over $2 million through the Brilliant Earth Foundation, partnered with Dr. Jane Goodall on conservation collections, and expanded to 28+ showrooms while maintaining 14 consecutive quarters of profitability as a public company.
Yinon Weiss is a serial entrepreneur, decorated military veteran, and the Founder and CEO of Stress-Free Auto Care - a tech-enabled auto repair chain with 30+ locations across California and Texas. Before Stress-Free, he co-founded RallyPoint (the 'LinkedIn for the military') and CarDash (a transparent auto repair marketplace that went through Y Combinator S17 and was acquired). A UC Berkeley bioengineering grad with a Harvard MBA, Weiss served 10 years on active duty as a Marine Corps Scout/Sniper Platoon Commander and Army Special Forces officer, earning the Bronze Star before transitioning to Silicon Valley entrepreneurship.
Pat Flynn is an entrepreneur, author, and podcaster best known for founding Smart Passive Income (SPI), a platform where he openly documents the strategies - and the income numbers behind them - that power his online businesses. Laid off from his architecture job in 2008, he turned an e-book about the LEED exam into a career-defining pivot, eventually building a media company with 60 million+ podcast downloads, multiple Wall Street Journal and Amazon bestselling books, a Kickstarter-funded tripod product, and a Pokémon card YouTube channel that became its own standalone business. His signature move: publishing every dollar earned and spent, monthly, in public.