Erik Allebest, CEO of Chess.com, shares his journey scaling the company to over 150 million members and $100M+ revenue without any venture funding. He discusses the challenges of raising money, the impact of not having funds, and his biggest lessons on scaling users with zero budget. He also touches on topics such as parenting, marriage, and the enduring appeal of chess.

David Tisch, Managing Partner of BoxGroup, and Terrence Rohan, Managing Director of Otherwise Fund, discuss the biggest misconceptions in seed investing, including the inefficiency of the market and the importance of being price-insensitive. They debunk the concept of signaling and emphasize the negative impact of reserves. They also highlight the significance of investing in the best companies for great returns and building strong relationships with founders early on.

In this episode, Will Wu, CTO @ Match Group and former VP of Product at Snap Inc., discusses his journey in product development. He shares hiring tips, product review strategies, and the balance between art and science in product decisions. He also explores the collaboration among dating apps and the importance of listening to users. Stay tuned for work from home setup advice and the biggest hiring mistakes.

Dave Kellogg, former CMO of Business Objects and CEO of multiple companies, discusses the flawed nature of CAC payback period and the effectiveness of CAC ratio. He also talks about the importance of gross revenue retention and the biggest mistakes founders make with metrics. Additionally, he shares insights on building and scaling sales teams, CFOs buying new tech, winning renewals, and the strategy of hiring sales reps. The podcast covers topics such as ideal customer profiles, power structures, sales and marketing distinctions, measuring growth, customer success, sales reviews, vertical expansion, AI sales tools, and workflow simplification.

Ryan Akkina, member of the Global Investment Team at MIT, shares insights on how MIT selects venture managers to invest in and the three categories of checks MIT writes into funds. He discusses MIT's approach to building their venture fund portfolio and their strategy for direct investing. Ryan also talks about the challenges of being an LP in today's investment landscape.

Dave Ripley, CEO of Kraken, discusses the flaws in the SEC's approach to crypto regulation and whether Gensler should step down. He also explores the various use cases for crypto beyond store of value and shares insights on the impact of US elections on the crypto market. Additionally, Dave talks about his journey from Boston Consulting Group to CEO of Kraken and the challenges of transitioning into a CEO role.

Sean Murray, CRO @ Greenhouse, shares his expertise on scaling into enterprise successfully, the merging of sales and marketing, and building the best sales team. Learn about reframing problems in sales, challenges of transitioning from PLG to enterprise, and creating a fair hiring process. Discover the traits of effective sales reps and how to maintain team morale.

Adam Fisher, Partner @ Bessemer, shares lessons from his 27 years in venture capital. He discusses the importance of making multiple successful investments rather than relying on one big hit. He prefers to invest in outsider founders approaching a problem with fresh eyes and believes smaller markets are best. The speaker also explores the impact of pattern recognition in investing and the challenges of predicting successful outcomes in early-stage venture capital.

Zaria Parvez, Duolingo's Senior Global Social Media Manager, shares her insights into scaling Duolingo's TikTok to 8M followers. She discusses the power of TikTok, lessons in creating viral videos, measuring success in content, and the challenges of content marketing. The podcast covers ideation process, navigating content creation across platforms, and the importance of hiring troublemakers. Zaria emphasizes the need for adaptability, creativity, and being open to feedback.

Shyam Sankar, Palantir CTO, discusses the broken incentive structure of government defense buying, the impact of conflict and elections on governments' buying process, and the challenges of hiring the best talent. He also emphasizes the importance of creativity over process, the need for reevaluation of defense spending, and the role of AI in solving institutional problems.