Ryan Denehy, CEO of Electric, shares insights from his entrepreneurial journey. He reflects on selling his first startup to USA Today and facing financial struggles while launching Electric. Ryan emphasizes the importance of a clear sales pipeline and avoiding buzzwords in marketing. He discusses the challenges of solo founding and building a strong board, highlighting the impact of financing dynamics and the necessity of strategic hiring. Automation in IT management is also explored, showcasing how technology can simplify complex tasks for businesses.

Frank Rotman, Co-Founder and CIO of QED Investors, shares his journey from launching Capital One to shaping the fintech landscape. He discusses the evolution of financial services over 30 years, emphasizing customer-centric innovations. Rotman also analyzes crucial valuation strategies for emerging managers and the importance of understanding local markets when investing. He highlights the successes of Nubank and offers insightful advice on navigating the complexities of fintech and compliance in today's digital economy.

Yossi Levi, the visionary behind Car Dealership Guy, shares his journey from a family car lot to a $28 million business and founding Gettacar. Topics include innovative marketing strategies, hard lessons in product-market fit, and building a lean B2B media empire.

Guest Edwin Dorsey, author of The Bear Cave, discusses short selling, finding bad companies, using FOIA requests, corporate red flags, targeting minorities, and newsletter growth strategies. He shares insights on researching companies, exposing unethical practices, and leveraging customer sentiment. The podcast also explores short selling mechanics, customer sentiment impact on companies, insider selling significance, building newsletters, and exposing fraudulent practices in public companies.

Lisa Wehden, Founder of Plymouth, talks about the O1A visa for talented individuals, the challenges of US immigration, and her unique journey. She discusses raising grant money, breaking into Silicon Valley, and the importance of talent in AI development.

Melissa Cash, Co-founder of Pok Pok, discusses creating non-addictive kids' apps, pricing strategies, waiting to launch on Android, and lessons learned from working at Disney. She shares advice on starting a company, fundraising tactics, building a network, and meeting people at events.

Founder Ed Sim discusses inception stage investing, themes boldstart invests in, the 5 P’s of early stage investing, importance of board members, fundraising challenges, building customer relationships, and the evolution of boldstart ventures from $1M to $850M AUM.

Nilam Ganenthiran, ex-Instacart Chief Business Officer shares insights on scaling Instacart to $10B, signing top grocers, customer research strategies, and launching Instacart's ad network. He discusses board responsibilities, navigating financial challenges, and optimism about generative AI. Engaging tales include cold calling Wegman's and catching an Uber in suits on the highway.

Ankur Goyal, CEO of Braintrust, discusses the importance of LLM evals, having two AI roadmaps, and the impact of AI on software development. Topics include AI advancements, tool calling, and advice for young software engineers. Goyal shares insights on selecting AI models, staying updated on AI developments, and the significance of purpose in career growth.

Alan Feld, Founder of Vintage Investment Partners, discusses the value of VC funds, importance of differentiation, and lessons from 21 years of investing. Topics include fund size impact on returns, buying secondaries, successful entrepreneurs' traits, and advice for raising a VC fund.