
This Week in Startups
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.
Latest episodes

Sep 11, 2024 • 1h 28min
Boom: Supersonic speeds for everyday travel with Blake Scholl | E2006
Blake Scholl, CEO and founder of Boom Supersonic, joins the conversation to unveil the future of aviation with his vision for supersonic travel. They delve into the promising capabilities of the Overture aircraft and share insights from the XB-1 test flights. The discussion highlights the evolution of hardware startups in aviation, the challenges of comfort and cost, and the potential for partnerships with major airlines. Scholl also addresses the importance of innovative design and safety, envisioning a new era of faster, more accessible air travel.

Sep 9, 2024 • 1h 3min
Scaling Childcare with Tech: Winnie.com’s Blueprint for Growing with Purpose & Profit | E2005
Sara Mauskopf, co-founder and CEO of Winnie, a leading childcare marketplace, shares insights on transforming childcare services across the U.S. She discusses their journey from inception to significant growth, including innovative marketing strategies and navigating startup finances. Sara highlights the importance of transparency in metrics and addresses the challenges female founders face in securing funding. She also explores adapting to shifts in childcare demand due to remote work and the balance between profitability and investor expectations.

14 snips
Sep 6, 2024 • 1h 8min
The Rise of Stablecoins with Circle’s Jeremy Allaire | E2004
Jeremy Allaire, Co-founder and CEO of Circle, dives into the fascinating world of stablecoins and their transformative potential in finance. He discusses the evolution from Bitcoin to stablecoins like USDC, highlighting their significance in creating a stable financial future. Allaire explains how stablecoins can integrate with traditional banking systems, offering enhanced transaction efficiencies. He also touches on the impact of regulations and the potential for stablecoins to empower individuals in unstable economies. A captivating look at the future of digital currency!

34 snips
Sep 5, 2024 • 1h 19min
Medium: Reaching Profitability while The Internet is Broken + CorePod | E2003
Tony Stubblebine, CEO of Medium, discusses the platform's innovative approach to combating the broken ad-driven internet. He explores Medium's subscription model that prioritizes quality content and user experience. The impact of AI on content creation is addressed, including challenges with spam and the ethics of data use. Stubblebine also shares insights on Medium's growth, financial milestones, and the importance of diverse perspectives to enhance reader experiences.

11 snips
Sep 5, 2024 • 25min
Fundraising hurdles and M&A slowdown with Becki DeGraw | Wilson Sonsini Startup Legal Basics
Becki DeGraw, a partner at Wilson Sonsini, specializes in startup legal matters, particularly fundraising and M&A. In their discussion, she highlights the current fundraising landscape, marked by down rounds and investor expectations. Becki also delves into the slowdown in M&A activity, impacted by regulatory challenges and antitrust laws. She advocates for reform in M&A regulations to stimulate activity. Additionally, the importance of compliance and cybersecurity strategies for startups is emphasized, making it a must-listen for aspiring entrepreneurs.

52 snips
Sep 4, 2024 • 1h 14min
Superhuman 2.0: The AI edge, top productivity hacks, and the future of email | E2002
Rahul Vohra, Founder and CEO of Superhuman, brings his expertise in email productivity to the table. He discusses the impressive evolution of Superhuman, emphasizing its onboarding strategy and customer feedback's pivotal role. Listeners get a glimpse into live demos showcasing AI features that enhance collaboration. The conversation also dives into AI's transformative impact on team management and internal communication dynamics. With innovative approaches like 'Superhuman for Sales,' Vohra redefines email's potential in boosting productivity.

26 snips
Sep 4, 2024 • 1h 8min
AI Demos: Gemini Gmail, Search GPT, Groq with Voice & Playground | E2001
Sandeep Madre, an AI and Groq expert, shares intriguing insights on the rapid advancements in AI technology. He discusses the integration of generative AI tools in Gmail, enhancing email efficiency while addressing ethical concerns. The conversation also covers AI's transformative role in search engines with Google's new Search GPT functionality. Madre emphasizes the personalization of AI for improved user experience and explores its legal challenges. Additionally, he sheds light on innovative apps that streamline everyday tasks and enhance creativity.

14 snips
Aug 30, 2024 • 1h 37min
Episode 2000! Epic guests, huge news, and how to build a media legacy in 14 short years | E2000
The hosts celebrate their 2000th milestone with reflections on the podcast's evolution over 14 years. They share humorous anecdotes from early days and highlight industry challenges. The impact of storytelling in startups and the fusion of tech with music are discussed. They also touch upon the recent crises in crypto and banking, providing insights into their effects on the tech landscape. Throughout, the importance of teamwork and personal growth shines, alongside heartfelt messages from past guests celebrating their journey.

Aug 29, 2024 • 42min
Startup Pitch Competition: Three founders compete for $25K | E1999
Three innovative founders compete for a $25K investment, showcasing their unique startups. One pitches an AI-driven app revolutionizing running training with personalized coaching solutions. Another presents a platform enhancing the podcast experience through audio intelligence. The third introduces a marketing initiative that transforms outdoor advertising with digital billboards. Insights into startup challenges, pricing strategies, and the importance of community support in entrepreneurship round out this lively competition.

5 snips
Aug 26, 2024 • 1h 16min
The charges against Pavel Durov, the future of encryption, and secondaries are heating up | E1998
Pavel Durov's arrest sparks intense discussions on encryption and freedom of speech. The implications for platforms like Telegram are significant, especially regarding national security. The tension between government surveillance and public privacy rights is scrutinized, shedding light on historical contexts. Additionally, the podcast examines global perspectives on communication technology in light of recent geopolitical events. Finally, it explores the evolving landscape of tech investments and manufacturing, with insights on the challenges startups face in sourcing talent.