
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

Apr 10, 2022 • 45min
Investing in down rounds (VC School) + The Lightsmith Group Co-Founder Jay Koh (Climate) | E1431
Jay Koh, Co-founder and Managing Director of The Lightsmith Group, delves into the urgent need for investments in climate resilience and adaptation. He discusses overlooked areas like supply chain management and warns against the pitfalls seen in earlier climate investing waves. Koh emphasizes innovative strategies and investment opportunities in climate solutions, especially as communities face increasing challenges from climate change. The conversation reveals both the complexities and the promise of navigating venture capital in the climate sector.

Apr 9, 2022 • 38min
BONUS - Jason on This Week in Startups Australia
Jason Calacanis, an angel investor and entrepreneur renowned for his pandemic predictions, dives into the shifting startup landscape with Mark Pesce. He discusses how startups are adapting to new economic realities, especially in telehealth and online services, while emphasizing the importance of profitability. The conversation highlights the evolution of remote work dynamics, showcasing its impact on employee engagement and fostering a culture of well-being. Calacanis reflects on the resilience of startups amid changes in urban business environments and the growing appreciation for flexible work.

Apr 8, 2022 • 1h 33min
Macro insights with Rose Technology CEO Alex Campbell + TCG Crypto's Gaby Goldberg | E1430
In this episode, Alex Campbell, CEO of Rose Technology and former Bridgewater trader, shares insights on macroeconomic trends, focusing on the Chinese real estate bubble and its effects on Bitcoin. He discusses investment strategies amid global uncertainty, emphasizing the need for diversification and shorting overvalued assets. Gaby Goldberg from TCG Crypto explores the intersection of consumer behavior and crypto investments, offering resources for those new to the space. Together, they reveal dynamics shaping today’s financial landscape.

Apr 8, 2022 • 1h 38min
Portfolio construction, Sequoia's transition & Fast with Acquired.FM + The Dropout: This Week in Streaming with Lon Harris | E1429
Ben Gilbert, Managing Director at Pioneer Square Labs, and David Rosenthal, Co-founder of Kindergarten Ventures, delve into effective portfolio construction and the recent transition at Sequoia Capital. They discuss the downfall of Fast.co and what it means for the venture capital landscape. Lon Harris, a streaming media expert, analyzes the gripping finale of 'The Dropout,' sharing insights into its narrative and the broader implications for future seasons. This rich conversation blends venture capital strategies with engaging media analysis.

Apr 6, 2022 • 1h 11min
Uber travel, OpenAI illustrator, Edit button, CNN+ review + Dune Analytics CEO Fredrik Haga | E1428
Fredrik Haga, CEO and founder of Dune Analytics, dives into the world of on-chain crypto analytics and its importance in promoting transparency. The discussion also covers Uber's expansion into long-distance travel and Twitter's new edit button, revealing the implications for user engagement. Haga emphasizes the significance of real-time data in evaluating the booming NFT market and shares insights on navigating crypto investments. Additionally, they critique CNN+ and suggest strategies for enhancing media engagement.

Apr 6, 2022 • 1h 44min
FB vs. Apple on AR and Ads, Twitter's Future, Conflict, Crypto Regulation with Antonio Garcia Martinez & Zach Coelius | E1427
Antonio Garcia Martinez, author of "Chaos Monkeys," and investor Zach Coelius dive into compelling discussions. They share insights from Antonio’s recent trip to Ukraine and unpack the significant fallout of Apple’s ad tracking updates on Facebook. The duo also reflects on Elon Musk’s role with Twitter and the implications for its future. Additionally, they tackle the complex landscape of crypto regulation and how emerging technologies intersect with these evolving challenges.

Apr 5, 2022 • 1h 2min
Elon buys ~9% stake in Twitter + Freestyle Capital's Dave Samuel | E1426
Dave Samuel, co-founder of Freestyle VC, shares insights on early-stage investing and the dynamics of venture capital. He discusses the intriguing implications of Elon Musk's 9.2% stake in Twitter, analyzing its potential influence on governance and public discourse. Samuel emphasizes the importance of fund size in dictating investment strategies and gives valuable advice on providing feedback to founders, especially the delicate art of saying no. Tune in for a peek into the evolving landscape of investments and the complexities of capital allocation.

Apr 3, 2022 • 1h 7min
Inbound vs. outbound deal flow (VC School) + Jason Jacobs of My Climate Journey | E1425
Jason Jacobs, founder of Runkeeper and My Climate Journey, dives into the world of venture capital's deal flow strategies, discussing the nuances of inbound vs. outbound approaches. He emphasizes the importance of community in climate tech, sharing insights from his journey in advocacy and scaling investments. Jacobs advocates for transparent communication with founders, presenting a unique philosophy that turns relationships into opportunities. The conversation highlights the transformative power of climate innovation and the vital role of community in tackling global challenges.

Apr 1, 2022 • 1h 51min
GoPuff & Fast trimming staff + Bradley Tusk on tech regulation + Glimpse Co-founder Akash Raju | E1424
Bradley Tusk, a political strategist and venture capitalist known for his work with Uber, shares insights on tech regulation affecting startups. He discusses Uber’s creative strategies in NYC and the nuances of sports betting laws. Akash Raju, co-founder of Glimpse, brings unique ideas on branded product placement in short-term rentals, highlighting how QR codes enhance guest experiences. The conversation dives into recent layoffs at GoPuff and Fast, analyzing the implications of shifting business models in the tech landscape.

Mar 31, 2022 • 1h 14min
NFT exclusive restaurant: FlyFish Club CEO David Rodolitz + Reviewing We Crashed & The Dropout with Lon Harris | E1423
David Rodolitz, the CEO of FlyFish Club, shares insights on NYC's first NFT-based restaurant, discussing how blockchain technology redefines dining experiences and fosters community. Lon Harris, a streaming expert, critiques the narratives in popular shows like WeCrashed and The Dropout, analyzing character motivations and the portrayal of hustle culture. Together, they explore the evolving landscape of media and its impact on startup culture, blending humor with critical observations about ethical dilemmas in business.