This Week in Startups

Jason Calacanis
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12 snips
Aug 26, 2025 • 1h 14min

xAI’s App Store lawsuit, Intel shares vs. grocery stores, and Netskope’s IPO | E2169

Exploring the fine line between skepticism and optimism, the hosts dive into the implications of government investments in companies like Intel. They spar over the upcoming lawsuit against Apple by xAI, debating its potential impact on the app market. Netskope's IPO journey highlights the growing importance of cybersecurity in a remote work world, while the conversation touches on innovative revenue-sharing models for publishers amidst advancements in AI. Ultimately, it's a lively discussion on innovation's future and the challenges it faces.
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102 snips
Aug 22, 2025 • 1h 17min

Do Kwon Guilty, Powell Pivot & OpenAI’s $12B Run Rate | E2168

The fallout from Do Kwon's guilty plea over the Terra/Luna collapse raises questions about crypto's future. Fed Chair Powell hints at a potential rate cut, sparking a lively discussion on market impacts. OpenAI makes headlines with its staggering $1 billion monthly revenue and a $12 billion run rate. Canva makes a notable comeback with a $42 billion valuation. Meanwhile, tensions rise in the autonomous vehicle sector due to protests against robotaxi initiatives. Tune in for insights into the evolving landscapes of AI, crypto, and startups!
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88 snips
Aug 20, 2025 • 59min

Is Chalk.ai the ‘Next Databricks’? + Tollbit’s Bot Paywall for AI Agents | E2167

Marc Freed-Finnegan, Co-founder and CEO of Chalk, discusses tackling data freshness in AI by providing real-time data pipelines that boost inference speed, positioning Chalk as a potential leader in the field. Toshit Panigrahi, CEO of Tollbit, shares insights on their innovative 'bot paywall' designed to change how AI agents access content, signaling a shift in data licensing trends. Listen in as they dive into the wrap-up on the evolving landscape of AI monetization and data accessibility, hinting at what the future holds for this dynamic industry.
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29 snips
Aug 19, 2025 • 31min

Scaling AI Photo Editing to 300M Users with Photoroom’s Matt Rouif | AI Basics with Google Cloud

Matt Rouif, Co-founder & CEO of Photoroom, shares insights from leading an AI photo editing app with over 300 million downloads. He discusses building specialized AI models and their journey from a small startup to generating over $50 million in revenue. The conversation touches on the importance of user feedback in scaling AI technology, ethical considerations in AI advertising, and innovative strategies for personalized ads. Rouif also emphasizes brand safety and the future of digital imagery, offering invaluable lessons for founders and operators.
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82 snips
Aug 18, 2025 • 38min

Decart makes AI faster, Lume teaches lamps to fold laundry | E2166

Dean Leitersdorf, CEO and Founder of Decart, discusses optimizing GPU performance to significantly boost AI capabilities. He reveals how efficient AI speed creates new opportunities and envisions chatbots as the future interface. Later, Aaron Tan, founder of Syncere AI, shares insights on Lume, a viral robotic lamp that folds laundry, and explains why he believes robotics need not be humanoid. Together, they explore transformative AI and robotics, highlighting innovative designs that enhance everyday living.
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115 snips
Aug 15, 2025 • 57min

Meta’s “Sensual” AI Doc LEAKS, Opendoor’s dreams became memes +  OpenAI plans $1T data center spend | E2165

In this lively discussion, internal controversies at Meta about AI interactions with children spark outrage, especially regarding romantic conversations. The pressure of AI job displacement looms large, especially in New York, raising concerns about the future job market. OpenDoor's unexpected rise as a meme stock is dissected, showcasing the volatility of tech investments. The hosts express skepticism over the promised $1 trillion OpenAI data center investment, questioning its reality amidst the current economic landscape.
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148 snips
Aug 14, 2025 • 1h 21min

The End of the ZIRP Era, and why recruiting is SO PAINFUL | E2164

Dave McClure, known for founding 500 Startups, joins venture capitalists Tomasz Tunguz and Grady Buchanan for a lively discussion on the evolving venture landscape. They delve into the challenges of recruiting amid shifting market dynamics, highlighting the impact of long private funding durations on startups. The trio also debates the implications of recent regulatory changes on mergers and acquisitions, and how AI is reshaping investment strategies. Don't miss their insights on adapting to the new era of startup efficiency!
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114 snips
Aug 12, 2025 • 1h 16min

GPT Psychosis is spreading, the NYT is Super-Doxxing Zuck, and Trump is wetting his beak on Chinese chip exports | E2163

Is GPT Psychosis a real concern? The hosts delve into the alarming emotional connections users are forming with AI. Meanwhile, a controversial New York Times piece on Mark Zuckerberg’s lavish living sparks a heated discussion about privacy versus public interest. They also tackle Trump’s export fees on chip manufacturers, questioning whether it's a justified measure or a shakedown. Plus, there’s debate over the ethics of juggling multiple jobs in today's workforce.
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199 snips
Aug 8, 2025 • 1h 19min

GPT-5 comes alive, Apple is struggling, and Ripple bought Rail | E2162

In a critical discussion, the hosts suggest Apple may need a leadership change to revive its innovative edge. The launch of GPT-5 prompts questions about whether we’re entering an AI trough of despair. Ripple’s bold acquisition of Rail raises intriguing regulatory discussions. They also explore Bumble's new direction and Airbnb's potential paths amid changing travel dynamics. The episode wraps up with a look at the intersection of technology, marketing, and ethics in AI, particularly regarding its role in therapy.
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43 snips
Aug 7, 2025 • 1h 13min

Communist coffee hits NYC, RIP Hulu, GPT-5 arrives and more | E2161

A new coffee brand inspired by communism hits NYC, stirring discussions about branding and market strategies. Disney reveals plans to sunset Hulu, raising eyebrows on streaming dynamics. A deepfake AI ad sparks conversations on copyright and creativity, leaving listeners intrigued. The arrival of OpenAI's open-weight models offers fresh insights into user privacy and tech ethics. With foreign brands like Luckin Coffee making waves, the competitive landscape of consumer sectors continues to evolve.

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