
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

7 snips
Aug 5, 2024 • 1h 20min
TWiST 500! Huntress, TollBit & Cyera | E1989
Kyle Hanslovan, CEO of Huntress, shares insights on achieving $100 million in annual recurring revenue and the challenges of cybersecurity for small businesses. Toshit Panigrahi, Co-founder of Tollbit, discusses fair compensation for publishers in the evolving AI landscape. Tamar Bar-Ilan of Cyera emphasizes the importance of data security posture management and the complexities of leveraging data securely. Together, they reveal innovative strategies for startups thriving in a competitive and rapidly changing tech-driven environment.

4 snips
Aug 2, 2024 • 1h 5min
Overcoming SMB Roadblocks: Expert tips from Gusto's Josh Reeves | Episode 1988
Josh Reeves, Co-founder and CEO of Gusto, shares insights from his entrepreneurial journey, emphasizing the importance of building products that resonate with users, particularly in the SMB sector. He discusses overcoming challenges like compliance and cybersecurity in small businesses, as well as effective growth strategies and metrics. Reeves also highlights unique marketing tactics, such as word-of-mouth referrals, and the significance of fostering deep customer connections to drive retention and satisfaction in today’s competitive landscape.

26 snips
Jul 31, 2024 • 1h 8min
The $97 Billion VC Panel | E1987
Dana Johns, Head of Private Equity in New Jersey, and Tom Loverro, Partner at IVP, delve into the thrilling world of venture capital. They discuss the resurgence of secondary pricing, hinting at an optimistic market revival. The duo also explores the impact of cybersecurity investments and how evolving dynamics affect startup independence. With insights on investor strategies and the balance of product development versus sales, they shed light on navigating the complexities of capital allocation while keeping an eye on emerging sectors.

6 snips
Jul 30, 2024 • 54min
The Power of WEKA with Antonio Gracias and Liran Zvibel + Jam with JCal: Uptrends AI | E1986
Antonio Gracias, a prominent investor from Valor Capital with a track record in SpaceX and Tesla, joins Liran Zvibel, CEO of Weka, which specializes in data management for AI. They dive into Weka’s impressive product market fit and discuss transformative energy solutions for future data centers. The conversation highlights innovative applications in high-performance computing that enhance GPU utilization, and explores the unique strategies investors use to secure stakes in such promising technology. The chat is packed with insights into the future of both tech and investment.

25 snips
Jul 26, 2024 • 1h 4min
Scaling Creativity: Josh Silverman on Etsy's growth, AI integration, and market strategies | E1985
Josh Silverman, CEO of Etsy and former venture capitalist, discusses the marketplace's impressive growth during the pandemic, skyrocketing sales from $2 billion to $12 billion. He dives into the unique challenges of maintaining authentic handmade products amid evolving definitions of creativity, especially with AI's rise. Silverman also highlights Etsy’s community support for Ukrainian sellers and shares insights on balancing quality control while fostering creativity and innovation in a competitive market.

Jul 24, 2024 • 1h 13min
Wiz passes on Google, Meta pushes open-source AI ahead, Spotify’s earnings, and more! | E1984
The podcast dives into the fallout from the Wiz-Google deal, showcasing how startups navigate corporate pressures. Spotify's impressive earnings are highlighted, alongside discussions on its strategic pivot towards podcasting. The conversation shifts to Universal Basic Income, exploring its implications for economic mobility and personal agency. Meta's push for open-source AI is also tackled, revealing contradictions in big tech's support for open-source initiatives.

5 snips
Jul 22, 2024 • 1h 21min
Building Enduring Value and Hitting Incremental Gains with Benchmark’s Sarah Tavel | E1983
Sarah Tavel, a Partner at Benchmark and former leader at Bessemer Venture Partners and Pinterest, shares her insights on the dynamic venture capital landscape. She discusses how startups can navigate increasing competition, the importance of governance and trust, and the balance between hype and value creation. Tavel emphasizes the significance of incremental gains in leadership and the challenges of hiring in today's market. Her experiences shed light on what truly drives successful partnerships between investors and founders.

22 snips
Jul 19, 2024 • 1h 7min
US space innovation, defense tech challenges, and more with True Anomaly’s Even Rogers | E1982
Evan Rogers, CEO and co-founder of True Anomaly, dives into the challenges and advancements in U.S. space innovation and defense tech. He discusses the critical need for the U.S. to secure its interests against adversaries like Russia and China. The conversation also highlights True Anomaly's latest innovations, including the Jackal reconnaissance platform. Rogers emphasizes the importance of effective government contracting strategies and how private capital plays a pivotal role in enhancing national security through innovative startups.

Jul 17, 2024 • 1h 1min
Top 5 VC funds raise big $, venture capital DPI is back, and Sequoia’s offer to LP’s | E1981
Jamie Rhode, a partner at Screen Door, champions diversity in venture capital while Matthew Mulvey from Liquid 2 highlights early-stage investments. They discuss the resurgence of distributed paid-in capital (DPI) in Silicon Valley, focusing on Sequoia's innovative strategies and liquidity options for limited partners. The conversation emphasizes the importance of empowering underdog founders from diverse backgrounds and the evolving trends in capital investment. Their insights reveal shifting dynamics in venture capital and the critical need for inclusive funding practices.

Jul 15, 2024 • 1h 8min
Google weighs $23B for Wiz, startups in a second Trump admin, and Sequoia's Stripe sale | E1980
The podcast dives into the impact of social media in amplifying conspiracy theories, particularly following an assassination attempt on a former president. It scrutinizes Silicon Valley's political apprehensions regarding Biden and Trump's policies on startups. The discussion shifts to Sequoia's approach to their Stripe investment amidst complicated market conditions, and it unpacks Google's potential $23 billion acquisition of cybersecurity company Wiz, highlighting the rising importance of the sector in tech competition.