Scaling Childcare with Tech: Winnie.com’s Blueprint for Growing with Purpose & Profit | E2005

Sara Mauskopf, CEO of Winnie, joins Alex Wilhelm to discuss Winnie's evolution and its focus on childcare services. They explore the company's growth, transparency, and market positioning (9:45), the challenges of balancing investor expectations with business models (22:30), and the impact of remote work on childcare demands (35:15). The conversation also covers profitability, operational efficiency, and marketing strategies (46:20), as well as the broader implications of tech M&A, FTC regulations, and innovation policies (58:10).

The Rise of Stablecoins with Circle’s Jeremy Allaire | E2004

Circle’s Jeremy Allaire joins Alex Wilhelm to discuss the growth of stablecoins, stablecoin market infrastructure, their impact on global financial systems, and more!

Fundraising hurdles and M&A slowdown with Becki DeGraw | Wilson Sonsini Startup Legal Basics

Wilson Sonsini Partner Becki DeGraw joins Jason on the latest edition of Startup Legal Basics! In this episode, they break down fundraising trends, the challenges of M&A, and the evolving regulations for tech companies.

Medium: Reaching Profitability while The Internet is Broken + CorePod | E2003

Tony Stubblebine of Medium joins Alex to discuss the broken internet and ad-based models, the impact of AI on content creation, and Medium's unique curation and financial model (9:30). They delve into Medium's growth, geographic expansion, and AI translation (20:45), as well as the challenges and benefits of AI-driven media platforms (32:10). The conversation highlights Medium's subscriber growth, financial milestones, and venture scale potential (45:00). Tony shares his personal use of AI and thoughts on AI's future in business (58:15). Later, Ulan Abdurazakov introduces CorePod, discussing its product strategy and market validation (1:10:30).

Superhuman 2.0: The AI edge, top productivity hacks, and the future of email | E2002

Superhuman’s Rahul Vohra joins Jason to discuss the evolution of Superhuman. They delve into Superhuman's onboarding strategy (11:17), live demos of Superhuman's AI features (27:37), explore AI's impact on team management, and more!

AI Demos: Gemini Gmail, Search GPT, Groq with Voice & Playground | E2001

Sundeep Madra joins Jason Calacanis to explore AI demos and discuss the impact of Q4 on startups and Nvidia's market performance (5:30). They dive into chip design advancements, experiences with ChatGPT-4, and Google's Gemini in Gmail (15:20). The conversation covers generative AI and the importance of SOC 2 compliance (27:10), AI integration in Gmail, and personalization tools (35:45). They also examine Search GPT functionalities, ethical considerations in AI, and practical applications like Claude AI's app development (50:00). The episode concludes with a comparison of Playground and Canva, and the future of user interfaces (1:05:30).

Episode 2000! Epic guests, huge news, and how to build a media legacy in 14 short years | E2000

Jason and Alex kick off episode 2000! They reflect on TWiST’s origins and early episodes, highlighting notable guests and memorable moments. They also share fan messages, and insights from cohosts, and wrap up celebrating standout moments.

Startup Pitch Competition: Three founders compete for $25K | E1999

Jason and Kelly kick off the Founder University startup pitch competition, then we hear from Eric Gilbert-Williams on The Public Bored, Matt Schwed on Speed AI, and Joe Tannorella on PodEngine. Finally, Jason awards a $25K investment, and details how to apply!

The charges against Pavel Durov, the future of encryption, and secondaries are heating up | E1998

Alex Wilhelm joins Jason to discuss the arrest of Pavel Durov, national security concerns, and encryption debates. They also dive into G Squared raising $1B for it’s latest fund, IBM's activities in China, iPhone production shifts, more!

AI Demos: New Runway, Flux, Grok 2.0 & Jam Session with Ulama | E1997

Sundeep Madra joins Jason Calacanis to discuss AI market trends, the future of AI applications, and the role of AI in career trajectories. The episode features live demos of AI tools like Claude and Flux, examines AI's impact on elections, and explores the potential for AI misuse. The discussion also delves into AI-generated content concerns, the integration of AI in operating systems, and funding opportunities for startups. Then we meet Jam with JCal contest winner Tyce Herrman of Ulama to hear about what his company is building. The episode wraps up with insights into AI in code compliance, challenges in launching standalone products, and strategies for architectural firm integration.

Legal must-haves before raising capital with Becki DeGraw | Wilson Sonsini Startup Legal Basics

Wilson Sonsini Partner Becki DeGraw joins Jason on the latest edition of Startup Legal Basics! In this episode, they break down common legal oversights, risks of DIY legal documents, pro forma cap tables & ESOPS, and much more!

Venture returns, recovering startups, and VC conflicts | E1995

Alex Wilhelm joins Jason to discuss venture capital fund performance, potential big tech breakups, SF Standard piece analysis on Ben and Felicia Horowitz, startup shutdowns, and more!

Liquidity: Recession fears, AI market shifts, and the future of tech hubs | E1994

David Weisburd hosts Elad Gil, David York, and Jason Calacanis to discuss recession fears, new investment trends, geographic and talent concentration in the startup sector, and more!

Final Boss Sour’s James Hicks + River’s Rae Lambert | E1993

Jason Calacanis kicks off the episode with an introduction to Final Boss Sour and an overview of what's to come. He shares his investment approach before introducing the guest. The discussion delves into the unique aspects and appeal of Final Boss Sour's products, emphasizing better-for-you products and social media strategies. The potential of TikTok for social shopping and influencer monetization is explored, followed by insights into the future of commerce and retailer adaptations. The episode also covers video game tie-ins, experiential retail, and pop-up concepts. Ray Lambert joins to discuss community building with River, touching on software platforms, community management, business models, and monetization strategies.

WeRide IPO, Polymarket + Perplexity, the Trump Bump and more! | E1992

Jason Calacanis and Alex Wilhelm kick off the show discussing the evolution of startup costs and media aggregation. They delve into the Trump and Elon conversation and media's addiction to Trump coverage. The episode also explores Trump's media strategies and societal resistance to tech, including the rise of self-driving cars and their impact on Uber and Lyft. Other topics include the FIRE movement, Perplexity's AI competition, Reddit's traffic and monetization, and the rise of European venture capital and unicorns. The episode concludes with a comparison of work culture between Europe and the US and investing in AI startups.

Startup Pitch Competition: Four founders compete for $25K | E1991

Jason and Kelly kick off the Founder University startup pitch competition. We hear from Pablo on Big Rentals, Brittany on Where2Wheel, Ardalan on MyLens, and Mariano on Prosperous AI. Finally, Jason awards a $25K investment, and details how to apply!

Liquidity Summit Talks: Antonio Gracias and Gavin Baker | E1990

Alex leads us into two great talks from Liquidity Summit 2024. First Jason sits down for a one-on-one with Valor’s Antonio Gracias, followed by a great talk with Gavin Baker of Atreides.

Navigating startup funding market trends with Becki DeGraw | Wilson Sonsini Startup Legal Basics

Wilson Sonsini Partner Becki DeGraw joins Jason on the latest edition of Startup Legal Basics! In this episode, they break down the current state of startup funding, anti-dilution provisions, re-incentivizing management teams, and much more!

Navigating startup funding market trends with Becki DeGraw | Wilson Sonsini Startup Legal Basics

Wilson Sonsini Partner Becki DeGraw joins Jason on the latest edition of Startup Legal Basics! In this episode, they break down the current state of startup funding, anti-dilution provisions, re-incentivizing management teams, and much more!

TWiST 500! Huntress, TollBit & Cyera | E1989

We are kicking off our coverage of the TWiST500 with three fantastic founders: Kyle Hanslovan of Huntress, Olivia Joslin and Toshit Panigrahi of TollBit, and Tamar Bar-Ilan of Cyera.