

This Week in Startups
Jason Calacanis
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.
Episodes
Mentioned books

May 7, 2021 • 1h 7min
Facebook’s Oversight Board rules on Trump ban plus how to reverse engineer TAM & more | E1211
The discussion dives into the Facebook Oversight Board's controversial decision on Trump’s ban, exploring its implications for content moderation. A fascinating proposal emerges to tackle bad actors on social media. Insights into assessing Total Addressable Market reveal effective strategies for startups. The podcast also contrasts the bravery of police during the Capitol riots with the chaos of that day, highlighting journalism's integrity in tech and the need for balanced reporting amidst sensationalism.

May 6, 2021 • 1h 11min
Fundraising | Scaling Your Startup S2 E4 with Density’s Andrew Farah and SoleSavy’s Dejan Pralica | E1210
Andrew Farah, Co-founder and CEO of Density, shares his successful strategy for raising over $100 million in funding, emphasizing the importance of product demos and effective narratives. Meanwhile, Dejan Pralica, CEO of SoleSavy, reveals how he masterfully combines community and commerce, offering insights into building genuine relationships with investors. Both entrepreneurs candidly discuss the mistakes they made, providing valuable lessons on crafting pitch decks and navigating the emotional landscape of fundraising.

May 5, 2021 • 57min
Crafter’s Morgan Spenla on delighting makers with memberships, materials, and a marketplace | E1209
Morgan Spenla, CEO of Crafter, shares insights on how her company revolutionizes crafting through immersive experiences and community connections. She discusses the rise of crafting during the pandemic, emphasizing its therapeutic benefits. Spenla explains their unique subscription model that enhances user experience, leveraging community feedback and curated materials. Additionally, she reveals her hiring strategy, choosing customer support talent from Starbucks, and highlights the importance of mentorship and dynamic team relationships in driving growth.

May 5, 2021 • 48min
Breaking down Basecamp’s tumultuous week, politics at work & more | E1208
This week dives into Basecamp's controversial ban on political discussions, leading to significant employee resignations. The conversation highlights the clash between workplace culture and political expression. A discussion on prioritizing work over politics emphasizes the importance of core mission focus. Insights on fostering meaningful connections reveal strategies for building relationships at work. Additionally, listeners get advice on surrounding themselves with great people and navigating complex corporate dynamics.

Apr 30, 2021 • 53min
How Tiger Global is outpacing VC with better, faster, cheaper, capital ft. Founders Fund’s Everett Randle | E1207
Everett Randle, Principal at Founders Fund and former team member at Bond Capital and Kleiner Perkins, delves into Tiger Global's rapid, disruptive strategies in the investment landscape. He discusses how they are reshaping venture capital by taking significant stakes in startups and the implications for founders. Randle introduces his "Walmart of VC firms" model, emphasizing the importance of founder trust amid aggressive capital deployment. The conversation also touches on evolving funding dynamics and the challenges faced by traditional investors.

Apr 29, 2021 • 54min
Sales | Scaling Your Startup S2 E3 with GRIN’s Brandon Brown and LeadIQ’s Mei Siauw | E1206
Brandon Brown and Mei Siauw, CEOs of Grin and LeadIQ respectively, share their insights on scaling sales in the B2B SaaS world. They discuss creating effective sales motions and structuring sales pods for maximum efficiency. Brandon emphasizes the importance of hiring a great VP of sales and training SDRs into AEs. Mei dives into building a robust outbound sales team, highlighting the need for personalization in outreach. Together, they tackle challenges in hiring top talent and improving team dynamics, especially in a remote work environment.

Apr 27, 2021 • 1h
Arlan Hamilton on raising $5M in crowdfunding, empowering & educating underestimated founders | E1205
Arlan Hamilton, founder of Backstage Capital, shares her inspiring journey of raising $5M in crowdfunding to support underestimated founders, particularly women and people of color. She discusses the groundbreaking success of her campaign on Republic and how it reflects a growing interest in inclusive investment. Arlan also highlights her Founder University program, aimed at mentoring diverse entrepreneurs and preparing them for the challenges of venture capital, while tackling issues of systemic injustice in the startup ecosystem.

Apr 27, 2021 • 18min
Emergency Pod! Tim Cook vs. Mark Zuckerberg: Apple and Facebook go to war over privacy updates | E1204
Dive into the intense rivalry between Tim Cook and Mark Zuckerberg as Apple and Facebook clash over privacy updates. Discover how Apple's iOS 14.5 impacts Facebook's advertising. The philosophical divide of user privacy versus data collection unfolds. Explore potential solutions for businesses navigating these changes. Plus, the push for a subscription model that prioritizes user privacy and trust in a tech landscape fraught with tension. It's a fascinating examination of the future of digital advertising and personal data.

Apr 23, 2021 • 59min
Altimeter’s Brad Gerstner on taking Grab public in largest SPAC ever, fixing broken IPOs | E1203
Brad Gerstner, founder of Altimeter Capital and a leading figure in SPAC investments, delves into the groundbreaking public offering of Grab, the largest SPAC ever. He critiques the traditional IPO process for its flaws and proposes solutions for improvement. Gerstner emphasizes the importance of responsible retail investing and advocates for a bold idea: investing $2000 for every American at birth to harness capitalism's potential for societal betterment. He also discusses the future of retail investing and the challenges that accompany market accessibility.

Apr 21, 2021 • 1h 13min
Social Marketing | Scaling Your Startup S2 E2 with Mehak Vohra and Kate Bradley-Chernis | E1202
Join Mehak Vohra, Founder and CEO of SkillBank, a career accelerator for marketing, and Kate Bradley-Chernis, CEO of Lately, a cutting-edge social media management platform. They dive into how Mehak leveraged TikTok to boost signups with engaging content strategies. Kate shares her secrets on effective business writing and enhancing B2B engagement on LinkedIn, emphasizing authenticity and clarity. The conversation also touches on the power of AI in crafting content and the significance of storytelling to truly connect with audiences.


