Episode Summary
Executive Summary: Jason Calacanis covers a wide range of topics in this Ask Jason episode, including his stance on Black Lives Matter and the need for economic reparations via business loans and education. He discusses the reshoring of manufacturing to the US post-COVID, recommends pre-selling SaaS products, advises on becoming a great syndicate member, and predicts a hybrid remote-work future. He also urges the creation of an Instagram competitor that shares revenue with creators, explores founder-VC disputes, and reflects on his own succession plans and long-term goals.
Main Topics: Black Lives Matter & Reparations (Priority: 5/5): Jason shares his personal and professional perspective, advocating for actions like building a creator-owned Instagram, reforming representation in VC, and implementing reparations through education and small business loans. Post-COVID Remote Work & City Dynamics (Priority: 4/5): Jason analyzes how COVID-19 may permanently shift work to hybrid models, potentially lowering rents in SF and enabling companies to hire globally at lower costs, while still believing cities will remain central. Instagram Competitor with Revenue Sharing (Priority: 4/5): Jason strongly argues for building a competitor to Instagram that shares advertising revenue with creators, similar to YouTube's model, calling it a huge unmet opportunity. Pre-Selling SaaS Products (Priority: 3/5): Jason provides a detailed strategy for pre-selling software, emphasizing offering exclusive early access and significant discounts to early customers in exchange for upfront commitments. Becoming a Great Syndicate Member (Priority: 3/5): Jason advises syndicate members to be supportive, non-annoying, and psychologically prepared for high failure rates, focusing on long-term wins and being a resource to founders. Founder-VC Disputes & Diligence (Priority: 3/5): Jason discusses the balance of power between founders and VCs, noting that disputes are often two-way and that founders should diligently check references on investors. Succession & Personal Goals (Priority: 2/5): Jason shares his interest in finding a co-host with a complementary audience, and his long-term ambition to become the greatest angel investor by volume and returns.
Key Arguments: Black culture drives platform value but lacks ownership; a creator-revenue-sharing Instagram competitor is needed. Reshoring manufacturing to the US is a strategic opportunity for startups, but depends on sustained political and economic will. Pre-selling SaaS works by framing early access as a competitive advantage and offering steep discounts for multi-year commitments. Syndicate members should manage their psychology, accept high failure rates, and provide support without being annoying. Founder-VC disputes are normal; founders should always check references on investors, just as VCs diligence them. A hybrid remote/in-office future will lower costs and increase hiring flexibility for startups. Reparations via forgivable business loans and free college education for Black Americans are practical economic solutions to systemic inequity.
Data Points: Founder University programs: 14 total, one-third for women, one-third for underrepresented founders - Jason's efforts to increase diversity in his accelerator pipeline Syndicate average check size: $6,000 per investor - Example of how small checks aggregate to $600,000 with 100 members Startup failure rate: 80% - Used to explain the need for founder support and psychological resilience San Francisco rent decline: 10-20% during COVID - Observed trend as people left the city, potentially making it more affordable Instagram estimated valuation: $250-500 billion - Underlines the massive market opportunity for a competitor Typical minimum angel check: $25,000 - Contrasted with the $5,000 Jason recommends for beginners
Pivotal Quotes: "Actions speak louder than words. I don't want to be one of these people on Twitter who just virtue signals. I actually just want to see the change happen." — Jason Calacanis: On his approach to racial equity and his reluctance to pontificate without taking concrete steps "I believe we need to change the ratio in terms of who owns these platforms and representation there." — Jason Calacanis: Advocating for Black founders and influencers to build and own an Instagram alternative "Founders need support. They need encouragement. They need a warm ear. Don't be annoying." — Jason Calacanis: Core advice for syndicate members on how to behave toward portfolio founders
Implications: Listeners should consider acting on Jason's call to build a creator-centric Instagram rival and explore reshoring opportunities. Founders should adopt pre-selling techniques and diligently vet investors. The trend toward hybrid remote work will continue, affecting hiring and real estate decisions.
About 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.