Episode Summary
Executive Summary: This Ask Jason episode covers Black Lives Matter and concrete actions for racial equity, startup opportunities in reshoring manufacturing, how to pre-sell SaaS, how to be a good syndicate investor, the future of Silicon Valley in a remote/hybrid world, and a call for an Instagram competitor that shares revenue with creators. Jason emphasizes action over signaling, founder diligence, and using startups to fix structural problems.
Main Topics: Black Lives Matter, equity, and action over signaling: Jason discusses racial injustice, representation in startups/investing, reparations, and practical economic remedies like education and small business loans rather than just public statements. Reshoring manufacturing and supply-chain resilience: He argues COVID exposed dependency on China for PPE, drugs, and critical goods, creating opportunities for startups that help rebuild U.S. manufacturing and supply chains. Pre-selling SaaS before the product exists: Jason explains how founders can secure early customers by pitching exclusivity, competitive advantage, and discounted multi-year commitments before building software. How to be a good syndicate investor: He advises small-check syndicate members to be supportive, non-annoying, patient, and emotionally disciplined because most angel bets fail and founders need encouragement. Silicon Valley, remote work, and the future of startup geography: Jason revisits the case for being in Silicon Valley, then concludes hybrid/remote is likely the future, with lower costs, broader hiring, and cities still remaining important. Building an Instagram competitor that shares revenue with creators: He calls for a new Instagram-like platform with creator revenue sharing, similar to YouTube’s model, and suggests this could drive meaningful market share. Founder-VC disputes and diligence: Jason says conflicts are common and not always one-sided; founders should diligence investors just as investors diligence founders, especially around conflicts and fit.
Key Arguments: Public statements matter less than sustained action; Jason says he prefers making changes through Founder University, investing, and business building rather than Twitter performativity. Racial inequity should be addressed through economic tools: education, small-business loans, and potentially reparations, because opportunity and ownership are still unequal. Black culture has created much of modern internet culture, so Black founders and creators should own more of the platforms that monetize that culture. COVID exposed strategic supply-chain weaknesses, making domestic manufacturing a real startup opportunity, especially in PPE, pharmaceuticals, and other critical goods. Founders can and should pre-sell software by offering exclusivity and competitive advantage to early customers, often collecting meaningful capital before writing code. Small syndicate checks reduce risk, but members must act like supportive partners, not noisy speculators, because founders are under extreme pressure and failure is common. Remote work will likely become hybrid rather than purely office-based; companies will optimize for output, broaden talent access, and lower costs. Investors and founders both need to diligence each other; conflicts, competing investments, and bad behavior can exist on both sides.
Data Points: Founder University programs: 14 total - Jason says he has run many Founder University cohorts. Founder University diversity mix: About one-third women and one-third underrepresented founders - He describes the composition of cohorts focused on increasing access. Syndicate membership: 4,000 members - Jason says his syndicate is the largest in the world. Syndicate investors who have invested: 2,000 - He notes half the membership has made an investment. Average syndicate check size: $6,000 - Jason cites the typical contribution size in his syndicate. Calm syndicate raise: $328,000 - He references the first syndicate deal for calm.com. Average check on Calm deal: $4,000 - Jason recalls the average individual investment in that deal. Typical angel minimum: $25,000 to $50,000 - He contrasts syndicate investing with standard angel minimums. Proposed pre-sale discount example: $75,000/year list price; $25,000 for a 2-year prepay - Jason uses this as an illustrative pricing strategy for a SaaS pre-sale. Potential creator revenue share: 55% to 80% - He suggests an Instagram competitor could share ad revenue similarly to YouTube or the App Store. Instagram valuation reference: $250 billion to $500 billion - Jason estimates Instagram’s strategic value within Facebook. COVID manufacturing ramp-up window: 3 to 6 months - He says production of masks/ventilators was ramped up over this period. Remote-work transition expectation: Third quarter of 2021 - Jason speculates that COVID would be mostly resolved by then. Potential lower hiring cost in remote world: $30,000 to $50,000 less - He estimates companies may hire talent cheaper outside San Francisco. Silicon Valley rent change: 10% to 20% down - He says rents in San Francisco were reportedly falling during the crisis. Portfolio success estimate: 20% chance of founder/company success - Jason uses this to emphasize why syndicate investors should be patient and supportive. Potential syndicate scale example: 100 people x $6,000 = $600,000 - He explains how pooled small checks can create a meaningful check size.
Pivotal Quotes: "actions speak louder than words" — Jason: He uses this while discussing Black Lives Matter and his preference for concrete steps over performative posting. "If the top 50 or 50 of the top 200 African-American influencers on Instagram left and started their own, boy, would that be a sea change." — Jason: He argues that creators, especially Black creators, should have ownership in the platforms they culturally power. "What I would do is I would just talk to other founders the investor has invested in" — Jason: He recommends founder diligence on investors and how to assess fit before taking capital.
Implications: Listeners are pushed toward practical execution: build inclusive companies, rethink supply chains, pre-sell intelligently, and diligence investors. The episode frames startups as a lever for social change and post-COVID market shifts.
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.