E14: Jason Calacanis on How He Returned 4,000X ($25K into $100MM) on a Single Investment

Jason Calacanis, founder of LAUNCH and host of the All-In Podcast and This Week in startups, sits down with David Weisburd to discuss his new fundraise and his views on the venture capital landscape.

We’re proudly sponsored by Tactyc, visit tactyc.io if you’re ready to level up your venture fund.

(0:00) Introduction to Jason Calacanis and venture capital insights (1:12) Jason Calacanis's investment strategy and angel investing journey (3:32) Being a Sequoia scout and investing in networks (6:01) Discussing the power law and first carry check in VC (8:15) The role of randomness and relationships in investment success (10:28) Sticking with founders and notable investments (14:23) Sponsor: Tactyc.io (15:17) Secondary market strategies and the joy of early-stage investments (16:14) Investment funnel and selection process (17:21) GP commit, confidence in investments, and AngelList's impact (20:39) The case for writing small checks in syndicates (21:51) Understanding venture capital returns and portfolio strategy (24:00) Social proof and its impact on venture capital (25:02) Deal flow: significance, sorting, and qualifying (28:55) Portfolio construction, follow-on investments, and due diligence (32:55) Using software to manage investments and team training methods (35:44) Work-life balance and VC's competitive aspects (37:06) Comparing early-stage to late-stage investments and long-term returns (39:26) Closing thoughts and gratitude