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(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