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) Episode Preview (1:15) Fundraising for LAUNCH and LP investing experience (2:10) Sequoia’s investments in Twitter and Zynga (3:12) Being Sequoia’s first venture scout and earning 50% carry (4:28) Venture wealth bombs (8:06) Jason’s 4,000x investment in Uber (9:44) Loyalty in venture (10:07) Investing in Superhuman (13:15) How Jason got a 200x on an AngelList syndicate deal (14:20) Episode Sponsor (14:59) Unlocking value through secondaries (15:41) Qualities of top managers (16:23) Jason’s current fund (17:21) Aligning incentives through a GP commitment (20:54) Sourcing deals through Syndicate investments (23:56) The importance of social proof (25:04) Why deal flow is destiny (28:23) The importance of ownership (29:51) Sharp elbows in Series A and beyond (31:28) Jason’s current portfolio construction (32:29) YC's impact on venture (34:05) Playing for carry, the importance of a techstack and the myth of work life balance (36:19) Venture is a competition (37:06) Why early stage venture is not zero-sum