Yinglan Tan considered the future of his young Singapore-based venture capital firm. On the one hand, the intuition that was behind the initial creation of Insignia in 2017 had been proven correct. The venture capital market in Southeast Asia had grown rapidly, driven by the spread of e-commerce around the globe and the increased willingness of venture investors around the world to look globally. The new venture group, exploiting existing connections and a nimble structure, had rapidly establish itself in this promising market. This success was incredibly gratifying to Tan. On the other hand, some important questions remained. Foremost among these was the question of scaling. One concern related to whether Insignia should "climb the ladder," and follow its portfolio companies as they received substantially larger financing rounds. These financings would entail raising much more capital but doubling down on winners might yield attractive returns. Second, if it was to garner large amounts of additional capital, the Insignia model would need to evolve, and in important ways come under stress. Finally, the venture market was showing signs of stress. If the long-anticipated downturn was here, what would be the implications for Insignia?