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Published Dec 9, 2020

#100 When Investors Take the Hot Seat

Investors Jake Chapman and Howie Diamond switch roles to pitch their venture capital fund, exploring the intricacies of post-seed investments and redefining bridge rounds, while sharing their groundbreaking founder support program that revolutionizes mental health and leadership in startups.
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Episode Highlights

  • Role Reversal

    Jake Chapman and Howie Diamond, typically on the investor side, faced a role reversal as they pitched their venture capital fund to potential LPs like , , and . Jake described the experience as challenging, noting the pressure of being in the spotlight and the vulnerability that comes with pitching 1. He humorously remarked, "It sucked because we were on the other side of the table," highlighting the stark contrast between being an investor and a pitcher 1. This unconventional pitch was held back for three years due to legal constraints, adding to the unique nature of the episode 2.

       

    Strategy Feedback

    Feedback from potential LPs was crucial as Jake and Howie presented their investment strategy, which focused on bridge rounds. expressed concerns about the limitations of this approach, suggesting it might restrict deal flow and capabilities 3. and Charles Hudson4. Jake acknowledged the feedback, stating, "I worry about being criticized for strategy creep," as they considered adjusting their focus to include earlier stages 3.

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