What Two Operators Learned Writing First Checks

Angel Academy Session 2 puts two founder-turned-investors on stage: Neal Bloom and Ashok Kamal. Both built companies, stumbled through first exits, and eventually landed on the investor side of the table. The conversation covers what actually changes when you go from pitching to writing checks — how to evaluate founders when there's nothing but a prototype, why saying no fast is a form of respect, and what most first-time angels get wrong about time horizons and portfolio construction. It's a candid, unscripted look at the operator lens that shapes how both of them deploy capital. Key Topics * Neal's founder-to-investor arc: aerospace to startups to fund manager * Ashok's path from recycled-backpack startup to NuFund * Why saying no quickly is the most respectful thing an investor can do * Being helpful versus intrusive as a post-investment supporter * First-check misconceptions: what new angels get wrong * Jockey versus horse — evaluating founders when traction is thin * NuFund's annual fund model and top-quartile performance * How to think about projections at the earliest stages Links & Resources * San Diego Angel Conference (SDAC): * NuFund Venture Group: * SDSU ZIP Launchpad: * Rising Tide Partners: Connect on LinkedIn * Neal Bloom: linkedin.com/in/nealbbloom * Ashok Kamal: linkedin.com/in/ashokkamal This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit risingtidepartners.substack.com/

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What Two Operators Learned Writing First Checks is an episode from Tacos and Tech Podcast by Neal Bloom.

This episode is 65:18 long.

This episode was published on May 5, 2026.

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