What Two Operators Learned Writing First Checks

What Two Operators Learned Writing First Checks

From Tacos and Tech Podcast by Neal Bloom

May 5, 2026 · 1h 5m

About this episode

Neal Bloom and Ashok Kamal discuss their experiences transitioning from founders to investors and share insights on angel investing.

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): https://sdac.sdsu.edu * NuFund Venture…

People in this episode

Host: Neal Bloom

Guest: Ashok Kamal

Topics covered

  • angel investing
  • founder experience
  • investment strategies
  • evaluating startups
  • portfolio construction
  • first-check misconceptions

Keywords

  • angel investing
  • founders
  • investment
  • startups
  • portfolio
  • evaluating founders
  • first-check

Mentioned in this episode

Organizations: NuFund, San Diego Angel Conference (SDAC), SDSU ZIP Launchpad, Rising Tide Partners

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