This Week in Startups

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

44 snips
Dec 29, 2025
Zach Kidd, founder of Ask Humans, introduces an innovative AI platform designed to capture and analyze open-ended feedback for organizations. He discusses the impressive use cases at private clubs and city agencies. The conversation delves into the importance of user preferences for feedback modalities, including audio and AI follow-ups. Jason also shares his thoughts on avoiding private jet purchases in favor of investing in startups. They explore the future of vertical SaaS amid evolving AI technologies, emphasizing product-market fit.
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ANECDOTE

Why Jason Avoids A Private Jet

  • Jason resists buying private aviation despite wealth due to cost and cognitive load.
  • He prefers simpler purchases and staying humble to avoid extra life complexity.
ADVICE

Handle Outlier Customers Honorably

  • If an early customer proves unusual, be honorable: finish the project, hand over source code, or offer training.
  • Consider raising price or converting the work to a bespoke, profitable engagement.
ADVICE

Control Inbound VC Meetings

  • When VCs reach out, research them and log every contact in a CRM to retain control.
  • Say you are not raising and schedule a future meeting window to increase their interest and keep ball control.
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