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Generous Gifting Platform Overview

Aug 19, 2025

Overview

This episode of the Retail Genic podcast features Kyle Montgomery, founder of Generous, an agentic gifting platform. Scott Wingo interviews Kyle about his entrepreneurial journey, the challenges of agentic commerce, and the future of AI-driven shopping agents in retail.

Kyle Montgomery’s Background & Journey

  • Kyle is a first-time founder with 15 years of experience in e-commerce, consulting, and agency leadership roles (Accenture, Fluid, Astound Digital).
  • He identified a personal pain point—managing gifts for 20 nieces and nephews—which inspired the founding of Generous.
  • Transitioned from full-time employment to founding Generous, moving part-time before committing fully in early 2025.
  • Influenced by books like "The Lean Startup" and emphasizes quick iteration and customer feedback.

Generous: Product & Vision

  • Generous is a web-based agentic platform focused on simplifying gifting for busy individuals.
  • Users can sync contacts, provide selected information, and receive AI-driven gift recommendations for various occasions.
  • The platform can reach out to recipients for preferences, aiming to make gifting more personal and effective.
  • The initial beta will focus on gift cards, leveraging partnerships to offer a wide selection of brands.

Product and User Experience Details

  • Onboarding allows users to select which contacts to add and to provide relevant context for better recommendations.
  • The agentic shopping experience is chat-based, with no traditional search/listing page—recommendations are given in chat with options for feedback.
  • Payment and checkout are handled within the chat, using a marketplace model with partnered retailers.

Business Operations & Go-to-Market

  • Generous is in its pre-seed fundraising round and has a CTO co-founder, advisers, and contractor support.
  • The platform is building a user wait list and offers referral incentives to move up the queue.
  • Beta launch is expected in Q3 2025, focusing on user and recipient feedback to refine the AI experience.

Industry Trends & Agentic Commerce Future

  • AI is rapidly becoming central to e-commerce, with predictions that 25% of consumer transactions will be delegated to AI by 2030.
  • Agencies and brands must adapt their operations and infrastructure for increasing agentic transactions.
  • The potential decline in direct-to-consumer websites and shift to agent-driven purchases could disrupt existing retail tech stacks.

Reflections on Agentic Frameworks & Marketplaces

  • The five-level autonomous agent framework aligns with Generous' vision—balancing human involvement with AI efficiency.
  • Discussion on whether gifting should remain personal or become more automated; Generous aims to keep humans "in the loop."
  • Marketplaces face the "cold start problem," and strategies are discussed for growing both user and retailer bases.

How to Connect & Participate

  • Users can join the wait list at meetgenerous.com, with options to advance by referring friends.
  • Kyle Montgomery is most active on LinkedIn and also available on Twitter (@kmont7).

Action Items

  • Q3 2025 – Generous Team: Launch Generous beta focusing on gift cards.
  • TBD – Interested Users: Sign up for the wait list at meetgenerous.com and share with friends to advance position.
  • TBD – Kyle Montgomery: Read "The Cold Start Problem" as recommended.

Key Dates / Deadlines

  • Q3 2025: Planned Generous beta launch focusing on gift cards.

Questions / Follow-Ups

  • Will users adapt to a fully chat-driven, agentic shopping journey without traditional product listings?
  • How effective will recipient outreach and onboarding be in enhancing gift personalization and platform growth?
  • What further partnerships or feature expansions are planned post-beta?

Full transcript