Join me as I sit down with Jonathan Courtney to host the second annual “Sippy Awards,” the most prestigious award show in tech for the products, games, and tools that shaped 2025. We crown our most-hyped products for 2026, favorite games of the year, best productivity tools, and best products under $100. We also dive into analog tools like Traveler’s Notebook, hi-fi systems, Japanese porcelain, and simple clothing uniforms as ways to make everyday life better and de-fragment your brain.

Timestamps

00:00 – Intro

03:23 – Most Hyped Product of 2026

14:43 – Game of the Year 2025

19:49 – The Way to Innovate

25:41 – Premium Domains

29:56 – Best Productivity Product

42:02 – Favorite Product of 2025

54:10 – Best products under $100.

Key Points

The Sippy Awards are a playful but serious way for Greg and Jonathan to highlight the products and games that genuinely improved their lives in 2025.
They argue that cult classics (Wind Waker, Pinkerton, Kid A, Breath of the Wild, Elden Ring) come from creators who put the audience last and follow their own taste, even at the risk of initial backlash.
Distinctive visual identities and premium dot-com domains are framed as both trust builders for users and commitment devices for founders.
Their favorite productivity and lifestyle tools—ChatGPT, Things, Endel, Traveler’s Notebook, YouTube Premium, Japanese porcelain—show how small, well-crafted tools reshape daily workflows and rituals.
Analog practices (morning pages, notebooks, hi-fi listening) and simple clothing uniforms are presented as ways to de-fragment your brain, reduce decision fatigue, and focus on what matters.

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