The Startup Ideas Podcast

Sippy Awards 2025: Best Products of 2025 (Apps, Video Games, AI)

Date: November 28, 2025
Host: Greg Isenberg (A)
Guest: Jonathan Courtney (B)

Episode Overview

In this energetic and candid episode, Greg Isenberg and Jonathan Courtney host the Second Annual Sippy Awards, their tongue-in-cheek “Nobel Peace Prize of Tech Products.” They highlight their top picks for products across tech, AI, and consumer categories for 2025, share personal stories and philosophies on product design, and forecast the most anticipated launches for 2026. Expect deep dives into gaming, productivity, domain names, physical products, and the meaning of true innovation—delivered with a blend of humor, banter, and practical advice for founders and builders.

Key Segments & Insights

1. The Sippy Awards: Setting the Stage

[00:59–03:26]

• Jonathan humorously elevates the Sippy Awards above other accolades:

  “Getting one of these awards is bigger than getting something like a Red Dot Award or a Nobel Peace Prize...this is the high level stuff.” (B, 01:12)

• Award categories include:

  • Most hyped product of 2026
  • Best game of the year
  • Best productivity product
  • Best product under $100
  • Favorite/most used product of the year

2. The Most Hyped Product of 2026: Gaming Goes Big

[03:37–14:33]

Jonathan’s Pick: Half-Life 3 and the Steam Machine

• Jonathan dives deep into Valve’s “mythical” next installment, Half-Life 3, and its upcoming hardware:

  “If there’s any company that I copy and try to recreate for my business, it’s been Valve from day one.” (B, 06:26)

• Valve’s uniqueness highlighted:

  • Bootstrapped, private, $16B revenue, ~300 employees.
  • Launching Steam Machine (6x more powerful than Steam Deck), new controller, Steam Frame VR headset.

• The meme-ification of Half-Life 3’s vaporware status and what Valve means to the industry:

  “This is the most hype that’s ever happened around this product...people posting the Hopium meme.” (B, 08:10)

Greg’s Pick: GTA 6

• Greg mirrors the excitement around Rockstar’s decade-plus awaited release:

  “The two most hyped video games of all time ever.” (B, 12:20)

• They discuss the high bar for franchises like Zelda, Mario, GTA, and Red Dead Redemption, exploring why hype and expectations make or break major releases.

3. Reflections on Innovation, Subversion, and Making Cult Classics

[14:33–23:35]

• Jonathan draws inspiration from companies and artists who ignore audience expectations to create the new:

  “Designing things, ignoring the audience ... is one of the only ways to actually make innovative things that are special.” (B, 19:48)

• Parallels to art and music (Weezer’s Pinkerton, Radiohead’s Kid A, Nintendo’s Wind Waker and Breath of the Wild).

• Lessons for builders: Dare to be different; unique visual languages and radical choices can create scroll-stopping appeal and cult classics.

4. The Value (and Psychology) of Great Domain Names

[24:01–29:55]

• Domains are “waterfront property of the internet.” Both hosts agree strong .coms are only growing in value.
• Jonathan explains how buying alreadythere.com for ~$12K forced him to commit mentally and professionally to his IRL events project:

  “When I buy an expensive domain name, I mentally commit myself to the project.” (B, 28:32)

• Discussion on leasing-to-buy domain trends and war stories from domain transfers gone awry.

5. Best Productivity Product of 2025

[29:58–40:00]

Jonathan: ChatGPT

• Unapologetically basic but powerful pick.

  “It is just the most useful tool ever...it is my most used productivity product of all of 2025 by far.” (B, 30:10)

• Notes on ChatGPT Atlas browser (slow but groundbreaking agent feature), Gemini and Claude.

• Easter egg: Special call-out for the unique rainbow installation animation in Atlas:

  “When you move around the little installation box...it warps your screen. I’ve never seen that while installing a product.” (B, 33:48)

Greg: Things (by Culture Code)

• To-do list app; lauded for its “robust, clean” simplicity and lack of subscription.

  “Things is the only thing that gets me to stick to a to do list.” (A, 37:25)

• Both reminisce about classic app designs (Clear, Readable) and the enduring value of clean, delightful UI.

• Bonus mention: Endel (Berlin-based ambient sound app) as a beautifully crafted product that’s “delightful and convenient.”

6. Favorite/Most Used Product of the Year

[42:04–53:24]

Jonathan: Traveler’s Notebook (Midori)

• Physical notebook system that merges analog beauty, modularity, and practicality:

  “If you’re someone who keeps buying notebooks...the Traveler’s Notebook is...one notebook, one source of truth.” (B, 43:38)

• Great for both work and art; appeals across genders but under-covered by men in tech.

• Advocates for “Morning Pages” (from Julia Cameron’s Artist’s Way) as a powerful creative practice:

  “I’m mostly writing to get things out of my head.” (B, 46:35)

Greg: Yumiko Ihoshi Porcelain

• Elegant Japanese dinnerware line; small, calming, beautifully designed mugs and tea sets.

  “Every time I pour myself a cup of coffee...it’s so calming. It’s my favorite product of the year.” (A, 50:46)

• Reflection on why investing in daily-use items enhances overall well-being:

  “I'm looking at this thing every single day...that is incrementally making my life better.” (B, 52:54)

7. Best Product Under $100

[54:04–56:20]

Jonathan: Traveler’s Notebook

(Same as above)

Greg: YouTube Premium

• The essential “sanity” product for skipping ads and accessing YouTube Music:

  “If you’re not on YouTube Premium, I don’t know what you’re doing.” (A, 54:31)

• Tips for using YouTube Music for long Jazz/ambient compilations, plus using DBrowser for minimalist listening/workflow.

8. Lightning Round: Bonus Picks, Fashion, and Life Philosophy

[58:03–62:34]

• Jonathan shares his hybrid podcast attire—tuxedo top, shorts below (“just oil” joke).
• Greg’s bonus <$100 recs: Lululemon shorts and Fruit of the Loom T-shirts (six-pack for $19—a life hack for not worrying about stains).
• Jonathan recommends Vuori shorts as the “step up” from Lululemon.

Notable Quotes

• “If you dare to be different...you’re more likely to be scroll-stopping if it’s just a completely different visual language.” (A, 24:01)
• “ChatGPT is my favorite fucking productivity product of 2025. Couldn’t be more boring.” (B, 36:12)
• “I wanted to make something...that was harder to digest, but really just...coming from my soul.” (B, 24:48)
• “Optimizing for your day-to-day, not just for milestones...makes your life incrementally better.” (B, 52:54)

Timestamps & Key Segments

| Timestamp | Section/Highlight | | ----------- | -------------------------------------------------------------------------------- | | 00:59–03:26 | Sippy Awards Introduction, Award Categories | | 03:37–14:33 | Most Hyped Product 2026: Half-Life 3/Steam Machine, GTA 6 | | 14:33–23:35 | Innovation, Subverting Expectations, Cult Classics | | 24:01–29:55 | Domain Names as Commitment Devices | | 29:58–40:00 | Productivity Products: ChatGPT, Things, Endel | | 42:04–53:24 | Favorite Product: Traveler's Notebook, Yumiko Ihoshi Porcelain | | 54:04–56:20 | Best Product under $100: Traveler’s Notebook, YouTube Premium | | 58:03–62:34 | Bonus: Shorts, T-shirts, Attire, and Life Hacks |

Episode Themes & Takeaways

• Breakaway Innovation: Real game-changing products or designs rarely come from user wishlists. Ignore the crowd to create the next cult classic.
• Celebrate the Everyday: Investing in great daily-use products (notebooks, mugs, music) pays off more than splashy, occasional purchases.
• Building & Branding: Digital assets like domains can lock in psychological and practical commitment to new ventures.
• Analog Love: Even hyper-digital founders find daily joy in analog tools—physical notebooks, beautiful dinnerware—alongside top digital tools.

Memorable Moments

• Jonathan detailing the Hopium meme around Half-Life 3’s mythical status.
• The hosts trading stories about their cult fandom for Legend of Zelda: Wind Waker and how initial public derision can become legacy status.
• The “domain as commitment” story:

  “I'm using alreadythere.com for this one-off funnel.” (B, 26:33)

• A spontaneous product fashion show—with tuxedo tops and Lululemon shorts.
• Greg’s enthusiastic plug:

  “If you’re not on YouTube Premium, I don’t know what you’re doing.” (A, 54:31)

For founders, builders, and product lovers, this high-energy awards show offers both practical tools and timeless lessons in daring to be different.