Choosing Your AI Surface for 2026

Big thanks to The TBOY Podcast for today’s shout-out. Special welcome to co-host Nick (yes, he subscribed!) and everyone new joining us from their circle.

We launched beta.thinkampersand.com, a new AI-first website built with Lovable, Supabase, MailerLite, and Resend. I’m personally leading this build. Please try it out, explore, ask your AI to use it and send me your feedback. 😅

🔦 2026 Strategic Planning in the Age of AI

We stand at a turning point: strategy for 2026 can’t just be about updating budgets or tweaking last year's roadmap. AI is rewriting what’s possible as a foundation for what’s next. How we think about devices, workflows, and competitive edges must shift now.

⚡ Quick Hits

• Venmo and PayPal are now tightly integrated, not just in features but in how data travels across both. If you use Venmo, double-check your privacy settings:

  • Set your default transaction audience to Private

  • Make your Friends List invisible

  • Review what you share.

    Just because Venmo feels casual doesn’t mean everything should be publicly visible, especially now that the PayPal universe is coming in.

    ‼️ Adjust Your Venmo Privacy Settings ‼️

• Meta just announced its new smart glasses lineup, headlined by the Ray-Ban Meta Display, their first pair with a built-in lens display. You can check messages, get directions, or control apps with a wristband. They’re flashy, but they raise real questions around weight, battery, and privacy. Available September 30 in the U.S. starting at $799.

• The ultra-thin iPhone Air hit stores last Friday, and while performance and cameras are getting praise, design choices and UI changes are sparking concern.

  • “Liquid Glass” is gorgeous, until it’s hard on your eyes.

  • The slimmer builds look sleek, but reports are already slipping out about battery trade-offs.

  
  💡 I want maximum immersion or maximum presence, not straddleing less of both. First time clearly articulating this thought, yes this is exactly how I feel, and what bothers me about the smart phone interface!

🛠 Tool

Gemini in Chrome
Google has embedded Gemini AI directly into Chrome for U.S. desktop users. It now offers:

• Tab summarization

• Context-aware browsing assistance

• AI-mode right in the address bar

🍿 This marks the main street shift from “browser as tool” to “browser as agent.” (TechCrunch) Remember Comet from Perplexity, we talked about it here just last week, I would say they have met their distribution match.

🪨 The Pebble

When you plan for 2026, don’t just choose tools. Choose your AI surface. 

That’s the interface where intelligence meets your customers.

It might be the browser, lovable built native apps, it might be wearable or hybrid, or maybe something novel.

Sketch what that surface looks like today and in 18 months.

Resources & workflows that align to that surface will tend to win.

🎒 Takeaway

Don’t wait to build around the old foundations. 2026 strategy needs both form and intelligence: decide where your AI lives (device, browser, agent), what tools it uses, and how payments/data/workflows support it. The early mover in selecting & optimizing that AI surface will have leverage.

— Alejandro Jaegerman

📊 Poll

✉️ If someone forwarded this to you, you can subscribe at MondayThought.com.

📢 Shoutouts!

• Thanks again Nick (From TBOY) not just for the shoutout on the pod, and signing up, but for always inspiring me and so many to remian informed, engaged and excited about the future. I mean it bud.

• Welcome Nick Garofolo, our new Business Development Partner – Professional Services & Digital Transformation, to Ampersand. Can’t wait to see how you will be raising our new biz game.

• 🍯 Shana Tova! May the year ahead be full of clarity, renewal, and courage.

Keep building, keep planning.

[#20] 👋 Feeling what 20th edition already? 50th edition, I’m looking at you. Have an amazing week everyone!