Perplexity Does Shopping

Plus: Google's tests, HBO back at Max

Author

Joey Padgett
May 15, 2025

Welcome back to Forests Over Trees, your tech strategy newsletter. It’s time to zoom-out, connect dots, and (try to) predict the future.

Here’s today’s plan:

  • Tool of the Week — tools you’ll find useful

  • Tech News Takes — digestible analysis and commentary

  • F/T Shoutouts — sharing other cool stuff we’ve found

Perplexity Does Shopping

Plus: Google's tests, HBO back at Max

🛠️ Tool of the Week 🛠️

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⚡ Tech News Takes ⚡

Perplexity and PayPal Team up for Shopping

  • What’s up: Perplexity is partnering with PayPal to bring one-click, in-chat shopping to its AI interface, letting users book travel, buy products, and get tickets using PayPal or Venmo. PayPal will manage payments, shipping, and customer support. The deal comes as Perplexity nears a $500M funding round at a $14B valuation.

  • So what: Because Perplexity is struggling compared to OpenAI and the other frontier AI model companies, we’re seeing them run a ton of experiments, including this one. But it seems like a good idea to me! Perplexity’s “answers plus sources” approach to AI chat could be a great fit for shopping. It’ll give you confident answers like an LLM but with easy ways to buy right in the chat. Plus they’re partnering with Paypal… Google should be worried about this.

  • What’s up: Google is testing a new "AI Mode" button in Search, which could eventually replace the long-standing “I’m Feeling Lucky” feature. Some users have reported seeing the AI chatbot access point either inside the search bar or below it with a distinctive rainbow animation. AI Mode offers a chatbot-style response to search queries. Google says the test is limited to a small percentage of U.S. users for now, with no confirmed plans for a full rollout.

  • So what: I couldn’t help but include another Google-related story that relates to the Perplexity one. They’re apparently testing (and struggling to decide, probably) where their AI chat features should go. And it’s hard, because they don’t want to mess with the Golden Goose (search/ads revenue), but they need to move fast before Perplexity and others steal share. It’s a classic case of the innovator’s dilemna.

  • What’s up: Warner Bros. Discovery is rebranding its streaming service back to HBO Max later this summer, reversing its 2023 decision to simplify the name to just Max. The original change aimed to highlight non-HBO content, but that strategy appears to have flopped—especially as the company recently axed kids’ programming like Looney Tunes and Sesame Street and started labeling shows as “HBO Originals” again. CEO David Zaslav framed the reversal as a move to leverage the HBO brand’s premium reputation to drive global growth.

  • So what: It’s great to hear that they’re embracing HBO again… Speaking from experience, shows like The Wire, Silicon Valley, and Entourage don’t grow on trees. But for Warner Bros and Zaslav, it has to be painful to know they spent a few years going down the wrong path.

  • What’s up: Airbnb is rolling out a major app redesign and repositioning itself as a full-service travel platform. The update introduces a new “Airbnb Services” tab that lets users book chefs, personal trainers, photographers, and more in over 100 cities worldwide — even if they’re not staying at an Airbnb. The company is also launching “Airbnb Originals,” exclusive experiences like pastry classes and behind-the-scenes tours that aren’t available on rival platforms.

  • So what: This is a good idea, but it’s not surprising. They’ve tried launching new revenue streams on the site a few times. And as we’ve discussed before, they need to! But what’s new and interesting here is that they’re launching “services”. Importantly, these aren’t just for travelers or special occasions. You can book a massage, a hair appointment, a photographer — things you might need even if you aren’t on vacation in a cool new city. Basically, that means diversified revenue for Airbnb, in ways that aren’t all dependent on the travel industry.

🤖 AI Demos 🤖

It’s easy to feel overwhelmed by AI. There are SO MANY tools being launched, and it’s hard to know where to start.

Let’s fix that!

For the next few weeks, I’m continuing an experiment… I’ll pick tools everyone’s talking about, apply them to specific scenarios, and then report back. And for each tool/scenario, you’ll get my unfiltered review and a step-by-step walkthrough of what I did.

I’ll be the crash test dummy, and you can follow along, run your own demos, or suggest new tools I should try.

Sound good?

Ok. Here’s the second AI demo (link to the first here)

AI Demo #2 — Make a Spotify Copycat Using v0

  1. What does it do: v0 helps you mock up the user interface (UI; frontend) of pet projects, websites, app ideas, etc. And it drafts the code behind the scenes too.

  2. The good: Really easy to start. In 30 seconds, you have a visual starting point. So if you’re solo, you can build from there and make it real, weaving the code into your project. And if you’re on a team, you can use it to iterate and reach consensus with them about what needs to be built. As a product manager in big tech, this would absolutely speed-up my ideation cycles and earn trust with my UX and developer teammates.

  3. The bad: Let’s go from least to most important… First, this is nit-picky, but even after much coaxing it wasn’t able to throw in placeholder album art, which irritated the perfectionist in me. Second, v0 seems to be stubborn about its initial design choices and applies most edits as bolt-ons rather than removing/reconsidering the original work (your mileage may vary). Third, as you continue to chat/iterate, the iterations take longer… it would be better if it asked a quick set of probing questions to ensure understanding before taking the minute or two to run updates (it ran in the wrong direction a few times).

  4. Step-by-step demo: Spotify Copycat Using v0

  1. Go to v0.dev — it’s free to start and no log-in required

  2. Tell it what you want to build

  3. Let it cook!

  4. Check out what it made.

    Here’s the frontend code of the Spotify Copycat it made (the green numbers just represent lines of code; +’d when those files are added to by your iterating…

    …and without further ado, here’s the preview/mockup…. not bad!


  1. If you have other ideas or edits, just comment in the chat and v0 will incorporate.

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