🤩Perplexity Gets Celebrity Investor

PLUS: Gates' Daughter Raises $30M | Gemini Gains On ChatGPT

December 08, 2025

Reading time: 5 minutes

🗞️In this edition

  • Cristiano Ronaldo invests in Perplexity AI startup

  • Sponsored: i10x - All-in-one AI workspace

  • AI shopping startup founded by Gates' daughter raises $30M

  • Google Gemini narrows gap with ChatGPT leader

  • In other AI news –

    • AI deepfakes fuel a new wave of health misinformation

    • Meta expands its AI wearable vision with Limitless

    • OpenAI pulls app suggestions after user backlash

    • 4 must-try AI tools

Hey there,

Cristiano Ronaldo is now an investor in Perplexity, Phoebe Gates is raising big money for her AI shopping startup with Hollywood backing, and ChatGPT is watching Gemini pull ahead in global growth.

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Let's get into it.

What's happening:

Billionaire footballer Cristiano Ronaldo has taken stake in Perplexity AI, marking the Portuguese star's most high-profile investment to date.

Perplexity also entered a global sponsorship agreement with Ronaldo and launched an interactive hub for fans on its search engine.

Founded in 2022, Perplexity has emerged as the fastest-growing AI startup, positioning itself as a direct challenger to Google. The San Francisco-based company was valued at $20B in a September funding round and has been expanding enterprise tools, paid subscriptions, and international footprint amid surging demand for AI search alternatives.

Ronaldo, currently based in Saudi Arabia, has a net worth of about $1.4B according to Bloomberg Billionaires Index. Until now he has primarily invested in home country Portugal, focusing on smaller businesses like the 2024 acquisition of Lisboa Racket Center, hotel chain, gyms, and media group.

The investment comes weeks after Ronaldo met with US President Donald Trump in Washington, an encounter widely shared on social media after Trump posted a video. While neither side disclosed details, it sparked online speculation about potential commercial or promotional ties.

Why this is important:

Celebrity investor backing Perplexity signals mainstream awareness of AI search as Google alternative, not just tech insider bet.

$20B valuation in September positions Perplexity as one of highest-valued AI startups behind OpenAI and Anthropic despite being founded just in 2022.

Sponsorship agreement with interactive fan hub suggests Perplexity using Ronaldo's 900M+ social media followers for user acquisition, not just capital.

Ronaldo meeting Trump weeks before investment sparking "speculation about commercial or promotional ties" is notable given Trump administration's tech policy influence.

Our personal take on it at OpenTools:

Undisclosed stake size plus simultaneous sponsorship agreement plus interactive fan hub means this is a marketing partnership, not serious venture capital.

Ronaldo has $1.4B net worth but primarily invested in Portuguese hotels, gyms, and racket centers until now. He's not a tech investor. This is brand play for both sides.

Perplexity gets access to 900M+ followers across Instagram, Facebook, Twitter. Ronaldo gets equity in a $20B company for endorsement. That's value exchange unrelated to Ronaldo's investing expertise.

The Trump meeting timing is interesting. Ronaldo meets Trump, weeks later invests in a US AI startup. Coincidence or was Perplexity opportunity discussed? We don't know but timing raises questions.

Perplexity positioning as Google challenger at $20B valuation is aggressive. They're competing with companies worth $2T with dominant search distribution. Celebrity investors don't change that competitive reality.

The "interactive hub for fans" on Perplexity's search engine is an attempt to drive usage. If Ronaldo's followers try Perplexity because of him, some might stick. That's user acquisition strategy through celebrity partnership.

This validates the trend of AI companies seeking celebrity investors for distribution, not capital. Perplexity raised $20B at $20B valuation in September. They don't need Ronaldo's money. They need his audience.

Similar to Kim Kardashian backing companies or athletes investing in startups. It's brand alignment and audience access, not venture capital expertise.

For Perplexity, worth it if even 0.1% of Ronaldo's followers become active users. For Ronaldo, worth it if Perplexity's valuation appreciates and he maintains relevance in tech space.

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What's happening:

Phoebe Gates, daughter of Bill and Melinda French Gates, is raising $30M for Phia, a startup applying AI to online shopping, at a $180M valuation. This comes just months after completing an $8M seed round in September.

Phia, which Gates cofounded with Sophia Kianni, is backed by Hailey Bieber, Kris Jenner, Sheryl Sandberg, and Sara Blakely. Bill Gates hasn't invested but publicly supports the startup, Phoebe told Vogue.

Notable Capital is leading the round under managing partner Hans Tung, whose earlier investments include Anthropic and Airbnb. Kleiner Perkins and Khosla Ventures are also participating.

Phia's AI-based search engine, offered as an app and browser extension for Chrome desktop and Safari mobile, helps users find items, compare prices, and spot deals. The tool has been downloaded 750,000 times in eight months through November.

In its pitch deck, Phia compared itself to fast-growing agent startups: Harvey (legal, $8B valuation), Mercor (HR, $10B), and Cursor (software development, $29.3B).

Gates and Kianni began working on the company in their Stanford dorm room, initially coming up with "the idea of a Bluetooth tampon before pivoting to fashion," they told Vogue.

Why this is important:

$180M valuation after eight months and 750K downloads shows how quickly AI agent startups can raise at high valuations regardless of revenue or proven business model.

Celebrity backing (Bieber, Jenner, Sandberg, Blakely) signals this is more lifestyle/fashion positioning than enterprise AI. That's a different investor profile than typical B2B agent companies.

Comparing to Harvey ($8B), Mercor ($10B), and Cursor ($29.3B) in pitch deck is aspirational positioning. Those companies serve professional markets with clear ROI. AI shopping comparison tool serves consumers with unclear monetization.

Notable Capital leading with Hans Tung (Anthropic, Airbnb investor) brings credibility but also shows VC willingness to bet on celebrity-adjacent consumer AI despite uncertain path to profitability.

Our personal take on it at OpenTools:

$180M valuation for AI shopping comparison tool with 750K downloads and no disclosed revenue is bubble pricing.

Price comparison and deal-finding isn't novel. Honey (acquired by PayPal for $4B) did this without AI. Karma, ShopSavvy, Wikibuy all exist. Phia's differentiation is "AI-based search engine" but pitch deck doesn't explain how AI improves on existing solutions.

Celebrity backing matters for consumer brand awareness but doesn't validate product-market fit or business model. Bieber and Jenner investments signal fashion/lifestyle positioning, not technical merit.

750K downloads in eight months is respectable traction but doesn't indicate active usage, retention, or monetization. Download counts are vanity metrics without engagement data.

Comparing to Harvey, Mercor, and Cursor is reaching. Those companies serve professional buyers (lawyers, HR, developers) who pay for productivity tools. Phia serves consumers who expect shopping tools free and subsidized by affiliate commissions.

The $180M valuation assumes Phia captures a meaningful share of e-commerce discovery with a path to monetization matching its comps. Both assumptions are uncertain. Consumer shopping behavior is fickle and competition from Amazon, Google Shopping, and existing price comparison tools is fierce.

What's happening:

ChatGPT's growth is tapering off according to Sensor Tower data. OpenAI's chatbot remains the leader with 50% of global mobile downloads and 55% of monthly active users, but Google's Gemini is outpacing ChatGPT in download growth, monthly active user growth, and time spent in app.

ChatGPT's global monthly active users grew only 6% from August to November, reaching roughly 810 million, suggesting the AI chatbot is nearing market saturation. Gemini's monthly active users jumped 30% during the same period as its Nano Banana image generation model drove adoption.

ChatGPT saw its share of global monthly active users drop three percentage points over four months (August-November 2025), while Gemini increased its share by three percentage points over seven months (May-November).

Gemini users now spend 11 minutes per day in the app, up 120% from March. ChatGPT users' daily time spent increased only 6% during the same period and was down 10% in November compared to July.

Perplexity and Claude saw triple-digit growth in 2025, up 370% and 190% year-over-year respectively. ChatGPT's 85% download growth lagged the cohort's 110% average, while Perplexity (215%) and Gemini (190%) saw the largest gains.

Android users engage with Gemini directly through the OS at twice the rate of the standalone app, providing competitive advantage in Android-dominated global markets.

Why this is important:

6% ChatGPT growth versus 30% Gemini growth from August to November shows momentum shift. The market leader is decelerating while the challenger accelerates.

ChatGPT losing three percentage points of market share in four months while Gemini gained three points over seven months indicates sustained trend, not temporary fluctuation.

Gemini's Android OS integration reaching 2x more users than standalone apps is a distribution advantage ChatGPT can't match. Android dominates globally with 70%+ market share.

Time spent declining 10% (ChatGPT November vs. July) while Gemini doubles to 11 minutes per day shows engagement shifting. Users aren't just trying Gemini, they're spending more time with it.

Our personal take on it at OpenTools:

This is a classic distribution advantage beating product quality.

ChatGPT has brand recognition and a first-mover advantage. But Gemini has Android OS integration, which means billions of devices with built-in access. That's distribution moat ChatGPT can't overcome with better products alone.

The 6% ChatGPT growth versus 30% Gemini growth from August to November is the inflection point. When the market leader grows slower than the challenger, the gap narrows inevitably. Math works against OpenAI here.

810 million monthly active users "suggesting market saturation" is a premature claim. Global internet users exceed 5 billion. ChatGPT hasn't saturated the market, it's saturated early adopters. The question is whether mainstream users adopt AI chatbots at all, or if this remains a power user tool.

Nano Banana driving Gemini's adoption is an important caveat. Image generation is a consumer-friendly use case. If Gemini's growth is primarily image generation users, they're a different cohort than ChatGPT's text-focused users. Not direct substitution.

Time spent in apps is a better metric than downloads. ChatGPT's 10% decline in November versus July shows engagement problems, not just acquisition slowdown. Users are trying ChatGPT less frequently or for shorter sessions. That's a retention issue.

ChatGPT's 85% download growth lagging 110% cohort average means it's not just losing to Gemini, it's losing to the entire category. Newer entrants are capturing a disproportionate share of new users.

This is a consolidation phase where distribution and ecosystem advantages matter more than pure product quality. OpenAI built the best chatbot. Google, Microsoft, and others have distribution. In consumer tech, distribution usually wins.

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