On Perplexity - Timeline and Hypotheses [Updated]

I continue to update the timeline as news comes out. 

The latest update was made to the timeline and tracker on: September 12, 2025. 

I'm not editing other writing.

Check out my tracker spreadsheet here: Perplexity Table

~~~

Perplexity baffles me! 

It’s a fast-growing startup that has built a great product and is stirring competitive reactions from the likes of Google and OpenAI.

At the same time, it's sustainable competitive advantage is unclear, and it's saddled with growth expectations attached to a $3B valuation (maybe $9B). 

To help wrap my had around Perplexity, I created a running 2 year timeline to understand where they've been and help me think through where they might be going.

Read on for a fully sourced timeline of Perplexity's rise, covering:

• Fundraising
• Product Launches
• MAUs
• Revenue 
• Legal action
• and more

Food Delivery is Big Business

Links to source data below the fold 

On Jam.dev - Strategic Analysis

 

Jam.dev builds a browser extension that helps teams resolve bugs faster. It's cool, effective, and incredibly user-friendly!

I got a bit obsessed about understanding the business and here we are -  a strategic analysis of Jam.dev for fun. Read on for my take on:

• Adoption
• Product Overview
• Growth/Pricing
• Strengths
• Challenges
• Strategic path forward

As always, I’m certain to be missing loads of information and context, and would love to hear why I'm wrong. May this be useful to someone, in some fashion, no matter how small 🫡

I don't buy the "crypto 🤝 AI" narrative

For the betterment of the consumer, may I be wrong and eat my words 🫡

Arc Browser

 

Some quick thoughts on The Browser Company // Arc Browser. Arc is an internet browser that has raised $18MM and has gotten lots of pub.

For the betterment of the consumer, may I be wrong and eat my words 🫡

Humane AI Pin -- Quick Thoughts

I've been skeptical of the Ai Pin's chance for success since their interesting November 15, 2023 launch video. 

Now, having just watched Humane's 28 minute AI Pin Video Handbook I've got to put pen to paper.

For the betterment of the consumer, may I be wrong and eat my words 🫡

A boring view of today's A.I. startups

Josh Miler, CEO Browser Co, 03-25-24

Artifact shuts down and Particle raises $4.4M

Artifact closed shop in January 2024. Particle just announced a $4.4M round. Interesting! 

The State of (Business) Play - Venkatesh Rao

All credit goes to Venkatesh Rao. 

Original Post: The State of (Business) Play

This post is me splitting out the questions from that ^ post so I can most-easily refer back to them. 

Clubhouse: a tweet-sized memo

Some thoughts on Clubhouse.

This time around I'm trying to keep each section to a tweet-sized 280 characters. 

Some notes on moats

Below are 5 core resources for thinking through the development, maintenance, and evolution of economic moats.

Roam Research: Where is the moat?

These are some thoughts on Roam Research.

An interesting read [added 7-19-23]: The Fall of Roam by Dan Shipper

Pioneer (https://pioneer.app/) - Convexity Machine breakdown

This post breaks down Pioneer (https://pioneer.app/) in terms of being a Convexity Machine.

TLDR;
Pioneer exhibits nearly all of the characteristics of a Convexity Machine(CM).

However, Pioneer's central roles as the gatekeeper limiting participation and the sole Selector stop it short of being a fully fledged CM.

This suggests that Pioneer's only path to venture-scale is expanding both the number of gatekeepers that decide which projects make it into their accelerator and the number of Selectors that bestow status, money, and other rewards to projects.