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

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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

Ignore the VCs, Speed is Not a moat

 

Value is created through innovation, but how much of that value accrues to the innovator depends partly on how quickly their competitors imitate the innovation. Innovators must deter competition to get some of the value they created. These ways of deterring competition are called, in various contexts, barriers to entry, sustainable competitive advantages, or, colloquially, moats. [Taxonomy of Moats - Reaction Wheel]

Food Delivery is Big Business

Links to source data below the fold 

Michael Mauboussin on Common Behavioral Biases in Investing and AI-Aided Countermeasures

Original Source: https://x.com/kevg1412/status/1956446117358625193

Behavioral Bias	Description	Impact on Investment Decision-Making	Mauboussin's AI-Aided Countermeasures
Overconfidence	Overestimating one's knowledge or ability to predict outcomes.	Leads to excessive risk-taking, concentrated bets, ignoring contradictory evidence.	Consciously seek disconfirming evidence; consider a wider range of outcomes; temper optimism with base rates. Use AI tools to surface counterarguments and less obvious risks, generate scenario analysis beyond your initial views, and aggregate probabilistic forecasts from diverse sources to calibrate your confidence.
Anchoring / Tunnel Vision	Fixating on an initial piece of information or a narrow set of inputs.	Prevents objective reassessment of investments; leads to missing alternatives or holding underperforming assets.	Explicitly consider a full range of alternatives; seek dissent and opposing arguments; "red team" your own ideas. Leverage AI to generate alternative scenarios and viewpoints, identify overlooked opportunities or risks, and simulate decision processes from the perspectives of other investors or market participants.
Hindsight Bias	Believing, after an event, that one had predicted or known the outcome all along.	Impedes accurate learning from past decisions; fosters false confidence.	Keep a decision journal, documenting rationale, information, and expectations before decisions are made. Employ AI to timestamp, catalog, and later analyze the original logic and context of decisions, ensuring post-outcome reflections are anchored to what was actually known and believed at the time.
Emotional Extremes	Making decisions under heightened emotional states (greed, fear, euphoria, stress).	Rapid erosion of decision-making skills; leads to irrational choices.	Postpone important decisions when emotionally charged; seek emotional poise. Use AI sentiment tracking to identify periods of heightened emotional language or erratic behavior in your records; set up automated reminders or restrictions to prevent trading or major decisions during high-stress periods.
Misunderstanding Incentives	Failing to recognize how incentives (financial/non-financial) shape behavior.	Leads to misjudging motivations of market participants or management.	Carefully consider all existing incentives and the behaviors they might motivate, including subconscious effects. Utilize AI to map and analyze incentive structures for all stakeholders, uncovering potential misalignments or hidden motivations that might influence outcomes in ways not readily apparent.
Overreliance on Intuition	Depending on "gut feelings" in complex, unpredictable environments.	Can lead to disastrous decisions in non-linear systems; fosters false sense of expertise.	Recognize when intuition is appropriate vs. when analytical rigor (System 2 thinking) is needed.
Base-Rate Neglect	Ignoring statistical averages in favor of specific, vivid information.	Leads to overly optimistic or pessimistic predictions; misinterpreting probabilities.	Always refer to base rates (reference classes) for more realistic probability estimates. Use AI to access, aggregate, and analyze large datasets to establish accurate base rates and reference classes, ensuring decisions are grounded in objective historical probabilities rather than anecdote or vivid detail.

What's the point of invoking the ghost of Steve Jobs?

"Steve Jobs would have never shipped this."

"No way would this happen if Steve Jobs were still alive and running Apple." 

Oh yeah? Which Steve Jobs are you referring to?

• The one who got pushed out of Apple?
• The one who ran NeXT into the ground?
• The one who thought search engines were useless?
• The one who oversaw the launch of a litany of miserable products like the Newton, Apple Lisa, the hockey puck mouse, MobileMe, Ping, or butterfly MacBook keyboard?

If you want to criticize Apple's direction, make the actual case! 

That'd be interesting and fun. 

But don't aura farm a deceased CEO's imaginary opinion about a feature shipped in an entirely different phase of Apple's life.