Perplexity AI

Instacart

Perplexity AI

Perplexity uses a freemium model. The free tier gives unlimited basic searches powered by a standard model.

Perplexity Pro costs $20/month and gives access to more powerful frontier models from OpenAI, Anthropic and Google, alongside Perplexity's own, unlimited Pro searches, file uploads, and image generation. Perplexity Enterprise Pro is designed for businesses with team management and API access.

The company also recently introduced advertising through "sponsored follow-up questions" — a controversial move that some see as inevitable and others see as the beginning of the end for ad-free search.

Instacart

Instacart operates as a marketplace connecting consumers with personal shoppers and grocery retailers. Revenue comes from multiple streams: delivery fees and service fees charged to consumers (typically $3.99+ per delivery), tips to shoppers (passed through, not revenue), retailer partnerships (grocers pay Instacart for access to the platform and fulfillment services), and advertising.

Advertising has become the crown jewel. Instacart Ads lets consumer packaged goods (CPG) brands like Coca-Cola, Procter & Gamble, and Nestlé pay for sponsored product placements within the Instacart shopping experience.

When someone searches for "chips," Doritos can pay to appear first. This is incredibly valuable because it's advertising at the exact moment of purchase intent.

Ad revenue was $871 million in 2023 and crossed $950 million in 2024.

The retailer partnership model is key. Unlike DoorDash or Uber Eats (which listed restaurants without permission early on), Instacart works with grocers as partners.

Over 1,500 retail banners including Costco, Kroger, Albertsons, and Publix have formal partnerships. Instacart provides the technology and shoppers.

Grocers provide inventory and stores.

Perplexity AI

Aravind Srinivas grew up in Chennai, India, got a PhD in AI from UC Berkeley, and worked as a research intern at OpenAI and a researcher at DeepMind. He watched the ChatGPT explosion in late 2022 and saw something everyone else missed: AI chatbots were interesting, but AI-powered search was potentially more valuable.

Google search hadn't fundamentally changed since 1998. It still showed you a list of links and made you do the work of reading and synthesizing information.

Srinivas co-founded Perplexity AI in August 2022 with Denis Yarats (ex-Meta AI), Johnny Ho (ex-Quora), and Andy Konwinski (co-creator of Apache Spark). Their idea was an "answer engine" — you ask a question, Perplexity searches the internet in real time, reads the sources, and gives you a synthesized answer with inline citations.

No ads. No SEO spam.

Just answers.

The product launched quietly and grew through word of mouth among researchers, developers, and knowledge workers who were frustrated with Google's increasingly ad-cluttered, SEO-gamed results. Within a year, Perplexity was handling millions of queries daily.

Instacart

Apoorva Mehta was a 26-year-old Amazon engineer in Seattle who quit his job in 2012 to start a company. The only problem: he had no idea what to build.

Over the next year, he started and abandoned roughly 20 different projects. A social network for lawyers.

A way to track restaurant wait times. Nothing stuck.

Then one day he was too lazy to go grocery shopping. He looked for a service that would shop for him and deliver everything to his door.

Nothing good existed. The existing options were grocery store delivery services that only worked during specific windows, had limited selection, and required ordering days in advance.

Mehta wanted to order groceries the way he ordered everything else online — immediately, from whatever store he wanted.

He built a prototype in 2012 and applied to Y Combinator. The demo was rough — he ordered a six-pack of beer through the app and had it delivered to a YC partner's house during the application process.

It worked. He got in.

Instacart launched in the San Francisco Bay Area in 2013 with a simple promise: order from your favorite local grocery store and have someone shop for you and deliver within an hour.

Perplexity AI

Perplexity grew almost entirely through product quality and word of mouth. The first users were AI researchers and tech workers who shared it on Twitter.

Every time someone used Perplexity and got a better answer than Google, they posted about it. The product was its own marketing.

The mobile app was a growth accelerator. By launching on iOS and Android early, Perplexity captured users who wanted quick answers on their phones.

The app was faster than opening a browser and Googling — one tap, ask your question, get an answer. Mobile usage now exceeds desktop.

Strategic distribution deals expanded reach. Perplexity partnered with SoftBank (default AI assistant on SoftBank phones in Japan), Deutsche Telekom, and various hardware manufacturers to be pre-installed as the default search assistant.

These deals put Perplexity in front of millions of users who had never heard of it.

Instacart

Instacart grew by solving a problem one city at a time. They launched in San Francisco, proved the model, then expanded to other major metros.

Each new market required recruiting shoppers, signing up retailers, and building enough consumer density to make the economics work.

The COVID-19 pandemic was the inflection point. Grocery delivery went from luxury to necessity overnight.

In March 2020 Instacart announced it would add 300,000 shoppers, then raised that by another 250,000 weeks later. Order volume increased 500%.

Years of planned growth happened in weeks. The pandemic proved that grocery delivery wasn't a niche — it was the future of how a significant chunk of the population would shop.

The enterprise play is the long-term moat. By providing white-label technology to grocers, Instacart becomes embedded in their operations.

Even if a grocery chain wanted to build its own delivery service, they'd need years and hundreds of millions to replicate what Instacart provides. The more deeply integrated Instacart becomes in grocery operations, the harder it is to rip out.

Perplexity AI

Google is the elephant in the room. Google controls 90%+ of the search market and generates $175 billion annually from search advertising.

Google has responded to Perplexity by adding AI Overviews to search results — essentially copying the answer engine concept. Google has unlimited data, unlimited compute, and the default position on every browser and phone.

Competing with Google for search is historically a death sentence.

The publisher problem is real and litigious. Perplexity synthesizes content from news articles and websites without driving traffic back to those publishers.

Multiple media companies have accused Perplexity of scraping their content and delivering it as answers, depriving them of page views and ad revenue. The New York Times, Forbes, and Condé Nast have all raised concerns.

If publishers successfully block Perplexity or win legal challenges, the product's utility decreases.

Monetization without ads is nearly impossible at scale. Perplexity initially positioned itself as the ad-free alternative to Google.

But $20/month subscriptions can't fund the compute costs of an answer engine serving hundreds of millions of queries. The introduction of sponsored questions signals that pure subscription revenue isn't enough.

Whether Perplexity can add ads without becoming what it set out to replace is the defining question.

Instacart

The post-COVID hangover was brutal. After pandemic demand normalized, growth slowed dramatically.

The company's valuation dropped from a peak of $39 billion in early 2021 to about $10 billion at IPO in September 2023. Investors who bought at the peak saw a 75% paper loss.

The narrative shifted from "essential infrastructure" to "nice-to-have luxury."

Unit economics are perpetually tight. Paying a person to walk through a grocery store, pick items, bag them, and drive them to someone's house is expensive.

Unlike meal delivery (one restaurant, one bag), grocery delivery involves dozens of items per order, refrigeration requirements, and substitution decisions. Every order that requires a shopper to call the customer about an out-of-stock item eats into efficiency.

Amazon is the existential threat. Amazon Fresh, Whole Foods delivery, and Amazon's own logistics network represent a competitor with nearly unlimited resources and a Prime membership base of 200+ million.

Amazon has been willing to lose billions on grocery delivery to build market share. Instacart's advantage is retailer partnerships — Kroger and Publix use Instacart specifically because they don't want to help Amazon dominate grocery.

Perplexity AI

Perplexity Search is the core — ask any question and get an AI-synthesized answer with cited sources. Pro Search performs multi-step research, asking clarifying questions and digging deeper for complex queries.

Perplexity Pages lets users create shareable research articles from their queries. Collections organize saved searches and threads.

The Perplexity API lets developers integrate the answer engine into their own products. Perplexity recently added Spaces for team collaboration on research projects.

Instacart

Instacart Marketplace — the core platform where consumers order groceries from 80,000+ stores for delivery or pickup, with personal shoppers fulfilling orders. Instacart+ — subscription service ($9.99/month) offering free delivery on orders over $35, reduced service fees, and credit back on pickup orders.

Instacart Ads — a retail media platform letting CPG brands run sponsored product listings, display ads, and coupons within the shopping experience. Instacart Platform (Enterprise) — white-label e-commerce technology that lets grocers build their own online ordering and fulfillment powered by Instacart's infrastructure.

Caper Cart — AI-powered smart shopping carts (from the 2021 Caper AI acquisition) with built-in screens, barcode scanners, and payment that let shoppers skip the checkout line.

Perplexity AI

Jeff Bezos, IVP, NEA, Databricks Ventures, Nvidia, SoftBank

Instacart

Sequoia Capital was an early and consistent backer. Andreessen Horowitz invested in growth rounds.

D1 Capital Partners led the 2021 round that valued Instacart at $39 billion. Existing investors including Valiant Capital, T.

Rowe Price, Fidelity, and Tiger Global participated across rounds. Y Combinator was the starting point (Summer 2012 batch).

The September 2023 IPO on NASDAQ priced at $30 per share, valuing the company at approximately $10 billion.