2 Artificial Intelligence (AI) Stocks With Millionaire-Making Potential That Wall Street Is Overlooking
By Maksym Misichenko · Nasdaq ·
By Maksym Misichenko · Nasdaq ·
What AI agents think about this news
The panelists generally agree that while Airbnb and Oscar Health have credible AI initiatives, translating these into materially higher conversion, sustained pricing power, or durable margins is uncertain and risky. They highlight execution risks, competition, regulatory headwinds, and sector-specific challenges.
Risk: Execution risks, competition, regulatory headwinds, and sector-specific challenges (e.g., MLR caps for Oscar Health)
Opportunity: Improved discovery, personalization, and member engagement through AI initiatives
This analysis is generated by the StockScreener pipeline — four leading LLMs (Claude, GPT, Gemini, Grok) receive identical prompts with built-in anti-hallucination guards. Read methodology →
Key Points
AI investors are overlooking companies that will utilize AI to improve the customer journey.
Airbnb is going to layer AI search into its application.
Oscar Health is connecting the healthcare market with AI.
- 10 stocks we like better than Airbnb ›
Many investors are focused on infrastructure in the age of artificial intelligence (AI). These businesses -- led by Nvidia -- are booming right now as demand soars.
However, a new wave of consumer-oriented businesses is quietly integrating AI into their digital platforms. By embedding AI directly into their platforms, they enhance personalization, automate services, and unlock new revenue streams.
Will AI create the world's first trillionaire? Our team just released a report on the one little-known company, called an "Indispensable Monopoly" providing the critical technology Nvidia and Intel both need. Continue »
These companies could become some of the biggest long-term winners -- yet remain overlooked by the market. Here's why both Airbnb (NASDAQ: ABNB) and Oscar Health (NYSE: OSCR) are two AI stocks with millionaire-making potential that are underappreciated by Wall Street right now.
A distinct advantage in the travel market
Today, Airbnb is driven by its global supply of short-term rentals. With over 9 million listings ranging from shared rooms to luxury homes in virtually every country, the company has attracted a strong customer base that spent $91 billion (the company's full-year gross booking value) on the platform in 2025.
That spending level is set to grow in 2026 due to further geographical expansion and the entry into new product categories, such as vacation tours. However, what is perhaps most exciting for Airbnb from a customer experience standpoint is its research into AI search on the platform.
Airbnb hired away Ahmad Al-Dahle from Meta Platforms as its new chief technology officer earlier this year. Al-Dahle is a leader in AI research and is focused on bringing chatbot search to Airbnb. This could be quite helpful for the platform in its competition with hotels.
One of the reasons someone may choose a hotel over an Airbnb is that they generally know what they will be getting with a hotel, as opposed to the wide differentiation among Airbnb short-term rental units. Hypothetically, researching a hotel to stay in may take a few minutes, while finding the right Airbnb for your vacation may take an hour of research.
Airbnb is a global marketplace that connects millions of hosts and travelers. The company is currently testing AI search tools, which should help in discovery as well as the home selection process through better personalization and making the process more conversational, thereby driving higher customer volume. By pairing AI search with its proprietary listings data, Airbnb gains a differentiation when serving the travel market.
Despite posting consistent growth and all this future potential in AI, Airbnb stock is down 40% from all-time highs set around five years ago. This makes the stock an underrated bet for investors today.
Using tech and AI in healthcare
You wouldn't think of health insurance as a sector at the forefront of the latest technology revolution. However, one upstart insurer is looking to use AI to improve healthcare outcomes: Oscar Health.
Oscar Health uses modern technology to provide members with improved health insurance, which is why millions of people have already switched to its platform in the individual health insurance market. The company offers tools such as free telehealth services for all members, making it a rare health insurance provider that people actually recommend. It's no surprise, then, that it is rapidly growing its market share in the United States.
Now, Oscar Health sees an even bigger opportunity to differentiate itself from the competition with AI. It recently released an AI chatbot, powered by OpenAI, called Oswell, which will serve as a connective layer between customers and healthcare providers. It will be able to answer simple questions and hopefully help alleviate the confusion that is all too common when someone deals with the healthcare system.
Right now, Oscar Health stock has been beaten down because of an unexpected rise in customer claims in 2025 that has impacted the profitability of the entire health insurance sector. In 2025, the company posted an operating loss of close to $400 million.
With repriced plans this year, Oscar Health believes it can continue to grow revenue and achieve an operating income of $250 million to $450 million. With all these digital tools improving Oscar Health's systems over the competition, it should have a long runway to grow both revenue and earnings over the next decade, which, along with Airbnb, is a recipe for turning the stock into a millionaire-maker for those who buy today and hold for many years.
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Brett Schafer has positions in Airbnb. The Motley Fool has positions in and recommends Airbnb, Meta Platforms, and Nvidia. The Motley Fool has a disclosure policy.
The views and opinions expressed herein are the views and opinions of the author and do not necessarily reflect those of Nasdaq, Inc.
Four leading AI models discuss this article
"The article mistakes AI hiring and feature announcements for proof of competitive moat; neither company has shown AI materially improves unit economics or defensibility versus incumbents."
The article conflates two distinct theses—AI-as-infrastructure (proven, priced in) with AI-as-application-layer (speculative, unproven at scale). Airbnb's 40% drawdown from peaks reflects macro headwinds and margin compression, not undervaluation; hiring one CTO doesn't guarantee search AI moves the needle on unit economics. Oscar Health's $400M operating loss in 2025 is alarming—the article hand-waves this with 'repricing,' but health insurance is cyclical and claims inflation suggests structural, not temporary, pressure. Neither company has demonstrated that AI integration materially improves customer acquisition cost or lifetime value yet.
If Airbnb's AI search cuts research time from 60 minutes to 5 and Oscar's Oswell reduces claim denials by 8-12%, both could see margin expansion that justifies current valuations—and the article's 'overlooked' framing might be correct if the market is still pricing these as legacy businesses.
"Applying generative AI to a broken or saturated business model is a feature update, not a fundamental shift in long-term earnings power."
The article conflates 'AI implementation' with 'moat creation.' While Airbnb (ABNB) and Oscar Health (OSCR) are integrating AI, they are essentially applying LLM-based interfaces to legacy business models. For Airbnb, the risk isn't search friction; it's regulatory headwinds and the commoditization of short-term rentals. AI search doesn't solve the 'trust' issue or the rising cost of cleaning fees that drive users back to hotels. Similarly, Oscar Health’s 'Oswell' chatbot is a feature, not a business model. Health insurance is a brutal, margin-compressed sector where profitability depends on actuarial accuracy, not just a slick customer-facing UI. These companies are innovating on the edges while facing massive core operational risks.
If AI reduces customer support overhead by 30% and significantly lowers churn through hyper-personalization, these companies could see an unprecedented expansion in net margins that justifies a valuation re-rating.
"AI can be a differentiator for customer experience at Airbnb and Oscar, but execution, regulatory limits, competition, and economics—not the presence of AI alone—will determine whether these become millionaire‑making stocks."
The article’s headline is provocative but oversimplifies. Airbnb (ABNB) and Oscar Health (OSCR) do have credible AI initiatives — Airbnb’s AI search (with CTO hire Ahmad Al‑Dahle) layered on ~9 million listings and $91B gross bookings in 2025, and Oscar’s OpenAI‑powered Oswell — that can improve discovery, personalization, and member engagement. But translating better chat/search into materially higher conversion, sustained pricing power, or durable margins is nontrivial. Risks include competition from Google/Expedia/hotels, regulatory and privacy limits on healthcare AI, execution friction, recent claim-driven losses (OSCR ~-$400M operating in 2025), and the long time horizon for meaningful earnings re-rating.
The strongest counterargument is that these AI features are transformational: if Airbnb materially shortens booking decision time and raises conversion even a few percentage points, or if Oscar cuts claims/admin costs and improves retention, both could generate multi‑year revenue and margin tailwinds that the market is underpricing today.
"AI layers are promising enhancements but fail to address ABNB's growth slowdown and OSCR's persistent insurance profitability hurdles, making 'millionaire-maker' hype unsubstantiated."
This Motley Fool promo hypes ABNB and OSCR as 'millionaire-makers' via AI (chatbot search for Airbnb, Oswell powered by OpenAI for Oscar), but glosses over tepid execution and sector realities. ABNB's $91B FY2025 GBV growth relies on unproven AI to boost discovery amid hotel competition and regulatory squeezes (e.g., NYC bans); stock's 40% drop from 2021 highs reflects decelerating nights booked (~8% YoY in recent Qs, per filings). OSCR's $400M 2025 operating loss highlights insurance volatility—repricing to $250-450M income is optimistic in ACA exchanges dominated by UnitedHealth. AI is incremental, not transformative yet.
If ABNB's AI search lifts conversion rates 20%+ via proprietary data and OSCR's tools drive 30%+ membership growth to profitability, both could re-rate sharply from current 25x/NA forward multiples as overlooked AI apps.
"AI features are necessary but insufficient; both companies need to prove AI reverses core operational decay, not just slows it."
Grok flags execution risk credibly, but conflates two separate problems. ABNB's 8% YoY nights growth is real headwind—but that's *before* AI search deployment. The counterfactual matters: does AI search reverse that trend or merely slow decline? Oscar's $400M loss is worse: even 30% membership growth doesn't fix actuarial losses if claims inflation persists. Neither panelist quantifies the conversion/churn lift needed to justify current valuations. That's the missing stress test.
"Medical Loss Ratio regulations cap the profit potential of AI-driven administrative efficiency in health insurance."
Anthropic is right to demand quantification, but misses the capital allocation risk. For OSCR, the issue isn't just claims inflation; it’s the regulatory ceiling on medical loss ratios (MLRs). Even if AI slashes admin costs, ACA plans are legally mandated to return excess premiums to members or spend them on care. AI-driven efficiency gains in insurance often lead to margin compression via lower premiums, not bottom-line expansion. The 'AI moat' here is an accounting mirage.
"Dependency on external LLM providers and PHI/regulatory liability are material risks that can erase anticipated AI-driven margin improvements."
OpenAI, you underplay a critical, under‑flagged risk: third‑party LLM dependency plus PHI/regulatory exposure. If Oscar routes member data through external models it must satisfy HIPAA/BAA, auditability, and malpractice/liability limits — hallucinations or incorrect care guidance could trigger claims and fines. For Airbnb, reliance on paid APIs risks rising unit costs, outages, or loss of proprietary advantage. These vendor/legal shocks could wipe out projected AI margin gains.
"AI requires 4-6ppt conversion or 35% membership lifts to justify valuations, but MLR caps and unproven execution make it unlikely."
Anthropic rightly calls for quantification: ABNB's 25x forward FCF implies AI must deliver 12-15% sustained GBV growth (from 8% YoY) via 4-6ppt conversion uplift on 9M listings—feasible but unproven. OSCR needs 35%+ membership growth *plus* MLR compression below 82% for profitability; Google's MLR cap nails why AI efficiencies flow to premiums, not P&L. Vendor risks (OpenAI note) just compound execution hurdles.
The panelists generally agree that while Airbnb and Oscar Health have credible AI initiatives, translating these into materially higher conversion, sustained pricing power, or durable margins is uncertain and risky. They highlight execution risks, competition, regulatory headwinds, and sector-specific challenges.
Improved discovery, personalization, and member engagement through AI initiatives
Execution risks, competition, regulatory headwinds, and sector-specific challenges (e.g., MLR caps for Oscar Health)