Headway

OpenAI

Headway

Headway makes money by taking a percentage of the insurance reimbursement for each session facilitated through the platform. When a patient sees a Headway-credentialed therapist and pays their copay, Headway processes the insurance claim and takes a service fee from the reimbursement before paying the therapist.

The model aligns incentives well. Headway only makes money when therapy sessions actually happen, which means they're incentivized to help therapists see more patients and reduce no-shows.

Therapists make more than they would on their own (because Headway's negotiated rates are often better than individual therapists can get), and patients pay only their insurance copay ($0-$50 typically) instead of full out-of-pocket rates.

Scale creates a data and negotiation advantage. With 40,000+ therapists on the platform, Headway can negotiate better reimbursement rates with insurers.

More therapists attract more patients. More patients justify better rates.

The flywheel spins.

OpenAI

OpenAI makes money primarily through API access and subscriptions. The API charges developers per token (roughly per word) for using GPT models in their applications.

ChatGPT Plus costs $20/month for individual users, ChatGPT Team is $25-30/user/month, and ChatGPT Enterprise is custom-priced. Microsoft pays OpenAI licensing fees and also resells OpenAI models through Azure OpenAI Service.

OpenAI's annualised revenue ran past $13 billion during 2025 and kept climbing from there, which is the kind of growth curve that normally only exists in a pitch deck.

Headway

Andrew Adams and Jake Sussman founded Headway in 2019 after watching people in their lives struggle to access affordable mental healthcare. The problem was specific and structural: most therapists operate as solo practitioners who don't accept insurance.

Not because they don't want to — because the process of getting credentialed with insurance companies, submitting claims, and chasing reimbursements is so bureaucratically painful that most therapists give up and go cash-only.

The result is a two-tier mental healthcare system. People with money pay $150-$300 per session out of pocket.

People without money either can't afford therapy or wait months for the few in-network providers available. Meanwhile, therapists who only accept cash are leaving money on the table — insurance pays reliably once the system works, and the patient pool is vastly larger.

Headway's solution was to build the infrastructure layer that makes insurance billing painless for therapists. They handle credentialing (getting the therapist accepted into insurance networks), claims submission, payment processing, and compliance — all the administrative work that therapists hate.

The therapist shows up, does therapy, and Headway handles everything else.

OpenAI

OpenAI was founded in December 2015 as a nonprofit AI research lab. The founding donors — including Elon Musk, Sam Altman, Peter Thiel, Reid Hoffman, and Jessica Livingston — pledged $1 billion with a mission to build artificial general intelligence (AGI) that would benefit all of humanity.

The idea was that AI was too important and too dangerous to leave in the hands of Google alone.

Sam Altman became chairman while Greg Brockman (former CTO of Stripe) became president. Ilya Sutskever, one of the most respected AI researchers alive, left Google Brain to become chief scientist.

The early team was stacked with world-class researchers who published their work openly — hence "Open" AI.

But AI research turned out to be staggeringly expensive. Training large models required millions of dollars in compute.

In 2019, OpenAI created a "capped-profit" subsidiary — investors could earn up to 100x their money, but profits beyond that would flow to the nonprofit. Microsoft invested $1 billion.

The mission was still to save humanity. The method now involved making a lot of money first.

Headway

Headway grew by solving the supply-side problem first. If you can get enough therapists on the platform and credentialed with insurance, patients will come because affordable therapy is in massive demand.

They recruited therapists with a compelling pitch: "keep doing therapy, we'll handle the business side."

Insurance partnerships were the growth unlock. Headway partnered with major insurance companies (Aetna, Cigna, United Healthcare, Anthem) to become an authorized credentialing partner.

This meant Headway could get therapists in-network faster and with less friction than the traditional process.

The mental health destigmatization wave amplified demand. Post-COVID, demand for therapy skyrocketed.

The conversation around mental health became mainstream. Headway was positioned perfectly to absorb that demand by connecting patients with affordable, insurance-covered therapists.

OpenAI

ChatGPT's launch in November 2022 was the growth strategy — it just wasn't planned that way. The team expected a modest research preview.

Instead, ChatGPT hit 1 million users in 5 days and 100 million monthly active users in 2 months, making it the fastest-growing consumer application in history. The product went viral because it felt like magic — for the first time, anyone could have a natural conversation with a machine that seemed to understand them.

The Microsoft partnership provided distribution at massive scale. Microsoft integrated OpenAI models into Bing, Office 365 (Copilot), GitHub (Copilot), and Azure.

Overnight, hundreds of millions of Microsoft users had access to OpenAI technology. Microsoft's $13 billion investment was the largest AI bet in history and gave OpenAI nearly unlimited compute.

The API created an ecosystem. Thousands of startups built products on top of OpenAI's models — from customer service bots to coding assistants to content generators.

Each API customer locked themselves into OpenAI's ecosystem, creating switching costs and recurring revenue.

Headway

Therapist retention is a challenge. Solo practitioners are independent by nature, and some leave the platform once they've built a full patient roster through Headway.

The platform needs to continuously demonstrate value beyond initial credentialing to keep therapists from going direct.

Insurance reimbursement rates are notoriously low. Therapists who accept insurance often earn 30-50% less per session than cash-pay rates.

While Headway negotiates better rates than individual therapists typically get, the fundamental economics of insurance-based mental healthcare remain challenging.

Regulatory complexity varies by state. Each state has different licensing requirements, insurance regulations, and telehealth rules.

Expanding to all 50 states means navigating 50 different regulatory frameworks, each with their own credentialing requirements and compliance standards.

OpenAI

The board crisis of November 2023 nearly destroyed the company. The nonprofit board fired Sam Altman as CEO on a Friday, citing a loss of confidence.

Within 48 hours, 95% of employees threatened to quit and follow Altman to Microsoft. By Tuesday, Altman was reinstated and the board was restructured.

The incident exposed the fundamental tension between OpenAI's nonprofit governance and its for-profit ambitions — a tension it finally addressed in late 2025 by restructuring the business as a public benefit corporation sitting under the original nonprofit.

The cost of training frontier models is eye-watering. Each new GPT generation costs hundreds of millions to train.

OpenAI is reportedly spending over $7 billion annually on compute. The company is burning through cash faster than almost any startup in history, which is why it keeps raising at higher and higher valuations.

If revenue growth slows before costs stabilize, the math gets ugly.

Safety concerns are not going away. Multiple prominent researchers have left OpenAI over disagreements about the pace of development versus safety research.

Ilya Sutskever, the chief scientist who was central to the board's decision to fire Altman, left in 2024 to start a safety-focused AI lab. The public debate about whether OpenAI is moving too fast — and whether its safety commitments are genuine — grows louder with every capability improvement.

Headway

Headway Provider Platform — the core system where therapists manage their practice: scheduling, credentialing, claims submission, payment tracking, and patient communications. Headway Patient Matching — a directory and matching service that connects patients with in-network therapists based on insurance, location, specialty, and availability.

Insurance Credentialing Service — Headway handles the months-long process of getting therapists accepted into insurance networks, reducing what typically takes 6-12 months to weeks. Claims and Billing Engine — automated insurance claims submission and tracking that eliminates the paperwork therapists dread.

Practice Management Tools — scheduling, intake forms, session notes, and telehealth capabilities integrated into one platform.

OpenAI

ChatGPT is the consumer chatbot — the product that made AI mainstream overnight. The flagship GPT models are multimodal, handling text, images, and audio in one system.

The OpenAI API lets developers integrate GPT into any application. DALL-E generates images from text descriptions.

Whisper transcribes and translates audio. Sora generates videos from text prompts.

GPT Store lets users create and share custom GPT agents. ChatGPT Enterprise gives businesses a private, secure version of ChatGPT with admin controls and no data training.

Headway

Andreessen Horowitz led the Series C at a $2.3 billion valuation. Accel and Thrive Capital invested in earlier rounds.

GV (Google Ventures) and Spark Capital also participated. The company has raised approximately $226 million total.

OpenAI

Microsoft ($13B), Thrive Capital, Khosla Ventures, Sequoia Capital, Founders Fund, Tiger Global, SoftBank, a16z