Out-of-Pocket

What Out-of-Pocket does

Out-of-Pocket (Out Of Pocket Health, LLC) is a Brooklyn-headquartered, founder-led healthcare education and community platform founded in 2020 by Nikhil Krishnan, a former CB Insights senior research analyst and TrialSpark partnerships lead. The company operates a multi-product ecosystem anchored by a free weekly newsletter (~30K+ subscribers, 58% open rate) that translates healthcare business mechanics, regulation, and industry trends into plain-English analysis with a humor-driven editorial voice, supported by a podcast (~7,500 listeners), a deep library of paid cohort courses (Healthcare 101, Legal Stuff for Telemedicine, Legal Stuff for Healthcare Software, Healthcare Call Center 101; ~$850 each, 1,000-1,500 signups per cohort run), and a recurring slate of curated events including the annual Knowledgefest conference (~$850-$950/ticket, capped at ~80-100 attendees) and multiple themed hackathons (AI, Hardware, B2B Edition, Google, Ship It, Data Camp).

The platform's core revenue mechanics combine four streams: (1) paid admissions to courses and selective events, (2) tiered sponsorship packages sold to healthcare technology vendors (newsletter, podcast pre-roll, hackathons, Knowledgefest), with named partners including Abridge, Canvas Medical, Google HAI-DEF, Stedi, Vanta, Deerfield Management, and a long tail of supporting sponsors, (3) enterprise packages (OOP For Business) and adjacencies like OOP Coworking and a headhunting/talent marketplace via Pallet, and (4) low-volume branded merchandise and novelty products. Distribution is fully digital and direct, sold via outofpocket.health with email-list-driven acquisition; free hackathons function as a top-of-funnel acquisition mechanism for paid events and sponsor leads.

The company remains privately held by its founder with no disclosed institutional funding, operates with a small team (1-10 employees, including founding team member Danielle Poreh, former Head of Operations at Better Health), and serves a narrow but highly engaged audience of healthcare operators, digital health founders, and product/clinical-ops professionals. Its competitive position is built on brand voice, an application-gated community, and the compounding value of a sponsor-participant network, rather than proprietary technology or scale economics.

Name

Out-of-Pocket

Legal name

Out Of Pocket Health, LLC

Website

https://outofpocket.health

Company type

Private

Founded year

2020

Operating status

Operating

Headcount range

1–10 employees

Short description

Out-of-Pocket is a Brooklyn-based, founder-led healthcare education and community platform founded in 2020 by Nikhil Krishnan. It serves healthcare operators, digital health founders, and product/clinical-ops professionals through a newsletter (~30K subscribers), paid courses, hackathons, and the curated Knowledgefest conference, monetized primarily via sponsorship and course/event admissions.

Ownership category

akta.pro rank

Headquarters

HQ city

Brooklyn

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B and B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D, Others

Revenue model

1. Event Tickets: Paid admission to Knowledgefest conference ($950 for 2026, $850 for 2025) and other events. Application-based selective events create demand.
2. Course Enrollment: Paid courses including Healthcare 101 Crash Course, Legal Stuff for Telemedicine Companies, Legal Stuff for Healthcare Software, and others at $850 per course.
3. Sponsorship: Newsletter sponsorship (banner ads, full page analysis), podcast sponsorship (pre-roll), course sponsorship, event sponsorship (hackathons, conferences, dinners). Newsletter has 58% open rate, 32K+ readers.
4. Merchandise: Sale of novelty products including Medical Bankruptcy: The Game, Six Stages Of Grief Coasters, VBC Hoodie, and book 'If You Give a Mouse Metformin'.

Pricing tiers

Go-to-market motion2 records

Distribution channels3 records

Marketing channels8 records

Core offering

Out-of-Pocket operates a healthcare education and community platform that makes the business of healthcare accessible through a free weekly newsletter, a podcast, paid cohort-based online courses, and exclusive in-person events. Revenue is generated from individual course/event fees, B2B sponsorship placements across content channels, and branded merchandise. The company targets healthcare operators, founders, and technology professionals seeking practical, plain-English education on the U.S. healthcare industry.

Product overview

Out-of-Pocket is a curated professional community and content platform focused on making healthcare technology business accessible. The platform operates as a multi-product ecosystem centered around educational content and community events. Core offerings include a weekly newsletter (30K+ subscribers), multiple online courses covering healthcare fundamentals and specialized topics (Healthcare 101, Legal Stuff for Telemedicine, Healthcare Call Centers), and a podcast featuring healthcare operations discussions. The company organizes signature events including Knowledgefest (annual healthcare operations conference), multiple hackathons (Healthcare AI Hackathon, Hardware Edition Hackathon, B2B Edition Hackathon), and dinners for community building. Additional offerings include a job board, novelty products like Medical Bankruptcy: The Game, branded merchandise, and various sponsorship opportunities for companies seeking to reach healthcare operators.

Differentiator

Problem solved

Functional benefit

Products and services

• Out-of-Pocket Newsletter A free weekly email newsletter providing analysis on healthcare trends, business insights, and industry memes targeted at healthcare technology professionals and founders.
• Healthcare 101 Crash Course A cohort-based crash course teaching the basics of US healthcare in a simple and fun way, covering stakeholders, money flows, and industry trends.
• Legal Stuff for Telemedicine Companies Course Educational course covering legal and regulatory requirements for telemedicine companies.
• Legal Stuff for Healthcare Software Course Educational course covering legal and regulatory requirements for healthcare software products.
• Healthcare Call Center 101 Course Course teaching how to build and operate healthcare call centers.
• Knowledgefest Conference An intimate, invite-only annual summit for healthcare operations leaders featuring workshops, debates, and networking. The 2026 edition is scheduled for October 10-17 in San Francisco, CA.
• Hardware Edition Hackathon A hackathon event focused on combining hardware with AI tools to build healthcare applications. The event takes place in San Francisco from April 17-19.
• AI Hackathon: The B2B Edition A hackathon focused on the business side of healthcare AI, including claims, revenue cycle, prior auths, and B2B workflows. Held in New York City.
• Healthcare AI Hackathon A generative AI-focused hackathon for healthcare innovation, held in San Francisco.
• Out-of-Pocket Podcast A podcast covering healthcare operations, featuring interviews and discussions with healthcare technology leaders.
• OOP Job Board A talent marketplace connecting healthcare companies with job candidates, hosted on Pallet.
• Medical Bankruptcy: The Game An educational card game teaching players about why healthcare expenses are a leading cause of bankruptcies in the US.
• VBC Hoodie Branded merchandise featuring value-based care messaging.
• Six Stages Of Grief Coasters Novelty merchandise featuring healthcare-themed coaster designs.
• Newsletter Sponsorship Sponsored content opportunities in the OOP newsletter, reaching over 32K+ readers with 58% open rate. Includes banner ads and full page analysis options.
• Podcast Sponsorship Pre-roll advertising opportunities on the OOP podcast, reaching over 7,500 listeners focused on healthcare operations.
• Sponsored Courses Co-created educational courses on healthcare topics, typically generating 1000-1500 signups per run, free for attendees.
• Hackathon and Event Sponsorship Sponsorship opportunities for OOP hackathon events, including conferences, dinners, and hackathons with live audiences of 150+.
• Enterprise Packages (OOP for Business) Enterprise packages that bundle Out-of-Pocket's courses, events, and content access for healthcare companies purchasing seats for their teams.

Named customers6 records

Segments3 records

Ideal customer profiles2 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature1 record

Partnerships

27 partnerships are on record, tiered core, supporting and flagship.

• AbridgecoreGTM or Marketing PartnerAbridge sponsors OOP events and newsletter. Abridge is a healthcare AI company focused on clinical documentation. Sponsors newsletter, hackathons, and Knowledgefest to reach healthcare operator audience.
• Canvas MedicalcoreTechnology or IntegrationCanvas Medical is the most programmable EMR. Sponsors hackathons providing API access for participants to build healthcare applications. Integral technology partner for hackathon projects.
• Google (HAI-DEF)coreTechnology or IntegrationGoogle Health AI Developer Foundations (HAI-DEF) provides open weight models for healthcare AI including MedGemma. Sponsored hackathons and provided healthcare AI tools for participants.
• StedisupportingTechnology or IntegrationHealthcare clearinghouse providing APIs for eligibility and benefit verification checks. Sponsored hackathons providing developer tools for participants building healthcare applications.
• VantasupportingGTM or Marketing PartnerTrust management platform for healthcare compliance (SOC 2, HIPAA, HITRUST). Sponsored hackathons to reach healthcare startups building compliant products.
• Deerfield ManagementflagshipStrategic or Co-development PartnerHealthcare investment firm partnered with OOP for Healthcare AI Hackathon: The B2B Edition. Brings real healthcare business problems, backend workflows, and wish lists for hackers to address. May provide customer connections.
• Cure (NYC venue)supportingOthersCure hosts the Healthcare AI Hackathon: The B2B Edition in NYC as the event venue.
• Photon HealthsupportingGTM or Marketing PartnerHealthcare technology company sponsoring hackathons and events.
• KeragonsupportingGTM or Marketing PartnerHealthcare workflow automation company sponsoring hackathons.
• ArlosupportingGTM or Marketing PartnerHealthcare technology company sponsoring hackathons.
• PhenomlsupportingTechnology or IntegrationHealthcare AI company whose APIs were used by hackathon participants for AI-powered workflows in Carely project.
• CambersupportingGTM or Marketing PartnerHealthcare technology company sponsoring hackathons.
• ImpilosupportingGTM or Marketing PartnerHealthcare operations company sponsoring Knowledgefest.
• SuperDialsupportingGTM or Marketing PartnerHealthcare communication platform sponsoring Knowledgefest.
• VerifiablesupportingTechnology or IntegrationHealthcare data verification platform sponsoring Knowledgefest.
• MerokasupportingGTM or Marketing PartnerHealthcare marketing platform sponsoring Knowledgefest.
• NirvanasupportingGTM or Marketing PartnerHealthcare technology company sponsoring Knowledgefest.
• TellescopesupportingTechnology or IntegrationHealthcare communication platform sponsoring Knowledgefest.
• AwellsupportingTechnology or IntegrationHealthcare workflow platform sponsoring Knowledgefest.
• MedallionsupportingGTM or Marketing PartnerHealthcare technology company sponsoring Knowledgefest.
• LuminaisupportingGTM or Marketing PartnerHealthcare technology company sponsoring Knowledgefest.
• Candid HealthsupportingGTM or Marketing PartnerHealthcare revenue cycle management company sponsoring Knowledgefest.
• Foley (Nathaniel Lacktman)supportingStrategic or Co-development PartnerNathaniel Lacktman, partner at Foley and chairman of the American Telemedicine Association Board of Directors, presenting on digital health law at Out-Of-Pocket 2026 Retreat. Provides legal expertise to community.
• Retell AIsupportingTechnology or IntegrationVoice AI platform used by hackathon participants for automated phone calls in projects like ARC referral automation and Clinicians Unchained prescription follow-up.
• ReplitsupportingTechnology or IntegrationNo-code/low-code platform used by hackathon participants to build UIs without engineering experience.
• MedplumsupportingTechnology or IntegrationHealthcare development platform used by hackathon participants for EHR integration and clinical workflows.
• OurasupportingGTM or Marketing PartnerWearable health technology company sponsoring hackathons and attending Knowledgefest.

Scale indicators8 records

Recent moves6 records

Expansion highlights5 records

Direct peers

• Histalk: Long-running healthcare IT news and commentary site serving health system operators and technology buyers. Comparable as an independent, founder-led healthcare media brand targeting the same operator buyer.
• 4sight Health: Healthcare thought leadership and publishing platform producing commentary, reports, and events aimed at healthcare industry operators and executives. Comparable in its operator-focused healthcare publishing and events model.
• MedCity News: Healthcare business and innovation news outlet covering digital health, providers, payers, and policy for industry professionals. Comparable as a healthcare-focused business media brand with overlapping B2B audience and event sponsorship model.
• Rock Health: Digital health advisory and research firm that produces reports, events, and community programming for healthcare founders and enterprises. Comparable as a healthcare-focused research, advisory, and community platform with overlapping audience and B2B sponsorship model.
• Hospitalogy: Healthcare operations-focused newsletter and community that covers the business of healthcare for operators and digital health builders. Closely mirrors Out-of-Pocket's audience, content format, and operator-centric positioning, making it the most direct comparable.

Broad incumbents

• CB Insights: Market intelligence platform with a dedicated healthcare research vertical that produces newsletters, reports, and events for enterprise buyers. Notably, OOP's founder previously led the healthcare research team here, building a 90K+ subscriber newsletter — making it a direct predecessor model and a broader incumbent in the same content category.
• HLTH: Large-scale annual healthcare conference and community serving providers, payers, startups, and sponsors. Comparable as a healthcare event business with sponsor monetization, but at significantly larger scale and broader scope than Knowledgefest.
• Bessemer Venture Partners: Large venture firm that publishes widely-read cloud and healthcare industry research (e.g., State of the Cloud, healthcare roadmaps) used by operators and founders. Comparable as a high-distribution healthcare research and content brand, though embedded inside a broader VC platform.
• Andreessen Horowitz (a16z Bio + Health): Major venture firm with a Bio + Health practice producing podcasts, essays, and frameworks consumed by healthcare founders and operators. Comparable as a high-reach healthcare thought leadership brand, though part of a much broader firm.
• KLAS Research: Healthcare IT research firm producing reports and ratings used by provider operators and enterprise technology buyers. Comparable as a healthcare-focused research and insights business targeting the same operator buyer, but with a more enterprise/B2B research model.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat6 records

Key risks6 records

Key highlights6 records

Customer concentration

• Xtwitter.com/nikillinit
• Instagraminstagram.com/outofpockethealth
• LinkedInlinkedin.com/company/outofpockethealth

Revenue estimate

Valuation estimate

Number of profiles

Profiles2 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Out-of-Pocket