CONFIDENTIAL — Do not distribute · Data as of June 2026
Strategic Partnership Overview

The Pocket Protector

A health-insurance marketplace & concierge — built so new-to-Medicare beneficiaries can shop and enroll online, and only get on the phone when it counts.

Asset class 1

25+ proprietary tools, datasets & recommendation engines

The data layer and decision engines that make Medicare shopping accurate, transparent, and self-serve.

Asset class 2

Health-insurance concierge app

iOS & Android — a pre- and post-sale tool for every adult, not just those on Medicare.

Asset class 3

Proven DTC marketing funnels

Digital acquisition at a low cost to acquire.

79% chose self-serve in our first paid NTM test New-to-Medicare ≈ 2× commissions & longer LTV vs switchers ~$550 CAC

The new-to-Medicare opportunity

In TPP’s first paid new-to-Medicare acquisition test, 79% of leads chose self-service tools over an agent (Matchmaker test, May 11–Jun 29, 2026, n=271 — an early live test, not a forecast). New-to-Medicare (“NTM”) beneficiaries also tend to pay ~2× the commission and carry longer lifetime value than beneficiaries who are simply switching plans — but NTM is the harder sale, and that difficulty is exactly the gap we built it to close.

Why new-to-Medicare is hard

1. Many are a better fit for Med Supp + PDP than Medicare Advantage — a longer, harder sale:

  • Often requires a bank account, more personal details, a longer application, and underwriting questions.
  • A more complex commission matrix.
  • Deceptively “simple” to choose — it actually requires nuanced advice.
  • ~6-year expected LTV — total expected commissions ~$2,500–$3,500.

2. NTM consumers often need multiple conversations to close, which decimates the higher commission — versus a switcher, who often switches in a single sub-hour conversation.

How we win the economics

We drive better unit economics by keeping interactions digital and only getting on the phone when a beneficiary is highly likely to convert on that call. The tooling does the education and the homework up front, so expensive human time is spent only where it pays.

Capture the NTM consumer online, advise them accurately, and reserve the phone conversation for the moment it converts.

A team of industry operators

Founded to solve one problem: selling health insurance without having to get on a phone call.

LeadershipBackground
Michael Boshardy
CEO & Co-Founder
Medicare regulatory attorney; 10+ years in health insurance.
Jarret DiToro
Co-Founder
Former Chief Marketing Officer at GoHealth; built marketing in credit cards and mortgages before Medicare.
Patrick Kahn
Head of Engineering (Philippines)
Multi-exit founder and computer scientist.
Joe Wald
COO
15+ years in health-insurance marketing and generative-AI optimization.

Team & cost base

  • 12 US employees — 11 in Chicago plus 1 remote agent in Florida (engineering, product, insurance, finance, compliance/QA, sales & strategy). Chicago team in-office 2–3 days/week at the Wicker Park office.
  • 6 in Manila, Philippines — 4 engineers plus Jarret & Patrick.

~$90.6K/mo gross operating burn (US payroll $49,280, Manila $11,240, plus rent/tech/overhead), ~$70K/mo offset by an affiliated funding contribution (via NaviGap) → ~$20.6K/mo net. Full detail on the Financials tab.

Ownership & structure

The Pocket Protector is founder- and employee-owned, with no institutional investment.

NaviGap LLC — wholly owned by Michael Boshardy — is the parent and governing company of TPP.

An affiliated funding arrangement through NaviGap currently offsets most of TPP’s operating burn (detailed on the Financials tab). It is separable from, and not part of, an acquisition of the brokerage, and may be discontinued at NaviGap’s discretion.

Medicare shopping & quoting technology

Plan-level doctor networks vs Zelis · Sunfire · medicare.gov

Better than Zelis, Sunfire, and medicare.gov.

Differentiator: the ability to find the billing NPI at each facility. A provider (e.g., a PA) may look out-of-network because a different NPI at the location does the billing with the carrier — we resolve this, which we believe no competing tool does.

Transparent recommendation engine

Accurate, transparent, and nuanced — and it includes all Plan G and PDP options, not a commission-filtered subset.

Prescription formularies: as good as all other vendors.

The only online consumer lookup that works without creating or signing into a medicare.gov account (a high-friction step) — something Sunfire can’t provide.
Proprietary enrollment process enabling non-telephonic submissions with all appointed carriers (MA, Med Supp, and PDP).

Tools that make the Medicare decision easier

Employer tool

Our marquee product.

“Magic” Plan

Compare a beneficiary’s current MA plan against everything else in their ZIP — and learn whether it’s actually the best. Includes a “keep my doctor” variation.

Healthmaps

Coverage by location — see whether a plan covers the providers and facilities a beneficiary uses.

Deadline Tool

Customized per beneficiary so they never miss a Medicare deadline — harder than it sounds.

Matchmaker

Routes each consumer to the best-fit human agent.

The full toolset

21 free consumer tools, plus the broader datasets & recommendation engines — see the Technology tab.

Everything is available in Spanish today, with more languages targeted before AEP.

An actual brand & marketing strategy — with real results

A UX that works

Designed to be simple for the consumer to navigate end to end.

The Matchmaker funnel routes each consumer to the right path — self-serve, or the right human agent.

Digital strategy — experienced operators

~$550 CAC — a low customer-acquisition cost during AEP.

Further marketing detail available in diligence.

Current financial picture

Our standalone economics — carrier commissions against a lean, largely-offset cost base — are detailed on the Financials tab (cash basis, reconciled). Headline: ~$90.6K/mo gross operating burn, ~$70K/mo offset by an affiliated contribution → ~$20.6K/mo net; carrier commissions $67,611 to date, with 2026 year-to-date already ~2.5× full-year 2025.

The consumer app

For every adult — not just Medicare

Free to start (fees may be added over time).

Differentiating feature: take a picture of any medical bill or insurer bill and get (1) a plain-English summary, (2) an opinion on whether you should pay it, and (3) where applicable, a ready-to-sign-and-send appeal letter — including the relevant CPT codes, the specific issues to contest, and the correct address and method to send it.

The pre-sale and post-sale tool

The app gets us onto a consumer’s phone before they’re ready to buy insurance — proving value and expertise first — then becomes the post-enrollment companion.

Pre-sale acquisition and post-sale retention in one product.

Confidential strategic overview — our estimates; financial detail and methodology on the Financials tab.

Organization

A software company that happens to sell health insurance

A small senior team running continuously with a fleet of AI agents — lean headcount, strong operating leverage.

already public confidential, for this recipient characterized only (no infrastructure specifics)

Our team

An independent health-insurance company run by a lean, global team across Chicago, Florida, and Manila, with a fleet of AI agents running continuously alongside it. Click any name to see their focus and where they’re based.

A lean team across three time zones (Chicago, Florida, and Manila) provides near-around-the-clock coverage, with specialist partners supporting specific workstreams. Headcount confirmed during diligence.

Headquarters & model

Chicago, Illinois

Operating office at 1539 N Damen Ave, Unit 2S, Chicago, IL 60622. Public licensing address: 2045 W Grand Ave, Ste B, Chicago, IL 60612.

Operating model

Operating model

A lean human team sets strategy, compliance, and product; a fleet of AI agents executes data engineering, research, and operations continuously. Every production change to the data platform flows through a single governed gate (see "The BoshBot difference").

Entity structure

NaviGap LLC Founding entity · "Original Member" · manager The Pocket Protector LLC Illinois operating company (Medicare) CEO / sole Manager: Michael Boshardy ImagineQ, LLC Affiliate (futures / management relationship) subsidiary: LifeLink LLC founds / manages MSA / futures Co-founding governing member: ImagineIF Partners, LLC (FL)

Digital workforce

Named AI agents that run continuously. Functions and regions only — infrastructure specifics are withheld.

Hermes / "BoshBot"

Operations & deployment agent. Runs data-engineering jobs and is the single accountable gate for every production change.

Socrates

Medical-billing & insurance-dispute advocate. Decodes EOBs, drafts appeals; trains other agents.

Eman

Email-automation agent; manages structured outbound/inbound workflows.

Mikal

Data-acquisition agent running a statewide hospital price-transparency sweep.

IQMR

Medical-records OCR/extraction (printed + handwritten → structured data).

IQMM ("Mailman")

Document-triage OCR for the affiliate's life-settlement servicing workflow.

Plus a horizontally-scaled crawl fleet used for provider-directory data acquisition. (Bot roster is characterized, not enumerated as a headcount.) Source: internal operations records.

Technology

The product and the moat

A consumer platform built around the buyer (who they are, and where they are in the journey) on top of a proprietary provider-network data layer, run by an AI-native operation, and open where it builds trust.

A. The consumer platform — free tools built around the consumer

Live on thepocketprotector.com, powered by real CMS data. Rather than present an undifferentiated catalog, we route each consumer on two axes: which buyer they are, and where they are in the decision. Hover any tool below to see what it does and open it. Coverage figures are point-in-time (June 2026) and shift with the plan year.

8,083
Medicare Advantage plans
as of Jun 2026
7,389
Medigap rates
as of Jun 2026
9.5M+
providers indexed
every NPI in the national registry
48 + DC
states licensed · 15 languages
/licensing

The journey: four phases, one platform

Every tool earns its place by serving a specific moment, from a confused first-timer to a member we keep for years.

Phase 1

Educate & build conviction

Help a confused shopper understand their own situation before any decision gets made.
Phase 2

Recommend & enroll, grounded

Turn understanding into a plan that fits and sticks, anchored to real doctors, drugs, and budget.
Phase 3

Support & retain the app's job

After enrollment the mobile app takes over: Dorothy becomes the always-on advocate that keeps the plan working, and keeps the member.
Phase 4

Useful to anyone, anytime

Earn trust and traffic with tools that help no matter where someone is in the journey.

The three buyers we build for

Each arrives with a different problem. Our platform is designed to solve the specific one.

New to Medicare longest journey

The problem

A long, high-stakes decision that needs education before conviction. The platforms built to move employees off group plans steer everyone toward Medicare even when staying put is the better call. One example: when dropping a group plan would strip coverage from a spouse or dependent.

How we win

We teach first and give the honest answer, including "stay on your employer plan." Our Employer Group Coverage Lookup puts group versus Medicare side by side and flags the spousal-coverage risk the others ignore.

Medicare Advantage switcher retention risk

The problem

MA switchers are usually sold whichever plan has the flashiest benefits. That mismatch drives churn the next year and generates complaints (CTMs) that carriers penalize.

How we win

We ground every recommendation in the member's actual coverage, doctors, drugs, and preferences, so the plan we suggest is one they keep. Recommendations that stick mean lower churn and fewer CTMs, an outcome carriers reward.

Medicare Supplement rate-shopping

The problem

Medigap is hard to enroll in without help, and the plans are standardized: identical coverage at very different rates, so price is the real question. These members also skew higher-income, where surcharges like IRMAA bite.

How we win

We show standardized Medigap rates from every carrier in the state so the member finds the same coverage for less, pair it with the right Part D, and add high-income value like the IRMAA calculator and appeal, with an advisor on hand for the complex parts.

The full toolkit

Every free tool and guided experience, grouped by what the consumer is trying to do (around 35 in all), each on real CMS data. Descriptions and links from the live site, Jun 2026.

My situation — guided routing

Medicare Readiness Quiz

A 2-minute assessment that walks you through the Medicare Advantage vs. Medigap trade-off and points you to the right path.

New to Medicare Navigator

Routes people new to Medicare into tailored guidance based on their situation — turning 65, switching, employer-covered, or under 65 with a disability or ESRD.

Help Me Choose

A short questionnaire that sends you to a guided comparison, the right self-serve tool, or a licensed advisor based on your answers.

Part A & B Enrollment Wizard

Walks you through Medicare enrollment step by step — what to sign up for, when, and what it costs.
Shop & compare plans

MA Recommendation Engine Flagship

Produces personalized Medicare Advantage plan rankings from your ZIP, doctors, medications, and coverage priorities, with estimated total cost and direct enrollment links.

Medicare Advantage Plan Browser

Compare the Medicare Advantage plans available in your area by ZIP using real CMS plan and pricing data.

Medigap / Medicare Supplement Rate Browser

Enter your ZIP to compare real Medigap rates from carriers licensed in your state and find the lowest available premiums.

Medigap + Part D Recommendation

Pairs the most competitive Medigap supplement with a Part D plan optimized for your medications.

Part D (PDP) Plan Browser

Enter your ZIP to browse and compare the standalone Part D prescription drug plans available in your area.

Part D Plan Recommendation

Ranks Part D plans by your true annual drug cost based on your medications, pharmacy, and fill preferences.

ACA / Marketplace Plans (Under-65)

Enter your ZIP to compare ACA marketplace health plans for consumers not yet eligible for Medicare.
Check something specific

My Doctors

Build your doctor list and see which local Medicare plans cover them in-network.

Doctor Coverage Heat Map

Enter your ZIP to see which Medicare plans cover your doctors in-network across your area.

Network Coverage

One hub for four neighborhood heat maps: doctors, hospitals, urgent care, and skilled nursing, showing in-network density by plan.

Hospital Network Heat Map

See which 2026 Medicare Advantage plans are in-network at 3,000+ acute-care hospitals nationwide.

Urgent Care Network Heat Map

Check MA in-network coverage across 2,700+ urgent care centers across the country.

I-SNP / Nursing Facility Heat Map

See I-SNP and Medicare Advantage coverage at 6,600+ skilled nursing facilities.

Nursing Home Coverage Navigator

Get a personalized recommendation for a nursing-home resident, with cost scenarios and network checks.

Find a Doctor

Search by ZIP for local doctors and providers that accept Medicare.

Drug Cost Lookup

Enter your ZIP to see estimated costs and coverage for your medications across local Medicare plans.

GLP-1 Bridge Eligibility

Checks whether you qualify for ~$50/mo Wegovy, Zepbound, or Foundayo under Medicare.

ZIP / County Coverage Lookup

Enter a ZIP to see all Medicare plan options available in that service area — MA, PDP, and Medigap carriers.

Deadline Reminder

Answer a few questions to generate a personalized calendar of your Medicare enrollment deadlines and avoid late penalties.

Financial Help / Extra Help Screener

Enter household and income information to see which assistance programs you may qualify for — Extra Help, QMB, SLMB, QI, and other Medicare Savings Programs.

IRMAA Calculator & Appeal

Estimates your income-related Part B & D surcharge (IRMAA) and shows whether you qualify to appeal it with Form SSA-44.
Quality & facilities

Hospital Quality Search

Enter your ZIP to compare nearby hospitals using CMS quality data and see which Medicare plans accept them.

Nursing Home Quality Search

Enter your ZIP to compare nearby nursing homes using CMS ratings and quality measures.
Additional tools

Employer Group Coverage Lookup

Enter your ZIP to compare your employer-sponsored health plan against local Medicare options.

Current Plan Check

Securely look up your current Medicare coverage — by manual entry or insurance-card scan — to set a baseline before comparing options.

Match an Advisor

A short questionnaire that matches you with a licensed TPP Medicare advisor suited to your situation.

Remove My Info

Stop spam calls and protect your privacy: opt out of 23 data-broker sites, get on every do-not-call list, and generate a legal deletion letter.

Client Success Stories

Real case studies showing how TPP advisors helped clients save across VA coordination, Medigap timing, formulary changes, and IRMAA appeals.
Standalone experiences

Dorothy AI Chat

An AI Medicare assistant that compares plans, checks drug costs, and finds in-network doctors conversationally using live data.

Compare Flow

A guided side-by-side comparison with three paths — new to Medicare, switching, or drug-only — that returns matched results in minutes.

Help Center

A free support hub spanning claims & appeals, costs & savings, and enrollment & eligibility, with AI chat and a reference library.

Learn Hub

Plain-language Medicare guides and comparison tools, including state-specific content and access to licensed advisor support.

B. Dorothy — the always-on layer that spans the journey

Where the web tools are point-in-time, Dorothy is continuous: an AI Medicare agent in both chat and voice that stays with the member across the whole journey. She is the buyer-side agent from the founding thesis, shipped as a product, and the engine of phase-three retention — a primary driver of whether a member stays past their first enrollment. Phase three of the journey — support and retain — runs almost entirely here.

Dorothy — AI assistant

Chat + voice. Answers general Medicare questions, and — only with the member's consent — uses their saved coverage, plan, and bills for personal guidance. Built not to invent plan terms, network status, or prices.

My Plan & coverage

Tracks real coverage terms (deductible, out-of-pocket max, PCP/specialist/ER, drug rows). Connect via CMS plan, manual entry, Medigap plan letter, Part D, or insurance-card scan; carrier eligibility verification surfaces actual cost-share.

Bill help

Upload a medical bill; AI extracts and summarizes it, flags possible issues, and drafts appeal text — the "understand & contest your bill" workflow.

Provider & drug lookups

Find a doctor, check a doctor against a plan, drug-cost lookup, pharmacy & hospital search — the same provider-data moat, on mobile.

Calendar & key dates

Medicare enrollment dates and personal reminders so members don't miss a window.

Built for trust

Phone sign-in, explicit AI-consent gating before any personal-context AI, PHI-safe handling, CMS-backed + carrier-verified data, and "say when it's unknown" behavior.

Apple App Store ↗  ·  Google Play ↗Live consumer app. Capability description from the internal app brief, 2026-06-19.

C. The data moat — the largest Medicare dataset online

Per our data inventory (Mar 2026), aggregated from 16 federal sources (CMS, DOL, FDA, NPPES). We are aware of no platform that aggregates this breadth in one place.

17M+
data points · 16 federal sources
9.5M+
providers indexed (every NPI in the national registry)
8,083
Medicare plans · 543,886 formulary entries
23,289
employer plans · 40,844 employers

Plus 5,426 hospitals, 14,710 nursing homes, 22,059 ACA plans (2.2M rate records), and 7,389 Medigap rate estimates (276 carriers × 51 jurisdictions). The provider layer below is the in-network spine of this dataset.

Our differentiator is a proprietary plan → network → provider resolution layer that answers, fast: "Is this doctor, at this location, in-network for this plan, this year?" It is built by crawling each carrier's CMS-mandated FHIR provider-directory APIs (and PDF directories where no API exists), then reconciling every provider against the full national NPI registry (~9.5M providers).

This network layer powers the "Find a Doctor," "My Doctors," and neighborhood doctor-coverage tools — capabilities most comparison sites cannot offer because they lack the underlying data.

Source: internal engineering records. Infrastructure specifics withheld.

Current production coverage

≈63% of Medicare Advantage contracts (436 of 685) resolved to provider-network level.

In the pipeline

A large staged backlog of additional carriers (incl. a national plan-grain dataset exceeding one million providers) is built and queued to load.

Recommendation services

First-party scoring logic (provider, Part D, and Medigap recommenders) ranks plans on drug fit, network, premium, out-of-pocket, benefits, and Star ratings.

Durability of the lead: the moat is not the raw feeds, which are available to anyone; it is the integration, entity-resolution, and confidence-scoring layer built on top of them, the hard and expensive part to replicate. CMS's planned CY2027 standardization commoditizes raw feed access for everyone — which only increases the value of the integration layer we have already built.

D. Open source & transparency

Consistent with the alignment thesis, we publish our recommendation logic so that "no commission bias" is verifiable in code, not just claimed.

tpp-open MIT

"Open-source Medicare plan recommendation engine. Zero commission bias — verified by code." Scores plans on drug coverage, network, premium, OOP, benefits, Stars & SNP eligibility; a CI test scans the codebase for any commission/compensation signal.
github.com/The-Pocket-Protector/tpp-open ↗

tpp-dashboard

"Open-source orchestration for zero-human companies" — the AI-operations scaffolding.
github.com/The-Pocket-Protector ↗

Also public: tpp-employer-tool, medsupp-apps.

E. AI-native operations — "the BoshBot difference"

Governed by one agent

Every production data change flows through "BoshBot" via a standing ticketing process — a single accountable mover, with humans authoring and reviewing. Control + speed.

Fleet + adversarial review

Work is fanned out across many AI subagents, then adversarially verified before shipping — the documented accuracy gate behind the data assets.

Built to be read by AI

"AI discoverability": the platform is structured (JSON-LD, semantic HTML, clear provenance) to be a trusted source for AI assistants — answer-engine optimization as strategy.

Compliance posture includes a Business Associate Agreement for HIPAA-compliant AI use on health/financial data, and CMS marketing-compliance guardrails throughout. Production stack: Next.js / Cloud Run / CloudSQL Postgres.

F. Unit economics & capital efficiency

Unit-economics figures are our estimates from the investor model; the Matchmaker line is an early live test. Not audited.

~$550

digital CAC vs. competitors' >$2,000 — our case for first profitable digital-only economics

~$893

estimated member LTV (public-brokerage 3-yr avg commissions)

$2.90 / ~$392

cost per lead / cost per acquisition in an initial live test (Matchmaker, May 11–Jun 29, 2026)

79%

of test leads chose self-service over an agent — validates the digital-first model

The build-vs-buy case: the data moat, its free toolkit, mobile app, compliant AI agents, and multi-state licensure above were built lean. A strategic buyer would spend well over a year, at substantially higher cost, to replicate the dataset, tooling, and compliant-AI stack. That capital efficiency is a core part of the asset.

G. The agent-facing platform

The same data and engines, in the quoting-and-enrollment tool our licensed agents use — and a candidate for B2B licensing (see Business Model).

Where the consumer tools serve the member, our agent platform arms a licensed agent with the same provider-network data, drug pricing, and recommendation logic — turning judgment that used to live only in an experienced agent’s head into software a new agent can use on day one. Six capabilities set it apart from the quoting platforms agents use today:

In-network NP/PA cross-reference

Verifies in seconds whether a non-physician provider (NP/PA) bills under an in-network physician at the same location — a daily friction point where agents lose time, and where newer agents often wrongly tell a client their doctor is out of network when they are not.

Memory-medication compliance alerts

Flags medications such as memantine that may signal cognitive impairment in a client — protecting the client, the agent, and the agency’s license, since a beneficiary can present as lucid on a given day with no other visible signal.

C-SNP & SEP trigger alerts

Flags medications such as Eliquis that may qualify a client for a C-SNP plan, and surfaces the related Special Enrollment Period — capturing enrollments outside AEP that agents on other platforms miss entirely because they have no way to know to look.

Multi-plan benefit search

Search a specific benefit (e.g., implants) across every plan at once, instead of opening each plan’s EOC or SOB one by one. Agents still confirm in the official documents, but now know exactly which plans are worth checking.

True dollar-for-dollar cost sorting

Combines premium, copays, and drug costs to rank plans by what actually saves or costs the client the most, in real dollars — updating live as doctors or medications are added. The math an experienced agent does in their head, automated, and a knowledge-gap closer for newer agents.

Med Supp vs. MAPD, side by side

Puts a Medicare Supplement and a Medicare Advantage proposal on one page — something most platforms don’t attempt, since the products differ fundamentally — so the agent can guide a client to the right category of coverage, not just the right plan within one.
Consumer App

An AI advisor and medical-bill helper for anyone with health insurance

Our mobile app (iOS & Android) is built for anyone with health insurance — employer, ACA/Marketplace, Medicaid, or Medicare — not Medicare members alone. Two features anchor it: Dorothy, an AI advisor that answers coverage questions in chat or by voice from the member’s own plan; and bill help, which turns a confusing medical bill into a plain-English summary, a flag on what looks wrong, and a ready-to-send appeal. The app is our pre-sale and post-sale surface: it earns a place on the phone before someone buys a plan, and keeps earning it afterward, whatever coverage they carry.

Bill help — understand and fight any medical bill

Snap a photo of any medical or insurance bill (multi-page) and get a structured, plain-English breakdown, a flag on charges that look wrong, and generated appeal text with a downloadable document package. It takes someone from “I got a confusing bill” to “here is what it says, what might be wrong, and what I can do next.”

  • Works on any bill, independent of carrier or plan type — a universal hook, since everyone with insurance eventually gets a bill they can’t read.
  • Backed by Socrates, our medical-billing and insurance-dispute agent (EOB decoding, appeal drafting).
  • Upload by camera or photo library; live processing status; needs-more-info, no-issue, or appeal outcomes.

Dorothy — an AI advisor for your coverage

Dorothy answers health-insurance questions in chat or by voice, reasoning from what the app knows about the member’s own plan (with explicit consent) rather than as a generic FAQ bot. She is built to say when something is unknown instead of guessing.

  • Draws on the member’s saved coverage, benefits, uploaded bills, doctors, and medications.
  • Chat history, suggested follow-ups, structured answer cards, and a hands-free voice mode.
  • Works across employer, ACA, Medicaid, and Medicare coverage.

Everything else the app does

My Plan — a real coverage hub

Shows the member’s actual benefits, not just stored documents, separating medical from drug coverage. Supports employer, ACA/Marketplace, Medicaid, Medicare Advantage, Medicare Supplement, and Part D — with IDs, eligibility, deductible / out-of-pocket, and cost-share rows.

Insurance-card scan + verification

Scan a card during setup (after an explicit AI-consent step); OCR prefills carrier, plan, member ID, and group. The member confirms every field, and the app previews what it believes is true before saving.

My Care — doctors & medications

Members save their doctors and medications; the app shows plan-aware network and cost status when the data exists, and reuses it across Dorothy and coverage checks.

Calendar, deadlines & reminders

Appointments, to-dos, payments, renewals, and enrollment windows in one place, with proactive reminders and any plan-specific dates surfaced automatically.

Plan tools when you need them

For members shopping or on Medicare: plan search and compare, doctor / pharmacy / hospital lookup with CMS quality data, drug-cost estimates, coverage lookup, and enrollment guidance — the fragmented tasks people usually juggle across separate sites, bundled into one.

Advisor, support & privacy controls

A licensed human advisor a tap away, support handoff, and member-controlled privacy: AI-consent management and revoke, biometric login, profile editing, and account deletion.

What it is — and isn’t.
  • Many features depend on available source data (carrier eligibility, plan-benefit rows, ZIP, RxCUI, NPI).
  • Card scan is a prefill and verification aid, not a guarantee that every benefit is known.
  • Bill help explains a bill and possible next steps, not final legal or coverage advice.
  • Voice requires a native build; it is not available in lightweight preview environments.

Capabilities reflect the current app build; availability of any specific answer depends on the underlying plan data. Decision support, not legal or coverage advice.

Competitive Landscape

What we have vs. the market

A diligence-grade benchmark of the Medicare distribution market, organized into four categories — Medicare platforms (private brokerages, marketplaces & carrier-direct), the public resource (Medicare.gov), health applications, and B2B solutions. Filter, sort, and open any row to check a claim yourself.

Head-to-head: TPP vs. any competitor

Pick any platform for a capability-by-capability comparison of where we lead and where the competitor does.

The private / commercial Medicare-distribution market — brokerages and digital marketplaces, plus lead-gen sites, carrier-direct portals, and research tools shown for completeness. TPP is pinned at the top; filter or sort to compare, and click any row for detail.

How the market scores

Distribution of the 59 private platforms by self-serve capability score (0–7). Only we reach 7. Score measures consumer self-serve capability, not company scale — carriers and B2B tools score low here by design (e.g., they don’t publish an open algorithm).
Yes ~ Partial No ? Unknown · Click a row for detail · Score = self-serve capabilities present (max 7) · Click a column to sort

Source: TPP competitive analysis — 59 private platforms benchmarked (May 6, 2026), ZIP-verified where noted. Capability flags reflect public site behavior as of the May 2026 review.

TPP vs. SmartConnect (employer channel)

Our employer tool competes most directly with SmartConnect (the B2B division of Spring Venture Group) — the "transition your 65+ employees to Medicare" service white-labeled by Mercer. The contrast is structural.

TPP employer tool

ModelSelf-serve digital plan comparison; algorithm-driven, no phone call required.
TechnologyProprietary 8,083-plan PBP database with plan-level drug, provider, and cost modeling; open-source recommendation engine.
Carrier breadthFull Medicare market.
AlignmentThe algorithm earns no commission. If the employer's group plan is the better deal, it says so.
ThroughputSelf-serve scales without adding agents.

SmartConnect / Spring Venture Group

ModelPhone concierge — every interaction requires a licensed agent call.
TechnologyNo proprietary technology — WordPress, Calendly, BrandMuscle, Salesforce; a quiz routing to MA vs. Medigap.
Carrier breadth9 carrier organizations / 3,299 products (their own legal disclaimer).
AlignmentStructural conflict: agents earn $0 if an employee stays on group coverage, ~$600+ on Medicare enrollment.
Throughput~14 dedicated agents for 2,900+ partner organizations; transition rates 0.08–0.13% of the workforce.
Where SmartConnect is ahead (acknowledged).
  • Mercer distribution into Fortune 500 HR — the single biggest factor in their enterprise sales.
  • 2,900+ partner logos and named references (Adidas, Xerox, Barnes & Noble, TD SYNNEX).
  • 5+ years in market, licensed in all 50 states, agents who enroll on the spot.
Our counter-positioning.

"Our algorithm doesn't earn a commission. If your group plan is the better deal, we'll tell you — SmartConnect can't, because their agents earn $0 when an employee stays on your plan and ~$600+ when they enroll in Medicare." A self-serve employer savings projection is a tool SmartConnect structurally cannot offer.

Source: "SmartConnect / Spring Venture Group — Competitive Intelligence Brief," prepared for TPP, June 2, 2026, from public sources (SEC, BBB, Glassdoor, SmartConnect/Mercer/ParetoHealth collateral). Figures are SmartConnect's own disclosures or the brief's estimates.

Statistics

The numbers behind the thesis

We make three claims. A digital enrollment funnel with call-center unit economics. A testing engine that compounds those economics every cycle. And a funnel that turns every interaction into proprietary preference data. This page is the evidence, with proven figures and modeled targets kept clearly apart.

$550
Digital cost / enrollment
Fully online in 2025 AEP, versus over $2,000 for the category's prior digital attempts.
1.6×
LTV-to-CAC
Profitable, versus 0.86× for the largest public digital broker.*
150%+
Conversion lift
Click-to-enrollment, gained across a single test cycle on under $30K of media.
79%
Chose self-service
Of leads in a live preference test chose digital self-service over speaking with an agent.
The market

Coverage gaps in Original Medicare push 75% of consumers into private-market plans, where the recurring commission revenue lives. The private segments are where we earn.

Parts A & B · Government
Original Medicare
32M
enrollees
Large gaps: no drug coverage, 20% coinsurance on every visit, and no out-of-pocket cap.
No private revenue
Part C · Private
Medicare Advantage
34M
enrollees
All-in-one private plans, often $0 premium with dental, vision, and drug coverage built in.
$425 / yr · 2-yr tenure
Medigap + Part D · Private
Medicare Supplement
12M
enrollees
Covers close to 100% of costs with access to any doctor who takes Medicare. Longest tenure of the three.
$500 / yr · 6-yr tenure
4.5M
age into Medicare every year
10M
switched plans in 2024
01 · Unit economics

A digital funnel with call-center economics

Profitable, fully digital Medicare enrollment is something the category has chased for years without success. Prior digital-only attempts ran north of $2,000 per enrollment and never scaled. In live 2025 AEP testing, we enrolled members entirely online at a $550 CPA, on par with the telephonic acquisition costs of public brokers, and without a year-round agent force to carry off-season.

Player Model Cost / enrollment LTV LTV : CAC
The Pocket Protector Digital-first $550 $893* 1.6×
Legacy digital-only attempts Marketplace / self-serve >$2,000 $893* 0.45×
eHealth (EHTH) Telesales + marketplace $1,087 $934 0.86×
GoHealth (GOCO) Marketplace + agents $501 /sub N/D N/D
$893 expected LTV* Product CMS-filed in 40+ states 10+ carrier contracts 111 enrollments in 2025 AEP, 52 fully digital
$550 is a realized cost from live enrollments, not a forecast. The category's prior digital attempts never broke below roughly $2,000, and the public telephonic brokers we match spend $501 to $587 per acquisition while carrying far heavier fixed-cost agent forces.
02 · Learning velocity

Economics that compound with every test

The edge is not any single cohort; it is the rate of improvement across cycles. In one 2025 AEP, the team shipped five funnel versions on under $30K of media, more than doubled click-to-enrollment, and cut CPA by roughly $300. The same instrumentation produced a step-by-step, funnel-level path to a $300 CPA.

5
Funnel versions tested in-market on under $30K of media.
0.04 → 0.12%
Click-to-enrollment, a 150%+ relative lift within the cycle.
~$300
CPA reduction in a single AEP, from early variance down toward ~$550.

Where the cost curve is headed

Cost per enrollment, realized then modeled.
Early-cyclePeak variance, 2025 AEP
~$800
Proven2025 AEP, in-market
$550
Modeled targetFrom observed funnel gains
$300
$550 is a realized result. $300 is modeled from observed funnel-level conversion gains across click-to-result, doctor and drug lookup, and application submit. It is a target, not yet achieved.
03 · Data moat

What the data told us about our buyer

We ran a live test to understand consumer preferences and confirm our market fit, giving people the choice of how they wanted to interact with us: research and decide on their own through our tools, or speak with an advisor. Their choices confirmed the target buyer: new-to-Medicare consumers who prefer to enroll digitally rather than through an agent, and who want to research before they commit. We captured all of it at $2.90 per lead across 271 contacts.

Our buyer is new to Medicare and prefers to self-serve
72% of leads were new to Medicare, the exact segment we are built for. And 79% chose to use our tools themselves rather than speak with an agent. This is a self-service-first audience by choice.
72% new to Medicare
79% chose self-service
They come to learn, and they tell us which tools they need
Given the choice, new-to-Medicare leads gravitated to education-first tools. The enrollment-deadline tool led, followed by the plan-fit quiz and the employer-coverage comparison. In effect, the consumer is telling us which tools to build next.
52% enrollment deadline
20% plan-fit quiz · 18% employer compare
The few who want an advisor convert at a high rate
Only 21% chose the advisor path, but they were exceptional leads. 7 booked a call and 2 became new-to-Medicare members. A new-to-Medicare decision rarely closes in one session. The funnel does the education up front, so the advisor inherits a prepared, high-intent buyer.
21% advisor path
7 calls booked · 2 NTM sales

"One of the best leads I have ever experienced in all my years selling Medicare. Zero bait and switch. I called and the consumer was prepared with their Medicare card and ready to discuss their plan options with me."

TPP Licensed Medicare Advisor

And every session adds to a first-party data asset

Because consumers enter their actual doctors and prescriptions, every session builds a structured profile that makes our recommendation engine smarter and our digital enrollment more accurate. Two examples of what that data reveals.

The health profile we can see

Inferred from the medications enrollees entered during the funnel.
  • Cardiovascular (blood pressure, cholesterol, heart)27%
  • Diabetes & metabolic conditions24%
  • Pain & musculoskeletal (arthritis, joint, nerve)19%
  • Gastrointestinal (acid reflux, ulcers)14%
Why it matters: this makes the recommendation engine smarter. When a consumer's medications point to a qualifying chronic condition, like the cardiovascular and diabetes profiles above, our tools can automatically flag eligibility for a Chronic Condition Special Needs Plan (C-SNP) and surface the right options, guiding more consumers to the correct plan and a completed digital enrollment.

The asset it all feeds

A proprietary dataset that gets richer with every user.
  • Medicare data points17M+
  • Federal data sources16
  • Free consumer tools feeding signal21
  • Doctor & drug friction, mapped screen by screenroadmap
Why it matters: every interaction is structured, first-party signal that directs the product roadmap and sharpens the recommendation engine. Legacy call centers never capture this in usable form.
CPL is not CPA. The $2.90 cost-per-lead above measures top-of-funnel preference capture and demand validation. It is distinct from the $550 cost per completed enrollment in section 01. It reflects two distinct funnels measured separately.
Sources & methodology

How to read these numbers

Enrollment & funnel figures. Based on actual ad funnel statistics from AEP 2025. Reflects digital-only cost per completed enrollment.

Preference figures. From a live consumer-preference test run May 11 to June 29, 2026 (n=271). An initial live test, not a forecast.

Market sizing. CMS enrollment data and our investor materials.

Competitor figures. Public filings (EHTH, GOCO, SLQT) and Crunchbase. GoHealth's $501 is a stated cost-per-submission; LTV not disclosed (N/D).

* Expected LTV (~$893) is benchmarked to a public-brokerage three-year average. Our own realized retention data is still maturing, and LTV:CAC ratios use this expected LTV. "$300 CPA" and other forward figures are modeled targets. "$550 CPA" is a realized, in-market result.

Roadmap

Where the engine goes next

Our core engine — a proprietary data layer, a compliant AI advisor, and a comparison model that competes on the honest answer instead of a commission — was built for Medicare, but its components are domain-agnostic: the same data layer already holds 22,059 ACA plans and 2.2M rate records, and the document-ingestion and recommendation engines carry straight over. We reuse that engine in two markets next door — the forced, time-pressured decision when someone leaves a job, and the small-group employer channel.

Sep 1, 2026
COBRA Killer
2027
Dorothy Goes to Market — Small Group

COBRA Killer

The COBRA-vs-Marketplace decision tool — the wedge into the under-65 ACA market

What it is. Upload your COBRA election paperwork and we tell you — for your specific situation — whether keeping COBRA or moving to an ACA Marketplace plan is the better deal.

The strategy. Leaving a job is one of the few moments a consumer is forced into a high-stakes coverage decision on a 60-day clock, and losing job-based coverage opens a Special Enrollment Period on the Marketplace. COBRA can charge up to 102% of the plan’s total cost — the full premium the employer was quietly absorbing, plus a 2% fee — so the price jumps to a number most people have never seen. Whether COBRA or an often-subsidized Marketplace plan wins turns on income, subsidy eligibility, the deductible already met, and network — the same case-by-case comparison our engine already makes for Medicare. COBRA Killer captures the consumer at that forced decision and monetizes like the rest of our business: as the licensed agent of record on the plan the member enrolls in.

The market. Roughly 2.7 million workers lose access to employer-sponsored coverage every month — on the order of tens of millions of COBRA-eligible decisions a year, a flow that recurs through 2027. Most are made with no neutral tool, and COBRA is expensive enough that it is frequently the wrong default — the exact gap this fills.

Leans on: the 22,059 ACA plans and 2.2M rate records already in our data layer, plus the AI document-ingestion and recommendation engine built for Medicare.

Market figure: Economic Policy Institute analysis of U.S. Bureau of Labor Statistics Job Openings & Labor Turnover (JOLTS) data, 2015–2019 baseline (epi.org; bls.gov/jlt).

Dorothy Goes to Market — Small Group Strategy

A data-targeted small-group play, run by Dorothy

What it is. Our AI advisor, Dorothy, deployed as an automated quote collector and year-round benefits concierge for small-group employers (under 100 employees), sold as a service to HR teams.

The data edge. By 2027 we expect to hold the strongest dataset on group and employer plans anywhere — built the same way as the Medicare provider-network moat that already sets us apart. That changes how we go to market: instead of pitching every employer, we surgically target the specific groups whose current plans our data tells us are beatable, and arrive already knowing where the better, lower-cost option is.

The strategy. Small-group benefits is broker-mediated, slow, and under-served — most HR generalists hear from their broker once a year. Dorothy automates the quote-gathering and stays on all year, within our existing licensed-producer footprint, earning broker-of-record commissions on the coverage placed, with smart routing across fully-insured, level-funded, and ICHRA options. It extends the same “do the work for you, without the sales toll” model into a large adjacent commercial market.

Leans on: the Dorothy AI advisor, the employer-plan comparison tool, and our public-sourced employer/group plan data — the dataset we expect to be the most comprehensive in the market by 2027.

Forward-looking statements — planned releases and target dates as of June 2026, subject to change.

Business Model

How we make money

One proven engine today — carrier commissions — plus three adjacent expansion streams that resell the same tools, data, and consumer app we have already built. Each stream is labeled by stage so pipeline is never mistaken for booked revenue.

1 · Carrier commissions

We are a licensed brokerage: when a member enrolls, the carrier pays a CMS-governed commission. This is our only realized revenue today and the base the other three streams build on. Book lifetime value (LTV) per member, by product:

~$1,000

Medicare Advantage (MA / MAPD) — book LTV per member.1

~$1,000

Medicare Supplement (Medigap) — book LTV per member.2

~$100

Part D (PDP) — book LTV per member.3

1 MA can be $0 when a plan, captive/employer arrangement, or non-new-to-Medicare situation is non-commissionable. CMS CY2026 maximum: $694 first year + $347/yr renewal (renewal = 50% of initial); higher in CA/NJ ($864/$432) and CT/PA/DC ($781/$391).

2 Med Supp ranges from $0 to ~$3,000. Commissions are carrier-set (not CMS-capped) as a % of premium — roughly 20% first year, ~10% renewal years 2–6 — and pay for up to ~6 years, so a fully-commissionable plan carried to full payout reaches ~$3,000; a non-commissionable one pays $0.

3 PDP can be $0 when non-commissionable. CMS CY2026 maximum: $114 first year + $57/yr renewal.

Source: CMS CY2026 agent/broker compensation (MA & PDP national maximums); carrier Med Supp schedules. Book LTV = our estimate across our product mix.

2 · B2B platform & tool licensing

License our agent platform and tools — the provider-network “doctor” tools, the “Magic Plan” recommendation tool, and the rest of the toolset — to other companies in the space, including white-label deployments.

Hub International

In discussions to license our tools and white-label our platform.

ChenMed

Interested in licensing our doctor-network tools and the “Magic Plan” tool.

Target pricing: ~$100,000 per year per licensee, per tool licensed.

Benchmarks — the B2B Medicare-tech category

VendorWhat it isScale & ownership
SunFire / SunfireMatrixMedicare quoting + enrollment SaaS — the closest direct comp to our agent tools~1 in 4 of all Medicare enrollments transact through it; KKR + Stone Point owned
Connecture / DRXMedicare shopping, quoting & enrollment SaaS (PlanCompare, BrokerLink)~160 carriers · 6,500 plans · 120+ FMOs · 125K agents; Constellation / Harris owned
ZelisHealthcare financial-experience platform (payer-side) — scale/monetization benchmark~$17B valuation, ~$1B EBITDA (S-1 filed 2025)
Honest read for a buyer: none of these publish B2B pricing (all enterprise / negotiated), and the two direct Medicare-tool comps (SunFire, Connecture) are largely free to the agent, monetizing the carrier / FMO side. So a per-tool license is sold on differentiation and bundling, with tiered-by-org-size and per-enrollment as the natural pricing axes — the ~$100K/yr is a target, not a posted rate. Sources: company sites; Stone Point / KKR (SunFire); Constellation/Harris (Connecture); Zelis S-1 coverage, 2025–26. Hub & ChenMed status per us (in discussion, not contracted).

3 · B2B employer / group-to-Medicare

The SmartConnect / SmartMatch model — helping employers move retirees from group coverage to individual Medicare — but undercut across the board. we plan to charge ~$20–$100 per head per year for the full tools suite + consumer app.

OfferingWhat they chargePer head / year
SmartConnect (Spring Venture / SmartMatch) · Mercer SmartConnect · HPOne$0 to employer & retiree — monetized on downstream carrier commissions$0 (commission-funded)
Paid benefits-navigation / concierge~$5–$15 PEPM (per employee per month)~$60–$180
Via Benefits (WTW) — HRA administration~$2.60 / participant / month~$31
TPP — tools suite + consumer app~$1.67–$8.33 PEPM~$20–$100
Our $20–$100/head/year lands at or below the floor of paid navigation and in the same annualized band as HRA-admin fees — a genuine undercut for a bundled tools + app deliverable. The dominant transition services (SmartConnect, Mercer, HPOne) are free-to-employer and commission-funded, so the paid lane wins where an employer wants neutral, non-commissioned guidance. Sources: SmartMatch / Mercer / HPOne employer pages; Via Benefits (OPERS) ~$31/participant/yr; PEPM navigation benchmarks, 2026.

4 · Consumer app — potential paid play

The consumer app (Dorothy + bill help, plan & provider tools) is free today. It could become a charge play in the mold of consumer health-bill apps — per-action or contingency pricing on the bill-contest and appeal workflows.

GoodBill

Medical-bill negotiation. Charges 20% of the savings it wins (member keeps 80%), capped at $1,000 — pure contingency, no upfront fee or subscription.

Claimable

AI health-insurance appeals. Charges a flat $39.95 per appeal (no subscription, no success fee); many medication appeals are sponsored to $0.

Comps confirmed from each company’s site, Jun 2026. App monetization is exploratory — no consumer charge is live today.

Stage labels: Live = earning revenue today · In discussion = active prospect, not contracted · Planned / Exploratory = roadmap. Forward pricing reflects management targets, not booked revenue; current realized revenue is commissions only (see the Financials tab).

Financials

Financial position — TPP standalone

The economics of the brokerage being acquired: carrier commissions against our own operating cost, reconciled to bank and card statements through June 2026. The affiliated media and SG&A spend that flows through NaviGap is a reimbursed pass-through and is excluded here, so these figures reflect the brokerage itself.

Cash basis · reconciled to bank & card statements · unaudited. Figures tie to all seven business accounts. 2026 is a ~6-month partial year. The one-time $500K consulting fee and the affiliated media/SG&A pass-through are excluded from TPP revenue and burn. Audited statements are available in diligence.
Cash basis · reconciled · through June 2026
$67,611
Carrier commissions earned — TPP revenue
2026 YTD already ~2.5× full-year 2025
~$20,605
Net operating burn / month
after the ~$70K/mo affiliated retainer (via NaviGap)
$947,300
Capital invested in TPP
since inception · $651K external
~$413K
Affiliated media/retainer accrued
Apr–Jun 2026 · largely not yet invoiced

Carrier commissions — TPP revenue

The brokerage’s own earned revenue, growing fast
FY2025 2026 YTD (6 mo)

Monthly operating burn

The ~$70K/mo affiliated retainer offsets most of the burn
Gross burn Retainer offset Net burn

TPP P&L by year

The Pocket ProtectorOperating spendCommissionsNet spend
2023$564($564)
2024$29,424($29,424)
2025$242,701$19,388($223,313)
2026 YTD*$133,376$48,223($85,153)
Total$406,065$67,611($338,454)

*2026 is a ~6-month partial year. “Net spend” is cash burn (operating spend less commissions), not a GAAP loss. Operating spend includes $104,727 of our own brokerage media (Google + Meta), reattributed from NaviGap cards — not the reimbursed affiliated media.

Read it this way: We are an early brokerage whose commission line is ramping fast (2026 YTD is ~2.5× all of 2025 in half the time) against a cost base that, after the affiliated retainer, runs ~$20.6K/mo net.

Monthly operating run-rate

Component (monthly)Amount
US payroll (AccountantsWorld ×2)$49,280
Philippines team$11,240
Rent (Life Time Work)$3,200
Tech / software (AI, Sunfire, SaaS)$16,300
Other overhead (health, insurance, fees)$8,700
TPP own media (Google + Meta)$1,885
Gross monthly burn~$90,605
Less: affiliated retainer($70,000)
Net monthly burn~$20,605

Tech normalized to a true run-rate: AI is ~59% prepaid (annual seats + loaded credits) → ~$8K/mo economic; Sunfire is a lumpy SOW (~$4.8K/mo amortized). One-time office build-out & travel excluded. The affiliated retainer runs through NaviGap; absent it, standalone gross burn is ~$90.6K/mo.

What a buyer acquires. The figures above reflect the brokerage and its commission engine. The ~$70K/mo retainer that offsets most of the operating burn runs through NaviGap under a separable affiliated arrangement — it is not part of an acquisition of TPP and would be defined in any deal.

Capital invested in TPP

ContributorAmount
ImagineIF (J. DiToro)$381,298
NaviGap (re-contributed owner capital)$296,002
MJ Jung fund$150,000
Michael Boshardy (direct)$120,000
Total invested in TPP$947,300

Amounts are contributions into TPP; an owner’s all-entity total can differ (e.g., DiToro $401,298 total — $381,298 into TPP). External owner capital (excluding the internal NaviGap→TPP re-contribution): $651,298; total owner capital across both entities ≈ $1.11M.

Net position

Net cash invested to date — TPP$338,454
Net cash invested to date — NaviGap$302,429
Combined net out-of-pocket$640,883
Funded by owner capital (external)~$1.11M
Affiliated media/retainer accrued (Apr–Jun, mostly un-invoiced)~$413K
Credit-card balances (6/28/26)$112,567

Net out-of-pocket is after the one-time $500K consulting fee; excluding it, cumulative net spend is ~$1.14M. The ~$413K of affiliated media + consulting is accrued for Apr–Jun and largely not yet invoiced, owed by the affiliated counterparties and subject to that arrangement. Cash basis; credit-card balances assumed paid.

Methodology. Cash basis; all seven accounts (NaviGap checking, TPP checking, 2× Chase Ink, Amex Gold, Amex Platinum, Citi) reconciled to source statements. Operating spend = card charges + checking outflows (vendors, payroll, media, software, fees), net of refunds; it excludes credit-card bill payments, internal/owner transfers, and capital. The affiliated media/SG&A pass-through and the one-time $500K consulting fee are excluded from TPP revenue and burn. Prepared June 2026; audited statements available in diligence.
Licenses & Appointments

Licensing, appointments & compliance

We are a licensed, CMS-compliant health-insurance brokerage, focused on Medicare today, operating as an Illinois LLC — licensed in every U.S. state except California and New York, and appointed across leading Medicare Advantage and Medicare Supplement carriers.

Entity

  • The Pocket Protector, LLC — an Illinois LLC (formed Apr 2024), a NaviGap LLC company.
  • NaviGap LLC (Illinois) is the founding/managing member.

Licensure

  • Named license: Michael Boshardy (NPN 21126942) — our named, responsible licensed producer.
  • Licensed in every state except California and New York (48 states + D.C.).
  • Massachusetts: our entity license is pending — Michael Boshardy holds the Massachusetts license individually, so the state is covered in the interim.
  • Agency NPN 21186482. Additional licensed producers: Christopher O'Kieffe (NPN 19887558), Scott Martin (NPN 20061684).

Carrier appointments

Appointed carriers across Medicare Advantage and Medicare Supplement. Some Medicare Supplement appointments are held via bundled FMO arrangements; full roster and effective dates available in diligence.

Medicare Advantage (MA / MAPD) — 13 carriers

Aetna (Medicare) · Anthem Blue Cross and Blue Shield · Wellpoint · Healthy Blue · Simply Healthcare · Cigna Healthcare (Medicare) · Devoted Health · Humana · UnitedHealthcare (UHC) · Wellcare · Kaiser Permanente (Medicare) · Zing Health · Highmark

Medicare Supplement — 5 carriers

Aetna Supplemental · American Home Life · Cigna Supplemental Benefits · Mutual of Omaha · Medico Insurance Company

Medicare lines of authority

Medicare Supplement

Active — carriers appointed

Part D — PDP

Active

Medicare Advantage — MA / MAPD

Appointed across 13 carriers

Compliance posture

CMS / TPMO

We operate under CMS third-party-marketing-organization (TPMO) rules. The required disclaimer is shown to consumers — "The Pocket Protector is an independent consumer resource and not connected with or endorsed by the U.S. government or the federal Medicare program," and "we do not offer every plan available in your area." Our public, consumer-facing site uses no prohibited superlatives and no fabricated figures (per CMS/TPMO rules); competitive superlatives in this confidential diligence overview are buyer-facing claims, not consumer marketing.

Data & AI

HIPAA-aware operations; a Business Associate Agreement (OpenAI enterprise) for compliant AI on health/financial data; the public consumer tools are designed to store no PHI.

Licensure, NPN, and disclaimer facts from the public licensing page (thepocketprotector.com/licensing). Lines-of-authority status, carrier appointments, and the MA-pending status are internal/diligence items — confirm the carrier list and NPN of record in diligence.