How to Spend Your Money On Healthcare

Spending thousands of dollars a year on health insurance and healthcare needs a careful strategy. You wouldn’t buy a new car or a new house without doing your best to spend wisely. 

Also, having insurance doesn’t mean you have doctors when you need them. In efforts to save money, insurance companies are limiting the number of doctors available to you. And without a doctor you can easily turn to at all times who can help you figure out exactly what you need, you’ll probably overspend. Many people go to the ER because they have nowhere else to turn to. Just one unnecessary $5,000 ER visit pays for 10 years of Sherpaa’s services. Healthcare is expensive but mistakes are avoidable. Having Sherpaa helps you figure out:

  • Can you get diagnosed and treated online or do you need in-person care?
  • Can you just get a blood or imaging test and get diagnosed instead of an in-person visit?
  • Do you need a specialist, an internist, an ER, or an urgent care visit?
  • Where can I get this medication for the lowest cost?
  • Can I get a refill on a medication without the cost of an office visit?

How to get the most out of your insurance

Step 1: Get a high deductible plan

Step 2: Get a Health Savings Account

Step 3: Get Sherpaa

Step 4: Spend on in-person healthcare strategically and only when necessary

$1,130: Typical Savings Per Year as an Individual with Sherpaa


The Details

Sherpaa wants to ensure you spend as little of your deductible as possible. Our unlimited care membership covers the costs of treating 70% of typical primary and urgent care health issues, avoiding out-of-pocket spending on expensive in-person visits and tests. For the 30% of the time that you need in-person care, Sherpaa doctors organize in-network care for you helping you spend effectively. Most insurance plans make you spend thousands before insurance starts picking up the bills. Sherpaa is a smart layer that sits on top of any health insurance plan and helps you spend your money wisely.

Here’s how to do it:

Step 1: Choose a high deductible plan.

Use your employer,, or Stride.

A higher deductible means a lower monthly premium (the typical difference is ~$50 less per month for an individual).

We recommend choosing the insurance plan with lowest monthly premium. This works best for most people.

Step 2: Get an FSA or HSA account

As an individual, you can invest $3400 pre-tax dollars per year into the FSA or HSA account (What is an HSA account?) that can be spent on healthcare, including Sherpaa. This means Sherpaa’s $40 a month fees are discounted by ~20% (pre-tax money) turning that $480 a year into ~$380 for unlimited 24/7 care.

You can get these accounts through your employer or as an individual through your bank (Bank of America, Wells Fargo, UMB, etc).

You can also invest the money in your HSA account in a service like Betterment and likely earn a return on your investment. The average return on Sherpaa’s employees’ Betterment accounts was 8% for the past year.

Step 3: Join Sherpaa: Get 24/7 doctors + financial guidance

Figuring out what you need and how much to spend is almost impossible. We’re doctors who know how to look after your health and wallet.

If you switch insurance companies, you often switch your traditional PCP. Instead, use Sherpaa as your PCP and don’t ever worry about which plan you have.

Just remember

Sherpaa never bills you for anything but our monthly membership fee. It’s unlimited 24/7 care.

If any doctor, including a Sherpaa doctor, orders tests or medications before you’ve spent your deductible, you cover the costs. If you’ve spent your entire deductible, insurance picks up the costs.


Average 18-65 year old has 2.8 doctor, ER, and urgent care visits per year

Sherpaa prevents 2 out of 3 in-person visits

Working age population gets, on average, 8 prescriptions a year at an average cost of $70 a month. Sherpaa doctors prescribe medications through the app and direct you to the most cost-effective way of getting these medications.

There are two healthcare systems in America, I call them The Last 5% and The First 95%.

The Last 5%

It’s characterized by expensive daily drugs, highly specific tests, detailed imaging, super-specialized specialists, robots, massive hospital campuses, and every expensive thing but the kitchen sink. It’s the world’s best. It’s powered by specialists and big hospital buildings. And when people talk about the US healthcare system being the world’s best, it’s because of this “Last 5%” System. It’s life-changing when everything goes right. It’ll cost you an arm and a leg, but it can sometimes work miracles, if your definition of miracle is maintaining a beating heart. It’s also highly unsafe, risky, and prone to complications, hospital-acquired infections, and disconnected care. But that’s not something The Last 5% likes to think about. I call it The Last 5% because it’s solving the last 5% of human health problems. Remember, 80% of your lifetime medical costs are spent in the last 6 months of your life. It’s treating people, mostly adults, at the end of their life, after an unhealthy lifestyle from an unhealthy culture and environment has done a number on their bodies. Any problem where you’re trying to solve the last 5% of the problem is ungodly expensive and can only get more expensive.

The First 95%

It’s vaccines, clean water, short-term antibiotics, quick fixes, healthy food, exercise, education, and environments. It’s powered by neighborhood primary care doctors in small practices, farmers markets, bike paths, relationships with family and friends, and anything else that helps you get to the last 5% of your life. Health insurance companies are terrible at impacting this System for the better. But for an idea of how they could, see how the largest health insurance “company” in America has agreed to pay for removing lead in Flint. Compared to The Last 5%, there’s not a lot of money to be made here. That’s why the medical component of this sort of looks and feels like the DMV. It’s also not really connected to the Last 5% System. But it’s 95% of the solution. It helps you live a wonderful life throughout your life. And that’s what matters. That’s why all I want to do with my life is fix 95% of the problem.

Sherpaa’s Not-So-Secret Master Plan.

In August 2006, Elon Musk wrote a blog post outlining Tesla’s vision for the next 10 years, The Secret Tesla Motors Master Plan. I think it’s important for every company to articulate their long-term strategy and vision. So, with a whole bunch of self-awareness that I’m not Elon Musk, here’s Sherpaa’s not-so-secret Master Plan for the next 10 years. Keep in mind, healthcare moves glacially and the problems healthcare fought 10 years ago are essentially the same as today. With that in mind, here’s what we want to accomplish:

1/ Sherpaa will be a new specialty for young and middle-age adults that focuses on our unique issues.

2/ Sherpaa will be the cloud-based healthcare service funnel accessible anytime and anywhere. We will be the primary go-to service for accessing healthcare and solving health problems, arranging in-person care when necessary, curating and connecting patients to the right online or local healthcare service, and managing ongoing health issues.

3/ Diagnosis will be data-driven. Because 98% of everything that happens within Sherpaa’s platform is asynchronous text-based structured messaging, Sherpaa is the only place in healthcare where the entire conversation, questions asked, tests ordered, treatment plan prescribed, and outcome are meaningful, easily analyzable data points. Since the EMR we built was built to solve communication and health problems, not bill insurance companies, the data we have is extremely real-world and accurate. We will leverage this data to make diagnosis and treatment more accurate and cost-effective. Sherpaa will use a data-driven evidence-based strategy to ensure your diagnosis is efficient and consistently accurate. These diagnostic protocols will be made open-source to benefit anyone and everyone. Think “If This Then That” but for diagnosis. We do not want to focus on diagnosing long-tail diseases. Let Watson do that. We want to ensure that diagnosis for non-long-tail diseases are accurate 99.9% of the time. (Example: “If a patient answered our series of questions in the following way, and the recommended tests ordered showed these results, there’s a 99.9% chance the patient has x diagnosis.”)

4/ Treatment will be data-driven. Sherpaa will ensure all your treatment plans are custom-tailored to your unique body, genetics, and lifestyle and correlated with outcome to benefit you and the entire patient population. These treatment protocols will also be open-source.

5/ Care will be Increasingly cost-effective. Sherpaa will deliver care increasingly cost-effectively for you while also continuing to operate profitably. All virtual care should get less expensive over time with improving automation and artificial intelligence that augment our professionals’ expertise.

6/ Sherpaa will work with professionals from all the specialties that can effectively diagnose and treat virtually (dermatology, allergy, nutrition for example).

7/ Sherpaa will ensure price transparency. Every order for tests, medications, and referrals show an associated cost to you with a description of benefit and value to you and your unique situation.

8/ Sherpaa will curate and drive patients to virtual and local services that fulfill real medical/financial needs that make our patients’ lives easier throughout each step of the patient experience. 

9/ Sherpaa will deliver virtual care and coordinate in-person care in all 50 states and be insurance company and employer agnostic. Your care shouldn’t be tied to your insurance company, employer, or neighborhood. These change in our mobile world. Your care should be cloud-based, accessible anytime and anywhere, and layered on top of any insurance plan to make care more and more cost-effective for you.

If healthcare was designed around you, it’d be Sherpaa.

You graduated from your pediatrician, so you’re sitting next to a 90-year old in an internist’s office. For the past few years, your relationships with random doctors have felt more like one night stands. Healthcare’s broken and backwards. It’s had decades to fix itself, but it still looks and feels too much like the DMV. And it’s out of control expensive. Your insurance premiums are $450 a month and you have to spend $5,000 out of your own pocket before insurance even kicks in. Even worse, your doctor’s ordering tests for you left and right and you’re not even told how much they’re going to cost. There goes vacation this year. It’s completely out of your control and your bank account is at their mercy.

All of you occasionally get sick or hurt. Thirty to 40% of you have ongoing problems and you need regular doctors. Things like asthma, anxiety, migraines, allergies, depression, arthritis, high blood pressure, sex issues, family, friend, and romantic relationship issues, and job stress issues. So why isn’t there a healthcare specialty that specializes in your unique issues?

And it’d be nice to have some consistency. You change jobs, move cities, change insurance companies, travel. Every time, you’re scrambling for new doctors.

If healthcare was designed around your needs, you’d see that most things don’t need to be done in person. Healthcare is just communication and problem-solving. If office visits and procedures weren’t the only way doctors got paid, you’d quickly see that 70% of healthcare communication and problem-solving could be handled virtually. You’d do everything you possibly could within an app, before you stepped it up to the inconvenient and expensive in-person visit. And when you need to spend your money, you want to know how much it’s going to cost you.

This is the vision Sherpaa has for you. We’ve had almost 5 years of a head start working with the employees of ~150 forward-thinking companies like Blue Apron, Casper, Tumblr, and Foursquare. Here’s what we’ve accomplished so far:

  • We’ve built primary-care-in-the-cloud powered by our team of full-time doctors and our patient-facing web, iOS, and Android apps that enable you to create cases; message with our doctors; approve or deny prescriptions, labs, and referrals; view the details of referrals to specialists and facilities; and view lab results, imaging results, and reports from specialist visits.
  • We’ve built a robust technological platform for our doctors allowing them to manage an entire online population of people; message with you; ask you a series of questions about your issues unique to your situation; treat you with evidence-based treatment plans; easily share with you the profiles of local specialists, urgent care centers, radiology centers, ERs, and ambulatory care centers from the proprietary network of Sherpaa-friendly resources we’ve built over the years; e-prescribe; order lab and imaging tests; receive those results; and ensure all of these online and real-world actions are accounted for and acted upon.
  • We’re delivering online care in 37 of the most populated states.
  • We’ve created a new genre of healthcare and redesigned how doctors and patients problem solve and get things done.

It’s important to have a vision. It keeps you laser-focused. But for now, purchase a high deductible plan, sign up for Sherpaa today, use Sherpaa doctors as your primary care, and join our mission to make healthcare accessible, appropriate, and affordable.

Here’s how you get prescriptions through Sherpaa’s app. Our doctors prescribe the medication. You approve or deny it. If you approve, you choose your pharmacy. Then you pick it up! Real simple, huh? If you want to join a medical practice that makes healthcare this easy, you can at


How does Sherpaa save you money?

It depends. Are you a Healthcare Spender or not? If you’re not, you’re likely pretty healthy and part of 40% of the population that spends ~$500 or less on healthcare every year. That also means that, at any point, you can become a Spender by either getting sick or hurt. When that happens, join Sherpaa.

But 50% of people age 18-64 spend $500 to $10,000 a year on the 4 main healthcare expenses:

  1. PCP, Specialist, Urgent Care, and ER visits
  2. Tests
  3. Medications
  4. Procedures

If you’re spending this money without a strategy and without a guide who’s always thinking of your expenses, you’re going to pay more than you should and it’s likely going to be much more than the cost of a Sherpaa membership.

Sherpaa helps you spend your money wisely

The healthcare system is not set up for you to be smart with your money on your own. Sherpaa’s doctors aren’t just doctors. They’re also navigators. They’re well-versed in knowing the system, how to work it for you, how to leverage the nationwide Sherpaa-friendly network of specialists and facilities we’ve built, and how to get things done cost-effectively and efficiently. Think of Sherpaa as an online medical practice you got to first for all things healthcare. By going online first, you can work with our doctors to either be treated online (without co-pays or using your health insurance) or be strategically directed to the most appropriate and cost-effective way to get your problem solved. That’s why Sherpaa works so perfectly with most insurance plans, but especially well with high deductible plans where you have to spend the first few thousand dollars.

Doctor, Urgent Care, and ER visits

With good online and phone communication, lab and imaging tests, photos, and close follow-up, 70% of health issues are treated virtually by our doctors. This means Sherpaa avoids 70% of office, urgent care, and ER visits and the claims they generate. Also, by clearly understanding the details of the issue before you visit a doctor in-person, our doctors can determine exactly what services and which specialist you need to effectively solve your problem with as few in-person visits as possible. It’s just very efficient.


When you see a traditional doctor in-person, they order tests and effectively spend your money for you without explaining the benefits, value, and costs of the tests. MRIs and blood tests can be hundreds to thousands of dollars. We think that’s wrong. After Sherpaa doctors explain to you the value and benefits of the blood and imaging tests they order, you can approve the order in the app. You’re in control of your spend and we simply act as your expert consultants. And, again, paying cash for tests can often be far less expensive than using your insurance.


Healthcare Spenders, on average, get 8 prescriptions a year at an average cost of $70 a month. Sherpaa doctors prescribe medications through the app and direct you to the most cost-effective way of getting these medications. If it’s a medication you need that day, we can let you know you can get these medications for, say $4, at certain pharmacies. If it’s a daily medication, we can let you know how you can get this routine medication for the lowest cost by leveraging online pharmacies like Pillpack. We estimate ~20% savings in medication costs for prescriptions through Sherpaa.


Honestly, this is the hardest one. For the most part, when you need a procedure, you need a procedure. However, some specialists have a reputation for doing more procedures than others. At Sherpaa, we believe less is more. And we also know that 6% of specialists are responsible for 60% of malpractice cases. We absolutely avoid those specialists and steer you toward those who only do procedures when it’s absolutely necessary. Paying cash can also be far less expensive than using your insurance. We’ll help you figure out what’s best for your unique situation.

Doctors should charge by time, not transactions

Charging by transactions means the more doctors do, the more they get paid, and the more your wallet suffers. It also means high-speed churn, not high quality, personalized service. And if you go to the doctor, the ER, or an urgent care center, and you’re sent home, and something changes that will affect your outcome, you’ve got to make another appointment and pay for another appointment.

We think that’s unsafe, inefficient, unfair and wrong.

That’s why Sherpaa is now offering two new pricing plans to ensure everyone can access our care:

  • 30 days for $150
  • 1 year for $40 per month

30 days of Sherpaa for $150

Typical issues perfect for this plan are a sprained ankle, strep throat, a skin infection, etc.. Instead of going to the ER or an urgent care center and exposing yourself to more infections or waiting 22 days for a PCP visit, just fire up Sherpaa. It’s an accessible quick fix that helps solve problems in a modern way, but also keeps costs low. Why 30 days? Because things take time to get better. Good care is ongoing communication and check-ins to ensure things are getting better. But sometimes things get worse and you need local, in-person care coordination with specialists. Thirty days is the magic number where the vast majority of these kinds of issues get resolved.

365 Sherpaa Concierge for $40/month

This is for folks who want peace of mind that they always have a direct line to their own personal doctors no matter where they are in the world. It’s also for people who have ongoing needs on a monthly basis and the only option for them is old-fashioned, in-person, expensive office visits, urgent care visits, or trips to the ER. As always, once you’re a member, it’s:

  • Unlimited 24/7 access to your Sherpaa physicians while home or traveling
  • Expedited appointments and care coordination with local, hand-picked specialists
  • Personalized recommended preventive tests ordered and interpreted
  • Personal curation of products and services that maximize your health and lifestyle