From this WSJ article:

  • A guy buys a catastrophic health plan that pays up to a fixed amount for doctor and hospital bills based upon the diagnosis
  • He needs a hernia repair
  • He tries to use his insurance and they try to make him pay $20,000 up front for the procedure
  • He cancels the procedure and goes back to his doctor to regroup

And here’s the solution he and his doctor discovered:

Most people are unaware that if they don’t use insurance, they can negotiate upfront cash prices with hospitals and providers substantially below the “list” price. Doctors are happy to do this. We get paid promptly, without paying office staff to wade through the insurance-payment morass.

So we canceled the surgery and started the scheduling process all over again, this time classifying my patient as a “self-pay” (or uninsured) patient. I quoted him a reasonable upfront cash price, as did the anesthesiologist. We contacted a different hospital and they quoted him a reasonable upfront cash price for the outpatient surgical/nursing services. He underwent his operation the very next day, with a total bill of just a little over $3,000, including doctor and hospital fees. He ended up saving $17,000 by not using insurance.

This is exactly the kind of thing we do here at Sherpaa. Healthcare is so damn confusing and so stupid expensive. There are so many tricks and loopholes that the average person can’t understand nor be expected to know. Come to us first, and we, through our insider experience and knowledge of these tricks, will craft a plan that can save you the cost of my awesome 2010 Mini Cooper. 

This also works wonders for not only individuals like this gentleman, but also for self-insured companies.

On Saturday night, I had the pleasure of going to the Music Hall of Williamsburg to see one of my favorite people in all the world, Rick Webb, get married to the lovely Emma Welles (now Webb). They rented out one of the best music venues in the city, transformed it into a wedding stage complete with multiple bars, La Esquina tacos, cupcakes to meet all dietary requirements, pizza, and a space photobooth. For 9 hours, there were many DJs, and 5 bands. One of the bands was Rick’s old band (Rockets Burst from the Streetlamps), reunited (after 12 years!) to celebrate the occasion. Rick nailed it and I finally found this song buried on the internet and I can’t stop listening to it.

I think the vast majority of people who attended would all agree it was by far the best wedding ever created. 

It’s really inspiring to witness a relationship come together that’s truly magical— one where the two are even better together, than apart. It’s pretty much what we all want and hope for in our lives. As everyone knows, relationships aren’t easy. But for those who make it look easy, I salute you. Thank you Rick and Emma.

“After you’ve done a job for six or eight years,” Mr. Bloomberg said, “you know what can’t be done.”

— in response to “Are you keeping any of Giuliani’s team?” when Bloomberg was first taking office.

What an amazing response. A lesson for me— never stop dreaming. Never get frustrated or pessimistic. Always believe that the world is a getting better and will always get better. Hire dreamers, inspirers, and persistent doers who can get things done…relentlessly. 


“Your life is going to be a gradual process of becoming kinder and more loving: Hurry up. Speed it along. Start right now. There’s a confusion in each of us, a sickness, really: selfishness. But there’s also a cure. So be a good and proactive and even somewhat desperate patient on your own behalf – seek out the most efficacious anti-selfishness medicines, energetically, for the rest of your life.

Do all the other things, the ambitious things – travel, get rich, get famous, innovate, lead, fall in love, make and lose fortunes, swim naked in wild jungle rivers (after first having it tested for monkey poop) – but as you do, to the extent that you can, err in the direction of kindness. Do those things that incline you toward the big questions, and avoid the things that would reduce you and make you trivial. That luminous part of you that exists beyond personality – your soul, if you will – is as bright and shining as any that has ever been. Bright as Shakespeare’s, bright as Gandhi’s, bright as Mother Theresa’s. Clear away everything that keeps you separate from this secret luminous place. Believe it exists, come to know it better, nurture it, share its fruits tirelessly.”

Sometimes Sherpaa amazes me.

I’m in San Francisco for the week after having spent the weekend with Tim O’Reilly and folks at Foocamp. And I’m speaking at a Rock Health conference here on Friday, so I decided to save the environment and just stay and work here for the week. So I just checked in with my team and asked them for an update. Cheryl said it was a great day. 

As you may or may not know, my company, Sherpaa, procures the right health insurance for your company and makes healthcare accessible via our 24/7 concierge doctors. Fewer claims means fewer costs.

So we procured insurance today for two companies, both around 15 employees who were currently purchasing health insurance through either a broker or a PEO. They heard about us and were looking for something better. Cheryl said, for both, we saved them over $100,000 each. And that’s just by procuring the kind of insurance that makes most sense for their employees. Importantly, we never recommend a plan that’s a downgrade from their current offering. That’s our rule.

It’s almost funny money. Healthcare is just full of so much confusion, and that confusion leads to waste. And that waste is what our current system thrives on.

So, if you want a better system, put your money into something that’s fixing the problem, rather than blindly spending wasteful dollars on the same old nonsense.

Another new stat we ran last Friday. When people reach out to our doctors because they’re sick, they’re hurt, they need a refill, or have a mental health concern, we solve that problem 65% of the time without referring into the confusing healthcare system. That means 65% of visits don’t actually need to happen. That means 65% of a company’s claims, when they are clients of Sherpaa, never happen. Fewer claims means lower costs for both employers and employees.

And that’s why all of our clients have renewed with us for year 2 and we’re seeing that those premium increases are less than half of the average premium increase for companies.

We’re changing how healthcare is delivered, how much it costs, and how it’s paid for.

And that’s why I absolutely love what I do.


“the tree was happy,” giving tree inspired lettering. my friend jay commissioned me to do this piece for a friend of his who had just given birth to a baby boy. the lettering style is based on the illustration of the tree from Shel Silverstein’s classic children’s book. congrats mom and dad and thanks jay for the opportunity to create this work!

The co-founder of my company, Cheryl, had a lovely little boy a few months back. I’m not the kind of person to just give a gift you can get anywhere. I like to make my gifts special and unique to that person. So I commissioned Dailey, one of my favorite designers, to create something Cheryl and her husband would enjoy, inspired by the most influential book to both Cheryl and me. So the entire Sherpaa team commissioned Dailey to make this piece. We framed it and it’s just gorgeous.