Reading Lists

After taking a step back from a full-time operating role in health tech, I’m spending some time diving deep into the history of some of the most successful businesses that have operated in some of the most impactful industries in the US, as well as deepening my understanding of healthcare, and specifically the economics of healthcare. I’ve come up with a reading list that I’m going to work through over the coming weeks — 10 books on business history and 10 books on the economics of healthcare. Sharing it here. Feel free to send any recommendations!

Business History

Private Empire: ExxonMobil and American Power by Steve Coll

The Box: How the Shipping Container Made the World Smaller and the World Economy Bigger by Marc Levinson

Tough Calls: AT&T and the Hard Lessons Learned from the Telecom Wars by Dick Martin

Citizen Coke: The Making of Coca-Cola Capitalism by Bartow J. Elmore

Capitalism in America: A History by Alan Greenspan and Adrian Wooldridge

Disney War by James B. Stewart

The Fish That Ate the Whale: The Life and Times of America’s Banana King by Rich Cohen

Factory Man: How One Furniture Maker Battled Offshoring, Stayed Local – and Helped Save an American Town by Beth Macy

Empire of Cotton: A Global History by Sven Beckert

Brick by Brick: How LEGO Rewrote the Rules of Innovation and Conquered the Global Toy Industry by David C. Robertson

Business of Healthcare 

Pricing Life: Why It's Time for Health Care Rationing by Peter A. Ubel

Catastrophic Care: Why Everything We Think We Know about Health Care Is Wrong by David Goldhill

Moneyball Medicine: Thriving in the New Data-Driven Healthcare Market by Harry Glorikian and Malorye Allison Branca

Redefining Health Care: Creating Value-Based Competition on Results by Michael E. Porter and Elizabeth Olmsted Teisberg

An American Sickness: How Healthcare Became Big Business and How You Can Take It Back by Elisabeth Rosenthal

The Innovator's Prescription: A Disruptive Solution for Health Care by Clayton M. Christensen, Jerome H. Grossman, and Jason Hwang

The Creative Destruction of Medicine: How the Digital Revolution Will Create Better Health Care by Eric Topol

Medicare Meltdown: How Wall Street and Washington are Ruining Medicare and How to Fix It by Rosemary Gibson and Janardan Prasad Singh

Overtreated: Why Too Much Medicine Is Making Us Sicker and Poorer by Shannon Brownlee

The Price We Pay: What Broke American Health Care—and How to Fix It by Marty Makary

Healthcare's Incentive Misalignment

Just under 15 years ago, I sat down in a conference room with one of my clients, the SVP of Benefits of a self-insured, Fortune 100 company. Like most large companies (his had about 300,000+ employees at the time), they were focused on reducing their health insurance costs as it had become an enormous line item for them that had the attention of their CEO. My company recently launched a product that helped large employers drive enrollment and engagement in voluntary benefit programs (things like smoking cessation, health risk assessments, fitness contests, nutrition counseling, etc.). Like many companies, my client had very low usage of these programs. I spent a few minutes telling him about our product, thinking that if we could increase usage of these programs, his employees would be healthier, bringing down their insurance costs.

Once I was done talking, he looked at me and told me the thing that large self-insured employers and health plans aren't supposed to say:

"Brian, the average employee's tenure at our company is 22 months. I don't want to spend time investing in driving usage in things that will make my employees healthy only to have them leave and have some other employer benefit from that investment."

And in those two sentences, he articulated the #1 structural problem with healthcare in the United States: incentive misalignment.

Misaligned Incentives

There are three major players in US healthcare: the patient, the provider, and the payer. And none of their incentives are aligned.

Patient: The patient's incentive is to live a long, healthy life.

Provider: The provider's incentive is to have lots of sick patients who need billable treatments.

Payer: The payer's incentive (or self-insured employer) is to cover lots of healthy patients who don’t get sick and don’t need treatment. But only for a short period. They only care if the patient is healthy while they're a member of their health plan. Members typically stick with the same plan for 2 to 3 years. Health plans have extremely high churn rates as employees change jobs, patients fall on and off Medicaid, move to lower-cost Medicare plans, etc. Payers don’t have a financial incentive to invest in the long-term health of the patient. They have no incentive to help the patient live a long, healthy life. In fact, they have a disincentive to invest in the long-term health of the patient if that payoff comes after the patient is no longer a member. This dynamic applies to the provider as well in a value-based care model where the provider is taking financial risk. 

To be clear, when I’m talking about incentives, I’m not talking about ethical incentives. Everyone wants people to be healthy. I’m talking about financial incentives. They are not aligned. And that’s a real problem, as payers and providers are businesses that need to make responsible financial decisions. 

For business models and systems to work well, they need incentive alignment. Take the iPhone ecosystem as a simple example. The user wants a great phone at a reasonable price with an unlimited number of functions. Apple wants to sell a lot of high-margin phones and high-margin apps. And the app makers want a huge audience to build apps for. It’s not perfect, but financial incentives are generally aligned, so this ecosystem thrives.

In a system full of problems, this lack of aligned incentives is the core problem in healthcare.

We need to get to a system where the entity caring for the patient and the entity paying for the care of the patient is financially aligned with the patient’s incentive to live a long, healthy life.

Solutions

Ideally, the government could help with some top-down structural changes such as incentivizing longer-term health investments through tax incentives, allowing plans to benefit from long-term preventative investments, or possibly universal coverage of some sort and changing the way care is paid for. However, a big change from the government will be difficult and come with its own complex set of sensitive tradeoffs. That said, It seems the use of HSAs, which allow employees to carry tax-free dollars that can be used for health expenses across employers, has expanded. I’m also very encouraged by the Individual Coverage Health Reimbursement Arrangement (ICHRA) that was launched in 2019, set up through a partnership between HHS, the Department of Labor, and the Department of Treasury, which allows employees to pick their plan outside of their employer and get reimbursed by their employer, allowing them to stick with the same plan as they change jobs. We need more of that. 

The private sector has a huge opportunity to address the incentive problem through real business model disruption. The word “disruption” gets thrown around a lot, especially in health tech. But disruption doesn’t just happen through new technologies. It happens through fundamental business model transformation that changes the way business is done. The hotel industry wasn’t disrupted by the Internet or even by early Internet companies like Orbitz, Expedia, and Kayak. Those services just changed the way consumers book hotels and the way hotels do marketing. AirBnB was actually disruptive by transforming a gigantic B2C business into a peer-to-peer business. That’s disruption.

Of course, these business model transformations take time, and they almost always start by focusing on a very niche part of the market and scaling up from there. We’re seeing some signs of this in healthcare:

Longevity-focused solutions such as Function Health and Neko Health give the patient more control and take a longer-term, consumer-focused focus perspective on health. 

Direct primary care models like Taro Health, where patients pay a flat fee for access to primary care services incentivizing providers to focus on preventative care for the long term.

In 2013, I wrote a post titled 15 Reasons Why Healthcare Has A Business Model Problem. Rereading it today, all of those problems still stand. Healthcare is a uniquely challenging problem for all of the reasons I listed in that post. And one thing I’ve learned over the years is that you can complain about it all you want, but when you have to turn your attention to solutions, you realize there simply are not great answers. It’s just a set of very complex, nuanced, and thorny tradeoffs.

As Charlie Munger said, “Show me the incentive, and I’ll show you the outcome.” The negative outcomes have been evident for years. While many of these approaches are early, and it’ll take time to get real traction, it’s exciting to see entrepreneurs focused on root cause incentive alignment to drive long-term and sustainable transformation. We need it now more than ever.

DOGE, Startups & Political Party Paradoxes

Elon Musk and Vivek Ramaswamy outlined the rationale behind their Department of Government Efficiency project (DOGE) in the Wall Street Journal last week. DOGE is intended to serve as an advisory board to streamline the U.S. federal government and reduce inefficiencies, particularly within three-letter agencies like HHS, EPA, FTC, DOD, etc. While the idea is controversial, it’s also hard not to like. No doubt government isn’t as efficient as it could be, and with the exploding federal deficit, cost reduction sounds like a nice idea. However, it’s worth noting that several presidents have tried similar initiatives in the past with limited success.

What makes this particular effort interesting, though, is its focus on reducing the thousands of regulations federal agencies have implemented over the years. The idea is that fewer regulations would mean reduced headcount to enforce those regulations and taxpayer savings. Many Americans may not realize that unelected federal agency staff write thousands of rules annually governing how businesses across the country operate.

These rules, while rooted in laws passed by Congress, are written and enforced by the agencies themselves. For example, Congress might pass a law like the Safe Drinking Water Act, and the EPA would then draft and enforce specific rules regarding contaminants, pollutant limits, and reporting requirements. This structure makes sense because Congress doesn’t have the bandwidth to dive into the details of implementing every law.

Critics argue that these agencies have amassed too much power, often acting on their own priorities rather than staying accountable to the public.

Musk and Ramaswamy wrote in their piece:

“Our nation was founded on the basic idea that the people we elect run the government. That isn’t how America functions today. Most legal edicts aren’t laws enacted by Congress but “rules and regulations” promulgated by unelected bureaucrats—tens of thousands of them each year. Most government enforcement decisions and discretionary expenditures aren’t made by the democratically elected president or even his political appointees but by millions of unelected, unappointed civil servants within government agencies who view themselves as immune from firing thanks to civil-service protections.

This is antidemocratic and antithetical to the Founders’ vision. It imposes massive direct and indirect costs on taxpayers. Thankfully, we have a historic opportunity to solve the problem.”

Government agencies, like most organizations, grow in size and scope over time. It’s human nature to want to do more with more influence, more budget, and more people. Rarely do people within these organizations prioritize limiting their scope or shrinking their footprint. It’s just not in our nature.

As a result, millions of pages of regulations now govern nearly every aspect of American business. While many of these rules are undoubtedly necessary, it’s reasonable to assume there’s significant overreach.

All of this reminds me of a talk Bill Gurley gave a while back on regulatory capture. Regulatory capture occurs when agencies tasked with regulating an industry become overly influenced by the interests of the organizations they regulate.

Gurley talked about a classic example of this in healthcare. Epic Systems, the healthcare software giant, benefited enormously from the Affordable Care Act (ACA). The ACA’s HITECH Act incentivized healthcare providers to adopt electronic medical records (EMR) software. A new agency, the Office of the National Coordinator for Health Information Technology (ONC), now renamed to the Assistant Secretary for Technology Policy and Office of the National Coordinator for Health Information Technology (ASTP/ONC), was established to administer this program.

ONC mandated payments of $44,000 per doctor to purchase EMR software and an additional $17,000 for demonstrating "Meaningful Use" — proof they were actively using it. Epic’s CEO played a pivotal role in designing the requirements for Meaningful Use, which aligned closely with Epic’s existing products. This created high barriers to entry, forcing smaller competitors out of the market or to incur major penalties for being out of compliance with the new regulations.

ONC has gone on to write more and more rules on top of the EHR standards for things like health IT certification, interoperability standards, and information blocking. If you work at a health tech startup, it’s more likely than not that these rules impact your company in some way.

Perhaps the best examples of regulatory capture came out of the Great Financial Crisis in 2008. Financial regulations, like Dodd-Frank, reinforced the dominance of the large incumbent banks. These rules imposed strict capital and compliance requirements, which big banks could absorb but smaller ones could not.

The result was that large institutions like JPMorgan Chase and Goldman Sachs emerged stronger than ever, making it difficult for smaller banks and new entrants to thrive.

Again, while many of these rules are valuable, many are not. And the overarching structure of the system generally favors large incumbents. This is true for two reasons:

1/ Lobbying Power: Large companies have the resources to influence Congress and federal agencies through lobbying and campaign donations. Many of them house large government affairs and public policy staffs in Washington.

2/ Established precedents: Policymakers often are reluctant to implement big changes to the way businesses operate and as a result design their programs and rules around the existing establishments.

If DOGE succeeds in reducing federal agency regulations, it would inherently challenge rules designed to protect the country’s largest companies that have benefited from the regulatory capture dynamic — ExxonMobil, Microsoft, Boeing, UnitedHealth, Walmart, etc. 

This is a rather surprising effort to come out of a Republican administration that has typically supported big business, but it makes sense in the context of some of Trump’s other non-traditional decisions since winning the election. Take some of the comments he made when nominating RFK for Secretary of HHS:

“For too long, Americans have been crushed by the industrial food complex and drug companies who have engaged in deception, misinformation, and disinformation. HHS will play a big role in helping ensure that everybody will be protected from harmful chemicals, pollutants, pesticides, pharmaceutical products, and food additives.”

This statement sounds more like left-wing activism than traditional Republican rhetoric.

Back to the DOGE effort. No doubt the purpose of this effort is to reduce the cost of the federal government, but by unraveling many of the regulations that protect incumbents, this also starts to shift the balance of power back towards startups. Multiple VCs have talked about how these regulations have paralyzed the work of many startups, particularly in fintech, crypto, and AI. While Musk and Ramaswamy have run big businesses that have undoubtedly benefited from these regulations, they’re both founders and entrepreneurs as opposed to traditional, big company managers. Much of this effort feels like an indirect backlash against the “managerial revolution” where professional managers hold the primary power in organizations and economies as opposed to inventors, entrepreneurs, and founders. So, in some ways, DOGE isn’t just an effort to reduce the size of government; it’s also very much an effort to support a thriving and innovative startup ecosystem. 

This won’t be easy. In fact, it might be impossible. There will be endless lawsuits, and large, powerful businesses with enormous lobbying budgets will scramble to protect the status quo.

But if it’s successful, DOGE has the potential to reduce the size of government and weaken the big established incumbents, creating more opportunities for startups to drive innovation. And it may realign some aspects of the American political party system. If it doesn’t succeed, it may simply underscore and reinforce how entrenched the existing system and structure have become.

Breaking Down $4.5 Trillion

Healthcare is a $4.5 trillion dollar industry.

I can’t tell you how many startup pitch decks start by stating this fact. Unfortunately, without more details, this number is somewhat meaningless with regard to the vast majority of healthcare companies. Better to break the $4.5t down into parts and talk about the share that your company will seek to impact or how it may shift dollars across categories. Here’s how the $4.5t breaks down at a high level:

  • Hospitals and Healthcare Facilities – 31% (~$1.4 trillion)

  • Physician and Clinical Services – 20% (~$900 billion)

  • Prescription Drugs and Pharmaceuticals – 10% (~$450 billion)

  • Health Insurance and Payers – 29% (~$1.3 trillion)

  • Medical Equipment and Devices – 6% (~$270 billion)

  • Healthcare IT and Digital Health – 4% (~$180 billion)

  • Home Healthcare and Long-Term Care Services – 5% (~$225 billion)

Even these categories are way too broad to tell a good story around (as an example, the EHR industry is about $35 billion out of the $180 billion healthcare IT industry; cancer drugs are about $200 billion out of the $450 billion pharma industry).

I love a company story that starts at a high level that everyone can understand and then zooms in deeper and deeper, educating the listener along the way. So it’s a great idea to start with the $4.5t, but that’s just the start of a much more interesting drill down into what you plan to do and how you plan to do it.

Why Is It So Hard To Sell To Health Systems?

As a seller, you want to sell to an organization with a single decision-maker who’s free from regulatory constraints, has high margins, a risk-taking mindset, plenty of cash, and no legacy systems in place to slow things down. This is the exact opposite of a typical health system.

Many salespeople claim their market segment is the toughest. But those who sell to health systems might just take the prize. Health systems are notoriously challenging to sell into. To sell to these organizations more effectively, it’s helpful to consider why that is.

1. Complex Organizational Structure


Health systems have very complex ownership and decision-making structures. There are multiple layers of authority, often with competing interests, incentives, and priorities: executive leadership, service line leadership (orthopedics, cardiology, nephrology, etc.), procurement leadership, and technology leadership, all of whom can veto a decision. Clinical needs can also quickly shift priorities, sometimes sidelining other initiatives. And then there’s the troublesome “innovation” team, often connected to a venture investment fund with its own set of disjointed incentives. Selling a product to a health system often requires buy-in, alignment, and approval from all of these stakeholders. A key part of the job for a salesperson is to help the buyer navigate their own internal processes to enable a purchase.

2. Regulatory and Compliance Constraints

Health systems face numerous layers of regulatory oversight that can significantly slow down procurements. Requirements include HIPAA, accreditation standards, state licensing, anti-kickback laws, and CMS guidelines, to name a few. On the technology side alone, there are the HITECH Act, EHR incentive programs, FDA software regulations, FISMA, and interoperability standards. Vendors must undergo rigorous vetting and compliance processes, which can radically slow and often end a sales cycle. It’s crucial that sellers have a deep understanding of the regulatory and compliance issues that overlap with their products.

3. The Dominance of the EHR

Few industries have a software vendor that wields as much influence over internal decision-making as EHR vendors do in healthcare. These are giant, long-term contracts, and depending on where a health system is in its EHR implementation, dozens to hundreds of EHR employees can be embedded within the health system. Often, if you’re selling a software product, someone in the health system will consult their EHR vendor before even considering a conversation. These EHR vendors frequently have ancillary or directly competing products, and there’s a saying among health tech salespeople that the large EHR Account Managers are trained to respond to any new software procurement by saying, “We already do that.” And often, once you get approval to move ahead, a lengthy integration conversation must be waded through, both in terms of feasibility and timing.

4. Low Risk Tolerance

Given the life-and-death nature of their work, inherent low margins, litigious concerns, mostly not-for-profit structures, and heavy regulatory burdens, health systems rightfully prioritize avoiding mistakes over taking risks. This makes selling a new, unproven product quite challenging. They want free trials, extensive case studies, flexible contract terms, and numerous customer references. Their ROI standards are stringent, and they rely heavily on evidence-based data before making a decision. Also consultants are often brought into the process as well to help reduce risk and add rigor, adding further scrutiny and potentially misaligned incentives. A healthy cautiousness is a key part of the culture of a health system.

5. Health Systems Are (Mostly) Local

Over time, most industries will consolidate down to a few national or global players. This isn’t true in healthcare. There are 2 to 4 dominant health systems in each large metropolitan area in the country. There is some overlap via large regional players or national health systems, but not a ton; it’s a highly fragmented space. There are a bunch of very large health systems businesses scattered across the US. There are 5 US airlines whose annual revenue exceeds $5 billion. There are nearly 10 times as many US health systems that meet that threshold. These factors make selling more difficult for a variety of reasons. You don't have a consistent set of priorities across markets to sell into. There's often allegiance to local or regional vendors. It's hard to leverage competition because a New York health system doesn’t care much about that big account you won in Houston. More broadly, the lack of scale in these local health systems trims margins and makes budgets much tighter than they might be on a national scale. 

6. Supply & Demand Mismatch

Over the last decade, more than $100 billion in venture capital has poured into health tech startups, creating a vast supply of vendors that need to show a return on that capital by selling their products to health systems. The supply of products far exceeds the demand, leading to vendor overload for health systems. There’s a lot of noise out there that buyers are forced to wade through. Many health systems have responded by launching innovation teams, some with venture funds attached, which attract vendors to test products using health system staff and provide the fund with deal flow. These innovation teams often wield outsized influence, creating incentive misalignment and internal conflict. Even when these aren't in place, you can bet that the health system you're selling to is pretty sophisticated at sidestepping salespeople.

Complexity As A Moat

Judy Faulkner, founder and CEO of Epic, had a good blog post the other day titled More Complex Than Rocket Science where she talks about the complexity involved in healthcare IT. From the post:

"My favorite t-shirt says, “Healthcare IT is more complex than rocket science.” The three Epic employees who used to work in rocket science agree."

Healthcare IT is absolutely super complex. And that complexity creates a ton of challenges for founders trying to get their idea into market. But that complexity is also an advantage in that it creates a moat around a business where it's very difficult for a copycat to come along and recreate what the company is doing. For example, if you're doing automated care management for cystic fibrosis (CF), you need to wrap your head (and your product) around specific nutrition insights, medications, lung function testing, infection management, psychological support, financial aspects of CF care, and then roll that into a service with some technology wrapped around it. And that's just to build a useful product, never mind the challenges associated with taking it to market.

The upside of the pain in taking a healthcare product to market is that often the product/market fit you’ve found is its own moat.

Growth Endurance, Benchmarks, & Horizontal SaaS vs. Vertical SaaS

Investors will often refer to SaaS benchmarks to gauge how well their portfolio companies are performing. They'll look at things like growth rate, CAC/LTV, gross margin, EBITDA margin, net revenue retention, etc. They'll often cite the most successful companies like Monday.com, Zoom, Hubspot, ServiceNow, and Zendesk. These are all top-tier SaaS companies, and investors like to have their companies aspire to have similar metrics. 

These companies, and nearly all of the top-tier SaaS companies, have two important things in common:

1/ They can sell into virtually any company in any industry (horizontal SaaS). 

2/ They can sell into virtually any country. 

As an example, in theory, Zoom could sell a license to everyone over the age of 18 with an internet connection — let's call that about 3.5 billion people. So their overall total addressable market (TAM) is 3.5 billion multiplied by, say, $100 per year. So Zoom's TAM is something like $350 billion.

Now consider a healthcare technology company that operates within the complex, highly regulated US healthcare system (vertical SaaS). They have a much smaller TAM than Zoom. There are about 21 million US healthcare workers, so, in theory, if a health tech company could get its product into every healthcare worker’s hands at $100 per year, their TAM would be $2.1 billion, about 0.6% of Zoom's TAM. Obviously, I'm using ridiculously simplistic numbers.

This becomes relevant when we start thinking about benchmarks, particularly with regard to growth and growth endurance (the ability of a SaaS company to sustain consistent growth over time).

Consider Everett Roger's Technology Adoption Curve, which illustrates how different groups adopt new technologies over time. 

 
 

You start by acquiring the innovators, then the early adopters, etc. As you move through the curve and gain more and more customers, each sale typically gets more and more difficult. The first two parts of the curve (innovators and early adopters) generally represent about 16% of the addressable market for the technology.

So, using the examples above, when the health tech company gets to 16% of the market, its revenue is $336 million. When Zoom gets to $336 million in revenue, it hasn't even made a dent in the innovators and early adopters. It has another $349,664,000,000 in innovator/early adopter revenue to go get. 

If an investor benchmarked the health tech company against a horizontal SaaS company like Zoom on things like growth, growth endurance, or the cost of acquiring a marginal customer, they'd be very, very disappointed. To say the least!

Now, obviously, it’s on the health tech company to figure out how to innovate, sell its product to a wider audience, and go international, but the point here is that we're not talking about apples to apples. Benchmarks that don't take into account the uniqueness of a business or a particular industry are, at best, a waste of time and, at worst, create really bad incentives for founders and management teams. 

Hospitals & Financial Engineering

I haven't written much on the business of healthcare lately, but this Steward Healthcare situation is both fascinating and troubling. For those that haven't been following, Steward recently filed for bankruptcy and is threatening to close hospitals in high-need parts of Massachusetts, and a formal federal investigation into the actions of the CEO and private equity firm that formerly backed the health system seems likely. This news raises real questions about the appropriateness of hospitals operating as private equity-backed for-profits and the financial engineering that comes with such transactions, especially hospitals that operate in underserved communities.  

Steward Healthcare

Steward Healthcare, a for-profit hospital chain, launched in 2010 when private equity firm Cerberus Capital Management (named after Cerberus, the three-legged dog that guards the gates to hell) acquired the failing non-profit Catholic healthcare system Caritas Christi located in Massachusetts. The CEO of Caritas, Ralph De La Torre, became CEO of this new health system. Steward’s name was a symbol of how it promised to be a good steward of the hospitals formerly owned and operated by the Catholic church.

Steward's Strategy

Hospitals might not strike you as a great investment for a private equity firm, so you might wonder what the appeal was for Cerberus. Hospitals have very low margins (generally less than 5%) and sometimes operate at a loss through government subsidies. But Cerberus saw that one could think of Steward, or any hospital chain, as two separate things: 1/ a large hospital operation serving patients and 2/ a highly valuable set of real estate located in population centers that the hospitals sit on. 

Real estate as an investment is a much more lucrative business than a hospital operation. A real estate investment trust (REIT), a company that owns, operates, or finances income-producing real estate, sees 25% to 50% margins. Cerberus saw that Steward could get significant and quick liquidity by selling the real estate that the hospitals were sitting on to a REIT, in this case, a firm called Medical Properties Trust (MPT), and then leasing the property back. This is known as a sales-leaseback. To juice the price of the real estate, Steward agreed to very favorable leases. MPT paid $1.2 billion for the initial properties and also took a 5% stake in Steward. All of the details of these leases aren't clear, but these were expensive, long-term leases with escalator clauses and with other terms that MPT must have liked, including a triple-net lease where Steward would be responsible for the cost of insurance, property management, and maintenance, in addition to the rent.

The strategy was clearly great for MPT as it immediately expanded its assets under management with reliable, lucrative leases. And it was also good, in theory, for Steward. Steward would gain instant liquidity to help it pay down its debt from the Caritas Christi purchase and acquire more hospitals and medical offices across the country. The properties, as they were acquired, were promptly sold to MPT and leased back. And by not being burdened by managing the real estate, Steward could focus on optimizing its hospital operations. 

Steward aggressively pursued this strategy, growing up to 40+ hospitals across multiple US states and even expanding the strategy internationally into Colombia, Malta, and the Middle East.

The problem was that as Steward was rapidly acquiring and selling real estate, much of the proceeds from these real estate sales never got to Steward. Some of it went to hospital operations and paying down debt, but large amounts of it went back to Cerberus in the form of management fees and dividend payments. And that left Steward without much of the proceeds of the sale and with highly burdensome lease obligations. 

Cerberus Exits 

In 2020, Cerberus exited its position in Steward by selling its stake to De La Torre and other Steward physicians via a loan from MPT. Over the course of its ownership, it was reported that Cerberus made a profit of $800M. 

It was downhill from there. Steward quickly began to downsize, selling off hospitals across the country. By January of this year, Steward was facing a financial crisis. It owed MPT $50 million in unpaid rent, among several other vendors. MPT, presumably to keep the gravy train running, stepped up and offered several loans to Steward to keep the health system solvent. It was soon reported that Steward would be forced to file bankruptcy and close a number of hospitals, which then launched a series of investigations into Steward's operations and financials, which brings us to today, where hospitals in high-need areas are at risk of closing, creating a potential public health crisis in Massachusetts. 

What's Next

What happened here, in short, is a smart private equity firm saw an opportunity to buy up a struggling health system for small dollars, sell off the valuable real estate it sat on, and maximize those sales by saddling it with costly leases and using the proceeds from the sales to pay itself and expand this strategy across the country and the world. Then it sold off the entire asset, leaving the real estate owner (MPT) and Steward's management and employees in the lurch.

To be clear, It's not obvious that any of this activity is illegal (it's probably not). And in most industries, you could argue business is working as it should. Steward likely wasn't a great business at the start, and finding a way to maximize the assets of an investment seems like good old-fashioned capitalism. If Steward was a tech company or an apparel company, it’s likely nobody would know about this mess.

But it's not. It's a health system that operates dozens of hospitals in high-need areas. Hospitals that represent our society at its best. These are places of healing for humans facing the worst moments of their lives. They restore health, reduce human suffering, and support the overall well-being of the communities in which they operate. Not to mention, they generally receive at least half of their revenue from tax payer-funded healthcare. Because of that, I think regulation of these kinds of transactions and even for-profit hospitals, in general, are set to receive some intense scrutiny from regulators in the coming months. De La Torre is scheduled to testify in front of Congress in September.

I'm a big fan of capitalism, and I generally support the work of private equity firms in delivering returns to their shareholders, many of which are large pension funds, endowments, and foundations. But Steward's collapse is an important signal that our most important and prized institutions shouldn’t be operated as attractive targets for short-term, financially engineered profits.

Hospitals are different. They're a special thing. And regulators should ensure they're treated that way.

Business Models & Tech

This somewhat dated (2015) but still highly relevant essay by Alex Danco offers an insightful overview of the state of software in healthcare. If you care about this sort of thing, I highly recommend reading it.

The most interesting aspect of the piece for me is the reminder that when tech impacts or “disrupts” an industry, the tech isn’t necessarily the interesting part. The interesting part is the business models that change or emerge as a result of the tech.

Here are a few examples of what I mean:

Spotify leveraged technology to change the business model of music from $10 per album to 40 million songs for $10 a month.

AirBnB leveraged technology to change the hospitality business model, listing 6 million rooms and homes while owning zero properties. 

Uber leveraged technology to change the taxi business model, doing 4 million rides per day, while owning zero vehicles or taxi medallions.

As we consider how much software has impacted (or not impacted) healthcare, we shouldn’t be looking for the flashy, healthcare-specific, transformational technologies. We should consider the new and emerging business models that are enabled or enhanced by technologies. Those aren’t hard to find.

Collaboration & Enterprise Software

Kevin Kwok wrote a must read piece a few weeks ago about how crucial it is for collaboration to be a fundamental, “first party” aspect of enterprise software.

People think of Slack as a collaboration tool. But Kevin makes the point that a major reason Slack is so necessary (and valuable) is that other applications and business processes are fundamentally broken. You need Slack to fill in the gaps. You switch out of a productivity app (Salesforce) and move to a collaboration app (Slack) because Salesforce doesn’t have collaboration as a primary aspect of the product.

As an example, a sales manager might be in Salesforce and notice that a revenue number on a particular deal is inaccurate. The manager will go to Slack and send a message to the rep. The rep will respond in Slack and go fix the number in Salesforce. If Salesforce was truly collaborative, all of this communication would’ve happened inside of Salesforce. But it’s not. And that’s where Slack picks up the slack for non-collaborative business applications (pun intended). From the piece:

The dream of Slack is that they become the central nervous system for all of a company’s employees and apps. This is the view of a clean *separation* of productivity and collaboration. Have all your apps for productivity and then have a single app for coordinating everyone, with your apps also feeding notifications into this system.

But productivity *isn’t* separate from collaboration.

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It’s not that Slack is too distracting and killing individual productivity. It’s that your company’s processes are so dysfunctional you need Slack to be distracting and killing individual productivity.

For the first 10 to 15 years of my career, I used Microsoft Office applications. I didn’t consider anything else. They had a total monopoly. In the last five or so years that has completely changed. I never use Word or PowerPoint (I still use Excel frequently). For word processing and presentations I almost exclusively use Google Docs and Google Slides. I’ve made this change for one reason and one reason only: collaboration. G Suite (Google’s suite of productivity applications) is fundamentally built on collaboration. It works really well. Collaboration in Microsoft Office applications is clunky and was clearly an afterthought. It’s very difficult to start with productivity only, run that playbook for several years and then back into collaboration. Collaboration from the outset makes things a lot easier.

Healthcare software is suffering greatly from the fact that the software clinicians use didn’t have collaboration as a fundamental part of the code. Most medical software was rushed to market in response to government incentives and collaboration across different organizations wasn’t important. Now, like Microsoft Office tried to do, many of these applications are trying to back into collaboration as a fundamental feature and it’s not working.

This is one of many reasons that PatientPing exists and is growing so quickly. Our software puts collaboration first. Our entire platform is built around collaboration and allowing disparate healthcare organizations to collaborate on shared patients. We’ve tapped into a desperate need because of the way healthcare software was developed. If collaboration had been build into healthcare software from the beginning, our product wouldn’t be in such demand.

Similarly, Slack is widely touted as the fastest growing business application in history. Not to take anything away from their success, but much of the reason for their success is that Slack picks up the slack of so many other widely distributed productivity applications across nearly every industry. The lack of fundamental collaboration in productivity apps created the conditions for Slack’s massive success.

The Apps > Infrastructure > Apps > Infrastructure Cycle In Health Tech

Union Square Ventures had a great blog post the other day on The Myth of the infrastructure Phase

They argue that the narrative in tech that says there’s an orderly infrastructure phase followed by an application phase is a bit of a myth. Instead of orderly and distinct phases, they argue, it looks more like an ebb and flow. Apps, in many cases, drive infrastructure then that infrastructure enables new apps, and vice-versa. From the post:

“Planes (the app) were invented before there were airports (the infrastructure). You don’t need airports to have planes. But to have the broad consumer adoption of planes, you do need airports, so the breakout app that is an airplane came first in 1903, and inspired a phase where people built airlines in 1919, airports in 1928 and air traffic control in 1930 only after there were planes.

The same pattern follows with the internet. We start with the first apps: messaging (1970) and email (1972), which then inspire infrastructure that makes it easier to have broad consumer adoption of messaging and email: Ethernet (1973), TCP/IP (1973), and Internet Service Providers (1974). Then there is the next wave of apps, which are web portals (Prodigy in 1990, AOL in 1991), and web portals inspire us to build infrastructure (search engines and web browsers in the early 1990’s). Then there is the next wave of apps, which are early sites like Amazon.com in 1994, which leads to a phase where we build infrastructure like programming languages (PHP in 1994, Javascript and Java in 1995) that make it easier to build websites. Then there is the next wave of more complicated apps like Napster (1999), Pandora (2000), Gmail (2004) and Facebook (2004) which leads to infrastructure that makes it easier to build more complex apps (NGINX and Ruby on Rails in 2004, AWS in 2006). And the cycle continues.”

We’ve seen this trend in healthcare technology as well.

The first electronic medical record dates back to the 1960s when Dr. Larry Weed created the problem-oriented medical record that allowed his fellow providers to see notes, medical history, etc. in an electronic format (application). The first EMR as we know it that included additional functionality such as billing and scheduling was launched in 1972 by the Regestrief Institute, though adoption was extremely slow. In the 1980s, the need to transfer clinical information between providers led to the creation of Health Level 7 (HL7), a set of international standards for transfer of clinical data between different applications (infrastructure). By the late 1980s, low-cost personal computers (more infrastructure) allowed providers to do what Dr. Weed was doing at scale. The emergence of the internet in the 1990s (more infrastructure) allowed providers to use electronic medical records remotely, increasing adoption and leading to more use cases (more applications).

Today, thanks to meaningful use incentives enacted under President Obama, the vast majority of healthcare providers use electronic medical records and Dr. Weed’s initial application has become an infrastructure of its own. EMRs, originally just a collection of apps that sat on top of an infrastructure, have now become the infrastructure for a new wave of applications that can plug-in to the data stored within the EMR.

Now we’re seeing a new layer of infrastructure being built that will connect all of these EMRs to one another across the full continuum of care — acute to subacute to post acute to home care to ambulatory, etc. There are lots of organizations working on this (including my own) and there’s no doubt that success is on the horizon.

Once this “connective” infrastructure is built we’ll see a new wave of health tech applications that will be built on top and will bring enormous value to our healthcare system.

We don’t need airports to have planes, and we don’t need connectivity to have medical records. But pilots, patients, and providers are a lot better off when we do.