Greatest Strength = Greatest Weakness

Early in my career, managers were traditionally expected to tell their employees their weaknesses and how to improve them. Then, they would check in every few months to discuss their progress. It took me a long time to realize that this was a mistake. Over and over, in my career, I've found that a high-performing person's weaknesses are what actually make them great at what they're great at. Identifying how an individual’s weaknesses actually support their strength can you give a lot of insight into how to best interact with and manage that person.

  • People who are perfectionists and demand extremely high work quality spend too much time on unimportant things and have trouble prioritizing.

  • People who are great strategic thinkers struggle with on-the-ground execution plans. 

  • People who are extremely adaptable and can respond quickly to challenges struggle with focus and stability. 

  • People who are really optimistic ignore potential obstacles and can be unprepared for setbacks. 

  • People who are highly competitive can create friction in their team and struggle with collaboration.

Hire people who are the best in the world at what they do and let them run after that thing. Spending time having them focus on improving something that they don't do well and probably don't enjoy doing is a low ROI effort. Of course, they should know their weaknesses and how they might impact others and should develop the flexibility and self-awareness to know when to dial them back or complement them with other traits. But doubling down on a high performer’s strengths will lead to much better outcomes and a much happier team.

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.

Assets > Wages

Aside from a short period of turmoil during COVID and the inflation that followed the economic stimulus, the US economy has been pretty strong over the last ~15 years. The stock market is at all-time highs. Unemployment is near all-time lows. Inflation is now mostly back in check. The dollar is strong.

But there is a somewhat troubling trend that people — particularly people early in their careers — should be aware of. And that is the expanding gap between the high growth in asset values versus the relatively low growth in wages. 

Since the Great Financial Crisis in 2008, stock prices have increased 540%, home prices have grown 114%, inflation has increased 50%, while wages have only grown 43%. Unfortunately, this trend contributes greatly to the wealth gap in the US. Generally, lower-income people are less likely to own assets and make most or all of their income from their jobs. People with higher incomes own most of the assets. The rich get richer. Literally.

It wasn't always this way. From 1945 to 1973, wages grew nearly twice as fast as home prices. But this new trend of assets growing faster than wages has accelerated significantly, driven by a variety of factors that are unlikely to change:

1/ Home price inflation. Over the last several decades, zoning and other types of laws have made it almost impossible to build large numbers of new homes in areas where people want to live. While there's plenty of land to build on in the US, bureaucracy gets in the way. Meanwhile, to fuel growth, we need more people to come into the country (through immigration or births). That means more and more demand for homes, which means higher prices. 

2/ Stock prices continue to rise rapidly. The US stock market has really stood out lately compared to virtually any other country. Given our democratic system, the rule of law, and our embrace of innovation, we're really outpacing the rest of the world. And while things might be a bit overvalued due to AI and low interest rates, it seems like there's no end to the scale of the large tech companies that are leading the market. When I was a kid, the largest US companies were companies like General Electric and General Motors. Companies that were selling high marginal cost hard goods, mostly in the United States. Now, we have these tech companies with very low marginal costs selling their product to nearly everyone on Earth. These companies are huge. Facebook has something like 6 billion users. And it costs a lot for General Motors to build a car; it costs Facebook next to nothing to display an ad. 

3/ Wage stagnation. While wages will continue to increase, they won't grow nearly as fast as assets. Offshoring and technological innovation (particularly AI) will put downward pressure on wage increases. Again, as I've mentioned in the past, there will be plenty of jobs, and wages will increase, but people who only generate wealth through their time and effort will continue to fall behind. 

Owners of assets have benefited disproportionality over the last couple of decades. And outside of some earth-shattering change, there's little reason to believe that will stop. 

It’s important to understand these trends and act accordingly. The message to younger people is to start getting their money into assets as much as possible sooner rather than later. Trying to get rich on your time and effort is an uphill battle. Be frugal, start saving and investing as early as possible.

Benchmarks & Storytelling

The other day, a founder asked me about financial benchmarks for a company at his stage. He asked about the optimal CAC/LTV, gross margin, and revenue per employee. 

Benchmarks are important. Investors, particularly investors who don't have intimate knowledge of your company, will use them as a guide for how to value your company. There's a temptation for founders to optimize against top-tier benchmarks. But I think that's unwise. Optimizing against benchmarks is actually relatively easy. What's really difficult is knowing what your company needs right now and optimizing against that. That's a lot harder.

‘Revenue per employee’ provides a very simple example of this concept. Top-tier SaaS companies have a revenue per employee of around $300k. It's tempting to chase that number. The problem is that the easiest way to grow your current revenue per employee is to stop innovating. Get rid of all the employees working on stuff that won't impact revenue this quarter or this year. But that's likely not at all what your company needs right now for a variety of reasons.

So, in many cases, you actually don't want to optimize revenue per employee. That might not be what your company needs right now.

The best approach to this problem is to know your metrics and be aware of top-tier benchmarks but to intelligently apply those benchmarks to your business and be able to explain to an investor and your team why that's the right thing for you right now. A great story around why your revenue per employee is lower than a top-tier company because you are thinking about growth 3 to 5 years from now or why your gross margin is low right now because you're overly investing in your early customers, or why your CAC is high because your testing new marketing channels is a lot more impressive than a simple point in time comparison to benchmarks of companies that might need to optimize around something completely different.

AI In Sales & The Jevons Paradox

A month or so ago, I wrote about the emerging AI business model and its potential impact on white-collar employment. As I said in the post, I'm skeptical that AI will reduce the number of white-collar workers, particularly salespeople. With that in mind, I came across a concept called the Jevons Paradox

The Jevons Paradox says that when technological improvements increase the efficiency of a resource, that leads to higher consumption of that resource, not less.

A couple of examples:

Technologies like home insulation, in theory, would reduce the need for heating and cooling energy consumption. But the effect was that people invested in larger homes resulting in more overall energy consumption.

Electric/hybrid cars bring down energy costs, leading to more frequent driving and longer trips, and more overall energy consumption.

This concept also applies to work.

Flexible work tools like Zoom have added convenience but also made it possible to work more, increasing the number of hours worked. 

Communication tools like Slack and email make communication more efficient but have also led to far more communications and increased workloads. 

I think we'll see the Jevons Paradox at work with AI in sales. As AI takes on more of the job of a salesperson and does things like lead scoring, opportunity prioritization, CRM automation, communication personalization, sentiment analysis, etc., it will bring down the cost of sales. That means that each salesperson costs less per dollar in sales than they did prior to the adoption of AI. That will cause companies to want to do more sales and hire more salespeople to do the work.

The myth is that automation makes the worker superfluous. In reality, the opposite is true because it’s an opportunity for the ambitious to do more. Marketing automation is a great example. Facebook Ads can effectively run highly targeted, comprehensive marketing campaigns, in theory reducing the need for digital marketers. When, in fact, those platforms made marketing cheaper, which led to major increases in the need for more digital marketers to manage these programs and to do more marketing. The same will be true with AI in sales.

When something gets cheaper, we tend to do more of it.

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.

AI & Sales

A few weeks ago, Tomas Tunguz from Theory Ventures gave an insightful talk on the state of SaaS Go-to-Market. One key takeaway was the explosive growth of AI use among sales teams. This isn’t surprising. Sales teams, by nature, are quick to adopt new tools because they’re profit centers. Anything that works will be adopted quickly because it impacts the top line. AI is helping sales teams in several areas—lead scoring, customer research, training, follow-up automation, competitive intelligence, and price optimization, to name a few.

Sales leaders are reporting lots of efficiency gains thanks to AI, but despite the boost in productivity, AI hasn’t moved the needle when it comes to deal conversions or bookings growth.

The reality today is that AI in sales — as it is in many functions — is really like having a bunch of productive interns. They can handle lots of grunt work, but their output needs to be checked, they’re tough to train, they lack company and situational context, and they’re not equipped to make important decisions. AI can’t yet do what great salespeople do. It can’t build emotional connections, navigate complex negotiations, leverage intuition, adapt in real-time to low-information situations, or respond to subtle cues or nuanced human emotions surrounded in layers of context. In short, AI is really good when it has lots of great training data to work with, which is the polar opposite of what a good salesperson does: they shine and show their real value when they lack data, and the next step is unclear, and they have to jump over hurdles to acquire more information or rely on their emotional intelligence, intuition, instincts, and human connection to make a good decision without it.

That said, I do believe the efficiency gains AI provides will eventually translate into better conversions and growth. But I’m skeptical how high up the chain it can go in terms of high value sales activity.

AI in sales will be a fun one to watch. Sales results are pretty measurable, and teams will quickly adopt what works. We’ll see.

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.

Fundraising & Incentive Alignment

There was a really interesting discussion on the “state of venture capital” on the BG2 podcast this week. It's definitely worth listening to the entire episode, but here are three key insights for founders that I thought were worth highlighting, along with some brief commentary:

1/ $100M+ exits are incredibly rare but can be life-changing for founders. Taking 15% of a $100M exit is $15M—not bad at all. But if you've raised $100M in venture capital, a $100M exit is off the table due to the preference stack where VCs get paid first. If you've raised $500M, a $500M exit is off the table. $1bn, etc. Raising more money than you need makes great exits harder and harder to achieve. This is also true of valuations: a high valuation sets a new benchmark for success. There's an important trade-off between driving up valuation (so investors take a smaller portion of your company per dollar invested) and setting expectations so high that even a strong exit may not satisfy investors. I wrote a post a while back about how employees should think about this topic when joining a startup.

2/ Raising too much can lead to a loss of focus, spreading talent too thinly across initiatives. Companies often say they won’t use all the capital they raise, but that’s tough to avoid in practice. If you’re an entrepreneur with a bank full of funds and a head full of ideas, you’re likely going to pursue those ideas. The discipline to keep the money in the bank is inconsistent with the mindset of a creative, ambitious, high-growth leader. And early on, focus is everything, and it’s one of the major advantages a startup has. You only have a small team of top performers that can create outsized value, so spreading them too thin can significantly reduce their impact.

3/ The incentive structure in venture capital has shifted a bit, impacting the alignment between VCs and founders. The venture model, traditionally known as "2 and 20," means firms typically charge a 2% management fee and take a 20% carry (their share of profits when a portfolio company exits). In the past, venture capital was sort of a boutique asset class, with a few players managing smaller funds and relying heavily on that 20% carry to make a profit. Today, due to companies going public later and seeing more value creation in the private markets and the fact that starting a company has become much easier, venture capital has become a far larger asset class with more capital, more investments, and lower margins. As a result, that 2% management fee can become a substantial source of income — 2% of a $1 billion fund is $20 million per year. This structure incentivizes VCs to deploy capital more quickly as they don’t earn that management fee until the money is deployed. It's not a huge deal, but this can lead to some incentive misalignment between a VC and founder, so it’s worth being aware of.

Writing

“I’ve seen many people shy away from writing because it doesn’t come naturally to them. What they overlook is that writing is more than a vehicle for communicating—it’s a tool for learning. Writing exposes gaps in your knowledge and logic. It pushes you to articulate assumptions and consider counterarguments. Unclear writing is a sign of unclear thinking.”

-Adam Grant, Hidden Potential: The Science of Achieving Greater Things

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.