Annotations (26)
“Mari walks in the house and hands me the journals. She goes, 'The problem with their stress is you. They're working two jobs. They got their kids on Medicaid because they can't afford dependent coverage. They got people on food stamps. They're calling bill collectors while they're on break. You're not paying them enough.' 81% were women. 20% of families were on food stamps, 25% of kids were in Medicaid. So I raised minimum wage to $16. It was $75 million the first year.”— Mark Bertolini
Bringing Wellness to the Office · p. 19
Leadership & Management · Business & Entrepreneurship · Economics & Markets
DUR_ENDURING
$75M wage raise, doubled stock price
“We did a bicoastal double-blind study. We had 795 employees sign up. We did cortisol levels and heart rate variability. After 12 weeks of mindfulness and yoga classes, what we found is that the people in the highest quintile of stress spent $2,500 more a year on healthcare than the average employee. After 12 weeks, heart rate variability and cortisol levels dropped 50% in this population. Our healthcare costs went down, not trend. The actual dollar cost went down 7.5% the next year.”— Mark Bertolini
Bringing Wellness to the Office · p. 19
Business & Entrepreneurship · Operations & Execution
DUR_ENDURING
Yoga program: 50% stress drop, 7.5% cost drop
“The spreadsheet is the worst invention ever created for business. We created a tool that allows us to manipulate numbers on the page to get the answer we want. Then we manage to it. We create a belief system that's not real. Instead of saying, what are the five risks on this page? Let's discount all the soft benefits by 90%. The group we discounted by 90% added up to the exact same amount as the hard savings. What it meant was we were just not seeing far enough.”— Mark Bertolini
Bringing Wellness to the Office · p. 20
Strategy & Decision Making · Operations & Execution
DUR_ENDURING
Spreadsheets create false belief systems
“Instead of waiting for all the perfect information to move forward, you develop a hypothesis, build a process around managing that hypothesis, take in the data as you move along, and then ultimately it becomes a better thing. If you look at all the great innovations in our society, those things didn't start as the thing that entrepreneur started with. Apple's green and orange and yellow boxes aren't what made them successful today. So it's about navigation.”— Mark Bertolini
Build, Fix, Scale, Repeat · p. 5
Strategy & Decision Making · Creativity & Innovation
DUR_ENDURING
Hypothesis, process, navigate; product evolves
“It starts with just doing the basics right. It's like trading in the markets. It all starts with a T-account. Someone's asset is another person's liability. That's it. You have to show people the connections and the line of sight instead of looking at each thing and saying, 'Here, fix this, fix this, fix this.' When they start to see how it all fits together, then you've recruited everybody into a mental model about how the world works that we can share.”— Mark Bertolini
Build, Fix, Scale, Repeat · p. 6
Leadership & Management · Operations & Execution
DUR_ENDURING
Show connections, not tasks: shared mental model
“I developed the concept of Platonists versus Aristotelians. Platonists are people who think the great idea, communicate it and consider their job done. Aristotelians actually have to translate it into real work. I found that being an Aristotelian was far more powerful than being a Platonist. There are a lot of people with great ideas. Not too many people can actually make them happen.”— Mark Bertolini
Build, Fix, Scale, Repeat · p. 4
Leadership & Management · Operations & Execution · Philosophy & Reasoning
DUR_ENDURING
Platonists think, Aristotelians execute; execution wins
“You have to get down in the mud and crawl on your belly below the pillbox slot so you don't get shot. It's literally the work of doing deep, deep thinking. Over my time, I found that while I thought I was right 100% of the time, I'm really only right about 35% of the time. But it's the issue of making a decision and moving forward. If you have a good management process around it, it will get better as you go along.”— Mark Bertolini
Build, Fix, Scale, Repeat · p. 5
Strategy & Decision Making · Leadership & Management
DUR_ENDURING
Right 35% of time, but decide and iterate
“Ron Williams is sitting there and he goes, 'Those questions you put together for everybody, why don't you actually listen to the answers instead of preparing the next question and come up with two more questions as a result of the answer? You'll be amazed at how much smarter you are.' Now I know 35% of the time I'm right, and the rest of the time I got to learn by asking questions. So it changed my style completely.”— Ron Williams
Unfinished Business · p. 32
Leadership & Management · Psychology & Behavior
DUR_ENDURING
Listen to answers, not prepare next question
“There's a quote I have had under my blotter every day of my working career. It was Niccolò Machiavelli when he wrote to the Prince: there's nothing more dangerous than to initiate a new order of things, because those who are advantaged by the current order have the laws behind them and experience to continue to support the way it is. And for those who would be advantaged by the new order of things really won't embrace it until they experience it. And between the two, you run great danger.”— Niccolò Machiavelli
Barriers to Scaling · p. 13
Strategy & Decision Making · Philosophy & Reasoning · History & Geopolitics
DUR_ENDURING
Machiavelli: incumbents defend, beneficiaries wait
“Health insurance was started 80 years ago as a result of soldiers coming back from war. They were worried about wage inflation. So they said we can't have any increases in wages competing for talent, but you can create benefits. There will be operating expenses that you can expense into your business and it won't be taxable to the individuals. If you create enormous capacity and you give people no sensitivity to price by giving them coverage, you have created a great inflationary monster.”— Mark Bertolini
The $75 Billion Healthcare Problem · p. 7
Economics & Markets · History & Geopolitics
DUR_CONTEXTUAL
Capacity plus price insensitivity equals inflation
“My dad said, 'Let me tell you about Jerry. Jerry's got a family. He's got responsibilities. I have an obligation to Jerry. You're 14 years old. Were you happy before? Do you want your job back? You start tomorrow at a dollar an hour.' He cut my pay. 'This is a very important lesson for you. Never count anyone else's money. Never compare yourself to anyone else on how much money you have. Make sure you share it when you have enough.”— Mark Bertolini's father
Business Success Stories · p. 24
Philosophy & Reasoning · Leadership & Management
DUR_ENDURING
Never count anyone else's money
“The Dalai Lama said: 'In your heart, you need to find compassion for the journey they're on, because everyone has their own journey in life. But physically run.' This was about people who frighten you. Find compassion for their journey, but remove yourself from their proximity.”— Dalai Lama
Memento Mori · p. 2
Psychology & Behavior · Leadership & Management · Philosophy & Reasoning
DUR_ENDURING
Compassion for their journey, distance from their person
“Last year, two out of five Americans borrowed $74.9 billion to pay their out-of-pocket costs for healthcare from banks. What if I get defined contribution from my employer for what they're paying for me today and I buy a plan that suits me at a better cost? I can use the money left over to pay those out-of-pocket costs instead of going to the bank. Or I can buy dental and vision, life insurance or disability. All of a sudden, it's my plan, it's my choice, it's what I want.”— Mark Bertolini
The $75 Billion Healthcare Problem · p. 8
Economics & Markets · Strategy & Decision Making
DUR_CONTEXTUAL
$75B borrowed for out-of-pocket costs annually
“Josh Kushner called me and said, 'I hear you're in meetings asking questions. When are things going to happen?' I said, 'Josh, I have screwed up everything at least twice myself. I know I could walk in here and say, do this, do this, do this, and we'll be just fine. But what I want to do is find out where people are and how they think about it so that I can figure out how to bring them to a place where they can succeed.”— Mark Bertolini
Build, Fix, Scale, Repeat · p. 5
Leadership & Management
DUR_ENDURING
Help ordinary people do extraordinary things
“We need to eliminate employer-sponsored insurance. We need to let individuals buy their own, but we need a marketplace to do that. The economics of large networks are that they are inversely cost-effective. The larger the network you have, the less stability you have to negotiate better rates. When you give an average benefit for employees, the employees have to decide which is the best for them. They settle for whatever they get and they have to pay 15% out-of-pocket.”— Mark Bertolini
The $75 Billion Healthcare Problem · p. 7
Economics & Markets · Strategy & Decision Making
DUR_CONTEXTUAL
Larger networks, worse negotiating power
“The mental model that exists inside your head about how the world works is the most critical tool you have. If you don't constantly add new information to it and are not a continual learner, you can't possibly know what you need to know to make good decisions. I look for two things in executives: curiosity and courage. The curiosity to continue to ask questions and learn more every day, and the courage to act on it when you have a hypothesis that might be powerful.”— Mark Bertolini
How Curiosity Drives Better Decision-Making · p. 14
Leadership & Management · Philosophy & Reasoning
DUR_ENDURING
Curiosity to learn, courage to act
“They said, 'You don't have intractable pain. You have neuroplastic pain, and we can fix it.' They had done MRIs on baseball hitters. The best baseball hitters, their visual, cognitive and motor cortices light up instantaneously. There's no latency. You have a baseball hitter's brain on pain. There's no latency in your system. Something touches your arm, you're in pain.”— Mark Bertolini
Overcoming Pain · p. 22
Biology, Ecology & Systems · Technology & Engineering
DUR_ENDURING
Baseball hitter's brain on pain: repatterned
“A friend sent me this memento mori ring after my accident. He said, 'Remember, you will die.' Every day when you wear this ring, look at it and ask yourself: am I spending my time with the right people, doing the right things? And if you're not, run. So it's always been a thing: am I in the right place doing the right things?”— Mark Bertolini
Memento Mori · p. 1
Philosophy & Reasoning · Psychology & Behavior · Leadership & Management
DUR_ENDURING
Daily mortality check: right people, right things
“I learned that there is no good bully. And the only way to beat a bully is to challenge them. I was the one who always defended my brothers from bullies. I carried that into my career. I was an autoworker on the assembly line at Ford Motor Company. Got in a fight with my union steward because I changed my work rules. I moved my stuff around and he didn't like that. I said, 'How do I get your job?' He said you need a degree, kid.”— Mark Bertolini
Life and Work · p. 3
Leadership & Management · Psychology & Behavior
DUR_ENDURING
No good bully; only way to beat: challenge
“All they need to do is believe they can do it. You have to paint for them. You have to tell a story about why it matters. One of the first things I said at Oscar is, 'We are a pirate ship filled with cannons among Spanish galleons filled with gold. All we have to do is take their business. They don't think we can succeed. We're too small.' But we have none of the ballast that they carry around with them about how they run their business. They won't go where we will go, and that's how we win.”— Mark Bertolini
Build, Fix, Scale, Repeat · p. 6
Leadership & Management · Strategy & Decision Making
DUR_ENDURING
Pirate ship vs Spanish galleons: narrative wins
Frameworks (1)
The Memento Mori Decision Filter
Using mortality awareness as a daily decision-making framework
A daily practice of using mortality awareness to evaluate whether you're spending time with the right people doing the right things. If the answer is no, the directive is simple: run. The framework creates a forcing function that cuts through rationalization and forces honest self-assessment.
Components
- Daily Ritual
- The Two Questions
- The Run Directive
Prerequisites
- Physical reminder object
- Honest self-assessment capability
Success Indicators
- Clarity on priorities
- Decisive action when misaligned
- Reduced regret
Failure Modes
- Becoming habitual without reflection
- Rationalizing away discomfort
- Forgetting the action component
Mental Models (10)
Memento Mori
TimeUsing awareness of mortality to focus on what matters. The principle that contem
In Practice: Bertolini's daily practice of asking whether he's with the right people doing th
Demonstrated by Leg-mb-001
Compassion Without Proximity
PsychologyThe ability to maintain empathy for someone's journey while physically removing yourself from their influence.
In Practice: The Dalai Lama's advice about people who frighten you
Demonstrated by Leg-mb-001
Earned Participation Through Merit
EconomicsThe principle that access to opportunities should be contingent on demonstrated capability, not guaranteed regardless of performance.
In Practice: Bertolini's childhood sandlot baseball experience where you only got to play if you were good enough to be picked
Demonstrated by Leg-mb-001
Hypothesis-Driven Navigation
Decision MakingBuilding a management process around a hypothesis rather than waiting for perfect information, then iterating based on incoming data.
In Practice: Bertolini's approach to decision-making: accept that you're only right 35% of the time, but make decisions and navigate based on feedback
Demonstrated by Leg-mb-001
Shared Mental Model
Systems ThinkingThe principle that organizational alignment comes from everyone understanding how the system fits to
In Practice: Bertolini's approach to leadership: show people the connections and line of sight instead of just as
Demonstrated by Leg-mb-001
Price Insensitivity Drives Inflation
EconomicsWhen consumers have no price sensitivity (because a third party pays), and supply is abundant, you create an inflationary spiral.
In Practice: Bertolini explaining how employer-sponsored insurance combined with hospital overcapacity created the healthcare cost crisis
Demonstrated by Leg-mb-001
Network Size Inverse to Bargaining Power
EconomicsIn certain markets, larger networks reduce leverage because the buyer loses the ability to exclude or preferentially direct volume.
In Practice: Bertolini explaining why large insurance networks are inversely cost-effective compared to narrow networks
Demonstrated by Leg-mb-001
Stress Cost Link
EconomicsHigh-stress individuals incur significantly higher healthcare costs; reducing stress reduces costs more than trend.
In Practice: Aetna yoga study showing highest-stress quintile spent $2,500 more annually; wellness program reduced costs 7.5%
Demonstrated by Leg-mb-001
Wage Investment Flywheel
EconomicsRaising wages for frontline employees above market rate can create a self-reinforcing cycle of reduced stress, better performance, lower costs, and higher stock value.
In Practice: Bertolini's $75M minimum wage increase at Aetna doubled stock price by reducing employee stress and improving member care
Demonstrated by Leg-mb-001
The Tyranny of Excel
Decision MakingSpreadsheets enable manipulation of numbers to justify predetermined conclusions, creating false belief systems that organizations then manage toward.
In Practice: Bertolini's critique of spreadsheet-driven decisions; proposed instead asking about top five risks rather than optimizing numbers
Demonstrated by Leg-mb-001
Connective Tissue (2)
Platonic philosophy versus Aristotelian philosophy as a framework for distinguishing between idea generation and implementation capability in organizations
Bertolini uses the distinction between Platonists and Aristotelians as an organizational framework. Platonists think the great idea, communicate it, and consider their job done. Aristotelians translate ideas into real work. In ancient Greek philosophy, Plato emphasized the world of perfect forms and ideas, while Aristotle focused on empirical observation and practical application. This philosophical distinction maps precisely onto the modern business problem of distinguishing between strategic thinkers who generate concepts and operational leaders who execute them. The insight is that execution capability (Aristotelian thinking) is more valuable than idea generation (Platonic thinking) because ideas are abundant but implementation is scarce.
Bertolini describing his early career lessons about the difference between having ideas and making them happen
Machiavelli's principle from The Prince about the danger of initiating a new order of things, where those advantaged by the current order resist change with the force of law and experience, while potential beneficiaries of the new order don't fully embrace it until they experience its benefits
Bertolini kept this Machiavelli quote under his desk blotter throughout his career: 'There's nothing more dangerous than to initiate a new order of things, because those who are advantaged by the current order have the laws behind them and experience to continue to support the way it is. And for those who would be advantaged by the new order of things really won't embrace it until they experience it. And between the two, you run great danger.' This Renaissance political philosophy insight maps directly to the dynamics of business disruption and organizational change. The incumbents (current order beneficiaries) have structural advantages including legal frameworks, established processes, and institutional knowledge, while potential adopters of new systems are skeptical until proven. This creates a dangerous middle zone where the innovator faces maximum resistance with minimum support. The principle explains why healthcare reform is so difficult: insurance companies, hospital systems, benefit consultants, and regulatory frameworks all defend the status quo, while patients won't advocate for individual choice-based plans until they've experienced their benefits.
Bertolini explaining the resistance to healthcare reform and why Oscar Health faces structural barriers despite offering superior solutions
Key Figures (5)
Eric Bertolini
12 mentionsMark Bertolini's son, theoretical physicist
Mark Bertolini's father
4 mentionsAutoworker foreman, pattern maker
Mari
3 mentionsYoga teacher, Mark Bertolini's partner/wife
Josh Kushner
2 mentionsFounder of Oscar Health
Kushner founded Oscar Health and recruited Bertolini to become CEO.
- Kushner challenged Bertolini's patient approach
Ron Williams
2 mentionsFormer Aetna executive
Glossary (1)
memento mori
FOREIGN_PHRASELatin phrase meaning 'remember you will die'; artistic or symbolic reminder of mortality
“A friend sent me this memento mori ring”
Key People (2)
Dalai Lama
(1935–)Spiritual leader of Tibetan Buddhism; Nobel Peace Prize winner
Niccolo Machiavelli
(1469–1527)Italian Renaissance political philosopher; author of The Prince
Concepts (2)
memento mori tradition
CL_PHILOSOPHYMedieval and Renaissance artistic practice of including symbols of mortality in paintings
Platonism vs. Aristotelianism
CL_PHILOSOPHYPlatonists emphasize ideal forms; Aristotelians emphasize empirical observation
Synthesis
Synthesis
Migrated from Scholia