Host: Patrick O’Shaughnessy
Source: Invest Like the Best
Date Read: December 4, 2025


Download Anki Deck

42 cards • Last updated: Dec 2025


Flashcards

1. Value Accrual in Tech Transitions

According to Dev, where does value first accrue during major technology transitions, and why is this important for understanding AI?

Value first accrues at the bottom layer of the stack (e.g., infrastructure/compute like Cisco in 2000 or Nvidia today). This matters for AI because early outsized returns show up in compute providers, while more durable, widespread returns later come from applications that deliver customer value.


2. Early AI Apps vs iPhone Apps

How does Dev compare early AI applications to the early iPhone App Store?

He says today's AI apps (simple chatbots, summarizers) are like the first trivial iPhone apps (flashlight, iBeer). Over time, AI apps will resemble Uber/Airbnb-level transformations: deeply embedded, business-critical applications leveraging real-time data.


3. Long-Term AI Returns

Conceptually, how does Dev think about where the long-term returns from AI will come from?

While early value accrues to compute/infrastructure, he believes long-term returns will come from applications that (1) create great customer experiences, (2) automate and cut costs, and (3) enable new or disruptive business models using AI.


4. AI and Developer Demand

Why does Dev not believe that AI will significantly reduce the need for developers?

Because every dev team already has a large backlog, and historically each tech transition lowers the cost of building apps, leading to more applications and more data. AI will increase developer productivity and thus the number of applications built, not eliminate developers.


5. MongoDB’s Primary Customer

What is MongoDB's primary customer persona, and how is AI changing their workflow, according to Dev?

The primary customer is the developer. AI changes their workflow by increasing productivity and enabling them to build more, richer applications faster; MongoDB is focused on how the developer workflow evolves in an AI-first world.


6. MongoDB’s AI Positioning

What evidence does Dev mention that MongoDB is positioned well for the AI transition?

He points to thousands of startups already building AI applications on MongoDB's flexible, scalable platform, which he treats as a "crystal ball" for future large-enterprise adoption patterns.


7. MongoDB Cloud Business Evolution

How did MongoDB's cloud business evolve after launch, and what does this say about their strategic bets?

Launched in 2016 (pre-IPO), cloud was ~2% of revenue in 2017 and grew to ~68%. Despite skepticism about "partnering and competing" with hyperscalers, MongoDB bet that customers wanted a managed service, not to operate the database themselves—this bet became a major growth driver.


8. Document Model Innovation

What core innovation in data modeling differentiates MongoDB from traditional relational databases?

MongoDB uses a document-based model instead of rigid tables. Data is stored in documents that align with how developers think in code, avoiding the cognitive load of decomposing entities into many related tables.


9. Importance of Databases

How does Dev explain why databases are so important to every digital system?

He says any application (shopping, travel, gaming, mobile, enterprise) depends on persistent data; about 70% of developer time is spent working with data—presenting the right data, at the right time, to the right user in the right context.


10. Database Stickiness

Why are databases considered "sticky" according to Dev?

Once applications are built on a database, migrating them is very hard and expensive. This stickiness explains why many organizations still run Oracle despite disliking it.


11. AI and Database Importance

How might AI increase the importance of databases as models gain "memory," according to Dev?

If LLMs store user history (queries, actions, context) in a persistent data store, switching between models becomes harder because that historical data is valuable and bound to the database, increasing switching costs and the importance of data stores.


12. Leadership and Judgement

What is Dev's central leadership principle for driving excellence, and why does he think most leaders fall short of it?

He believes leaders must be "incredibly judgmental"—willing to make hard, extreme decisions on people, product, and go-to-market. Most leaders avoid painful conversations and accountability, leading to average or mediocre companies.


13. Combating Passive-Aggressive Behavior

How does Dev define and combat passive-aggressive behavior in organizations?

He describes it as people nodding in meetings but privately doubting decisions. He views it as a form of duplicity and combats it by building a culture of intellectual honesty and fierce, direct conversations about what's working and what's not.


14. Formative Leadership Experiences

What personal experiences shaped Dev's bias toward confronting problems quickly?

Raising only $6M right before 9/11 at BladeLogic, during a nuclear winter for tech, forced him to be ruthless about people and decisions—he couldn't afford to be patient with underperformance, which built his "deal with problems head on" muscle.


15. Dangers of Excess Capital

Conceptually, why does Dev think raising too much capital can be dangerous for startups?

Excess capital reduces pressure to make hard decisions quickly, encouraging tolerance of mediocrity and delayed action on people or strategy problems, which can compound and hurt the business.


16. Firing Timing

What is Dev's rule of thumb about firing timing, and what common mistake does it highlight?

He notes almost everyone fires "too late" rather than too early, because they introduce hope and give underperformers more time, even when the evidence shows they won't work out.


17. Inspect vs. Expect

How does Dev's "inspect vs. expect" philosophy change how leaders should manage performance?

Instead of assuming adults will just do what's asked, leaders must frequently and deeply inspect work. When people know performance is regularly inspected, they raise their game and issues are surfaced early.


18. A Place With a Lot of Sunshine

What organizational dynamic does Dev describe with "a place with a lot of sunshine" at BladeLogic?

It meant constant inspection and transparency: no place to hide poor performance or problems because metrics, deals, and execution were continuously reviewed and discussed.


19. Three Core Enterprise Sales Questions

What are the three core questions Dev says any enterprise sales process must answer?

1) Why does the customer want to do anything? (pain/problem)

2) Why MongoDB/our solution? (best option vs alternatives)

3) Why now? (compelling event to avoid decision deferral)


20. The “Why Now?” Challenge

Why does Dev consider "Why now?" the most challenging part of the sales process?

Because customers can accept the problem and your solution but still postpone action; many deals are lost to "no decision," not competitors. Creating urgency is often the hardest part.


21. Champion vs. Coach

What is the difference between a "champion" and a "coach" in Dev's sales framework?

A champion sells for you when you're not in the room, has power and credibility, and is a change agent. A coach wants you to win and gives intel but won't take personal risk or drive the decision.


22. Exceptional Sales Organization Pattern

What output pattern does Dev look for as a mark of an exceptional enterprise sales organization?

Broad-based performance across reps, not an 80/20 pattern where a small minority carries the majority of results, plus consistent execution over quarters instead of yo-yo results.


23. Recruiting + Development

Why does Dev emphasize both recruiting and developing salespeople in building a great sales force?

Recruiting brings in hungry, smart talent, but without development—on product, deal prosecution, qualification, forecasting—those people won't reach their potential or execute consistently.


24. Forecasting and Cash Management

How does Dev link accurate forecasting to cash management in high-growth companies?

In high growth, revenue/bookings forecasts are proxies for expense planning. Poor forecasting can lead to overspending and burning cash too quickly.


25. Three-Step Accountability Process

What is Dev's simple three-step process for holding people accountable?

1) Set very clear expectations.

2) If the person first misses, assume you (the manager) weren't clear and re-explain the why.

3) If they miss again, hold them directly accountable—no ambiguity or hiding.


26. Skills vs. Will Matrix

How does Dev use the "skills vs will" matrix to diagnose people issues?

He asks: Do they have the skill to do the job and the will (drive/motivation)? Failures usually stem from one or both being low, guiding whether to coach, reassign, or exit someone.


27. High-Skill, Low-Will Leaders

If you observe a high-skill but low-will leader, how would Dev's framework suggest you respond?

Investigate why their motivation dropped (e.g., denied promotion, personal issues, misalignment with role) and, if will doesn't return, consider replacing them despite their skills.


28. Judging Leader Scalability

What heuristic does Dev use to judge whether a leader is scaling with the business?

He watches whether they are losing their team—high attrition of good people and declining quality of new hires suggest the leader isn't scaling and is likely failing.


29. A’s Hire A’s

What hiring pattern does Dev observe about talent quality cascading through organizations?

According to Dev, A's hire A's, B's hire C's, and C's hire F's. Watch the quality of people each leader brings in as a leading indicator of their own caliber.


30. Bad News Travels Slowly Up

What does Dev mean when he says bad news travels slowly up but quickly down the organization?

Frontline employees see problems first and clearly; as bad news moves upward, it's filtered and softened, so by the time it reaches the CEO, it's delayed and understated unless leadership actively digs in.


31. Reacting to Bad News

How does Dev react when he hears bad news, and why?

He immediately digs in, assuming he's the last to know and that the situation is worse than presented. This prevents being blindsided later by escalated problems (e.g., churned customers).


32. You Become the Problem

What does Dev say about leaders who see problems but don't act?

Dev says: "If you see a problem and don't act on it, then you're the problem."


33. Recruiting Philosophy

How does Dev's recruiting philosophy go beyond checking resumes and skills?

He probes what makes people tick—their upbringing, hardest experiences, motivations, long-term orientation, and how thoughtfully they made past life and career decisions—to assess grit and values.


34. The Hardest Thing Question

What question does Dev frequently use to uncover a candidate's intrinsic motivation?

"What's the most difficult thing you've ever endured?"

Listen for real adversity, how they responded, what they learned, and whether it created durable grit and drive that will sustain them through startup challenges.


35. Applying the “Hardest Thing” Question

How would you use Dev's "hardest thing you've endured" question when hiring your own leadership team?

Ask it openly, listen for real adversity, how they responded, what they learned, and whether it created durable grit and drive that will sustain them through startup challenges.


36. Three Things When Investing in Tech

According to Dev, what are the three key things he looks for when investing in a technology company?

1) A big market,

2) A defensible technology advantage with proof points,

3) A CEO who is smart and coachable, with the right cultural/values fit.


37. NDR as Product-Market Fit Signal

How does Dev use net dollar retention (NDR) as a signal of product-market fit?

High NDR (e.g., 120%+) shows customers are expanding spend net of churn, indicating the product is delivering ongoing value and justifying more go-to-market investment.


38. Datadog Product-Market Fit Metric

What specific metric at Datadog convinced Dev of its strong product-market fit?

Month-over-month growth of existing customers' spend of around 5%—with relatively junior sales reps—showed easy adoption and rapid expansion.


39. Sequoia and Roelof Botha

What aspect of Sequoia's and Roelof Botha's behavior does Dev especially respect as a CEO?

Their discipline in prioritizing building great businesses over optics, and Roelof's habit of listening carefully and speaking with high signal-to-noise instead of leveraging ownership to dominate board discussions.


40. Three Conditions for Fantastic Leadership

What are Dev's three conditions for someone to become a fantastic leader?

They must be incredibly self-aware, know how to recruit well, and know how to hold people accountable.


← Back to Learning Log