Planning should take up no more than 10% of the execution time period. If you're planning for a quarter, your planning period should be slightly less than nine days.

Hypergrowth companies compress what takes others 5–10 years into months. That means you need to keep hiring leaders who've already seen the next stage of growth — because it'll arrive before you're ready.

Notion's ambassador program started with just 20 people in 2019 — the 20 most vocal users they could find on Twitter. They grew it slowly, inducting ~20 new people per month to preserve community quality.

At Ramp, our culture is velocity. It shapes every process and team ritual. It's how we develop our people. It's our solution to nearly every problem.

The Aladdin & Genie rule: If you tell the Genie 'make me taller,' he makes you 13 feet tall. AI doesn't know what you mean when you say 'you know what I mean.' Be specific. Provide references. Provide context.

If you can leave a system alone for a long time without it hurting your business, ask yourself: is it actually worth rewriting at all? Rewrite if you can't add what you need. Don't rewrite because the engineers find it annoying.

Ask your leaders what they want before you build strategy. It's amazing how few people do this. Senior leaders welcome it — it gets their creative juices going. And it's not a sign of weakness. It's a sign of strength and humility.

We have more than 15,000 customers who have deployed agents on Azure. The number of agents actually running? Millions.

The Curiosity Loop: pick a specific question, curate the right people (subject matter experts + people who know you), make the ask lightweight, and close the loop by thanking them. It's user research for your life.

For the vast majority of people, they probably do not need a coach. If you're thinking about getting one, first ask: have you explored mentors, courses, communities, or a curiosity loop? A coach is often not the best option.

You don't have a choice. AI is going to disrupt every category in the most aggressive, violent ways. The question isn't whether to get in. The question is whether you're willing to pay the price to actually be competitive — or whether you're going to sprinkle some AI on top and call it a strategy.

Stop trying to force product-market fit. If it's extremely difficult to sell the marginal customer, you won't build a huge business. What you need is the customer that's surprisingly easy to sell — that's the signal.

Crazy Big Goals work because they make you feel completely inadequate. And that feeling makes you work hard enough to will them into existence. A reasonable goal you can hit easily doesn't produce the same obsession. Set goals that scare you.

Hesitation is the most destructive thing a CEO can do. Both options are bad. That's the point. The only value you ever add as a leader is making a decision most people don't like. If everyone agrees, you added nothing. You need to run toward the pain.

Conflict-avoidant, feedback-avoidant cultures degrade the talent bar. They just do. Because expectations are not stated and you're not holding accountability. And I do not think that's kind.

A PM's most important job isn't coming up with ideas — it's owning the WHY. When everyone understands why they're doing something, designers and engineers can make great local decisions without you. That's the only way to scale.

Good strategy is an answer to a specific challenge — not a list of goals. Start annual planning by identifying the most important challenges, then build strategy against those.

Procurement can kill your deal by redirecting you to an existing vendor. If your product doesn't feel clearly different — just 'slightly better' — they'll tell the buyer to use what they already have in the system.

"You shouldn't have to rise into management to increase your compensation. You're equally valuable as a domain expert." — Tal Raviv, Senior IC PM

The things people think will improve AI apps: staying updated on AI news, adopting the newest agentic framework, picking the best vector database. The things that actually improve AI apps: talking to users, better data preparation, better prompts, optimizing the workflow.

Investment and job postings in web3 both grew by more than 400% in 2021. The opportunity for product managers who make the leap is massive — but the role looks almost nothing like web2 PM.

I think the critical voice in your head is always wrong. Not sometimes wrong — always. It's not logical, it's not thoughtful, and it's usually abusive. It sounds like a five-year-old having a temper tantrum.

The most asked question I get: "How do I keep up with all the latest AI news?" My answer: Why? Why do you need to? If you talk to your users, look at your feedback data, and fix your prompts — you'll improve your product 10x more than any model release will.

When evaluating a new distribution platform to bet on: (1) retention + depth of engagement, (2) user quality and monetizability, (3) the value exchange they're offering developers, (4) pure scale. Then immediately plan your exit before the platform closes.

Every six months or so, can you back up and honestly ask yourself: am I proud of this? Is this representative of my best work given the circumstances? Or am I just trying to get through the day?

We went from 4 months to build one column type to 30 columns in a month and a half. The key: we stopped and defined what a column actually *is*, built shared infrastructure for it, then ran a hackathon where each dev built one column in a single day.

We went public with $2M in trailing 12-month revenue at 18 months old. The Wall Street Journal called it insane. BusinessWeek called it "The IPO from Hell." The alternative was going bankrupt. Look at how many CEOs hesitated in that moment. Most of them are gone.

Tarpit ideas are uniquely dangerous because they don't look bad — they look great. You get validation, positive feedback, even early users. That's what makes them traps.

Tokens are a terrible unit for pricing AI. It's like measuring engineer productivity by lines of code written. An Apple engineer famously submitted a negative number after a big refactoring — his way of saying the metric was idiotic. Outcomes are what matter.

Product-led growth is really data-led growth. You give away your free product in exchange for distribution AND insights into how users use it. Without data, you're flying blind.

The most successful people I've worked with aren't the ones who had charmed careers with no failures. They're the ones who turned stumbling blocks into stepping stones — who got hard feedback and came back stronger.

Every designer at Basecamp codes. Not just HTML — running the app locally, going into the view to make it look the way they want. So where's the wall between design and engineering? Those moments of disappointment when the engineer tells you no simply don't exist.

We're in an idea crisis. AI gives you tools to build anything from scratch — design, code, websites. But when companies run hackathons, people don't know what to build. Ultra-specialization has killed big-picture thinking.

The cycles are getting shorter and shorter. You have less time to ride each new platform before it closes. Whatever window existed for Facebook or Google, the next one will be smaller.

I believe AGI undersells what we're collectively building. We already have sparks of super intelligence. When v0 knows how to draw a dashed line accounting for the curvature of the earth — that's just superhuman.

Atlassian spent 2–3x more on R&D than comparable companies — and almost nothing on sales prospecting. They took all the money they would've spent on sales and plowed it into product. That ratio held even after IPO.

The "local CEO" model: product owners at Revolut are end-to-end responsible for their product, their business metrics, and their customers. Engineers, designers, and analysts report to them. It's not a scrum title — it's actual ownership.

Life is more fun when you're in your gifts. But it's a process of continually tuning in to where your spark is — and actively protecting it. You can always do more tuning, no matter how successful you are.

Every founder naturally defaults to their superpower as the solution to every problem. Engineer? It's an engineering fix. Designer? Time for a redesign. BD person? A partnership will save us. If your solution matches your background, it's at least 30% likely you chose it for comfort, not truth.

Opendoor's edge over Zillow isn't just product — it's vertical integration. You have to be great at pricing, product, operations, risk, and capital markets simultaneously. That's in Opendoor's DNA from day one. You can't bolt it on.

"Negotiation is the art of letting the other side have your way." —Chris Voss

"You don't make people great. You find people who make you great, who you learn from — not the other way around." The job isn't to develop your CFO into a CFO. The job is to find the world's best CFO and get leverage from them.

The opposite of play isn't work — it's fear. And I realized that's what I was seeing in my team. That's why the ideas were getting more incremental.

Every time I have a guest I think will move the metrics, it doesn't. Every time I interview someone nobody's heard of, I get emails saying it was the best episode yet. Stop chasing what you think will perform.

The two checkpoints for product-market fit: (1) organic growth — are people telling others without you doing anything? (2) willingness to pay. If you pass both, you have PMF in at least a pocket of the market.

Your strategy doesn't have to be perfect. Your plan will change as you learn new information, but starting with a strategy helps you make better moves now.

Google is crawling the web and your site through links. And if you don't have links, then Google doesn't have paths to find all of your pages.

Snickers competes with protein shakes and sandwiches. Milky Way competes with wine, brownies, and a run. Your real competitive set comes from the customer's context — not your product category.

Writing externally and gaining external momentum was a better way to influence what was happening internally at Shopify than trying to get attention inside the company directly.

A marketplace business never starts as a marketplace business. The biggest failure mode I see is founders thinking too much about being a marketplace before they actually are one. When you start, you don't have scaled liquidity. Stop pretending you do.