What helps someone be open to being wrong? Curiosity. If you have it, it's pretty obvious even in casual conversation, so you can also ID it in people. Adopt it yourself, to be smarter. And hire accordingly.

“Fire fast.” Yes; if firing is necessary, dragging it out is worse -- for that person, the team, and yourself. But, if you’re hiring and firing fast a lot, that means you’re bad at hiring, and you 𝘩𝘢𝘷𝘦 to fix it. You’re punishing innocent people by hiring and firing.

If you despise a marketing channel that your customers love, that's a red flag. Either you're the wrong person to run this business, or you need to partner with someone who's great at that channel.

Is it better to be an engineer and learn marketing, or be a marketer and learn to code? Is it better to be either and find a co-founder who is the other? Or is the grass always greener, so any path to “both” is a fine one?

You can’t know what advice to take, if you don’t have your own intellectual house in order. Once you do, you can find things that are compatible with “who you are,” but help you grow in directions you know you need to. My view on that:

All outliers look different. That's part of what makes them outliers. So, you can start from anywhere, and do almost anything, so long as it's internally-consistent. Just remember, early on, things-that-will-fail look awfully similar to crazy-ideas-that-are-brillant.

It’s not just “confidence.” If you’re confident you have all the answers, I’m not confident you’ll be successful. (1/2)

What's right for you, your brand, your customers, your culture, your goals with the business and for yourself, are unlikely to all be identical to some competitor, especially one that is 10x older and 1000x larger.

Luck plays a larger role than many successful people admit. But also, when a successful person climbed out of a tough starting position, it wasn’t only random. Hard work is required, and you should be proud of it, even when luck helped too.

Tech support isn't just about troubleshooting - it's the face of your company. It's your brand, your positioning, and when done right, it's sales. Elevate its status accordingly.

“Run a business like science: experiments, seeking the truth!” Yes, over a time horizon of decades, that’s how science works. Over five years, it’s rife with bias, holding on to outdated beliefs, not wanting to be wrong. This is the human condition. Still, try.

What makes an entrepreneur sell their 'baby'? Financial freedom and ego are good reasons. Sometimes sticking around isn’t fulfilling either. Catch-22, but in that case, take the money?

A common “scale” strategy is “increasing waves.” Start with 1-10. Observe and tweak. Then 100. Observe and tweak. Then more, etc.. At scale, there’s no such thing as “deploy it now.”

Want people to love your brand? People love people, not companies. What if you tried honesty and your own personality? Some will hate it… but some will love you 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 of it. More:

If you had a strategy and it didn’t work, that’s a shame, but it’s the game we play. If you never had a strategy, and just made random things, and it didn’t work… what did you expect? That’s why “throw on the wall as see what sticks” is nonsense.

Are you creating content in order to make a living directly from the content? Or to build a career, using the content as social proof for something else? Or to create a personal reputation? Or for fame / ego? Decide, because each require different techniques.

“Sell into a growing market.” How much growth is that? I would say by $250M or more in additional annual spend, regardless of % growth. Space for everyone to "eat" without having to cannibalize each other for growth.

How do you balance the need for focus with the necessity to experiment in your startup?

1/10,000 times someone gets lucky and gets famous with relative ease. We hear that story, then think "that's how it goes, at least if you're successful." No, that's not how it goes. It’s a grind, and with a product, usually you have to pay to get eyeballs.

When you get more efficient, you could work less, and accomplish the same amount. Or, work the same amount, and accomplish more. Which to do? Depends whether the results should be satisfied (first one) or maximized (second one).

You cannot know what it’s like to try a startup until you try it. It’s like thinking you know what it will be like to have kids. If you want to know, then try it, rather than reading about it.

Market-qualifying question: Will the customer buy 𝘴𝘰𝘮𝘦𝘵𝘩𝘪𝘯𝘨 no matter what? If no, this is a difficult market; you have to create demand. If yes, the questions are: Will it be you? Why? For whom?

Being a founder isn’t “a balance.” It’s everything, all at once.

The “Status Quo Bias” isn't always bad. Stability and consistency foster reliability and trust. In a startup's constant change, some constants give people something to hold onto.

The more you’re attached to your idea (the product, the UX, the feature, the target customer, the market, the competitor, the differentiation, the price, the tech stack, the name, the colors), the less you can notice when it’s wrong. Hold everything lightly.

The secret to doubling productivity isn’t unrealistic daily improvement goals, captured in trite tweets like “get 1% better every day!” It’s about eliminating the slowest tasks. Here’s the math behind that, and how to do it:

On active investing: If it gives you joy to play the ups and downs, then great. If it gives you stress and distracts you from things that create wealth or joy, then you should do something boring that you never think about.

There are many successful startups where the initial idea sounded dumb. And when the initial idea sounded smart. And many failures in both cases too. But if it sounds dumb, it had better be "smart under some assumption that we disagree on."

“That’s just a lifestyle business.” So an AI founder in a Stanford hoodie in a hotel lobby on Sand Hill swaggering about his 10 on 50 pre like the love child of Steve and Elon as he goes bankrupt in 19 months as silently as the fundraise was loud… …isn’t a lifestyle?

ICYMI: Remastered classic article: Sometimes it's your job to fill the screen with joyous win.

ICYMI: Remastered classic article: Often we can and should accept 80% of the benefit if it means 20% of the effort. Customers generally prefer the right features over more features. But sometimes… sometimes we should just do what we think is cool…

Without founder/market fit, this team won't be able to execute. Without product/market fit, this product won’t be purchased. So it’s not “which one” or “it’s a balance.” It’s: Both.

Potential customers will ask for ROI calculators. And maybe you should give it to them to tick that box. But that's not how people buy. It needs to generate so much value that the so-called ROI is obvious. Here's how it works:

It’s brave only if you’re scared, yet you do it anyway. Otherwise it’s just “doin’ stuff.” But that means being brave 𝘢𝘭𝘸𝘢𝘺𝘴 means being afraid. And having to overcome. Be brave.

ICYMI: Remastered classic article: This feature took extra effort and was completely unnecessary. But it was endearing--an important attribute not easily captured with metrics and spreadsheets. Not every important thing is a number.

You know that decision / conversation / action that your dreading, but you already know that once it’s done, you’ll think "what a relief that at least its over?" Do it today. You’ll incur the pain regardless. So why drag out the dread as well?

New startup founders: “Our design and features is so much better than big, slow, dumb companies!” OK, so charge a high price. “Has to be cheap because it doesn’t do much.” Hmm…

Everyone else is screwed up. Most people screw up the same things you screw up. You could read that as an excuse to be screwed up. Or you could read that as evidence that you can become un-screwed up. Don’t let commiseration lead to complacency, but to improvement.

Just republished a classic article! 👇🏾 In the quest for optimization, A/B tests, metrics, and funnels, we’re in danger of losing the fun and value of creative work. Many thanks for spreading the love with ❤️ and 🔁!

When you feel like all the good ideas are taken, remember that humans have felt that way for 250 years, and have always been wrong.

Founders must seek & accept truth: • some of your assertions are wrong • you're not the target customer • the customer wants something else • competitors aren't dumb • high cancellation means you're doing something wrong • that one person has to be fired

Are ideas “cheap”? Only in the sense that love is “cheap”. The value of something is not the amount of money you spent.

Yes, “breaking the rules” with purpose, with upside, with intention, is differentiating and fun and effective. Breaking 𝘴𝘰𝘮𝘦 of the rules does. Breaking 𝘢𝘭𝘭 of the rules is chaos and no one can follow you.

Practicing your sales pitch is excellent. (Raising money is a sales pitch too.) But, if done in isolation, you end up with a compact and complete case… that might not resonate with actual customers. Expositions must be iterated with the audience, not only alone.

ICYMI: Remastered classic article: By all the usual arguments for Lean, Agile, and minimalism, I should have used “boogers” instead of making this mini-viewer widget thing. Visual Studio uses boogers to this very day. But everyone loved the mini-viewer.

Wow this article from Roger L Martin on “low-cost strategy” is so good. I wish I had written it!

“We’re the only ones who ___.” “So if I talk to [competitor], they will agree you’re the only ones that ___?” “Well, [tiny detail; no one cares].” Not good enough. At least one thing has to be “yours.” This workshop will help you figure it all out:

Sales can't create urgency, just service it. (In B2B. I see fake urgency in B2C constantly so I assume it works, but I wouldn’t know.)

All the successful businesses I know started with some idea -- an incredible feature, an annoying problem solved, an entertaining thing. But never: I wanted a business, so just I made something random. (Although, it can pivot.)

Lots of examples where selling features works better than benefits (like drills), but also lots of examples the other way around (like self-help). The interseting question is: What scenarios demand which method?