
Getting Your Team to Embrace Productive Pessimism
List member Alex from Boston wrote with a leadership challenge many founders face: “You mentioned ‘productive pessimism‘ in planning, and it really resonated. But how do you get your team on
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List member Alex from Boston wrote with a leadership challenge many founders face: “You mentioned ‘productive pessimism‘ in planning, and it really resonated. But how do you get your team on

There’s a collective intake of breath when Shark Tank contestants proclaim that over 80% of their sales come from Amazon. It’s not the good kind of gasp. The sharks recognize what many

Hormel Foods — the company behind SPAM, Skippy peanut butter, and Dinty Moore stew — is using AI to figure out which peppers will make you sweat. And be delighted

Longtime list member Carlos from Miami wrote me about a challenge many premium brands face: “Amazon is driving us to lower our prices to stay competitive with knockoffs, but we’ve built

I once worked with a B2B client whose organizational structure provided me a schooling in how not to operate. Their company wasn’t a unified entity but a collection of competing

The Rolex Submariner costs US $9,150. Not because the ceramics, steel, and mechanisms justify that price. Not because Rolex performed some magical positioning alchemy that convinced customers to value precision timekeeping at

A while ago I came across this product tagline (I paraphrase slightly): “Delivering transformative enablement via cross-platform process optimization.” That’s not the Curse of Knowledge. That’s just vagueness. The Curse of

Sometimes the smartest business decision is giving your worst customer exactly what they want. This goes against every entrepreneurial instinct, right? We’re taught to stand firm on principles, maintain boundaries,

The most valuable people in product work are seldom generalists who know a little about everything. They’re specialists who deeply understand how their expertise connects to business outcomes. Take my

I had one of THOSE calls yesterday. You know the type — where you can practically hear the sad trombone playing in the background as the caller unveils a parade

Yesterday I wrote about the power of becoming your customers’ true favorite. Today, let’s talk about the dark side of that pursuit. Amazing service can accidentally create MONSTER customers —

I know it seems kinda similar, but it’s not. There’s a world of difference between your customer’s “preferred” choice and their true “favorite.” That gap determines whether you compete tooth

Google Ads keeps sabotaging my niche campaigns. Not through bugs or glitches — through deliberate design changes that systematically favor broad, generic advertising over precise, targeted messaging. Here’s what’s happening: I

Kimberly-Clark just dropped a potty training app. Not a potty training guide. Not a tips and tricks PDF. A full-featured mobile application complete with classic Disney characters (as “band leaders”), milestone tracking,

I recently worked with a founder who was giddy with anticipation. “This is gonna BLOW UP,” he told me. “Once influencers and the press see it, they’ll be fighting to

When threats appear, our dog brain takes command. This emotional, instinctual part of our psychology — which I dig into extensively in I Need That — doesn’t carefully weigh options or

My family teases me mercilessly about my restaurant ordering patterns. “Dad, you know there are other things on the menu besides the pad see ew, right?” “Are you physically capable

I have been doing something a little different in planning sessions. Instead of the usual optimistic roadmapping, I open with a bit of an unusual request: “Before we talk timelines,

Remember the great mask and sanitizer gold rush of 2020? Seemingly overnight, everyone from distilleries to clothing manufacturers pivoted to producing pandemic essentials. Car companies made ventilators. Fashion designers crafted

Some strange things are afoot right now in the product world. (And I suppose consequently at the Circle K.) New pressure is squeezing consumer product companies from both sides. Investors

My daughters are more serious gardeners than most adults I know. They’re the youngest ever volunteers at our local botanic park — a position the older one secured entirely through

Ever notice how some movies get panned by critics yet adored by audiences? This gap compelled Seth Godin to write a recent post about Rotten Tomatoes scores. Movies like The Boondock Saints and Greatest Showman landed embarrassing 26%

I just completed my occasional role as print production manager, sending some client brochures and a poster to a trade printer we’ve used for years. While I’ve delegated the majority

Too many times, I’ve seen brilliant products brought down by the very teams that created them. A revolutionary software platform dies as founding partners descend into backstabbing and legal battles.

There’s a saying in marketing: “Right message, right person, right time.” Most product marketers obsess over the first two elements while completely missing the third. Quite truthfully, it’s sometimes the

The most valuable prospect often isn’t a new face. It’s more likely someone who already KNOWS you. Seth Godin captured this perfectly in a recent post: “Marketers face a choice every

I’m facing an interesting marketing challenge with one of my newer clients. We’re launching a device that installs inside a musical instrument — and might never be seen again after

I have been enjoying working with a client and a video team to create an installation video for a new electronic device. As we mapped out each step, two questions

Ever watch a brand try to be “fresh” and feel your entire body physically recoil? I think of Kanye West‘s 2024 Super Bowl ad promoting Yeezy. He shot it on
That familiar bottle of Sprite just morphed into something else. Suddenly, it’s a ticket to exclusive music events, a key to limited fashion drops, and a membership card to a

Yesterday I came across a fascinating article about price pack architecture (PPA) that confirms something I’ve been chirping about for years. Success is often not so much about what you

In my last few emails, I’ve explored the power of timing in marketing — from trigger moments to competitor vulnerability windows. Today I want to focus on one more kind

Product makers live in a fantasy world. In this dreamland, customers spot our amazing new solution and immediately abandon their current provider, gleefully skipping over to our superior offering without

A sharp reader asked an excellent question after my last email about trigger moments: “If you nail the perfect timing, does that mean less exposure is necessary before conversion?” This

My father-in-law is a gifted artist, and among his many mediums became exceptionally adept as a potter. Each piece he created was unique — a one-time expression of creativity, technical

What’s your exit strategy? If that makes you squirm a bit, you’re far from alone. Many product makers pour everything they’ve got into the day-to-day, without lifting their gaze to

Walking through my grocery store a couple days ago, I found myself contemplating the Coca-Cola display. Bottles labeled with names like Jillian, Brian, Summer, and Ahmed lined the cooler shelves. Plenty of

Standing in a grocery store checkout line yesterday, I witnessed a scene familiar to any parent. “Mom, can we have gum?” asked a hopeful child. “No,” replied the mother, continuing

My partner loves her iMac, but finally got tired of waiting for Apple to release a new 27″ model. Fair enough — it’s been years, and the waiting game gets

This Mother’s Day got me reflecting on something in a new way: Moms are THE most effective marketers on the planet. Think about it. Before any of us ever encountered
Let me ask you something: How do you prefer to discover and buy products? Wait. Before you answer, consider a different question: How do you actually end up buying things? The gap between these

I’ve been working on a launch project for a consumer product client with an enviable situation: their product name perfectly encapsulates what it does. It’s rare gold in product marketing.

A few weeks ago, without really meaning to do it, my wife and I embarked on a mission we’ve somehow avoided for decades: buying a complete cookware set. Until now,

Hasn’t it sucked how you couldn’t buy a Kindle book directly through your iPhone app? That finally changed this week. Yesterday Amazon announced a new “Get Book” button in its

Yesterday marked the end of an era. Skype — the service that introduced millions to video calling — officially went dark after 22 years. It was one of the first

A post by neuroscientist and podcaster Andrew Huberman has been living in my head for weeks. It challenges everything we thought we knew about habit formation. Remember that old wisdom about “it
May the Fourth be with you! (I don’t care. It’s Star Wars Day, it’s my email, and I’m sayin’ it.) The first time I saw Obi-Wan Kenobi wave his hand

I’m in the middle of a classic startup pricing standoff. A client has developed an impressive new tech product that solves a widespread problem. The solution works beautifully, but now

Arielle — a sharp early-stage founder in Montreal and longtime list member — emailed after reading my series on biases: “I’ve read a lot about loss aversion and other status

Mayday, Mayday! I’ve got some thoughts to help your month get off to a fantastic start, even if you’ve been losing sleep over the trade war situation. The latest NielsenIQ