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Most experiments fail, but my winners have one surprising thing in common… As I was writing my book , my editor noticed something weird: I included examples of the best hypotheses I’d seen, ones that led to the biggest breakthroughs. “Did you notice these are all negative?” she observed.  They all followed a pattern: “We believe people are not signing up because…” “We believe people are not activating because…” “Is there any reason these are all phrased in the negative?” I

Some products are commodities. Others command huge premiums. The difference isn't features, it’s signal. Expensive products are props in a story the buyer is telling about themself. Companies can charge more when they discover that story and reinforce it. Think about these expensive brands: Patagonia gear  says “I’m active, healthy, outdoorsy, eco-conscious and financially secure…husband material.” Aēsop soap  in the guest bathroom whispers: “Tasteful but not flashy. Details

Five ways to turn a vitamin into a painkiller, with examples from Calm, PayPal, Vanta, Deel and Gong You think your product is a ‘vitamin,’ a 'nice to have.’ Is that a death sentence? Absolutely not! Vanta, Deel, Calm, Gong, and even PayPal all started as nice-to-haves. Now they're painkillers worth billions. Each. They didn’t change their products – they found their customers’ pain, and drew attention to it. Here’s how: Poke at the pain (Calm) :  Meditation is a vitamin for

When founders ask me “how can we break through this plateau?” I tell them this story. This was a marketplace for hiring home-care workers to look after elderly relatives. Growth had been flat for a year, until a researcher noticed something uncomfortable. Their bottleneck was the search results page – people scrolled through candidates, but never clicked on anyone. That's odd. Think about it: Why would you visit a home-carer site, search, and then scroll past dozens of candid

How to inspire your team to do their best work – in 30 seconds I once quit a job that paid $1,600 a day because the founder never thanked me. In my first six months, I accelerated acquisition, lowered CPAs, improved retention and revenue per user. I hired some great people, and even helped them line up financing. Then I sat down for a 1:1 with the CEO and he unloaded: "Matt, you have a problem, we’re not growing nearly fast enough. We need to be growing 2X - 3X faster. Give m

How to find the best marketing strategy for your startup or scale-up? Most strategies start as a list of ideas, a budget and a timeline. But a list is not a strategy, it's the opposite . A strategy involves tradeoffs among multiple good ideas. And that distinction is critical. A list happens when you’re not sure what to do, so you try a bit of everything. People call list items “hygienes” or “best practices” but they're a distraction. Because 90% of your growth comes from 1

Anyone who runs enough A/B tests eventually figures out that t he marketing that pays the bills doesn’t look like marketing . That’s because people have a sixth sense that filters out anything that looks like marketing. Yet each year, we spend a trillion dollars on marketing that doesn't work because it looks like marketing . Here’s what actually works Emails – The ones that convert look like emails, not HTML brochures. Plain text. From a real person . (Your "from" address m

People don't abandon checkouts and free trials because they  forget , they abandon because they  object. Here’s how to win them back. Instead of sending “reminders,” figure out  why they bailed and address the  real objection – Not just in your emails, but at the root cause, before they abandon. How to find the real objections that lead to cart abandonment If you ask Google or ChatGPT, they’ll tell you to offer free shipping and enable guest checkout – but you know it’s no

Most courses don't work. Here's how to really help your team be more effective in 2026 ‘Tis the season to spend your learning budget, so I’ll say it…  Most "learning goals" are bullsh*t. People sign up for a course, watch some videos, feel productive, and nothing changes. They learn facts and frameworks, but they don’t become more effective – which is what they, and you, ultimately want. They need skills like: Communicate succinctly with confidence Become more strategic Influ

AI is destroying jobs and business models, but creating something 100X bigger. This might seem hard to believe, but through the long lens of history, the pattern is obvious. Before the printing press, scribes earned good money copying Bibles by hand. Gutenberg’s press wiped out that industry – but it created a hundred new ones: publishing, subscriptions, advertising, newspapers, pulp fiction, copyright law, textbooks, toner cartridges, and eventually Pokémon cards. Economists

I have a friend who was a “job stacker.” She had three full-time jobs at corporations you've definitely heard of, not competitors – working remotely, using AI to amplify her output. She is exceptionally good at what she does, and survived multiple rounds of layoffs at all three. None of them knew the truth. She found an arbitrage opportunity. Three companies paid her for 40 hours a week, each got high-quality work, none got 40 hours. Time-for-money was never a great model for

I climbed from doing marketing grunt work to GM of an $800 million business when I figured out one thing… Founders and CEOs desperately want to promote you . They'd love nothing more than for you to run pieces of their business, if they believed you could do it well. What I learned from watching "Alex" Early in my career, I started working for a guy we’ll call Alex. He was 28 years old, and running the largest division of a publicly traded software company. I was 27, and I ke