A Smart Bear: On Strategy

This eight-step process brought WP Engine from an idea to a Unicorn. While there are other roads to Product/Market Fit, consider copying some of these ideas. —December 2023 | 6,500 words.

Many startups fail despite identifying a real problem and building a product that solves that problem. This explains why, so you can avoid their fate. —April 2023 | 6,800 words.

A startup can beat a large, successful incumbent, if it does things the incumbent can not or will not do. Here are those things. —February 2024 | 4,800 words.

We dramatically, repeatedly fail to predict the future. Does that mean “strategy” is senseless? No, it means you need these techniques to navigate a volatile world. —March 2023 | 4,900 words.

Why do startups typically fail? It turns out that “avoiding those things” is already a plan for success. —March 2024 | 4,000 words.

This fresh take on “Willingness-to-Pay” analyzes three types of customer motivation, leading to superior strategies for growth that also better the world. —May 2023 | 4,000 words.

The typical dynamics between startups and incumbents do not apply in AI as they did in previous technology revolutions like mobile and the Internet. Ignore this at your peril. —March 2024 | 1,900 words.

This simple method positions your product to be more valuable, especially against competitors who aim to disrupt you, or you them. —June 2023 | 3,800 words.

The difference between “low prices” as a race to the bottom or as a success story (like Amazon, Costco, IKEA, Vanguard) is in leveraging intentional weaknesses. —April 2025 | 2,600 words.

Most so-called “strategies” are vague, wishful thinking, written once and never seen again. Don’t do that. These are the characteristics of great strategy. —August 2023 | 5,900 words.

Leveraging strengths – not “fixing weaknesses” – is how to win. Better when differentiated. Best when durable. Here’s how to create leverage. —June 2023 | 3,300 words.

Not “enabling constraints”, not “weaknesses”, not even “strengths”. The concept of a “Pivot Point” grapples with the same reality, but more constructive and useful. —September 2024 | 4,400 words.

Why do smart, driven founders fail, despite having great ideas and execution? This model offers an answer, and a path to increase the chance of success. —February 2025 | 2,800 words.

Industries commoditize over time, delivering similar products at similar prices resulting in low profit. Moats are the antidote; your strategy must create some. —May 2022 | 1,800 words.

On average, you’re halfway to your final destination. How, then, do we not only double from here, but 10x? —November 2014 | 1,100 words.

How to tell the difference between a truly great startup idea, and people saying “Sure, sounds good” when they really mean “No, I’m not buying.” —June 2012 | 1,500 words.

An objectively “worse” strategy can win, if it leverages something unique or unexpected. Startups can use this concept to beat incumbents. —August 2023 | 1,000 words.

We invented this strategic exercise at WP Engine – engaging both Marketing and Product, generating actions for both sides that make products more desirable and competitive. —June 2022 | 3,200 words.

Traditional fairytale structure fits naturally in our brains, and thus can guide strategic problem-analysis, and a plan that everyone understands. —November 2023 | 4,000 words.

Luck always plays a role in startups, but there are ways to better capture upside and mitigate downside. —October 2019 | 800 words.

I remember “disruptive” when it was called a “paradigm shift.” You should be worrying more about making something people want to buy, and less about disrupting everything. —April 2010 | 1,600 words.

What if your company could have only one single advantage over the competition? This exercise will make your positioning and strategy stronger. —March 2010 | 1,900 words.