A Smart Bear: On Uncertainty

Reflecting on selling Smart Bear in 2007, offering insights for entrepreneurs facing similar decisions. —October 2009 | 1,600 words.

How do you know when to stop, versus when to push through? You don’t, not even in hindsight. But these guiding questions can help. —March 2024 | 1,200 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.

Most high-performing people experience Impostor Syndrome. I did too. When you understand the cause, you can defeat it. —January 2010 | 1,800 words.

Identifying useful frameworks for companies, strategy, markets, and organizations, instead of those that just look pretty in PowerPoint. —March 2025 | 1,900 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.

Why “expected value” doesn’t work; here’s a better framework for making long-term investments in your career, startup, and life. —February 2024 | 2,700 words.

Brittleness is when the company fails because just one component breaks. Learn some strategies for fixing Brittle Points. —December 2024 | 1,700 words.

Half of your “successful” A/B tests are false-positives. This is why, and how to fix it. —November 2024 | 2,000 words.

Discover how to leverage the wisdom of the crowds, but also when to avoid it, as it can easily lead you astray. —January 2009 | 1,100 words.

Don’t use phrases like “unlikely” or “almost certainly.” Here’s real-world data showing why not, and what to do instead. —July 2023 | 1,000 words.

“You’re so lucky.” That’s true. There’s also decades of sacrifice, emotional turmoil, long hours, perseverance. So… is it lucky? —March 2009 | 1,100 words.

Some of the most enticing, important metrics are impossible to measure, even after the fact. Here’s how to identify and avoid this trap. —October 2023 | 1,800 words.

Language shapes our perception of setbacks. Use words other than “failure” to describe situations and to suggest the next step. —September 2023 | 800 words.

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

How do you assess forecasts, when the forecast is only a probability? It’s not just about accuracy. Let’s dive into the math. —June 2016 | 2,100 words.

The LTV metric overcomplicates and misleads. Learn why you should use other SaaS metrics instead. —October 2013 | 1,100 words.

Applying Pascal’s Wager: Humility wins, arrogance loses. —July 2012 | 900 words.

We humans are terrible at discerning patterns from randomness, and in marketing data we unwittingly find “insights” that are actually noise. Here’s how to fix that. —June 2010 | 1,500 words.