A Smart Bear: On Psychology

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.

You’re not profitable if you couldn’t afford someone else to do your job. $1000/mo isn’t profitable. Fix your definition of “profitable,” and build a truly profitable business. —August 2024 | 900 words.

Even at wildly successful startups, the first few years are gut-wrenching, uncertain, on the brink of collapse, where pessimism is realism, and yet optimism is required. —April 2024 | 1,200 words.

Advice from “successful entrepreneurs” might be unreliable due to Survivor Bias. What’s real, and what’s random? —August 2009 | 1,600 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.

Humans have always tried to live forever. Maybe you can, but not in the way you imagine. —September 2024 | 1,300 words.

This admonition recurs in myriad books, frameworks, and topics, across decades of time. When something is so consistent, it must be wisdom. —April 2022 | 1,900 words.

Are you crying in the shower because you can’t handle it anymore? Beyond Impostor Syndrome: Complete melt-down? Well, at least you’re in good company. —February 2011 | 1,700 words.

Beware of advice that tries to change who you are. True wisdom guides you to a better version of yourself. —December 2008 | 2,100 words.

What is it like to reach the pinnacle of success? Is that where you attain happiness and fulfillment? Or are those found right here, right now. —July 2014 | 1,000 words.

No you can’t “have it all.” You can have two things, but not three. —January 2014 | 500 words.

Many founders experience a profound and prolonged sadness after selling their company. But “not selling” might be worse. Maybe my story will help you. —February 2013 | 2,400 words.

Having skipped to the last page of other people’s books, we forget the rest of the journey. And, that we have to take that journey, too. —April 2016 | 500 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.

Comparing yourself to other startups? Focus on yourself instead. —December 2014 | 700 words.

Erica Douglass sold her company for $1M, yet still struggles with self-worth; why driven people can’t escape Impostor Syndrome. —March 2012 | 1,400 words.

We’re told “be yourself” to seek happiness and success. But what if “being yourself” also means striving to become better? What is “yourself?” —August 2011 | 1,600 words.

Tired of being told you need “10,000 hours” before you can call yourself an “expert,” and maybe become a “success?” Maybe you don’t. —February 2010 | 700 words.

Maximizing your chance for success means sacrificing health and family. This sounds controversial, but it’s not just me. —June 2009 | 1,100 words.

Your idea probably sucks, and it doesn’t matter because your business will probably turn out to be something completely different. —December 2008 | 800 words.