Advice from first time entrepreneurs

I’ve been an entrepreneur for almost 30 years. I’ve founded or co-founded a lot of companies in that time. I’ve taught and mentors hundreds of entrepreneurs in the last decade. I’m a lifelong learner and am constantly finding and reading more advice to make entrepreneurs’ lives easier, including my own.

There is no shortage of startup advice. The trouble is, a lot of this advice comes from highly successful entrepreneurs. Especially those who hit it big on their first startup.

The trouble with their advice? They don’t know why they succeeded. They don’t know why others fail.

Most of the learning on how to create successful startups comes from experiencing or analyzing the failure stories. Far more is learned from failure than success. Step back far enough and it’s obvious why that is true. Failed startups are those with a series of mistakes or hurdles they can’t overcome. Successful startups are those with a series of mistakes or hurdles with just enough good luck and good decisions to keep going. Going until there is a long enough string of good luck to call the company a success.

You have a decision to make. If you have seconds to decide, you go with your gut. If you have minutes, you might take that minute to weigh Plan A with Plan B. If you have weeks you might create a pro-con list to help decide between those two – or even three – options. If you have months, you might take the time to brainstorm for some out-of-the-box options. What most people overlook is that there...

A few months ago I was interviewed on a podcast where the key question was “What is your superpower?” Sounds innocuous and simple, but it was one of those moments to reflect on life and not just provide a truthful answer, but something interesting and thought provoking. My answer was “If only”. What if _____? I’ve been an entrepreneur for over thirty years, founding or co-founding 10 companies. I...

I’m in a reprise mood this season… recently thinking about a blog post from 2015 with a lesson learned in an old movie on how to blow up a dam. A lesson about the expectations when making a big change to the world. The lesson comes from Force 10 from Navarone, starring Harrison Ford and Robert Shaw. This is a movie I first saw on a Sunday afternoon on TV as a pre-teen, and then dozen...

There are so many lessons in startups, startup investing, and technology adoption that come from looking back a few decades. For example, I’m out of the 1970s nostalgic computing rabbit hole, but that journey has subsequently led to reviewing the technological progress of the late 1900s and early 2000s. This week, that was the rise of the RISC-based CPU, which was then obviously going to...

The buzzword of 2024 is “AI” and like social, mobile, cloud, fintech, and blockchain, every startup is claiming to have it and every big startup fundraising is claiming to expand what can be done with it. Or in short, we’ve been here before. A Grand Unified Theory of the AI Hype Cycle does a very good job explaining how this will play out in 13 steps, and how it already played...