Why I’m Giving Free Advice to Entrepreneurs

Last year, around this same time, I committed to writing two startup advice posts a week on Medium. I started on January 2nd, 2019 and this will be the next to last one for the year.

It wasn’t a New Year’s resolution, but it was almost as spontaneous. I’ve been trying to figure out how to help other entrepreneurs for as long as I’ve been an entrepreneur, a span of over 20 years.

I’ve joined (and quit) startup support organizations, I’ve been (and quit being) an angel investor. I advise founders formally and informally. I’ve written for everyone from TechCrunch to the local news outlets, and even a couple books. I founded and then eventually sold a startup network and platform called ExitEvent. I funded and built another company called Teaching Startup.

But I don’t feel like I’ve nailed my thesis yet. So my twice-a-week attack on Medium was sort of me throwing my hands up and just getting startup stuff out of my head.

At the same time I started writing regularly on Medium, I put a link on my website asking entrepreneurs for startup-related issues and questions. I get a lot of questions, and I’m thankful for each and every one of them.

Almost all of the questions that come in have to do with stuff I’ve already been through or am going through, as I’m still working my 12th startup today. But some of the questions, especially from my peers who are also interested in helping other entrepreneurs, usually start with:

Why am I writing free advice posts for entrepreneurs?

How am I writing two a week and not drowning in sameness and bullshit?

I never talk about the process, because talking about the process is boring. But it’s the holiday week and I’m on vacation. The next post will be back on mission, but this is also good for you to know as a foundation for what I have planned for next year.

Why I’m writing the posts

My mission, through every endeavor involving startup advice that I’ve ever tackled, has always been the same. There is not nearly enough actionable, insightful, honest content available to those of us trying to start a company or work for a startup or do startup-type things in a non-startup environment.