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.

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.

Most startup advice I see follows the same path. Get an idea, form a team, write a business model, spreadsheet your financials, make a deck, raise money, track your KPIs, exit, repeat. I’d swear most of this stuff is written by people who haven’t done anything more than read the same thing someone else wrote:

6 secrets to a winning pitch deck

The one mistake every entrepreneur makes

Fail-proof your startup with three simple exercises

Silicon Valley’s smartest founders swear by this one interview question

I want to stab myself in the brain when I read titles like these. No offense to anyone who has ever written a bad post because I’ve written some terrible posts too. But I can state empirically, based on the vast number of entrepreneurs who have written in to me, this is the bulk of what they’re reading.

That shit’s gotta stop.

I have a doc where I keep all my topic ideas and notes that turn into posts. There are three words at the top: Actionable, Insightful, Honest.

So what I write has to be true, it has to make you think, it has to help you act.

I also get a number of questions as to why I’m giving this advice away. Those are super flattering but I also always have in the back of my head that quote about what free advice is worth.

The answer is a little complicated. There’s some personal math.

First of all, if you’re familiar with Medium, it’s not free. But Medium is the first platform I’ve ever seen that balances free vs. paid, quality vs. reach, and personal vs. business. Believe me, I know. My first sole-founder startup was a Medium-like platform called Intrepid Media, which ran for 12 years and was successful but never did Medium volume. Also, the people at Medium are awesome, every single one. That helps too.

I actually don’t believe in giving anything away for free in a business context. It devalues what you’re offering. That said, this isn’t all business. There’s a sense of mission that I’m on, stated above, and this is the stuff that’s going to get you in the door.

I’m also 100% aware of what giving this stuff to you does for me. That goes without saying, and I’ve been paid back many times over.

Also, it’s fun. That’s very valuable to me.

There is just a little bit of magic to this. That’s this: Usually I can sit down and write a post in 30-45 minutes. The catch is, it has to be something worth writing about, and it has to be pure. If I’m trying to parse meaning or make it seem more intellectual than it is or make myself seem more lofty than I am, it’s not going to work.

I also get a few false starts. Sometimes I’ll get three-quarters of a way through a post and realize it’s not actionable, it’s not insightful, it’s not honest. If I get even a twinge of that feeling, I immediately delete the post before I can do any more damage. That sucks, but it’s worth it.

I’m not a writer. I’m not trained in blog posting. You’re not seeing the results of a course in content marketing. In fact, the secret sauce is it’s the exact opposite of all of those.

I’m not a writer but I’m a pretty good communicator. I’ve got zero journalism or media background so I don’t know when I’m doing the wrong thing. And you all read this stuff because it isn’t content marketing. You all can tell the difference. At least one of you tells me so every day.

All I have to do is answer a question, reach into my past, whether that was yesterday or 20 years ago, and grab the answer and write about it. I have to be working on a startup — not funding one, not supporting one, not marketing one — but advising startups helps too because I get a lot of different takes on the same strategies.

And I have to think about this like it’s a startup, because it’s what I do. If you saw the data I keep on everything from hard numbers vs. dollars to what kind of content and how it’s written works, you’d laugh at me. But it’s the same thing I do when I’m figuring out how to wash everyone’s car while they’re at work, or teach computers how to write sports articles, or get service providers to pay me for double-blind access to startups who need them.

So yeah, there’s a bigger picture, definitely, and I’m starting to see the shape of that picture. If I can do something that’s good for others and balance it in a way that it doesn’t suffocate under the weight of its own altruism or capitalism, then that’s exactly what I set out to do.

You are awesome, and worth it, so I continue.

Hey! If you found this post actionable or insightful, please consider signing up for my weekly newsletter at joeprocopio.com so you don’t miss any new posts. It’s short and to the point.

I’m a multi-exit, multi-failure entrepreneur. Sold ExitEvent. Building TeachingStartup.com & GetSpiffy. Former Automated Insights. More info at joeprocopio.com

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