Why Entrepreneurs Don’t Seek Help
I’ve written two startup advice posts a week since January 2019, all in an effort to help make more and better entrepreneurs. That’s over 250 posts, close to half-a-million words, on concrete concepts that are valuable to both experienced and inexperienced founders.
These posts are (for the most part) free, and I’ve received hundreds of emails and other communications letting me know that the posts made a difference. It’s why I do it. But let’s face it. None of those posts contained magic words to turn a garage-based startup into a unicorn. I know this.
I’m also a formal startup advisor, and I get paid a lot to relay the experience I’ve gained founding or growing over a dozen startups and advising dozens more. That formal advising has helped a handful of startups reach a place exponentially higher than they would have otherwise.
But what about all the rest of those startups?
Those 250+ blog posts help a lot of startups a little bit. And those $250/hr sessions help a select few startups quite a lot.
It’s always confounded me that there is very little help available in the middle, for those startups that need more than a blog post on a specific topic, but don’t need a part-time CXO constantly pushing them to reach their potential.
About 10 years ago, I decided to solve that problem and I created Teaching Startup to do so. Over the decade, it has evolved and crashed and was reborn a couple times with a new focus and a new model. This is what happens when you try to solve complex problems with multiple unique angles and edges. You fail a lot.
The most recent iteration of Teaching Startup has stuck. As I move into the second year with this model — with tons of paying customers who are truly finding value in it— I think I’m finally onto the solution.
The model will continue to flex and shift as all new solutions do, but with 10 years of trial-and-error and a full year of success in my rearview, I think I have a pretty good idea of the scope of the problem. It begins with this question:
Why don’t entrepreneurs seek more help?
It’s hard to find a good resource
Try looking for startup advice on the Internet. It’s disheartening. Sure, you can read a ton of blog posts, but to find the exact topic you need addressed and the right solution for your unique business can be maddening.
Furthermore, even when you find a piece that does address your problem, the intent of the piece is usually not to solve that problem. Instead, the intent of the piece is to get a lot of people to read that piece. No judgment, I do this too, but the results can be so broad trying to solve the problem for everyone that it ends up solving the problem for no one.
I try to be actionable, insightful, and honest. That does really well with a niche audience of serious entrepreneurs, but it doesn’t trend, if you know what I mean. So Teaching Startup goes the other way — it pushes more actionable, more insightful, and drop-dead honest answers — eyeballs and likes be damned, let’s get right to the value.
They don’t know what to ask
“Can I pick your brain?” — This doesn’t work. Don’t do it.
Before Teaching Startup, I founded ExitEvent, which was a network, a resource, and a marketplace for entrepreneurs. ExitEvent did very well, and I sold it in 2013. One of the key components of ExitEvent was something called the Startup Social, where entrepreneurs from all over the region would gather in one place and just freaking talk to each other. That was the goal, that’s what it did.
This turned out to be a great marketing engine for ExitEvent, but I also learned a great lesson from those events. Entrepreneurs would gather around as one of them casually asked a question of another more experienced entrepreneur and that entrepreneur answered the question. Those entrepreneurs were just as interested in hearing the answers to someone else’s question as they were in hearing answers to their own.
It occurred to me that this is how you learn the right questions to ask — hearing other people ask their own questions and getting the proper answers. So this is the model that Teaching Startup is built on.
The advice is too generic
There are two kinds of advice that make me cringe every time I hear them.
Work harder. There is no problem in this world that can be solved by doing the same thing harder and expecting a different result. You can’t outwork your competition. If you give 110%, they’ll give 120%, because those metrics are imaginary in the first place.
Cliche. I like cliches. I also like metaphors, anecdotes, and examples. But when these are the sole answer to a direct problem it gets my blood up. It’s just a trick for the advisor to sound smart and hope the advisee pulls the right answer out the interpretation, of which there are many, which is why it became a cliche in the first place.
The best advice is not “Here’s what you should do,” it’s “Here’s what I did.” So this is also a foundational element of Teaching Startup.
When you truly add value to something, you can put a number on what that’s worth. If I can add 10x value to any endeavor, I’m worth a lot to that endeavor. If I can’t add that kind of value, I can give away my skills pretty cheap because it won’t matter.
But cost isn’t the problem. The problem is the status quo.
For decades, we’ve been told that the way to learn, outside of first-hand experience, is either through book-learning or instructor-led learning. This is actually true, but with all this technology we have in place now, all this automation and on-demand infrastructure — why are the only options for startup help blog posts or $250/hr advisor sessions?
(And yes, you can make those sessions cheaper or substitute equity or whatever you want. Again, you get what you pay for.)
I’m an entrepreneur myself. All that tech and automation and on-demand stuff is in my wheelhouse. Using those concepts, I’ve made Teaching Startup $10 a month, or less than one percent of the cost of a traditional advisor who is worth their time. It does most of the job without all of the fluff.
Not every entrepreneur needs a costly part-time or full-time in-house expert. Teaching Startup supports that wide and fertile middle ground, to make more and better entrepreneurs.
Try it yourself for free and see if it’s the kind of thing that can help you. You can go light, no credit card needed, and just get the weekly newsletter, or add a credit card for a full 30-day trial of the web-based archive and cancel any time. Use invite code MIDDLE and you’ll get your first month after the free trial for $5. Like I said, after that it’s $10 a month.