How does someone evolve into an entrepreneur? A founder? a CEO?
This week in the Teaching Startup Q&A Newsletter, some of our veteran entrepreneurs answered that very question.
To be 100% honest, this is one of the questions I get all the time and it’s silly and kind of painful but I understand why it gets asked a lot.
How does one become an entrepreneur? The short answer?
First, you have to call yourself an entrepreneur, over and over again. That’s the silly part.
Second, you literally have to do nothing. Except start, build, and grow a business. That’s the painful part.
I mean, the answer is right there in the question.
Or is it?
Snake Oil and SaaS Startups
Not all “entrepreneurs” are “entrepreneurs.”
I’ll be the first to tell you that entrepreneurship has always had kind of a shady film around it. And that shadiness can be lite shadiness like the fake-it-until-you-make-it ethos of any legit startup, or it can be the good old-fashioned shadiness of a Billy McFarland.
As an aside, if you haven’t seen the Daniel Tosh “interview” with Billy McFarland on Tosh’s new podcast, I recommend. You can see that snake oil shit just ooze out of Billy and you might empathize with him. Dude just can’t help himself.
So does entrepreneurship just kind of happen? Or is it a goal? Does someone wake up and say to themselves, “I’m going to start the world’s best SaaS company today”?
We did a poll of our membership last week — How did you become an entrepreneur? — and the results are in this weeks issue.
Should you work for a startup first?
I’ve worked full time on over a dozen startups, and I’ve experienced endings across the board from complete disaster to acquisition to IPO.
My first brush with a startup happened because I hated my first job out of college and took a job in the city I wanted to live in without knowing that the company I was going to work for was a startup.
I was the fourth hire, and I got a complete education in starting, building, and growing a business. I would go on to start my first self-founded, self-funded startup four years later.
Was that my plan? No. Was that the optimal path to entrepreneurship?
Ehh…
Again, not a short answer here, but serial entrepreneur Rachel Greenberg tackled the question in this week’s issue with a deep dive you wouldn’t necessarily expect.
Speaking of hustle…
Teaching Startup is for all entrepreneurs from first-timers to old-timers, and in this week’s issue we’ve also got a question from a member looking to capitalize on recent customer success by getting permission to to use their names in marketing materials.
Is this a potential apologize-later-rather-than-ask-permission-first situation?
See? There’s that shadiness angle again.
Is entrepreneurship in decline?
And if so, does any of this really matter?
There’s a lot of talk right now about slammed doors and sealed windows in the startup and investor world. Is this lull part of the natural progression of the macro-entrepreneurship cycle? Or is something deeper at play?
We did a poll in this week’s issue asking just that, and we’ll analyze the results and the broader economic climate next week.
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