Drawing on 25 years since starting his first business, Dan Bowyer gives three reasons entrepreneurship is tough: founders must master many roles, the real lessons only land through painful mistakes, and the job is lonely.
- Knowing an industry is not the same as knowing how to build a business in it, and founders need a grip on most of the roughly 20 roles in any business.
- The important lessons usually arrive through painful mistakes; Dan once took down multiple email servers for days with a single marketing click.
- Founding is lonely: founders answer to more people than in a corporate job and never quite feel they have arrived.
- Dan says how startups start up has not really changed over 25 years, even though the industry and technology have.
A little reflection on why entrepreneurship is tough.
It breaks down to 3 core reasons IMO…
I started my first business 25 years ago, it took me 3 years to start, I got everything wrong and it took me 3 years to ‘get it’ (“beautiful lessons”, as my coach used to tell me). A core early learning was that it was going to be a never ending conundrum wrapped in an enigma and that’s ok.
Entrepreneurship is tough.
BUT…
…in that 4th year things started to slot together.
I was over the oh f**k hump.
Now I invest in people who are at the stage I was at 25 years ago, but they’re smarter, more energetic and mostly come with less baggage.
Brilliant – because they need to be smart enough to ‘get it’, and dumb enough to try.
Looking at these wonderful individuals now, and looking back at how I was then, so many aspects mirror.
Nothing has really changed in how startups start up, even though the whole industry, how it’s viewed, and the tech has all moved on significantly.
However, all of the important crunchy aspects are timeless and universal.
It is still very much the case that entrepreneurship is tough, but here are the three core reasons I think front and centre:
* Firstly, just because you know about selling houses, that doesn’t mean you know about building a business that sells houses. They are completely different skillsets and the latter is even more of a beast to pin down.
There are around 20 roles in any business anywhere in the world, and as a founder you have to have a solid grip on most of them to survive. Painful. You’ll be sh*t at some, ok at others, while the rest you’ll shine at. Keep learning.
* Secondly, every important lesson you really need to get will feel like a punch in the face because you flat out will not get it until it takes your eye out. Learning smart new stuff is hard and it only really comes in time-sucking jaggedy punchy packages.
You can’t learn from the good stuff. It doesn’t create meaningful change. And often you have to f*ck up to truly get it. My goodness mine make me wince. I once took down multiple email servers for days with a simple marketing click of a button.
* Finally, it’s lonely. As a founder you’re top of the tree with more clients and hands out in your direction than when you worked in corporate. You think you’re the boss but you have more bosses now than you’ll ever have. And worst to boot, you’ll never feel like you got there. One hump just leads to the next and the next – and none are the fun type. As Prince once said, “I’ve been to the top of the mountain and there’s nothing there”.
All I can say is that it’s a fascinating personal and work experience. Drop any expectations and go for a ride. It’s once-in-a-lifetime stuff where you will experience many things most will not.
Enjoy every day like it’s a new adventure, turn everything into a learning project, do good, share honestly and openly while sucking up every moment with relish.
There is no good or bad.
There is no right or wrong.
It’s all a trip!
… Dan
If you’re finding entrepreneurship especially tough, have a read through SuperSeed’s Playbook. We’ve compiled some really useful lessons and tips for startup founders.
Frequently Asked Questions
Why is entrepreneurship so hard?
Dan Bowyer gives three reasons: founders need skills across many roles, the key lessons are learned through painful mistakes, and being at the top of a company is lonely, with more bosses than ever.
How should founders approach the difficulty of running a startup?
Dan suggests dropping expectations, treating every day as a new adventure and every setback as a learning project, and sharing honestly and openly along the way.