I’ve done nothing for the past 5 years but drive companies out of business.
Through doing so, I’ve learned how to make failure sustainable.
Career entrepreneurship isn’t viable if you’re forced to return to a full-time job after every slip-up.
Upside versus downside
A few years ago, I would have claimed that the definition of an entrepreneur is someone who maximises upside and ignores downside.
But focusing completely on upside just means your startup career is destined to be either brief (first-time failure you can’t recover from) or lucky (first-time success)[1].
Instead, I want as much upside as is feasible while still paying for my life.
That means I would rather work 20 hours of contracts and 20 hours on my startup than 40 hours on my startup, assuming the former is sustainable and the latter is not[3].
I would rather make $X000 a month with a chance for a million, than $0 a month with a chance for a billion.
The two most important skills
First is learning to make enough money to sustain your target lifestyle[4], as efficiently as is possible.
Second is learning to create upside.
Sometimes upside is given to you, like when you join a startup as an early employee or take certain jobs with uncapped bonuses or commissions. But in most cases, you have to create upside yourself.
They grow from planting flags, shipping, and getting out there, supermodel-style. I’ll write more about both in the future (so subscribe, hint hint).
What career entrepreneurship looks like
To my mind, career entrepreneurship looks like someone living well below their means and re-investing that financial freedom in planting the seeds for future opportunities through developing relationships, projects, and themselves.
When one of those seeds takes root (in that it has upside and can sustain the entrepreneur), their whole focus will shift to that project. It’s now the best of both worlds. Projects which become profitable or raise funding are an example of this evolution.
If the project...