How to make failure sustainable (and career entrepreneurship possible)

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 flagsshipping, 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 fails, the entrepreneur shifts some time back to making enough money that their innovation may continue, uninterrupted.

and should their upside hit, they keep enough aside to treat like future income, using it to sustain their next batch of creations & experiments.

the only lives i’ve ever envied have looked like this.

ps. this post is on hacker news. if you found it worth the time, i’d appreciate any help spreading the love.

[1] guys who risked everything and succeeded are the most dangerous role models. “sink or swim” seems like a great idea from the perspective of those who made it back to shore.

[2] when i say “upside,” i mean that you get a chunk of the action if the project goes really well. owning equity in a startup is upside. the cast of star wars got paid a small percentage of total earnings from the franchise. that’s upside. getting paid a fixed hourly or yearly amount has zero upside.

[3] on this particular point, i don’t care one speck about the disagreement of anyone who is already rich and/or successful.

[4] it’s pretty easy to make a little money on the side, but it’s hard to make a lot. that means an important corollary skill is knowing how to keep your lifestyle costs low.


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