How to build sustainable businesses


Seen a few friends do these (@patio11 and @sol_orwell most notably), so I’m gonna try too!

I’ll reply to this tweet with one-opinion-per-like (up to 100) on the topic of creating sustainable businesses.

8. To avoid over engineering (and wasting time), try flintstoning everything before you build big fancy systems and automations.

9. I'm amazed by how many people who start a business either

A) build a fancy spreadsheet that massively overestimates their income potential cuz all of the numbers are made up, or

B) never do ANY math to reverse-engineer income goals into project and rate goals

F, this is harder than I thought it would be! 😅 gonna take a break but I’ll keep going so keep liking that top tweet y’all.

13. Investors and investment is the most complicated financial device that exists.

Start simple: use every lever you have to earn money the old fashioned way, and then use that money to stair-step your way to the next earning level.

aka learn how to invest in YOURSELF, first

20. People don’t pay you because they like you.

They pay you because you generate some kind of economic impact or upside elsewhere in a system that matters to them.

If you learn how that system works, you can figure out how to make more money.

21. Another recurring problem I see around money psychology is acting as though all income is equal.

Yes, all money spends (roughly) the same and when you have bills to pay it feels wrong to turn down work.

But not all money helps you achieve your biz goals in the same way.

28. Things that attract crappy customers (eg demanding, flaky, short term thinkers) include:

- selling to vague audiences - selling in marketplaces - selling “quick fixes” - pricing too low

40. Before you ask “what can I do to make more money” try asking “who can I reach that has money to spend?”

Try to name specific people/biz’s instead of broad categories.

Treat that like a brainstorm except instead of brainstorming ideas you’re brainstorming customers.

44. Where you SHOULD treat your business like a job is around discipline and consistency.

E.g. if you regularly didn’t work because you “didn’t feel like it” at a job, do you think you’d have that job for long? No, you’d be fired.

Treat the work you own with the same respect.

56. If you want people to value your time differently, you need to position your time as something *other* than time.

E.g. as a lever of knowledge or effort

This is counterintuitive and unobvious especially when you've been trained for corporate jobs.

63. The longer you’re in an industry, "expertise" can become a liability if you can't tell the difference between feeling right and being right.

This only way I’ve found to overcome this is to recognize your own snap decisions and question them.

Trust, but verify, for self.

84. If you are looking for your first clients or customers, start by asking yourself:

Where do they go when they have questions or need help? What resources do they trust? What communities do they belong to?

Then, go there.

But don’t go there to sell.

85. Marketers and sales people typically ruin these sacred spaces that your potential customers rely on for trusted support and advice.

So, uh, don’t do that. Don’t seek to extract value (eg talking about your stuff, link to your content, etc.)

Earn trust by being helpful.

87. Believe it or not, this approach of ruthless generosity scales extremely well. Here’s how I do it as an individual.

I’m amazed that more companies don’t deploy this at scale. The closest I’ve seen is developer-focused tech companies doing dev rel.

93. The two best scenarios for a first full time hire:

- a specialist to “own” and improve a specific part of the business that is extremely high value, freeing you up to work on other parts of the biz

- a reliable, adaptable junior who learns quickly and can become your #2

96. Weirdly, these last 5 are hard but for a different reason than the first 10!

Now, the arbitrary ending feels like there’s pressure to end a certain way...

This is both true, and meta-commentary on the pressure people out on themselves to exit a business a certain way. 👀

99. The most likely thing to kill your business, is you.

That also means the most likely causes of failure are 100% in your control.

100. People ask me all the time “do you really still enjoy running @indyhall 13 years in?” Same with @stackingbricks in year 9.


The “same” business doesn’t stay the same, so I’m still constantly learning and growing.

That’s why the long game is my favorite game.