Some interesting thoughts in this thread.

I think there are a few places one can make tradeoffs; would encourage people to not plan on having to make all the tradeoffs at once.

(For similar reasons, try to avoid same time as major life transitions like marriage/parenthood.)
Some potential tradeoffs: tapering work rather than going cold turkey (e.g. switch to 2 days a week contractor at old employer), get a consulting pipeline in bag then juggle (harder than you’d think!), bootstrap to $Xk in nights and weekends (longer than you’d think), etc.
Sequence products differently; infoproduct as first offering greatly decreases your weeks-to-$40k-revenue and will motivate you to get a lot of business infra stood up, most importantly the email/marketing engines.
Would avoid anything which required belt tightening, both because people are bad at it, because it tends to cause stress, and the belt tightening will read to you as productive work but it **is not**.

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More from @patio11

18 Nov
"But how will you compete with AppAmaGooBookSoft's infinite number of engineers to throw at this problem?"
"... Before or after the 5 year head start?"
Shaving context off following:

"If you had an arbitrary amount of talent and money to build a competitor for $PRODUCT, $PRODUCT would be... maybe three years ahead.

The goal, assuming that someone has made this decision today, is for $PRODUCT to be 6 years ahead in three years"
Speaking of which: a good question to have an intuition on is "What set of problems does humanity have insufficient organizational technology to solve, even if it had billions of dollars to throw at them?"
Read 8 tweets
18 Nov
This is, for better or worse, a thing.

A related thing: many Japanese folks will solicitously use first names for foreigners on an assumption this is what they/we want; that is a tough assumption to correct politely.
I try to be pretty solicitous here, but between my inner thoughts and Twitter, I did not spend six years in the salt mines to get first named during a business card exchange. And almost never a -san!

This salaryman is shocked at the state of the new generation.
I still have a deep appreciation for the boss of my boss at my salaryman job, who called me “Patrick” to the entire company during my ceremonial swearing in then paused for a moment, corrected himself, and said: “I apologize, that was clearly inappropriate. McKenzie-san”
Read 4 tweets
13 Nov
Idle thought:

Clearly there should be investment opportunities in, without loss of generality, new Substack writers, including both by the platform and by others.
“I would certainly quit my job to do that but...”

If the thing you are about to say involves either risk or money then that is An Eminently Solvable Problem.
“Here’s $100k. You’re covered for a year. Here’s our business-in-a-box recommendations. Here’s the Slack where we coordinate cross-promotion in the portfolio.

We don’t want a dollar until you make 2X the old job. After that, we’ll take 20% [of the first million a year.]”
Read 4 tweets
13 Nov
An interesting thread, which I do not have very strong opinions on.
The big question of entrepreneurs is whether value occurs at the network level, the provider level(s), the financial institution, the infrastructure layer, the application layer, the brand layer, or the distribution layer.
“That seems like an awful lot of layers.”

Yeah wait until you hear about how much I’m oversimplifying it.
Read 9 tweets
11 Nov
In crypto, a very important question to ask is “What if we’re the marks?”

cryptobriefing.com/behind-shroud-…
Best detail is how they sent X00 Bitcoin to their crypto custody provider and then found out that the person they thought was their AM at the custody provider was actually a fraudster and the Bitcoin was now unrecoverable.
That is an attack vector in real finance, too, and has been for hundreds of years, so sophisticated firms are reasonably careful about checking.
Read 5 tweets
11 Nov
It floors me that with all the AI/ML expertise being deployed on relatively narrow problems, the best productivity suites can do to predict which documents are relevant to your interests is "sort by access_time desc"
How about

"Team members who viewed this Gantt chart also viewed the project plan"
"You comment on 100% of documents with Bitcoin in title. Maybe this one also relevant to your interests."
"A paragraph you wrote copy/pasted to here; it is visible to you; maybe we should flag it."
"You searched, opened this document, and closed it 3 seconds later; probably not what you were looking for so maybe I won't put it in Recent Documents."
"You start every day by checking email and updating your daily action plan. I wonder what doc you will open today."
Read 6 tweets

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