So, the subject of the OP is doing a
successful startup.

On that, three of my thoughts are:

First, nearly all first, wild guesses for
a successful startup are doomed to fail.

Why? (A) Nearly no one wants the
product/service, say, the results, even
for free.

(B) Lots of people like the results, but
nearly all of the those people regard the
price as too high.

We can call getting past both (A) and (B)
as finding product-market fit.

(C) Okay, but, still, say, for a battery
with 10 times the currently best in energy
in KWh per kg of weight, we don't know how
to do that. Similarly for some software
that is as intelligent as a human in all
respects.

Second, to have some idea that a project
won't fail due to (A)-(C) or anything else
serious can easily think of, one should
have some good plans and, of course, check
the plans as carefully as possible.

Then we can formulate a

Saying: If you fail to have a good plan,
then you have a good plan to fail.

Lesson One: So, to avoid problems such as
(A)-(C) and to improve chances of success,
IMHO good planning is important.

Third, startups that are successful enough
to make money for venture capitalists
(VCs) and their limited partners (LPs --
the people the VCs get the money from) are
rare.

How do we know this? A VC firm may look
at 1000 unique proposals from
entrepreneurs for each proposal they fund,
and fund 20 proposals for each one that is
very successful and actually makes money
for the VCs and their LPs. So, for such a
success, that VC firm has looked at 20,000
unique proposals.

Yes, if in some year there are a total of
20,000 unique proposals, there are 200
VCs, each proposal is sent to all the 200
VCs, each VC funds one proposal out of
each 1000 they see, then each VC funds 20
proposals and in total there are (20)(200)
= 4000 proposals funded of the 20,000.
But, again, only one in 20 is successful
for only 200 successes out of the 20,000
or 1 in 100.

So, depending on assumptions about the
data, the chance of success from a
proposal is 1 in 20,000 to 1 in 200.

So, in a word, the desired success is
exceptional.

Lesson Two: To have one of the 1 in
20,000 proposals that is successful,
instead of just luck, about the best
approach is to have some good planning.

Is it possible to have some effective
plans? Yes, e.g., there was the first
Xerox photocopying machine, the first
daisy wheel printer, the first good dot
matrix printer, the first good inkjet
printer, the first good laser printer, the
first good program to drive such printers,
the first good spreadsheet program.

Now, let's look at the arguments of the
OP:

"But we have done something in the
ecosystem to encourage this type of
outlandish promotion ... where you feel
like you need to use words like trillion."

Why is the planning for a trillion
necessarily "outlandish"? We know that we
are planning for something exceptional,
and maybe good and careful planning, which
is the kind we want, says that, really, if
we do well and take all the market, then
we do get a company worth $1 T. An
investor would prefer the planning to be
for $1 B or $1 M instead? Okay, if the
company really looks like it could be
worth $1 T, then it is easy enough to cut
down the estimate to something much lower.

"Reality is, that for every thoughtfully
articulated and executed world domination
master plan, most of the biggest and
impactful companies started out with much
more humble ambitions. Some just wanted
to give students an alternative to a
summer job. Others just wanted make their
friends feel like pimps."

This situation is likely true but doesn't
say much:

Why? The situation says that most
successes are from luck. Then the
suggestion is to forget about planning and
count on luck?

Here is an analogy that explains the
situation: Go to a famous golf course and
to a par 3 hole. Get the data for the
past 10 years on who made a hole in one.

See, first, what fraction of the holes in
one were made by (A) professional golfers
and (B) everyone else. Will likely
observe that nearly all the holes in one
were made by (B), not the professional
golfers but by everyone else.

How can this be true? Sure, there were
only a few pro golfers but many more of
everyone else. So, in the end, the luck
of the many got more holes in one than the
skill of the few.

See, second, what the probability of a
hole in one was for (A) the professional
golfers and (B) everyone else. Will
likely find that the chances for the pros
was at least 10 times higher than for
everyone else.

So, we have that (i) nearly all the hole
in one shots were from luck but (ii) the
chances of a hole in one were much better
for players with real skills.

So, if you were betting on a hole in one
shot, then you should put your money on
the pros with real skills.

Similarly for picking startup projects:
Go with solid planning and not just with
luck.

"Most wouldn’t have cleared the hurdle of
the billion dollar idea."

Fine: Discovering that fact is part of
evaluating projects. But when do find a
project that looks like it should be worth
$1 T, don't automatically throw it away as
"outlandish".

Sure, maybe on average the $1 T projects
take more risk capital than the $1 B or $1
M projects, but guessing here is foolish
and not necessary. Instead, the amount of
risk capital needed should be part of the
planning, the good planning that is
believable. As we know from many projects
-- long bridges, tall buildings, deep
tunnels, big dams -- it is possible to
plan big projects with accurate time and
cost estimates.

Yes, time and cost estimates can be
especially difficult for software
projects, but just multiply both by a
factor of about 20 to account for work not
directly for the project but, say, for
getting around bugs in infrastructure
software, bad documentation, time to learn
new APIs, computer system management
Excedrin headache #228,884,454, etc. and
might be closer to reality.

"Over the years I’ve watch as that little
company has grown from a couple thousand
dollars a month to a couple million
dollars a month. Next year, that unfunded
family run business will do over $100M in
revenue."

Terrific. But without good planning, that
example represents some astounding good
luck, close to winning a lottery ticket.
Betting on lottery tickets is foolish for
nearly everyone.

"You may be surprised with how little
ambition it really takes to eventually
change the world."

Luck and lottery tickets are still poor
bets.

Instead, we should have good planning.
And if the plans point to a company worth
$1 T, then check the plans numerous times
and ways and then cheer.

Once a father quite successful in business
told his son:

"You have a lot of good ideas to invest $1
million and make $1 billion. Why not have
an idea to invest $1000 and make $1
million."

Yes, but better still, have an idea to
invest $1000 and make $1 B or $1 T.

It appears that here is the main reason
for regarding $1 T plans as "outlandish"
and discarding them: There are so far no
$1 T companies.

So, in effect, this says that we can't
plan and practice to make a hole in one
and instead should look like the non-pro
golfers who made a hole in one with luck
So, we should not plan but copy the
pattern of the non-pro golfers, copy
their brand of cubs, shoes, hat, shirt,
etc.

Instead, it really is possible to have an
idea for something really new and
terrific, to have good plans to achieve
it, and to achieve it essentially on time
and on budget, e.g., as a low risk
project.

Many of the best examples are from the
all-time, unique, world-class grand
champion of advanced information
technology projects, the US DoD. For an
example? Sure, GPS.

Betting on luck instead of planning? I
remain surprised that people would suggest
such a thing.

Or, when the given point does not make
good sense, maybe there is a hidden point
that does. Or there is the advice "Always
look for the hidden agenda". For VCs, one
guess at a hidden agenda is publicity for
more "deal flow".