Which of these 2 entrepreneurs do you admire more?
Mr. X, who came from poverty, started with almost nothing, and
built a business that generates an income in the lower to mid six
figures … and a net worth in the low seven figures?
Or Mr. Y, who came from a well-to-do family, which provided him
a grub stake worth several million dollars, and which — to his
credit — he turned a successful business, making himself
extremely rich in the process?
A lot of people might say Mr. Y … because he built the more
significant business and fortune.
But — even if both entrepreneurs multiplied what they started by
the same factor … say 20-fold … I pick X as my hero hands-down.
Both had to work hard, be smart, and overcome many challenges.
But X had one more challenge that Y did not, which to me makes
his success much more significant.
Namely, that when you come from modest beginnings, and have no
real net worth to start with, you are constantly close to
financial disaster when you start a small business.
Typically you invest almost all your time and also your rent
money in it.
So if the business doesn’t take off, you are up poop’s creek.
Worse, if it hobbles along with minimal success, as so many do
for so long, you — much like Jed Clampett — can barely keep your
Plus, many neighbors, relatives, and even friends who don’t have
the guts to start a business as you did take delight in your
struggle and lack of big-time success.
Why? Because doing so somehow makes them feel less threatened by
you and better about themselves.
If you look at billionaire businessmen turned politicians today,
I think ex-NYC Mayor Michael Bloomberg is the classic
“lift-yourself-up-by-your-boot-straps” Mr. X — the kind of
success story I really admire.
And President Trump is the “born-with-a-silver-spoon-in-his-mouth”
Mr. Y, for whom the living is much easier.
Born February 14, 1942, Michael Bloomberg grew up in a
lower-middle-class household in the Boston area; his dad was a
He went on to build a huge media empire … and various sources
estimate he is worth anywhere from $30 billion to $49 billion;
let’s call it $35 billion.
Also, Bloomberg got there from just about nothing. No money or
business training from a rich and successful daddy.
I don’t follow Bloomberg closely, but in the few interviews I
have heard and articles I have read, he seems to me a modest,
humble, kind, and generous guy.
Another example: Daehee Park and John Marino, who started an
e-commerce business, Tuft & Needle, with $6,000 in 2013 and by
2016 had built it to $100 million in annual sales.
Quite an accomplishment, wouldn’t you agree, especially
considering not one rich relative handed them a million or more
and said, “This should make life easier, boys” — as it would
Now on to Donald Trump, who claims that he got his start with
“only” a one million dollar grubstake from his father, a
successful real estate developer.
(By the way, if anyone feels like giving me a million dollars, I
promise not to use the word “only” in reference to your gift.)
But that million was just for starters, according to the Wall
Their reporters tracked down a 1985 casino-license disclosure
that showed Trump’s father gave him a second loan, this one for
$14 million — a value of $31 million in today’s dollars.
According to Forbes, Trump is worth around $3.5 billion. Other
sources, such as Vanity Fair, say the figure is much lower.
Now, I’m not saying trust-fund babies who build empires aren’t
smart … or successful … or laudable … or impressive.
I’m just pointing out a simple truth:
They never had to deal with what I believe is the toughest,
riskiest, and scariest part of starting a small business: the
early stage where you risk it all, and if you lose, you’re crap
out of luck.
To me, the fact that silver-spooners are spared this anxiety,
fear, and possibility of destitution … thanks to the security
and backup provided by their daddy’s bankroll … certainly
doesn’t negate their accomplishments.
But also in my opinion, it DOES make their achievement
significantly less impressive than if they had, like many of our
immigrant parents or grandparents who built successful lives,
come to our shores from Ellis Island with only $10 in their