So instead, what if we turned the tables and “I ended our conversation—as I always do with work harder than everyone
han everyone else.” Second, it’s
went straight to the source, the very people
who know the most about raising success…
because that’s how they were raised?
To do that, I tracked down 10 teenage
entrepreneurs who have already seen massive
wins, and asked one question: “What’s the
single best lesson you’ve learned so far?”
Here are their answers.
1. Don’t sweat the small stuff.
Caleb Maddix isn’t your typical 14-year-old. As
he unabashedly told Forbes earlier this year, “I
don’t want to be 20 years old and looking for a
job. I want to be 20 years old and providing
jobs! My goal is to be a billionaire by 30.”
As the CEO of Kids 4 Success, a membership
site for aspiring entrepreneurs, he’s well on his
way. In fact, Caleb’s worked with greats such
as Gary Vaynerchuk, Kevin Harrintgon, John
Lee Dumas and soon Tony Robbins.
Surprisingly, the best lesson he’s learned so far
didn’t come from any of those big names.
Instead, it came from a security guard he met
at a hotel:
 
“Don’t sweat the small stuff, because
everything is small stuff.”
new people—by asking him for his own best OK to fail.
piece of advice. He said something so simple
As Rachel puts it:
that’s stuck with me: ‘Don’t sweat the small
stuff, because everything is small stuff.’ “My parents’ hard work gave me the freedom
to fail because I didn’t have to immediately
“Being an entrepreneur is not easy, and I’ve
shoulder all the responsibilities of the real
seen many that get upset when they don’t
world. When you’re a teenager and your
make a sale, when they’re criticized or when
business falls apart—like my first did because I
they’re not valued because of their age. When
was too young to sign legal contracts—you’re
I feel myself getting frustrated or
not going to end up homeless and starving.
overwhelmed, I force my mind to go back and
Not if your family is behind you.”
remember, ‘Don’t sweat the small stuff,
because everything is small stuff.’” Giving your child the freedom to fail doesn’t
mean bailing them out or sheltering them from
That’s good advice for any age, but given the
the downside of their mistakes. But it does
challenges and pressures of being young, it’s
mean creating a safe space in their lives to
especially powerful for your children to hear.
experiment, take chances and learn.
Of course, more than just hearing it,
embodying that principle and modeling how to 3. Mortality breeds passion.
take disappointments in stride are necessary.
Will Hewitt had a typical, small-town
2. Failure isn’t the end. upbringing: His mother was a teacher and his
father was a seafood marketer. In late 2015,
As the 16-year-old founder of YOUTHXCO, an
Will, 16, co-launched the robotics
independent clothing company aimed at youth
company Thnkbot, committed to introducing
empowerment, Rachel Ji has already
other young people to his passion: electronics
experienced the ups and downs of
and programming.
entrepreneurial life. Her parents were first-
generation immigrants to New Zealand and Since then, he has been invited to Silicon
hearing stories about her dad washing dishes Valley multiple times to meet leaders from all
for $3 an hour to support a blossoming family over the startup spectrum, from three-person
while attending college taught her two things. dream machines in someone’s garage to top-
level management at Google.
First, obstacles are not an excuse: “If the odds
are against you, all that means is you have to What was Will’s impetus?
“If there’s one lesson, it’s that passion is key to
everything you do. Time is very finite, and the
sum total of what you manage to create in
those 80, 90, maybe even 100 years is what
you are going to be remembered for.
“I was taught that you have to question
yourself every day, Is this what you want to be
remembered for? And if that answer is ever no,
then you may as well not even get up that day
because something needs to change.”
Raising your kids beneath an awareness of
their own mortality might sound strange, but
that knowledge—reinforced by self-searching
questions—shortcuts the wandering paths
many young people get lost inside. Putting the
limits of life front and center puts a premium
on passion.
4. Experience is the best teacher.
With $500 in their pockets and a 6-month-old
baby, Shreyas Parab’s parents moved to the
U.S. They were alone and scared, but they
didn’t let that stop them for pursuing the
reason they came: a better future.
Shreyas, 16, is an entrepreneur to the core. He
started his first company, NovelTie, when he
was 14, and after almost $20,000 in sales, he
started a second, SpellForSuccess, which was
recently acquired by an education company in
Chicago.
Where did Shreyas’ drive come from?
“The best gift my parents have given me is not
doing everything for me. My parents were
upfront that if I pursued these things on my
own, it would be my responsibility, not theirs.
“Some parents do all the nitty gritty work for
their entrepreneur children, but my parents
want me to learn on my own. They want me to
learn through doing, making mistakes and
through the best form of education possible:
experience.”
The lessons that often mean the most aren’t
always what parents do… but what they don’t.
5. Resist the temptation to say “stop.”
At 17, Connor Blakley works with brands on
youth marketing, specifically Gen Z; his tactics
have been featured in Forbes, Entrepreneur,
Inc. and Huffington Post. In 2016, StartUp
Grind named him the “number one high-school
entrepreneur to watch.”
Why all the buzz? Simple. Because Connor’s
by-GenZ-for-GenZ advice comes directly from
the hard-won experiences his parents never
stood in the way of.
As Connor puts it:
“My parents played an important role in my
formation as a young entrepreneur. But it’s
what they didn’t say to me that mattered
most. My parents never told me ‘Stop!’
whether that was selling door to door or
littering my room with rock collections I was
merchandising. They didn’t even get mad
when I almost got in huge trouble for starting a
homework-selling network. I can attribute all
this to them seeing the bigger picture.”
It can be scary to let your child go all in on
their entrepreneurial journey. But often, that
fear is self-centered. Resisting the temptation
to bubble wrap kids with the word “stop” is
hard, but there’s no substitute for letting them
make their own choices.
6. Adapt to change.
Last February, Benjamin Stern, the now 17-
year-old CEO and founder of Nohbo, appeared
alongside his “bubbie” (his grandmother)
on Shark Tank and closed a $100,000 deal with
Mark Cuban in exchange for 25 percent of the
company.
Although the episode highlighted Benjamin’s
love of both innovation and the environment
(Nohbo sells “the world’s first eco-friendly
shampoo ball”), what it didn’t show was the
lesson attending nine different schools over
the past few years taught him:
“My parents seemed to have a strange
addiction to moving. Even though there were
moments of extreme discomfort, I think
serendipitously, they taught me to adapt to
the new—new challenges and new
surroundings. It wasn’t easy all the time, but
the frequent moving is a character builder, and
it makes an individual confront what they
dread: change.”
Change is an inevitable and often painful part
of entrepreneurship. Unfortunately, it’s also an
ethereal concept to most young people.
Teaching your child adaptability doesn’t
necessitate moving. That’s one approach, but
it can also be instilled by inviting them into the
big decisions you’re facing as well as not
sheltering them from the changes they
themselves might experience.
7. Life is bigger than you.
When they were 12, twins Yashraj and Yuvraj
Bhardwaj used to do their best thinking
outside of the classroom. Not by choice, but
because the doubts and questions they raised
were far enough beyond the assigned
curriculum that their teacher would banish
them outdoors on a weekly basis.
Now 17, the brothers have authored 22
research projects, possess seven patent
applications, presented at TEDx Delhi, and
were awarded the 2016 REX Karamveer Global
Fellowship in association with United Nations.
Their passion for biochemistry and electronics
was fueled at an early age.
As Yashraj told me:
“Our parents used to tell us that life is bigger
than you. The truest life, fulfillment, meaning
and joy is found in the service of others. They
encouraged us to create nontraditional
solutions to problems that other people were
either ignoring or letting this world down. You
can make yourself immortal if you help others
without being selfish.”
We’re all naturally selfish creatures. However,
fulfillment comes not from pursuing our own
ends, but from selflessness. Giving your kids a
taste of that deeper fulfillment early on, the
kind that comes from attaching themselves to
a cause bigger than just them, sets them up to
pursue it throughout life.
8. Actions prove words.
James Corneille is an Irish tech entrepreneur
and founder of Positivity Pack, a box
subscription service with one goal: “to spread
happy vibes.” At 18, he’s collected a host of
awards and accolades that’s too long to
reproduce in full but includes top honors from
the European branches of Microsoft, Facebook
and Google.
So what’s the lesson that stands out most in
James’s mind?
“It was seeing my mother and father follow
their own dreams of helping people and
changing the world that inspired me to do the
same. I knew I wouldn’t be happy doing
anything else.
“While I was growing up they would say things
like, ‘Follow your dreams’ or ‘Do what you
love.’ Advice like that is easy to disregard as
cliché because it is. However, once it becomes
more than just words—real actions you can
see from your parents—they get driven home
and come to life.”
In other words, clichés are clichés for a reason:
They’re true. But if you want to plant those
truths in your children’s minds, repetition isn’t
enough; you have to live them out.
9. Commitment before accomplishment.
Born with a life-threatening illness, Marc
Guberti’s mother left her job at Goldman Sachs
to study food chemistry and become a
medicinal nutritionist.
After his recovery, Marc, now 18, started a
blog as an outlet for the voice he felt he’d lost.
That small taste of online success snowballed
into 15 books on marketing and high
performance, a social-media following nearing
500,000, a podcast (where he recently
interviewed Seth Godin), speaking
engagements, and Business Whiz Kids, an
annual youth summer program he founded
with his brother.
And it all comes down to a single idea:
“My mother’s commitment proved to me that
if you put your mind into anything you can
accomplish any goal, no matter how big. My
health struggles silenced my voice for so long
that it created a reservoir of desire for me to
elevate the lives of others with my message.
This commitment to spread my message
combined with emerging social networks
created a stream of endless possibilities.”
10. Make the struggle feel natural.
The oldest entrepreneur on our list, Ulyses
Osuna, is 19, but he’s also one of the most
ambitious. As the founder of Influencer Press,
Ulyses hasn’t just appeared in major
publications such as Forbes,
Entrepreneur and Inc., he’s built a thriving
business around getting his clients featured on
those same publications themselves.
The public relations world is notorious for high
levels of rejection, which is why Ulyses’ best
lesson is all about reality:
“My parents didn’t tell me traditional things
like, ‘Oh you got this,’ ‘Just do your best’ or
‘You can be anything you want.’ It was more
things such as, ‘You know, very few people
make it in the world, right? If you’re going to
do this, you need to commit because it’s hard
out there.’
As Charles Duhigg wrote in  Smarter Faster
Better, “We should reward initiative,
congratulate people for self-motivation…
applaud a child who shows defiant, self-
righteous stubbornness and reward a student
who finds a way to get things done by working
around the rules.”
And second, raising success is about doing
more than just speaking good advice, but
putting it into action. After all, it’s not so much
the lessons we teach with our words, but the
lessons we teach with our lives that last.

“They set the realistic expectations of what life

as entrepreneur was like. And because I was
taught at an early age that it was going to be a
struggle, it was easier for me to pursue. The
struggle felt natural.”

So what do all of these lessons have in

common? Amid all the different stories, it
comes down to two key ingredients. First,
getting real about what entrepreneurial life is
like: the disappointments, failures and
pressure. This means giving children genuine
autonomy: the freedom to make their own
choices and face the consequences.