10 Smart Life Lessons From Successful Teenage Entrepreneurs

UPDATED: May 19, 2023
PUBLISHED: March 5, 2017

Your dream as an entrepreneur doesn’t end with you. After all, it’s one thing to find success for yourself and another thing to witness success take shape in the lives of your children.

Related: 7 Entrepreneurial Traits to Teach Your Child

We all want to pass on our entrepreneurial traits. Unfortunately, a host of recent studies agree those traits are struggling in upcoming generations. Combating cultural apathy and entitlement isn’t easy. And naturally, there’s no shortage of contrary advice from the so-called experts.

So instead, what if we turned the tables and 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.”

“I ended our conversation—as I always do with new people—by asking him for his own best piece of advice. He said something so simple that’s stuck with me: ‘Don’t sweat the small stuff, because everything is small stuff.’

Being an entrepreneur is not easy, and I’ve seen many that get upset when they don’t make a sale, when they’re criticized or when they’re not valued because of their age. When I feel myself getting frustrated or overwhelmed, I force my mind to go back and remember, ‘Don’t sweat the small stuff, because everything is small stuff.’”

That’s good advice for any age, but given the challenges and pressures of being young, it’s especially powerful for your children to hear. Of course, more than just hearing it, embodying that principle and modeling how to take disappointments in stride are necessary.

2. Failure isn’t the end.

As the 16-year-old founder of YOUTHXCO, an independent clothing company aimed at youth empowerment, Rachel Ji has already experienced the ups and downs of entrepreneurial life. Her parents were first-generation immigrants to New Zealand and hearing stories about her dad washing dishes for $3 an hour to support a blossoming family while attending college taught her two things.

First, obstacles are not an excuse: “If the odds are against you, all that means is you have to work harder than everyone else.” Second, it’s OK to fail.

As Rachel puts it:

“My parents’ hard work gave me the freedom to fail because I didn’t have to immediately shoulder all the responsibilities of the real world. When you’re a teenager and your business falls apart—like my first did because I was too young to sign legal contracts—you’re not going to end up homeless and starving. Not if your family is behind you.”

Giving your child the freedom to fail doesn’t mean bailing them out or sheltering them from the downside of their mistakes. But it does mean creating a safe space in their lives to experiment, take chances and learn.

3. Mortality breeds passion.

Will Hewitt had a typical, small-town upbringing: His mother was a teacher and his father was a seafood marketer. In late 2015, Will, 16, co-launched the robotics company Thnkbot, committed to introducing other young people to his passion: electronics and programming.

Since then, he has been invited to Silicon Valley multiple times to meet leaders from all over the startup spectrum, from three-person dream machines in someone’s garage to top-level management at Google.

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.’

“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.

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.

Related: How to Make Sure Your Children Become More Successful Than You

Aaron Orendorff

Aaron Orendorff is the Head of Marketing at Recart. Previously, he served as Editor in Chief of Shopify Plus; his work has appeared on The New York Times, Forbes, Mashable, Business Insider and more. If you’d like to connect with Aaron, reach out via social—he’s a sucker for DMs about ecommerce marketing, bunnies and rejection.