Gary Vaynerchuk answers entrepreneurship and life questions from elementary students

Executive overview

School struggles don't predict entrepreneurial success. Gary Vee, speaking to an entrepreneurship-focused elementary school, shares how he was a poor student but a natural businessman from age seven.

Happiness, curiosity, and resilience matter more than grades or talent. The core message: try your ideas even when others doubt them, stay curious, embrace failure as data, and never let envy dictate your contentment.

You will never know what you're capable of unless you try — and you can always learn from what doesn't work.

On being born vs. becoming an entrepreneur

• Natural affinity for business showed up in second grade — selling lemonade, ringing doorbells, washing cars.
• Being born with a talent means nothing without consistent practice.
• School was hard; finding subjects he loved (math, history, gym) kept him going.
• He'd pay to relive his school years — appreciate the time while it lasts.

On happiness and gratitude

• Happiness comes from gratitude for what you have, not from wanting what others have.
• Envy and jealousy are among the biggest problems in the world — they prevent contentment.
• Keeping life simple — health and family — removes the need to chase things.
• Root for others to have good things; their success doesn't diminish yours.

On learning from failure

• Everyone fails — teachers, parents, every successful person.
• Getting comfortable with losing speeds up your path to a happy life.
• Losses are not permanent defeats; they are step-backs and learning moments.
• After a loss, reflect on what to do differently, then carry that into the next attempt.
• Protecting kids from losing is a mistake; it delays the resilience they'll need.

On curiosity and taking risks

• Curiosity has been essential to Gary's happiness and success.
• Ask "why" and try things before deciding you don't like them.
• When scared of something new, say "maybe" instead of "no" — then commit half the time.
• Some of your favorite activities may be things you haven't tried yet.
• It's far easier to experiment with new things when you're young.

On solving problems

• Start by understanding the other person's perspective, not just your own.
• When someone is unkind, assume they are hurting — not that they are bad.
• Empathy and curiosity together dissolve most conflicts.
• Approach disagreements by asking questions and assuming good intent.

On VeeFriends and drawing

• Started doodling around elementary-school age; kept it up when most kids stop.
• By high school and beyond, most people stop saying they like to draw — he never did.
• Drew the VeeFriends characters himself rather than outsourcing, which was one of the most joyful things he's done.
• Never stop drawing: it builds creativity and brings lasting joy.
• VeeFriends exists to spread values — kindness, resilience, empathy — through characters kids can connect with more than a speaker can.

On choosing the right partners

• When moving from hand-drawn characters to animated versions, he evaluated multiple companies.
• The criterion wasn't just skill — it was also whether he wanted the relationship.
• In business, who you work with matters as much as what they can do.

On speaking to kids

• School assemblies from first grade still stick in his memory at age 47.
• Impact on children is one of the highest-leverage things an adult can do.
• VeeFriends is partly built to scale that impact beyond any single talk.

The message for "little Gary" in the audience

• Even in an entrepreneurial school, people will doubt your ideas — including people you respect.
• Try anyway. You will never forgive yourself for not trying.
• Many of his ideas failed; that's normal and expected on the entrepreneurial path.
• Your destiny as an entrepreneur is to bring your ideas into the world and find out.