Mark Cuban & Gary-V Define Success (+12 More Entrepreneurs)

As a contributor for, I connected with many inspiring entrepreneurs. I asked them each three questions: the best advice they’ve ever received; their biggest failure and lesson learned; and their definition of success.

Mark Cuban 

Best Advice? Today is the youngest you will ever be, live like it.

Biggest Failure & Lesson? Lots of failures, but I haven’t had my biggest one yet.

Definition of Success? Waking up every morning with a smile on my face knowing its going to be a great day.

Barbara Corcoran 

Best Advice? You will never succeed without me!

That was my boyfriend/business partner’s prediction when I ended things. Right after he announced he’d marry my secretary.

Biggest Failure & Lesson? Deciding to put our apartments for sale on videotape so customers wouldn’t have to go out to see them. I pissed away my first profit of $77,000 and it was dead on arrival.

But, in an effort to save face, I put them on this new thing called the Internet (it was 1989). We had two sales in the first week. Then I registered all my competitors URLs under my name. One by one they started calling.

Definition of Success? Feeling proud of yourself for trying.

Guy Kawasaki 

Best Advice? Never ask people to do something I wouldn’t do.

Biggest Failure & Lesson? That Macintosh didn’t dominate 100% of the PC market share. I learned that the best gizmo doesn’t necessarily win.

Definition of Success? First, that you made the world a better place. Second, you don’t “have to” do anything.

Gary Vaynerchuk 

Best Advice? Word is bond. Early on, my dad taught me that when I committed to buying cases of any given wine, I was in for them, no matter what transpired between commitment and delivery. That’s been the single biggest influence on my success.

Biggest Failure & Lesson? In 2009 I had founded VaynerMedia, purchased Cork’d, and was involved in about half a dozen other business ventures. I tried to do everything, and ended up not doing anything.

Definition of Success? I define success by how many people show up to my funeral.

Christiane Lemieux 

Best Advice? To “stay focused.”

As a serial entrepreneur—I have a very bad case of “shiny object syndrome.” A straight line meets milestones much more quickly.

Biggest Failure & Lesson? Not seriously vetting an investor I had. Not all money is helpful or strategic, and all money has strings attached. Sometimes theses strings become a noose.

Definition of Success? How my business touches the people I work with.

When I think about my employees in New York who have great healthcare, or my partners in Vietnam sending their kids to school—it makes the hard work, travel and constant forward motion worth every single minute.

Grant Cardone 

Best Advice? The best investment you will ever make is in yourself.

Biggest Failure & Lesson? I should have gone 10X bigger from the get-go.

It’s the same amount of work to stay small as it is to go big. Building a $100 million dollar company is no more work than building a $1 million company.

Definition of Success? The attainment of the gap between my current reality and my potential.

Jack Canfield

Best Advice? Dream big, ask boldly for what I want, and to take action on an idea immediately.

It was that advice that led to the Chicken Soup for the Soul series, which now has 500+ million copies in 47 languages.

Biggest Failure & Lesson? Spending a year creating a new “human potential” internet portal and never got it off the ground.

I learned to stick to our core business—writing and training. And the need for adequate funding to pull off such a huge venture. We were ignorantly going up against AOL at that time.

Definition of Success? Fulfilling your soul’s purpose.

I believe we each have a purpose to fulfill in this lifetime.

Alexa von Tobel

Best Advice?  Get up, dress up, show up.

Get up ready to go, dress the part, and show up with your best attitude and energy to tackle all that your day will bring.

Biggest Failure & Lesson? You have to be okay with failure. If you’re not failing, you’re likely not pushing yourself hard enough.

Definition of Success? Working toward a goal I can believe in. My life’s mission is to make financial education and advice more accessible. If I can help people progress with money, then all of this work has been worth it.

Noah Kagan

Best Advice?  Don’t be a b*tch.

I ran away from home and then my mom went across the street and made me come home. My step-dad then said instead of running away, I need to face issues head on.

Biggest Failure & Lesson? Ha. This has been documented more than I care. Getting fired from Facebook. Losing out on $200 million at today’s market value. Biggest lesson learned is that the best way to get known is to create things that help others.

Definition of Success? Doing work that I’m proud of and having fun.

Most people want complex answers but there’s not a monetary or external goal. Every time I focus on things that I internally truly want then I feel satisfied when I get them. It’s not a feeling of success but proudness with myself for wanting something and getting it. Be careful to avoid having others put their success pressures on yourself.

Erika Trautman

Best Advice? “Fearlessness is a muscle. The more I exercise it, the less my fears run me” (a quote by Ariana Huffington).

Biggest failure & lesson? Rapt Media went through some scary moments as we were getting off the ground. I thought if my staff knew exactly how tough things were, they would panic and quit their jobs. So I kept them out of the loop while closing our seed round. When we finally closed that round, I turned to the team to celebrate only to discover I’d lost their trust. Since then, I share the good news and the bad and we tackle the issues together because the vision is worth it.

Definition of success? Success is building and leading an amazing team capable of creating something indelible and transformational.

Steven Pressfield & Shawn Coyne 

Best Advice? Never pass up an opportunity to use a rest room.

Biggest Failure & Lesson? Failing to start doing what matters sooner. The lesson learned is to start before you’re ready.

Definition of Success? Discovering what you’re supposed to be doing and then doing that.

Jessica Butcher 

Best Advice? Invest in memories.

Biggest Failure & Lesson? Allowing a negative situation to spiral downward, and then choosing to quit rather than salvage the situation through small, positive steps.

Definition of Success? Achieving a true work-life balance.

Paul Budnitz

Best Advice? People have a tendency to play to their strengths and hide their weaknesses. Our weaknesses are always there, whether we like it or not.

I’ve learned to ask for help from a beginner’s perspective, without being ashamed of that.

Biggest Failure & Lesson? I don’t see anything that I do as a failure (or a success).  I know that sounds cheesy, but it’s really how I operate. It’s all just another step on a road that never ends.

Definition of Success? Being willing to lose it all, if that’s what it takes.