As a contributor for I was able to connect with some of the most inspiring men and women in entrepreneurship. I asked them to share the best advice they’ve ever received, their biggest failure and lesson learned, and their definition of success.


Barbara Corcoran | Shark Tank Investor, Business Expert

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Best Advice? “You will never succeed without me!” My boyfriend and business partners prediction when I ended our business partnership, after he announced he would marry my secretary.

Biggest Failure & Lesson? My fabulous new idea to put all 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. In an effort to save face, I put them on this new government thing called the Internet. It was 1989. We had two sales out of London in the first week. I registered all of my competitors URLs under my name. One by one they called.

Definition of Success? Feeling proud of yourself got trying.


Guy Kawasaki | Chief Evangelist at Canva, Co-Founder of Alltop


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Best Advice? Never ask people to do something I wouldn’t do. This is a very good test for how you treat your employees and customers—assuming you’re not a sociopath.

Biggest Failure & Lesson? My biggest failure is that Macintosh did not achieve 100% market share of the PC market. I learned that the best gizmo doesn’t necessarily win. It’s taken 30 years, but I’ve gotten over this.

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


Gary Vaynerchuk | Author & Founder of VaynerMedia


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Best Advice? Early on in my career, my dad taught me that when I committed to buying cases of any given wine, I was in for them no matter what. It didn’t matter what transpired between commitment and delivery, I would take the merchandise because word is bond. That’s been the single biggest influence on my success, and something that might surprise a lot of people given my showmanship.

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. Since then I’ve learned how to focus much better, and I’ve built up a team around me that allows me to do just that, so let’s see if I’ve learned anything. :)

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


Christiane Lemieux | Founder of DwellStudio


Image Credit: CrainsNewYork

Best Advice? I’ve made every mistake and received all forms of advice; from things that are valuable to ideas that are totally off the wall. I’ve tried most. But the single best piece of advice is to “stay focused.” As a serial entrepreneur—I have a very bad case of “shiny object syndrome,” I am distracted and seduced by new ideas, concepts, business models and opportunities. My path to success has been a jagged line. A straight line meets milestones much more quickly.

Biggest Failure & Lesson? The biggest mistake I made was not seriously vetting an investor I had in the business. Not all money is helpful or strategic, and all money has strings attached. Sometimes theses strings become a noose. Be very careful—ask all the right questions, vet your investors very seriously.  It’s a marriage and you want a healthy and sustainable one to get you through the ups and downs of business.

Definition of Success? Success for me is defined by how my business touches the people I work with.  My greatest joy, and hopefully my most enduring legacy has been all of the lives I’ve touched both here and overseas through the jobs I’ve created.  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 | Entrepreneur and Creator of Whatever It Takes Digital Network


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Best Advice? The best investment you will ever make is in yourself. (Grant’s mom told him this).

Biggest Failure & Lesson? I should have gone 10X bigger from the get-go. The lesson learned was, 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? Success for me is the attainment of the gap between my current reality and my potential.


Jack Canfield | Creator of Chicken Soup For The SoulSuccess Coach 


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Best Advice? When I was in my twenties, W. Clement Stone, who was my boss and mentor, told me to always dream big, ask boldly for what I wanted, and to take action on an idea immediately. It was that advice that ultimately led to the creation of the Chicken Soup for the Soul series, which now has over 500 million copies in print in 47 languages around the world.

Biggest Failure & Lesson? We spent a year attempting to create a new human potential oriented internet portal, and we never got it off the ground. What I learned was to stick to our core business—writing and training. I also learned the importance of having adequate funding for the marketing needed to pull off such a huge venture. We were ignorantly going up against AOL at that time, and they were spending millions advertising everywhere.

Definition of Success? I believe success is fulfilling your soul’s purpose. I believe we each have a purpose to fulfill in this lifetime. Mine is to empower people and organizations to live their highest vision in a context of love and joy and in harmony with the highest good of all concerned. I believe everything works better when it is done in the spirit of love and joy rather than fear and greed, and that if we’re always looking to create win-win solutions rather than only pursuing our own selfish interests (as in the case of the recent financial meltdown caused by a handful of bankers and investors), the world would function much better.


Mark Cuban | Shark Tank Investor, Owner of Dallas Mavericks


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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.


Alexa von Tobel | Author & Founder of LearnVest


Image Credit: LearnVest

Best Advice? Financially, never overspend on your home. By underspending here, it can give you a lot of room and flexibility throughout your entire budget. I also love the motto “get up, dress up, show up.” By this I mean 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? As an entrepreneur, I believe you have to be OK with failure. If you’re not failing, you’re likely not pushing yourself hard enough. The important thing is to figure out how to accept these failures, and then get back up and keep going. “Fail fast” is a concept we tend to encourage at LearnVest—don’t be afraid to try something, but be ready to learn from it and move forward.

Definition of Success? To me, success is working towards a goal I can believe in. My life’s mission is to make financial education and advice accessible to people nationwide. If we can help people make progress on their money, then I’d say all of this work has been worth it.


Noah Kagan | Marketing Expert & Founder of AppSumo


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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. I think about that moment and the message a lot. Face your fears and go towards them—never as scary as they seem.

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 | Founder of RaptMedia


Image Credit: Huffington Post

Best Advice? “Fearlessness is a muscle. The more I exercise it, the less my fears run me.” This is a quote I once read by Ariana Huffington. Paradoxically, I think fearfulness can make a person reckless, whereas fearlessness gives you the mental space to think calmly and logically about tough decisions.

Biggest failure & lesson? Without openness and transparency, you can lose the trust of your team, especially during the tough times. Rapt Media went through some scary moments as we were getting off the ground. I thought if they knew exactly how tough things were, they would panic and quit their jobs and then we’d really be in trouble. So I kept them out of the loop during some critical events while we were 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? To me, success is building and leading an amazing team capable of creating something indelible and transformational. I think many entrepreneurs are driven to change the world, and I’m no different.


Steven Pressfield & Shawn Coyne | Authors & Co-founders of Black Irish Entertainment


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 | CMO & Co-Founder of Blippar


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Best Advice? Invest in memories. It’s ultimately what life is about—people, places, moments and experiences. Money can be a great enabler for these when invested in shared experiences like parties, holidays or team days out. But many can be achieved on a budget or at no cost—in making new connections, enjoying a sunset, great music or a good book.

Biggest Failure & Lesson? Allowing a negative situation to spiral downward, and then choosing to quit rather than salvage the situation through small, positive steps. Sometimes it’s the right decision to end a particular course of action or working relationship, but I now make a more concerted effort to salvage or reverse a situation. If that’s not feasible, at least bring it to a more positive conclusion.

Definition of Success? Achieving a true work-life balance. Doing something you love work-wise, whilst also coming home to a happy, healthy home.


Paul Budnitz | Founder of Kidrobot, Bunditz Bicycles, Ello


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Best Advice? People have a tendency to play to their strengths and hide their weaknesses. Genpo Roshi, an American Zen Master once said, when we bury the parts of ourselves we don’t like, those negative aspects of our personalities eventually come back to haunt us. 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—even if I’m the one who’s running the company, and I’m asking for help from an intern.

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—there’s always a disaster, followed by things working out fairly well, followed by another disaster. It’s a cycle. After a while, you learn to look out for disasters when things are going well, and take heart when you’re at the bottom that things will reverse eventually, too.

Definition of Success? Being willing to lose it all, if that’s what it takes. If you aren’t open to that, you’ll never be able to take the risks necessary make something truly amazing.


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