Biggest Failures, Best Advice and Defining Success From 14 Inspiring Entrepreneurs

Biggest Failures, Best Advice and Defining Success From 14 Inspiring Entrepreneurs

Barbara Corcoran

Image credit: barbaracorcoran.com

I recently connected 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, lessons learned and their definition of success. Here what they generously shared.

1. Barbara Corcoran

The Shark Tank investor went from achieving straight D's in high school to creating a multi-million dollar real estate firm in her early twenties.

Biggest failure: 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.

Biggest lesson: 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. 

Best advice: “You will never succeed without me!” The prediction of my boyfriend and business partner when I ended our business partnership -- after announcing he'd marry my secretary.

Definition of success: Feeling proud of yourself got trying.

Related: The Best Business Advice You'll Ever Get

2. Guy Kawasaki 

Guy dropped out of law school to complete an MBA at UCLA. His years working alongside Steve Jobs shaped his work as chief evangelist at Canva and co-founder of Alltop.

Biggest failure: That Macintosh did not achieve 100 percent market share of the PC market.

Biggest lesson: I learned that the best gizmo doesn't necessarily win. It's taken 30 years, but I've gotten over this.

Best advice: Never ask people to do something you wouldn't do. This is a very good test for how you treat your employees and customers, assuming you're not a sociopath. 

Definition of success: First, that you made the world a better place. Second, you don't "have to" do anything. 

3. Gary Vaynerchuk 

From managing seven lemonade stands as an 8-year old, Gary hasn't skipped a beat with numerous startups, bestselling books and, most recently, creating VaynerMedia.

Biggest failure: 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.

Biggest lesson: 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.

Best advice: Word is bond.

Definition of success: I'll define success by how many people show up to my funeral.

4. Christiane Lemieux

The Ottawa native started DwellStudio from her apartment in 1999 after grinding it out for years as a fashion intern in New York. 

Biggest failure: The biggest mistake I made was not seriously vetting an investor I had in the business.

Biggest lesson: 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. 

Best advice: "Stay focused.” As a serial entrepreneur with “shiny object syndrome,” my path to success has been a jagged line. A straight line meets milestones much more quickly.

Definition of success: Success for me is defined by how my business touches the people I work with.

Related: I Screwed Up: How 3 Famed Entrepreneurs Learned From Failure

5. Grant Cardone

After starting off in automotive sales, Grant has gone on to become a New York Times bestselling author, successful entrepreneur and founder of Whatever It Takes Digital Network.

Biggest failure: I should have gone 10X bigger from the get go.

Biggest lesson: 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.

Best advice: The best investment you will ever make is in yourself. (Grant's mom told him this).

Definition of success: The attainment of the gap between my current reality and my potential. 

6. Jack Canfield 

Graduating from Harvard, Jack turned the Chicken Soup for the Soul series into an international billion-dollar enterprise. 

Biggest failure: We spent a year attempting to create a new human potential oriented internet portal, and we never got it off the ground.

Biggest lesson: To stick to our core business -- writing and training. And having adequate funding for the marketing needed to pull off such a huge venture. We were ignorantly going up against AOL, which was spending millions. 

Best advice: Dream big, ask boldly and take action on an idea immediately.

Definition of success: Fulfilling your soul's purpose. I believe everything works better when it is done in the spirit of love and joy rather than fear and greed.

7. Mark Cuban 

After a billion-dollar deal with Yahoo, Cuban purchased the Mavericks. The Shark Tank investor's court side dancing as entertaining as his appearance on Dancing with the Stars.

Biggest failure: Lots of failures, but I haven't had my biggest one yet.

Best advice: Today is the youngest you will ever be, live like it.

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

8. Alexa von Tobel 

Launching her personal finance company, LearnVest in 2006, Alexa was inaugurated by President Obama as a member of the Presidential Ambassadors for Global Entrepreneurship early this year.

Biggest failure: As an entrepreneur, you have to be OK with failure. If you’re not failing, you’re likely not pushing yourself hard enough. 

Biggest lesson: “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.

Best advice: Get up, dress up, show up.

Definition of success: 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.

Related: Life Advice From 18 of the Wealthiest People in History (Interactive Graphic)

9. Noah Kagan 

Beginning his career at Intel, Kagan joined, and left, Facebook as employee #30. The marketing expert has numerous startup successes in the tech world, currently working behind AppSumo.

Biggest failure: 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: The best way to get known is to create things that help others.

Best advice: 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.

Definition of success: Doing work that I'm proud of and having fun. Be careful to avoid having others put their success pressures on yourself.

10. Erika Trautman 

Having owned an Emmy award-winning video production company, Erika's current venture, RaptMedia, is about enhancing interactivity for online video.

Biggest failure: Rapt Media went through some scary moments getting off the ground. I thought if my team knew how tough things were, they'd panic and quit their jobs. So I kept them out of the loop. When we finally closed our seed round, I turned to the team to celebrate only to discover I’d lost their trust.

Biggest lesson: Without openness and transparency, you can lose the trust of your team. Since then, I share the good news and the bad. We tackle the issues together because the vision is worth it.

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. 

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

Related: The Definition of Success, According to 5 Entrepreneur Superstars

11 & 12. Steven Pressfield & Shawn Coyne 

A prolific writer, Pressfield is known for many works including The Legend of Baggar Vance, and The War of Art. He has partnered with fellow writer, Shawn Coyne, and created Black Irish Entertainment.

Biggest failure: Failing to start doing what matters sooner.

Biggest lesson: The lesson learned is to start before you're ready.

Best advice: Never pass up an opportunity to use a rest room.

Definition of success: Discovering what you're supposed to be doing and then doing that.

13. Jessica Butcher 

Based out of London, Jessica is the co-founder and CMO of Blippar, the augmented reality platform that turns printed images into digital experiences.

Biggest failure: Allowing a negative situation to spiral downward, and then choosing to quit rather than salvage the situation through small, positive steps

Biggest lesson: 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.

Best advice: Invest in memories. It’s ultimately what life is about—people, places, moments and experiences. 

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

14. Paul Budnitz 

Studying photography, sculpture and film at Yale, Paul has gone on to create Kidrobot, Bunditz Bicycles, and most recently, the social media platform Ello.

Biggest failure: 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.

Biggest lesson: 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. 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.

Best advice: Genpo Roshi, an American Zen Master said, when we bury the parts of ourselves we don’t like, those negative aspects of our personalities eventually come back to haunt us. I’ve learned to ask for help from a beginner's perspective, even if I’m the one who’s running the company and I’m asking for help from an intern.

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.

Related: Embracing Failure on the Path to Success