The 10 Characteristics of Successful Entrepreneurs

characteristics of successful entrepreneurs, Stephanie Holland, The Freedom Philosophy

What are the core qualities and characteristics of successful entrepreneurs that sets them in a league of their own?

With so many startups doomed to failure how do certain people find success while others don’t?

What’s the magic code and – more importantly – how do you apply it in your own life and business?

Beyond the nuts and bolts of business plans, strategies and models, there are certain qualities and characteristics of successful entrepreneurs that seem to have nothing to do with business and everything to do with their mindset and their ability to keep showing up regardless of outcome.

From observing my favourite entrepreneurs – Richard Branson, James Altucher, Marie Forleo, Srini Rao, Ramit Sethi, and many many more – I’ve noticed 10 core qualities and characteristics that make them stand out from the crowd.

Watch what happens when you bring them into your life and business, too.

The 10 Characteristics of Successful Entrepreneurs

1. Bleed.

Blood, sweat and guts are your brand DNA; no strategist can create that for you. Hold back at nothing so that we know you’re just like us: a perfectly imperfect human being figuring it out as you go.

I don’t know anyone who does this more authentically than Srini Rao. He shares so much of himself in each of his podcast interviews, and with a back catalogue of hundreds of episodes, that’s a LOT of sharing.

2. Wear failure like the Victoria Cross.

The trenches of entrepreneurship will lure you again and again, and you will always return a hero. Because win or lose, victory is more than a badge; it’s knowing more than you did yesterday, and applying it forward.

James Altucher is the ultimate phoenix from the ashes. With failures outnumbering his wins, his capacity for personal growth & learning always brings him out winning.

3. Steal like an artist, and tell us so.

Ideas don’t belong to any one of us, but exist to be amplified by the hearts and minds of us all. When they are strangled by ‘ownership’ we all lose out, and if we don’t steal and infuse it with our Self, the world as we know it will probably end.

It’s Austin Kleon who introduced to this concept in Steal Like an Artist, and now Kirby Ferguson is championing it on steroids. Watch his show Everything is a Remix and you’ll realise that everyone and everything is inspired and empowered by what has come before it.

Someone who does this beautifully is Marie Forleo, who credits all the people who inspired and empower her own success by referencing them in her teachings or having them on her show.

4. Love yourself.

Happy body, heart & spirit are a strategic imperative. Without these, ‘success’ is like a coat without a hanger. Success needs something to hang itself on; what that success look like is completely up to you.

Tony Robbins, love him or hate him, is the most incredible example of self love. His success strategy and his life’s work is underpinned by self love, care and respect, because in being your best Self you can pay this forward to others in your life and work. It’s a strategic imperative for your life, impact & legacy.

If you’ve ever said you don’t have time to take care of yourself, his reply is: “If you don’t have 10 mins, you don’t have a life.”

5. Like the people around you.

Friendship & respect are the cornerstone of any partnership, be it life or business. Sincerely and playfully co-create with your partners, it needs to be true that we can live, work, and laugh simultaneously with the people in our lives.

I love how Chris Guillebeau created an entire community of like-minded people with his annual World Domination Summit hosted in Portland, Oregon.

6. Celebrate truth, not celebrity.

True leadership isn’t always on the cover of FastCompany; it’s sometimes so busy with passion & purpose it doesn’t desire the distraction of limelight. Share your own stories {or spotlight those of others} that reflect our own potential & possibility, and deliver them right to our inbox.

Paul Jarvis delivers the most interesting, actionable and truthful commentary on the world around us from a business/ design/ entrepreneurial point of view. He questions the status quo and inspires us to do the same. I talk more about his awesomeness in How to Be Successful.

7. Write like you talk.

Self-censorship is like forcing our soul through a sieve. Leave your filter switched off and tell it straight; BE a refreshing voice in an ocean of airbrushed vocals.

Oh how I love the way Bushra Azhar does this. She might be the least self-censored online entrepreneur in the world, or just the most uncensored human in the world! There’s no irony lost on the fact that one of her core talents is copyrighting and she’s the founder of The Persuasion Revolution. She owns her truth and speaks it LOUD.

8. Let your hair down.

Our experiences, good and bad, are our greatest source of inspiration. Look up from the screen, venture into the world around you, and have some new ones.

Jenna Soard might lack the scope and scale of the other bigwigs on this list, but not for long. I’ve watched her steady growth of impact & legacy over the last 4 years. The founder of You Can Brand and other business courses for DIY entrepreneurs, she talks boldly of her online dating exploits, travel adventures and diet foibles without restraint, infusing her brand & positioning with bombshell energy.

9. Keep showing up.

When we show up regardless we honour ourselves and give others permission to do the same. Keep a repository of ideas, experiences, successes, and failures so you never have to show up empty-handed.

Every success is preceded by someone who kept showing up even when other’s didn’t. Overnight success does happen, but it begins today and happens some time in the future. Everyone on this list is an example of this list. And YOU are, too.

10. Celebrate ideas.

With a startup culture obsessed with success and failure, ideas are slaves to validation, plans, models and P&Ls. Generate them, but then step back and celebrate them…

And — sometimes — simply follow them.

Regina Anaejionu of ByRegina is the ultimate content machine that James Altucher coined the term for. (Well not really, but she should be!) If ever there was someone who celebrated ideas it’s her. She creates, iterates and re-imagines on the fly and probably with her eyes closed (and in her sleep. Though judging by her EPIC content she probably has her eyes open in her sleep, too.) Her content is epic. And she’s passionate about helping us create epic stuff, too. Read more about Regina in How to be Successful.

Who are the successful entrepreneurs you admire and why?

If you enjoyed this article you might also like What is an Entrepreneur & What Type Are You? [even if you're still in the closet], How to be Successful and The Best Startup Books to Unleash Unstoppable You


Image: Allef Vinicius via

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