Legends & Losers - Motivational Business Dialogues, With an Edge

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127: “This Week in Business” #3

This Week in Business, we are joined by the great Heather Clancy of GreenBiz Group!

We talk:

- AirBnB going upstream

- bad Super Bowl commercials

- "Niching Down" so you can dominate your category


Don't miss it!


126: NBA Legend and Grateful Dead Hall of Famer Bill Walton on Living in a World of Yes

In life, things can go wrong and collapse. No one understands this better than Bill Walton. How has he been able to overcome the challenges he’s faced? Who are the men and women who have inspired him on his journey to success? How does it feel to be in the Grateful Dead Hall of Fame? On this episode, we talk to the legend himself as he shares why he loves what his life is all about.

I have learned to never rank or compare concerts, coaches, children, championships or congratulations. Just enjoy them all. -Bill Walton

3 Things We Learned

Teachers and Culture are Necessary to Success

When you have a goal or want to get somewhere, you must have the dream. You need a teacher who has been where you want to go. You also need to have the culture that drives all of it forward and determines your behavior.   

Sacrifice and discipline breed success

What holds humanity back are negative elements like greed, selfishness and brutality. If we are willing sacrifice to see a greater goal and purpose, we can not only eliminate the negativity but also find success.

Bill Walton’s mindset on technology

If we don’t use technology to eliminate our waste problem and continue polluting and destroying everything, we’re just going to kill ourselves.  


We live in world that insists and demands qualitative binary decision-making. This is a mistake because people always want yes or no. We can choose to live in a world where we are constantly hopeful and expecting good things. The primary focus of a leader is to illuminate the path forward, have the ability to articulate the message and show people how to get to a better place. We can lead the charge in changing how the world thinks and hopes. In Bill’s words, “Hope and expectations are driving forces in my life.”


125 Unlocked: Elon Musk’s Greatest Achievement Is Not a Rocket

With SpaceX’s successful (or unsuccessful demanding on what happens!) launch of a new super-powered rocket, all eyes are on Elon Musk. 

Like all great innovators, Musk is achieving two things at the same time.  


First he’s creating new technologies, businesses and categories-- and massive new wealth as a result. 

Awesome. That’s what entrepreneurs are supposed to do.  But, his role in our world is bigger than any one new thing he’s creating. 


Elon Musk stands as an icon of possibility. 


He has the audacity to dream big.  And now, more than ever, he’s reminding Americans what can be achieved when you “swing for the fences.” 

American entrepreneurship is in a lot of trouble. Never has the U.S.A. needed a legendary entrepreneur like Elon to show us the way.  

We need to be reminded that it is okay to, as my friend, “the most powerful woman in startups”, Ann Miura-Ko says, “have BIG dreams.” 


You see, entrepreneurship is at an all-time low in the U.S.  


Yes, that’s right. And I couldn’t believe it either.  Even though entrepreneurs are celebrated as rockstars, the data shows entrepreneurship in America dying. 

Making matters worse: “Millennials are on track to be the least entrepreneurial generation in the past 100 years.”  

This is a giant fucking problem.  


Where are the breakthroughs and jobs going to come from? 

Sure; government, universities, think tanks and big business all play important roles in our forward progress, but new businesses and small businesses are seminal.  

Entrepreneurs build our world.  


New businesses and small businesses are pivotal drivers of human innovation, economic growth, and jobs.  

The U.S. Small Business Administration says: 

  • companies with fewer than 500 employees account for 99.7% of all business in the US. 
  • 64%of net new private-sector jobs come from small business 
  • new/small businesses produce 16 times more patents per employee than large outfits.  


Entrepreneurs are the people who take great risks to make great contributions 

Entrepreneurs are the people with the courage to stand in the face of no evidence that their idea will work, and go for it any way 

Entrepreneurs are the people who slay cynicism with dreams. 


Which brings us back to Elon 


His greatest contribution is how he inspires people. Elon Musk is teaching us all how to take “crazy” ideas and make them real. 

So regardless of the successes or failures Musk has, just like Edison, Ford or Jobs he’s showing us what’s possible. 

He’s demonstrating us how entrepreneurship can move the world. 


Thanks, Elon. 


124: A Remarkable Conversation About Love w/Bix Bickson

Love is the thing we all deeply hunger for in our lives. Why are we so attracted, mesmerized, and blinded by love? How can you choose to love without getting caught up in the BS? What is the difference between choosing and deciding? On this episode, Bix Bickson is back to give us some powerful insights on the mystery and miracle that is love.

The world says we give to the people we love, but we actually love those to whom we give. -Bix Bickson

3 Things We Learned

The big lie on the planet is that we’re not connected

The truth is we’re all hungering for the deepest connection we can possibly make with one another, and that’s something that actually unites us.


There’s a distinction between deciding and choosing

The word decision creates a context that we do something based on external factors and circumstances. Choice is different; it’s based on doing something from our internal feelings. When we choose, we select freely after consideration.


A lot of relationships are based on ‘reasons and stuff’

We calculate the quality of our relationships on ‘reasons and stuff’, but when you’re in a relationship for an extended period of time, those reasons and that stuff disappear quickly. The question is, when that’s no longer there, are you there for love?  


We won’t always have feelings of love for our loved ones from moment to moment, but we can choose to experience love by accepting them for who they are, and not get caught up in the little things that annoy us. We can teach ourselves to return to the feeling of love and continue loving that person for who they are and who they are not. This makes us happier, and makes love more rewarding.

Guest Bio

Bix’s work includes executive consultation and coaching, organizational design and development and engaging and aligning people on every level in the organization. Send an email to bix@bixbickson.com for more information or follow him on Twitter https://twitter.com/bickstweet.


123: An Unpredictable Conversation About Love w/Dushka Zapata

In our world, the unspoken paradigm is that we have a finite amount of love and must allocate it accordingly. How does this negate the best parts of us? How can polyamorous people love more than one person? Can you crush on someone even if you’re in a relationship? On this episode, Dushka Zapata and I have a dialogue on heart multiplicity; a topic we don’t hear enough about.

The very best part of us is the fact that we do not have a limited amount of love. -Dushka Zapata


3 Things We Learned

There’s no such thing as weird, and there’s no such thing as normal

There are so many feelings we have that we keep hidden because we think they are weird. If we were less silent about the things we consider weird, we would find that it’s usually a universal condition. We’re not weird: we just express who we are so as to gravitate towards what is looking for us.

There’s a difference between suicide ideation and the contemplation of your mortality

There are two separate things: one is suicidal fantasies or self-sabotaging, but there is something else entirely that is universal. It’s the act of toying with your mortality, and it’s called L'appel du vide or the “call of the void”.

Give permission to your feelings

For some people, having feelings for more than one person is something fleeting and they can’t love more than one romantic partners. Others choose to be polyamorous and share their love. There’s no right or wrong way of doing things. The key is knowing your truth and not being ashamed of your feelings.



Our hearts have an expansive ability to love, but we’re conditioned to think that our capacity for love is finite. We can love many people, and each love can be its own sovereign universe. We should consider it a privilege to be granted expanding hearts. There’s no need to use our energy in the wrong direction. We can give ourselves permission to have our feelings without fear that it will threaten our relationships.


122: Six Minutes of Legendary

Insightful, inspirational moments from Legends & Losers.


121: The Future of Content: Charles Wachter on Hollywood, Silicon Valley & Creating Massively Popular Content

Netflix plans to spend $8 billion in content in 2018. Are apps the future of TV? How are content and branding starting to merge? How do content creators feed the hungry market of consumers? On this episode we are joined by super executive producer Charles Wachter, who shares on the changing landscape of TV and entertainment, navigating the distance between marketing goals and entertainment goals, and being a content creator in the era of Netflix.


Twenty to thirty years ago, there were very few who held the keys to entertainment kingdom. -Charles Wachter

3 Things We Learned

Self-marketing shows sell

If you’re at the point where your success markets itself, you have a way to go directly to the consumer, and you’re able to maintain that success-- you’re going to see the upside.


There are universal things the audience gravitates toward

To create content that is both good and able to become a hit, you have to be able to make the audience feel something, make them laugh, take them away, or shock them.  


Long-running shows have perfected the art of branding and pleasing the audience

Shows like “Law & Order” have been on TV for almost two decades. Even though every trope has been played out, and the plots are predictable, these shows have survived because they will always be a comfort to viewers.


Years ago, traditional TV networks were upended by the advent of cable. Now in a similar way, apps and streaming services are upending modern television as we know it, including how deals are brokered and made. Before this era, very few companies controlled the creation and distribution of content. Now there are thousands of content streams, and the power players are the ones who own large sections of that market. This presents a great deal of opportunity for content creators who are able to play in different arenas and access deals that are favorable. Content that markets itself is what sells the most right now.

Guest Bio

Charles is an executive producer and showrunner. He has produced TV series including Jamie Oliver’s Food Revolution, American Gladiators, King of the Nerds, Fear Factor and Fashion Star. Charles recently teamed up with global indie studio Propagate Content to launch Hard Twenty, a new production company.


119: Sebastian Junger on Purpose, Belonging & Being Part of a Tribe

This country doesn’t feel like much of a community right now. How do wealth and affluence play into our lack of connectedness? Why is it dangerous for us to lack tribes in our society? How did we become a self-absorbed nation? On this episode, I have a dialogue with journalist and author, Sebastian Junger about implementing ideas of the tribe in our lives, and connecting for our survival.

3 Things We Learned


Lack of connectedness is part of what makes transitioning out of military life so difficult.

Soldiers have to transition from being in a close-knit community to modern society where there are no cohesive units. This creates isolation, which leads to depression, PTSD and loneliness. In countries where military service is mandatory, people experience less of this because everyone else understands the experience.


Affluent suburbs are dehumanizing and drive isolation.

Lower income neighborhoods foster more of a familial community than affluent suburbs where people are more likely to keep to themselves. Unfortunately this actually makes us a lot worse and slowly drains us of our humanity. In modern society, wealth and security has made us need each other less but we actually need to be in tribes.


People slip into addictive behaviors because they are unhappy.

What’s causing the opioid crisis in America is the fact that people just aren’t happy. People feel lonely, isolated and like they have no meaning. In response, they numb themselves with substances.


There is a profound change in one’s life when you go from just being another brick in the wall in a large group of people, to feeling like you’re part of a community. We are wired to thrive within a tribe, and when we don’t have this, it takes away from the quality of our lives and general mental health. The point of life is to be as happy as possible, and that isn’t just about money. It’s also about placing a value on human connection and contributing to society. We have to have a deliberate conversation about this, because ultimately it will make us feel more united, and make the whole world better.

Guest Bio

Sebastian Junger is the #1 New York Times Bestselling author of THE PERFECT STORM, FIRE, A DEATH IN BELMONT, WAR and TRIBE.   As an award-winning journalist, a contributing editor to Vanity Fair and a special correspondent at ABC News, he has covered major international news stories around the world, and has received both a National Magazine Award and a Peabody Award. Junger is also a documentary filmmaker whose debut film "Restrepo", a feature-length documentary (co-directed with Tim Hetherington), was nominated for an Academy Award and won the Grand Jury Prize at Sundance. Go to http://www.sebastianjunger.com/ for more information.


118: “This Week In Business” #2

 This Week's Topics:

  • The Stupid Bowl
  • Is Facebook A Cigarette?
  • Amazon-A-GO-Go
  • Davos: “What Everyone is Talking About”
  • Flipping For Net Neutrality
  • Proof: Category Potential Drives Market Cap
  • Apple: there goes a trillion
  • A loser Bank brand