Legends & Losers: One real conversation can change your life.

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134: Forbes “40 Women to Watch” Wendi Sturgis on Building a Legendary Career

A legendary career will have both winning and losing moments. What are some of the lessons you learn on the way to your dream job? What are means-to-an-end jobs and why are they so important? How do you become aware of what you’re worth? On this episode, I have a dialogue with one of my colleagues from Scient, Wendi Sturgis, who imparts powerful wisdom for navigating the highs and lows of life, career, and the market.

Know what’s most important to you next. Is it the title, the responsibility, the role or the money? -Wendi Sturgis

3 Things We Learned

Get comfortable with the money discussion

Money is a conversation so many of us are uncomfortable with, and this bleeds into how we ask to get paid what we’re worth. Get comfortable with talking about it with your close confidants because if you don’t, you won’t be able to have the conversation with someone who doesn’t know you.

Sometimes you’re going to have “means-to-an-end” jobs

In our career trajectory we’re going to have dreams jobs that are the ultimate goal, but some jobs will just be pitstops. These are important because they teach us more about what we really want, and lead us closer towards that ultimate job.

Being a next-level executive is all about knowing when and how to push

You can’t bulldoze your way through things when you’re running an organization with billions in it. You have to find the right leadership team and the ways to set the right strategic direction.


Life has a great duality to it. You will experience ups and downs and have legendary moments and losing moments. It’s so critical that you know what your worth is and surround yourself with the right people. When you know your value and your North Star, you will be able to navigate life while taking lessons where you get them and growing every step of the way. This is what will help you determine your next move and execute it gracefully.


133: “The House that Spied on Me” w/Kashmir Hill & Surya Mattu

Our homes have always been sacred and private spaces until they became “smart”. What data is produced by our smart devices and how is it used? Is sacrificing our privacy worth all the tracking and data gathering? Is the data innocuous or is Big Brother really watching our every move? On this episode, the writers of the brilliant Gizmodo story, “The House that Spied on Me” are here to discuss the experience of having over 15 smart devices in the home and what it taught them about data, the accountability of data companies, and whether or not smart devices actually improve our lives.


Usually the modern contract is that we trade privacy for convenience, but living in the smart home I felt like I was trading privacy and convenience. -Kashmir Hill

3 Things We Learned

Data can be used to incentivize, but it can also be used to penalize us

Data broker companies are like insurance companies. They are trying to minimize risk and maximize profits. The more data they have on you, the more structures they can set up for rewarding you or incentivizing you. However, that means they can also penalize you for not doing something.

Smart devices aren’t as regulated as we’d hope they are

The fallacy in the surveillance conversation is that we think things are more regulated than they actually are. If we consider the fact that very few people actually know what the data is and how it is being used, we realize that there isn’t enough oversight on companies that handle all this personal information.

Net neutrality has moved backwards because of the money that’s now in data

You would think that our advancements in technology and the internet would mean we would uphold net neutrality as the gold standard, but the opposite is happening. This is because in the past, big companies didn’t know how to make money off the internet. Now they do.


We’ve been taught to believe that our homes being tracked makes our lives more convenient and easy, but it’s a huge tradeoff if we consider the amount of privacy we give up in the process. This smart home experiment shows us that these devices aren't providing the benefits a smartphone would-- so maybe sacrificing all this data isn't worth the information we’re getting. This is all information that can be used to study us behaviorally and teach us more about ourselves, but it can also be monetized and sold to big corporations. This tells us that the consideration to bring smart devices into our homes is one we have to take very seriously.


Guest Bio

Kashmir Hill is a senior reporter for the Special Projects Desk, which produces investigative work across all of Gizmodo Media Group's web sites. She writes about privacy and technology. Follow her on Twitter @kashhill

Surya Mattu is the data reporter at the Special Projects Desk which produces investigative work across all of Gizmodo Media Group's web sites. Follow him on Twitter @suryamattu

To read the full story go to: https://gizmodo.com/the-house-that-spied-on-me-1822429852


131: Cussing & The Power of Language w/Benjamin Bergen, the Swearing Professor

Human beings study language and the mind typically without including profanity, and that leaves out a huge part of language. What does cussing teach us about history, human behavior and how we relate to each other? How do people navigate contextual and situational environments when it comes to swearing? On this episode, Benjamin Bergen is here to talk about studying swear words, and learning more about people through them.

Having a word for something creates a category to hang stuff on. -Benjamin Bergen


3 Things We Learned

Kids understand the context of language better than we think

Most people understand the contextual and situational environment of when certain words can be spoken. That’s why we can find swearing at a comedy club acceptable, while we wouldn’t accept a CEO swearing in a board meeting. This is something even our own children understand.

Swearing comes with some interesting perceptions

When you swear, people perceive you as more honest, authentic and comfortable with yourself. At the same time, you can be perceived as less in control, intelligent and literate. It all just depends on where you are and who you’re with.

Words young Americans find offensive

Younger people find slurs more offensive than swear words. They don’t like derogatory terms for people based on sexual orientation, ethnicity, and religion.



Language is a huge component of culture and personal identity. The language we grow up with is your language for life. When it comes to swearing, we learn a lot about human behavior, our sense of morality and how different generations find different words profane. Usually a word takes the trajectory of going from being normal, then being brought to judgment, and over time becoming offensive. In many cases, certain words will rotate out with the passage of time, and new words become profane. This is how they change over time from generation to generation.

Guest Bio

Benjamin Bergen is the author of What the F: What Swearing Reveals About Our Language, Our Brains, and Ourselves. You can find it here!


129: Branding Icon: From Surf Bum to Business Pirate w/Santa Cruz Legend Rich Novak

Rich Novak is such a legend he actually has the rights to the name Santa Cruz. What is it like to build brands that have become synonymous with the city? How did he contribute to the skateboard industry in major ways? On this episode business pirate, branding genius, co-founder of Thrasher Magazine and early pioneer of the surf, skateboard and mountain biking industry, Rich Novak, talks about his legendary life.

I’m more into the deal of taking care of my workers and having a longevity to it. -Rich Novak

3 Things We Learned

Respect the craft

A lot of surfers don’t think about the work it takes to build and design a great board, so they don’t mind going really cheap. If you want to be a surfer, you have to support the craftsmen of the surfing industry

It’s great to grow big, but only to a certain extent in the clothing business

The formula for clothing in Southern California is this: you want to grow it only so big that you don’t lose your marketing and advertising techniques. You don’t want to exceed the 400 million mark because the it turns you on to the clothing merchants in New York and that changes everything. By going the way of Billabong and Quicksilver, you expose yourself to big money brands who don’t care about the customer or the product. They care about paying their shareholders.

Don’t be Afraid to Try Different Jobs

In order to design a life that you love, it’s important to be okay with the fact that you might do some jobs you don’t like on the way there. You have to do a lot of different jobs so you know what you don’t want to do. So don’t be afraid to wash dishes or dig holes. If you’re smart you won’t do that very long.


A lot of people surf but few have built their entire life around it like Rich has. He basically designed a life around surfing and his love for it, and along with that, built legendary companies and legendary categories. Instead of selling his brands to big money publicly-held companies, he chooses to hang onto innovation, workers and customers. The result is an iconic brand and an unforgettable legacy.


128 Unlocked: Hustle is for Losers

“Hustle” is the most prominent advice today for entrepreneurs. 

And Hustle is For Losers. 

Let me share why with some learnings from our guests. 


For 3 reasons: 

1) If you are or want to be an entrepreneur and you need to be told to work hard you should go get “a good government job”, not start a company! 

2) If you’re hustling in a shitty category, it's a waste of your talent. 

  • Categories make companies.  
  • Design your own category.
  • Be known for one thing you can own. 


3) Category queen economics apply. 

  • We live in a winner take all world
  • Category queens / kings in tech earn 76% of the total value in the space 


What should wanapreneurs and entrepreneurs think about?   

1) Struggle NOT Hustle: 

    Struggle (Verb) Google: “strive to achieve or attain something in the face of difficulty or resistance.” 

  • Our friend and guest Erik Weihenmayer, the first blind person to summit Everest (episode 48) says, “Life is a storm."
  • Erik: “The dichotomy is that people want to be in that storm... even though it’s scary. That’s where the action is, that’s where the excitement is, that’s where the discovery is, that’s where insight is.”  

2) Our friend and guest, Ann Miura-Ko who Forbes calls, “the most powerful women in startups, says, “Have Big Dreams” 

3) Her partner, also our friend and guest Mike Maples, Jr. says: “The first thing that I like to emphasize to people when they start a company is:  start a company that’s worthy of your talents, that you think represents the absolute utmost gift you have to offer to this world and your life.” 


In completion: 

  • Hustle is for losers 
  • Struggle in a category of your own design. 
  • Niche down, (be known for one thing you can own) to fulfill your biggest dreams by doing work that is worthy of your talent. 

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.