Legends & Losers - The Podcast Silicon Valley Needs

Legends & Losers - The Podcast Silicon Valley Needs header image 1

042: Beautiful Losers: Museum of Failure Founder Dr. Samuel West on Celebrating Losers

More and more companies fall out of the market because their fear of experiments and innovation drives stagnation in their development. What are they missing? How can we overcome our fear of failure and see it as a learning tool instead? What are the benefits of recognizing the need for innovation and creativity? All this and much more in this week's episode with Dr. Samuel West, who shares his experience and research on the benefits of failing.

You learn to walk by falling down - everything you know, you learn from failing. - Dr Samuel West


  1. We shouldn't be scared of failure - we should embrace it as it helps us learn.
  2. Companies that don't go with the flow of technology don't have a chance for success.
  3. Creativity and innovation are encouraged by spontaneity and fun in the workplace.

At the start of this episode, we talked to Dr. Samuel West about the importance of embracing failure as a chance to develop yourself and making your endeavors even more successful. Then Dr. West explained his concept behind his Museum of Failure and told us about some of the more interesting exhibits he's got on show. Afterwards, we got into the broader topic of introducing fun and improvisation into the workplace, discussing both the benefits and the risks of that model. Towards the end, Dr. West recapped why failure is an important asset to embrace and what constitutes a higher risk of failure.

Dr. West also talked about;

  • The public's favorites from the Museum of Failures
  • Why it's important for companies to be open to technological developments
  • The theoretical background behind encouraging both rationality and irrationality in the workplace
  • How not taking yourself seriously makes any activity easier
  • How the unique Silicon Valley ecosystem of recognizing failure contributes to success
  • The effect of politics and socio-economic policies on entrepreneurship in the US

As a society, we've been educated to fear failure and to avoid it for the sake of success. By avoiding opportunity for creativity and innovation because we're afraid of failing, we risk falling behind our competitors, who are swiftly moving with the times. Fun and doing things for the sake of it can sometimes lead to amazing, groundbreaking results - or not, but that's okay. Imitating big risk-takers such as Amazon and Google and encouraging a positive and proactive attitude towards failure can help any company or individual maximize their potential to the fullest.

Guest Bio:

California-born Dr. Samuel West is a licensed clinical psychologist and innovation researcher. As director and curator of the acclaimed Museum of Failure, Dr. West looks to explore some of the biggest failures of well-known companies. He has also delivered various workshops and keynotes on the art of learning from failure and is the author of several books on the subject. Dr. West's research interests revolve around the science of play and how playfulness can increase corporate productivity. Find out more about the Museum of Failure on MuseumofFailure.se. Visit Dr. West's website on SamuelWest.se.


041: Legendary Millennial Entrepreneurs

The millennial generation is shaping up to be the least entrepreneurial in history. What is driving this crisis in entrepreneurship, and making people not want to take risks? What are the biggest challenges the millennials have when it comes to running their business ventures? On this episode, we have a fantastic conversation with 3 young entrepreneurs winning in the game and making an impact.

Entrepreneurial tendencies and philosophies are great ways to live as a person. -Connor Gillivan


  1. The education most millennials received was based upon a pre-internet lifestyle and a pre-internet economy.
  2. If you increase revenue, all the other challenges become easier.
  3. A lot of young people would rather be broke and more fulfilled than rich and unhappy.
  4. Access to capital doesn’t necessarily mean giving up ownership anymore.

At the start of the show, Hector, Mani and Connor told their stories and shared what led them to take the entrepreneurial path. Next, we talked about the crisis in American entrepreneurship and why so few millennials are becoming entrepreneurs. We discussed the importance of meditation and having hard lines. We went onto discuss painting a compelling vision, and the new ways entrepreneurs can access capital.

We also spoke about

  • Why structure leads to freedom
  • The biggest challenges entrepreneurs are facing
  • The importance of grit, persistence and hunger

What’s holding people back from being entrepreneurs is the lack of preparation and having nothing driving them to want to take risks. For young people, the idea of improving yourself isn’t quite sexy yet, and the avenue to get there is through entrepreneurs. The old paradigm of working just for money is gone and how people want fulfillment and happiness. To succeed, structure is important, as well as being driven to succeed through the obstacles. The answer to the question, of becoming an entrepreneur is always yes.

Guest Bio

Hector Santiesteban
After training over 1500 Millennials in entrepreneurship and sales, Hector is focused on helping young people make money in a meaningful way. Go to MillennialSkills.com to find out more about his work.

Mani Vaya
Mani is the founder of 2000 Books. Prior to this, he spent 12 years in the tech industry and most recently was managing Billion dollar cellphone design projects at a Fortune 500 Tech giant. Go to 2000Books.com

Connor Gillivan
Connor is the CMO of FreeeUp and the best selling author of Free Up Your Business: 50 Secrets to Bootstrap Million Dollar Companies. He has been in the eCommerce industry for the past 7 years and has sold over $20 million worth of product. His advice can be found on leading publications and podcasts such as WebRetailer.com and Conscious Millionaire. Go to FreeeUp.com.


040: Becoming Really Famous Really FAST: How Surfer Zoltan Torkos Outshined Kelly Slater for 2 Weeks

With the surf kickflip, Zoltan Torkos went from surf news, to local news to national news and even to international news. What was the experience of becoming a sensation like? Why does he surf and enjoy teaching other people to surf? On this episode, we are joined by the man himself, the magician of surfing - Zoltan Torkos!

I think I’m a revolutionary surfer, and I should be out surfing and I shouldn’t be at school. - Zoltan Torkos


  1. Helping other people become better surfers is organic, and something that helps Zoltan connect with the ocean.
  2. There’s serious stuff going on in the world, surfing should be mellow, and people shouldn’t take it too seriously.
  3. When you’re surfing, you’re only competing with yourself, no one matters.

At the start of the show Zoltan talked about doing the surf kickflip, and the media sensation that happened after the video was uploaded and what Tony Hawk had to do with that. Next, we talked about his experiences after that moment, how he wanted to be the Evel Knievel of surfing and who he looks up to in the surfing game. Towards the end of the show, he gave us a magic trick!

We also spoke about

  • How the surf kickflip revolutionized surfing
  • Why it’s important to be nice to people in the water
  • How to be the best surfer in the water

A lot of people take surfing far too seriously, and start to look down on people who aren’t as skilled as they are. This takes away from the fact that we have to be there for each other and just have fun. You can’t be defined by the conditions, your equipment or whatever your skill level is, just get in the water and enjoy. If your surfing sucks, blame it on the board!

Guest Bio

Zoltan is a fourth generation magician, he performs in a realm beyond playing cards and rabbits in hats.  He brings magic to the art of surfing and a passion for change that is rare and sincere.  Born and raised in Santa Cruz, Zoltan recently made international headlines as the first person to be filmed successfully completing a kickflip while surfing. Go to for more information ZoltanTorkos.com.


039: Shaping A Legendary Business & A Legendary Life w/Quatro’s Master Shaper Keith Teboul

We’re in the era of widening appreciation of athletes who have broad capabilities. What lessons should younger athletes learn about life after all the games? How do people create a legendary business and a legendary life with your spouse? On this episode, we’re joined by all round waterman Keith Teboul who shares on coming up, losing it all and staying humble.

It’s the evolution of opportunities that came to me that I was able to see and take advantage of. - Keith Teboul


  1. Athletes struggle to transition into civilian life because they’ve had to be super focused on that one thing for a long time.
  2. If you’re married to a wonderful woman, accept that she’s going to be right most of the time.  
  3. There’s more to life than being an athlete.


At the start of the show, Keith shared on going to Marshall Islands and why he likes going there so much. Next, he talked about transitioning to civilian life as an athlete, and why so many people struggle with it. Keith also shared how bankruptcy affected him, and what he’s looking forward to in his future.  

Keith also spoke about;

  • His water sport heroes
  • Why staying open minded is super important
  • Being married to a fellow entrepreneur
  • The importance of quality relationships

 People want to be a part of something, and the people we look up to are here to provide that. Humility is important because that’s how they treat all they have with respect. For Keith, his happiness comes from making other people happy. Things in life, aren’t just meant to be, you have to see the opportunities and make choices. It’s important to enjoy your day and what you’re doing.  

Guest Bio

Sixteen dedicated years of playing with concaves, rails, rockers and fin set ups have earned Keith Teboul an undisputable reputation as one of the world’s top shapers. Keith’s skills on the water are equally impressive, widely respected for his progressive, fluid style, it is safe to say that Teboul is one of the major driving forces behind modern wave sailing today. Go to QuatroWindSurfing.com for more information.


038: Lead Like A Navy Seal: Chris Fussell On How To Empower Teams With One Mission

The secret of success in war time is our ability to communicate rapidly and create shared consciousness, and this also applies to business. How can you create this mindset among everyone in an organization? How did 9/11 change the military? What are the new levels of understanding the military needs? On this episode, we are joined by McChrystal Group partner, Chris Fussell, who gives insights into these questions.

The best senior leaders are the ones that are willing to admit that no single individual can handle the complexity of this world. -Chris Fussell


  1. The military has had to understand the magnitude of the changes that came with the information age.
  2. All the great leaders we put on pedestals have a dark side.
  3. Ask yourself how fast can you maneuver your big enterprise at peak speed.

At the start of the show, Chris shared how he got into the military, being inspired by his grandfather and father. He also shared how tough military training is, and why it has a lot to do with weeding people out. Next, we talked about how wrestling connects to MMA fighting and he also shared how the military changed after 9/11. Chris also shared what it’s like to be married while you’re on active duty, as well as how the military wasn’t prepared for the information age. We also discussed the work The McChrystal Group does, and towards the end of the show, we talked McGregor/Mayweather fight predictions.  

Chris also spoke about;

  • The importance of balance, strength, endurance, and physical readiness in the military
  • The power of operating as a high performance team
  • The secret of success in war time
  • How to be a servant leader

In the world we’re living in today, the rule books for solutions to the biggest problems can’t keep up with how fast the problems evolve. For leaders to succeed in this environment, it’s important to admit this complexity and then close the gap between optimal performance, and how fast these new networked problems can move. Sustainable success is about how fast the solutions occur. The best leaders are constantly coming in underneath the organization and staying on their feet to solve these new problems.

Guest Bio

Chris Fussell is a Partner at McChrystal Group, where he heads up the McChrystal Group Leadership Institute. Chris is an author of the 2015 New York Times bestseller, Team of Teams: New Rules of Engagement for a Complex World. Chris was commissioned as a Naval Officer in 1997, and spent the next 15 years on US Navy SEAL Teams, leading SEAL elements in combat zones around the globe. From war-torn Kosovo, to counter-terrorism operations in Iraq and Afghanistan, to highly specialized efforts in the troubled areas of the Arabian Peninsula and North Africa, he experienced and led through the modern evolution of the US military’s Special Operations community, first on SEAL Teams Two and Eight, then in the Naval Special Warfare Development Group. Find him on LinkedIn LinkedIn.com/in/Christopher-Fussell-56947a32


037: The Amazon Way: How John Rossman Designed the SECOND Amazon Category King w/ John Rossman

The networked economy creates abundance, not scarcity. Why is Amazon such a shining example of a company that managed to dominate within an abundant ecosystem? What opportunities can we create when customer experience stretches across companies? What are the opportunities that IoT has for leaders? On this episode, author and consultant John Rossman shares his insights, and gives us a look into what has made Amazon so powerful.

A platform business is a core capability that you could let others use to serve customers, they can leverage the business and innovate on top of it. -John Rossman


  1. Internal customers tend to be non-demanding customers.
  2. The best customer experiences now span across multiple companies.  
  3. Malls have to become about experiences, shopping needs to become an afterthought.
  4. Amazon won shoppers over by taking ownership of and accountability for the vendor-consumer relationship.

At the start of the show, John shared on being a consultant and why it’s different from being an “insultant”. Next he talked about the power of asking questions and what Amazon gets right, “while they are a financially aware company, they don’t do anything based on financial measures.” We went onto discuss platform businesses, how category kings create ecosystems, and the near-term opportunities IoT provides. Towards the end of the show, we discussed the “future press release”.

We also spoke about;

  • How the networked economy creates abundance
  • The power of taking responsibility for the customer experience
  • Self-publishing on Amazon
  • The importance of writing a narrative

A platform business allows a company to leverage the innovation, intent and skill force of lots of others without having to pay or direct them. The result of this is more creation, collaboration and the solving of problems and possibly the creation of categories. When a company allows this to happen, people have the freedom to try new things, and the market benefits. Leaders should ask themselves how to make their core capabilities good enough to be externalized.  The near-term opportunity for leaders when it comes to IoT is improving the programs you have by infusing more data with it.

Guest Bio 

John Rossman is the author of The Amazon Way: 14 Leadership Principles of the World’s Most Disruptive Company, and a Managing Director with Alvarez & Marsal in Seattle, specializing in technology strategy, multi-channel operations scaling and platform enablement in multiple industries including retail, service and public sector. Go to AlvarezandMarsal.com to find out more about John’s work, or JohnRossman.com/legends.



036: The Power of a Different Mind: Jamie Williamson on Learning Strategies to Manage & Exploit ADD, Dyslexia & More

Dyslexia is one of the most misunderstood learning differences. What are the biggest misconceptions people have about dyslexics? How can education work to nurture children who have it, and make sure they find their strengths? What approaches are used to teach children with learning differences? On this episode, Jamie Williamson of the Marburn Academy is here to discuss this, and provide learning strategies for children and parents.  

One of the biggest strengths dyslexics have is this conversation around resilience. -Jamie Williamson


  1. Dyslexia is a phonological processing disorder. People with it struggle to break a word down into different sounds.
  2. Active working memory refers to your ability to hold things, cognitively on your work space and then manipulate that information.
  3. Strengths are what you’re good at, affinities are what you love.

At the start of the show, Jamie shared what a learning difference is, and he also defined executive function. Next, we talked about the myths people have about dyslexia, including the idea that more boys have it than girls. Jamie also talked about how Marburn structure their lessons and classrooms, and towards the end of the show, he shared his own journey and the familial system community conversation.

Jamie also spoke about;

  • The connection between dyslexia and tenacity and persisting through things
  • What parents can do when their child has a learning difference
  • Organizational strategies to overcome difficulties

Every child in this world deserves an exceptional educational experience. Every child deserves to find their strengths and be celebrated for what makes them special, not brought down for being different. Educators and parents need to have good training around academics, and create a safe and nurturing environment for a child. Schools like Marburn create this by having small, intimate classrooms with two teachers, and having the children drive the conversation.

Guest Bio  

Jamie joined Marburn in 2015 and is Marburn’s 4th Head of School. Williamson is a graduate of Western Kentucky University with a Bachelor of Arts in Psychology and holds a Masters of Science and Education Specialist degree in School Psychology from Miami University. Go to MarburnAcademy.org for more information.


035: Design: Legendary Products, Brands, Businesses & Lives w/ Dennis Boyle of Ideo & Peggy Burke of 1185

We’re living in a time where people are concerned about machine learning and AI. Why are there more upsides than downsides? What is the opportunity for entrepreneurs as we look into the future? How can two people building big businesses have a beautiful marriage and partnership? On this episode, Peggy Burke and Dennis Boyle talk about designing their businesses and how they got to where they are today.

What’s going to happen is like opening up the black box and all of this incredible inspiration is going to come out as a result. -Peggy Burke


  1. Working couples: you have to get help and you have spend time with each other, if you don’t, you won’t make it.
  2. If you hide your knowledge, it won’t to be as useful as when you spread it.
  3. Radical collaboration: work closely with the internal team, they understand how the process works.

At the start of the show, Dennis and Peggy shared how they met, the history of their companies, and how they were able to raise their family while building their companies. We also spoke about radical collaboration, and taking time to get used to new technologies, and why nice guys actually finish first.

Dennis and Peggy also spoke about;

  • The impact the agility of IDEO has on the business
  • The processes and culture of 1185
  • The upside of technologies like AI and machine learning
  • The power of building an artist-patron relationship with clients

The biggest opportunity for entrepreneurs, looking into the future is tapping into the labor force that is most likely to lose their jobs and turning it into a happy, fulfilled part of the population. The solution isn’t socialism, but rather it’s entrepreneurism. IDEO and 1185 have stayed in business as long as they have by differentiating on their intellectual capital and doing really good work. As an ambitious couple, you have get help because you can’t be super humans all of the time. That’s how Dennis and Peggy built such a legendary life!

Guest Bio

Dennis Boyle is one of the founding members of the design and innovation firm IDEO and has worked as a project leader for many of the firm’s start-up and established clients including Apple, Palm, Tivo, Handspring, HP, Dell, Procter and Gamble, and others. Dennis is now one of the leaders of the Health and Wellness practice at IDEO. Mr. Boyle is also a Consulting Assistant Professor at Stanford and teaches classes in the Design Division of the ME department. Go to Ideo.com/people/Dennis-Boyle for more information.

Peggy Burke is the founder and CEO of 1185 Design, an award-winning graphic design firm specializing in corporate branding, websites and packaging for high-tech firms. She has done extensive work for Fortune 100 companies including Adobe Systems, Cisco Systems, IBM and Sun Microsystems. Go to 1185design.com for more information.


034: Don’t Believe Everything You Think: Dushka Zapata, Best SellingAuthor on Overcoming Fear, Dread & Limitations

The assumption that imagining the worst case scenario prepares you is a fallacy. What do we get wrong when it comes to dealing with fear? How do we distinguish between the types of fear we experience? What happens when what we think is true turns out to not be? On this episode, Dushka Zapata is back to share more of her wisdom, great writing and her perspective on how we overcome the things that hold us back.

The reason we believe in things that aren’t true is we listen to our fears, and we listen to our fears because that’s what keeps us safe. - Dushka Zapata


  1. You need to not believe everything you think. A lot of what we believed is governed by our fears because we’re wired that way.
  2. There are two kinds of fear, one feels like dread telling you something is dangerous, and the other is a more thrilling feeling.
  3. People either love you or they don’t, you don’t have to do anything to make them love you any more.

At the start of the show, Dushka talked about political correctness and her upcoming book “A Spectacular Catastrophe and Other Things I Recommend”. Next, we talked about how most people feel like misfits, and why we have to change the way we view ourselves. Dushka also talked about how we can become trapped by the things we believe, and how to distinguish between your fears. Towards the end of the show, we talked about what we get wrong about love and friendship.

Dushka also spoke about;

  • Disbelieving things you always thought were true
  • How attitude tells your brain what to see
  • How to stop paying attention to the limitations in your mind
  • Useful coaching

We go through life believing things and the fact that we believe them hurt us. We listen to our fears because we’re wired to keep ourselves safe. To overcome our fears, we have to defy the mechanism inside that keeps us safe when we’re experiencing an unknown. There’s the fear the makes you feel dread and the fear that is more thrilling. Human beings can have conversations and declare that things can be different and we should take advantage of it. Remember, we create reality with our thoughts, so we can bend it with our thoughts. That’s how we summon the courage to overcome.

Guest Bio

Dushka helps companies and people put into simple terms who they are, what they do, and where to go next. Her work comes to life through message development, presentation training, media training and personal brand development. It comes to life through executive coaching, workshops and public speaking. It comes to life through what she writes. Her first book is "How to be Ferociously Happy" and her second is titled "Amateur". Her third and newest book is "A Spectacular Catastrophe and other things I recommend". Find her work on Quora.com/profile/Dushka-Zapata or buy her books here https://www.amazon.com/Dushka-Zapata/e/B01F2GZVYQ.


033: How To Be A #1 Salesperson, Entrepreneur, Leadership Guru & Ultra-Marathoner w/Jon Berghoff

Human beings are very good at talking about what’s broken, what’s not working and what’s wrong. What is appreciative inquiry? How does it help companies reframe their problems and how they engage with employees in a meaningful way? What leadership lessons can we learn from this experience? On this episode, Jon Berghoff talks about his life, becoming a leading salesperson and coach, as well as changing the lenses and conversations we are having about work.


If 7/10 people don’t like going to work, maybe we need a new paradigm for how we approach work. - Jon Berghoff



Sensory clarity is the ability to distinguish your internal experience of the external world.

Languaging creates thinking and thinking creates action.

Leaders have to realize they don’t have all the answers. Their people have the answers, so it’s important to trust their wisdom.

You can’t solve a problem without having as many relevant voices in the room when you’re having the discussion.

At the start of the show, Jon shared how he got into ultra-marathons, and how he made ADHD an advantage. Next, he shared on unified mindfulness and how his career got started. We then began talking about appreciative enquiry and the current conversations we have about work, businesses and companies. We also discussed how so many people are seeing life through lenses cast on them by other people, and how to overcome that by changing what we say and what we think. Towards the end of the show, we discussed what companies get wrong when they try to bring a playful environment into the workplace.

We also spoke about;

  • The difference between pain and injury
  • Why the term “work-life balance” is BS
  • The importance of inclusivity in company discussions
  • Why giftology is so necessary

We’re living in an age of accelerated change, and that change includes disconnectedness. This lack of connection affects our relationships and if affects our companies. Appreciative inquiry is the ability to recognize that there’s power to wholeness and connectedness. Companies can’t solve a problem without having as many relevant voices in the room when they have important discussions. Leaders have to realize that every voice adds wholeness to the story they're telling. When the values are in place, and people are clear on the mission, it brings energy into the room. What we need is a collective dialogue that is intentionally designed to move us towards something positive.

Guest Bio

Jon is the co-founder and managing partner of FLI. Under Jon's leadership, the FLI team has designed and facilitated whole-system change efforts, through large group collaborative summits for organizations that include Fathom, Boeing Corporation, Vitamix Corporation, Fortec Medical, and Fairmount Minerals. Jon previously served as the head of sales for the direct sales team at Vitamix Corporation, where revenue grew by 400% in less than 4 years, as their team grew from 175 to over 600 members. His work in Appreciative Leadership, Emotionally Intelligent Negotiations, and Influence has brought him to Australia, Japan, the UK, and South America. Jon is in high demand, known for his authenticity and highly engaging style of creating powerful learning experiences for participants. Go to http://www.lead2flourish.com/ for more information.