It’s been a wild and exciting ride on Legends and Losers, and we’ve reached 100 episodes! What are some of the biggest takeaways from the experience so far? What are some key insights we have about technology, startups and entrepreneurship? Why is “follow your passion” such bad advice? On this episode, we celebrate 100 legendary shows with a legendary dialogue.

How much you make is directly related to the value you provide to other human beings in the world. -Matt Johnson

3 Things We Learned

Innovation is going to go on steroids

So much has changed for us in this age, but we’ve only just seen the tip of the iceberg. In the next 15 years, we’re going to go through a hyper innovation cycle. By the year 2032, we’re going to look back to today and feel like it was the Stone Age.

Is this the end of the internet startup?

We haven’t had a big category king since Facebook and VCs just aren’t funding early stage companies as much as they did before. Startups have to scrape and scrounge before they can even get any VC involvement. What we’re seeing now more than ever is that VCs are funding companies that are in later stages of development, and in an emergent category.

The underrepresentation of women and minorities in business is costing the country billions

Certain demographic groups are underrepresented in the entrepreneur economy and it’s leaving a gap in business. If minorities started and operated startups at the same level as non-minorities, the US would have more than a million additional employer businesses and 9 and a half million more jobs. Women are half as likely as men to own a business that employs people and this consistent gender gap costs the country 1.7 million additional businesses.  

Entrepreneurship in America is still not as high as it was before the recession and there’s still work to do to open it up to women, minorities and people who don’t have a formal education. If we do this, we could see almost 2 million new businesses, and over 9 million jobs created. Additionally, we have to encourage entrepreneurship the right way, and stop telling people to just hustle or follow their passion. Our mission to contribute to this is ongoing endeavor.

Many people of color struggle to find where they belong and what resonates with them, because their races are rarely portrayed beyond stereotypes in the media. Who decides which stories get amplified? How do we make sure the voices of these people are seen and heard? How do we build a generation of creators, not just consumers? On this episode, we are joined by the founder of BAYCAT, Villy Wang, who shares on growing up in a world where she felt the story that represented her was omitted, how she found her voice and sense of belonging, and how she’s helping other people find theirs too.

Our stories weren’t lifted and they weren’t repeated with curiosity and with pride. -Villy Wang

Takeaways

• At some stage of our life, each of us is “pre-disabled”, whether we’re a baby, injured, or pregnant. Making mobility easier for everyone will make the world a better place.

At the start of the show, Villy shared on a project she’s currently working on. We also discussed her TED Talk, an event she shared in her speech, and her experience growing up in the melting pot of New York. Next we talked about racism in today’s world and how we can overcome it. We also discussed how monetization gets in the way of amplifying people’s stories and voices. Towards the end of the show, Villy shared why it’s so important to help people find their purpose.

We also spoke about:

• Why we need to close the technological divide

Everyone in this world wants to connect, belong, and feel like their story is important. When people’s stories get omitted, we rob the world of something necessary-- a rich, diverse truth of human existence. When nothing resonates with you, it’s hard to figure out where you belong. The gap that has been created by technology can either be inclusive or continuously divisive. If we fight for inclusiveness, we can enable the kind of justice and equality that will make the world a better place.

Guest Bio
Villy is the founder and CEO of BAYCAT, a nonprofit social enterprise that provides access, education and employment for low income youth, youth of color, and young women. Villy had a crazy dream: to create a new kind of social enterprise that helps kids who, like her, grew up in the projects. Raised by an immigrant single mother in New York City, Villy’s desire to tell her story forged a passion for using the digital media arts to capture stories untold and to create social change. That’s why she founded BAYCAT, leveraging her impressive 25-year background in education, arts programming, nonprofit business and law. Go to https://baycat.

What really causes poverty? Can achievement co-exist with social good? What are the best practices for social entrepreneurship? We turned to Tom Bagamane, founder of The Giving Spirit, for his perspective. Tom has built one of the largest all-volunteer organizations in the country, while also launching successful brands and building a socially-conscious consulting business. Here are the top 3 things we learned from Tom on homelessness, business and social entrepreneurship.

Achievement & Social Good CAN Co-Exist

“I often tell my friends…I’m a capitalist by day, and a philanthropist by night.” Tom applied entrepreneurial approach to philanthropy to attack a very tough problem on multiple fronts. By providing for both immediate physical needs of the homeless, while giving opportunities to get back on their feet and into the workforce, Tom has proven that you can do extremely well in business while doing good for your community.

Caring is Good Business  

It’s easy to neglect our existing customers in the pursuit of new ones. By focusing on nurturing and retaining existing customers over acquiring new ones, we can create win-win scenarios for our customers and generate enduring loyalty. Ultimately, this strategy is less costly and more sustainable than the hamster wheel of high churn and high customer acquisition costs.

To Truly Do Good, Seek First to Understand

Taking care of the homeless is not as simple as giving them a home. Tom points out, “As we’ve found out over 18 years, these people have lost their ability to understand what it’s like to sleep on a bed….We train to the norms that we take for granted. So how do we solve this? We put a roof over their head, and then we teach other.” There are some incredible, almost unbelievable, examples of homeless being given a home and a bed, and workers coming back a week later to find them sleeping on the floor next to the bed. We cannot simply give and then turn a blind eye to the results of our giving. We must meet people where they are, seek to understand them, and work with them to truly improve their circumstances.

As more entrepreneurs enter the nonprofit world, there are both opportunities and pitfalls. Social entrepreneurship ideas can streamline operations and boost donations, but lasting impact demands more from us. We must constantly ask, “Are we really helping those we seek to help?” It takes a commitment to feedback and monitoring results, then making critical adjustments, to create sustainable change and lasting impact.

Guest Bio

Tom Bagamane, social entrepreneur, brand developer, philanthropist and educator, founded the Giving Spirit in 1999. Moved to action by the plight of the homeless and lack of effective relief efforts, Tom’s organization delivers acute and emergent survival systems to those in desperate need in Los Angeles. It has gone on to serve over 43,000 souls and become one of the largest all-volunteer organizations in the US. Tom is also the Managing Director of Profitable Good Consulting Group (PGCG), a strategic consulting firm focused on working with companies t...

Today’s business environment is a lot like the battlefield. It’s volatile, uncertain, complex, and it requires agility. What are the mindsets, disciplines, practices and actions that a warrior and business leader should have so they are able to dominate and be in control? Why is it so powerful to have the ability to control your arousal response and have a daily imperative to develop yourself? What is the next domain of leadership development? On this episode, Mark Divine is back to give us deep insights on the warrior discipline of physical, mental and emotional control.

A warrior is someone who took a great amount of time and energy to master themselves at a physical, mental, emotional and even at a spiritual level. -Mark Divine

Takeaways

• Do box breathing for 20 minutes a day. 5 minutes will make an impact but 20 minutes will transform you.

At the start of the show, Mark talked about the different kinds of warriors we have in the world, and he gave a more clarified and rarified concept of the warrior. Next, he talked about why a warrior’s skills with weapons are secondary to self-mastery, and why the new structures of business and developments like the internet have made the landscape more like a battlefield. We also talked about the sheepdog mentality and why it’s so important, and the skills and practices you have to master in order to thrive on the battlefield. Towards the end, we talked about how Jeff Bezos has merged philanthropy with entrepreneurship and venture capitalism.

We also spoke about:

• The ramifications of not being a category designer

Business leadership today looks a lot like warriorship. You have to have a refined mind to be mentally and emotionally in control in this environment. It’s about being able to lead effectively in in complex and dangerous situations, and ultimately it’s about mastery of the self, in service to something higher. The brain is the body, and if the body isn’t functioning properly, your thinking is going to be distorted, you’ll have trouble focusing on the right thing at the right time for the right reasons, which will get in the way of your dominating. The ladder of vertical development is what should matter to us. It’s when we can take active control of our life and development by mastering all the skills of the athlete, the leader, the scholar, the statesman and the monk through the practice of a daily discipline.

Guest Bio

Mark is the founder and CEO of SEALFIT, and a highly sought after speaker, coach, author who makes frequent media appearances to discuss Seal way of life.

Small talk is easy for extroverts but difficult for introverts. What are some of the other big differences between these types of people, and where they get their energy? What misconceptions do we have about introverts? What is the difference between happiness and comfort? On this episode, Dushka Zapata shares on communicating, cohabitating and collaborating with introverts.

Labelling yourself doesn’t matter. What matters is understanding yourself and knowing yourself. -Dushka Zapata

Takeaways

• A dead giveaway of an introvert is that they usually don’t pick up their phone, they want to text or want to get back to you once they are ready.

At the start of the show, we talked about some of the misconceptions people have about introverts, and why it’s less about labels and more about understanding yourself. Next, we talk about the importance of networking in a way that plays to your strengths. We also discussed what might be causing the opioid epidemic and what it has to do with people not wanting to feel. Towards the end of the show Dushku shared tips for better communication and understanding between introverts and extroverts.

We also discussed:

• The difference between preference and choice

Introverts and extroverts just differ on where they get their energy from. It doesn’t mean being one is better than the other. The key is just understanding what depletes you, because that allows you to present the best version of yourself to others. As you get to know yourself, and you pursue things that play to your strengths, and you begin connecting in ways that open up opportunities for you. Extroverts have to understand that it’s never personal when an introvert isn’t social, and introverts have to understand that extroverts get their energy from a different source. That doesn’t mean you can’t get out of your comfort zone once in awhile, though. Remember, to feel fulfilled you can’t feel comfortable too frequently.

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 https://www.quora.com/profile/Dushka-Zapata or buy her books here https://www.amazon.com/Dushka-Zapata/e/B01F2GZVYQ.

Most leaders suck at showing gratitude and that their relationships matter. Why is gifting a new category of management practice? What are the biggest mistakes brands make when it comes to the gifts they give? Why is gift gifting a relationship accelerator? On this episode, we are joined by giftology guru John Ruhlin who shares why gifting is the secret weapon of relationship building.

Gifting has always mattered, if you go back 5000 years ago, Old Testament kings would give other kings gifts based upon the value of the relationship to deepen the partnership. -John Ruhlin

Takeaways

• Personalize the gift, give it at an unexpected time, and don’t be cheap. Don’t spend money to have a negative impact.

At the start of the show, we talked about the Defy Prison Program and why it’s such a powerful cause, next we talked about cars and hip hop music, and John learned what the LL in LL Cool J stands for. John then talked about why gifting is such a big thing right now, and why most leaders suck at giving gifts. We discussed why gifting should be a cherry on top, not a way to make up for bad business or service. Towards the end we talked about how much you should invest in your relationships and why gifts are emblems of relationship.

We also spoke about:

• Why relationships are the most important asset

There’s a reason why giftology goes back to kings and prominent men in the Old Testament. It is a powerful way to show people that they matter to you. Most people have their gift giving strategy all wrong, they don’t personalize their gifts and they try to do it to get an instant referral. If you give a gift just because, you’ll inspire a referral you won’t even have to ask for. View relationships as assets, approach gifting like a 5 year marathon and be willing to invest in people. When you give someone a gift, it becomes an emblem of your relationship. A great gift is a silent trigger that will make an impact everytime they see it.    

Guest Bio

John is the founder of The Ruhlin Group, a gift strategy and logistics company. They help their clients send world class gifts to Cut Through the Noise, Increase Referrals, and Strengthen Retention with their most important clients, employees, and prospects. Go to http://ruhlingroup.com/ for more information.

The majority of men on public company boards don’t believe that diversity actually makes a difference to the bottom line. What is the fight like for the people who are at the forefront of changing this paradigm? Why should companies want different perspectives around the boardroom table? What is cognitive diversity and relational diversity, and the other various layers of diversity we need in the world? On this episode, Coco Brown, the founder and CEO of Athena Alliance talks about creating parity in the boardroom.  

If you’ve always played the game the way you’ve played it and you don’t think about the new way to play it, you miss out on a lot. -Coco Brown

Takeaways

• For the most part companies recruit for qualifications and not character.

At the start of the show, Coco talked about the origins of Athena Alliance, and why the majority of public company boards don’t have diversity. Next we talked about the danger of getting hung up on what we think men and women can or can’t do. We also spoke about why digital companies are so different, and why we need to have more men speaking about diversity.

We also spoke about:

• The value of varying perspectives and life experiences

Across the board, people in the world are still not equal, and the challenge in the context of business is that women and minorities don’t have the equal opportunity to change the dynamic, and change the way things work. This is a very sensitive time for minorities because they’re tired of not having opportunities, and that’s why diversity is such a necessary conversation right now. Boards are the stewards of the long-term success of the company, and they have to design healthy companies at all levels. Varying perspectives, from varying backgrounds are valuable and important to the health of our business landscape.  

Guest Bio

Coco is the founder and CEO of The Athena Alliance, an organization dedicated to advancing diversity in the boardroom with a robust membership and match delivery model anchored in her deep connection to community building, executive consulting, and professional services. Go to https://athenaalliance.org/ for more information.

We’re in a whole new era of the way companies think about their employees, and the prioritization of wellness and wellbeing is the cornerstone of that conversation. Why is it so important to create a process where individuals can feel successful within the organization that they are part of? How do we slowly kill our bodies when we don’t do any kind of movement? How do we cultivate fulfillment from within? On this episode, we talk to Manny Camara and Keiichiro Yoshida who are making great strides in evangelizing the wellness and wellbeing movement in Silicon Valley.

If I’m going to expect someone to do their exercises and to work on their health, I have to be willing to do that for myself. -Manny Camara

Takeaways

• Movement is at an all-time low because we don’t have to function so much due to automation doing a lot of the work for us.

At the start of the show, we learned how Manny got started, and we talked about the lessons we’ve learned growing up as children of first-generation immigrants. Next, we talked about why wellness is such a big topic right now, and why it’s so important to evangelize it. We also talked about why it’s so necessary for our bodies to move, and why wellness is so important from a preventative and behavioral angle.

We also spoke about:

• The difference between generations in the work force

For companies to keep their people they have to have several elements. They need a healthy culture, a place where employees find their interactions purposeful and meaningful. They need to create a place where their ideas are relished not threatened, and where they can be the performance engine in the organization. Mind, body and spirit work together. If you’re missing one then there’s something missing in terms of your overall output, your overall performance and your overall connection to the organization you’re serving. That’s why it’s so vitally important that wellness and wellbeing is a core feature and function of what we’re doing. When we can tap into what makes us healthy and what makes us feel fulfilled, we can spread that charisma around and make work better .  

Guest Bio

Manny is the founder, of Myo Technology and the Author of Mixed Method Recovery System™. Go to http://www.myotechnology.com/ for more information.

What’s it like to pitch the founders of Google? How does it feel when Sheryl Sandberg informs you that you sound stupid? What does it mean to be radically candid? Here are the three things we learned from Kim Scott on using radical candor to raise performance, lead our teams more effectively, and set high standards.

"Radical candor gets measured not at your mouth, but at the other person’s ear." - Kim Scott

3 Things We Learned:

Radical candor can change the course of your life.

Sheryl Sandberg’s intervention set Kim on a new course, hiring a speech coach and even laying the foundation for what she now travels all over the world speaking, writing and training on - radical candor. If Sheryl hadn’t intervened, Kim probably would never have realized how she was showing up in pitches or public speaking, and her career and business would have been limited as a result. Radical candor means truly doing and saying what’s best for the person, not just keeping the peace.

People in larger organizations exaggerate risk.

People are often more concerned with their reputation than results. When you start to show up with radical candor, 9 out of 10 times the response will be positive. But that 10th time you might get a negative response. People in big companies often overreact out of fear of the downside and forget about the upside of radical candor. Follow the example of companies like Apple and Google. Worry about your reputation less, and focus more on leading people to deliver results.

Good praise challenges us to do better.

Praise is much more than a way to show we care personally. Good praise challenges us to do good work, shows others what success looks like and encourages us to come up to that level. On the flip side, criticism is also unfairly associated with direct challenge, without the element of care. That’s why the Shit Sandwich doesn’t work, it only results in bad praise and bad criticism. Radical candor means helping people raise their performance, setting the bar higher and encouraging them to meet that higher standard.

Radical candor takes emotional discipline. Most people who start to show up with radical candor in their business conversations find themselves backing down when the other person gets upset. But is that what’s best for them, and especially our team, who are accountable to deliver results? Rather than backing down from the challenge, it’s time to step up on the personal caring dimension. Emphasize that your criticism is for a purpose - to challenge them to a higher standard, and support them to meet that standard.

Guest Bio

Kim Scott is the author of the NYT & WSJ bestseller Radical Candor: Be a Kickass Boss without Losing your Humanity. Kim led AdSense, YouTube, and Doubleclick Online Sales and Operations at Google and then joined Apple to develop and teach a leadership seminar. Kim has been a CEO coach at Dropbox, Qualtrics, Twitter, and several other tech companies.

Previously, Kim was the co-founder and CEO of Juice Software, a collaboration start-up, and led business development at Delta Three and Capital Thinking. Earlier in her career, she worked as a senior policy advisor at the FCC, managed a pediatric clinic in Kosovo, started a diamond cutting factory in Moscow, and was an analyst on the Soviet Companies Fund and has written three novels.

You’ve already survived a horrific car accident that literally stopped your heart for 6 minutes. You broke 11 bones. Doctors said you’d never walk again. Not only did you walk again, you ran a 52-mile ultra-marathon. Flash forward, and you’ve just been diagnosed with a very rare, very aggressive form of leukemia. How do you handle that moment of truth?  Here are three things we learned from the irrepressible Hal Elrod, international keynote speaker and #1 best-selling author of The Miracle Morning, on personal development, achievement and overcoming incredible adversity.

When I was diagnosed, I called my wife first. That was a hard call to make. Hal Elrod

3 Things We Learned 

Follow the 5 Minute Rule for Negativity

When Hal was diagnosed, he recalled the advice of a mentor. Allow yourself 5 minutes to be upset, then let go and move on. Hal decided, “I’m going to be the happiest, most grateful person I could be, as I go through cancer, versus feeling sorry for myself or letting fear run my life.”

In Times of Adversity, Get Outside Perspective

When things start to spiral downward, it’s easy to feel out of control and decide that we’ve failed. Depression can even turn our minds off to creative solutions. In those times, it’s critical to gain perspective from people who can see what we can’t. Hal recalled going through the economic crash, where he turned to Jon Berghoff for perspective. Jon brought it with one powerful question, ‘Are you exercising every day? If you’re not putting yourself in peak physical, mental and emotional state through exercise every day, you’re not going to think better thoughts that will move you forward.’ Hal revealed, “The Miracle Morning really started with Jon telling me to go for a run in the morning.”

To Achieve More, BECOME More

We all want “Level 10” success, but are we willing to develop ourselves to reach that level? On Hal’s very first run, he heard the Jim Rohn quote that would change his life, “Your level of success will rarely exceed your level of personal development.” We think the key to achieving more is doing more. But it’s really about becoming more. Hal explained, “When you become more, you have the ability to achieve more with less effort...I realized I have to dedicate time to my level of personal development every day, so I become a Level 10 person.”

The way you start your day sets the tone for the day you create, and ultimately the life you create. If you look at the average person, most people go through their days undisciplined, unfocused and not living the life of their dreams. If you have a focused, growth-oriented and goal-oriented morning, you’re becoming a growth-oriented, goal-oriented