Legends & Losers w/Christopher Lochhead

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147 Duncan Davidson - Why The Future Is Awesome

How do you do business right enough times to be dubbed as a successful serial entrepreneur? How do you turn from entrepreneur to venture capitalist? Today we learn from Duncan Davidson the many prolific ways of becoming the multibillion-dollar rockstar that can turn around even the most reluctant in technological ventures by going a little off the tracks and riding against the current.

“All these things have to have a boom and they have to overcome people’s normal skepticism and resistance.” - Duncan Davidson


Three Things We Learned

  • All great technologies commit in a bubble

Throughout history, technologies trundled in as bubbles that overcame the normal resistance that most new ventures hit and have to climb over in order to gain traction. Change can often chase away people as they are loath to come out of their comfort zones. An effort to entice them into taking a shot at new technologies should have a force overwhelming enough to burst through the many qualms people tend to have upon the introduction of a concept that is alien and therefore seemingly unappealing, a first step towards hitting that initial adoption mark.

  • Humans are pack animals

Humans tend to stick to groups and adopt the thinking shared by the group. As the great philosopher Aristotle once said, humans are social animals. By capitalizing on this knack of people to seek ways in order to belong to a circle and grow that circle, technological ventures can create that necessary boom that will not only truck along innovations but also take them off the ground.

  • Contrarium done right snatches the coveted category crown

Being right in what you invest in is part of the process. But going against the herd of humans is one proven way to create a stir in your technological endeavors. This contrarium, when done right, will produce ripples that can gain you the attention needed to become the next category king.

Technology is the future, and the business of it can be trifling because of the fast turnover of new ideas and concepts that may put off consumers. Causing enough stir to make the cut will entail not only your success but also a future that is awesome and definitely bright for the people. In order to get started, however, one must understand and commit to the many dynamic forces that drive the technological bubble, including going against the herd.


Duncan Davidson is a serial entrepreneur, founder of Covad Communications, and co-founder of SkyPilot Networks and Bullpen Capital. He was very involved in two bubble-era IPOs and spent a few years as manager at VantagePoint Capital Partners. Duncan is now focused on investment in SaaS, blockchain, and internet of things (IOT).

He has an undergraduate degree in physics and math from Brown University and is a magna cum laude in JD from Michigan Law School. His life has taken him from incredible entrepreneur to incredible venture capitalist.

Connect with Duncan on LinkedIn


146: Nancy Pfund - Betting on Elon Musk and Impact Investing

Who are impact venture capitalists and how does this create a new category in the venture capital industry? In this episode, Nancy Pfund, in the parlance of our times, is a legit pioneer of this new category of venture capitalist in Silicon Valley and beyond.


“We invest to drive social, economic and environmental progress in the regions and sectors in which we invest” – Nancy Pfund


3 Things We Learned

  1. Elon Musk a superhero? 
    He is a very hardworking super intelligent, idealistic in his own way
    he is the kind person that can inspire people to drop what they're doing and help save the world.
  2. Impact Investing
    (Nancy Invested in three of his (Elon Musk) companies:
    Tesla, Solar City & Space X)
    "someday ... if your only investing for financial gain people will say to you "well that's not good enough you have to do more than that"
  3. What does the world will look 25 years from now?
    Transportation is electric, autonomous driving, better transportation, less pollutive plants. a cost-effective future.
    on the financial side, people will expect that they are getting more out of their investment dollar than just a financial return, they will see what else they've been able to accomplish from that and this will be the norm, not the exception.


Nancy E. Pfund is Founder and Man­ag­ing Part­ner of DBL Part­ners, a ven­ture cap­i­tal firm whose goal is to com­bine top-​​tier finan­cial returns with mean­ing­ful social, envi­ron­men­tal and eco­nomic returns in the regions and sec­tors in which it invests. Nancy is also the Founder of DBL Investors. As a lead­ing player in the grow­ing field of impact invest­ing, DBLhas helped to reveal the power of ven­ture cap­i­tal to pro­mote social change and envi­ron­men­tal improve­ment, and Ms. Pfund writes and speaks fre­quently of impact investing.

Ms. Pfund is the author, along with Ben­jamin Healey of the widely cited report on the his­tory of U.S. energy sub­si­dies enti­tled, “What Would Jef­fer­son Do? The His­tor­i­cal Role of Fed­eral Sub­si­dies in Shap­ing America’s Energy Future”, co-​​authored with Michael Lazar, “Red, White & Green: The True Col­ors of America’s Clean Tech Jobs”, co-​​authored with Noah Walker, “Ask Saint Onofrio: Find­ing What Has Been Lost in A Tale of Two Energy Sources”, co-​​authored with Anand Chhabra, “Renew­ables Are Dri­ving Up Elec­tric­ity Prices: Wait, What?”, and co-​​authored with Kristofer Holz, “The 2017 Inau­gu­ra­tion: Empow­er­ing a Clean Energy Nation”.

Ms. Pfund received her BA and MA in anthro­pol­ogy from Stan­ford Uni­ver­sity, and her MBAfrom the Yale School of Management.

Fol­low Nancy on Twit­ter @NancyPfundDBL.


145: Joe Sanok - Guru to Practitioners Show

“We’ve got our here and now, we’ve got our own sense of where we need to head, but we also don’t know where we’re headed. Life becomes this adventure that could end this afternoon or it could last to a hundred and five.” - Joe Sanok
How does someone take up the task of teaching practitioners the effective way of practicing what they do? One day we wake up with a consciousness that we’re bound to do significant work, but life offers very few pointers on coming up with the best approach. In this episode, celebrated consultant of consultants, Joe Sanok shares how a deep sense of purpose coupled with the right knowledge to growth in practice will prove indispensable to our life’s cache.
Three Things We Learned
  • Worldliness must be sought in order to grow
Experiencing the world in its plenitude and barrenness is crucial in shaping our life’s work. We seek justice because life is unfair ground, and for this very reason we try to come up with ways to improve the human life we’re born into. By taking stock of where we’re needed by the people who need us, we gain two things: a sense of purpose and an understanding of the different manners by which we can approach and improve our practice.
  • Gratitude must be maintained regardless of our level of success
Pitfalls become of success without gratitude. We miss out on a lot of opportunities in the human experience beyond growing our business, making profits, and just experiencing life in general. Making a habit out of being grateful for our successes, no matter how seemingly trivial or life-altering, will aid us in sustaining steam and blooming in our identified niche.
  • Overcoming the challenge of practicing what you preach is a given
Roadblocks in life often present themselves as ironies. Putting out what we think people need to consume entails that we need to live and breathe them. Becoming the result of our own practice is the best testament to our success.
People often come at life knowing what they want to do but not how they should do it. Opportunities for learning are abundant, but not everyone can readily see them. This can hamper our growth as individuals and create a barrier to making the most out of what our chosen practices can give us.
Having a deep sense of purpose, gratitude, and daring to hone our self-work are crucial to becoming the best practitioners we can be.

Joe Sanok
is a speaker, mental health counselor, business consultant, and podcaster. Joe has the #1 podcast for counselors, The Practice of the Practice Podcast. With interviews with Pat Flynn, John Lee Dumas, Chris Ducker, Rob Bell, Glennon Doyle Melton, and Lewis Howes, Joe is a rising star in the speaking world! Joe is a writer for PsychCentral, has been featured on the Huffington Post, Forbes, GOOD Magazine, Reader's Digest, Bustle, and Yahoo News. He is a keynote speaker, author of five books, and is a top-consultant.


144: Karin Hibma: A Pioneer in Design Thinking

A lot of people use the word brand incorrectly without really thinking about what it means. What is strategic identity and how does it allow us to ask the right questions about brands? How do you define a problem and go about solving it? How do we embrace the chaos in our lives? On this episode, the grand dame of design thinking, branding and naming, Karin Hibma talks about creativity, career, and innovation.

I want deep relationships and transformative things that are going to change the world. - Karin Hibma


3 Things We Learned


- There’s a difference between strategic identity and branding

The word “brand” is a label that gets attached to many things, even when it hasn’t been thought out. Too many people invest in brand energy without really knowing who they are and who they want to be.

- Uncertainty breeds creativity

A time of uncertainty is a creative time. If you can accept it and embrace it rather than fight it, so much more value of fruitfulness and happiness will come out of that. If you are able to embrace chaos in that uncertainty there will be more opportunities than when you resist it.

- We’re in a very special time in innovation and design thinking

We are at a nexus point of a lot of technology and innovation like AI and VR. This means when we look back to the era we’re in right now, this age is going to be unrecognizable. We’re not even close to using all the innovation capacity that’s out there. Exciting times are ahead.


For individuals and companies, a lot of the greatest opportunities, moments, innovations and creations come out of the greatest times of uncertainty. Sometimes we make the mistake of trying to ignore and fight through the unknown by looking for a quick solution. If you are able to embrace chaos and be comfortable in that uncertainty, the universe will give you surprising answers.  


Guest Bio

Featured in the Harvard Business Review and honored with Fast Company's “100 Most Creative People in Business” award, Karin Hibma is a design, naming and identity legend. She works to see the world through the eyes of customers, using cognitive identity insights and design thinking to find the strategic “big idea” inherent in every project. An early entrepreneur, Hibma founded creative research company Design Resource. She founded Cronan Artefact – their award-winning Walking Man apparel line was sold in one of the earliest online catalogues. Co-founder and principal of : : CRONAN : :, a strategic identity design consultancy working with change-makers looking for innovative answers, from startups to Amazon Kindle, Apple, Estée Lauder / Origins, Levi Strauss & Co., SFMOMA, TiVo and the White House.


143 Dave Frey - Ramones CoManager & Music Promoter

How to design your life around your passion? Dave Frey is among the luckiest men alive. He took his love for music to greater heights from playing in bands to promoting shows to managing the punk rock category king and now to being the CoOwner of the Lockn' Festival.

"If you learn from losing, then you can win." - Dave Frey

3 Things We Learned:

Music hits are typically born during the first three to five records
Songwriters improve when they don't know what they are doing. Their innocence express pure and genuine emotions and/or ideas. On the other hand, familiarity with the trade allows for lackluster pieces.

People can start in the music industry at such a young age and achieve unparalleled success.

A lot of musicians start early in life. Passion and perseverance empower them to accomplish more than the others. Joey Ramone, for example, became an active performer during his teenage years.

Creativity is possible despite the insane dysfunction
One thing peculiar about The Ramones is they communicate through third parties. They never spoke with one another. Nevertheless, it did not prevent them from being creative, from amassing a solid fanbase, and from giving life to the punk rock category.

Frey has an insatiable passion for music. Since childhood, he wanted to perform in a band. He'd practice many hours with his guitar and worked hard on the promotions.

True enough, he landed a career with promising musicians and individuals in the industry. He believes that people have a lot to prove for themselves. Mediocrity has no room in the field of passion.


Dave Frey started off small, promoting his first show out of sheer necessity after his band's equipment was stolen. “So this club owner did a benefit for us, and I went to the local radio station, gave away tickets and got the guy at the paper to write it up,” he says. “The show did really well, and the guy who booked the club decided to quit. So the owner said, ‘Hey, you did a good job. Can you book the club for a couple weeks until I find a new guy?’”

By 1985, Frey had relocated from his native Chicago to the Big Apple, where he took a job as a booking agent, working alongside two of the city’s leading promoters, Ron Delsener, who the New York Times once referred to as “Rock's Mr. In Between.”

In 1992, Frey founded Silent Partner Management, a company that’s represented acts like the Ramones, a leather-clad quartet from Queens heralded as one of the pioneers of punk rock, Cheap Trick, and Blues Traveler. He teamed up with Blues Traveler for the H.O.R.D.E. (Horizons of Rock Developing Everywhere) Festival.

It became a kind of rival to the more alternative swing of Lollapalooza, enjoying a seven-year run while attracting an eclectic array of performers ranging from Beck to Neil Young.

Then, in 2008, Frey migrated to Charlottesville, where he and partner Peter Shapiro would soon begin planning what’s likely become the largest musical gathering to hit Central Virginia, Lockn'.



142: HBR’S Dan McGinn Gets Psyched Up


There are moments in our lives that can either make us or break us. When you are engulfed with the reality of a performance, what are the things you should do before even setting your foot on the stage? Harvard Business Review's Senior Editor Daniel McGinn shares self-liberating examples from his book Psyched Up. 

"If you haven't come up with a routine that lets you handle the flood of adrenaline you're going feel the moments before you walk on stage, it's going to detract from your performance." - Daniel McGinn

3 Things We Learned:

  • Be prepared to deal with your make or break moments
According to McGinn, there's a disproportionate thin slice of moments. Everyone can work as many hours in a year towards a goal but only a proportion of which can either make you or break you. How you set yourself up towards those moments matter. 

  • Market leaders usually don't look behind themselves too much
Jeff Bezos and Amazon, for example, focus on the needs of their customers. Looking after competitors isn't that big of a priority. They create the rules and always refer back to their founding principles.

  • Practice is never enough; exposure to reality is also necessary
Train yourself to deal with the adrenaline, whatever industry or trade you belong. Be mentally prepared in order to perform at your very best. Otherwise, the anxiety will take away from your skills and hours invested.    

McGinn has always been fascinated with the moments in life. It started during his high school years. He saw how routines -- pep talks, trash talks, rituals, etc. -- equipped individuals in different circumstances and situations. How do you dominate a niche? How do you stay in the lead? What does science say about getting prepared to win? Perhaps, all you need is to get PSYCHED UP.


Daniel McGinn spent 17 years as a reporter, bureau chief, national correspondent, and senior editor at Newsweek, based on New York, Detroit, and Boston. 

In 2010, he joined Harvard Business Review where he now spends most of his time editing the IdeaWatch and How I Did It sections. He also manages the magazine's annual Best Performing CEOs in the World ranking and edits feature articles on topics including negotiation, sales, and entrepreneurship.

His freelance writing has appeared in magazines including Wired, Inc., Fast Company, and The Boston Globe Magazine. McGinn has also appeared as a guest on NBC’s Today Show, the CBS Morning Show, PBS’s NewsHour, CNN, CNBC, MSNBC, and NPR.

His books include PSYCHED UPHouse Lust: America’s Obsession with our Homes, and How I Did It: Lessons from the Front Lines of Business (as editor).


141: Mark Allen: The Greatest Triathlete of All Time

Human beings struggle to gain insight and push through pain because we don’t give ourselves time to quiet our minds. Why is mental training and conditioning so integral to the success and resilience of athletes? How do you incorporate tools or practices to help people strengthen their minds? On this episode, Mark Allen talks about what it took to become a globally-respected, legendary athlete.

You can be conservative and not fall apart, but that’s not racing. -Mark Allen


3 Things We Learned

Athletes want to be peaceful, but powerful

“Peaceful but powerful” is the goal for an athlete. It’s all about finding a place where you’re completely at peace but can access your strength and steadiness.  

Sometimes you have to be completely different

So many times in our lives we accept the rules in a way that isn’t “frontal lobe”, and we don’t question them. However, sometimes when your competition is going in one direction, you may want to go another.

Give yourself time for a quiet mind

When you're fully engaged in something and your mind is quiet, answers can come that you would have never been able to think of on your own. When you’re daydreaming, the creative problem-solving part of your brain is at its peak. It’s important that we give our minds this opportunity to be open to recovery and new insight.


Peak performance is the same across all disciplines. It’s all about being able to sharpen the mind so you can deal with fear and doubt, and how you’ll react when things seem impossible. It takes a willingness to give everything, despite the risk of failure. Connect to a place of potential and possibility, instead of helplessness and impossibility. You have to condition your mind to a point where-- no matter what-- you’re going to take that next step. It doesn’t have to be perfect to keep going. If you can bring your mind to a place of peaceful power, all the fear and doubt with be shut out and your brain can drive you forward with full force.  


140: Mike Maples, Sr. - Microsoft Legend

What was it like during the early days of Microsoft? Its former President Mike Maples, Sr. unravels their journey. How did they rise to becoming a tech giant with a $745 billion market value? There was no stopping towards success. 

"There is a price to be paid for every technology." - Mike Maples, Sr.
3 things We Learned

  • Ultimate benefit outweighs the risks
Security holes can be found in every step of the development process. But they do not necessarily take away the real value of the outcome. The ultimate goal provides more value than the difficulties of overcoming those holes and dangers.  
  • Love for technology can never be justified
Why do people have far more than they need? As with other things, people can step into technology as a hobby. They create or buy not because they need to but because they love to. 
  • There is a downshift in entrepreneurship 
Companies and individuals want to invest in new ideas. But, according to Mike, the sourcing of money to create have become an inhibitor in many ways. How people source money and use it matter.

In a company or organization, there can be self-destructive values and shared values. But these values can still be changed. Core values are essential to a company during its first days. A healthy balance of recognition and reward and of punishment and penalty are also needed.

Mr. Michael J. Maples, Sr. serves as an Ambassador on certain strategic relationships and internal management initiatives at Microsoft. Mr. Maples served as an Executive Vice President of Worldwide Products Group at Microsoft Corporation. He served as a Consultant and Advisor to Microsoft. He served as the President of the Microsoft Corporation. He served several positions with Microsoft from April 1988 to July 1995, where he served as an Executive Vice President of Worldwide Products and a Member of the office of the President. He is a highly accomplished Senior Executive with over 40 years experience in the computer industry. He retired from Microsoft Corporation where he reported directly to Bill Gates. He was responsible for all product development and product marketing activities at Microsoft during his tenure. Mr. Maples holds an M.B.A. from Oklahoma City University and B.S. degree in Electrical Engineering from the University of Oklahoma.

139: Jen Groover - One Woman Brand


"The more people are becoming authentic, bolder, raw, and real, the more they want more of it because it is more identifiable than when everything's perfect." - Jen Groover


How do you become your own brand in the new media? Modern society has its own say for being different and bold. In this episode, Jen Groover shares what it takes to be authentic and to produce massive success in the end.   


Three Things We Learned



  • Authenticity has various definitions



Because of our training, there are belief systems that we abide. But it does not always work. We can be authentic just the way we are in the new media. Unique ideas can shine brightly despite the oppositions, as in the case of Spanx Founder Sara Blakely.



  • Existing ideas have untapped potentials



Creativity opens the door to greater possibilities. It knows no bounds. Existing ideas can be reimagined and transformed into outstanding ones.



  • Influencer marketing is leading the way



Industry influencers have established a name for themselves in the categories they belong. Nowadays, partnering with them to market a brand has become widely popular. They have the power to reach the information you desire.


With the rise of social media and other marketing platforms, people can already choose any information they want. They also get to choose which type of authenticity they want to see or hear from.


Despite how rude the language is, people still enjoy the message they receive. As Jen puts it, people can identify with it better when not everything is perfect.



Empowerment and Business Expert, Creator of The Butler Bag, Author of “What If? & Why Not?”, Motivational Speaker, Entrepreneur, Spokesperson & Media Contributor

Jen Groover has been tagged by SUCCESS Magazine as a “One-Woman Brand”, a “Creativity and Innovation Guru”, and a leading “Serial Entrepreneur” by Entrepreneur Magazine. Jen Groover’s name has quickly become synonymous with innovation, entrepreneurship and evolution. She has gone from guest-hosting television spots, to inking deals with some of the industry’s biggest heavyweights. Jen recently made history at the New York Stock Exchange, as a member of the first all-female group to ring the opening bell, representing women’s leadership and economic independence. Her influence and leadership has aligned her with amazing brands, such as USANA Health Sciences, Avon, Verizon and SkyMall, for which she acts as a spokeswoman.


Her success skyrocketed with the creation of the Butler Bag, the world’s first compartmentalized handbag, and has not stopped since. Jen spring-boarded the Butler Bag’s success into an entire lifestyle brand, found at a variety of price points and well-known retailers, which led to the creation of subsequent lifestyle brands, Leader Girlz, and Empowered by Jen Groover. Leader Girlz teaches young girls the importance of empowerment through play, while the recently launched “Empowered by Jen Groover” brand, including her one hour PBS special and forthcoming book, comprises a variety of consumer products that encompass her quotes and inspire people to live life with passion and purpose. The success and momentum of Jen Groover’s empowerment movement has led to the development of Jen’s upcoming, highly integrated tech platform, “Empowered for Purpose,” which will serve as a foundation for further expansion of the “Empowered by Jen Groover” brand.


Jen is a top business and lifestyle contributor and content creator for major television networks such as ABC, CBS, CNBC, NBC, Fox News, Fox Business News and The CW. Jen also contributes editorial pieces to several prominent business magazines and online resources including The Huffington Post, Entrepreneur Magazine, Positively Positive, The Daily Love, and HealthyStyle NY. Her products, brand and work have been featured in hundreds of media outlets including O! The Oprah Magazine, Redbook, People, US Weekly, SUCCESS and Entrepreneur, to name a few.


Jen’s passion for inspiring others to realize their greatest potential on all levels is the driving force behind her many successful brands. Jen’s diverse experiences and businesses span many different industries and she has no desire to slow down anytime soon. She constantly motivates and inspires through her keynote speaking engagements for corporations, universities and organizations all over the world. Jen continues to strive toward her ultimate goal, which is to innovate in every industry she is inspired to play in while empowering others to achieve their goals. Jen is more than a more than a multifaceted, multitalented individual – she is, undoubtedly, a force to be reckoned with. Jen believes in active participation and lives by the belief that “if you are going to complain about something you better be willing to do something to inspire change.”


For more information about Jen Groover, please visit www.jengroover.com

Follow Jen Groover on Twitter @jengroover

Like Jen Groover on Facebook at www.facebook.com/jengroover


138: Jess Lee: Sequoia VC Changing the Startup Game

2017 was a year of upheaval for the tech industry, and now change presents big opportunities in the diversity conversation. Does the idea of meritocracy really function in a world where inherent biases might exist? How do you identify potential in someone with no proven track record of performance? Why does “distance traveled” matter? On this episode, I dialogue with Sequoia Capital partner, Jess Lee about making diversity a priority in tech.

In a high intellectual capacity job where there’s collaboration, diversity actually produces performance and better outcomes. -Jess Lee


3 Things We Learned

VCs must prioritize what their clients prioritize

As VCs, your customers are your founders. At the end of the day, you have to be able to convince the best founders to work with you and make a difference in their trajectory. You must care about what’s important to them.


Distance traveled is a worthy metric of success

We tend to judge a person based on where they are but it’s important to know where they started. The distance they traveled to get where they are is what we should be evaluating.


Meritocracy is the ideal, but people don’t always start on an even playing field

There are inherent biases that affect how someone is considered and evaluated in their field, and these can easily taint meritocracy. It’s important to remember that the bar isn’t the same for everyone.


When it comes to diversity in the workplace, meritocracy is the ideal. However, it’s also necessary to measure the distance traveled by a person. It’s more about where they started and how far their journey has taken them, and less about having a huge headstart to get to the same point. There is something to be said for being willing and able to hire on potential. Making this a priority won’t just make us more diverse-- it will improve the outcomes for companies.


Guest Bio

Jess Lee is a partner at Sequoia Capital and the former chief executive officer of Polyvore. Follow her on Twitter @jesskah.