Christopher Lochhead’s Legends & Losers

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188: Ann Miura Ko Most Powerful Women in Startups

Why is voice an important part of one's future? How do we develop a sense of both individuality and community? In today's episode, Ann Miura Ko joins Christopher Lochhead to have a free-ranging conversation from being a mom, growing up an immigrant, and her eventual success that started with being a loser.

“I don't know which end I value more, but ultimately I love the creativity of a society like ours more than having people look over my shoulder all the time.” - Ann Miura Ko

Three Things We Learned

  • Most public goods are things we don't enjoy

This is mostly thanks to how humans treat public property. There's a view that when autonomous vehicles become a hit, people wouldn't have any real need to own private cars anymore. This leads to the question of whether we as humans would be able to stick to the moral duty of maintaining public goods without an actual, breathing person in the loop.

  • Japan is the prime example of living as a community

Ann is the daughter of two Japanese immigrants. Growing up, she would come to Japan and every single time, she ended up struck by the strong sense of community of the Japanese. People take care of public property and keep things clean and orderly for everyone's benefit and make sure everyone hold the same standards of living.

  • Community or individuality

Having someone watch your every move and breathe down your neck can be very oppressive in a sense, but so is the strong pursuit for freedom and freedom only. A strong sense of community can prevent people from doing something detrimental to the larger populace. But people also achieve happiness by embracing their individuality.

Striking the balance of a sense of both community and individuality can be a quite the challenge. We have our social obligations to fulfill and we also have the personal mission to seek self-improvement in order to become successful at what we do. In fulfilling both our social and personal duties, however, we must remember that we can only truly develop character when no one is watching.


Ann Miura-Ko has been called "the most powerful woman in startups" by Forbes and is a lecturer in entrepreneurship at Stanford.  

She’s the child of a rocket scientist at NASA, Ann is a Palo Alto native and has been steeped in technology startups from when she was a teenager. Prior to co-founding FLOODGATE, she worked at Charles River Ventures and McKinsey and Company.

Some of Ann's investments include Lyft, Ayasdi, Xamarin, Refinery29, Chloe and Isabel, Maker Media, Wanelo, TaskRabbit, and Modcloth.

Ann is known for her debate skills  

She lives with her husband and 3 kids ages 8, 5 and 3.

Education: BS, Yale University (EE); PhD Stanford University (Math Modeling of Computer Security.)



187: How to Listen to a New Podcast

In today's short episode, Christopher Lochhead touches base with his listeners to discuss a rather crazy topic he's been asked about. How should you listen to a new podcast?

"By design, the typical interview is deeply inauthentic." - Christopher Lochhead

Radio Pitfalls

Radio has taught us to listen to a very particular format. This is the standard interview we're all very familiar of, which is exactly the type of show that Christopher is averse to.

With the host and producers seeking to get a narrative across to the listeners, they actively deliver what they think are the best parts of a show. Christopher thinks that this is not representative of a true conversation amongst people.

Listen with Fresh Ears

The interview and radio paradigm has made us comfortable with a particular listening experience. When you're a first-time listener to a great podcast, it's going to sound unique and fresh. This difference in experience can sometimes be off-putting and jarring by virtue of what we're used to as listeners.

If you find yourself thumbing around a new podcast, you're there for a reason. Someone might have recommended it to you, or you thought the host was a cool person. Whatever it is, you must listen to it with fresh ears.

Stick It Out

Sticking to a new podcast requires effort. But you can only judge a show by listening to a couple of episodes. You need to test the waters before you opt out or take the plunge.

Christopher isn't new to this trial and error. He got recommended a new podcast hosted by Jordan Harbinger. He didn't like it at first, but it grew on him soon enough.

"There was one percent of my brain that was going, 'There's something here for me.' And because I gave it a chance... it's one of my favorites." - Christopher Lochhead



186: Chris Ducker Youpreneur Category King

Chris Ducker is a Youpreneur superstar and author who sits with Christopher Lochhead today to have a fun conversation about all things virtual and niching down. How do you hire excellent virtual staff? And what books are great for entrepreneurs?

"At the risk of being controversial... The Art of the Deal by Donald Trump is probably one of the best books I've read." - Chris Ducker

Three Things We Learned

  • Dog-eared books over unused books

Chris has always been the dog-eared page kind of guy, someone who abuses highlighters as he consumes books. From a writer's standpoint, he thinks seeing his authored books go through the same fate as his own collections is something that writers can feel validation for. To see your books get used and be passed down from one person to another is pure bliss.

  • Everyone wants and should write a book

When Virtual Freedom came out, Chris only wanted to get everything off his chest. Consumed by the idea of developing a system for bringing onboard virtual staff to help entrepreneurs build and grow their businesses, Chris wrote the book. It flew off the shelves and became the bestseller that it is now today.

  • Some authors are afraid to follow up and fail

There are brilliant authors who stop writing books once they have produced a bestseller. This hesitation all comes down to the fear of not succeeding as much as the first time, and while it's a very valid fear, it's not something that's going to help anyone grow. After writing a book that rose up the list fast, Chris faced the same fear and produced another book that made him proud.

Writing a book is daunting. When people pass up the opportunity, however, they also miss out on the chance to realize that writing one could have been something that they would have never thought of not doing. Clearly, everyone and anyone can write a book and can act on the call to get down and do it.


Chris Ducker is a serial entrepreneur and author of the bestseller, "Virtual Freedom", and more recently, "Rise of the Youpreneur".

Based in Cambridge, England, he owns and operates several businesses, that combined house over 400 full-time employees internationally.

He's also a trusted international business mentor, keynote speaker, podcaster, blogger, as well as the founder of - the leading personal brand business education company in the world.

Chris hosts the annual Youpreneur Summit, which is held in London, U.K. each November and is the self-proclaimed 'Proudest Brit' doing business online!



185: Jeff Richards China, Silicon Valley & Billion Dollar Startups

How do you develop young leaders and entrepreneurs in this fast-paced world? What is the power of investing and building multi-million dollar companies? Jeff Richards sits down with Christopher Lochhead to answer these questions and discuss why it's smart to invest in China and Silicon Valley.

"There's 7.3 billion people in the world. There's only 300 million in the US. So if your market opportunity is 300 million, you're missing the other 95% of the world." - Jeff Richards

Three Things We Learned

  • It's tough for kids these days
Because kids have access to social media at an early age, they have a broader preview of the world out there compared to generations past. While it's very encouraging for them to find ways to become successful apart from the traditional get-educated-land-a-job scheme, being exposed to these things as a teenager can be a pitfall. They're hit with the pressure to be creative, innovative, and get together with the right crowd early, existential crises adults back then would often encounter not until after college.
  • Pace of play nowadays is fast
Technological advancements have made it quicker to build businesses and make them successful. However, with this quick pacing comes the added pressure that trickles down to entrepreneurs who are throwing so much into the fire in very little time in order to keep up. They have no time to catch a break, and risk many other aspects of their lives because of the swift turnover of things in the tech industry.
  • We need to go back to building brick by brick
The satisfaction of building a product with a great foundation springing from doing it right can't be undermined. People need to learn how to build businesses brick by brick, painstaking piece by painstaking piece. We need to slow down and revel the process of becoming successful.

So much is going on in the tech world right now that people are compelled to constantly pit themselves into the fray. We must pause and zoom out of the small corner of the world that we're building in order to gain true insights of the world at large. If we're not trying to glean and learn as much as we can, then all our efforts and money will easily go up in smoke.

Bio / Story: 
Jeff Richards 
A Managing Partner at GGV Capital, Jeff joined the firm in 2008 after spending 13 years as an entrepreneur and operating executive in the US and Asia. Prior to joining GGV, Jeff founded two venture-backed companies, one a success and one a “huge failure” in his own words – “I learned a lot.”  
His background as an entrepreneur gives him a unique perspective on the challenges of starting and running a venture-backed company, and he works closely with the GGV Talent team on Founders+Leaders. 
Jeff focuses on the Software and Internet sectors, and currently sits on the boards of or is a board observer at BigCommerce, one of the top ecommerce software platforms, Boxed, a rising star in the ecommerce space, Brightwheel, the leading SaaS provider for the early education vertical, Gladly, a next generation SaaS platform for customer care, Percolate, a leading marketing SaaS platform for global brands,PlushCare, a mobile platform for consumer healthcare, Reebonz, Southeast Asia’s leader in luxury ecommerce, Slice, a market network for the pizza industry, and Tile, the platform for location. Jeff also led GGV’s investments in Appirio (acquired in 2016 by Wipro), BlueKai (acquired in 2014 by Oracle), Buddy Media (acquired in 2012 by Salesforce), Citrus Lane (acquired in 2014 by, Evolv (acquired in 2014 by Cornerstone OnDemand), Flipboard, HotelTonight, ShiftGig, Voicera and Zylo, and has been actively involved in GGV’s investments in Domo, OpenDoor, Square and Wish. 
Jeff is a frequent guest on CNBC and often writes on topics like startup management and leadership, venture-backed IPOs and shifts in tech trends across the US and China. 
Before GGV 
Prior to joining GGV, Jeff founded two software companies: R4, a supply chain SaaS business acquired by VeriSign (NASDAQ: VRSN), and QuantumShift, a telecom software business backed by Texas Pacific Group (TPG).  
Earlier in his career, Jeff worked in Asia and Latin America with PriceWaterhouseCoopers. Jeff graduated from Dartmouth College, where he was a four-year letterman on the basketball team and is on the Advisory Board for the Dartmouth Entrepreneur Network (DEN). 

184: Should You Care if People Think You’re Weird

In this short episode of Legends and Losers, Christopher Lochhead ponders a question that he has previously answered. Do you care if people think or say that you are weird?

"We're trying to find the magic line between deeply connecting with people but not overly concerning ourselves with what they think of us. It's a bit of a dichotomy." - Christopher Lochhead

The World as We Know It

We live in a world that tricks us into believing that the pathway to professional or personal success is fitting in. That we need to color inside the lines and be like everyone else in order to succeed. Some of us are told to sit still and be quiet and not make too many waves.

There have been countless times in Chris' life when he has fallen into the trap of trying to manage what other people think of him. But human autonomy dictates that there's really no way to control what people are going to think of us.

Perils of Fitting In

Based on Chris' own experience, becoming part of the crowd isn't the path to success. Having the courage to stand out will pave the way. When we try to manage what other people think about us so that we're not written off as weird or different, we are actually trying to fit in.

And the biggest irony of this deep, inherent human desire to fit in? People who are different make the biggest difference.

Break Ground by Embracing Your Weird

People who managed to become successful in their chosen careers broke new ground by being different. If any, very few of them fit into the mold that society has made for us.

We want to maintain human connections, sure. But getting lost by following others guarantee failure to learn who we truly are and what we can be. Only by embracing our different and weird can we become the legendary versions of ourselves.


183: Jay Larson Sales Rep to CEO

What exactly is the power of hard work? Why does it always pay to be all about goodness? Jay Larson joins Christopher Lochhead today to share the legendary story of how he went from Sales Representative to CEO slowly but surely.

"It was always better to be the number two guy in an A opportunity than the number one guy in a C opportunity." - Jay Larson

Three Things We Learned

  • It's important to have the right move at the right time

When Chris first asked Jay some scotches ago if he saw himself becoming a CEO anytime in the future, Jay had been convinced that he wouldn't. But now that he's on his second time being one, he finds himself looking back and remembering how he had a great run at sales before eventually becoming the leader that he's meant to be. He wasn't the guy that felt the urgency of becoming one, but with how things have unfolded, he's very fortunate to have made the career move at the most opportune time.

  • Conscious decisions for a successful career

Jay took his time priming himself despite the truth that the software business works at a rapid pace. He's always been confronted with choices of doing deals that didn't strike him as terrific even as a CEO or running a sales or field operations for a terrific company as an employee. But his conscious effort to grab any learning opportunity and being patient with his growth has paid off.

  • You need to go high before you can go wide

Before he can become a full-fledged CEO, he had to develop the skills and learn the functions needed to run an organization. His many experiences in the field made Jay a lot more willing to test out his mettle and take the next logical step in his career. He took on the role of a leader when he was finally convinced that he was great and capable enough at what he did even when he had to do it at almost fifty.

The tech business is a constantly changing world with everyone seemingly caught in a race to reach the top of the ladder. Many tech geniuses start out young, but there are those like Jay who take their time learning the ins and outs of the biz before finally taking the plunge. And for some, it's the perfect way to go.

Bio / Links:

Jay Larson started in sales in Oracle and Siebel. He became Head of WW Field ops at Mercury Interactive, Head of Sales at SuccessFactors, President of Jive, CEO of Birst. And now, the CEO of red-hot Optimizely.


182: Ray Wang #1 Tech Analyst

Today, Ray Wang joins Christopher Lochhead to talk about diversity, startups, and why Alexa is kind of terrifying. They ask questions of how much privacy humans are willing to sacrifice for convenience. They also discuss the digital rights of humans.

"At some point, the right to be disconnected is also going to be a huge right." - Ray Wang


Three Things We Learned

  • Inclusion is a long-standing and complicated systemic struggle

From educational institutions to the corporate sphere, diversity has been a decades-long problem that can't be easily resolved by lobbying for inclusion to meet quotas and improve statistics. To be inclusive doesn't mean to merely increase the percentage of people of color in schools or female CEOs in networks. What needs to be done is to continue upholding meritocracy and fairness in order to affect actual changes that will allow for realized diversity.

  • We should probably get paid for our data

For the longest time, people have been selling their personal data in order to avail of services without realizing. Everyone bills for the products from these services, but it's time to treat data privacy as an asset and part of the process of moving society forward. If data privacy were made a property right, it would offer more protection to the digital footprint people leave behind.

  • Too many exception-based rules have been passed

When people's privacy rights are taken away either in whole or one by one, they're trampled on and people enjoy less freedom. In turn, the demand for new rules to be passed in order to protect this freedom shoots up. This cycle is actually more counterproductive than effective because society has reached a point where exceptions are made the rules when in fact, policies must have a larger, broader scope in order to truly protect everyone and everything.

With the digital world constantly expanding, our exposure to the digital sphere we navigate increases. There are several drawbacks to increased digital engagement, and most glaring is the potential to ultimately lose our data privacy rights and freedom. Humans need to work harder in order to keep this from happening and more rigid policies must be passed in order to strengthen our protection.


R "Ray" Wang (pronounced WAHNG) is the Principal Analyst, Founder, and Chairman of Silicon Valley based Constellation Research, Inc.  

He's also the author of the popular business strategy and technology  blog "A Software Insider’s Point of View". With viewership in the 10's of millions of page views a year, his blog provides insight into how disruptive technologies and new business models such as digital transformation impact brands, enterprises, and organizations.  

Wang has held executive roles in product, marketing, strategy, and consulting at companies such as Forrester Research, Oracle, PeopleSoft, Deloitte, Ernst & Young, and Johns Hopkins Hospital.

His new best selling book Disrupting Digital Business, published by Harvard Business Review Press and now globally available provides insights on why 52% of the Fortune 500 have been merged, acquired, gone bankrupt, or fallen off the list since 2000.  

In fact, this impact of digital disruption is real.  However, it’s not the technologies that drive this change. It’s a shift in how new business models are created.

Wang has held executive roles in product, marketing, strategy, and consulting at companies such as Forrester Research, Oracle, PeopleSoft, Deloitte, Ernst & Young, Personify, and Johns Hopkins Hospital.  

He is a prominent and dynamic keynote speaker and research analyst working with clients on digital, innovation, business model design, engagement strategies, customer experience, matrix commerce, and big data.

His Silicon Valley research firm, Constellation Research, Inc., advises Global 2000 companies on the future, business strategy, and disruptive technology adoption.  

Ray is a regular contributor to Harvard Business Review and well quoted in The Wall Street Journal, Forbes, Bloomberg, CNBC TV, Reuters, IDG News Service, and other global media outlets.  Wang has thrice won the prestigious Institute of Industry Analyst Relations (IIAR) Analyst of the Year Award.



181: Digital Body of Work

In this special episode, Christopher Lochhead contemplates his conversation with Isaac Morehouse on Episode 170. Isaac is the founder of the company called Praxis, which pioneers a new category called career launch. In this particular episode, Christopher talks about a couple of terms he encountered during that particular dialogue that made him think about one's online credentials and digital body of work.

"It is increasingly getting more important to understand what happens when people Google you." - Christopher Lochhead

Three Things We Learned

  • We turn to Google to learn more about people
It can be an acquaintance you meet through a social network of some sort or someone you corresponded with over e-mail. If we think about it, when we meet someone today, that first thing that most people do to find out who these new people are is to run to Google. One simple, 15-minute search will provide you with the necessary information needed to get to know someone you just met.
  • What happens next when we get Googled is critical
Whether you're a professional, an artist, an executive, or just a regular person is neither here nor there. People will look you up online to find out more about you. And what they pull up when they do a Google search on you will highly dictate not only their impression but also their perception of you as an individual in this highly digital world.
  • We need to be more proactive about our digital presence
In order to thrive in various online industries, we need to start putting in more work to build our digital presence. We need to start thinking about our digital body of work. We need to build our own websites, LinkedIn profile, and post blogs and content to gain traction and increase engagement and ultimately, chances of breaking through our own niches.

What is your digital body of work? What social proof do you have? By building our digital presence, we're also shaping ourselves into becoming our own credentials, and that is most important.


180: Niche Down Thank You

Christopher Lochhead shares good news and expresses his gratitude for the successful launch of Niche Down. He shares how dreams do come true and how moving forward in the face of no results can turn out great.

"No matter how much we think we make us successful, the truth is, it's other people who make us successful." - Christopher Lochhead

Christopher Lochhead - A Successful Launch

Niche Down was number on both of its categories on the day  it was launched. It is very clear that the main reason for this is that the listeners of the Legends and Losers podcast headed over to Amazon, bought, and downloaded the book on that fateful day. With this knowledge, Christopher wishes to thank everyone from the bottom of his heart for making this happen and for making this possible.

The Story Behind

There was once a 19-year-old entrepreneur with no education, no contacts, and no money. But he had a partner, a dream, and a book by Michael Gerber, The E-Myth. When Christopher was 19 years old, he read the book and the book changed his life.

In the book, the author lays out why small businesses fail and while franchises break through the market. It comes with guidelines on how to build a process-oriented business that can run and not be run to the ground without you. The book, along its legendary brethren, has made a huge difference in Christopher's life and helped it turn out the way it did.

Dreams Do Come True

If someone had come up to him and told the 19-year-old Christopher that he would be authoring Niche Down three decades later and said book would top and beat The E-Mythfor a time, he never would have believed it.

Overall, the experience is absolutely mind-blowing, one that he will never forget. And Christopher is eternally grateful.

"And all that has happened because of you, the Legends and Losers listener." - Christopher Lochhead

To hear more of what Chris has to share with you, download and listen to the episode now!

Find out more:

#1 Amazon Best Selling Book

Niche Down


179: John McDonald - Semi-Handmade

John McDonald was once a struggling screenwriter and actor who niched down and became known for Semihandmade. He opened himself up to a career and entrepreneurial opportunity, seizing it and making a name for it. In today's episode, John talks openness to opportunities and vulnerability with Christopher Lochhead.

"If you're willing to be vulnerable, anything is possible." - John McDonald

Three Things We Learned

  • There's no rush to figure things out

They say that life begins at 40. When he was 40, John was struggling to penetrate the woodwork industry. The road that led to the decision to give woodwork a shot was long, involving forays into screenwriting and waiting tables as the angriest waiter in Hollywood.

  • Opening yourself to vulnerability will open doors

John came to Los Angeles with a vague notion of wanting to be part of the film industry. He ended up assisting in production and writing scripts to the side, but even then he didn't feel happy. Several rejections and failures later, he was finally able to become the rockstar, go-to guy for designing custom doors.

  • Success is found everywhere

When he first ventured into Hollywood, John knew he wanted to be rich and famous. Writing didn't hand him these successes, but woodwork was the stepping stone. By not limiting himself to something he wasn't fully committed to and didn't give him the satisfaction he needed, John was able to become legendary.

Some of us spend our whole lives trying to find success in what we think we like to do and in things we think we're good at. But success is ultimately self-determined and can be found anywhere if we only try to look more closely and elsewhere. John is a testament to that, and we can all be legendary if we want to be.

Bio / Story:
In 2002, at the age of 34, John McDonald traded screenwriting for custom cabinetry. He launched Semihandmade in 2011 using IKEA cabinets as a base for handmade craftsmanship at a competitive price.  
 The concept is simple: when purchasing kitchens and other cabinets, IKEA gives customers the flexibility of not buying doors. That’s the after-market space Semihandmade fills. Offerings include doors for both the new Sektion and recently-discontinued Akurum kitchens, as well as several IKEA bathroom, closet and media systems. 
 In five years, Los Angeles-based Semihandmade has grown to over 40 employees and 17000 SF of manufacturing space. Showrooms include Palm Springs and Burbank, CA. Doors ship throughout the Continental US and Canada, with clients that range from homeowners and designers to contractors, architects and commercial builders. Over 1300 Semihandmade projects were completed in 2015. Also in 2015, Semihandmade made Inc. Magazine's list of the 500 fastest-growing private companies in the US.
 Sequence-matched Walnut, Teak and Mahogany veneer doors are the company’s signature look. More exotic selections include Reclaimed Lumber, Rosewood and Zebrawood, as well as collaborations with companies like Art of Board (recycled skateboards) and Stikwood (reclaimed lumber). 
IKEA-priced styles such as paintable Shaker and Slab, textured melamine, and colored thermofoil complete the Semihandmade selection.  
 In April 2016, Semihandmade will launch its PRINT line of IKEA doors in collaboration with artists Rex Ray, Lisa Congdon, Erik Abel, Eloise Renouf, Elizabeth Olwen and others. Also this Spring, Semihandmade will open a third showroom inside shared-space WeWork Grant Park Chicago in preparation for the launch of a private-label line of bathroom, media and storage cabinets at NeoCon in June. 
Additional WeWork openings planned for 2016 include Brooklyn, Austin and Seattle.  
Links for show notes: