Christopher Lochhead’s Legends & Losers

Christopher Lochhead’s Legends & Losers header image 1

193: A Niche-nado is Coming

Which industries are Niche-nado ready? What should you do to make the most out of the opportunities they present? In today's episode, Christopher Lochhead discusses three things that have come up since the release of Niche Down. 

"Today's solutions are tomorrow's problems." - Christopher Lochhead

Places of Opportunity  

Opportunities to design or redesign new categories may exist in any industry. They can be found in places that have been dominated by complacent, giant companies. 

Such bureaucracies tend to gravitate towards established systems instead of creativity. They tend to be blind to different aspects.

Niche-nado Industries

Few industries to consider are consulting, financial services, and content/media. Author of Superconsumers Eddie Yoon thinks that there is a lot of opportunities in industries with intellectual capital. His success as a consulting guru is already a prime example of a niched-down business. 

When it comes to the financial services industry, millennials have had enough of the banks' incremental gouging. According to Gallup research, only 30% of them are engaged with a retail bank. Apparently, more compelling and innovative options are yet to be implemented.

Designing a Niche in Content/Media

Nowadays, ads are popping almost everywhere. But, there are also a lot of micro-niche opportunities that come with them. An example is the July Holiday activity on the Hallmark Channel. 

Unique forms of content/media have also appeared, such as podcasts and Korean dramas. Ben Thompson's Stratechery newsletter is also a very good example of a refreshingly innovative form of content. 

Listen and download the episode now to hear more! 


Superconsumers by Eddie Yoon
Stratechery by Ben Thompson
Chris Ducker Youpreneur Category King
Book - Niche Down


192: Government Funded Attack on Podcasts

Are you somebody who loves independent podcasts? Today Christopher Lochhead shares an urgent news that can change the independent podcasting industry as we know it. Independent podcasters need your help to combat the government funded attack on podcasts.

"In part because of our government, independent podcasting just got harder." - Christopher Lochhead
A Devastating News
An article from Wall Street Journal dated August 15 brought about the news that Public Radio International (PRI) and Boston-based Public Radio Exchange (PRX) are in a bid to capitalize on the growing popularity of podcasts. This can incapacitate independent podcasters to a high degree.

The US government funds the creation of podcasts by PRI as well as those of public radio stations all over the country. Taxes paid by the citizens go to public radio and have been going to public radio podcasts for a long time now. With the merger of PRI and PRX, they will be even more capable of outdoing independent podcasters by raising the competition bar even higher against these independent shows.

Independent Podcasting at a Huge Disadvantage
The new enterprise will have its headquarters at Boston, potentially reaching up to five million monthly users via 585 radio stations. This figure does not include the listeners who contribute to the sixty million monthly downloads of podcasts. 

PRI hosts the number one podcast in the United States. The reinforced support from the government itself will toss the chances of success for independent podcasters into the wood chipper. Our shot at reaching a wider audience will be close to none, all thanks to this attack orchestrated by the government and affiliated media companies.

Independent Podcasters Need You
We need your help to survive through the government funded attacks on podcasts. Dropping ratings and reviews on our shows will go a long way, and this is only one of the many things you can do to support us. Help us keep the shows we built for years running, help us help you enjoy the content you love for longer.

Listen and download to the episode now to hear more!

191: Unlocked - I’d Rather Be a Bitch Than a Victim

In Episode 150, venture capitalist Magdalena Yesil shared with us how taking risks has pushed forward her entrepreneurial career. Christopher Lochhead mulls over one striking line of hers during their dialogue in this Unlocked episode.
“I’d rather be considered a bitch than a victim.” - Magdalena Yesil
Three Things We Learned
  • So many of us go out of our way to be liked
Christopher recalls times when he worked to hard to please other people. He has also tried to assume the version of him that people wanted him to be instead of listening to his own heart. Most people are guilty of this, and it’s not healthy at all.
  • People have forgotten how to be candid
Our world today is defined by heavy political correctness that can be suffocating, but we have also forgotten how to be honest with each other. Humans tend to sugarcoat things in order to avoid confrontations. We’re no longer straight with the people around us, accommodating them in a way that is by no means correct.
  • People are going to call you what they want to no matter what
And you can only hope that whatever name they come up with, it’s good. But even then, isn’t it better to be called names because you’re strong and able to make a difference in the world?
Wouldn’t it be better to be considered a bitch than be a victim? Someone willful and headstrong rather than someone who say sweet things in order to earn useless favors?


Pioneering Silicon Valley entrepreneur and investor Magdalena Yeşil came to the United States in 1976 with two suitcases and $43, blind to the challenges she would face as a woman and immigrant in Silicon Valley. Today, she is best known as the first investor and a founding board member of Salesforce, the now-multibillion dollar company that ushered in the era of cloud-based computing. 
Magdalena Yeşil is a founder, entrepreneur, and venture capitalist of many of the world’s top technology companies, including Salesforce, where she was the first investor and founding board member.
Yesil is a former general partner at U.S. Venture Partners, where she oversaw investments in more than thirty early-stage companies and served on the boards of many.
A technology pioneer, Yeşil founded three of the first companies dedicated to commercializing Internet access, e-commerce infrastructure, and electronic payments.
UUnet, CyberCash, and MarketPay earned her the Entrepreneur of the Year title by the Red Herring magazine. Yeşil is a founder of Broadway Angels, a group of female venture capitalists and angel investors. She is currently working on her fourth startup, DriveInformed, a technology company bringing trust and transparency to the auto finance industry. She serves on the board of directors of RPX, Smartsheet, and Zuora.
Magdalena is an immigrant to the United States from Turkey and is of Armenian heritage. An avid hiker and sailor, she lives in San Francisco, California.

Magdalena Yesil


190: Tiffani Bova Your Growth I.Q.

What is it like to stand in the shoulder of giants? How to build a successful career in tech that will last for many years? Author, Speaker, and Salesforce Evangelist Tiffani Bova shares the importance of improving your growth I.Q.

"Diversity is much broader than gender that ultimately it just makes teams more effective and companies more effective." - Tiffani Bova

Three Things We Learned

  • Writing provides a better understanding

For many business people, writing is better than thinking things through. It allows for a wider perception, revealing things that might not have been considered or expected to be achieved in the process. Had people known them earlier, they could have acted differently in the playing field.

  • Growth is about combination & timing

Growth isn't about the actions or tools used. It is about finding the right combination and its proper sequence that make people completely rethink their business. Without the right operational sequence, the right idea can still fall short.

  • Every person or business is unique

People sometimes stray from their core message. They tend to forget who they are and what they do as they pursue their goals. But that shouldn't be. What they can do instead is to return to their true identities, compete in that arena, and amplify what they are supposed to.

When thinking about growth strategies, one should also think about the context of the market concerned. The context is unique to every business. Understanding the necessary components for growth is important.


189: Russ Fradin Silicon Valley CEO

How do you successfully build companies and categories? How do you overcome failure and come up with a fantastic product that goes beyond its minimum value? Experienced serial entrepreneur and CEO Russ Fradin shares this and much more on this episode.

"You should solve real problems for real companies with a fantastic team, and if you can do those three things you will be fine." - Russ Fradin

Three Things We Learned

  • Start with a team
Everyone says this but the first ingredient to success is a great team that you trust. Russ considers himself very fortunate for having two co-founders at Dynamic Signal that he's worked with for decades across multiple companies. The experience and lessons learned from having a base level of folks you have known for a long time can't be replicated.
  • Solving real problems
Russ and his team have adopted a solutions-first mindset in building their company. One can build a lot of things and show people solutions to problems they never knew they had. They have learned throughout the years that business success is beyond creating legendary products.
  • Building a product for an industry that requires it
On their first venture, Russ and his team created products that were, simply put, fantastic. However, it soon dawned on them that they had to build products that would fill in a gaping hole within an industry. By coming up with a product that went beyond its minimum value and features, they were able to flourish in the enterprise world.

Russ and his team started the company building a great product to solve a problem for their customers. Thanks to the fact that they had a great product, they had enough trust from their customers to spend an ample amount of time to devote to realizing that there was a much bigger problem that they could solve at the same time. And this is how they were able to hit the nail on the head and become the successful company that they are now.

Russ Fradin is a digital media industry veteran with more than 15 years of experience in the online marketing world. He co-founded and was CEO of Adify, which was acquired by Cox in 2008, and he also co-founded SocialShield. Russ was also SVP of Business Development at, Executive Vice President of Corporate Development at comScore, and was among the first employees at Flycast, which was acquired by CMGi in 2000. He is an active angel investor in the digital world and currently sits on a number of boards.

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.