Christopher Lochhead’s Legends & Losers

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203: Leah Busque Engineer to Entrepreneur to Startup Investor

Why is the "gig economy" more than what its moniker entails? What kind of thoughts does a young woman looking for her first job out of college have? On today's episode, Leah Busque, founder of TaskRabbit and venture capitalist at Fuel Capital, shares her journey.

"Flexibility in the future work is one big pillar, one big category... Over the course of the last decade, we've just seen that pillar, that value explode across all these different companies and all these new ways of working." - Leah Busque

Three Things We Learned

Flexibility in new ways of working

Leah founded TaskRabbit in 2008 because of the financial crisis that hit the US in September that year. With the catalyst that began the shift and change around how people perceived the future of work, she thought it was an incredible time to start a company based around new ways of working. With the instability of the financial markets also came the emergence of flexible ways of working which more and more people loved and appreciated as the years went by.

Trade-offs of choosing flexibility

The "gig economy" is a term that usually would feel demeaning for freelancers who choose to manage their own schedule and choose to work with people they want. But even the traditional benefits that come with secure jobs will have to marry this flexibility-driven economy in the future. All it's going to take is the consistent push of companies and workers for this to happen.

Long-term jobs are now growing less possible and desirable

The workforce is changing and companies are undergoing the same changes to meet the rapidly evolving demands and expectations of the next generation of workers. The past generations would commit to jobs for decades and then retire. But at present time, companies will be hard pressed to find a 22-year-old with a set goal of staying with them forever.

Leah herself had her parents as her models when she was still starting out as part of the workforce. With IBM being one of the most nurturing companies for female employees, she had in her head to climb up the ladder and build her dream career within it. But long story short, that didn't stay true.

Bio / Story:

Leah Busque is an engineer turned entrepreneur turned venture capitalist at Fuel Capital. She founded TaskRabbit in 2008, which was then later acquired by IKEA in 2017.


We hope you enjoyed Leah Busque on this episode of Legends and Losers! Christopher loves hearing from his listeners. Feel free to email him, connect on FacebookTwitter, Instagram and subscribe on iTunes!


202: Legends and Losers Unlocked Go Ugly Early

On Episode 183, multi-time Silicon Valley CEO Jay Larson joined Christopher Lochhead in a dialogue that left many impressions. An executive admired by a lot of people in the marketing sphere, he said some amazing tidbits that until now Christopher looks back on. Today, the host mulls over some of the most resounding words left by the CEO of red-hot company Optimizely—to go ugly early.

"In the sage words of Jay Larson, when you have bad news, go ugly early." - Christopher Lochhead

Jay Larson - Getting to the Ugly Early

This advice is exactly the opposite of what most people would think when they have bad news waiting to be unveiled. Anyone can be guilty of delaying the inevitable, be it a CEO or a politician.

When there's bad news and they have to go on TV, they would most probably go on about things that may not be relevant to the real issue. They meander around and try to remind people about how great they are before dropping the bomb.

Undermining Yourself

When you fall prey to the bad news and don't put it right on the table, you communicate to everybody that you're not on top of it. You fail to be professional, unable to show that you have a grasp of the facts.

It doesn't matter whether you are an entrepreneur, a CEO of a company or a leader of any kind. Not dealing with and resolving a bad news upfront mean undercutting your power.

Facing the Ugly Head-on

Dishing out the good news before the bad is disservice to both you and your constituents. This doesn’t help address the problem at all, and it reflects badly on your leadership skills and ability to manage a business situation.

By being honest with the status of your business, you will be braver in fixing the problem, and so will everyone around you. So go ugly early.

Listen and download to the episode now!


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.


201 Dr. Jacob Towery Child & Adolescent Psychiatry

On today's episode of Legends and Losers, Christopher talks to Dr. Jacob Towery about raising mentally strong kids and what to do if someone is having a mental health problem and how to handle it if someone in your life might be suicidal. All this including why it's cool for a doc to rock a mohawk on Dr. Jacob Towery: Child & Adolescent Psychiatry.
Before throwing 100% of your energy into getting your child help, it's worth pausing and see if you...have any issues... - Dr. Jacob Towery

Three Things We Learned

Communication is Critical

To say to a parent, "If your kid is acting whacky, have you considered it might be you?" is a tough thing to say to a parent in today's society.  But direct communication is crucial and effective if done correctly. Dr. Towery is incredibly direct to everyone in his life but is also very thoughtful in his approach.  He's not afraid to address the elephant in the room yet does so deftly and without talking down or being disrespectful.

What the F*ck is Wrong with Men?

Like most men, Christopher and Dr. Towery were shocked and embarrassed when the "Me Too' movement started. To discover that men had been such assholes throughout time. It's now men's responsibility to better through future generations of boys and men. Dr. Towery isn't an expert in this area but believes that testosterone when unchecked in the absence of role models of how to use strength and power responsibly, can lead to violent episodes. Masculinity is great but not toxic masculinity.

A Good Place to Start

Pediatricians are a great resource if you have questions about your child's mental well-being. Always start with an assessment. Someone that is reliable, responsible and that is not just desperate for getting the most clients. A great place to start is just to find out what's going on with a neuropsychological assessment or evaluation and gathering more data before doing anything drastic.
To hear the rest of the conversation, download and listen to the entire episode!


Jacob Towery, MD, is an adolescent and adult psychiatrist in private practice in Palo Alto, California.
He attended Duke University for his undergraduate studies, the University of Virginia for medical school, and Stanford for his residency in adult psychiatry and fellowship in adolescent psychiatry.
Dr. Towery currently serves on the Adjunct Faculty at Stanford University School of Medicine.
Dr. Jacob Towery enjoys seeing patients, teaching, snowboarding, scuba diving, traveling, reading, meditating, spending quality time with other humans, making long lists, Oxford commas, and writing about himself in the third person.
More information can be found at
We hope you enjoyed Dr. Jacob Towery on this episode of Legends and Losers! Christopher loves hearing from his listeners. Feel free to email him, connect on Facebook, Twitter, Instagram and subscribe on iTunes!

200: Jaime Jay Trading Legendary Stories

Legends and Losers has always aspired to capture lightning in a bottle and be a podcast unlike any other while adding value to people's lives. But this show is as silly as it is plentiful of knowledge. On this 200th episode, Christopher Lochhead and Jaime Jay trade stories both ridiculous and legendary.

"Get out and experience life a little bit." - Jaime Jay

Jaime Jay - Crazy Airplane Tales

Some airline has finally come up with an addition to their business class seats that passengers wouldn't want to miss—pillow menus. This successfully reinvents the word, "chillax". People can now pick their preferred travel companion from a wide array of pillows and cases.

In true spirit of airplane anecdotes, Jaime also shares an oily plane story involving a woman with a bouffant do and the greasy spot unfortunately branded on a plane seat.

Befriending Your UNI

When it gets lonely, people can turn to UNI. A magic AI friend, UNI can be your companion one tap away. UNI can do anything from chatting to dancing, and while it's terrible, the UNI phenonemon is something we can all learn from.

Business Buzzwords to Kill

Some business buzzwords deserve to die in 2018. While they have revolutionized the sphere, some have become obsolete. This not only springs from a creative standpoint, but also from the fact that language constantly evolves.

Solution, for example, is a word everybody uses but is hardly ever meaningful anymore.

“Solution—I hate that word… Whenever I think to say 'solution', I check myself and I try to think about another word that I can use that’s more meaningful and identifies whatever it is I’m talking about rather than just vague, old ‘solution’.” - Jaime Jay

To hear more incredulous stories and why words like ‘disrupt’ and ‘solution’ should be considered throwaways from Jaime Jay and Christopher Lochhead, download and listen to the episode!


Jaime Jay (twitter: @heyjaimejay)

Jaime Jay is the Managing Director of Bottleneck Virtual Assistants, a Life & Business Coach, host of the popular Stop Riding The Pine Podcast, and co-producer of “dialogue podcast” “Legends & Losers”.


199: Questions and Cocktails with Christopher Lochhead #1

In this first episode of Questions and Cocktails, Christopher Lochhead answers questions from his legendary listeners. People from different walks of life send in their emails, and Christopher dishes out some unfiltered pieces of advice.

“Like in anything, most people quit. And if you wanna be successful, you gotta stick to it.” - Christopher Lochhead on staying true to your podcast's brand

Young Professionals in an Aging World

Aaron, a Doctorate of Pharmacy and MBA student shares how listening to a tech industry podcast has offered him a different perspective of his own niche. Bloated with inefficiencies, his industry has seen zero progress in innovations. In a field where earning tenure means respect, he and other young professionals struggle to be taken seriously.

How can young professionals with an entrepreneurial spirit gather the respect to have the real conversations and cause change in an industry run by older people?

"Don't let anyone stop you from bringing your ideas forward. There are some older people in business who do stay curious. They are open, they will be your allies." - Christopher Lochhead

Starting a Podcast

An anonymous listener who once heard Christopher guest in Jordan Harbinger’s show seeks advice on how to start their own podcast. After years of being a chef and handling different food establishments and services, they are now ready to express themselves in some other way. They hope to bring more light to what they do beyond glorified social media posts on success.

Christopher gives a couple of tips on how to launch a successful podcast. He suggests getting a producer and editor to deal with the technical aspect of podcasting and building a brand that reflects both the personality of the host and their vision.

To learn more from Christopher in this edition of Questions and Cocktails, listen to the episode now!



198: David Cancel Engineer to CEO

David Cancel is the co-founder and CEO of Drift, one of the fastest growing companies in the marketing space. A former engineer, he's also a podcaster and author. Today he joins Christopher Lochhead to talk about building massive technological startups, sabbaticals, books, and why conversational marketing is the future.

"For me myself, engineer to tech to product to now, CEO... they're kinda like a progression of the same thing... It's like I'm trying to create our own world." - David Cancel

Three Things We Learned

  • Anxiety-ridden break
When they first put up Drift, David and his team figured to create a tradition of taking a sabbatical every three years. But his turn to take temporary leave from work came with the worst possible timing. His wife pointed out the fact that if he didn't do it now, no one in the company was going to follow through, and so with tons of anxiety, he cashed in on the leave.
  • Pulling off a sabbatical with a great team
While his learning sabbatical offered lots of time to meditate and examine his life and willingly be at the beck and call of his daughter, some things broke. They were nothing he couldn't fix though. He had his management team whom he could lean on while he set an example for all of Drift's 190 and some employees to thank for that.
  • A startup faster than a rocket ship
Prior to Drift, David was the Chief Products Officer at Hubspot, another hugely successful company. The culmination of his experience from being part of large-scale bodies aided in growing Drift. And now his business is doing amazing, faster than any other company within and without their category.

Building a startup is one tough endeavor. Growing one is even more difficult because then you will have to learn how to brake and not implode. But with a team behind him willing to stay true to their visions from the get-go—sabbaticals included—, David thinks they can do it all.


David Cancel is a serial entrepreneur, podcast host (Seeking Wisdom) and angel investor/advisor.  
Best known for creating hypergrowth companies, products and product teams at companies such as, HubSpot, Performable, Ghostery and Compete.  
David has been featured by media outlets such as The New York Times, Forbes, Fortune, Wired and Fast Company. David has guest lectured on entrepreneurship at Harvard, Harvard Business School, MIT, MIT's Sloan School of Management, Bentley and other Universities.  
His popular blog has been read by 1M+ entrepreneurs, and his Twitter account @dcancel has 180k followers and is considered a "Must-Follow" account for entrepreneurs, executives and product people. 

197: Psychiatrist Dr. Darold Treffert Cure Sometimes, Help Often & Comfort Always

Dr. Darold Treffert is a psychiatrist and the world's leading expert on savants, genius, and autism. He has an unparalleled commitment to children and learning and a deep understanding of what makes us human beyond the Homo sapiens sapiens brain. Today he shares the beauty of early intervention, some incredible stories, and insights to us look differently at life.

"It is just an amazing difference early intervention makes. I think we'll see the payoff of that eventually in terms of preventing some of the impairments that go with autism." - Dr. Darold Treffert

Three Things We Learned

  • Making early intervention possible

Dr. Treffert started a center to offset a growing list of children who needed intervention and were forced to wait for nine to twelve months to be accommodated. The effort didn't aim to merely expand. They took on the role of teaching educators and therapists to affect change in a system thwarting progress for early intervention programs.

  • The earlier, the better

According to Dr. Treffert, diagnosis of learning differences is best done for children around the age of two. Many areas offer free intervention programs for parents who wish to have their children evaluated. But the difference in progress of children subjected to early interventions and those made to wait is striking.

  • The Treffert Approach

Dr. Treffert and his team have come up with a five to six-step process that they impart to therapists and educators in an effort to optimize the intervention programs for children with autism. Making the right differential diagnosis leaves the door ajar for other possibilities involving a child. A multidisciplinary approach is also tantamount to ensuring that all areas of a child's development are properly examined.

There's a plethora of approaches for intervention. But the process must involve not only professionals and parents who know their children better. Integrating them in early intervention programs can make all the difference in a child's progress towards realizing their hidden potentials.


Dr. Darold Treffert is an alum of the University of Wisconsin Medical School in 1958, intern in Eugene, Oregon, and a resident in Psychiatry at University Hospitals in Madison, Wisconsin. Two years after joining the staff to develop the Child-Adolescent Unit of Winnebago Mental Health Institute, he was named Superintendent in 1964. After 15 years of service in the position, he divided his time between the private practice of Psychiatry and a position as Executive Director of the Fond du Lac County Health Care Center.

An internationally known researcher on Savant Syndrome, he has published several books and journals. Extraordinary People: Understanding Savant Syndrome, published in 1989, has been translated and published in eight other countries. His most recent book on the topic—Islands of Genius: The Bountiful Mind of the Autistic, Acquired and Sudden Savant—was published in 2010. Mellowing: Lessons from Listening has also been widely distributed, an earlier book on preventive mental health and stress management. Featured in various talk shows and documentaries, Dr. Treffert was a consultant to the movie Rain Man, in which Dustin Hoffman portrays an autistic savant. He maintains a Website on savant syndrome through the Wisconsin Medical Society.

In 2006, Dr. Treffert received the National Torrey Advocacy Commendation from the Treatment Advocacy Center in Arlington for his efforts on behalf of mental health law reform and treatment access for the severely mentally ill. He has been listed in The Best Doctors in America, by peer selection, beginning in 1979.

Dr. Treffert has been a clinical professor at the University of Wisconsin Medical School and the University of Wisconsin--Milwaukee.  In 2016 Agnesian HealthCare established the Treffert Center on the campus of St. Agnes Hospital to preserve, expand and disseminate Dr. Treffert's work on savant syndrome and other forms of exceptional brain performance. It contains assessment and treatment clinics for autism and related disorders, and the Treffert Academy, a strength-based school for neurotypical children and those with special needs. Information about the center can be accessed at



196: Duncan Davidson Why Machines and People Are Going to Live Happily Ever After

Duncan Davidson is a multi-time billion-dollar company creator turned venture capitalist. He co-founded Bullpen Capital in Silicon Valley. In this episode, he talks with Christopher Lochhead about the coming robot apocalypse and what to do about it, the impact of universal basic income and whether we should have one, and why machines and people are going to live happily ever after.

“There are people building these AI-assisted support systems… What it means is a truck driver who's at least an empathetic character can get plugged into this computer support system, totally different job, and very, very quickly become extremely successful.” - Duncan Davidson

Three Things We Learned

  • A history of the Luddites

In the early days of automation, people who worked in garment factories lost their jobs when steam engines were installed to run the spinning machines. These people, called the Luddites, complained about their loss and asked for financial assistance for their trouble. The powers that be never listened to them, and they treated this with violence, prompting their exile to a foreign land as criminals.

  • History repeats itself

If we look at the history of technology since the Luddite situation back in the 1800's, there's a recurring trend. Every thirty years, a new technology comes along—the steamship, railroad, electricity, cars. People lose their jobs, and they lobby for their rights, but the authorities turn deaf ears to them, and life goes on in the new era.

  • More jobs are created than displaced by new technology

Ten times more jobs were created by automation than were lost by the Luddites. They did lose their specific jobs, but because of the new opportunities for other people, nobody else raised concerns. New technology often signals a wonderful time for humanity, and still, there are modern Luddites who will ask after what a truck driver is going to do now that he's lost his job.

There has always been the debate of whether any new occurrence of technology will be different than the last. But looking into history’s natural course, should we really concern ourselves with the feared robot apocalypse when it's bound to birth ten times more jobs than will be lost?


Duncan Davidson is General Partner at Bullpen Capital where he focuses on forward-leaning technology investments.

He is a serial entrepreneur who most notably founded Covad Communications (the leading independent DSL provider, went public and reached a market value of $9B) and Sky Pilot Networks (developer of outdoor wireless mesh systems, acquired by Trillium in 2009 for connectivity to smart meters).

He served as the SVP of Business Development at InterTrust and led the IPO in 1999 and the second in 2000 (InterTrust reached a $9B market value in 2000).

He spent four years as a managing director at VantagePoint Venture Partners where he focused on digital media and telecom investments including Widevine (acquired by Google) and Livescribe.

Prior to Bullpen, he co-founded one of the first mobile social app companies, Xumii, later sold to Myriad Group and now powering over 200M users in the developing world.

At Bullpen he focuses on SaaS, blockchain and IoT investments, and is an advisor to or sits on the boards of Drive Motors, Filament, Hologram, Illumeo, SpaceIQ, Verbling and Wag Labs. He received a Sc.B. in physics/math from Brown University, with Honors, and a J.D. magna cum laude from Michigan Law School, where he was Order of the Coif and a member of the Law Review.



195: Dr. James Kelley The Crucible’s Gift

Dr. James Kelley is the author of The Crucible's Gift and a professor of marketing at the United Arab Emirates University. In today's episode, he sits with Christopher Lochhead to talk about why failure and losery make us who we are, why every crucible moment is a gift, and why being an authentic leader matters.

"The reality is if I just step back, the only person I need to prove myself to is me." - Dr. James Kelley

Three Things We Learned

  • The struggle of proving oneself

Dr. James Kelley has had an ongoing struggle of wanting to prove himself to somebody. This constant bout of inadequacy all stems back to a time when he felt like he wasn't the kid that could amount to anything. But in the end, he knows that he can only do so much about what other people think.

  • Striking the balance between family and profession

There's a fine line between being great at our career and doing a great job family-wise. Whatever our profession, we all want to achieve a level of mastery, success, and recognition in our field. But ultimately, the people we need to be kindest to are the same people who will take care of us when we're past our prime and have done what we must.

  • Writing to be part of a crowd can be hard

Dr. Kelley admits that writing a book is tantamount to being part of a group of people who have written nice books, bias and all. But he also confesses to feeling like he could've done better, that there are parts he could've made stronger. If he were to rewrite these parts, the book perhaps wouldn't be any better, but at least he could be happier.

Some people have gone out of their way to do their own thing while others are trying to jump in. Some people write books to capture moments in their lives or to capture history of their long-standing endeavors. We all have different journeys, crucible moments included, and we're all trying to get through them.



Who is Dr. James Kelley?  

His path is still being built brick by brick and the current brick is his inaugural book: The Crucible's Gift: Five Lessons from Authentic Leaders Who Thrive in Adversity.  

The book is based on interviews from 140+ executives, from Fortune Two companies to entrepreneurs and everything in between.  

The book unpacks the journey a leader takes to become a more authentic leader, starting with their crucible moments as the springboard.   

Against the laws of nature and human belief, in 2010, Dr. Kelley completed his Ph.D. in International Marketing at the University of Western Australia in Perth, Australia and ascended to higher education to work in Philadelphia. Prior this miraculous event, James spent time living in Japan, New York City, San Jose, Portland, and Chicago.   

At each stop James added work, life, and failure in his bag of experiences.   

Today, James, his wife Mary, and his four kids live just outside of Dubai where he teaches, writes, and produces is bi-weekly podcast Executives After Hours.  

The podcast is predicated on interviewing executives about their personal journey. The shows motto, "I care about who you are, not what you do, because what you do defines who you are." In addition, he is a professor of marketing at The United Arab Emirates University.



194: Morgan Wright What Parents Should Know, Cyber Security & How to Avoid Scams

How does the digital world affect political climate? Is Facebook really on top of election hacking and private data compromise? In today's episode, Morgan Wright sits with Christopher Lochhead to break down influence and interference, how to avoid scams, and social media's effects on teenage suicide.

"The difference between interference and influence determines how we respond to what happened." - Morgan Wright

Three Things We Learned

  • Interference is a violation of sovereignty

There are 50 nation states in the US. With this comes the many voting systems that can make it pretty difficult to ensure that no voter fraud happens come election time. But since there has been no recorded voter fraud, there is technically no instance of a nation-state acting against the US, and therefore no interference.

  • Influence is a valid national objective of a nation state

Influence operations have gone on since time immemorial. The most obvious example is the effort to stop the spread of communism in the Western Hemisphere. However, influence has only recently become a hot topic in this digital age thanks to the massive amount of data shared through social media platforms.

  • Russia's had a hundred-year head start in running influence operations

Reports of Russia's efforts of compromising information to run their influence operations date as far back as 2015. But it wasn't until a bunch of kids were able to access classified information that Facebook was tossed into hot water. This dissonance shows how truly behind the US is in all this.

Hacking has always been a threat and a potential tool to use against humanity. But then there's also fake news, the generation and spreading of disinformation, which influences people's mindset. Psychological warfare pits people against each other and divides even the biggest nations and most thriving of economies, and the US is no exception.



Morgan is an internationally recognized expert on cybersecurity strategy, cyberterrorism, identity theft and privacy.

He is President and Chief Development Officer for RadiusAI.

He currently serves as a Senior Fellow at The Center for Digital Government and is a national security opinion contributor to

Morgan's landmark testimony before Congress on changed how the government collected personally identifiable information.

He’s made hundreds of appearances on national news, radio, print and web including CNBC, Fox News, Fox Business, CNN, ABC, NPR, NBC and more. Previously Morgan was a Senior Advisor in the US State Department Antiterrorism Assistance Program and Senior Law Enforcement Advisor for the 2012 Republican National Convention. In addition to 18 years in state and local law enforcement as a highly decorated state trooper and detective, Morgan has developed solutions in defense, justice and intelligence for the largest technology companies in the world including SAIC, Unisys, Alcatel-Lucent and Cisco.

He’s a contributing author for the 4th Edition Computer Security Handbook, and has been quoted in 2 New York Times bestsellers (Sharyl Attkisson: Stonewalled and Carmine Gallow: Talk Like TED).