Legends & Losers – The Christopher Lochhead Interview

Christopher Lochhead helps people create legendary businesses to give them the life of their dreams.

If anyone’s in a position to succeed with this mission it’s Christopher. After all, his experience includes 30 years as a Silicon Valley CMO, advisor, coach and Board Director to over 50 venture-backed startups.

These included Mercury, a company Christopher helped grow from a $1 billion valuation to its eventual $4.5 billion sale to Hewlett Packard. So when Christopher says legendary, he means it.

In this interview, we get to grips with Christopher’s biggest success, his biggest failure, his inspirations, what makes the Legends & Losers podcast so unique and what the future holds for this maverick businessman.   

Tell us about yourself.

I’m on a mission to help people design a legendary business and a legendary life while having a very good time.

I host the popular Legends & Losers, one of the few real, raw, “authentic dialogue” podcasts and I coAuthored for Harper Collins the “instant classic” – “Play Bigger: How Pirates, Dreamers and Innovators Create and Dominate Markets.”

For 30 years I worked as Silicon Valley public company CMO & advisor/coach/board director to over 50 Silicon Valley venture-backed startups, and I’m a former “small e entrepreneur”.    

Why did you start Legends and Losers?

I want to make a difference in the world.

Readers of my book “Play Bigger” were asking for more about category design, entrepreneurship and life lessons. So Legends & Losers is, in part a response to that.

Secondly, I was sick of listening to the traditional bullshit on formulaic “interview shows”.

On a traditional TV or radio show and even podcast, what we experience as listeners is a professional host/journalist, with a pre-fabricated narrative, questioning a highly accomplished person who has been media trained, who comes to the interview with their key “talking points”.

Then we as listeners experience a collision of guest talking points and journalist narrative. Not anything that resembles a real conversation.

So Legends & Losers in a very real way, is the podcast I wanted to listen to.   

What makes the show unique?

We believe that one real conversation can change your life. Our goal is to have authentic dialogues with amazing people about what it really takes to design a legendary business and a legendary life, while having a lot of fun.
People have said we’re like eavesdropping on a business conversation in a dive bar.    

What was the most important lesson you learnt during your time as a Silicon Valley CMO?

Legendary entrepreneurs and leaders do more than build a great product and company.

They are unique. They are original.

They design a new category AND product or service that introduces the world to a new way of thinking about a problem and solution.

And when category design works, you become known for a niche that you own. This is what the greatest companies do. And it turns out, people who have legendary careers do the same thing.   

Was Mercury’s acquisition by HP for $4.5 billion your biggest career win?

In some ways, yes. Because we designed and dominated a giant new category and became a category king.

In my opinion that is the greatest achievement in business.

But, on another dimension, the success of Legends & Losers and Play Bigger are my biggest “wins”.  Reason being, both the podcast and book are making a difference at a much bigger scale.

The success of Mercury made a difference to our approximately 3,500 employees, to HP, our customers, partners and investors. Which is very cool.

The popularity of Legends & Losers and Play Bigger means that I have a chance to make a contribution to people on a much more massive scale.    

What’s been your biggest failure?

I’ve been involved with more failed businesses that I can count.

I’ve been fired more times than I can count.

And I’ve lost a lot more money than I’ve made.

The two losses that made the biggest difference in my life where the failure of my first business and the failure of CRM company Vantive (my 1st silicon valley CMO gig).

Failing in my first business hurt the most and was financially terrifying. When we crashed, I was 21, unemployed, newly married, in debt, with no education and almost no job prospects.

Vantive hurt because Siebel Systems beat the shit out of us to become the original category king in sales automation/Customer Relationship Management. It felt like a long horrible beating in public. Like a mis-matched boxing match that wouldn’t end.

The whole time they we’re smashing us, I kept thinking, “I’m not the guy who gets beaten, I’m the guy who does the beating!”

The loss to Siebel taught me how fast you can have your ass-kicked. And that I never wanted to be on the losing end of a high-stakes category battle again.   

How did you bounce back?

I got right back into the ring and became the founding CMO of a tech startup.


If you had to give us one episode to listen to which would it be?

This question is kind of like asking a parent who their favourite child is. That said, this episode with Bix Bickson will alter your mind, life and business.    

What advice would you give to someone starting their small business?

Categories make companies. The most legendary businesses and individuals become known for a niche they own. Do not make the mistake of just building a great product and company.


Where do you draw inspiration from?

Other people who made a huge difference in the world. We live in a world that tries to drag us down.

I love the people who slay the cynicism of our times with their dreams.  I love the pirates, dreamers and innovators who have the courage to be legendary.


Finally, what does the future hold for Christopher Lochhead?

My big dream is that one day most people focus on the exponential value of what makes them different vs. the incremental value of what makes them better.

I work every day on how to make the biggest difference I can, while having a very good time.

We’re working to make legends & losers one of the most popular podcasts in the world and with my dear friend Heather Clancy I have a new book coming out later in 2018 called, Niche Down: How to become legendary by being different” that we hope people love.

   With thanks to Christopher Lochhead. To discover more about the legendary Legends and Losers podcast visit the website.   

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