Christopher is the co-author of Harper Collins’ “instant classic” Play Bigger: How Pirates, Dreamers and Innovators Create and Dominate Markets and he’s the co-host of the Legends and Losers podcast. He is a former three-time public company CMO and entrepreneur. Fast Company Magazine calls him a “Human Exclamation Point”, The Marketing Journal says he’s one of “The Best Minds in Marketing”, and The Economist calls him “off-putting to some.”
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- Zoom – Christopher’s small business resource
- Legends and Losers – Christopher’s website
- Legends and Losers – Christopher’s podcast
- Play Bigger: How Pirates, Dreamers and Innovators Create and Dominate Markets – Christopher’s book
- The Mastery Journal – Master productivity, discipline and focus in 100 days!
3 Key Points:
- Look for your opening, create your OWN category and dominate the space.
- Build relationships with people; your community is your support.
- Prosecute the magic triangle—product/service, company, and category (that makes you distinct).
Time Stamped Show Notes
(click the time stamp to jump directly to that point in the episode.)
- [01:05] – Christopher was thrown out of school when he was 18 for being stupid. At 21 years old, he learned he was dyslexic and felt he only had two options: work in manual labor or be an entrepreneur. He chose the latter. He is now living in California with his wife and surrounded by his tribe
- [01:58] – One BIG and Unique Value Bomb: Christopher is a category designer
- [03:33] – Entrepreneurs pull two big levers: product/service and company, but the legends pull a third lever where they create a category and position themselves as distinct
- [04:16] – When the three levers are pulled off correctly, it is called “prosecuting the magic triangle”
- [04:57] – Worst Entrepreneurial Moment: Christopher’s podcast is called Legends and Losers because you can’t be a legend without being a loser first. When he was 18, Christopher did not have any options and he was pushed to become an entrepreneur. When he was 21, the company failed and he had a hard time getting a job. He was in debt
- [06:56] – JLD says what contributed to his personal success with Entrepreneurs On Fire is the relationships he has built with his guests on the podcast
- [08:04] – “Position yourself or be positioned”
- [10:16] – Greatest AH-HA Moment: Christopher was working on his second startup in the technology industry. He saw the early days of sales force automation. He felt a new category was being built and wanted to be one of the first people in customer relationship management. He positioned his business as the leader in a new category of technology
- [11:23] – This was Christopher’s first experience in building a new category
- [12:13] – JLD says there are new categories that are waiting to be created, but you have to have patience in finding the right one for you
- [12:58] – Christopher says JLD is an intuitive category designer; these are people who teach the world to look at a product in a new way
- [13:17] – JLD was not only early in podcasting, he also had the magic triangle right
- [14:03] – JLD created a category of podcast he could dominate
- [14:40] – What are you most FIRED up about today? – “I get to have incredible conversations with incredible people”
- [15:03] – Christopher read an article on The Wall Street Journal, The Crisis of American Entrepreneurship
- [15:31] – For Christopher, entrepreneurship was a way OUT, not UP
- [16:02] – Christopher created the podcast because those who read the book wanted to participate in category designs
- [16:12] – Christopher also wanted to make a difference for entrepreneurs and help them succeed
- [17:19] – JLD says building your own swiss army knife of skills will protect you and help you survive
- [17:51] – The Lightning Round
- What was holding you back from becoming an entrepreneur? – “Everything in my life – I had no experience, no money, no relationships, no education”
- What’s the best piece of advice you’ve ever received? – “F them” Christopher says entrepreneurs are warriors and the products and services that people love now are there because entrepreneurs and innovators did everything they could to make it thrive
- What’s a personal habit that contributes to your success? – “The more we shut up the more we learn”
- Share an internet resource, like Evernote, with Fire Nation – Zoom
- [21:33] – Eric of Zoom is the classic entrepreneur story of coming to America from China and becoming a founder of a company
- [22:27] – Connect with Christopher on his website, Legends and Losers
- [22:34] – Design your category and then you get to dominate it
Christopher: I absolutely am ready to light myself and everybody else –
Christopher: On fire, Dominic.
John: Christopher is the coauthor of Play Bigger: How Pirates, Dreams, and Innovators Create and Dominate Markets. And he’s a cohost of the Legends and Losers podcast. He is a former three-time public company CMO and entrepreneur. Christopher, take a minute, fill in some gaps from that in show, and give us a little glimpse of your personal life.
Christopher: Well first of all, John. Thanks of course for having me, big fan of the show.
Christopher: And I’m someone who got thrown out of school at 18 for being stupid. I found out at 21 that I’m dyslexic. And so, the alternatives I had in life were work a manual labor job. I was an orderly at a hospital. So, I could either shave old guys’ you know whats for a living or I could start a company. And so, with my friend Jack, I decided to start a company. And today I’m a retired CMO living in beautiful Santa Cruz, California. And I surf a lot, and I’m married to an extraordinary woman, and I live with an amazing tribe of people. And most days, I feel like this must be happy.
John: Love all of that and we’re going to take you to sometimes in your journey Christopher that you didn’t quite think was heaven, but before we get there, I want you to break down for fire nation what you consider your area of expertise. What is that?
Christopher: Probably my biggest area of expertise, John is I am what you could a category designer.
Christopher: Yes. So, it turns that most people when they think about marketing, they make an unconscious choice to participate in an existing market that was designed either purposely or accidentally by somebody else. So, there are rules in every market. And a market or a category is really a way of thinking about a problem and a solution. And so, most entrepreneurs when they go to launch their company, or their product, or a new version of their product, or service they make an unconscious choice to compete in an existing space or category.
And what I’ve learned over 30 years and we did three quarters of a million dollars in research for our book Play Bigger, is that Legends actually teach the market or the category to think about a problem and a solution in a particular way. And as a result, John, they set up the rules of a whole new category. And so, I’ve spent the last 30 years of my life trying to train myself how to design new categories.
John: Fire nation, we’re going to be getting deeper into this because I have some deep seeded beliefs right along these lines as well, but real quick Christopher, what do you want to make sure our listeners get from your area of expertise? What’s that one thing that we probably don’t know, but should know as entrepreneurs?
Christopher: Here’s the one that I hope makes the biggest difference and certainly will help increase the odds for entrepreneurs. So, when you talk to entrepreneurs or any kind of innovator, John, at least in my experience what I found is they essentially pull two big levers. One is product/service. They think that if they build a legendary carbondingulator and a legendary company to deliver the carbondingulator to the world everything works. And whatever challenge comes up or opportunity for that matter they, “Oh, great. More product, more features!” Or, “Expand our geography. More sales people, more feet on the street, product, product, product, company, company, company.”
And here’s what we know, the legends pull a third lever. And that lever is called category. They design a new product, company, and category. And they position themselves as distinct. And if they get all three right, we call it prosecute the magic triangle – product, company, and category. You get to be Pablo Picasso, or Mark Zuckerberg, or Sarah Blakely.
John: One thing I want to talk about right now because you, Christopher, have created your version of heaven which is amazing and that’s kind of what we’re all striving for fire nation to live in what we consider our own version of heaven. But you’re always there. You’ve had the ups, you’ve had the downs, and I want you to take us to what you consider your worst entrepreneurial moment to date. So, Christopher, don’t pull any punches bother, take us there, tell us that story.
Christopher: Yeah, well John, one of the reasons that we called our shows Legends and Losers is cause we really believe you can’t be a legend without being a loser. And so –
John: Every master was a disaster.
Christopher: I love that. And so, there’s been a tremendous amount of – if you’ll allow the word losery – in my life. And probably the worst one was I started at 18 with no options, and that’s why I became an entrepreneur. I didn’t even know the word entrepreneur. And by 21, that first company had failed. And so, at the time there was a recession, and I was having a really hard time getting a job, I was newly married. And so, there I was 21 years old, a failed entrepreneur, in debt up to my eyeballs, and I really was completely at a loss for what to do with my life.
John: What’d from that point? I mean you’re kind of on the floor there, you’re kind of grasping at straws, nothing’s really working. What happens when you hit the bottom, when you’re just scraping the rock pile?
Christopher: Well first of all, I’m scared is as S –
John: It’s all bejeesus we say.
Christopher: As all but something, yeah. And so, I’m terrified. I feel like a failure and even worse than that, my good lucks are not such that I can go to the grocery store, and smile, and they give me a bag of food. And so –
John: I’m lucky you’re skype phoning. You’re a pretty good-looking guy for having no hair on your head.
Christopher: Well, thank you. I appreciate it, John. But it wasn’t enough for the folks down at the grocery store, I’ll tell you that. And so, I like a lot of young people who are lost had to get a job. But luckily, I learned early on, John, that our relationships matter and I tried to build great relationships. And one of the companies that I had – to create a partnership with in my first business – was another entrepreneur, and he was starting a new company, and he asked me to join as the head of sales of that company. And within a year, I was able to help start that company and – believe it or not – pay off my debt, and move forward in my life, and career.
John: I want to hone in on that word, fire nation. Relationships. People ask me all the time, “John, you’ve done now over 1,700 episodes, what’s the biggest thing that you think has contributed to your personal success of growing EO fire into a seven figure a year business?” It’s just one word, it’s relationships. And I did not know that when I started. I didn’t know that the guests that were going to be on show, that were going to comprise the – now over 1,700 alumni – were going to be the reason that I’ve had as much as success as I have today because I was clueless. I was naïve, I was inexperienced, I was flat out stupid in some areas.
But I learned, I listened, I educated myself, I learned from every single guest. And I built those relationships. Relationships matter. And that’s what Chris did was well. He relied on relationships to build from nothing, to what he is today. And he’ll never forget that listen, I’ll never forget that lesson. And Chris, I might have stolen a little bit of your thunder there cause that’s exactly what you said, but I want you to pick out one other thing that you want to make sure that fire nation really gets – from a lesson that you learned from that worst moment – so, tell us that.
Christopher: You call it, John, the, “Ah ha,” moment and the big, “Ah ha,” moment for me really in my working life is – it could be summed up with the expression, position yourself or be positioned. And so, Mohammed Ali famously said, “If I don’t tell them I’m the greatest in the world, how are they going to know, right?” And so even though I was a failed entrepreneur, with no education, no money, very few relationships at the time, and certainly no experience. I did have a belief in myself. I did grow up in a family that was incredibly supportive and backed me from the beginning. And so, I was able to muster that sort of courage and – to your point on relationships – somehow and I didn’t know it.
I wasn’t out networking, you know what I mean? I was just trying to build my frickin’ business, trying to do something with my life, and this guy – his name was Bill Walker – I guess took a shine to me. He was an older entrepreneur, a more successful entrepreneur, and I called him to tell him we had failed. And he said, “Well, what are you doing?” And I said, “I don’t know.” And he said, “Well, I’m about to go on vacation, can you wait a week, cause I’m starting a new company and I’d love you to come help me.” And so, one of the things I hear a lot today, John, is, “You should go out, and build relationships, and you should network, and you should do this stuff.”
And I think it’s a bit of a fallacy in that we want to go out and build relationships, but not for the sake of building relationships if you know what I mean. I had built a relationship with this guy – Bill Walker – by doing business, by really trying to add value to his business, and hopefully he was trying to do the same. And so, when he saw I was available, I think what he saw was a young, determined, driven, young man who’d been knocked down. And he gave me that hand to pick me up, but I don’t want anybody to think that I was out there hanging out at parties just handing out business cards, hoping somebody would discover me. I was out there hustling.
John: Position yourself or be positioned. Fire nation, lovely words, great take away. And Chris, let’s be frank, that was your greatest, “Ah ha,” moment to date of your life. I mean that’s what you just shared, but you’ve had a lot of great ideas. A lot of, “Ah ha,’ moments. And what I want you to do now, is to take us to one of those great ideas. One of the greatest. Take us to that moment, kind of tell us that story of how that, “Ah ha,” moment developed and how you turned it into success.
Christopher: So, I was a young entrepreneur working on my second startup living in Toronto, Canada. I grew up in Montreal and I was in the technology industry, John. And I saw the very early days of – what at the time was called Sales Force Automation – and I was very excited about it because I love sales, and marketing, and I love technology. And I was a young guy in my 20s and I kind of had this spider sense – if you will – that there was this new category developing that what became CRM. Customer Relationship Management was taking off at the time and it was very nascent.
And I thought, “You know what, self? If you were smart and you were you, you would be on the front end of this massive new category.” And in addition to that I said – you know what, John – “I’m going to be the pied piper that leads this parade. I’m going to be one of the guys that’s on the front end of this whole new exciting area.” And I sort of declared myself a thought leader in Customer Relationship Management. And I went out, and I did a lot of speaking, and writing, and so forth. And I positioned my small boutique consultancy at the time as the leader in a new category of technology.
And that was my first real experience understanding that you can design a category, you could really teach the world, and therefore a market – to think about a problem and a solution in a particular way. And if you did that successfully and you used what you could think of as a point of view to position yourself as the head of this new category – that was a way to catapult yourself forward in a very powerful domain as opposed to trying to be the 437th dentist in my town.
John: Fire nation there is always a massive new category that’s around the corner. I mean the world we live in is happening all the time. So, you had that opportunity to be that first mover. You had that opportunity to be that pied piper, but what do you need to do? You need to have patience, number one. You can’t jump on every new opportunity because even though it might a good one, it might not be for you. For instance, like writing a blog back in 2006 – although it would have been a great opportunity for me – I wasn’t a writer. I was never going to be able to do that. So, I passed on those type of things.
I had patience, but keep your finger on the pulse and if it’s the right category, if it’s the right thing, if it’s the right opportunity then you pounce. And then, you become that first mover and you had that first mover’s advantage that I experienced with podcasting. And so, that momentum builds up with you and you be that pied piper. You create that category, and you really hold that flag, and you have people march to your beat, instead you of you marching to everybody else’s beat. So –
Christopher: The other thing, John – and I hate to interrupt you – but I just – how many opportunities do I have to have this conversation with you. You actually are an intuitive category designer. And so, one of the things we found in the work of Play Bigger is category designers who are intuitive about it teach the world to think about a product, a company, and a category in a whole new way. And so, everything you did with Entrepreneur on Fire – not only were you early in podcasting which can make a difference – but it turns out when you unpack it, John, it’s not just being early. Facebook was two or three years later than most of the, “Early social networks.”
You got the magic triangle right – product, company, and category. Your product – the podcast – was a unique design in a lot of ways, we could unpack that. And you positioned it very – and I’m going to use this word on purpose, John – differently. And so, by being different – not better – people could understand what category your podcast was. It was like, “Oh, this guy’s really different, it’s every day, it’s always entrepreneurs,” and all the other things about your format and your approach. And so, you created a category of podcast which you could dominate. And so, the way I think about what you did is if you want to get nouveau riche you got to define your niche. And that’s exactly what you did.
John: Product, company, category. Fire nation think about those three things. How are you incorporating that into your business and into your life? And Chris, for real brother, if you’re going to be dropping value bombs like that, interrupt away my man. You’re the guest on this show, you’re the spotlight. Let’s talk about right now you think the number thing is that you are most fired up about today.
Christopher: Well in my life, the new thing I’m most fired up about is my podcast Legends and Losers cause I don’t have to tell you, John, you get to have incredible conversations with incredible people. And so, it’s really – it’s funny I’ve been – Legends and Losers is about three months old and I can’t imagine not having it in my life.
Christopher: But the reason for it is – so, our book Play Bigger came out in June of 2016. And as it was coming out, John, I read an article in the Wall Street Journal that knocked me on my behind. And the headline of the story said The Crisis in American Entrepreneurship. And as I read the story – and you can see it, it’s online – they quote a bunch of MIT and Brooklyn’s Institute of Research and the net of it is more countries in the United States die every week then are founded. And the millennials are on track to be the least entrepreneurial generation in history. And I’m someone for whom – John, entrepreneurship was a way out – not a way up.
I couldn’t go to school; there was no school for me at the time. They threw me out, I’m dyslexic, I didn’t fit. And for those of us – I think there are some people in the world, John, who they can find their place in the world and God bless them if you can find your place in the world. And then, there are those of us who grew up on the island of misfit toys and we have to make our place in the world. And so, my point is a big part of why I started Legends and Losers, was people who read Play Bigger wanted to participate in more dialogue around category design and some of the things that we’re talking about today.
But in addition to that, John – this may sound corny – but I wanted to dedicate the back half of my life to trying to make a difference for entrepreneurs, and to park entrepreneurship, and entrepreneurial success because it – for me – entrepreneurship out of a life of struggle. It wasn’t like, “Oh, well I was going to Harvard. And if this doesn’t work out, I’ll just a get a job at Google.” That’s not what was happening for me.
John: Yeah and fire nation, I mean we think that the top of the top, the elites like with Google – I mean fire nation, .02 percent is the acceptance rate into Google right now. So, even people that think they are on that elite path, I mean they’re in for a hard road. So, why not have that swiss army knife like approach of an entrepreneur where you have all the skills. So, no matter what industry, what sector, what niche crashes, or even if the whole economy comes down – guess what?
You know how to make it happen. I don’t want to compare entrepreneurs to cockroaches, but I mean the reality is cockroaches survive when the catastrophes happen and entrepreneurs do as well. We might not be thriving as much as we do in the good times, but we have that skill set to keep driving forward, fire nation. So, build that skill set up. It will protect you in times to come. And if you think that Chris has been dropping value bombs so far, just wait for the lightning round after we get back from thanking our sponsors. Chris, are you ready to rock the lightning rounds?
Christopher: I’m ready to turn the Marshall stacks into Les Pauls up to 11. How’s that, John?
John: Love it. What was holding you back from beginning an entrepreneur.
Christopher: Well, I mean I had no experience. I was 18, right? No experience, no money, no relationships, of course no education. And so, as I said I didn’t really even know the word. The joke I had heard once I did hear the word was entrepreneur was a fancy word for unemployed.
John: What is the best advice that you’ve ever received?
Christopher: Well, I want to stay PG on my language, so I’ll just share it this way. F them. And what I mean by that is I’m an old school punk rocker and I think entrepreneurs are warriors. And people – listen, every legendary product or service that we love exists because an amazing entrepreneur or innovator was absolutely unwilling to let their innovation anything other than thrive. And they got product, company, and category right. And they created something new that opened up the world up to something amazing.
And in order to do that, you have to be willing to – if you will – hack the future that you want and there’s going to be a lot of people who tell us that we can’t have that future. I was told that I had to get an MBA, stop swearing, and learn to play golf. And I said, “F it,” to all of those things and I just went forward with my life and my career.
John: You only have to stop swearing during the 20 minutes you’re on EO fire. So, thank you for that Christopher because we have a lot –
Christopher: I’m trying.
John: Of parents who are driving right now trying to expose their kids to the wonderful world of entrepreneurship. So, tell those kiddos out there thanks for listening and to all the parents yes, we will be keeping EO fire PG. So, Christopher, what’s a personal habit that contributes to your success?
Christopher: Shut up, shut up, shut up. The more we shut up, the more we learn. Those of us in sales, the more we shut up, the more they buy. And I got taught early, John, that very rarely does somebody ever say to us, “Hey, John. Thanks for talking.”
John: I love that one, Chris. I’m going to use it twice and give you credit. And then every time after that, it’s mine. So, that’s just how it goes.
Christopher: It’s yours.
John: But fire nation there’s a reason why we have two ears and one mouth. So, just recognize that. And can you share an internet resource like Evernote with fire nation?
Christopher: Yeah, my favorite internet resource is Zoom. And Zoom is a six-year-old company that has created a magical cloud web based communications technology for conference calling. And I think it’s – imagine if Skype and WebEx had a legendary baby – it would be Zoom. And I’m happy to say we just had Eric Yuan, the founder of Zoom, who is a billion dollar – what’s called a unicorn company here in Silicon Valley. We just had him on Legends and Losers and he’s an amazing guy. But we shoot our shows on Zoom. I also don’t really want to travel very much, John. I used to travel two to three –
Christopher: Hundred thousand miles a year. And so, I do most of my meetings as Zoom, they’re incredible, and I love them, and I have no financial interest in the company. I just think they’re awesome and I wish Eric and his team incredible luck in transforming the way we all communicate.
John: Yeah. As do I by the way. If I was doing anything that had to with video for the podcast – if it was a video podcast, it would be on Zoom.us all day long. And whenever anybody asked me, “Hey, John, how should I shoot my podcast?” I’d say, “Zoom.us make it happen.”
Christopher: Oh, can I interrupt –
John: Yeah, go ahead.
Christopher: You with a quick story about Eric?
Christopher: He’s the classic entrepreneur story, right? The internet starts to take off, he’s an engineer living in China. He says, “I want to be part of this thing. I’ve got to get to the US.” Turns out he has a buddy who’s building WebEx and he gets a job – I think he was number 12 at WebEx as an engineer.
Christopher: And he just builds himself up and now he’s the founder of Zoom. And Zoom is a company that is growing somewhere between two and three hundred percent a year. They just raised $100,000,000 from Sequoia Capital and they’re worth over a billion dollars. And so, he’s the classic entrepreneur story that we all love. I come to America with very little and now he’s literally running one of the fastest growing companies in Silicon Valley.
John: And as long as he doesn’t let all that equity money ruin the company, then he’ll be on a good path for sure.
John: Christopher, let’s end today on fire with a parting piece of guidance, the best way we can connect with you, and then we’ll say goodbye.
Christopher: Best way to find me is legendsandlosers.com.
John: And a parting piece of guidance.
Christopher: Design your category and then you get to dominate it.
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