
Carving Your Unique Future with Christopher Lochhead
09/28/23 • 35 min
For some lucky souls, the universe lays out a space for them, a place where they can fit into society. There are, however, others who do not conform to the traditional spaces and roles. They are square pegs in a round hole world. How can these individuals defy the conventional narrative and resist the constraints of societal norms?
In this episode of the Knucklehead podcast, Stephen talks with Christopher Lochhead. A dyslexic paperboy from Montreal who got thrown out of school at 18, Christopher talks about how he created his own place in this world. With few other options, he became an entrepreneur, then three-time Silicon Valley public company CMO (Mercury Interactive, Scient, Vantive), and an investor/advisor to over 50 venture-backed startups.
Also best known as a "godfather" of Category Design, Christopher shares how he developed his content distribution strategy, why today is the greatest time in the history of human beings to be a creator and an entrepreneur, and how success is about failing in the right direction.
Christopher is a 14-time #1 bestselling Amazon author, #1 charting Apple business podcaster, top 5 business newsletter creator, and former 3X public tech company CMO. He co-authored the first two books on the management discipline Category Design, Play Bigger, and Niche Down. He also co-creates mini-books on Category Design, Category Pirates, and the Category Pirates Series of Amazon books. Recently, he co-authored #1 bestsellers "The 22 Laws of Category Design" and "Snow Leopard: How Legendary Writers Create A Category Of One".
Enjoy!
In This Episode
01:30 - Christopher's strategy for delivering content.
05:10 - How Christopher developed his content distribution strategy.
11:17 - Knowledge workers versus creator capitalists.
15:22 - Christopher's newest category.
20:02 - One of the biggest fallacies in marketing.
22:14 - How Christopher's screw-ups led him to where he is today.
28:55 - What The 22 Laws of Category Design is all about.
33:22 - Christopher's final piece of advice.
Favorite Quotes
00:00 - "I'm in giant intergalactic failure in every dimension. I don't even have a GED. I got thrown out of school at 18. I found out at 21 that I have five different learning differences — dyslexia, dyscalculia, ADHD, and a couple of others. And so at 18 years old, with very few choices because nobody would hire me to do anything, I started a company." - Christopher Lochhead
06:07 - "We're living in a new native digital world. Nobody really knows how to pioneer this world. And so we think that what's there to do is to go and play." - Christopher Lochhead
12:23 - "As the availability of all of humanity's knowledge becomes accessible and closer and closer to free over time, people who get paid to apply existing knowledge are gonna become less and less." - Christopher Lochhead
23:06 - "There are people for whom there is a place in this world. And there are some of us for whom there is no place, and we do not fit. And so rather than find a place, I have to make my place." - Christopher Lochhead
24:07 - "For me, entrepreneurship was not a way up in the world as much as it was a way out of a life of struggle and poverty." - Christopher Lochhead
26:09 - "If you experiment and create and push and pull and fail, lose a ton of money and get laughed at and be incredibly shamed and embarrassed by things and et cetera, that's innovation. Success is about failing in the right direction." - Christopher Lochhead
31:38 - "If you view yourself as a person/company that is trying to catalyze a movement and bring people together and drive a conversation, magic happens." - Christopher Lochhead
33:25 - "This is the greatest time of technological innovation in the history of human beings. And it is the greatest time in the history of human beings to be a creator and an entrepreneur." - Christopher Lochhead
33:53 - "The future needs the entrepreneurs, the creators, the innovators, the pirates, and dreamers to do exponential things to create different futures. And there's never been a greater time to create different futures and category design your own new markets than right now." - Christopher Lochhead
Connect with Christopher Lochhead
Connect with Knucklehead Media Group
- Website...
For some lucky souls, the universe lays out a space for them, a place where they can fit into society. There are, however, others who do not conform to the traditional spaces and roles. They are square pegs in a round hole world. How can these individuals defy the conventional narrative and resist the constraints of societal norms?
In this episode of the Knucklehead podcast, Stephen talks with Christopher Lochhead. A dyslexic paperboy from Montreal who got thrown out of school at 18, Christopher talks about how he created his own place in this world. With few other options, he became an entrepreneur, then three-time Silicon Valley public company CMO (Mercury Interactive, Scient, Vantive), and an investor/advisor to over 50 venture-backed startups.
Also best known as a "godfather" of Category Design, Christopher shares how he developed his content distribution strategy, why today is the greatest time in the history of human beings to be a creator and an entrepreneur, and how success is about failing in the right direction.
Christopher is a 14-time #1 bestselling Amazon author, #1 charting Apple business podcaster, top 5 business newsletter creator, and former 3X public tech company CMO. He co-authored the first two books on the management discipline Category Design, Play Bigger, and Niche Down. He also co-creates mini-books on Category Design, Category Pirates, and the Category Pirates Series of Amazon books. Recently, he co-authored #1 bestsellers "The 22 Laws of Category Design" and "Snow Leopard: How Legendary Writers Create A Category Of One".
Enjoy!
In This Episode
01:30 - Christopher's strategy for delivering content.
05:10 - How Christopher developed his content distribution strategy.
11:17 - Knowledge workers versus creator capitalists.
15:22 - Christopher's newest category.
20:02 - One of the biggest fallacies in marketing.
22:14 - How Christopher's screw-ups led him to where he is today.
28:55 - What The 22 Laws of Category Design is all about.
33:22 - Christopher's final piece of advice.
Favorite Quotes
00:00 - "I'm in giant intergalactic failure in every dimension. I don't even have a GED. I got thrown out of school at 18. I found out at 21 that I have five different learning differences — dyslexia, dyscalculia, ADHD, and a couple of others. And so at 18 years old, with very few choices because nobody would hire me to do anything, I started a company." - Christopher Lochhead
06:07 - "We're living in a new native digital world. Nobody really knows how to pioneer this world. And so we think that what's there to do is to go and play." - Christopher Lochhead
12:23 - "As the availability of all of humanity's knowledge becomes accessible and closer and closer to free over time, people who get paid to apply existing knowledge are gonna become less and less." - Christopher Lochhead
23:06 - "There are people for whom there is a place in this world. And there are some of us for whom there is no place, and we do not fit. And so rather than find a place, I have to make my place." - Christopher Lochhead
24:07 - "For me, entrepreneurship was not a way up in the world as much as it was a way out of a life of struggle and poverty." - Christopher Lochhead
26:09 - "If you experiment and create and push and pull and fail, lose a ton of money and get laughed at and be incredibly shamed and embarrassed by things and et cetera, that's innovation. Success is about failing in the right direction." - Christopher Lochhead
31:38 - "If you view yourself as a person/company that is trying to catalyze a movement and bring people together and drive a conversation, magic happens." - Christopher Lochhead
33:25 - "This is the greatest time of technological innovation in the history of human beings. And it is the greatest time in the history of human beings to be a creator and an entrepreneur." - Christopher Lochhead
33:53 - "The future needs the entrepreneurs, the creators, the innovators, the pirates, and dreamers to do exponential things to create different futures. And there's never been a greater time to create different futures and category design your own new markets than right now." - Christopher Lochhead
Connect with Christopher Lochhead
Connect with Knucklehead Media Group
- Website...
Previous Episode

Selling More Deals with Adam Boyd
Selling is essential for all business owners and salespeople, but knowing how to do it effectively can be challenging. Despite having a great product or service, sellers may need help to close deals and generate revenue. While each business is unique, and each salesperson has their own strengths and weaknesses, how can business owners and sellers sell more effectively and achieve greater success in their business?
In this edition of the Knucklehead Podcast, Stephen talks with Adam Boyd, Principal at The Northwood Group. A former high school English teacher and football coach, Adam talks about the parallels between football and real-world business, the screw-ups he made in his sales career, and how he now helps owners and sellers expand their businesses.
Adam Boyd is the Principal at The Northwood Group, a consulting firm that delivers best practices for sales teams and professional services firms to win more business. Adam has over 15 years of working with small to mid-sized businesses on sales growth. His expertise is deep in direct selling, sales management, and lead generation. Adam has consulted in over 20 industries, had an exit, worked in turnarounds, started a business from the ground floor, and had his share of failures. He's cold-called, sold to CEOs, built and managed campaigns, and led teams to set records. Adam began his career as a high school English teacher and football coach.
Enjoy!
In This Episode
03:25 - Backstory of Adam Boyd
06:46 - The most common mistake people make when it comes to learning
08:49 - The parallels between football and real-world business
14:51 - Some of the screw-ups Adam made in his sales career
21:20 - Adam's approach to working with business organizations
25:01 - How Adam can help business owners and sellers expand their businesses
Favorite Quotes
03:46 - "People from a coaching standpoint needed repetition and a lot of feedback to see what they were doing." - Adam Boyd
15:25 - "For anybody who has to sell and work on the phone, they've got the risk of rejection. There has to be a deep desire to get where they're trying to go, or else it's just hell." - Adam Boyd
19:48 - "One of the things that I've done poorly in my life is not making sure people are committed to doing what it takes to get where they want to go." - Adam Boyd
22:16 - "Anything in our life that's done well takes a little bit of time." - Adam Boyd
27:11 - "We all talk about how failure's a great teacher, but it's painful when you're going through it." - Adam Boyd
Connect with Adam Boyd
- The North Wood Group
- Grab your COVID-19 survivor T-shirt HERE
Connect with Knucklehead Media Group
• Knucklehead Media Group is your "push button" for podcasts. We help companies and organizations tell their story using podcasts and best practices for content distribution. Home to some of the top podcasts across multiple categories, captivating coursework on gaining traction with your show, and consulting to those companies BOLD enough to get some wins. We believe your mistakes set the foundation for your success, those stories help customers beat a pathway to your doorstep, and the myths from bringing business online shouldn't hold you back from getting yours.
Click here for more episodes of the Knucklehead Podcast
Next Episode

Bridging the Gap Between Military and Healthcare
The Knucklehead Podcast and MEDEVAC Podcast join forces in this episode to discuss the value of networks and communities. Our hosts, Stephen Colon, Christian Meyers, and David Reid, share their personal experiences in the military and the importance of valuing one's own story of struggle and recovery. They emphasize the power of resilience and the need to take risks and challenge oneself to grow and succeed.
With a mission to share stories of service, injury, recovery, resiliency, failure, and success, David and Christian touch on the connection between health struggles and the military and how war impacts medical advancements. In the final segment, they speak about the Texas Valor Project and how they fight traumatic brain injuries.
David served in the US Army, while Christian served in the Air Force. They both have firsthand experience with combat and the challenges that come with it. Through their podcast, they aim to share stories of resilience and recovery, focusing on the experiences of injured veterans and the medical personnel who rescue and care for them.
Enjoy!
In This Episode
03:18 - The value of networking and connecting with others.
05:58 - How podcasts relate to the Oregon Trail story.
07:51 - The unique aspects of the military.
08:59 - How Knucklehead Podcast was born.
15:19 - The connection between the military and medical fields.
17:12 - A commonality between military and civilian adversity.
19:31 - How David and Christian value one's own story.
24:38 - What the Texas Valor Project (TVP) is about.
27:38 - How the transcranial magnetic stimulation helps with major brain functions.
33:39 - How nonprofit organizations bridge the gap in healthcare.
36:32 - The importance of vetting business partners and being true to oneself.
40:52 - How Stephen's screw-ups and mistakes led to his present success.
42:49 - David's advice to people who have been injured.
Favorite Quotes
08:04 - "Being in the military exposes you to a multitude of different worlds. And it unplugs you from the system you're in. It helps cultivate this environment of thinking outside the box." - David Reid
14:10 - "The problem that a lot of people face is that they're just in this community of being and feeling safe, so they never push themselves or challenge themselves. And that's what the military drives to. The military instills that resilience in you and that ability to push forward." - David Reid
15:30 - "Every major medical advancement of the last hundred years has been explicitly due to war. So every medical advancement, with plastic surgery, traumatic brain injuries, PTSD, and everything starting from World War I until the present day, was directly because of conflict." - Christian Meyers
16:27 - "Conflict creates the opportunity for breakthroughs." - Stephen Colon
17:40 - "Everybody faces their own battles. It doesn't matter if you're hit in war or you're crossing a street, and you see your best friend get hit. Post-traumatic stress is the same response physiologically across the board." - David Reid
43:27 - "If you're not getting failure, then you're not challenging yourself hard enough. You're not pushing yourself hard enough." - David Reid
43:35 - "Even the adversity that you're facing in this current moment is going to bring out the best version in yourself if you make the right choices along the way." - David Reid
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