Posts Tagged ‘Marketing/Category Design’

232: Brett Hurt Serial Entrepreneurial Success

Brett Hurt Serial Entrepreneurial Success Legends and Losers

How does coding for fun lead to becoming a category king? On today’s episode, Brett Hurt joins Christopher Lochhead in a riveting discussion about his story of serial entrepreneurship, the future of data, and the power of community.

“There’s just this serendipity that occurred in life where these things really drew me.” – Brett Hurt on how entrepreneurship pulled him in

Three Things We Learned

Wired to do big things

Brett has always had the knack for creating things that spelled massive success from when he was young. His parents had taught him to slow down when he finally becomes successful the way he defines it. For a time he tried out his parents’ lifestyle, but entrepreneurship has always pulled him in.

A figure to emulate

He took a three-year break from being the head of his company to be more hands-on as a father to his children. It surprised him when his ten-year-old daughter walked up to him one day to ask when he was going to start another business. He realized he was most inspirational to his daughter when he was working and not being on every field trip, and his children became’s first investors and are very proud of chipping in their toy money when they did.

Serendipity of success

He got into his first big success as an entrepreneur when he started an e-commerce site with his wife on a whim. He was feeling bored one day so he began coding an e-commerce package that he and his wife utilized for an online store. There weren’t many people online back then, but a community eventually built around it.

The serendipity of building the e-commerce site directly led to the first category that he entered into, which is e-commerce analytics. Hence the birth of Coremetrics, rated the #1 Web analytics solution some years later.


Brett is the CEO and co-founder of It is a Public Benefit Corporation (and Certified B Corporation) focused on building the platform for modern data teamwork. helps you tap into more of your company’s collective brainpower—everyone from data scientists to nontechnical experts—so you can achieve anything with data, faster.

Brett is also the co-owner of Hurt Family Investments (HFI), alongside his wife, Debra. HFI are involved in 59 startups and counting, mostly based in Austin (see for details).

HFI are also invested in 15 VC funds and multiple philanthropic endeavors.

Brett founded and led Bazaarvoice as CEO from 2005-2012, through its IPO, follow-on offering, and two acquisitions (PowerReviews and Longboard Media).

Prior to Bazaarvoice, Brett founded and led Coremetrics. Forrester Research rated Coremetrics #1 Web analytics solution and, like Bazaarvoice, it expanded into a global company and category leader. IBM acquired Coremetrics in 2010 for around $300m.






We hope you enjoyed Brett Hurt 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!

231: Questions and Cocktails First Marketing Hire

Questions and Cocktails First Marketing Hire Legends and Losers

On another episode of Questions and Cocktails, Christopher Lochhead responds to a question by an aspiring category king. What does a good first marketing hire look like? Do you choose potential over experience?

“I think legendary CEOs are evangelists and they don’t outsource the strategic part of marketing.” – Christopher Lochhead

Working on Lightning Strikes

Josh Goodman is grinding to build his nine-person company to a new height. They have doubled in revenue for the last three years in a row. However, their marketing department has little to nothing besides SEO and social targeting advertising.

He has advertised for a Marketing Manager on LinkedIn and has gotten a lot of responses. With his venture for a first marketing hire, he wants to hear thoughts on whether to hire a 25-year-old or someone who’s hardcore in the trenches of marketing.

Hiring Right for a Small Business

It can often be tempting to hire a youngster with tons of potential and still has a lot of room for growth. The company can sell them on what they do in the business in order to help the new hire crush it in the role they will take.

On the other hand, there is the option to hire someone that has had their experience with email campaigns and content marketing. These people are all about creating a brand and helping manage and build assets.

Outsourcing the Strategy

For a small entrepreneurial company, the CEO also needs to take up the role of the CMO. A C-level executive sounds like a good idea, but it is far more beneficial for a CEO to act as the category designer and evangelist of a brand, especially at an early stage of the game.

Even when a company has gotten bigger, the E in CEO should still stand for “evangelist”. Prominent examples include Steve Jobs of Apple and Larry Ellison of Oracle.

To hear more from Christopher, download and listen to the episode!

We hope you enjoyed Questions and Cocktails First Marketing Hire! Christopher loves hearing from his listeners. Feel free to email him, connect on FacebookTwitter, Instagram and subscribe on iTunes!

228: Cannabis Category King Dennis O’Malley, CEO of Caliva

Cannabis Category King Dennis O'Malley, CEO of Caliva Legends and Losers

How does a button-down professional become a legendary pot entrepreneur? On today’s episode, Dennis O’Malley shares with us how he embraced his category. And he also talks about why taking on the pot industry is an exciting endeavor as any.

“In cannabis, almost more than any other industry, there’s an ability to really create and own your category.” – Dennis O’Malley

Three Things We Learned

Dropping the bomb to everyone

Dennis started out like any other aspiring entrepreneur—a button-down, suited up professional who didn’t look the part of a pothead. He remembered the last time he ever smoked back in freshman year, and even then he thought it was mowed lawn grass. Naturally, people’s reactions varied when he dropped the news of wanting to be part of the industry.

Earnest involvement in the company

He had no cannabis acumen or passion for the product, not even an understanding of the industry. But Dennis developed a great relationship with the owner of the company and began consulting for the business from there. Through all this, he realized how challenged the company believed it was and the impact cannabis could have to everybody’s well-being.

Challenging himself as a leader

When Dennis took the lead, he gave himself six months to do two things for the company. He tried to find out if he could recruit the people that he needed to be able to be successful. Tied together with the passion around the industry that he discovered, he thought he could be the doing things right.

He became the CEO of Caliva back in January 2017. And he finds himself continuously blown away by the number of people that he gets to meet as well as the passion that he learned about. Dennis can now confidently say that he has really endeared himself to the industry.


Dennis O’Malley is the CEO and President of Caliva. It is the largest vertically integrated company based in the State of California.





We hope you enjoyed Dennis O’Malley 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!

227: Questions and Cocktails Content Creator/Thought Leader

Questions and Cocktails Content Creator Thought Leader Legends and Losers

On this episode of Questions and Cocktails, Christopher Lochhead answers another question from one of his listeners. How does one go about becoming a great content creator and thought leader?

“A lot of the most interesting people have a unique and differentiated point of view and they kind of come from that point of view on a regular basis.” – Christopher Lochhead

Think About the How

Before you start creating your content, you might want to think about how you would want to do it. Distribution and form matter a lot, whether you choose to do a blog, book, or podcast. You might also want to become a Twitter thought leader.

Ever since he started his own podcast, Christopher has learned that he can also turn a great episode into a blog. Niche Down, in fact, made use of a lot of examples that originated from great podcast conversations. There are so many ways to express great content, primary or secondary.

What is Different About You?

The world doesn’t need anymore bull. No one needs a blog post from you about following your passion or any other topic that has been done so many times already.

When starting out as a content creator and thought leader, the first thing that you must think about is what’s different about you. Once identified, you must lean on that different.

Develop Your POV

What problem do you solve and why does that problem matter? In solving this problem, you must also have a point of view that is interesting, provocative and differentiated. While he puts out a lot of things, Christopher’s content has recurring themes, and this is because he has a point of view centered around entrepreneurship, category design and life design.

Make no mistake. As a content creator and thought leader, you can go from one topic to another. But having that perspective that you work with regularly will help you stay grounded and be truly different.

To hear more advice from Christopher, download and listen to the episode!

We hope you enjoyed Questions and Cocktails Content Creator/Thought Leader! Christopher loves hearing from his listeners. Feel free to email him, connect on FacebookTwitter, Instagram and subscribe on iTunes!

214: Niche Down Q&A with Praxis Students Pt. 2

Niche Down Q&A With Praxis Students Pt. 2 Legends and Losers

On Episode 211, Christopher Lochhead got on with Praxis students for an up close and personal Q&A session. Today, the second part of this conversation continues, teeming with business stories and learnings that ultimately culminated in realizing the importance of niching down.

“Nobody makes it alone. Other people make you successful.” – Christopher Lochhead to Praxis students

Three Things We Learned

‘Extraordinary’ isn’t for everyone

Most people want to become legends in their own right, and some of them equate this to being extraordinary. The thing is, some people don’t necessarily want to be extraordinary as long as their business is profitable. The pitfall of this line of thinking, however, is that category violence happens all the time and so paying attention to everything is a must.

Cultivating relationships is key to success

It has been an ongoing experience in Christopher’s life how much other people make him successful. In a community where everyone strives to differentiate themselves through the careers they want to launch, finding someone to resonate with is a blessing. This results in a collective spirit of wanting your contemporaries to do extremely well alongside you.

To extend a hand is powerful

You don’t have to help everybody within a five-foot radius of you. But it’s always a powerful thing to extend a hand to somebody else. When we go out of our way to contribute our strengths that are someone else’s weaknesses, we create something powerful.

Christopher gets asked around a lot why he’s friends with so many CEOs. The truth of the matter is that when he first met them, they weren’t the successful people that they are now, but people who were on the verge with him. With the inspiration brought by his peers, he was able to rise up and take his game up several notches to become his present self.


Discover Praxis

Amazon – Niche Down

Amazon – Play Bigger

We hope you enjoyed this second installment of Legends and Losers Q&A episode with Praxis students! Christopher loves hearing from his listeners. Feel free to email him, connect on FacebookTwitter, Instagram and subscribe on iTunes!

211: Q&A on Niche Down with Praxis Students Pt. 1

Niche Down Q&A With Praxis Students Pt. 1 Legends and Losers

How do you design a legendary career and life? On this special Q&A episode of Legends and Losers, Christopher Lochhead hangs out with 75 young Praxis students enroled in the program by the one and only Isaac Morehouse. They talk how to niche down and what it takes to become undeniable.

“To be different, to create something new, you have to identify a problem that people are experiencing or deficit in the world, something that could be better and invent something that makes it better.” – Hannah Frankman, Praxis student

Three Things We Learned

Legends are different

When we come to think about it, every person, company or athlete that we respect or admire share some things in common with their fellow legends. These people are different and they follow their different, not bothering to fit in. They’re original, unique, took and broke new ground, and left the world changed forever.

Legends niche down

Legendary people become successful by proactively positioning themselves. They specifically tell the world how to think about them, what problem they solve and why that problem matters. By doing so, they become evangelists for that problem and turn it into the niche that they become known for and dominate.

“Different” is more interesting than “better”

When you’re hustling in a category with a queen that shares two-thirds of the market, it’s close to impossible to be better. In the grand scheme of things, the game of better is less interesting. Being different still wins over more attention and reaps more success than trying to lap a competition.

Christopher got thrown out of school at 18, thinking that he was stupid. It wasn’t until he was 21 that he discovered he has learning differences. By embracing these and making the most out of his limited options, he was able to start his company and launch his career that is legendary in its own right.


Discover Praxis

Amazon – Niche Down

Amazon – Play Bigger

We hope you enjoyed this Legends and Losers Q&A episode with Praxis students! Christopher loves hearing from his listeners. Feel free to email him, connect on FacebookTwitter, Instagram and subscribe on iTunes!

203 Leah Busque: Engineer to Entrepreneur to Startup Investor

Leah Busque Engineer to Entrepreneur to Startup Investor Legends and Losers

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!