Legends and Losers

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 data.world’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 data.world. It is a Public Benefit Corporation (and Certified B Corporation) focused on building the platform for modern data teamwork.

data.world 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 http://lucky7.io/portfolio 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!

230: Alex Hult from Pro Hockey to Restaurateur

Alex Hult from Pro Hockey to Restaurateur Legends and Losers

What do you do when your dreams get crushed? On today’s episode, Alex Hult shares his awesome story of business and life success. He tells us how he rose from a halted hockey career and became a legendary restaurateur.

“My mind was still thinking as fast, everything else was going as fast, but my body couldn’t just handle the speed that I wanted to go.” – Alex Hult

Three Things We Learned

Alex’s promising hockey career

Hockey has been a gigantic part of his life. Growing up in Sweden, Alex was one of the youngest players in the elite league and was ranked second in the country. With a bright career ahead of him, the San Jose Sharks eventually drafted him in 2003.

The injury that stilted everything

Alex Hult got injured the summer right after he got drafted by the Sharks while in a playoff as part of the Swedish team versus Russia. He prematurely got back in the ice a month after the injury. He was late to realize that injury took six to nine months of rehabilitation, and his career took a turn for the worse.

Becoming a restaurateur

After he got married, Alex gave thought to what he wanted to do and the restaurant business sounded fun, so he opened up HULT’S in 2013. On the fourth year of the restaurant, he opened the first Flights location which took off like crazy. At Flights, they serve everything from drinks to food in three different ways.

They give good value to their customers and this commitment shows in how they are full every single day. The massive success birthed a decision to spice things up and remodel the old HULT’S location to become another branch for Flights. Since then, Flights have become one of the most reputable restaurants giving their customers a whole new experience.


Alex is a Swedish native drafted in 2003 in the eighth round by the San Jose Sharks of the NHL. After a knee injury sidelined his career in hockey, he retired in 2009 after stints in the Swedish and European hockey leagues.

Alex met his wife, Sarah, who was Miss Nevada 2011 while pursuing a professional career in cards in Las Vegas. The couple married in 2013 and returned to the Alameda CA area where Sarah is from.


Flights Restaurants


New Flights soars into Los Gatos with fanfare

Hockey player turned restaurateur

Former hockey pro Alexander Hult traded skates for skillets

We hope you enjoyed Alex Hult 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!

229 Marjorie Scholtz Silicon Valley Entrepreneur

Marjorie Scholtz Silicon Valley Entrepreneur Legends and Losers

How do you find a passion in solving a problem that a lot of people face? On today’s episode, CEO of Verbhouse Marjorie Scholtz, shares the story of how she realized her passion. She also talks about how she built a diverse team founded on a single mission, designing a new category of company that makes it easier for people to be homeowners.

“Especially in cities like San Francisco, the home ownership rate is the lowest it’s been in 50 years.” – Marjorie Scholtz

Three Things We Learned

Keep walking if you don’t know what to do

People often get stuck when trying to search what they want to do in life. However, when they can tell what they don’t want to do, that means they have something to compare it to. They have yet to discover what it is that they clearly want to sink their teeth into.

Some entrepreneurs begin with problems to solve

Marjorie considers herself lucky to have found a problem that she is so passionate about that it’s all she can do. It is this sheer want to make a difference by solving the problem that steered her into this venture. Most entrepreneurs she resonates with are those who have accidentally fallen into their ventures because they want to solve a problem.

Building a healthy ecosystem of people

Marjorie’s team refers to a diverse set of people who really bring in different experiences and different viewpoints in the company. This distributed experience and viewpoints is what she calls the ecosystem. Despite the differences, however, they all share one common passion and belief in the problem that they’re solving.

One of the most difficult times of entrepreneurship is when you’re alone in your head and you have no one else to start buying into your own theories and hypotheses. But with a mission-driven team, things get exciting. You are finally able to speak about your own ideas and get feedback, and this moves things along.


Recognized as a national expert, Marjorie Scholtz is a tireless advocate of homeownership. Before launching Verbhouse, Marjorie spent a decade as founder and CEO of Stangl Advisors.

With more than $100M in loan modifications, real estate dispositions and acquisitions during and after the financial crash, she helped many homeowners find a path toward a more secure financial future.

Her passion to empower people, coupled with deep institutional knowledge, inspired her to create the Verbhouse Platform.




We hope you enjoyed  Marjorie Scholtz 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!

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!

226: Dushka Zapata Do I Need A Soulmate?

Dushka Zapata Do I Need A Soulmate Legends and Losers

How does creativity bloom and do we really need a soulmate? Dushka Zapata is a talented writer and a communications executive at Silicon Valley. Today, she joins us to talk about writing, soulmates, the difference between blame and responsibility, and a whole lot more.

“The greatest lie ever told is that there is someone out there that can make you peaceful, happy and full.” – Dushka Zapata

Three Things We Learned

Creativity blooms from unpredictability and solitude

Dushka thinks that her fast-paced workplace along with everything else that happens to her on the regular enable her writing. In truth, being in one’s comfort zone can be gray and may kill the stories that one has to write. Striking the perfect balance between unpredictability and solitude to allow oneself to breathe helps in maintaining creativity.

Boredom and distraction are not a dichotomy

The inability to feel pleasure or anhedonia stems from both boredom and perpetual distraction. But distraction does not mean the complete opposite of boredom, and oftentimes unhealthy distractions take on the form of false entertainment fed to the brain. Perpetual distraction may also lead to burnout, especially if boredom still lingers even after giving in to one distraction after another.

Finding one’s soulmate will not fix you

Dushka actively answers questions on Quora and one of the many things that she has been asked is whether or not we need a soulmate. But this is just one of the many lies that we from every other person. We don’t need to find someone to end our suffering from dissatisfaction and despair or being disheartened and lonely, as this belief oftentimes enhances a permanent sense of restlessness.

Humans are already whole and our secret sense of dissatisfaction and loneliness is actually inherent to the human condition. In fact, no one out there has the ability to bail you out. Eventually, you can pick out someone to walk beside you through everything, but the antidote to your loneliness does not exist in anyone outside of yourself but you.


Dushka Zapata is a best-selling author and her work has been viewed over 120 million times on Quora. She serves as the VP of Communications at public technology company Zendesk.






We hope you enjoyed Dushka Zapata 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!

225: Foreground vs. Background Conversations – Bix & Joe Bickson

Foreground vs Background Conversations - Bix & Joe Bickson Legends and Losers

Which is the winner in a comparison of foreground vs. background conversations? On today’s episode, Bix and Joe Bickson join us for another conversation tackling a tenet of future hacking. They talk about how the power dynamics in the company not only affect performance but also derail communication lines.

“The first practice we’re asking executive teams to have is to say the background conversations in the meeting.” – Joe Bickson

Three Things We Learned

Power dynamics still prevail in organizations

People are often trained to think that the more senior members of organizations have more authority and power. This prevents the kind of uninhibited conversations to create new opportunities for growth from happening. These old constructs, relics of the system birthed from the industrial revolution still lingers even at present day.

Why power dynamics deter growth

Because of this authoritarian system adopted from eons past, people in power oftentimes end up drinking their own bathwater. Their subordinates tell them how great and inspiring they are. Positive feedback is feedback that gets bent out of shape and it’s in no way of use to future hacking.

Background conversations matter

Most executive meetings feel suppressed. People are concerned about not only the subject matter to be discussed, but also the manner by which they discuss items in an attempt to maintain professionalism. But as soon as people leave these meetings, background conversations happen, and these are the type that should actually be encouraged in organizational circles.

When people talk about wanting to hack the future, they want to achieve something meaningful to step up in their life and business. But the delta between where they are and where they want to be, as well as with who they are and who they want to be sometimes gets in the way. To traverse this delta, people in chairs must come to love the gap and address the difficulty of power dynamics in organizations.


Bix and Joe Bickson are a team of a baby boomer and millennial working together to create new organizational DNA.



We hope you enjoyed Foreground vs. Background Conversations – Bix and Joe Bickson 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!