Legends & Losers - Motivational Business Dialogues, With an Edge

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106: Leadership, Laughs & Authenticity with Doug Merritt, CEO of Multi-Billion Dollar Public Category King, Splunk

Most people make the career mistake of going for salary and title instead of working with a category. Why is it so important to work for a category king? Why do many of the biggest companies in the world struggle with innovation? How do you create a culture of innovation in a company? On this episode, we are joined by Splunk CEO, Doug Merritt who shares his journey from inside sales rep to the CEO of a $9 billion publicly traded company.

You have to think of a whole new approach, using stuff people have overlooked if you want to do something interesting. -Doug Merritt

Takeaways + Tactics

  • Great tech companies still exist-- in the enterprise space.  
  • If you’re fortunate enough to be around legendary, brilliant people, build relationships with them and learn from them.
  • We’ve gotten so caught up in the idea of a career path that we often lose sight of the fact that life is a journey. The path to who you want to become can be unpredictable.

At the start of the show, we talked about why some Silicon Valley CEOs don’t want to be coached, and Doug shared why coaches are so necessary. Next, we discussed the importance of learning from failure and Doug’s career trajectory. Towards the end we talked about why so many companies struggle with innovation.

We also discussed:

  • The distinction between enterprise and consumer companies in tech
  • Why you have to work for a category king
  • Why you shouldn’t “over-architect” your career

The greatest companies are created by innovation and doing things a differently. To have innovation in a company, you have to create a culture of openness, open debate, and disruptive orientation. You have to try, iterate, fall on your face, and be able to get back up. If you do that with persistence, you’ll move toward your goal, whether it’s on a personal level or in a company. You will learn so much more from being on a winning team that’s crushing it, than when you have a big title or a huge salary.


105: Mark Timm on Why Zig Ziglar Became the Category King of Sales Training

Zig Ziglar impacted over 250 million people in his lifetime and left an incredible legacy. Why is his message still so relevant and so powerful today? How was he both timeless and ahead of his time? What is true gratitude in this instant gratification world? What is causing the drastic drop in American entrepreneurship? On this episode, we are joined by entrepreneur and CEO of Ziglar, Mark Timm, who shares on the power of Zig Ziglar and why he’s still such a force.

What if the most valuable business that I will ever own, ever operate, ever found and ever be a part of was the business that I was going home to, instead of the business I went to that morning? -Mark Timm


  • The quality of your primary relationship when you’re in your 50s determines your longevity a lot more than your DNA.
  • It’s not a matter of “if” you’re going to fail, it’s a matter of “when”. The real question is are you going to learn from it, pivot and adjust-- and how fast can you do it?
  • An entrepreneur needs attitude, skill, and effort to be a top performer.
  • Regarding entrepreneurship: there’s no lack of ideas, we’re just missing the key ingredient of sticking it through and knowing that you’re going to fail a lot.

At the start of the show, Mark shared the personal transformation he had, and the impact that Zig Ziglar had on his life. Next, he talked about the work he’s doing with families and how it’s inspired by his own. Mark also talked about why failure is a necessary component of success, and what is really behind the entrepreneurship crisis.

We also discussed:

  • The problem people have with relationships and the role technology plays in it
  • Why podcasting allows for more authentic dialogue
  • The process of going from survival to significance

In the world of 140 characters, emojis, and memes, real gratitude and authenticity stand out. That’s why even today the legacy and impact of Zig Ziglar shows no sign of slowing down. His motivation reminds us that we can change who we are and where we are with what we put in our minds. We’re swallowed in surface level stuff and it’s consuming us, and that’s why we need authentic voices reminding us that life is a journey of discovering our full potential. Part of this process is failing and being able to get back up. It is so critical that we take inventory of our lives, and remember how we got to where we are and who helped us get there. Success isn’t an elevator up. It’s a staircase that can be steep at times, but it’s worth it.

Guest Bio
Mark is the CEO of the most valuable business in the world – his family. He is also the President and CEO of Ziglar Family. Go to http://marktimm.com/ for more information or to download his free book. Go to https://www.ziglar.com/ to listen to the podcast and follow up with their work.


104: Shaku Atre Takes Over Legends & Losers

Most new CMOs find themselves in a trap of trying to earn the right to do a category strategy before they even do the basics. What changes has the digital age brought to the role of the CMO? Why is it so insane to rebrand without the context of category design? Where is marketing headed, and who will succeed in that age? On this episode, Shaku Atre is back, but this time she puts Chris in the hot seat as he gives insights on marketing and category design.

Any branding strategy absent a category strategy is a waste of money, because you don’t know what you’re doing. -Christopher Lochhead


  • The best venture money is customers.
  • The value of a creative and strategic mind increases everyday.
  • Social media is only as good as the content.

At the start of the show, we talked about how Chris stayed ahead as a CMO, and why you’re toast if you don’t have the ability to capture attention. Next, we talked about some of the mistakes companies make with their venture funding and the magic triangle of becoming a category king. Towards the end, we talked about the future of marketing, and the value of creative and strategic marketers.

We also discussed:

  • Why the average CMO’s tenure is 44 months, and why it’s even shorter in tech
  • How digital has changed the role of the CMO
  • Why rebranding isn’t always the best thing

We’ve lived through direct mail, online marketing and now we’re in age of social media, content marketing and marketing automation. Where we’re going promises to bring us more surprises, innovations, legendary categories and the companies that will reign over them. We don’t serve anything or anyone when we play small, so as we continue to live in the greatest age to work in marketing, we have to always aim to play bigger and have the courage to be legendary.

Guest Bio 

Shaku is the founder and managing partner of the Atre Group, Inc. Santa Cruz, California, and New York City, NY- a business intelligence and data warehousing corporation. She is an internationally renowned expert who lectures on business intelligence, data warehousing, data mining, Customer Relationship Management (CRM) and database technology. Atre is also the author of six highly regarded books. She has worked with a number of organizations including financial institutions, manufacturing companies, Insurance organizations and health industry in resolving a number of business related issues by implementing appropriate technology. Shaku has worked for IBM in Germany and the USA and she was a partner at Price Waterhouse Coopers for a number of years. She has been an entrepreneur and has founded a number of IT companies in New York and California. Go to http://www.atre.com/ for more information and follow her on Twitter @ShakuAtre.


103: Bruce Cleveland on the Startup Traction Gap & Making A Difference To Entrepreneurs

A lot of people who come from big “category king” companies think they can automatically build a legendary business. How has history proven this notion wrong through the failure of a lot of start-ups? Why is it so important for founders to know how to sell and market, as much as they know their products? Can a company be hard and soft at the same time? On this episode, we are joined by Wildcat Venture Partners founding partner, Bruce Cleveland who shares on his time at Oracle and Siebel, and how he’s changing the way startups are built in Silicon Valley.

After the point you become an individual contributor, your job is to influence behavior. -Bruce Cleveland


  • Digital “oil” is data. The products that are going to let us prospect, refine, and monetize data are where wealth will be made.
  • There’s a lot of lip service and no action when it comes to hiring former military personnel and bringing them into the workforce.
  • The best leaders hold themselves to the same standards they hold other people to.

At the start of the show, we talked about the early days of Oracle and the lessons Bruce learned. Next, we juxtaposed the current culture of tech companies with the more military culture of older companies. We discussed why Bruce is passionate about hiring former military personnel, and the value of self-actualization. Towards the end, we talked about why we’re always representing the companies we work for.

We also discussed:

  • How the “bro culture” affects investing
  • Why the military is a great organization to draw inspiration from
  • Why technical founders need to learn how to market the product

A lot of startups fail because the team that built the product doesn’t have any experience taking the product into the market. That’s why it’s so critical that founders have the ability to sell their own products. It’s a fantasy that a technical founder can just hire a person to do this for them and have good results. Building a business is a team sport requiring different people who understand how to compete in a category. Running a business isn’t like running a frat house, so there’s a requirement to act accordingly. We have to take things seriously. We owe it to our employees, stockholders and customers .

Guest Bio
Bruce Cleveland is a Founding Partner at Wildcat where he focuses on investments in artificial intelligence (AI) marketing, EdTech, enterprise software as a service (SaaS) and the Internet of Things (IoT). His specific areas of interest include enterprise automation, education and training, and general business applications. Bruce likes working with early stage companies that use technology and data to increase revenue and decrease costs. Read his LinkedIn blog https://www.linkedin.com/in/brucecleveland/detail/recent-activity/posts/.


102: How Temitayo Osinubi Bootstrapped His Way to a Legendary Marketing Career

There’s a huge decline in entrepreneurship in America because access to capital is impossible for most young people. What methods can you utilize to get around this? What makes someone decide to be an entrepreneur even with the burden of student loans? On this episode, podcaster and entrepreneur Temitayo Osinubi shares on rising above adversity, starting an online marketing business, and doing a 4-year degree in 28 months.

The opportunities outweigh the BS. -Temitayo Osinubi

Takeaways + Tactics

  • Having skills is one half of the equation You also have to know how to play the game.
  • It may be cheaper to learn a skill online, but for people who don’t even have the money to start, students loans are the only way to fund your dreams.
  • One benefit of going to college is the alumni association and opportunities.

At the start of the show, Temitayo shared on getting his degree in online marketing at Full Sail University and the decision he made to go back to school at 28. We also talked about the misconception people have about taking the self-taught route in marketing. Towards the end of the show, he talked about his podcast: Marketing Disenchanted.

We also spoke about:

  • Name discrimination vs. color discrimination
  • The shocking amount of video data we’re producing every day
  • Why there are so many opportunities in social media and digital marketing

It takes a very wise person to decide to go back to school to get the tools they need to make their dreams come true. For a lot of people, money is a barrier to this life. However, student loans can knock down this barrier and open people up to more opportunities. There’s a decline in entrepreneurship because the costs of the education and the tools are just too daunting. The key is to not play a victim and complain about what’s wrong with the world. It’s about figuring out what you can do to level up and access the opportunities.

Guest Bio
Temitayo Osinubi, or Temi for short, is an author, podcaster, and Principal Consultant at Digital Marketing Advisers, a digital agency. Go to https://itunes.apple.com/us/podcast/the-marketing-disenchanted-podcast/id1188380816?mt=2 to subscribe to his podcast.



101: What It Takes to Be a Powerhouse CMO w/Jennifer Johnson, Janet Matsuda, & Deb Wolf

In marketing, being able to understand the product is valued now more than ever. How has this changed what is expected of a CMO and the work they do? What seat at the table does the CMO have in the company? How does the evolution of the company define what the CMO has to be able to bring to the table? On this episode, three legendary CMOs, Jennifer Johnson, Janet Matsuda and Deb Wolf take part in an insightful dialogue about their experiences helping brands create and dominate categories, and what it takes to be legendary at the job.

The most important criteria for any CMO to take a job is who is the CEO and do you want to work with them? -Jennifer Johnson

3 Things We Learned

We’ve ushered in an era where data and detail-oriented CMOs are as necessary as the creative “big idea” CMO

There’s a new kind of CMO today, one that has more of a product strategy background, and they deal a lot more with analytics and data. A lot of companies still want the creative type but you can’t ignore the data. This change also means existing CMOs have to be able to carry both skill sets. You can’t ignore the data but you also have to be able to find the emotional hook that’s going to get people.  

The biggest problem in business today is too many solutions without a problem

Many marketers spend so much time focusing on the solution that they spend very little time and effort focusing on the problem. It then forces other people to figure out a solution. Without clarity around the issue, positioning yourself and designing a category is an uphill climb. If you don’t get crisp on the problem you’re solving, nothing else is going to matter.

Go where your work is appreciated

If you’re in an organization that’s not friendly to women, or doesn’t gel with you, find a different job. Don’t try to fix that organization by yourself, unless you’re really in a position of power. Go somewhere you’re more more appreciated. In the same way, if a company doesn’t appreciate your skill set, go somewhere else. There are so many great places to work that will have such an appreciation for what you can do - go and work there.  

The CMO has to build connections and bridges across the company, because it’s all about interacting with each other to get the best out of the people and the company. For the CMO, every relationship is important, but the buck stops with the CEO. The CEO should determine whether you decide to join a company or not because that relationship will have the biggest impact on your role. Every executive should be interviewing the company they’re going into, as much as the company is interviewing them. The CMO determines the strategy for going to market, but the most strategic thing they can do is design a category in such a way that the market comes to them. To achieve this, you have to start with the category and the messaging. Your positioning and category will help drive everything and define your priorities.

Guest Bio

Janet Matsuda is the SVP of Product Marketing at Palo Alto Networks.

Deb Wolf is CMO of Lookout, responsible for building awareness, communicating Lookout’s value and driving customer demand across all lines of business.

Jennifer Johnson (JJ) is the first ever CMO for Tenable. JJ has experience in bringing innovation and creativity to company branding and stands behind the philosophy that category design is an essential skill for any CMO out there.


100: Show #100 Legendstravaganza

It’s been a wild and exciting ride on Legends and Losers, and we’ve reached 100 episodes! What are some of the biggest takeaways from the experience so far? What are some key insights we have about technology, startups and entrepreneurship? Why is “follow your passion” such bad advice? On this episode, we celebrate 100 legendary shows with a legendary dialogue.

How much you make is directly related to the value you provide to other human beings in the world. -Matt Johnson

3 Things We Learned

Innovation is going to go on steroids

So much has changed for us in this age, but we’ve only just seen the tip of the iceberg. In the next 15 years, we’re going to go through a hyper innovation cycle. By the year 2032, we’re going to look back to today and feel like it was the Stone Age.

Is this the end of the internet startup?

We haven’t had a big category king since Facebook and VCs just aren’t funding early stage companies as much as they did before. Startups have to scrape and scrounge before they can even get any VC involvement. What we’re seeing now more than ever is that VCs are funding companies that are in later stages of development, and in an emergent category.

The underrepresentation of women and minorities in business is costing the country billions

Certain demographic groups are underrepresented in the entrepreneur economy and it’s leaving a gap in business. If minorities started and operated startups at the same level as non-minorities, the US would have more than a million additional employer businesses and 9 and a half million more jobs. Women are half as likely as men to own a business that employs people and this consistent gender gap costs the country 1.7 million additional businesses.  

Entrepreneurship in America is still not as high as it was before the recession and there’s still work to do to open it up to women, minorities and people who don’t have a formal education. If we do this, we could see almost 2 million new businesses, and over 9 million jobs created. Additionally, we have to encourage entrepreneurship the right way, and stop telling people to just hustle or follow their passion. Our mission to contribute to this is ongoing endeavor.


099: How Villy Wang Uses Stories to Drive Social Change

Many people of color struggle to find where they belong and what resonates with them, because their races are rarely portrayed beyond stereotypes in the media. Who decides which stories get amplified? How do we make sure the voices of these people are seen and heard? How do we build a generation of creators, not just consumers? On this episode, we are joined by the founder of BAYCAT, Villy Wang, who shares on growing up in a world where she felt the story that represented her was omitted, how she found her voice and sense of belonging, and how she’s helping other people find theirs too.


Our stories weren’t lifted and they weren’t repeated with curiosity and with pride. -Villy Wang


  • At some stage of our life, each of us is “pre-disabled”, whether we’re a baby, injured, or pregnant. Making mobility easier for everyone will make the world a better place.
  • Education systems are now digital, and children who don’t have access to tech are left on the other side of the gap.
  • We’re in a new age of authenticity because we’ve been drowning in so much inauthenticity for so long.

At the start of the show, Villy shared on a project she’s currently working on. We also discussed her TED Talk, an event she shared in her speech, and her experience growing up in the melting pot of New York. Next we talked about racism in today’s world and how we can overcome it. We also discussed how monetization gets in the way of amplifying people’s stories and voices. Towards the end of the show, Villy shared why it’s so important to help people find their purpose.

We also spoke about:

  • Why we need to close the technological divide
  • What the absence of racism would look like
  • Why it’s so important to help children who face difficulties
  • How her mother inspired her

Everyone in this world wants to connect, belong, and feel like their story is important. When people’s stories get omitted, we rob the world of something necessary-- a rich, diverse truth of human existence. When nothing resonates with you, it’s hard to figure out where you belong. The gap that has been created by technology can either be inclusive or continuously divisive. If we fight for inclusiveness, we can enable the kind of justice and equality that will make the world a better place.

Guest Bio
Villy is the founder and CEO of BAYCAT, a nonprofit social enterprise that provides access, education and employment for low income youth, youth of color, and young women. Villy had a crazy dream: to create a new kind of social enterprise that helps kids who, like her, grew up in the projects. Raised by an immigrant single mother in New York City, Villy’s desire to tell her story forged a passion for using the digital media arts to capture stories untold and to create social change. That’s why she founded BAYCAT, leveraging her impressive 25-year background in education, arts programming, nonprofit business and law. Go to https://baycat.org/ to get involved.