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129 How to go from Sales Rep to Chairman of The Board in Silicon Valley w/ Elisa Steele

129 How to go from Sales Rep to Chairman of The Board in Silicon Valley w/ Elisa Steele

In this episode, we are taken for a ride on how to go from sales rep to Chairman of the board with the amazing Elisa Steele. We have a powerful conversation about how she went from sales rep to regional sales to CMO, then CEO.

We also talk about what she’s learned from working in massive tech companies like Microsoft and Yahoo and many more, Wait for the part where she gives advice on how women can design legendary careers and have children too.

From Sales Rep to CEO

Elisa Steels is the Chairman of the board of two publicly traded tech companies, Cornerstone on Demand and Namley. She’s also on the Board of $25B Splunk. More of her career background includes former CEO of Namley and Jive and former CMO of Skype, and Yahoo.

She candidly shares what she learned from her career in these huge tech companies and from smaller entrepreneurial companies. From the time she graduated, she had a clear vision of what success looks like and she believes she will achieve it through sales. 

“If I went into sales, then its really clear. If I’m successful, I made or overachieve my number. Nobody can be subjective about that. If I go into some of these other fields, that was like, a complete mystery to me, how do I know if I am actually gonna make it? – Elisa Steele

Legendary Career Woman

Initially, Elisa shares the only one thing she wished for her career: to not work with other people. The second thing she wished was to have financial independence. She believes that if women do not build resources for themselves, the critical decisions will be left to other people other than themselves. 

“I was motivated by the fact or maybe even terrified by the fact that I wouldn’t have choices in life if I didn’t have resources. If you don’t have resources, then decisions in your life are up to somebody else. Resources equals choice.” – Elisa Steele

For Elisa, resources generally are assets. It is representative of the things that help women make a decision on what they want to do. Creating some wealth will make those choices, especially those that are critical in life.

How to Disagree and Commit

Elisa is a powerful executive and she shares the thought of disagreeing, but still committing. She describes herself as a consensus builder.

“Being the smartest in the room doesn’t actually help anybody. You have to actually make decisions and together, execute, because strategy is nothing without strong execution. Executiion is everything. Even if the strategy is off, you can still win, if you execute. Disagree but commit and be one team.” – Elisa Steele

To hear more information about Elisa Steele and to listen to his tips on how to go from sales rep to chairman of the board, download and listen to the episode.


Elisa Steele is the Chairman of the Board at Cornerstone (CSOD) and Namely; Board Director at Splunk (SPLK) and an advisor to Advisor to Tile and

She’s the former CEO of Namely  and Jive Software, Inc., 

Ms. Steele served as Chief Marketing Officer and Corporate Vice President, Consumer Apps & Services at Microsoft Corporation, a worldwide provider of software, services and solutions, and Chief Marketing Officer of Skype, an Internet communications company, from 2012-2014. 

Ms. Steele also has held executive leadership positions Yahoo! Inc. and NetApp, Inc. 

Ms. Steele has served as a member of the board of directors of Cornerstone OnDemand, Inc., a learning and human capital management software company, since 2018. 

Ms. Steele holds a B.S. from the University of New Hampshire and an M.B.A. from San Francisco State University.


Linkedin – Elisa Steele

Twitter: – @elisasteele

We hope you enjoyed this episode of Follow Your Different™! Christopher loves hearing from his listeners. Feel free to email him, connect on Facebook, Twitter, Instagram and subscribe on iTunes! Get amazing, different stories on business, marketing, and life. Subscribe to our newsletter The Difference.

028 Dorie Clark Reinvent You

Dorie Clark Reinvent You Follow Your Different™ Podcast

What exactly does reinventing yourself entail? Expert Dorie Clark joins us today for a conversation about designing one’s new identity, why social proof matters, and a lot more.

Winning Over the Team

To reinvent oneself means giving in to the want to go toward a certain direction. Once you figure this out, you also need to realize that a lot of the process is about winning over the internal team. Who you surround yourself with as you begin reinventing yourself matters a lot.

“Ironically in the reinvention journey, the people closest to you are gonna be the least supportive initially.” – Dorie Clark

People you’ve built relationships with are more tied to who you’ve been than you are. They come from a good place, not to mention that they have the most at stake in this reinvention. You need to develop a strategy to help them understand your intentions and see your determination.

The Power of Dormant Ties

Since reinvention involves established relationships with people, you must also grasp the concept of ties. These include strong, weak, and dormant ties. Dormant ties come from strong bonds shared with people who have gone off in directions completely separate to yours.

Dormant ties can be particularly powerful when rekindled, especially with the positive connection and thoughts that come with them. That you have some form of contribution to each other’s success makes it a lot easier when you reunite. With ties like so, you will find people to root for you in your process of reinvention.

Creation of Content

The other key component is proof that you can muster to support your new identity. People are skeptical, and you have to hammer it home that you are serious about them. This is where content creation around your new subject area comes into play.

“It’s a way of simultaneously demonstrating your expertise. It enables you to have a networking vehicle. It allows you to create these sustained reminders.” – Dorie Clark

To hear more about Dorie’s expert advice on reinvention, download and listen to the episode.


Dorie Clark is “an expert at self-reinvention and helping others make changes in their lives,” says The New York Times. She’s an adjunct professor at Duke University and a bestselling author.

Her book, Stand Out, was named the #1 Leadership Book of 2015 by Inc. Magazine. She’s also a regular contributor to HBR.




We hope you enjoyed Dorie Clark on this episode of Follow Your Different™! Christopher loves hearing from his listeners. Feel free to email him, connect on Facebook, Twitter, Instagram and subscribe on iTunes!

027 David Osborn Wealth Can’t Wait

David Osborn Wealth Can’t Wait Follow Your Different™ Podcast

How do you overcome a compounded fear of failure to become legendary? On today’s episode, author, entrepreneur, and real estate investor David Osborn joins us in a conversation about making money, building capital, and so much more.

“You go to work for capital so your capital can eventually go to work for you.” – David Osborn

Thinking Big, Not Delusional

David started out as a realtor, working under his mom’s team for three years. Over time, he realized he no longer wanted to sell so he ventured out into setting up franchises. With the right company, time and work ethic as well as a dash of mistakes and failures, he and his team have sold billions.

When you focus on the delta of where you are and where you want to be, it becomes clear that making the first million is way too hard. But it’s just as important to think massively big, and not delusional, to get started. It takes so much longer and harder than people can imagine and be willing to admit, after all.

“People always look at the credit and the money that an entrepreneur makes and they way underestimate the amount of risk and amount of failure.” – David Osborn

An Idiot Prior to Success

David first opened up a franchise in 1996, and it took ten long years before he could make money. It was a sweet two years, until the massive crash of 2008. Luckily enough, he had a great company to support him through it. But not all entrepreneurs are on equal footing.

An entrepreneur that has to scramble all the way up will look like an idiot for ten years before they get rewarded. And sometimes, the rewards could be more than they probably should get.

“The reason is you spent those ten years where every day there’s a chance you could have nothing the next day.” – David Osborn

Overcoming Fear Through Crazy

It takes experiencing hurt and failure for fear to manifest. We find punishment, pain, and psychological difficulty so aversive that we steer clear of ladders going up.

Even the most successful entrepreneurs get afraid. But it’s finding the crazy force to drive you through the journey that spells all the difference.

To hear more about David’s views on free will and capital building, download and listen to the episode.


After sticking out his thumb and traveling the world, David returned home to Austin, Texas broke and unemployed, at the age of 26. Though his travels may not have yielded wealth, they instilled the key motivation that he brings to every part of his life to create it — freedom.

Because to have everything you ever wanted takes the opportunity to design your life and believe it can happen.

Through this intention, David began to test his entrepreneurial merits alongside his business-partner mom in the world of real estate. The results were nothing short of remarkable. In less than 10 years, David would go on to build one of the top real estate brokerages in the world, founding over 50 companies.

Yet, more than anything else, the inherent freedom derived from his success awards him the time to focus on the importance on what matters most: being a proud father of two beloved daughters, a son, and husband to the wonderful and talented Traci Osborn.

Today, still rooted in his boundless sense of adventure, David continues to travel the world not only to be enlightened by new experiences but to share his insight and expertise with others so they, too, can truly be free.


Wealth Can’t Wait – Amazon

Homo Deus: A Brief History of Tomorrow – Amazon

Happiest Countries – Forbes

We hope you enjoyed David Osborn on this episode of Follow Your Different™! Christopher loves hearing from his listeners. Feel free to email him, connect on Facebook, Twitter, Instagram and subscribe on iTunes!

013: Quit Your Corporate Job & Go Solo w/ Eddie Yoon

Quit Your Corporate Job & Go Solo w/ Eddie Yoon Follow Your Different™ Podcast

Today, Eddie Yoon unpacks a recent Harvard Business Review article with his co-author Christopher. Together, they answer some questions, concerns, and explain further why you should quit your corporate job and go solo.

It’s All in the Data

Eddie and Christopher’s HBR article has been receiving a lot of attention. Some of the people amid the buzz expressed their concerns about their thesis. But the data say it all: nearly 70% of solopreneurs make $100,000-250,000 in a year.

This figure is almost twice as much as the average US household. And it is much higher than what Glassdoor reports the average US executive makes yearly—$121,500. It seems solopreneurs are doing as well, if not exceedingly better, than most executives.

“If solopreneur was an industry and a company, everyone would be flocking to this industry in the same way that people did it for Silicon Valley or investment banking or consulting.” – Eddie Yoon

Importance of IPOs

Initial public offering (IPOs) have always been tech-related. But there are notable people who have done it in a non-digitized fashion. One example is Steve Hughes who launched a special purpose acquisition company and eventually skyrocketed as a solopreneur.

To go solo, a bridge needs to be crossed. You must know your investor story and who your target investors are. You must also know why they should believe that you’re worthy of your multiple.

“I think that more people are figuring out that market exists and [so], ‘Why not me?’” – Eddie Yoon

Breaking Out to Do Better

So many people are afraid to break out because of the corporate mothership and the financial aspect tied to the choice. But there are those who confronted their fear of not making enough and ended up earning more while working less.

The other odd benefit to going solo is that as an outsider, solopreneurs tend to be a lot smarter than those who are tied to a company.

“Maybe that’s the extra value that perspective gives you.” – Eddie Yoon

To hear more about the ultimate way of monetizing yourself and making an emotional business case for going solo, download and listen to the episode.


Eddie Yoon is the founder of EddieWouldGrow, LLC a think tank and advisory firm on growth strategy.

Prior to this, he was a partner at The Cambridge Group, a strategy consulting firm that helps Fortune 500 CEOs drive growth by unlocking consumer demand. His work over the past two decades has driven over $5 billion dollar of annual profitable growth in consumer packaged goods, durables, robotics and energy.

Eddie is one of the world’s leading experts on finding and monetizing superconsumers to grow and create new categories. He is the author of the acclaimed book, Superconsumers: A Simple, Speedy and Sustainable Path to Superior Growth (Harvard Business School Press, 2016).

He is also the author of over 40 articles, including Make Your Best Customers Even Better (Harvard Business Review magazine, March 2014) and Why It Pays to Be a Category Creator (Harvard Business Review magazine, March 2013). Additionally, he has been quoted in the Wall Street Journal, The Economist, Forbes and has been a keynote speaker in the U.S., Canada, Kenya, Australia, New Zealand, Denmark, the UK and Japan.

Eddie lives in Chicago with his wife and three children.


Harvard Business Review Article by Eddie Yoon & Christopher Lochhead:

Glassdoor – Executive Salaries

Superconsumers on Amazon



We hope you enjoyed Eddie Yoon on this episode of Follow Your Different™! Christopher loves hearing from his listeners. Feel free to email him, connect on Facebook, Twitter, Instagram and subscribe on iTunes!

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!

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!