David Solomon is the CEO and Chairman of Goldman Sachs, the second-largest investment bank in the world – but this position was far from handed to him. As a teen and young adult, David raked leaves, babysat, flipped burgers at McDonald’s, and worked at a summer camp, learning the importance of work ethic and perseverance early on.

David’s career trajectory had its highs and lows just like any other, but his hard work, resilience, and self-awareness led him to become a leader for over 43,000 employees at a firm that manages $1.5 trillion in assets.

In this episode, Randall and David discuss the importance of adaptability and persistent effort amidst challenges, the characteristics of leaders, how success and work-life balance are defined, and much more.

Topics Include:
-       How consistent difficulties create resilience
-       David’s advice for dealing with limiting and frustrating bosses
-       Whether or not luck and timing impact success
-       Defining success
-       The 3 most important aspects of leadership
-       The connection between time management, preparation, and accomplishments
-       The characteristics of a Goldman Sachs employee
-       How to establish your work-life balance
-       The biggest lesson David has learned
-       And more…

David Solomon is the CEO and chairman of The Goldman Sachs Group, Inc. Last year alone, Goldman Sachs managed $1.5 trillion in assets, had $60 billion in revenue, and employed 43,900 employees.

David began his career with the firm in 1999 as a partner, soon becoming the Global Head of the Financing Group. In 2006, he was named the joint head of the investment banking division, where he doubled profit margins over the next decade. He later served as president and COO of the firm before succeeding Lloyd Blankfein as CEO in 2018.

In addition to his work at Goldman Sachs, David is the chairman of the Board of Trustees of Hamilton College, serves on the Board of Trustees of New York-Presbyterian Hospital, and serves on the Robin Hood Foundation, New York City’s largest poverty-fighting organization.

Resources Mentioned:
Memos from the Chairman, by Alan C. Greenberg

Coaching and Staying Connected:

1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Sallie Krawcheck holds the world record for being fired the most times on the Wall Street Journal. She is also one of the most powerful and influential people on Wall Street, currently serving as CEO of an investment platform that manages over $1.5 billion in assets. By viewing success and failure as two sides of the same coin, she has overcome what few of us are capable of.

Sallie is a Wall Street legend, an author, and the co-founder and CEO of Ellevest, a digital investment platform built for women. Over the last 30 years, she has continuously broken barriers on Wall Street, navigating high-profile leadership positions at companies like Citigroup, Merrill Lynch, and Smith Barney (now Morgan Stanley).

In this episode, Sallie talks about how she went from a rocky and emotionally-scarring start on Wall Street to the “Eureka!” moments that defined her career. She dissects what to do when facing constant rejection, the significance of outworking others, and how to rank learning, money, and passion when it comes to work. She also discusses the importance of proactively supporting and advising others, navigating office politics as a woman, and why success and failure are two sides of the same coin.

Topics Include:

- The most important relationship a professional woman can have

- How one person led Sallie to realize her potential

- Working for money vs. passion

- Biases against women and minorities in the workplace

- Sallie’s world record

- Why you shouldn’t be the smartest person in the room

- How job candidates can separate themselves from the competition

- The #1 unwritten rule of success in business

- And more…

Sallie Krawcheck is known as one of the most influential women on Wall Street, but the title hasn’t come without its challenges. From navigating constant workplace discrimination to being fired for maintaining her honesty, Sallie has jumped continuous hurdles, moving from investment banking to becoming one of the top business research analysts in the game.

Her Wall Street career includes being named CFO of Citigroup and CEO of Merrill Lynch, the Citi Private Bank, Smith Barney, US Trust, and Sanford C. Bernstein. She is the co-founder and current CEO of Ellevest, whose mission is to put more money in the hands of women. Her recent book, Own It: The Power of Women at Work, talks about the power of resilience, risk-taking, and hard work to reach the top.

Resources Mentioned:
Own It: The Power of Women at Work
Ellevest

Coaching and Staying Connected:

1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Sallie Krawcheck holds the world record for being fired the most times on the Wall Street Journal. She is also one of the most powerful and influential people on Wall Street, currently serving as CEO of an investment platform that manages over $1.5 billion in assets. By viewing success and failure as two sides of the same coin, she has overcome what few of us are capable of.

Sallie is a Wall Street legend, an author, and the co-founder and CEO of Ellevest, a digital investment platform built for women. Over the last 30 years, she has continuously broken barriers on Wall Street, navigating high-profile leadership positions at companies like Citigroup, Merrill Lynch, and Smith Barney (now Morgan Stanley).

In this episode, Sallie talks about how she went from a rocky and emotionally-scarring start on Wall Street to the “Eureka!” moments that defined her career. She dissects what to do when facing constant rejection, the significance of outworking others, and how to rank learning, money, and passion when it comes to work. She also discusses the importance of proactively supporting and advising others, navigating office politics as a woman, and why success and failure are two sides of the same coin.

Topics Include:

- The most important relationship a professional woman can have

- How one person led Sallie to realize her potential

- Working for money vs. passion

- Biases against women and minorities in the workplace

- Sallie’s world record

- Why you shouldn’t be the smartest person in the room

- How job candidates can separate themselves from the competition

- The #1 unwritten rule of success in business

- And more…

Sallie Krawcheck is known as one of the most influential women on Wall Street, but the title hasn’t come without its challenges. From navigating constant workplace discrimination to being fired for maintaining her honesty, Sallie has jumped continuous hurdles, moving from investment banking to becoming one of the top business research analysts in the game.

Her Wall Street career includes being named CFO of Citigroup and CEO of Merrill Lynch, the Citi Private Bank, Smith Barney, US Trust, and Sanford C. Bernstein. She is the co-founder and current CEO of Ellevest, whose mission is to put more money in the hands of women. Her recent book, Own It: The Power of Women at Work, talks about the power of resilience, risk-taking, and hard work to reach the top.

Resources Mentioned:
Own It: The Power of Women at Work
Ellevest

Coaching and Staying Connected:

1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

If it weren’t for Steve Case, the internet may never have become part of our everyday lives. He is the co-founder of AOL, after all. But that’s just the tip of the iceberg when it comes to Steve’s search for excellence. 

As one of the most important entrepreneurs in the last hundred years, Steve is driven by a mission to create entrepreneurial opportunities in surprising places as a means to close the opportunity gap. Since 2003, he’s invested in more than 500 companies and his contributions have influenced the lives of hundreds of millions of people, if not billions of people around the world.

In this episode, Randall and Steve discuss whether someone can learn to be an entrepreneur or does they have to be born with the gene, the importance of failure and our ability to overcome it, the role entrepreneurs play in creating jobs, why innovation is key when starting a company, and so much more.

Topics include:
-The digital revolution
-Raising venture capital
-Establishing partnerships
-The Attacker/Defender dynamic
-Characteristics of great entrepreneurs
-Closing the opportunity gap
-How to identify promising entrepreneurs
-Mistakes to avoid when looking for funding
-Philanthropy and The Giving Pledge

Steve Case is one of America’s best-known and most accomplished entrepreneurs and a pioneer in making the Internet part of everyday life. Steve’s entrepreneurial career began in 1985 when he co-founded America Online (AOL). Under Steve’s leadership, AOL became the world’s largest and most valuable Internet company, driving the worldwide adoption of a medium that has transformed business and society. At its peak, nearly half of Internet users in the United States used AOL.

Steve’s passion for helping entrepreneurs remains his driving force. He was the founding chair of the Startup America Partnership—an effort launched at the White House to accelerate high-growth entrepreneurship throughout the nation. He is also a Presidential Ambassador for Global Entrepreneurship, was the founding co-chair of the National Advisory Council on Innovation & Entrepreneurship and a member of President Obama’s Council on Jobs and Competitiveness where he chaired the subcommittee on entrepreneurship.

Books mentioned:
The Rise of the Rest, by Steve Case
The Third Wave, by Steve Case
The Third Wave, by Alvin Toffler

Coaching and Staying Connected:

1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

If it weren’t for Steve Case, the internet may never have become part of our everyday lives. He is the co-founder of AOL, after all. But that’s just the tip of the iceberg when it comes to Steve’s search for excellence. 

As one of the most important entrepreneurs in the last hundred years, Steve is driven by a mission to create entrepreneurial opportunities in surprising places as a means to close the opportunity gap. Since 2003, he’s invested in more than 500 companies and his contributions have influenced the lives of hundreds of millions of people, if not billions of people around the world.

In this episode, Randall and Steve discuss whether someone can learn to be an entrepreneur or does they have to be born with the gene, the importance of failure and our ability to overcome it, the role entrepreneurs play in creating jobs, why innovation is key when starting a company, and so much more.

Topics include:
-The digital revolution
-Raising venture capital
-Establishing partnerships
-The Attacker/Defender dynamic
-Characteristics of great entrepreneurs
-Closing the opportunity gap
-How to identify promising entrepreneurs
-Mistakes to avoid when looking for funding
-Philanthropy and The Giving Pledge

Steve Case is one of America’s best-known and most accomplished entrepreneurs and a pioneer in making the Internet part of everyday life. Steve’s entrepreneurial career began in 1985 when he co-founded America Online (AOL). Under Steve’s leadership, AOL became the world’s largest and most valuable Internet company, driving the worldwide adoption of a medium that has transformed business and society. At its peak, nearly half of Internet users in the United States used AOL.

Steve’s passion for helping entrepreneurs remains his driving force. He was the founding chair of the Startup America Partnership—an effort launched at the White House to accelerate high-growth entrepreneurship throughout the nation. He is also a Presidential Ambassador for Global Entrepreneurship, was the founding co-chair of the National Advisory Council on Innovation & Entrepreneurship and a member of President Obama’s Council on Jobs and Competitiveness where he chaired the subcommittee on entrepreneurship.

Books mentioned:
The Rise of the Rest, by Steve Case
The Third Wave, by Steve Case
The Third Wave, by Alvin Toffler

Coaching and Staying Connected:

1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Mike Horn is a person who has redefined the boundaries of human endurance. He’s trekked to the North Pole in complete darkness, scaled four of the world’s 8,000-meter tall mountains, circled the globe not once, but twice (once on the Equator and once on the Arctic Circle), and the list goes on.

And while his expeditions are often life-threatening, and despite some incredibly close calls, he’s not one to be reckless in accomplishing his goals.

In this episode, Randall and Mike discuss his journey to becoming the world’s greatest modern-day explorer, covering everything from lessons learned in early childhood to his groundbreaking expeditions. 

They discuss how mistakes can and should be used to our benefit, viewing inspiration as a two-way street, why making peace with failure is an absolute requirement of success, how psychological attitude and mental strength determine whether we achieve excellence, where money should rank in our career goals and life, and so much more.

Topics Include:
- How freedom leads to creativity
- Power of positive reinforcement
- Investing in education
- The relationship between self-discipline and motivation
- Setting and achieving goals outside of our comfort zone
- Ingredients to success
- Understanding fear
- Sports psychology
- Taking ownership of our problems
- Addressing environmental and ecological issues

Mike Horn is globally acknowledged as the world’s greatest modern-day explorer. From swimming the Amazon River solo and unsupported to an un-motorized circumnavigation of the globe at the equator, Mike’s list of accomplishments as a solo explorer is unparalleled. In two decades, he has seen more of the Earth than possibly any other human. He walked to the north pole during the dark season (more people have been to the moon) and has scaled the world’s 8,000-meter peaks including a recent attempt to paraglide K2.

For 25 years, as one of the top motivational speakers, he has inspired and educated the world by pushing the limits of human ability through a series of groundbreaking expeditions, always naturally powered and often solo. Mike also engages in mental coaching of elite sports teams. Through his coaching, Mike already contributed to the victory of several teams, including Germany’s national football team during the 2014 World Cup, the Kolkata Knight Riders cricket teams and the Mumbai Indians in India, and the Proteas in South Africa.

Resources Mentioned:
Mike Horn, Amazonas (1997-1998)

Coaching and Staying Connected:

1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Mike Horn is a person who has redefined the boundaries of human endurance. He’s trekked to the North Pole in complete darkness, scaled four of the world’s 8,000-meter tall mountains, circled the globe not once, but twice (once on the Equator and once on the Arctic Circle), and the list goes on.

And while his expeditions are often life-threatening, and despite some incredibly close calls, he’s not one to be reckless in accomplishing his goals.

In this episode, Randall and Mike discuss his journey to becoming the world’s greatest modern-day explorer, covering everything from lessons learned in early childhood to his groundbreaking expeditions.

They discuss how mistakes can and should be used to our benefit, viewing inspiration as a two-way street, why making peace with failure is an absolute requirement of success, how psychological attitude and mental strength determine whether we achieve excellence, where money should rank in our career goals and life, and so much more.

Topics Include:
- How freedom leads to creativity
- Power of positive reinforcement
- Investing in education
- The relationship between self-discipline and motivation
- Setting and achieving goals outside of our comfort zone
- Ingredients to success
- Understanding fear
- Sports psychology
- Taking ownership of our problems
- Addressing environmental and ecological issues

Mike Horn is globally acknowledged as the world’s greatest modern-day explorer. From swimming the Amazon River solo and unsupported to an un-motorized circumnavigation of the globe at the equator, Mike’s list of accomplishments as a solo explorer is unparalleled. In two decades, he has seen more of the Earth than possibly any other human. He walked to the north pole during the dark season (more people have been to the moon) and has scaled the world’s 8,000-meter peaks including a recent attempt to paraglide K2.

For 25 years, as one of the top motivational speakers, he has inspired and educated the world by pushing the limits of human ability through a series of groundbreaking expeditions, always naturally powered and often solo. Mike also engages in mental coaching of elite sports teams. Through his coaching, Mike already contributed to the victory of several teams, including Germany’s national football team during the 2014 World Cup, the Kolkata Knight Riders cricket teams and the Mumbai Indians in India, and the Proteas in South Africa.

Resources Mentioned:
Mike Horn, Amazonas (1997-1998)

Coaching and Staying Connected:

1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Like many who are just starting out in their careers, Jimmy Pitaro was uncertain of the direction he was headed in as he prepared to enter the workforce. He was attending Cornell University where he had secured a spot on the football team, but Jimmy knew that the odds of him becoming a professional athlete were slim to nonexistent. 

Nonetheless, sports had always played an influential role in his life and he was determined to incorporate the world of sports into his career path. As the now Chair of ESPN, it’s safe to say that Jimmy had reached this goal, but not without learning many important lessons along the way.

In this episode, Randall and Jimmy discuss the progression of Jimmy’s career, how to recover from a huge disappointment, determining when you should stay on course or move on to something else, identifying the subject matter you are most passionate about to lead your career direction, finding opportunities to work with like-minded people, and so much more.

Topics include: 

-How Jimmy’s early love of sports shaped his future
-Importance of having a support network
-Why having compassion and respect for others is advantageous 
-Prioritizing mentorship
-Erring on the side of over preparation
-Jimmy’s “Four North Stars” at ESPN
-Creating a culture of innovation
-Why work ethic is the single greatest determinant of our success
-The relationship between fear and courage
-Networking
-Finding the right work-life balance

Jimmy Pitaro was named Chairman, ESPN and Sports Content on October 12, 2020. His focus is the entirety of ESPN's multimedia offerings - including live sports programming, sports news and original and non-scripted sports-related content, audio, digital and social endeavors - plus all sports-related content for Disney's cable channels, ESPN+, and ABC.

He was named ESPN president and co-chair, Disney Media Networks, on March 5, 2018, after serving eight years as a top Disney executive. In making the announcement, Bob Iger, then The Walt Disney Company chairman and chief executive officer, said, "Jimmy's appointment was the result of more than 20 years spent at the intersection of technology, sports and media."

Pitaro's record of success leading businesses focused on consumer products, digital initiatives and sports made him the quintessential selection for ESPN at a pivotal point in its then 38-year history: a time of unprecedented technological advancements and rapidly changing consumer habits.

Pitaro originally joined The Walt Disney Company in 2010 as co-president, Disney Interactive, where he successfully led the turnaround of the digital media and gaming division.

He serves on a variety of industry and charitable boards, including the NCTA, the Paley Center for Media, The V Foundation, The National Football Foundation and College Football Hall of Fame, Pacer and CoachArt. Pitaro also serves as Co-Committee Chair of the March of Dimes, and is a Board Observer at Draft Kings. He is a member of the Cornell Athletic Alumni Advisory Committee.

Coaching and Staying Connected:

1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Like many who are just starting out in their careers, Jimmy Pitaro was uncertain of the direction he was headed in as he prepared to enter the workforce. He was attending Cornell University where he had secured a spot on the football team, but Jimmy knew that the odds of him becoming a professional athlete were slim to nonexistent. 

Nonetheless, sports had always played an influential role in his life and he was determined to incorporate the world of sports into his career path. As the now Chair of ESPN, it’s safe to say that Jimmy had reached this goal, but not without learning many important lessons along the way.

In this episode, Randall and Jimmy discuss the progression of Jimmy’s career, how to recover from a huge disappointment, determining when you should stay on course or move on to something else, identifying the subject matter you are most passionate about to lead your career direction, finding opportunities to work with like-minded people, and so much more.

Topics include: 

-How Jimmy’s early love of sports shaped his future
-Importance of having a support network
-Why having compassion and respect for others is advantageous 
-Prioritizing mentorship
-Erring on the side of over preparation
-Jimmy’s “Four North Stars” at ESPN
-Creating a culture of innovation
-Why work ethic is the single greatest determinant of our success
-The relationship between fear and courage
-Networking
-Finding the right work-life balance

Jimmy Pitaro was named Chairman, ESPN and Sports Content on October 12, 2020. His focus is the entirety of ESPN's multimedia offerings - including live sports programming, sports news and original and non-scripted sports-related content, audio, digital and social endeavors - plus all sports-related content for Disney's cable channels, ESPN+, and ABC.

He was named ESPN president and co-chair, Disney Media Networks, on March 5, 2018, after serving eight years as a top Disney executive. In making the announcement, Bob Iger, then The Walt Disney Company chairman and chief executive officer, said, "Jimmy's appointment was the result of more than 20 years spent at the intersection of technology, sports and media."

Pitaro's record of success leading businesses focused on consumer products, digital initiatives and sports made him the quintessential selection for ESPN at a pivotal point in its then 38-year history: a time of unprecedented technological advancements and rapidly changing consumer habits.

Pitaro originally joined The Walt Disney Company in 2010 as co-president, Disney Interactive, where he successfully led the turnaround of the digital media and gaming division.

He serves on a variety of industry and charitable boards, including the NCTA, the Paley Center for Media, The V Foundation, The National Football Foundation and College Football Hall of Fame, Pacer and CoachArt. Pitaro also serves as Co-Committee Chair of the March of Dimes, and is a Board Observer at Draft Kings. He is a member of the Cornell Athletic Alumni Advisory Committee.

Coaching and Staying Connected:

1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Sarah Friar learned about the power of community from an early age. Growing up in Northern Ireland during a time of tremendous violence showed her the importance of finding common ground and taught her how to create resilience from within, both of which are lessons that she continues to live by today. Even in moments of fear and despair, Sarah was able to find her resilience and take risks throughout her career.

After checking all the boxes that she thought would lead her to become a partner at Goldman Sachs, Sarah received the news that she wouldn’t be getting the promotion she had been striving for. She could have stayed at Goldman, but her husband said something to her that she couldn’t shake — losing the promotion has set her free.

From there, Sarah considered what she’s good at, what she’s passionate about, and what the world needs, which ultimately led her to her current role. As the CEO of Nextdoor, a hyperlocal social networking service for neighborhoods, Sarah is now working to strengthen the power of community — a reflection of her lessons learned early on.

In this episode, Randall and Sarah discuss how curiosity and resilience are the keys to finding your path; how finding common ground can unlock social capital that allows you to get things done in the world; advice to women today who are working in a sexist environment; what to do when you aren’t passionate about your work but are making good money; why searching for an emotional connection helps to build stronger companies; why you should be taking risks in your career frequently; the role politics has in the workspace; how to use moments of failure to help you rise; and more…

Topics include:
-The power of community
-Why it’s necessary to do the nitty-gritty work
-Why it is important to learn both inside and outside of the classroom
-The importance of finding purpose at work
-How to use your fears to spur you into action
-Whether or not you should have a plan B
-Why extreme preparation matters
-Prioritizing mental health
-Why job hopping is a red flag
-How to strike the right work-life balance
-The secret side of philanthropy
-Why having a diversity of experience is advantageous

Prior to Nextdoor, Sarah served as the chief financial officer at Square. Under Sarah’s leadership, the company launched its initial public offering in 2015 and added $30 billion in market capitalization.

Sarah grew up in Northern Ireland and earned her MEng in Metallurgy, Economics, and Management from the University of Oxford and her MBA from the Stanford University Graduate School of Business, where she graduated as an Arjay Miller scholar.

Resources mentioned:
Nextdoor

Books mentioned:
Range: Why Generalists Triumph in a Specialized World,  by David Epstein

Coaching and Staying Connected:

1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn