

In Search Of Excellence
Randall Kaplan
We all have dreams of being successful and achieving excellence in our lives. But we inevitably experience resistance, challenges, and obstacles in the pursuit of our dreams. In Search of Excellence provides us with the inspiration we need to overcome these obstacles and accomplish our goals. In Search of Excellence takes us through the stories, routes, and strategies of people from hundreds of different backgrounds who have achieved excellence in both their professional and personal lives. Guest features include Sharon Stone, Kevin O'Leary, Sammy Hagar, Lara Logan, Sam Zell, and many more.
Episodes
Mentioned books

Aug 2, 2022 • 1h 9min
Apolo Ohno: From Last Place to Olympic Gold | E25
Apolo Anton Ohno is the most decorated Winter Olympian of all time. Between the 2002, 2006, and 2010 Winter Olympics, Apolo earned eight Olympic medals in short-track speed skating. Even as a child, Apolo’s athletic ability was evident, at the young age of 14, Apolo won his first major speed skating title, after just six months of training. But, despite his incredible talents and drive, Apolo faced setbacks and struggles from managing his mental health, navigating adolescence and his rocky relationship with his father, to tuning his competitive spirit. Apolo attributes his massive success as a speed skater and athlete to his fear of failure.In this episode, Randall and Apolo talk about what it takes to succeed at the highest level, and Apolo shares how the struggles he faced growing up and his unique relationship with his father shaped him into the athlete and man he is today. Apolo talks about what he learned from his failure at the 1998 Olympic trials, talks about the four foundations of mental health, and shares tips on how to set a regimen for mental health. Topics Include: - Advice to people afraid to fail - Winning his first big race- How to sustain performance level after success- Advice for parents navigating relationships and experiences with their children - The role of genetics in sport and excellence - Experience of 2002 Olympic Games - Going the extra mile and the role of extreme preparation - Elements of success- Passion and money's role in success- Five golden principles for overcoming challenges- Philanthropy and the importance of giving back- And other topics… Apolo Ohno is America’s most decorated Winter Olympian of all time, earning eight Olympic medals in short-track speed skating across the 2002, 2006, and 2010 Winter Games. He was an NBC sports analyst for the Sochi 2014 and PyeongChang 2018 Winter Games and is a global ambassador for the Special Olympics and the Winter Olympics. Among his other athletic accomplishments, Apolo won season 4 of ABC’s Dancing with the Stars and participated in the 2014 Ironman World Championship Triathlon in Kona, Hawaii. Apolo is also the author of the New York Times best-seller, Zero Regrets, A Journey, the autobiography of Apolo Anton Ohno, and his latest book, Hard Pivot. He is a regular speaker at hundreds of organizations from Fortune 100 companies to nonprofits. Resources Mentioned:Sandee.comApolo Ohno WebsiteCoaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Jul 19, 2022 • 1h 10min
Daymond John: Rise, Grind, and Accomplish Your Goals | E24
If there is someone who knows the power of hard work, it’s Daymond John. As a young man growing up in the neighborhood of Hollis, Queens, Daymond's entrepreneurial talent took off when he started a clothing line with a $40 budget. At the time, Daymond was hand-sewing hats between his shifts at Red Lobster. And today, Daymond's company, FUBU, has over $6 billion in sales.Daymond is not only one of the most successful fashion icons of his generation but is also a sought-after motivational speaker and branding expert. He is a beloved “Shark” on ABC’s hit show Shark Tank and a best-selling author. Daymond is an incredible example of how a combination of hard work, overcoming obstacles, passion, and creativity is a recipe for success. In this episode, Randall and Daymond talk about Daymond’s experience with dyslexia, starting FUBU and the struggles he overcame on his path to excellence, the importance of keeping an open mind and entertaining all opportunities, and Daymond shares the meaning behind his S.H.A.R.K. acronym. Topics Include:- What Daymond learned from seeing his mother struggle - Why you need to have an entrepreneurial mindset no matter what - Hacking yourself and the importance of ownership - The reasons why people buy clothes- The name FUBU and what he was trying to create - Cold calling as a factor in success- The “Boom” moment of entrepreneurship - The growth of FUBU- The importance of work ethic - When to give up your day job - Why he decided to host Shark Tank - Napoleon Hill’s book, Think and Grow Rich - The importance of creativity and persistence - How Daymond defines success - Advice on finding the right work-life balance - Philanthropy and giving back - Fill in the blank to excellence- And other topics… Daymond John is an American businessman and investor, best known as the founder and CEO of the American apparel company FUBU. Daymond is also the New York Times bestselling author of The Power of Broke. His most recent book is Rise and Grind.Daymond also stars as a "Shark" on ABC's hit show Shark Tank. Daymond’s impressive accolades include Brandweek Marketer of the Year, the Advertising Age Marketing 1000 Award for Outstanding Ad Campaign, Crain's Business of New York Forty Under Forty Award, and Ernst & Young’s New York Entrepreneur of the Year Award.Resources Mentioned: Think and Grow Rich by Napoleon HillCoaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Jul 5, 2022 • 1h 15min
Caryn Seidman-Becker: Becoming Indefatigable | E23
In 2002 Caryn Seidman-Becker created and ran a successful hedge fund that ultimately grew to $1.5 billion assets - an amount that was unheard of for a woman to manage at the time. When the financial crisis hit in 2008, Caryn - like thousands of other funds - closed her fund. She loved managing money, but decided to do something different - buy an airport-focused biometric-identity company that had raised $90 million and had filed for bankruptcy. She bid $5.87 million at the bankruptcy option, renamed the company CLEAR, raised $150 million in capital from various investors including Delta Airlines and United Airlines, and took the company public on June 30, 2021. Today, CLEAR’s market capitalization is $3.5 billion, landing Caryn on the Forbes list of America's Richest Self-Made Women (2021).Caryn’s journey to incredible success is one of pivoting, grit, instincts, determination, and leadership. When she decided to close her hedge fund, it would have been impossible to predict that she’d go on to reach massive success with the purchase of a bankrupt biometric-identity company. But if Caryn’s story teaches us anything, it’s that with insatiable curiosity, transparency, determination - and was she describes as being indefatigabel - you can accomplish your wildest dreams.In this episode, Randall and Caryn discuss how her childhood experiences and time attending the University of Michigan shaped her future, the importance of great teachers and mentors, the ability to overcome challenges and make tough decisions, the experience of buying a bankruptcy company and turning CLEAR into a company with $450 million in annual revenues, and advice for female entrepreneurs trying to find funding. Topics Include:- What values her parents instilled in her - Her first job in NYC in risk arbitrage - Why she started her hedge fund Arience Capital Management- The decision to close Arience in late 2008- Advice for people who want to start over and pursue their passions- What is CLEAR? - Transparency and real-time feedback in the age of social media- The impact of COVID on CLEAR and creating CLEAR Health Pass - The importance of preparation - and EXTREME PREPARATION - on the path to excellence - Caryn’s ingredients for success - Her view on making money- Fill In The Blank For Excellence- And other topics… Caryn Seidman-Becker is the Chair and CEO of CLEAR, an expedited airport security service that allows its members to quickly pass through airport security lines. Caryn and a colleague bought CLEAR's predecessor out of bankruptcy in 2010, and after raising $150 million from investors including Delta Airlines and United Airlines, she took the company public in June 2021 at a $4 billion valuation.Caryn serves on the boards of Home Depot and Lemonade, and in 2021 Forbes named Caryn the 27th wealthiest self-made woman in the United States. Caryn is also a dedicated philanthropist. In 2004, Caryn created The Happy Elephant Foundation which supports education, child wellness, and the New York City community, and she serves on the Board of Trustees of the 9/11 Memorial & Museum and on the board of the Department of Pediatrics at Mount Sinai Hospital in New York. She earned her B.A. in Political Science from the greatest college on the planet - the University of Michigan. Coaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Jun 21, 2022 • 1h 15min
Rachel Zoe: Nothing Replaces Hard Work | E22
Rachel Zoe is an icon in the fashion world. But before Rachel became a household name, she was 25 years old, styling celebrities like Britney Spears and the Backstreet Boys out of her West Village studio apartment. Rachel continued to make a name for herself as a stylist by putting together some of Hollywood’s most memorable red carpet looks and collaborating on iconic fashion lines. But, when she discovered that she had a unique platform to empower and inspire women from all walks of life, her creative and entrepreneurial mindset took over. And the rest is history, she became a best-selling author, a Bravo star, the Editor in Chief and publisher of The Zoe Report, and more. Rachel attributes her success to working hard, being open to opportunities, and always being the most prepared person in the room. But, being in the spotlight comes with fear, doubt, and criticism, all of which Rachel saw as learning experiences and opportunities for growth. In this episode, Randall and Rachel talk about how Rachel became the fashion icon and influencer she is today, how growing up in a well-off family surrounded by beautiful things influenced Rachel’s career, the experiences Rachel had starting as a freelance stylist, the importance of taking risks, why she’s always the most prepared person in the room, how she faced and overcame criticism and tabloid rumors, and everything she’s learned along the way. Topics Include: - The influence of her mother’s style - Education’s role in future success- The important advice she got from her father - Rachel’s advice for people who hate their jobs - Why getting over our fears is crucial on the path to success - Failure as a necessary ingredient to success - Rachel on designing her own style - How to deal with adversity at work- Rachel’s views on styling - Perceptions vs reality of being famous - Qualities she looks for in applicants- The importance of proactive thinking and planning for things to go wrong - Rachel’s ingredients to success - Marriage and life with Rodger and the secret to working with a significant other- The defining moment of Rachel’s career- Fill in the blank for excellence - And other topics… Rachel Zoe is an icon of the fashion world. She is a distinguished designer, editor, author, TV personality, and entrepreneur. She is the Creative Director of the Rachel Zoe Collection, which comprises ready-to-wear, footwear, and accessory lines. Rachel is the author of the New York Times bestsellers, Style A to Zoe and Living in Style. Rachel had a reality television series, The Rachel Zoe Project which aired on Bravo and ran for five seasons (2008-2013). In 2009, she founded The Zoe Report, a daily newsletter about what she was coveting in the worlds of lifestyle, beauty, and fashion. With the success of The Zoe Report, Rachel launched another paper focused on beauty, entitled Zoe Beautiful. Rachel and her husband Rodger Berman co-host the podcast, Works for Us. She is also a board member at Baby2Baby and an artist ambassador at Save the Children International. Resources Mentioned: Rachel’s Podcast Works for UsCoaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Jun 7, 2022 • 60min
Giada DeLaurentiis: The Dark Times Made Me Strong | E21
In the historically male-dominated culinary industry, Emmy-award-winning TV personality, celebrity chef, and New York Times best-selling author Giada De Laurentiis has not only helped pave the way for female chefs but has also shined a spotlight on the culinary arts as a whole. Giada has always been a trailblazer: from being the first in her family to graduate from college, to being the only woman in her class at Cordon Bleu in Paris, to being the first female chef to open a restaurant on the Las Vegas Strip at The Cromwell Hotel in Las Vegas. But along the way, Giada faced a great deal of adversity - getting bullied as a child, experiencing the devastating loss of her brother, and fighting the sexism and discrimination she faced in the culinary industry. For Giada, these challenges only fueled her fire - with her passion, a love of great food, and tremendous amount of perseverance - she had built an empire. In this episode, Randall and Giada talk about how Giada discovered her passion while working at her grandfather’s restaurant DDL Foodshow, the cultural Italian norms that impacted her life, how she launched her career, how she overcame challenges and practiced resilience, how her time on The Today Show gave her confidence, and everything she’s learned along the way. Topics Include: - Growing up in a traditional Italian family and her experiences in childhood- Getting bullied as a child- Being the first person in her family to attend college- Applying for and attending Cordon Bleu in Paris- Starting GDL foods - Landing Everyday Italian on the Food Network - Does practice make perfect?- Sexism in the culinary industry- Being the first woman to open a restaurant on the Las Vegas Strip- Giada’s Restaurant at The Cromwell- Challenges she had to overcome- How her brother’s passing influenced her life - The three most important ingredients to success- Advice for changing eating habits - Establishing the right work / life balance - Giving back and Stand Up To Cancer- And other topics…Giada De Laurentiis is an Italian-American celebrity chef, writer, and Emmy award-winning television personality. She was the host of Food Network's Giada at Home and has been the host or co-host of 18 television shows, and she also appears regularly as a contributor and guest co-host on NBC's Today show. She is the founder of the catering business GDL Foods, and the founder and CEO of Giadzy.com, an e-commerce platform which sells culinary goods and contains recipes, entertaining, and travel tips. Giada is also the author of nine cookbooks including the #1 New York Times Best-Seller Eat Better, Feel Better.Resources Mentioned: Giada’s WebsiteGiada’s BooksGiada’s RestaurantsCoaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

May 24, 2022 • 1h 13min
Mayor Eric Garcetti: Fight For What You Believe In | E20
From homelessness and the housing crisis to traffic and education, Los Angeles County Mayor Eric Garcetti faces challenging, pressing issues day in and day out. But how did a young kid who grew up in an immigrant family in the San Fernando Valley become the leader and change-maker he is today? All of Eric’s life experiences contribute to his ability to search tirelessly for solutions and lead the Los Angeles community towards a better future. When facing new opportunities, Eric considers the quote “only do this if you can’t not.” This motto has supported and encouraged Eric on his journey to becoming the 47th (and youngest) mayor of Los Angeles. We all have a lot to learn from Eric’s commitment to community, work ethic, and leadership skills. In this episode, Randall and Eric talk about how Eric’s childhood and early education shaped who he is today, how he learned the value of hard work, why he ran for public office, political issues Los Angeles is facing, why giving back is the most important thing we can do, the four most important qualities to have on the path to excellence, and all he’s learned along the way. Topics include: - How his trip to Ethiopia as a 16-year-old changed his life - Value of odd jobs and his work program for young Angelenos- Importance of both classroom learning and “real-life” learning - The ‘Will I regret this?” Test - Advice for people who want to be politicians- Why we should be more afraid of succeeding than failing - Why he views himself as “Storyteller in Chief” - The value of transparency and accountability in politics- The three C’s of leadership: convene, coerce, and convince- The importance of sharing power and using soft power- The education and housing crises in California - How to end homelessness- LA’s foster care system- His experience fostering seven children- Controversies he’s overcome - Why you can’t take yourself too personally- Value of having a great team - And other topics…Eric Garcetti is a fourth-generation Angeleno and the 42nd Mayor of Los Angeles. In 2017, Eric won re-election by the widest margin in the history of Los Angeles. He was recently appointed to serve as the US ambassador to India. Prior to becoming Mayor in 2013, Eric spent four terms as Council President on the L.A. City Council. Beyond his time in government, Eric served his country as an intelligence officer in the United States Navy Reserve, and taught at Occidental College and the University of Southern California. Eric received his B.A. and M.A. from Columbia University. He studied as a Rhodes Scholar at Oxford University, and later at the London School of Economics. He is also a jazz pianist and photographer. He and his wife, First Lady Amy Elaine Wakeland, have been foster parents for over a decade, and are the proud parents of a daughter, Maya. Coaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

May 10, 2022 • 1h 28min
Mark Cuban: Think Like A Shark | E19
Mark Cuban was born a serial entrepreneur. At age 12, he sold trash bags door to door. By age 16, he had a business selling stamps. During college at Indiana University, he taught disco lessons at sorority houses and opened a popular bar before he turned 21. So how does an average kid growing up in Pittsburgh go on to become a self-made billionaire? For some of us, it may be hard to imagine the person that we know today as Mark Cuban quit a job, was fired from another, had a business that closed down because somebody who worked there was on probation for prostitution, and slept on the floor of an apartment for many months after moving to Dallas. But it was these experiences that made Mark the businessman, investor, philanthropist, and billionaire that he is today. Mark’s journey is one of incredibly hard work, determination and perseverance, adapting to change, and learning from failure.In this episode, Randall and Mark talk about challenges on Mark’s path to excellence, the role Mark played in the early days of the internet with MicroSolutions, the story behind AudioNet/ Broadcast.com, taking it public, selling it to Yahoo for $5.7 billion, and how he sold his stock in what is considered one of the most brilliant business decisions of all-time. Randall and Mark also discuss Mark’s latest company The Mark Cuban Cost-Plus Drug Company, and his very sage advice for young entrepreneurs.Topics Include:- How his college experience prepared him for success- The lessons about sales Mark learned as a 12-year-old selling trash bags door to door- Why you can learn just as much from the bad companies as the good ones - The interview answer that got him a job with no experience - Mark’s brief career as an actor and reading for Stephen Spielberg - Why owning a sports team is unique from owning a business- Mark’s powerful Shark Tank episode with Tania Speaks Organic Skincare- The importance of preparation and learning from failure - Mark’s thoughts on parenting - How his work-life balance has changed over time- Mark’s charitable work through the Mark Cuban Foundation and Fallen Patriots Fund- And other topics…Mark Cuban is a serial entrepreneur, investor, owner of the Dallas Mavericks, and a host of Shark Tank on NBC. Mark made his initial fortune through the sales of his startups MicroSolutions and Broadcast.com in the 1990s, and he was was ranked #177 on the 2020 Forbes 400 list of the wealthiest residents in the United States.Mark is also the best-selling author of How to Win at the Sport of Business. Among many ventures, Cuban is also involved in the world of film and television and occasionally appears on popular television shows including Entourage, Dancing with the Stars, and The League. Mark graduated from the Kelley School of Business at Indiana University with a degree in management. He lives with his wife and children in Dallas, Texas.Resources Mentioned: The Fountainhead by Ayn RandCoaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Apr 26, 2022 • 1h 24min
Steve Romick: Manage Your Money Right | E18
Steve Romick grew up in a tight-knit family in the San Fernando Valley and was very driven from a very young age. Even as a five-year-old, he wasn’t interested in failure and never gave up easily, a personality trait that has carried Steve through his career. Today Steve manages nearly $20 billion in assets and is a managing partner at First Pacific Advisors (FPA), an LA-based money management firm that manages $29 billion. Steve’s passion to succeed, proficiency with numbers, and strong dislike of losing money have guided him to an accomplished career in money management, including the recognition of being named the 2013 Morningstar US Allocation Fund of the Year and earned him a nomination for Morningstar Manager of the Decade. Steve’s knowledge and perspective about money management and investing are built on 30 years of experience and understanding of risk and reward. In this episode, Randall and Steve talk about Steve’s first experience with wealth management as an intern (and later an employee) for Kaplan, Nathan, & Co., the importance of self-education and self-awareness in investing, how to grow a money management firm, modern investment strategies, and how to be a successful money manager. Topics Include: - How Steve’s father influenced his interest in philanthropy- The importance of reading and understanding shareholder reports - How to encourage people to learn and understand their investments- Who shouldn’t invest in a mutual fund - Low risk/high reward investments- Defining a hedge fund vs a mutual fund- Advice for getting a job in this industry - The ins-and-outs of growth at money management firm- The story behind his nomination for the Morningstar Manager of the Decade - What is the S&P 500 and why does it matter?- Defining the MSCI ACWI Index - Active vs passive investing - Why you should avoid secularly challenged businesses when deciding to invest- The two most important ingredients for success- Whether people should use a money manager or manage their own money- And other topics…Steve Romick is the managing partner at First Pacific Advisors, a money management firm based in Los Angeles that manages $29 billion across multiple investment strategies. Before joining First Pacific Advisors, Steve was the chairman of Crescent Management and worked in for Kaplan, Nathan, & Co. In addition to managing the $10 billion FPA Crescent Mutual Fund, he also co-manages the FPA Hawkeye Hedge Fund and other multi-advisor strategies. He serves on many philanthropic boards, including Cedars Sinai Medical Center, Our House, and Phase One.In 2013, Steve was the recipient of Morningstar’s U.S. Allocation Fund Manager of the Year and was nominated for the Morningstar Manager of the Decade. He earned a BS in Education from Northwestern University and lives in Los Angeles with his wife and three kids.Coaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Apr 12, 2022 • 1h 47min
Sammy Hagar: From Broke Kid To Rockstar Entrepreneur | E17
Sammy Hagar is one of the most prolific artists in the history of Rock and Roll. Playing in bands like Montrose and Van Halen, and with a successful solo career that included the rock anthem “I Can’t Drive 55,” Sammy has had 25 platinum albums and has sold more than 60 million albums worldwide. Sammy is also an extremely successful serial entrepreneur and was the first celebrity to create his own tequila brand which he sold more than 20 years ago for nearly $100 million. He is also devoted to giving back and is a generous philanthropist. But who was Sammy before fame and fortune? How did he become the successful rock icon and entrepreneur he is today? Sammy’s journey is filled with many challenges, incredible perseverance, a lucky coincidence, and an ability to change. Sammy attributes his success to the lessons he learned about resilience and appreciation while growing up in poverty in Salinas, CA where he often slept in a car with his mom and siblings to get away from his alcoholic father. When Sammy fell in love with music at a Rolling Stones concert at age 14, the scrappy, adaptable young man bought a guitar from Sears and decided he would stop at nothing to pursue his dream of becoming a rock star.In this fascinating episode, Sammy and Randall talk about Sammy’s journey from poverty to the big stage, Sammy’s experience with the bands Montrose and Van Halen, his creativity and marketing abilities in building Cabo Wabo Cantina and Cabo Wabo Tequila, and his dedication to philanthropy and making a difference in local communities.Topics Include: - The odd jobs Sammy had while growing up which taught him the value of a strong work ethic;- Sammy’s first realization about what having money would be like;- Sammy’s first concert experiences and learning to play the guitar;- The lessons Sammy learned from growing up poor;- The ups and downs and experiences of playing with Van Halen for 20 years;- The sale of Cabo Wabo Tequila for nearly $100 million to Gruppo Campari;- His creativity, branding, and marketing tactics used to build the Cabo Wabo brand;- Sammy’s three most important ingredients in the path to excellence;- His ability to finding joy and happiness in the simple things;- The origins of Sammy’s Beach Bar and Grill and the restaurant’s commitment to give back; - And other topics…Sammy Hagar is an American singer-songwriter, musician, and entrepreneur. In the 1970s, Sammy’s career took off with the rock band Montrose, and continued after he launched a successful solo career that included some of the greatest rock anthems ever written with songs like “I Can’t Drive 55,” “Right Now,” and “Why Can’t This be Love.” Sammy was the frontman for Van Halen for nearly 20 years, has had 25 platinum albums, and has sold 60 million records worldwide. He is a Grammy award winner and inductee to the Rock and Roll Hall of Fame. Sammy is also an incredibly talented entrepreneur, starting companies such as Cabo Wabo Tequila, Cabo Wabo Cantina, Sammy’s Beach Bar and Grill, Sammy’s Beach Bar Rum, and Santo Mezquila. He is also a two-time New York Times best-selling author and a dedicated philanthropist. In 2008, Sammy started the Hagar Family Foundation, a private non-profit that focuses on food relief and children’s causes including children with cancer.Coaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Mar 29, 2022 • 1h 38min
Orlando Bravo: Finding Your Niche | E16
The incredible story of Orlando Bravo’s journey from a tuna fishing village in Puerto Rico to the most successful private equity investor in the world, is one of incredibly hard work and a fierce determination to succeed. When Orlando’s childhood dream of becoming a professional tennis player ended, he went to Brown on a tennis scholarship, was terrified he wouldn't succeed, graduated Phi Beta Kappa in the top 2% of his class, and later earned a JD / MBA from Stanford. After not being offered a summer internship position at a prestigious private equity firm and graduating from Stanford without a job, Orlando made 100 cold calls to potential employers, one of whom was Carl Thoma who is considered one of the founders and pioneers of private equity. It was here that Orlando put himself on the map. After making a series of poor acquisitions of technology companies that survived the dot.com bust in 2010-2011, he pivoted and began investing in software companies. His first deal was the acquisition of Prophet 21, a product distribution software provider based in San Diego where he worked for five days in the garage of the company’s founder before going forward with the deal. The investment made a 4x return and earned Orlando a seat at the table, and by the age of 30 Orlando became a partner in the firm. Since its founding, Thomas Bravo has completed more than 350 acquisitions worth nearly $155 billion, and presently oversees a portfolio of 50 software companies that generate $21 billion in annual revenue and employs more than 72,000 people around the world. In this inspirational episode, Randall and Orlando discuss Orlando’s journey from tennis to higher education, why he focuses on investing in well-established software companies instead of startups, the importance of learning from investment mistakes and other failures, and why he believes the next generation is always better than the previous one.Topics Include: - Lessons about work ethic learned from his parents and grandfather- How “soft landings” and limiting pressure can build environments where people thrive- Why Orlando prefers cold calling to introductions- How the dot-com bubble influenced his investment strategy - The story of the Profit 21 acquisition- How he made a $9 billion profit in 18 months by buying and selling Ellie Mae- How to attract and retain top talent- The place cryptocurrency in our society- The value of preparation- Mentorship- The importance of philanthropy and his incredible efforts after Hurricane Maria, and what he’s doing to help Puerto Rico and young entrepreneurs there- And other topics… Orlando Bravo is the Founder and Managing Partner of Thoma Bravo, a private equity firm with a focus on software and technology that has been rated the top-performing private equity firm in the world. Orlando is an incredibly generous philanthropist and serves as the Founder and Chairman of the Bravo Family Foundation whose mission is to provide access and opportunities to young adults in Puerto Rico. He has committed over $100 million to the Foundation’s Rising Entrepreneurs Program (REP), a program that promotes entrepreneurship in Puerto Rico. Resources Mentioned: Memos from the Chairman by Alan GreenbergCoaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn