Grant Cardone: Reinventing at 50 to Build a Multi-Billion Dollar Business from Rock Bottom

Ilana Golan watched others rise while she felt stuck in her career. Her identity was built around job titles and companies until she lost it all. Realizing she had spent years growing businesses but not herself, she invested tens of thousands to master public speaking and build her brand. That decision led to high-paying keynotes, advisory roles, board seats, and even the sale of her tech startup. In this episode, Ilana shares how she went from feeling stuck to unlocking massive opportunities through public speaking and personal branding. Ilana Golan is an entrepreneur, board director, and investor in over 100 companies. As the founder of Leap Academy, she helps professionals navigate career transitions, leadership, and personal branding. In this episode, Ilana will discuss: (00:00) Introduction  (00:14) Her Career Wake-Up Call (00:54) The Power of Public Speaking (01:52) Why Investing in Your Brand Pays Off (02:50) Transforming Your Career with Personal Branding Ilana Golan is an entrepreneur, board director, and investor in over 100 companies. As the founder of Leap Academy, she helps professionals navigate career transitions, leadership, and personal branding. She has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Ilana is also a sought-after keynote speaker and has been featured on Yahoo Finance, Fox, NBC, and more. Connect with Ilana: Ilana’s Website: ilanagolan.com  Ilana’s LinkedIn: linkedin.com/in/ilanagolan  Resources Mentioned: Free Training: https://training.leapacademy.com/pass  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

At just 10 years old, Grant Cardone lost his father. This moment flipped his world upside down. He spiraled into teenage addiction, hitting rock bottom in his mid-twenties. Determined to change, he got clean, mastered sales, and began building wealth. It wasn’t until his fifties, during the 2008 financial crisis, that he realized survival meant growing bigger. That’s when he went all in. He scaled Cardone Capital, grew his brand, and turned his hard-earned lessons into a multi-billion-dollar business. In this episode, Grant joins Ilana to discuss overcoming adversity, embracing reinvention, managing fear in high-stakes investments, and his strategies for building wealth and a powerful network. Grant Cardone is a serial entrepreneur, equity fund manager, real estate investor, and bestselling author. A global authority on sales, investing, and personal development, he influences millions through his books, events, and online content. In this episode, Ilana and Grant will discuss: (00:00) Introduction  (01:48) Reinventing After Facing a Career Crisis (03:01) Childhood Struggles After Losing His Father (05:52) Battling Addiction and Near-Death Experiences (08:17) Stuck in a Sales Job but Crushing It (10:35) The Birth of the 10X Movement (15:02) Building a Highly Influential Brand at Age 52 (17:38) The Secret to Never Getting Laid Off (20:13) Taking a Loan to Launch His Real Estate Empire (21:33) Navigating Fear, Doubt, and High-Stakes Risks (27:04) The $58 Million Loan Call That Shook Him (30:35) Turning Small Investments into Billion-Dollar Deals (35:00) The Future of the 10X Growth Conference (38:54) Grant’s Real Estate-Bitcoin Investment Strategy (40:19) The Most Overlooked Shortcut to Success Grant Cardone is a serial entrepreneur, equity fund manager, real estate investor, and bestselling author. He is the founder of Cardone Capital, a real estate investment firm managing billions in assets. He also created the 10X movement, which includes the 10X Growth Conference, the largest business conference in the U.S. A global authority on sales, investing, and personal development, he influences millions through his books, events, and online content. Connect with Grant: Grant’s Website: https://grantcardone.com  Grant’s LinkedIn: linkedin.com/in/grantcardone  Resources Mentioned: Grant’s Book, The 10X Rule: The Only Difference Between Success and Failure: https://www.amazon.com/10X-Rule-Difference-Between-Success-ebook/dp/B004X75OES  Grant’s Book, Sell or Be Sold: How to Get Your Way in Business and in Life: https://www.amazon.com/Sell-Be-Sold-Your-Business/dp/B00JV3YVHU  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

The Leap Academy Podcast with Ilana Golan is all about honest and inspiring conversations about what it really takes to leap to bigger things, amazing careers, and craft the life you want. Stories and tips you won't find anywhere else. Ilana speaks with some of the world's most influential people, experts, and thinkers who created incredible careers, had a massive impact, built a reputation, and lived extraordinary lives. Together, we discover the untold truths, the emotions, and important lessons that enabled them to reinvent themselves & leap. We take our audience on a journey that will not only inspire but also teach concrete lessons on how to leap careers: fast-track to leadership, jump to entrepreneurship, build a personal brand, portfolio career, and much more.

Tiffany Williams started as a part-time receptionist with the Golden State Warriors, just looking to get her foot in the door. Two weeks later, she was offered a full-time role and quickly rose into business development. In 2015, she led the planning of the Warriors’ NBA Championship parade, an experience that fueled her drive for bigger opportunities. Her work ethic caught the attention of Steph Curry, who personally reached out and brought her on to help build his business empire at Thirty Ink. In this episode, Tiffany shares with Ilana how hunger, resilience, and seizing every opportunity took her from the front desk to the front lines of brand building. Tiffany Williams is the Chief Operating Officer at Thirty Ink, the off-court business arm of NBA superstar Steph Curry. She is a key force behind Steph’s brand, media ventures, and philanthropic impact. In this episode, Ilana and Tiffany will discuss: (00:00) Introduction  (01:38) The Hustle to Get into Sports Business (03:46) Taking a Receptionist Job to Break in (07:17) Organizing the Warriors’ 2015 Championship Parade (10:26) Earning Trust and Getting Recruited by Steph Curry (14:05)  Shaping Steph’s Brand and Community Impact (15:31) Overcoming Imposter Syndrome at the Top (17:24) Learning from a Network of Mentors (21:18) How Thirty Ink Elevates the Underrepresented (24:09) Staying Driven When Success Feels Slow (25:51) The Key to Navigating Career Setbacks Tiffany Williams is the Chief Operating Officer at Thirty Ink, the off-court business arm of NBA superstar Steph Curry. She began her career as a receptionist with the Golden State Warriors, quickly rising to lead major projects like the team’s 2015 Championship Parade. Tiffany is a key force behind Steph’s brand, media ventures, and philanthropic impact, and is known for her strategic execution, resilience, and leadership across sports, business, and community. Connect with Tiffany: Tiffany’s LinkedIn: linkedin.com/in/tiffany-williams-2518742/  Resources Mentioned: Thirty Ink Website: https://www.thirtyink.com/  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Where most people give up after a handful of rejections, Seth Godin got rejected 800 times by editors before finally making a big break. For him, every “no” was a clue. He adapted and mastered the system, and soon, the same editors who dismissed him were calling him first. His success wasn’t luck or passion. It was built by showing up, iterating, and playing the long game. In this episode, Seth joins Ilana to reveal why most people quit before they succeed, how to market ideas people want, and why smart strategy, not passion, drives real success. Seth Godin is an entrepreneur, bestselling author, and marketing expert widely recognized for his groundbreaking ideas on marketing, leadership, and business innovation. He inspires individuals and businesses to make a difference by being creative, authentic, and impactful. In this episode, Ilana and Seth will discuss: (00:00) Introduction  (01:34) Startup Failures and Early Struggles (02:48) From 800 Rejections to Breakthrough (04:34) Turning Rejections into Strategic Insights (06:25) How to Lead Change Amid Resistance (09:23) Why Commitment Beats Passion (11:12) The Dip: Knowing When to Stay or Quit (14:31) How to Create Value in Niche Spaces (19:32) Building Success with Constant Iteration (23:33) Strategies for Earning Your Worth (27:06) Building Brand Reputation Through Consistency (31:55) The Chocolate Bar Marketing Strategy (34:34) Embracing Failure as Part of the Journey Seth Godin is an entrepreneur, bestselling author, and marketing expert widely recognized for his groundbreaking ideas on marketing, leadership, and business innovation. He is the author of over 20 best-selling books, including Purple Cow, and This Is Marketing. Seth inspires individuals and businesses to make a difference by being creative, authentic, and impactful. Connect with Seth: Seth’s Website: https://www.sethgodin.com/  Seth’s LinkedIn: linkedin.com/in/sethgodin/ Resources Mentioned: Seth’s Blog: https://seths.blog/  Seth’s Book, The Dip: A Little Book That Teaches You When to Quit (and When to Stick) https://www.amazon.com/Dip-Little-Book-Teaches-Stick/dp/1591841666 Seth’s Book, This Is Strategy: Make Better Plans: https://www.amazon.com/This-Strategy-Better-Elevate-Community/dp/B0D47T8S7N  Seth’s Book, This Is Marketing: You Can't Be Seen Until You Learn to See: https://www.amazon.com/This-Marketing-Cant-Until-Learn/dp/0525540830/  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Gil Shwed built Check Point into a $20 billion cybersecurity giant, but it all began with a flaw he spotted as a programmer in the Israeli military. Tasked with connecting classified networks, he uncovered a vulnerability, and the idea for a firewall was born. A few years later, he launched Check Point, betting on internet security before the web even existed. At 26 years old, he took the company public despite his doubts. Three decades later, he stepped down as CEO, having reshaped cybersecurity forever. In this episode, Gil joins Ilana to share how he built a problem-solving mindset, landed game-changing deals, scaled a startup from nothing, and led a multibillion-dollar company for 30 years. Gil Shwed is the co-founder and Executive Chairman of Check Point Software Technologies, one of Israel's largest tech companies and the world’s top cybersecurity firm. He was the CEO for 30 years, the longest of any CEO on Nasdaq, and still helps guide the company today. In this episode, Ilana and Gil will discuss: (00:00) Introduction  (01:32) Early Programming Passion (02:17) Gaining Problem-Solving Skills in the Military (06:25) The Security Flaw That Inspired Check Point (07:45) How Early Jobs Shaped His Path to Check Point (12:26) Realizing the Need for Firewalls Ahead of Time (15:12) Raising Capital Without VC Funding (17:47) Convincing Companies to Adopt Firewalls (21:06) Closing a $1M Deal After 100 Days of Hustle (28:34) Why Gil Reluctantly Took Check Point Public (33:03) The Secret to His Leadership Success (36:03) Navigating Market Changes and Stress (41:08) How Gil Stays Ahead in Business (44:05) Stepping Down as CEO After 30 Years (49:00) Minimizing Risks in Business (52:13) Building a Startup That Lasts Gil Shwed is the co-founder and Executive Chairman of Check Point Software Technologies, one of Israel's largest tech companies and the world’s top cybersecurity firm. He saw early on how important cybersecurity would be as the world became more connected, helping Check Point grow into a leader in the industry. Gil was the CEO for 30 years, the longest of any CEO on Nasdaq, and still helps guide the company today. Connect with Gil: Gil’s Website: https://www.checkpoint.com/  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

After the crash of his company, Michael Hyatt was determined to rise again. Returning to his old publishing firm, he took on a failing division and turned it into the most profitable. His hard work paid off with a massive bonus check. But when he rushed home to celebrate, his wife was in tears. He had put his all in at work, at the cost of his family. That moment changed everything. Instead of choosing between work and life, he found a way to win at both. Now, through Full Focus, he helps others do the same. In this episode, Michael joins Ilana to share how he rebuilt after failure, set healthy work boundaries, and redefined success to thrive in work and life. Michael Hyatt is a bestselling author, leadership expert, and founder of Full Focus, helping leaders succeed without sacrificing their personal lives. Through his books and coaching, he helps high achievers lead with vision, set boundaries, and create lasting impact. In this episode, Ilana and Michael will discuss: (00:00) Introduction  (01:49) How Philosophy Shaped His Business Mindset (03:21) Why His Fast-Growing Company Crashed (06:40) The Key to Overcoming Business Failure (11:44) Succeeding at Work, Losing at Home (14:49) Balancing Family, Work, and Life’s Demands (23:36) Rest as the Key to Peak Performance (28:24) The Power of Peer Support in Leadership (31:07) Becoming CEO and Navigating Crisis (36:43) From CEO to Building a Personal Brand (42:39) Why Retirement Was Never an Option (43:58) Building a Personal Brand That Lasts (46:42) Finding Purpose Beyond Work (49:46) Creating a Legacy That Matters (52:07) Overcoming Personal Challenges and Trauma (54:27) The Importance of Therapy and Seeking Help Michael Hyatt is a bestselling author, leadership expert, and founder of Full Focus, helping leaders succeed without sacrificing their personal lives. As former CEO of Thomas Nelson, he led its turnaround and acquisition by HarperCollins. Realizing success shouldn’t come at the cost of family, he developed the Double Win philosophy, proving you don’t have to choose between work and life. Through his books and coaching, he helps high achievers lead with vision, set boundaries, and create lasting impact. Connect with Michael: Michael’s Website: https://fullfocus.co  Michael’s LinkedIn: linkedin.com/in/michaelhyatt  Resources Mentioned: Michael’s Book, Free to Focus: A Total Productivity System to Achieve More by Doing Less: https://www.amazon.com/Free-Focus-Productivity-System-Achieve-ebook/dp/B07F3DM7C1  Michael’s Book, Platform: Get Noticed in a Noisy World: https://www.amazon.com/Platform-Get-Noticed-Noisy-World/dp/140023803X  The Power of Full Engagement: Managing Energy, Not Time, Is the Key to High Performance and Personal Renewal by Jim Loehr: https://www.amazon.com/Power-Full-Engagement-Managing-Performance/dp/0743226755  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

At 29 years old, Brandon Dawson was on top of the world. He had taken his company public, stood on the American Stock Exchange floor, and rang the bell. He felt unstoppable until his private equity investors sold his company against his will. Most people would have quit, but Brandon learned from this setback, cracked the code to scaling, and went on to build and sell his next company for $151 million. Today, he helps business owners do the same through Cardone Ventures, a $500 million business he co-founded. In this episode, Brandon joins Ilana to share insights on scaling a business against all odds, why 97% of businesses fail, and how to be in the top 3%. Brandon Dawson is an entrepreneur, scaling expert, and co-founder of Cardone Ventures. With over 30 years of experience, he helps businesses scale using data-driven strategies, navigate breakpoints, and avoid common pitfalls. In this episode, Ilana and Brandon will discuss: (00:00) Introduction  (01:47) From College Dropout to Top Sales Performer (03:45) Selling Everything to Start a Business (05:48) Getting Kicked Out of His Own Company (09:08) Surviving the Early Years of Entrepreneurship  (12:31) Turning Leadership Failures into Billion-Dollar Lessons (16:08) The $151 Million Exit That Made Employees Millions (21:57) Scaling a Family Business Without the Chaos (25:22) Staying Unstoppable in the Face of Hate (32:12) Why Most Entrepreneurs Fail and How to Avoid It (39:41) Making Data-Driven Decisions in Business Brandon Dawson is an entrepreneur, scaling expert, and co-founder of Cardone Ventures. As CEO of Sonus Corporation, he grew it to over 1,400 locations and raised $58 million before investors took control and sold the company against his wishes. He later founded Audigy Group, scaling it from $500,000 to $35 million before selling it for $151 million. With over 30 years of experience, Brandon helps businesses scale using data-driven strategies, navigate breakpoints, and avoid common pitfalls. Connect with Brandon: Brandon’s Website: https://bdawson.com Brandon’s LinkedIn: linkedin.com/in/brandonmdawson  Resources Mentioned: Brandon’s Book, Nine-Figure Mindset: How to Go from Zero to Over $100 Million in Net Worth: https://www.amazon.com/Nine-Figure-Mindset-Zero-Million-Worth/dp/B0C8G8CTQC  The 5 Levels of Leadership: Proven Steps to Maximize Your Potential by John C. Maxwell: https://www.amazon.com/Levels-Leadership-Proven-Maximize-Potential/dp/1599953633  The 21 Irrefutable Laws of Leadership: Follow Them and People Will Follow You by John C. Maxwell: https://www.amazon.com/21-Irrefutable-Laws-Leadership-Anniversary/dp/0785288376  Good to Great: Why Some Companies Make the Leap...And Others Don't by Jim Collins: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996  Great by Choice: Uncertainty, Chaos, and Luck--Why Some Thrive Despite Them All by Jim Collins, Morten T. Hansen: http://amazon.com/Great-Choice-Uncertainty-Luck-Why-Despite/dp/0062120999  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

After Craig Newmark moved to San Franciso in 1995, he had a simple idea: a mailing list to share local events with friends. It wasn’t fancy and certainly wasn’t meant to change the world. However, as the list grew, people began calling it “Craigslist,” unknowingly naming what would become a billion-dollar digital marketplace. In this episode, Craig joins Ilana to share his journey, from creating Craigslist without VC funding to stepping down as CEO to focus on customer service. He also discusses how his moral compass continues to shape his work, including his mission in cybersecurity and his support for veterans and military families. Craig Newmark is an internet entrepreneur, philanthropist, and the founder of Craigslist, the online classified ads platform that transformed how people buy, sell, and connect. As a philanthropist, he supports causes related to veterans, journalism, tech ethics, and cybersecurity.  In this episode, Ilana and Craig will discuss: (00:00) Introduction  (02:01) The People and Moments That Shaped His Values (03:30) Navigating Social Skills as a Nerd (05:05) How a Simple Mailing List Led to Craigslist (08:23) Why Craig Rejected Billion-Dollar VC Funding (11:07) The Surprising Story Behind the Name Craigslist (12:46) His Slow but Steady Approach to Scaling (14:31) Fighting Fraud, and Dirty Tricks in Business (16:37) The Strategy Behind Growing Without Funding (19:02) Craig’s Pivot from CEO to Customer Service Rep (22:36) How Veterans Inspired His Cybersecurity Focus (29:51) His Pigeon Rescue Mission Craig Newmark is an internet entrepreneur, philanthropist, and the founder of Craigslist, the online classified ads platform that transformed how people buy, sell, and connect. As a philanthropist, he supports causes related to veterans, journalism, tech ethics, and cybersecurity. Craig also serves on the boards of several nonprofits and was named one of Time magazine’s 100 most influential people. Connect with Craig: Craig’s Website: craignewmarkphilanthropies.org  Craig’s LinkedIn: linkedin.com/in/craignewmark  Resources Mentioned: Craigslist Website: craigslist.org Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Gary ‘Vee’ Vaynerchuk was born to be an entrepreneur. At six years old, he was already running a lemonade stand like a boss, later flipping baseball cards for cash. By age 14, he had made thousands when his father put him to work in the family liquor store for $2 an hour. He hated it, but years later, he rebranded the business and scaled it from $4 million to $60 million. Realizing he didn’t own a piece of it, Gary walked away with nothing and started over. Now, as the founder of multiple ventures, including VaynerMedia, and an early investor in Facebook and Twitter, he knows that real failure isn’t losing, it’s never taking the shot. In this episode, Gary joins Ilana to break down the pressure, sacrifice, and resilience needed to win in business and life. GaryVee is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. As a prolific investor, he made early bets on major tech giants, including Facebook and Twitter. In this episode, Ilana and Gary will discuss: (00:00) Introduction  (02:24) Hardwired for Entrepreneurship As a Kid (05:34) From the Soviet Union to the American Dream (07:22) Why Building Wealth Doesn’t Guarantee Joy (11:15) Getting Forced Into the Liquor Business at Age 14 (13:18) Scaling the Family Business from $4M to $60M (17:14) Discovering the Internet and Betting Big on It (21:10) The Power of Personal Branding (26:13) Building Resilience Against Online Hate (29:24) Why Gary Would Rather Fail Than Regret or Blame (32:21) The Harsh Realities of Entrepreneurship (39:49) Humility, Not Titles as the Key to Lasting Success (43:27) Choosing Optimism Over Fear GaryVee is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. He built his career by transforming his family’s liquor business from $4 million to $60 million before launching multiple ventures of his own. As a prolific investor, he made early bets on major tech giants, including Facebook and Twitter. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early. Connect with Gary: Gary’s Website: garyvaynerchuk.com  Gary’s LinkedIn: linkedin.com/in/garyvaynerchuk  Gary’s Instagram: instagram.com/garyvee  Resources Mentioned: Gary’s Book, Crushing It!: How Great Entrepreneurs Build Their Business and Influence-and How You Can, Too: https://www.amazon.com/Crushing-Great-Entrepreneurs-Business-Influence/dp/0062674676  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training