Episodes
-
Amy Porterfield had a dream job working with Tony Robbins, one of the world’s top motivational speakers and business strategists. But deep down, she wanted to be her own boss. During a high-level meeting, she realized she was on the wrong side of the table, watching entrepreneurs build wealth instead of becoming one. With no plan, no clients, and no backup, she left corporate life and built a $100 million online business. In this episode, Amy joins Ilana to share how she overcame imposter syndrome, depression, and anxiety to create a balanced life and the mindset shift that took her from employee to multimillion-dollar entrepreneur.
Amy Porterfield is an online marketing expert, entrepreneur, and bestselling author. She has helped thousands of people break free from traditional 9-to-5 jobs and create financial freedom through entrepreneurship.
In this episode, Ilana and Amy will discuss:
(00:00) Introduction
(01:44) Entrepreneurial Lessons from Childhood
(03:35) Landing a Dream Job with Tony Robbins
(07:46) The Three Biggest Lessons from Working with Tony
(11:51) The Moment That Made Her Quit Corporate
(14:48) Overcoming Imposter Syndrome and Depression
(21:24) Finding Strength in Support Systems
(24:24) How to Transition from Employee to Entrepreneur
(27:32) Navigating the First Two Years in Business
(29:21) Redefining Success to Avoid Burnout
(35:20) Handling Hate and Criticism Online
(38:19) Shifting Your Money Mindset to Scale Faster
(43:35) Creating and Selling Profitable Digital Courses
(46:05) Why Mistakes Are the Key to Growth
Amy Porterfield is an online marketing expert, entrepreneur, and bestselling author. She runs a $100 million company teaching entrepreneurs how to create, market, and sell profitable digital courses. As the host of the Online Marketing Made Easy podcast and bestselling author of Two Weeks Notice, she has helped thousands of people break free from traditional 9-to-5 jobs and create financial freedom through entrepreneurship.
Connect with Amy:
Amy’s Website: amyporterfield.com
Amy’s LinkedIn: linkedin.com/in/amyporterfield
Resources Mentioned:
Amy’s Book, Two Weeks Notice: Find the Courage to Quit Your Job, Make More Money, Work Where You Want, and Change the World: https://www.amazon.com/Two-Weeks-Notice-Courage-Change/dp/1401969879
The Let Them Theory: A Life-Changing Tool That Millions of People Can't Stop Talking About by Mel Robbins: https://www.amazon.com/Let-Them-Theory-Life-Changing-Millions/dp/1401971369
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 -
Norma Kamali built a business with her then-husband, but he controlled the money and decisions and even rehired the woman she had fired. Realizing the partnership was toxic, she walked away with just $98. No company. No safety net. No guarantees. Most people would have crumbled, but Norma reinvented herself. Within months, her bold designs took off, attracting lifelong, high-profile clients. Five decades later, she is still shaping the industry. In this episode, she joins Ilana to share how she overcame early setbacks, left a toxic partnership, and built lasting success.
Norma Kamali is a fashion designer and entrepreneur known for her bold, timeless designs. Her designs have been worn by stars across generations. Always innovating, she recently explored AI, training a model to create designs in her signature style.
In this episode, Ilana and Norma will discuss:
(00:00) Introduction
(01:49) Finding Her Path as a Child
(04:09) How Her Mother Shaped Her Ambition
(10:33) Discovering a Passion for Drawing
(14:41) Pursuing Fashion Illustration
(16:42) Walking Out of a Humiliating Job Interview
(18:32) How an Airline Job Led Her into Fashion
(23:22) Starting a Fashion Business Accidentally
(30:48) Marriage, Business, and a Toxic Partnership
(36:42) Leaving Her Company with Just $98
(41:50) Rebuilding as Omo Norma Kamali
(46:06) Styling Celebrities Across Generations
(49:52) Mastering Sales and Its Challenges
(54:42) Norma’s Secret to Navigating Fear in Business
(56:32) Embracing AI and Future Plans
(01:00:28) The Mindset That Turns Failure into Fuel
Norma Kamali is a fashion designer and entrepreneur known for her bold, timeless designs. Over the past five decades, she has helped shape fashion, from popularizing shoulder pads in the 1980s to creating iconic pieces like the sleeping bag coat, high-heeled sneakers, and Farrah Fawcett’s red swimsuit. Her designs have been worn by stars across generations. Always innovating, she recently explored AI, training a model to create designs in her signature style.
Connect with Norma:
Norma’s Website: normakamali.com
Norma’s LinkedIn: linkedin.com/company/norma-kamali-inc./
Norma’s Instagram: instagram.com/normakamali
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 -
Episodes manquant?
-
Ilana Golan knows what it means to start over. After losing her job, startup, and investment all at once, she faced uncertainty head-on. Instead of settling for what she was merely good at, she uncovered her ‘zone of genius’ and focused on what she truly excelled at. Through this journey, she rebuilt her career and created a system to help others do the same. In this episode, Ilana shares how to identify your strengths, stand out, and take control of your reputation.
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
(00:34) Identifying Your Unique Value
(01:15) The Four Categories of Skills
(03:27) How to Discover Your Strengths
(04:38) Leveraging Feedback to Find Your Genius
(05:44) Creating a 'Brag Bank' to Build Authority
(06:34) How Challenges Reveal Your True Strengths
(07:10) Using Your Strengths to Build Your Brand
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 36 years old, Rajiv Shah got a call from Hillary Clinton. Days later, he was running USAID. Less than a week into the job, a massive earthquake leveled Haiti. He had no time to prepare. He had to act. That was one of many high-stakes bets in his career. From launching a $5 billion vaccine program with the Gates Foundation to fighting Ebola and leading global humanitarian efforts, he has tackled some of the world’s biggest challenges and won. In this episode, Rajiv joins Ilana to share how he makes big bets, leads through crisis, and asks the right questions to solve impossible challenges.
Dr. Rajiv Shah is a physician, economist, global development leader, author, and President of the Rockefeller Foundation. Known for achieving the impossible to drive global change, he led U.S. responses to crises like the Haiti earthquake and Ebola outbreak as USAID Administrator..
In this episode, Ilana and Rajiv will discuss:
(00:00) Introduction
(01:55) From Immigrant Kid to Global Leader
(04:02) A Life-Changing Service Trip to India
(07:00) Leaving Medical School for Politics
(11:22) Joining the Gates Foundation
(13:10) A 'Big Bet' That Saved 20 Million Lives
(15:00) How Strategic Questions Unlock Big Solutions
(19:31) Leading USAID Through Haiti’s Earthquake
(26:38) Earning Obama and Biden’s Trust in a Crisis
(30:22) Fighting the Ebola Outbreak with Military Support
(33:22) Tackling Energy Poverty at the Rockefeller Foundation
(38:54) Why Real Change Requires Big Risks
(44:38) How Great Leaders Balance Change and Stability
(47:08) The Power of Connection and Shared Values
Dr. Rajiv Shah is a physician, economist, global development leader, author, and President of the Rockefeller Foundation. Known for achieving the impossible to drive global change, he led U.S. responses to crises like the Haiti earthquake and Ebola outbreak as USAID Administrator. Previously, at the Gates Foundation, he helped expand childhood vaccinations and led health and agriculture initiatives. His book, Big Bets, explores bold solutions to the world’s toughest challenges.
Connect with Rajiv:
Rajiv’s Website: rockefellerfoundation.org/
Rajiv’s LinkedIn: linkedin.com/in/drrajivjshah/
Resources Mentioned:
Rajiv’s Book, Big Bets: How Large-Scale Change Really Happens: https://www.amazon.com/Big-Bets-Large-Scale-Change-Happens/dp/1668004380
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 -
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 -
Trent Shelton hit a low point after his NFL career ended, leaving him lost and questioning his purpose. Tragedy struck when his best friend, overwhelmed by his own struggles, took his life. The loss shook Trent to his core. Determined to honor his friend’s memory and empower others facing similar challenges, Trent picked up his phone and began sharing raw, heartfelt videos. These eventually evolved into RehabTime, a global movement helping millions turn pain into purpose. In this episode, Trent joins Ilana to share powerful lessons on resilience, protecting your peace, rediscovering purpose, and the five words that transform pain into power.
Trent Shelton is a former professional football player, motivational speaker, and author. After his career in the NFL ended, he founded RehabTime, a platform dedicated to personal growth and empowerment.
In this episode, Ilana and Trent will discuss:
(00:00) Introduction
(01:47) The Influence of Supportive Parents
(03:41) Lessons from Playing College Football
(04:58) Losing His Identity at the End of His NFL Career
(08:17) How to Rediscover Purpose After Losing It All
(10:43) Becoming a Father and Finding New Motivation
(12:24) The Tragedy That Inspired RehabTime
(16:14) Starting a Movement With Just a Phone
(19:32) The True Power of Authenticity
(21:34) How RehabTime Became a Global Movement
(23:38) Five Words That Shift Pain Into Power
(27:37) Protecting Your Peace in a Chaotic World
(30:30) Finding Balance Between Peace and Hustle
(34:43) Ignoring Doubters and Staying True to Your Path
Trent Shelton is a former professional football player, motivational speaker, and author. After his career in the NFL ended, he founded RehabTime, a platform dedicated to personal growth and empowerment. Through his raw, impactful messages, Trent has inspired millions to overcome adversity and unlock their potential. His book, Protect Your Peace, offers practical guidance on healing, self-discovery, and becoming the best version of yourself.
Connect with Trent:
Trent’s Website: trentshelton.com
Trent’s Instagram: instagram.com/trentshelton/
Resources Mentioned:
Trent’s Book, Protect Your Peace: Nine Unapologetic Principles for Thriving in a Chaotic World: https://www.amazon.com/Protect-Your-Peace-Unapologetic-Principles/dp/1401973167
Trent’s Book, The Greatest You: Face Reality, Release Negativity, and Live Your Purpose: https://www.amazon.com/Greatest-You-Reality-Release-Negativity/dp/1400207932
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 -
John Graham went from being a shy, anxious kid to becoming a three-time USA Memory Champion and performing before 400 million viewers in China. Despite these achievements, John faced severe anxiety and daily panic attacks, which led him to confront and release suppressed emotions. Today, he has transformed his struggles into strength, helping others unlock their true potential. In this episode, John joins Ilana to share how he overcame severe anxiety through unconventional methods, the importance of facing your triggers, and the powerful connection between emotional healing and peak performance.
John Graham is a three-time USA Memory Champion, memory improvement expert, and a featured competitor on FOX’s Superhuman. He holds achievements like memorizing 229 names and faces in 15 minutes. As a speaker and coach, John helps others overcome anxiety, build confidence, and reach their potential.
In this episode, Ilana and John will discuss:
(00:00) Introduction
(01:42) Discovering the Power of Memory
(05:03) Mastering Memory Techniques as a Shy, Anxious Kid
(08:46) Finding Fulfillment Beyond Accomplishments
(11:53) Beating Crippling Anxiety in Memory Competitions
(14:30) Building Mental Toughness Under Pressure
(19:11) Competing Before 400 Million Viewers in China
(22:51) The Hidden Cost of Suppressing Emotions
(27:47) Getting to the Root Cause of Anxiety
(37:53) The Secret to Remembering Names and Faces
(39:54) How to Memorize Faster
(41:44) Using Visual Stories to Ace Tests
(43:00) Releasing Anxiety by Leaning Into the Pain
John Graham is a three-time USA Memory Champion, memory improvement expert, and a featured competitor on FOX’s Superhuman. Known for his ability to memorize extraordinary amounts of information, John has captivated audiences worldwide. He holds achievements like memorizing 229 names and faces in 15 minutes. As a speaker and coach, John helps others overcome anxiety, build confidence, and reach their potential.
Connect with John:
John’s Website: memoryjohn.com/about/
John’s LinkedIn: linkedin.com/in/memoryjohn
Resources Mentioned:
Moonwalking with Einstein: The Art and Science of Remembering Everything by Joshua Foer: https://www.amazon.com/Moonwalking-Einstein-Science-Remembering-Everything/dp/0143120530
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 his parents’ divorce, Topaz Adizes discovered the power of connection through the camera. His drive to explore human connection led him to become a filmmaker. From filmmaking to his work with The Skin Deep, Topaz focuses on creating real, vulnerable conversations in a digital world. His viral documentary The And shows how shared space and honest dialogue can deepen relationships. In this episode, Topaz joins Ilana to discuss the art of asking questions that strengthen relationships and how to create space for hard but empowering conversations.
Topaz Adizes is an award-winning writer, director, experience design architect, and the founder and executive director of The Skin Deep, an experience design studio. He has earned an Emmy for new documentary approaches, and two World Press Photo awards for immersive storytelling.
In this episode, Ilana and Topaz will discuss:
(00:00) Introduction
(01:37) Finding Purpose in His Parents' Divorce
(04:27) The Lasting Impact of Divorce on Relationships
(07:16) Why The And Documentary Went Viral
(11:12) How Great Questions Create Great Relationships
(12:28) Ways to Craft Questions That Yield Results
(14:19) The Cost of Avoiding Difficult Conversations
(18:16) Creating Space for Hard, Scary Conversations
(24:16) Training Your Mind to Ask Empowering Questions
(26:55) Crafting Questions That Drive Clarity and Growth
(32:10) Five Questioning Strategies to Deepen Relationships
(38:54) A Raw Father-Son Conversation on YouTube
(41:47) Aligning Passion and Profit for Sustainable Growth
(52:01) The Life Topaz Wishes He Had Embraced Sooner
Topaz Adizes is an award-winning writer, director, experience design architect, and the founder and executive director of The Skin Deep, an experience design studio. He has earned an Emmy for new documentary approaches, and two World Press Photo awards for immersive storytelling. Topaz's work has been showcased at Cannes, Sundance, and SXSW, and featured in The New Yorker, Vanity Fair, and The New York Times.
Connect with Topaz:
Topaz’s Website: https://www.topazadizes.com/
Topaz’s LinkedIn: linkedin.com/in/topazadizes/
Resources Mentioned:
Topaz’s Book, 12 Questions for Love: A Guide to Intimate Conversations and Deeper Relationships: https://www.amazon.com/12-Questions-Love-Conversations-Relationships/dp/1632174901
The And Documentary: https://www.imdb.com/title/tt4439128/
The Skin Deep YouTube: https://www.youtube.com/c/TheSkinDeep
The Unexpected Legacy of Divorce by Julia M. Lewis: https://www.amazon.com/Unexpected-Legacy-Divorce-Landmark-Study/dp/0786886161
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 -
Matt Higgins grew up in abject poverty, caring for his sick mother at just 9 years old. At age 16, he dropped out of high school to focus on financial growth, eventually earning his GED and getting into college. While balancing work, life, and caregiving, he lost his mother unexpectedly on the day he began a new job. Despite these challenges, among others, Matt co-founded a private investment firm, RSE Ventures, appeared as a guest investor on Shark Tank, and developed military drones for the U.S. Army. In this episode, Matt joins Ilana to share the many struggles that shaped his refusal to quit and the power of taking bold, fearless steps toward achieving your goals.
Matt Higgins is an entrepreneur, author, guest investor on ABC's Shark Tank, and co-founder of RSE Ventures, a private investment firm. He advocates for entrepreneurship and innovation, often speaking on leadership, investment, and a success mindset.
In this episode, Ilana and Matt will discuss:
(00:00) Introduction
(01:56) Growing Up in Abject Poverty
(06:13) Having to Become an Adult Too Soon
(08:13) Quitting High School to Make Money
(14:01) Earning His GED and Getting Into College
(16:34) Managing a Career and Supporting a Sick Parent
(19:34) Losing His Mother Without a Final Goodbye
(23:11) Turning Every Job Into a Step Toward Your Dream
(25:14) Rebuilding Life After Testicular Cancer
(28:30) The Secret Behind Matt’s Iconic Book Quotes
(35:04) Beating Self-Doubt to Become a Shark on Shark Tank
(41:30) How “Burning the Boats” Drives Fearless Moves
(46:54) Lessons from Failure and the Refusal to Die
(52:16) Developing Military Drones for the U.S. Army
(56:04) Living Without the Fear of Judgment or Death
Matt Higgins is an entrepreneur, author, guest investor on ABC's Shark Tank, and co-founder of RSE Ventures, a private investment firm. With a career spanning sports, media, and technology, he has played a pivotal role in transforming brands such as The Miami Dolphins and Sky Group. Matt is the author of the Wall Street Journal bestseller Burn the Boats. He advocates for entrepreneurship and innovation, often speaking on leadership, investment, and a success mindset.
Connect with Matt:
Matt’s Website: https://rseventures.com/
Matt’s LinkedIn: linkedin.com/in/matt-higgins-rse
Resources Mentioned:
Matt’s Book, Burn the Boats: Toss Plan B Overboard and Unleash Your Full Potential: https://www.amazon.com/Burn-Boats-Overboard-Unleash-Potential/dp/006308886X
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 -
It seemed like all was lost after Nicholas “Nick” Stone was cut from three different teams during his sports career. However, he used this setback to transition into finance, eventually founding Bluestone Lane, a successful coffee shop chain. Despite having never made coffee before, his love for the premium coffee culture of his home country, Australia, inspired him to transform the U.S. coffee experience into a more personalized one. In this episode, Nick joins Ilana to share how he transformed an 87% revenue loss into an opportunity for innovation and reinvention, emphasizing his commitment to community, human connection, and exceptional quality.
Nicholas Stone is an Australian businessman, former professional athlete, and banker. He is also the founder and CEO of Bluestone Lane, a premium coffee and café brand inspired by Australia’s rich coffee culture.
In this episode, Ilana and Nick will discuss:
(00:00) Introduction
(01:50) The Resilience That Took Him from Sports to Finance
(07:13) Moving from Australia to Chase a New York Dream
(09:15) Building Connections and Networks in New York
(12:23) Founding Bluestone to Fix U.S. Coffee Culture
(14:59) Keeping His Day Job to Launch Bluestone Lane
(20:35) Creating a People-First Café Experience
(23:09) Tough Lessons on Expanding Too Soon
(25:52) Filtering Advice in the Early Stages of Business
(27:33) The Hidden Challenges of Running a Café Chain
(32:33) How Nick Manages Founder Stress with Support
(37:35) Surviving the Pandemic After Losing 87% of Revenue
(45:02) Why Bluestone Sticks to Quality Over Shortcuts
(48:40) Nick's Focus on Values and Promoting Internally
(50:21) The Power of Celebrating Small Wins in Business
Nicholas Stone is an Australian businessman, former professional athlete, and banker. He is also the founder and CEO of Bluestone Lane, a premium coffee and café brand inspired by Australia’s rich coffee culture. Under his leadership, Bluestone Lane has become the fastest-growing premium café brand in the U.S., raising $70 million in venture capital and expanding to over 65 locations. Nick has been featured in The New York Times, CNBC, Bloomberg, the Wall Street Journal, and more.
Connect with Nick:
Nick’s Website: https://bluestonelane.com/
Nick’s LinkedIn: linkedin.com/in/nicholas-stone-49465767
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 losing seven elections in college, Bill George realized that leadership is about building relationships and helping others grow. Personal losses, including the deaths of his mother and fiancée, taught him resilience and the value of purpose. Though on track to become CEO at Honeywell, Bill chose a more fulfilling path at Medtronic, focusing on the company’s mission to restore lives. In this episode, Bill takes Ilana through his leadership philosophies and shares lessons on building relationships, leading with values, and prioritizing purpose over profits, which were pivotal in driving Medtronic's success.
Bill George is a renowned thought leader, educator, and bestselling author, best known for his transformative leadership as CEO of Medtronic. A strong advocate for values-driven leadership, Bill emphasizes leading with purpose, values, relationships, and heart.
In this episode, Ilana and Bill will discuss:
(00:00) Introduction
(04:30) Learning Leadership Lessons Through Early Failures
(06:50) Losing His Mother and Fiancée Suddenly
(09:22) Turning Tough Moments Into Learning Opportunities
(11:37) The Value of Building Relationships
(13:16) Choosing Purpose Over the CEO Path at Honeywell
(16:18) Measuring Impact by Lives Restored at Medtronic
(21:42) Mentoring Across Different Generations for Free
(24:20) Making a Risky Move to Challenge the FDA
(26:47) Leadership Beyond Just Making Profits
(33:18) Using Data and Intuition to Make Bold Decisions
(35:48) Remarkable Leaders Who Followed Their ‘True North’
(44:21) Balancing Leadership, Family, and Self-Care
(48:56) Bill's Advice for Emerging Leaders
Bill George is a renowned thought leader, educator, and bestselling author, best known for his transformative leadership as CEO of Medtronic. A strong advocate for values-driven leadership, Bill emphasizes leading with purpose, values, relationships, and heart. Earlier in his career, he held senior executive roles at Honeywell and Litton Industries. He is the author of True North and serves as an Executive Fellow at Harvard Business School, where he taught for nearly 20 years, shaping the next generation of leaders
Connect with Bill:
Bill’s Website: http://www.billgeorge.org/
Bill’s LinkedIn: linkedin.com/in/williamwgeorge/
Resources Mentioned:
Bill’s Book, True North: Discover Your Authentic Leadership: https://www.amazon.com/True-North-Discover-Authentic-Leadership/dp/0787987514
Bill’s Book, True North, Emerging Leader Edition: Leading Authentically in Today's Workplace:
https://www.amazon.com/True-North-Emerging-Leader-Authentically-ebook/dp/B0BBSWCVT4
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 - Montre plus
