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

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