Leap Academy with Ilana Golan

In one of our most popular 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

On our most replayed episode, Gary ‘Vee’ Vaynerchuk talks about how being scrappy wasn’t just a choice for him; it was his only way forward. After years of growing his family’s wine business, he was left with nothing of his own. With no money to rent an office or hire employees, Gary leveraged his grit, relationships, and opportunities to launch VaynerMedia. Overcoming the financial, mental, and emotional hurdles of entrepreneurship, he built his company into a multi-million-dollar media empire. In this episode, Gary joins Ilana to reveal the mindset and strategies you need to overcome obstacles and build your own multi-million-dollar business.

Gary Vaynerchuk, famously known as GaryVee, is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early.

In this episode, Ilana and Gary will discuss:

(00:00) Introduction 

(01:40) VaynerMedia's Scrappy Beginnings

(06:56) Why Businesses Fail Financially

(10:01) Navigating Tough Business Days

(17:21) The Risk of Over-Transparency in Leadership

(19:44) Dealing with Failure and Public Ridicule

(22:10) GaryVee’s Dream of Owning the New York Jets

(26:06) The Role of DNA and Accountability in Success

(28:35) Finding Joy in Entrepreneurship

(31:02) How to Build a Personal Brand as an Employee

(32:30) Empowering Employees with Honest Feedback

(34:27) Embracing Change and Executing Relentlessly

Gary Vaynerchuk, famously known as GaryVee, is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. He is a prolific angel investor with early investments in companies like Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase, and Uber. 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 

Resources Mentioned:

Gary’s Book, Day Trading Attention: How to Actually Build Brand and Sales in the New Social Media World: ⁠https://www.amazon.com/Day-Trading-Attention-Actually-Social/dp/0063317591⁠ 

GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire: ⁠https://podcasts.apple.com/us/podcast/garyvee-from-earning-%242-an-hour-to-running-a/id1701718200?i=1000689595539⁠ 

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

As a kid struggling with ADHD and financial instability, David watched his family nearly lose their home before taking a door-to-door sales job as a broke college student. He was terrible at it at first, but instead of quitting, he became obsessed with learning sales, systems, and business psychology. That mindset helped him build and sell four companies, scale across 5,000 cities in 34 states, and turn one of the world’s most overlooked industries into a $500 million empire. In this episode, David joins Ilana to share the sales lessons, leadership principles, and mindset shifts that helped him build through rejection, near-bankruptcy moments, and why some of the biggest opportunities today are hiding inside “boring” businesses.

David Royce is the chairman of AP Environmental, one of North America's largest residential pest control companies. Starting from door-to-door sales as a college student, he built and sold four companies, reaching over 5,000 cities across 34 states and a $500M valuation at exit.

In this episode, Ilana and David will discuss:

(00:00) Introduction

(04:58) The “Problem Kid” Who Built a $500M Business  

(13:22) Sales Skills Every Entrepreneur Needs

(17:06) Taking the Leap to Build His Own Business

(21:17) Surviving the Early Business Chaos

(29:02) Biggest Lessons from Tony Hsieh

(33:52) How Scaling Exposes Every Weakness

(37:45) The Failure That Forced David to Evolve

(41:39) How Bankruptcy Changed His Definition of Success

(45:34) “Boring” Businesses That Build Real Wealth

(54:37) The Power of Risks in Creating Bigger Lives

David Royce is a four-time exit founder and chairman of AP Environmental, one of North America's largest residential pest control companies. Starting from door-to-door sales, he built and sold four companies over the course of his career. His third company sold for a reported $135M, and his fourth, AP Environmental, reached a reported $500M valuation at exit, operating in over 5,000 cities across 34 states. 

Connect with David:

David’s LinkedIn: linkedin.com/in/david-royce-22539425  

Aptive Website: aptivepestcontrol.com/  

Resources Mentioned:

Delivering Happiness - A Path to Profits, Passion, and Purpose by Tony Hsieh: https://www.amazon.in/dp/145550890X. 

Leap Academy:

Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. 

Check out our free training today at https://bit.ly/leap--free-training

Mark Tluszcz had the career most people would chase: a top consulting job, rapid success, and a clear path forward. But eight years in, he made a move very few would dare to make. He left his high-paying job to start his own firm, faced hundreds of rejections while raising capital, and built Mangrove Capital from scratch. That same contrarian mindset led him to back companies others overlooked, becoming an early investor in Skype and later Chairman of Wix. In this episode, Mark joins Ilana to share how he invested early in Skype, spotted Wix before it became a global company, and why he turned down a $400 million acquisition offer. He also breaks down how to build conviction, embrace rejection, and find opportunities where others see risk.

Mark Tluszcz is the co-founder and CEO of Mangrove Capital Partners and chairman of Wix, one of the world's leading website-building platforms. He is widely regarded as one of Europe's most influential venture capitalists, known for his early investments in Skype and Wix.

In this episode, Ilana and Mark will discuss:

(00:00) Introduction

(05:36) Growing Up Across Multiple Cultures

(09:09) Leaving Corporate Consulting to Build His Own Firm

(13:58) Building Mangrove Capital During the Internet Boom

(20:54) How to Keep Going After Hundreds of Nos

(27:25) How Skype Evolved Beyond Music

(36:47) Staying Humble After a Massive Win

(43:08) Discovering Wix and Rethinking Venture Capital

(50:33) Turning Down a $400M Deal: The Wix Story

(57:41) Building Resilience Through Honest Conversations

(01:01:14) Spotting the Next Wave of AI Opportunity

(01:10:57) The Founder Mindset That Actually Lasts

Mark Tluszcz is the co-founder and CEO of Mangrove Capital Partners, a Luxembourg-based venture capital firm he built from the ground up after leaving Arthur Andersen in 2000. He was one of the first investors in Skype, where Mangrove’s $2 million investment reportedly returned $200 million, and he has served as chairman of Wix, where an $8 million investment reportedly yielded $700 million.

Connect with Mark:

X: x.com/marktluszcz 

Mark’s Instagram:  instagram.com/marktluszcz/ 

Mark’s LinkedIn: linkedin.com/in/mark-tluszcz-a024b51 

Mark’s Blog: https://www.daretodreambeyond.com/ 

Leap Academy:

Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. 

Check out our free training today at https://bit.ly/leap--free-training

John Paul DeJoria grew up with no connections, no money, and no roadmap. He sold encyclopedias door-to-door despite constant rejection, got fired from three consecutive jobs, and lived out of his car while raising his young son. Then, with just $700, he launched John Paul Mitchell Systems and built it into a billion-dollar haircare company. That same relentless spirit later helped him turn Patrón Tequila into one of the most recognized spirit brands in the world. In this episode, John Paul joins Ilana to share what it truly takes to build something from nothing, why rejection is just redirection, and why success unshared is failure.

John Paul DeJoria is a self-made billionaire, entrepreneur, and the visionary co-founder behind John Paul Mitchell Systems and Patrón Tequila. Beyond his iconic business achievements, he is a passionate philanthropist dedicated to creating a positive global impact.

In this episode, Ilana and John Paul will discuss:

(00:00) Introduction

(03:40) Growing Up in Foster Care as an Immigrant Kid

(11:20) The Navy Lessons That Shaped His Leadership

(15:23) Making It Through Sudden Homelessness

(23:23) How Getting Fired Led Him to Start Paul Mitchell

(28:22) How He Made Billions With Only $700 

(40:50) Letting Go of Fear, Failure, and Yesterday’s Mistakes

(46:14) Growing Patrón Against the Odds

(53:30) What Meeting Gaddafi Taught Him About Kindness

(56:57) The New AI Platform That’s Making Entrepreneurship Easier

(01:00:15) Why Happiness, Health, and Family Matter Most

John Paul DeJoria is a self-made billionaire, philanthropist, and co-founder of John Paul Mitchell Systems, the world’s largest privately owned salon haircare brand. He also co-founded The Patrón Spirits Company, growing it from zero distribution to over 3.5 million cases annually before its landmark sale. His upcoming memoir, Success Unshared Is Failure, details his extraordinary journey and his conviction that giving back is essential.

Connect with John Paul:

John Paul’s Website: peacelovehappinessfoundation.org

John Paul Mitchell Systems: https://www.paulmitchell.com

Resources Mentioned:

John Paul’s Book, Success Unshared is Failure: https://www.amazon.com/Success-Unshared-Failure-John-DeJoria/dp/B0FSTBMCJ8

Leap Academy:

Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. 

Check out our free training today at https://bit.ly/leap--free-training