Christina Tosi didn’t have a clear five-year plan when she graduated from college. She tried different majors, worked odd jobs, and kept searching for the thing that felt like hers. Baking became the answer she could not ignore. With relentless persistence, she went from a hostess stand to New York restaurant kitchens, proving herself one dessert at a time. That same drive eventually turned a tiny laundromat space into Milk Bar, the dessert empire known for bold flavors, nostalgic treats, and joyful care packages shipped across the country. In this episode, Christina joins Ilana to share how experimentation leads to clarity, why failure is essential to mastery, and what it really takes to build a business rooted in creativity, community, and joy. Christina Tosi is the founder and CEO of Milk Bar, the iconic dessert brand known for its bold, nostalgic treats like the Compost Cookie and cereal milk soft serve. She is a two-time James Beard Award winner and New York Times bestselling author.

In this episode, Ilana and Christina will discuss:

(00:00) Introduction

(05:53) How Childhood Baking Sparked a Career

(10:04) Testing Different Paths Until One Felt Right

(17:56) The Embarrassing Failure That Fueled Her

(22:04) Finding Mentors and Moving to New York

(28:10) The Simple Networking Move That Opened Doors

(31:17) The Cookie That Put Milk Bar on the Map

(38:00) Turning Failure Into Fuel for Growth

(45:04) Building Milk Bar in a Tiny Laundromat

(49:47) Pushing Through Criticism, Burnout, and COVID

(1:03:10) The Shift from Pastry Chef to CEO

(1:08:11) Why Discomfort Can Become Your Edge

(1:16:43) Betting on Yourself Before You Feel Ready

Christina Tosi is the founder and CEO of Milk Bar, a nationally beloved dessert brand with locations across the U.S. She is a two-time James Beard Award winner, TED speaker, and New York Times bestselling author of seven cookbooks. Christina also created Bake Club, a free online baking community launched during COVID that continues to bring bakers together around the world.

Connect with Christina:

Website: christinatosi.com/ 

Christina’s LinkedIn: linkedin.com/in/christina-tosi  

Christina’s Instagram: instagram.com/christinatosi/ 

Christina’s YouTube: youtube.com/christinatosi 

Resources Mentioned:Bake Club: bakeclub.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

📲 Connect with Ilana:

What does it really take to solve impossible problems?

In this episode of Leap Academy with Ilana Golan, Ilana sits down with Astro Teller, CEO of Google X (Alphabet's Moonshot Factory), to uncover the mindset, leadership principles, and innovation frameworks behind some of the world's most groundbreaking technologies—including Waymo, Wing, and Google Brain.

Astro shares why the biggest breakthroughs begin with embracing failure, how Google X celebrates shutting down projects that aren't working, and why successful innovators focus on solving the hardest problem first instead of chasing easy wins.

From reinventing careers to building billion-dollar ideas, this conversation is packed with practical lessons on taking smarter risks, overcoming fear, and creating a process that leads to extraordinary results.

Whether you're an entrepreneur, leader, or simply looking to future-proof your career, this episode will challenge the way you think about success, innovation, and what's possible.

00:00 Introduction

Dr. Astro Teller is the CEO of Google X, Alphabet's Moonshot Factory, where he leads teams creating breakthrough technologies designed to solve some of humanity's biggest challenges.

Since joining Google, Astro has helped launch world-changing innovations including Waymo, Wing, Google Brain, and Tapestry, while developing Google's unique approach to moonshot thinking and breakthrough innovation.

Before Google, Astro was a successful entrepreneur, scientist, inventor, Stanford faculty member, and author. Today, he is recognized as one of the world's foremost voices on innovation, leadership, and the future of technology.

Connect with Astro

Google X (Alphabet's Moonshot Factory)
https://x.company

Astro Teller – Google X Profile
https://x.company/astro-teller

Astro Teller on LinkedIn
https://www.linkedin.com/in/astroteller

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

📲 Connect with Ilana:

Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy

LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/

Instagram ▶️ https://www.instagram.com/ilanagolanleap

Website ▶️ https://www.leapacademy.com/

At 16, his grandmother fled Kraków after the Nazis killed her father, worked a New York factory floor beside her mother, and applied to every medical school in the state three years running before one finally said yes — then told her second-grade grandson that education is the only thing nobody can ever take away from him.Years later, David Rogier quit his venture capital job with no idea what he wanted to build, and his boss wrote him a check for $500,000 and told him to go think of something; the dark, formless year that followed became MasterClass, whose holding company still carries his grandmother's nickname. Launch day brought so few sales that he went home and cried, and by day four it was obvious he had a real business on his hands. In this conversation, David breaks down how he got Hollywood's biggest names to say yes, why he believes degrees and résumés are quickly becoming worthless, and the three kinds of jobs he thinks will actually survive AI.

David Rogier is the founder and CEO of MasterClass, the platform that put instruction from Martin Scorsese, Christina Aguilera, Steph Curry, and dozens of other world-class practitioners into the hands of millions of learners. He built it from a single $500,000 check and has since launched MasterClass Executive, an AI-native alternative to the traditional MBA created in collaboration with OpenAI and the University of Chicago Booth School of Business.

IN THIS EPISODE, ILANA AND DAVID WILL DISCUSS:

(00:00) Introduction

(01:34) The Grandmother Who Survived Kraków and Became a Doctor

(05:39) Stuttering, Teasing, and Parents Who Raised the Bar

(07:15) Quitting His Job and Getting Handed a $500,000 Check

(08:48) The Dark Year: What Happens When You Have No Constraints

(12:58) The Three Things That Had to Be True for MasterClass to Work

(14:33) The Lost Art of Opening Doors and Influencing People

(19:46) Launch Day: No Calls, Almost No Sales, and a Lot of Tears

(21:18) What Scorsese, Steph Curry, and Christina Aguilera Do Differently

(23:53) Why “Hire Great People and Get Out of Their Way” Is Terrible Advice

(27:28) The AI Study That Compressed 18 Months of School Into 18 Hours

(34:16) The Skills That Matter Now: Learning Velocity, Execution, People

(39:28) The Three Types of Jobs That Survive AI

(44:39) Burning the Corporate Ladder: Rebuilding the MBA for $2,500(49:16) What He'd Tell His Younger Self

(51:52) Q&A: My Network Feels Crowded — How Do I Get Real Introductions?

CONNECT WITH DAVID ROGIER

David's Company Website: https://www.masterclass.com

David's LinkedIn: https://www.linkedin.com/in/drogier/

RESOURCES MENTIONED

MasterClass: https://www.masterclass.com

Chris Voss's MasterClass on Negotiation: https://www.masterclass.com/classes/chris-voss-teaches-the-art-of-negotiation

LEAP Episode with Chris Voss: https://podcasts.apple.com/us/podcast/leap-academy-with-ilana-golan/id1701718200?i=1000673141824

LEAP Episode with Tom Bilyeu: Tom Bilyeu: https://www.youtube.com/watch?v=rZ4EGDsKudk

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

📲 Connect with Ilana:

Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy

LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/

Instagram ▶️ https://www.instagram.com/ilanagolanleap

Website ▶️ https://www.leapacademy.com/

Revisiting one of our most-downloaded episodes, Tom Bilyeu shares his powerful journey from self-doubt to self-mastery. His early years were shaped by fear of failure, a lack of direction, and doubts from those around him. After struggling to break into the film industry, he joined a startup with the goal of getting rich, but found himself unhappy and in a strained marriage. Taking a leap of faith, Tom walked away from millions to pursue something more meaningful. This gave rise to Quest Nutrition, a billion-dollar company creating nutritious, great-tasting products. Yet, for Tom, wealth was never the endgame. He launched Impact Theory, a media company designed to impact lives positively. In this episode, Tom shares with Ilana the key moments that shaped his career, the philosophies that drive him, and how he defines true success.

Tom Bilyeu is a billion-dollar entrepreneur, motivational speaker, co-founder of Quest Nutrition, and founder of Impact Theory. Through his content, he inspires millions by sharing tips on overcoming self-doubt, developing the right mindset, and building resilience for success.

In this episode, Ilana and Tom discuss:

(01:15) Introduction
(01:43) Facing Doubts and Rejection
(04:21) How Neuroscience Changed His Mindset
(06:28) Why People Struggle to Make Progress
(07:59) Learning the Power of Discipline in Film School
(12:46) Tom’s Guide to Finding Your Next Step
(15:25) Walking Away from $2 Million to Save His Marriage
(17:14) Building Quest Nutrition with the Right Team
(22:00) Why Tom Launched Quest Nutrition
(24:37) The Key to Surviving Entrepreneurship
(26:19) Strategies for Thriving in Competitive Markets
(30:20) Solving What Others Say Can't Be Done
(31:16) Conquering Fear Through Hard Work
(36:20) The Journey from Quest to Impact Theory
(40:15) Using Entertainment to Inspire Young Minds
(45:24) Lessons from Childhood that Built Tom’s Resilience
(48:06) Two Beliefs to Unlock Your Potential
(49:44) Letting Go of Ego to Grow

Connect with Tom:

Tom’s Website: https://tombilyeu.com
Tom’s YouTube: youtube.com/c/TomBilyeu
Tom’s Twitch: www.twitch.tv/tombilyeu

Leap Academy:

Ready to make the LEAP in your career? There is a NEW way for professionals to advance their careers and make 5–6 figures of extra income in record time.

Check out our free training today at leapacademy.com/training

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

Despite his high intelligence, George Barrios nearly flunked out of both high school and college, drifting without discipline or direction. Realizing talent alone wouldn’t build the future he wanted, he cleaned up his act, became obsessive about preparation, and built a reputation for solving hard problems others avoided. That approach helped him rise through HBO and Time Warner before transforming WWE into a global media powerhouse. In this episode, George joins Ilana to share the habits that accelerated his career, the tough leadership decisions behind WWE’s growth, and the mindset shifts that helped him reinvent himself under pressure.

George Barrios is the former Co-President and CFO of WWE, where he helped transform the company into a global entertainment business. He is the founder of ISOS Capital, an investment and advisory firm focused on sports, media, and technology.

In this episode, Ilana and George will discuss:

(00:00) Introduction

(08:48) When Talent Turned Into Self-Sabotage

(13:12) The Turning Point: Meeting His Wife at UConn

(15:49) Fake It Till You Make It: Learning on the Job 

(23:17) Creating Opportunities After Rejection

(33:31) Driving Digital Growth at The New York Times

(39:38) Making Painful Decisions Under Pressure

(44:14) Transforming WWE into a Global Media Business

(50:35) The Fallout With Vince McMahon and WWE Exit

(59:27) Writing His Book and Sharing Hard Lessons

(01:05:52) Q&A: How Do I Open Doors in a Crowded Market?

George Barrios is a former Fortune 500 executive and the founder of ISOS Capital, an investment firm focused on global opportunities in sports, media, and technology. He previously served as Co-President and CFO of WWE and held leadership roles at The New York Times, HBO, and Praxair, building a track record in strategy, operations, and financial leadership. His new book, Sometimes Wrong but Never in Doubt, shares the lessons behind his unconventional path to success.

Connect with George:

LinkedIn: linkedin.com/in/georgebarrios/ 

Resources Mentioned:

George’s Book, Sometimes Wrong but Never in Doubt: How a Cuban Kid from Queens Transformed WWE: https://www.amazon.com/Sometimes-Wrong-but-Never-Doubt-ebook/dp/B0G4N4T9XV

The World is Flat: The Globalized World in the Twenty-First Century by Thomas Friedman: https://www.amazon.in/dp/0141034890 

Tony Khan: Building AEW into a Billion-Dollar Brand and Competing with Wrestling Giants: www.youtube.com/watch?v=Tqqfg-ysj0M 

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