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    Business

    Leap Academy with Ilana Golan

    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, massive impact, built a reputation, and an extraordinary life.

    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. 

    Advertise

    Copyright: © 2024 The Leap Academy with Ilana Golan

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    Latest Episodes:
    Amy Porterfield: Why I Quit My Dream Job to Become an Entrepreneur | EP 89 Jul 07, 2026
    Show notes

    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

    Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.
    Start with a free strategy call: https://itl.ink/leapstrategycall
    🎓 Watch the free masterclass on building multiple income streams: https://itl.ink/leap-webinar
    👇 Like what you see? Comment below and let us know what resonated!
    ---------------
    🎧 PODCAST | Leap Academy with Ilana Golan
    Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
    ▶️ https://www.leapacademy.com/podcast
    ---------------
    📲 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/
    🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek


    GaryVee on Building an Unstoppable Mindset | E115 Jun 30, 2026
    Show notes

    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

    Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.
    Start with a free strategy call: https://itl.ink/leapstrategycall
    🎓 Watch the free masterclass on building multiple income streams: https://itl.ink/leap-webinar
    👇 Like what you see? Comment below and let us know what resonated!
    ---------------
    🎧 PODCAST | Leap Academy with Ilana Golan
    Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
    ▶️ https://www.leapacademy.com/podcast
    ---------------
    📲 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/
    🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek


    From Blue Collar Hustles to Billion Dollar Businesses: The Journey of David Royce Jun 23, 2026
    Show notes

    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

    Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.
    Start with a free strategy call: https://itl.ink/leapstrategycall
    🎓 Watch the free masterclass on building multiple income streams: https://itl.ink/leap-webinar
    👇 Like what you see? Comment below and let us know what resonated!
    ---------------
    🎧 PODCAST | Leap Academy with Ilana Golan
    Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
    ▶️ https://www.leapacademy.com/podcast
    ---------------
    📲 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/
    🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek


    From Skype to Wix: Mark Tluszcz’s Formula for Turning Bold Bets into Billion-Dollar Successes | E163 Jun 16, 2026
    Show notes

    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

    Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.
    Start with a free strategy call: https://itl.ink/leapstrategycall
    🎓 Watch the free masterclass on building multiple income streams: https://itl.ink/leap-webinar
    👇 Like what you see? Comment below and let us know what resonated!
    ---------------
    🎧 PODCAST | Leap Academy with Ilana Golan
    Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
    ▶️ https://www.leapacademy.com/podcast
    ---------------
    📲 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/
    🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek


    Self-Made Billionaire: How John Paul DeJoria Built Paul Mitchell with $700 | E162 Jun 09, 2026
    Show notes

    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

    Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.
    Start with a free strategy call: https://itl.ink/leapstrategycall
    🎓 Watch the free masterclass on building multiple income streams: https://itl.ink/leap-webinar
    👇 Like what you see? Comment below and let us know what resonated!
    ---------------
    🎧 PODCAST | Leap Academy with Ilana Golan
    Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
    ▶️ https://www.leapacademy.com/podcast
    ---------------
    📲 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/
    🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek


    Former WWE President: The Hard Decisions That Built a Global Media Business | George Barrios | E161 Jun 02, 2026
    Show notes

    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

    Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.
    Start with a free strategy call: https://itl.ink/leapstrategycall
    🎓 Watch the free masterclass on building multiple income streams: https://itl.ink/leap-webinar
    👇 Like what you see? Comment below and let us know what resonated!
    ---------------
    🎧 PODCAST | Leap Academy with Ilana Golan
    Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
    ▶️ https://www.leapacademy.com/podcast
    ---------------
    📲 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/
    🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek


    The Lean Startup: Eric Ries Reveals the #1 Mistake New Founders Make | E160 May 26, 2026
    Show notes

    When Eric Ries built his first startup, he believed he had the perfect plan. But when no customers showed up, the business collapsed, exposing a costly truth: being certain does not make you right. That failure forced him to rethink his assumptions and ultimately led him to develop the Lean Startup method, a new way of building companies grounded in testing, learning, and truth. In this episode, Eric chats with Ilana about why most startups fail before they even launch, how to test ideas early to uncover what actually works, and how leaders can build companies that scale without losing their values. Eric Ries is an entrepreneur, author, and startup strategist best known for creating The Lean Startup methodology, a framework that helps founders build businesses through rapid experimentation and continuous iteration. In this episode, Ilana and Eric will discuss: (00:00) Introduction (02:57) How His Childhood Curiosity Led Him to Computers (08:55) Dropping Out of Yale to Chase a Startup Dream (13:01) The Harsh Reality of the Entrepreneurship Fantasy (14:53) Why Silicon Valley Loves Failed Startups (19:37) Building, Scaling, and Leaving IMVU (23:09) Reinventing Your Identity After Loss (27:10) Tuning Out Bad Advice and Hearing What Matters (30:40) Using Negative Feedback to Fuel Growth (39:11) The Groundbreaking Lean Startup Philosophy (46:13) The Worldwide Resistance to Innovation (51:28) The Controversial Idea Behind Incorruptible (57:18) The Entrepreneurial Near-Death Experience Eric Ries is an entrepreneur, author, and thought leader best known for creating the Lean Startup methodology, which transformed how startups and large companies build products. He is the founder of Long-Term Stock Exchange and has advised founders, executives, and organizations around the world on innovation, leadership, and long-term growth. Connect with Eric: Eric’s LinkedIn: linkedin.com/in/eries Eric’s X: x.com/ericries Resources Mentioned: Eric’s Book, The Lean Startup: https://www.amazon.in/dp/0307887898 Eric’s Book, Incorruptible: https://www.incorruptible.co/ Lean Startup Website: leanstartup.co/ 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

    Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.
    Start with a free strategy call: https://itl.ink/leapstrategycall
    🎓 Watch the free masterclass on building multiple income streams: https://itl.ink/leap-webinar
    👇 Like what you see? Comment below and let us know what resonated!
    ---------------
    🎧 PODCAST | Leap Academy with Ilana Golan
    Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
    ▶️ https://www.leapacademy.com/podcast
    ---------------
    📲 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/
    🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek


    Entrepreneur Magazine’s Jason Feifer: How to Build a Career Beyond Your Job Title | E159 May 19, 2026
    Show notes

    Jason Feifer started his career writing about middle school dances at a tiny local newspaper, frustrated and convinced he was capable of more. Stuck in a role that wasn’t moving him forward, he quit, sat in his dumpy apartment next to a graveyard, and began cold-pitching major publications with no connections. That decision transformed his trajectory, eventually leading him to become Editor-in-Chief of Entrepreneur Magazine and a leading voice on career growth and adaptability. In this episode, Jason chats with Ilana about why doing only what’s expected of you slows your growth, how to identify opportunities, and steps to take control of your career in an unpredictable world. Jason Feifer is the Editor-in-Chief of Entrepreneur Magazine, a podcast host, book author, and keynote speaker who helps people build careers and companies they love by sharing lessons from the world's top entrepreneurs and leaders. In this episode, Ilana and Jason will discuss: (00:00) Introduction (03:48) Cold Pitches From a Bedroom Next to a Graveyard (06:41) Developing an ‘Opportunity Set B’ Mindset (09:51) Building Skills Strategically Across Jobs (12:58) Renting a Title vs. Owning Your Name (17:02) The Mission Statement That Survives Any Job Loss (24:22) Why Jason Walked Away From His Biggest Hit (31:51) How to Test Multiple Ventures At Once (34:31) How a Lawsuit Accidentally Built Jason’s Success (40:00) The Danger of Labeling Yourself (47:47) Q&A: How Do You Become More Adaptable? Jason Feifer is the Editor-in-Chief of Entrepreneur Magazine, a role he has held for over 10 years. He is the author of Build for Tomorrow, host of the podcast Help Wanted, and a sought-after keynote speaker who has spoken for companies including Pfizer, Alibaba, Clorox, and more. Jason also advises startups, sits on multiple advisory boards, and writes the weekly newsletter One Thing Better. His work centers on adaptability, personal reinvention, and helping individuals and organizations thrive through change. Connect with Jason Jason’s Website: https://www.jasonfeifer.com Jason’s LinkedIn: linkedin.com/in/jasonfeifer Jason’s Instagram: https://www.instagram.com/heyfeifer/ Resources Mentioned: Jason's Newsletter, One Thing Better: https://www.jasonfeifer.com⁠ Jason’s Book, Build for Tomorrow: An Action Plan for Embracing Change, Adapting Fast, and Future-Proofing Your Career: https://www.amazon.com/dp/059323538X 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

    Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.
    Start with a free strategy call: https://itl.ink/leapstrategycall
    🎓 Watch the free masterclass on building multiple income streams: https://itl.ink/leap-webinar
    👇 Like what you see? Comment below and let us know what resonated!
    ---------------
    🎧 PODCAST | Leap Academy with Ilana Golan
    Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
    ▶️ https://www.leapacademy.com/podcast
    ---------------
    📲 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/
    🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek


    Tim Draper: How I Spot Billion-Dollar Companies Before Anyone Else | E158 May 12, 2026
    Show notes

    Tim Draper didn’t become a legendary investor with billions in his account overnight; he started by taking a $6 million loan to launch his first venture fund, knowing failure was a real possibility. That decision didn’t just shape his career; it laid the foundation for backing some of the biggest companies in the world, including Hotmail, Skype, Tesla, and more. In this episode, Tim joins Ilana to break down how to spot world-changing ideas before they make sense, why most people miss their biggest opportunities, and how listening to your gut can be more powerful than logic alone. He shares the lessons behind massive wins like Hotmail, painful misses like Netflix, and the mindset required to navigate uncertainty, fear, and reinvention. Tim Draper is a third-generation venture capitalist, founder of Draper University, and one of Silicon Valley's most legendary investors. He is a lifelong advocate for entrepreneurship, innovation, and the next generation of world-changing founders. In this episode, Ilana and Tim will discuss: (00:00) Introduction (04:11) Early Lessons on Money, Risk, and Capitalism (08:43) Leaving Home at 13 and Learning to Figure It Out (11:48) Venture Capital Roots and Family Background (14:17) Taking a $6 Million Loan and Betting on Himself (17:14) Spotting Billion-Dollar Companies Before Anyone Else (20:11) The Viral Growth Strategy Behind Hotmail (23:26) How Skype Changed Global Communication Forever (29:18) Navigating the Dot-Com Crash (34:13) Will AI and Crypto Follow the Same Boom Cycle? (35:55) The Power of Listening to Your Gut as an Entrepreneur (46:59) Q&A: How Do I Know What to Invest In? Tim Draper is a third-generation venture capitalist and founder of Draper University. He backed world-changing companies, including Hotmail, Skype, Tesla, SpaceX, Coinbase, and Robinhood. Known for spotting transformative trends before the mainstream, he's also a passionate advocate for entrepreneurship education, cryptocurrency, and celebrating innovation. His show Meet the Drapers reaches roughly 300 million people globally. Connect with Tim Tim’s Website: https://timothydraper.com/ Tim’s LinkedIn: https://www.linkedin.com/in/timothydraper/ Tim’s Instagram: https://www.instagram.com/timdraper/ Resources Mentioned: Tim’s Book, How to be the Startup Hero - A Guide and Textbook for Entrepreneurs and Aspiring Entrepreneurs: https://www.amazon.com/How-Startup-Hero-Textbook-Entrepreneurs/dp/1973585340/ref=cm_cr_arp_d_product_top?ie=UTF8 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

    Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.
    Start with a free strategy call: https://itl.ink/leapstrategycall
    🎓 Watch the free masterclass on building multiple income streams: https://itl.ink/leap-webinar
    👇 Like what you see? Comment below and let us know what resonated!
    ---------------
    🎧 PODCAST | Leap Academy with Ilana Golan
    Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
    ▶️ https://www.leapacademy.com/podcast
    ---------------
    📲 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/
    🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek


    Kickstarter Co-Founder: How Yancey Strickler Built a $7B Platform That Transformed Crowdfunding | E157 May 05, 2026
    Show notes

    When Yancey Strickler moved to New York, he was broke, freelancing for $50, and chasing a writing career. Little did he know, his gift for building on the internet would soon change the world of crowdfunding. A chance encounter with a friend and a half-baked idea about crowd-funded concert tickets led to the founding of Kickstarter, a platform that has raised over $7 billion for creative projects worldwide. In this episode, Yancey joins Ilana to discuss his journey from freelancing on a shoestring budget to building a billion-dollar platform and what it took to survive the hardest moments. He also explains his bold plan to help artists participate in capitalism. Yancey Strickler is the co-founder and former CEO of Kickstarter, the platform that raised over $7 billion for more than 200,000 creative projects. He now runs Metalabel, a studio building tools for creative cooperation. In this episode, Ilana and Yancey will discuss: (00:00) Introduction (03:11) From Music Households to Manhattan Bylines (06:28) The Side Project That Changed Everything (13:34) The Ladder Vouch System That Launched Kickstarter (18:57) Why Showing Up as an Open Box Wins Every Room (26:31) The Day Two Projects Hit a Million Dollars at Once (33:40) The New Definition of Work in the Age of AI (36:28) Building the Legal Blueprint for the Artist Economy (43:09) Why the Private Internet Is Where the Real World Lives (49:38) Q&A: How to Open Doors to New Connections Yancey Strickler is a writer, serial entrepreneur, and the co-founder of Kickstarter, the global crowdfunding platform that has raised billions for creative projects. He's the author of This Could Be Our Future and The Dark Forest Anthology of the Internet and the co-host of the New Creative Era podcast. Before Kickstarter, Yancey was a music critic for outlets like Pitchfork and Spin. Today, he leads two bold projects: A Corp, a legislative effort to provide artists with real economic infrastructure, and DFOs, a platform reimagining the private internet. Connect with Yancey Yancey’s Website: https://www.ystrickler.com Yancey’s LinkedIn: https://www.linkedin.com/in/yancey-strickler-486b4557/ Yancey’s Instagram: https://www.instagram.com/ystrickler/ Yancey’s X: https://x.com/ystrickler Resources Mentioned: Yancey’s Books, This Could Be Our Future: A Manifesto for a More Generous World: https://www.amazon.com/This-Could-Our-Future-Manifesto/dp/0525560823 The Dark Forest Anthology of the Internet: https://www.amazon.com/Dark-Forest-Anthology-Internet/dp/B0D14NN1DN On the Creative Life: Conversations Toward a New Creative Era: https://squad.metalabel.com/onthecreativelife?ref=ystrickler.com&variantId=1 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

    Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.
    Start with a free strategy call: https://itl.ink/leapstrategycall
    🎓 Watch the free masterclass on building multiple income streams: https://itl.ink/leap-webinar
    👇 Like what you see? Comment below and let us know what resonated!
    ---------------
    🎧 PODCAST | Leap Academy with Ilana Golan
    Inspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.
    ▶️ https://www.leapacademy.com/podcast
    ---------------
    📲 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/
    🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek


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