Leap Academy with Ilana Golan

Guy Kawasaki’s journey from a lower-middle-class neighborhood in Hawaii to becoming a Silicon Valley icon is clear proof of grit and transformation. After working in the jewelry business, he pivoted to tech and joined Apple as Chief Evangelist. There, he played a key role in launching the Macintosh, shaping Apple’s brand, and transforming how technology is marketed. Today, Guy is a venture capitalist, startup advisor, and Chief Evangelist at Canva. In this episode, Guy shares his battle with hearing loss, why passion is overrated, his top sales strategies, and advice for scaling a business as an entrepreneur.Guy Kawasaki is a marketing specialist, bestselling author, venture capitalist, and speaker. As the former Chief Evangelist for Apple, he played a pivotal role in launching the Macintosh and now serves as Chief Evangelist at Canva.In this episode, Ilana and Guy will discuss:(00:00) Introduction (02:11) From Humble Beginnings to Studying at Stanford(06:24) Why Sales Is the Key to Business Success(11:01) Knowing When to Pivot vs. Stick with Your Career(17:26) Transitioning from Jewelry Business to Tech(21:48) Key Lessons from Working with Steve Jobs(24:38) How to Evangelize Great Ideas(26:31) The Promotion That Led Guy to Quit Apple(31:58) The Myth of “Finding Your Passion”(38:26) Building Resilience After Hearing Loss(43:15) Strategies to Scale Your Career and Business(49:33) How to Truly Understand Customers’ NeedsGuy Kawasaki is a marketing specialist, bestselling author, venture capitalist, and speaker. As the former Chief Evangelist for Apple, he played a pivotal role in launching the Macintosh and now serves as Chief Evangelist at Canva. Despite experiencing hearing loss and receiving a cochlear implant, Guy’s passion for sharing ideas remains unwavering. He hosts the Remarkable People podcast and delivers over fifty keynote speeches annually for clients like Apple, Nike, Google, and Microsoft.Connect with Guy:Guy’s Website: guykawasaki.com Guy’s LinkedIn: linkedin.com/in/guykawasakiResources Mentioned:Guy’s Podcast,  Remarkable People: bit.ly/RemarkablePeoplePod Guy’s Book, Think Remarkable: 9 Paths to Transform Your Life and Make a Difference: https://www.amazon.com/Think-Remarkable-Paths-Transform-Difference/dp/139424522X 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

Growing up, Shai Reshef wasn’t the most enthusiastic student, but after earning a master’s degree in Chinese politics, he discovered the transformative power of education. Inspired by a UNESCO report predicting the future lack of access to higher education, Shai decided to act. He sold two businesses, leveraged open-source technology, and partnered with volunteer professors to create University of the People, the world’s first tuition-free, accredited online university. In this episode, Shai joins Ilana to share how the university is empowering over 150,000 students from marginalized communities and offers valuable advice for those seeking to make a meaningful impact.Shai Reshef is the founder and president of University of the People, a nonprofit, tuition-free, accredited online university dedicated to providing accessible higher education to underserved populations across 206 countries.In this episode, Ilana and Shai will discuss:(00:00) Introduction (01:52) The Power of Education in Nation-Building(04:41) Founding the First Online University in Europe(09:08) Creating a Global, Tuition-Free University(16:05) Overcoming Accreditation Challenges(19:34) The Global Impact of the University of the People(26:41) Building a Sustainable Model for Free Education(30:59) How University of the People Screens Students(34:18) Keys to Launching a Meaningful Project(38:18) Balancing Leadership Stress with Team Dynamics(40:33) Success Stories from University of the People(43:41) The Power of Philanthropy and NonprofitsShai Reshef is the founder and president of University of the People, a nonprofit, tuition-free, accredited online university dedicated to providing accessible higher education to underserved populations across 206 countries. Previously, he led Kidum Group, Israel’s largest for-profit educational services company, and chaired KIT eLearning, the first online university in Europe. Recognized for his impact on education, Shai also serves as an adviser to the UN’s Global Alliance for ICT and Development.Connect with Shai:Shai’s LinkedIn: linkedin.com/in/shaireshef Resources Mentioned:University of the People’s Website: www.uopeople.eduLeap 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

Growing up with dyslexia and ADHD, Rosanna Pansino struggled to find her career path. After being fired from every job, she found her calling on YouTube, combining her love for baking with nerdy pop culture. Despite financial struggles, she invested her life savings into building her channel, Nerdy Nummies, which quickly became a sensation. With over 14 million subscribers, bestselling cookbooks, and her own product line, Rosanna turned content creation into a thriving business. In this episode, Rosanna joins Ilana to share how she sustains a long-lasting digital career, navigates platform algorithms, and diversifies her entrepreneurial ventures.Rosanna Pansino is a YouTuber, actress, author, entrepreneur, and baker, best known for her channel Nerdy Nummies, where she creates visually stunning baked goods inspired by pop culture.In this episode, Ilana and Rosanna will discuss:(00:00) Introduction (02:24) Growing up with Dyslexia and ADHD(05:07) Discovering a Passion for Baking(06:51) Lessons from Random Jobs and Failure(10:13) Transitioning from Acting Career to Nerdy Nummies(14:09) Investing Her Savings in YouTube Growth(17:04) How Getting Fired Sparked YouTube Success(25:44) Grief and Mentorship from Susan Wojcicki(31:40) Expanding Beyond YouTube(34:03) Sustaining a Long-Term Digital Career(36:52) Adapting Content to Platform Algorithms(41:24) Balancing Family and Business Partnerships(47:03) How Your Inner Circle Drives SuccessRosanna Pansino is a YouTuber, actress, author, entrepreneur, and baker, best known for her channel Nerdy Nummies, where she creates visually stunning baked goods inspired by pop culture. With over 14 million subscribers, she has become one of the most influential figures in the baking and YouTube communities. Rosanna is the author of two cookbooks, The Nerdy Nummies Cookbook and Baking All Year Round, and hosted the HBO Max series Baketopia.Connect with Rosanna:Rosanna’s Website: rosannapansino.com Rosanna’s YouTube: youtube.com/@RosannaPansino Resources Mentioned:Star Trek: Phoenix - Cloak & Dagger Part I: https://www.imdb.com/title/tt1704271/ Leap Academy:Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time.Check out our free training today at leapacademy.com/training

John Hennessey’s passion for cars began as a child, sitting on his father’s lap as he drove and feeling the thrill of shifting gears. What started as a love for fast cars grew into a pursuit of speed and performance. Despite limited finances, John’s entrepreneurial drive led him to start a car modification business with no formal training. Through trial and error, he founded Hennessey Performance Engineering, known for the Venom F5, the world’s fastest car. In this episode, John shares how passion fueled his success, how he navigates criticism and competition, the role of branding in building a powerful business, and his mission to mentor future engineers through Tuner School.John Hennessy is the founder and CEO of Hennessey Special Vehicles and Hennessey Performance Engineering, known for high-performance, custom-built vehicles. Under his leadership, Hennessey Performance has become a recognized leader in automotive innovation, specializing in speed, power, and precision.In this episode, Ilana and John will discuss:(00:00) Introduction (01:30) Falling in Love With Cars as a Kid(04:51) Lessons from Early Jobs and Entrepreneurship(09:38) Racing Adventures and Early Successes(17:37) Turning His Passion for Cars into a Business(20:09) Leveraging Media Relationships to Build a Brand(29:15) How YouTube Helped Scale His Business(32:58) Overcoming Challenges to Build the Venom F5(38:09) Financial Management and Business Growth(40:46) Embracing Haters as a Sign of Relevance(42:44) Building a Brand on Authenticity and Value(45:13) Training the Next Generation with Tuner School(49:00) Lessons From 35 Years of EntrepreneurshipJohn Hennessy is the founder and CEO of Hennessey Special Vehicles and Hennessey Performance Engineering, known for high-performance, custom-built vehicles. An engineer with a passion for speed, John created the Hennessey Venom F5, a hypercar designed to exceed 300 mph. He also founded Tuner School to train future vehicle engineers and tuners. Under his leadership, Hennessey Performance has become a recognized leader in automotive innovation, specializing in speed, power, and precision.Connect with John:John’s LinkedIn: linkedin.com/in/john-hennessey-9645a0bJohn’s Instagram: instagram.com/john_hennessey_texasResources Mentioned:Hennessey Performance: hennesseyperformance.com Tuner School: https://tunerschool.com Leap Academy:Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time.Check out our free training today at leapacademy.com/training

After quitting her job at Google, Elizabeth Yin took a bold leap into entrepreneurship by founding LaunchBit, an adtech company. Despite facing challenges with fundraising and customer acquisition, LaunchBit was acquired. Drawing on these experiences, Elizabeth joined 500 Startups, where she invested in early-stage companies. As co-founder of Hustle Fund, she now backs startups focused on speed and execution. In this episode, Elizabeth joins Ilana to share the challenges of starting a business, how she evaluates founders to invest in, and the realities of fundraising in the competitive world of venture capital.Elizabeth Yin is a co-founder and General Partner at Hustle Fund, a seed-stage venture capital firm that invests in early-stage startups. She has reviewed over 20,000 startup pitches and assisted numerous portfolio founders in raising hundreds of millions of dollars.In this episode, Ilana and Elizabeth will discuss:(00:00) Introduction (01:39) Falling in Love with Startups in High School(05:32) Adapting to Global Work Cultures(07:25) Leaving Google to Launch Her Startup(13:08) The Challenges of Starting a Business(16:28) How Mentors Shaped Her Startup Journey(18:15) How to Approach Mergers and Acquisitions(21:03) Key Lessons From Investing in 200+ Startups(29:41) Fundraising Realities and Strategies(33:36) The Mission Behind Hustle Fund(35:23) Navigating Stereotypes and Rejection(41:13) How to Decide Whether to Raise Capital(45:16) Handling Identity Shifts as an Entrepreneur(51:14) Building a Network Through Angel InvestingElizabeth Yin is a co-founder and General Partner at Hustle Fund, a seed-stage venture capital firm that invests in early-stage startups. She founded LaunchBit, an adtech company acquired in 2014, and was a partner at 500 Startups, where she invested in seed-stage companies. Elizabeth has reviewed over 20,000 startup pitches and assisted numerous portfolio founders in raising hundreds of millions of dollars.Connect with Elizabeth:Elizabeth’s Website: elizabethyin.com Elizabeth’s LinkedIn: linkedin.com/in/elizabethyin/ Resources Mentioned:Hustle Fund’s Website: hustlefund.vc/ Leap Academy:Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time.Check out our free training today at leapacademy.com/training

After her first startup collapsed, Ilana Golan lost her job, salary, and investment. Feeling like a failure, she spiraled into doubt and uncertainty. But instead of giving up, she made a promise not to be the person who does nothing. That decision led her to reinvent herself and found Leap Academy, a community helping others make bold career shifts. In this 2025 LeapCon, Ilana shares her emotional journey from feeling stuck in her career to becoming an impactful leader. She provides actionable insights for navigating hidden markets, building a personal brand, and growing continuously in your career.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 (02:27) The Power of Dreaming Big(05:06) Breaking Free From Career Stagnation(09:21) Turning Tragedy into Fuel(11:49) The Collapse of Her First Startup(16:06) How to Reinvent Yourself Again and Again(18:12) The Cycle of Ego, Fear, and Growth(21:35) Handling Critics and Naysayers(22:49) Building True Confidence in Business(25:34) How to Open Doors in Hidden Markets(26:36) The Three Levels of Personal Branding(30:11) Learning From Others to Accelerate Growth(31:41) Inspiring Success Stories From Leap AcademyIlana 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:Leap Academy Website: leapacademy.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

Bastiano Ferrari’s journey is one of resilience and perseverance against all odds. At just 11 years old, he faced financial hardship when his father lost everything. Despite his family’s disapproval, he pursued his passion for acting, even when it meant sleeping on beanbags and struggling to eat. But with his mother to care for, Bastiano had to pause acting to launch a tech company that ultimately gave him the financial freedom to return to Hollywood, where he earned an Emmy nomination. In this episode, Bastiano joins Ilana to share how resilience and bold decisions shaped his success in both Hollywood and tech, bridging two seemingly different worlds.Bastiano Ferrari is an Emmy-nominated producer, actor, and entrepreneur. Despite setbacks, Bastiano leveraged his experiences to create a unique portfolio career that spans film, tech, and entrepreneurship.In this episode, Ilana and Bastiano will discuss:(00:00) Introduction (01:20) From Wealth to Hardship as a Child(05:11) Pursuing Acting Despite Family Opposition(06:36) Launching and Selling His Startup(07:38) Balancing a Career in Tech and Film(10:37) Overcoming Challenges Through Resilience(15:28) The Key to Thriving in Adversity(17:43) How to Build Valuable Connections(21:14) Thriving in Multiple Careers Without Burning Out(23:39) Hollywood vs. Tech: The Illusion of Success(28:20) The Power of Big, Scary Dreams(31:29) Why He Has No Regrets About Failure(33:30) New Film Project and AI InnovationsBastiano Ferrari is an Emmy-nominated producer, actor, and entrepreneur. After facing significant financial hardship, he took a break from acting and co-founded a tech startup that was acquired in 2013. Returning to Hollywood, he worked with major stars like Will Smith, earning Emmy nominations along the way. Despite setbacks, Bastiano leveraged his experiences to create a unique portfolio career that spans film, tech, and entrepreneurship.Connect with Bastiano:Bastiano’s Instagram: instagram.com/bastianoferrari Resources Mentioned:Bad Boys for Life: imdb.com/title/tt1502397 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

David Simas grew up in a Portuguese immigrant family in Massachusetts. His mother, who lost two fingers in a factory accident, instilled in him the power of resilience and the importance of community. These lessons shaped his career, from practicing law to advising President Obama on key national issues and eventually leading the Obama Foundation, where he worked with global leaders to promote democracy and address critical global challenges. In this episode, David joins Ilana to share valuable insights on navigating political crises, leading with empathy, and maintaining personal balance during high-stress moments in public service. David Simas is a lawyer, political strategist, and former CEO and president of the Obama Foundation. He served as White House Director of Political Strategy and Outreach during the Obama administration and has held key roles in state and federal government.In this episode, Ilana and David will discuss:(00:00) Introduction (01:53) Growing Up in a Portuguese Immigrant Family(05:10) Family Struggles and Community Support(09:03) How Legal Training Shaped His Perspective(16:57) Transitioning from Law to Politics(19:44) The Call That Led Him to the White House(23:19) Why Obama’s Team Chose David(27:30) Giving the People a Voice in the Oval Office(32:11) How Great Leaders Handle Crisis(36:38) Balancing Humility and Authority in Leadership(40:28) Navigating Political Pressure and Public Scrutiny(51:12) The Power of Personal ResponsibilityDavid Simas is a lawyer, political strategist, and former CEO and president of the Obama Foundation. He served as White House Director of Political Strategy and Outreach during the Obama administration and has held key roles in state and federal government, advising on political engagement and policy strategy. He is currently the Managing Director of Research and Impact at Emerson Collective, where he focuses on democracy, immigration, education, and climate initiatives.Connect with David:David’s LinkedIn: linkedin.com/in/david-simas/ 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

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 GrowthAmy 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/amyporterfieldResources 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 FuelNorma 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