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, ...
How to Win Investors: The Brutal Truth About Raising Capital | Elizabeth Yin
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 Investing
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 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
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56:02
LeapCon 2025: Ilana Golan on Taking Bold Risks That Lead to Unstoppable Career Growth
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 Academy
Ilana Golan is an entrepreneur, board director, and investor in over 100 companies. As the founder of Leap Academy, she helps professionals navigate career transitions, leadership, and personal branding. She has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Ilana is also a sought-after keynote speaker and has been featured on Yahoo Finance, Fox, NBC, and more.
Connect with Ilana:
Ilana’s Website: ilanagolan.com
Ilana’s LinkedIn: linkedin.com/in/ilanagolan
Resources Mentioned:
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
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35:15
Emmy Nominee, Bastiano Ferrari: From Broke and Sleeping on Beanbags to Building Hollywood Success
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 Innovations
Bastiano 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
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38:44
Former Obama Foundation President: How to Lead Through the Toughest Moments | David Simas
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 Responsibility
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, 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
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55:51
Amy Porterfield: I Quit a Prestigious Job with Tony Robbins and Built a $100M Business
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
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.
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