Leap Academy
Leap Academy Podcast · Episode 89 · Jul 7, 2026

Amy Porterfield: Why I Quit My Dream Job to Become an Entrepreneur

Watch on YouTube
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
Read more ↓Show less ↑
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
52 minutes
Leap PodcastAmy Porterfield: Why I Quit My Dream Job to Become an Entrepreneur

New to Leap Academy? Ilana Golan has helped 70,000+ professionals reinvent their careers. Watch her free training to see the framework.

Watch the free training →
Watch the conversation

On YouTube

Listen

Open this episode in your podcast app

Apple PodcastsSpotifyYouTubeOr paste this episode title into any podcast app: Amy Porterfield: Why I Quit My Dream Job to Become an Entrepreneur
About Leap Academy

Where ambitious professionals leap to their next chapter.

Founded by Ilana Golan — Forbes contributor, board director, investor in 100+ companies, and former F-16 flight instructor commander — Leap Academy has helped 70,000 people across 4 continents reinvent their careers and build lasting reputations.

  • American Business Awards Startup of the Year, 2023
  • Inc. 5000 Fastest Growing Company
  • Featured on Forbes, Yahoo Finance, NBC, CBS, ABC
Ilana Golan, Founder & CEO
Founder & CEO
Ilana Golan

Hosts every episode. Has guided thousands of professionals through career reinventions, leadership leaps, and brand building.

70,000
Lives impacted
$60M
Market value
4
Continents
Featured episodes · Editor's picks

Don't miss these conversations

Latest episodes

New on the show this month