Leap Academy with Ilana Golan

When Kim Perell was fired, she had to fire all her friends on the same day. The company she thought would make her a millionaire had just gone bankrupt, leaving her with no income or backup plan. Instead of giving up, she took a $10,000 loan from her grandmother to start her first company from her kitchen table. That bet led to a $20 million exit and eventually, a $235 million company. In this episode, Kim joins Ilana to share how to turn setbacks and mistakes into million-dollar breakthroughs and how to overcome the limiting beliefs holding you back. She also reveals the four pillars that helped her achieve success without burning out.

Kim Perell is a 9x founder, 3x bestselling author, and investor in 100+ companies. Kim became a multi-millionaire by the time she was 30, and sold her last company for $235 million to Singtel, while simultaneously running multi-million-dollar companies.

In this episode, Ilana and Kim will discuss:

(00:00) Introduction 

(04:08) Growing Up in the Shadow of Her Twin Sister

(07:07) Learning Risk and Failure from Entrepreneur Parents

(09:46) How Getting Fired Led to a Career Pivot

(13:31) Her Grandma’s Life-Changing $10K Loan

(16:37) Using The 70% Rule to Make Business Decisions

(18:48) The Four Pillars of Business Success

(23:50) Selling Her Business for $20 Million

(28:02) Building a Money Mindset 

(30:59) The Dangers of Failing to Pivot Or Make Mistakes

(40:13) Teaching Your Children Resilience

(45:01) Q&A: How to Chase Success Despite Fear

Kim Perell is a 9-time founder, 3-time bestselling author, top keynote speaker, and investor in over 100 companies. Her book, Mistakes That Made Me a Millionaire, offers a transformative guide to turning setbacks into million-dollar opportunities. An award-winning entrepreneur, Kim has appeared on major platforms and serves as a judge for Entrepreneur Magazine’s Elevator Pitch. She is dedicated to empowering the next generation of business leaders for success.

Connect with Kim:

Kim’s Website: https://kimperell.com/ 

Kim’s LinkedIn: https://www.linkedin.com/in/kimperell/ 

Kim’s Instagram: https://www.instagram.com/kimperell/ 

Resources Mentioned:

Kim’s Book,

Mistakes that Made Me a Millionaire: How to Transform Setbacks into Extraordinary Success: https://www.amazon.com/dp/1637747128 

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

Jason Fried didn’t follow the startup rules most founders swear by. He rejected venture capital, refused to chase growth at all costs, and chose to stay small on purpose. What started as a scrappy web design agency turned into Basecamp, a multi-million-dollar business built on profitability, simplicity, and conviction. In this episode, Jason joins Ilana to challenge everything you think you know about scaling a business. He also opens up about how a single leadership decision caused 30% of his company to quit overnight, and how staying principled ultimately made the company stronger.

Jason Fried is the co-founder and CEO of 37signals, the company behind Basecamp and HEY. For over 27 years, he has grown Basecamp into a multi-million dollar business without ever taking venture capital or chasing aggressive growth targets.

In this episode, Ilana and Jason will discuss:

(00:00) Introduction 

(03:18) Lessons from Selling Stereo Equipment as a Kid

(06:58) Starting 37signals from Scratch

(14:13) Pivoting to Software Through Basecamp  

(16:41) The Perks of Being a Small Company

(27:24) The Policy That Made 30% of the Company Quit 

(31:45) Surviving the Backlash and Rebuilding the Team

(39:21) Building Thicker Skin as a Leader

(42:43) How to Incorporate AI Without Getting Carried Away

(45:15) How Basecamp Is Reinventing Itself with Version 5

(48:56) Why Jason Won’t Advise His Younger Self

(54:07) Q&A: How to Decide Your Next Career Move

Jason Fried is a co-founder and CEO of 37signals, the makers of Basecamp. He is a bestselling author of Rework and It Doesn’t Have to Be Crazy at Work. Known for his contrarian approach to entrepreneurship, Jason emphasizes simplicity, profitability, and long-term thinking. For over 27 years, he has grown Basecamp into a multi-million dollar, fully profitable business without ever taking venture capital or chasing aggressive growth targets.

Connect with Jason:

LinkedIn: linkedin.com/in/jason-fried 

X: https://x.com/jasonfried

Resources Mentioned:

Jason’s Books: 

Rework: https://www.amazon.com/Rework-Jason-Fried/dp/0307463745

It Doesn't Have to Be Crazy at Work: https://www.amazon.com/Doesnt-Have-Be-Crazy-Work/dp/0062874780 

37signals’ Website: https://37signals.com 

Basecamp’s Website: https://basecamp.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

Don McGuire did not build his career through a straight line. He lost elections as a kid, moved every few years, started over again and again, and had to learn resilience early. After graduating from college, he was still unsure what to do, but a leap into the early cellular industry launched a career that would take him from sales to marketing and ultimately, the CMO seat at Qualcomm. In this episode, Don chats with Ilana about how to stay in control of your career in a world changing at the speed of AI. He shares why resilience matters more than ever, how to spot the right time to leap, and what it takes to stay relevant in a crowded job market.

Don McGuire is the Executive Vice President and Chief Marketing Officer of Qualcomm, with over 25 years of experience across service providers, semiconductors, and technology marketing. In 2025, he was named one of Forbes’ World’s Most Influential CMOs.

In this episode, Ilana and Don will discuss:

(00:00) Introduction

(03:14) The Early Experiences That Built Don’s Resilience

(10:46) His Love for Marketing and Journey Into Tech

(18:00) The Transition From Sales to Marketing

(20:18) Why You Must Stay in Control of Your Own Destiny

(23:25) Startup Lessons, Consulting, and Selling Yourself

(27:43) Knowing When It Was Time to Leap Back Into Corporate

(31:45) The Crisis That Forced Qualcomm to Tell Its Story

(38:16) The One Trait Gen Z and Gen Alpha Need Most

(40:33) How to Stand Out in an AI-Driven Job Market

(45:02) Why Portfolio Careers and Side Skills Matter

(48:03) What Excites Don Most About Qualcomm’s Future

(53:05) Q&A: How to Break the “I Can’t Get a Job” Mindset

Don McGuire is the Executive Vice President and Chief Marketing Officer of Qualcomm, where he oversees global marketing as the company expands beyond mobile into automotive, computing, AI, and other growth areas. Before joining Qualcomm, he held senior leadership roles at Intel and other major wireless and technology companies. In 2025, he was named one of Forbes’ World’s Most Influential CMOs.

Connect with Don:

Don’s LinkedIn: linkedin.com/in/donnymac 

Resources Mentioned:

Qualcomm: https://www.qualcomm.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

In the late 1990s, Mike Seckler started a company with little experience, plenty of curiosity, and no idea what was coming. Then the dot-com bubble burst. Almost overnight, capital disappeared. Companies collapsed. And Mike faced one of the hardest decisions of his career: laying off a third of his team to keep the company alive. That moment changed how he builds companies and leads today as CEO of Justworks. In this episode, Mike joins Ilana to share the real lessons behind building and scaling through uncertainty and how founders can avoid the leadership mistakes that derail most companies.

Mike Seckler is the President and CEO of Justworks, an HR platform helping over 14,000 small businesses manage payroll, benefits, compliance, and workforce management.

In this episode, Ilana and Mike will discuss:

(00:00) Introduction 

(02:42) From History and Geology Student to Entrepreneur

(07:05) The Early Days of Founding Employease

(09:08) Navigating the Dot Com Crash as a Founder

(14:53) Selling to ADP and Starting a New Venture

(17:23) Joining Justworks: From Board Member to COO

(24:37) Lessons from Transitioning to Justworks’ CEO

(26:00) The Biggest Blindspots for Small Businesses

(31:58) How to Beat Founder Loneliness

(36:34) Adapting to a Rapidly Evolving Market

(42:03) Justworks: Empowering Small Businesses for Growth

(44:49) Review and Q&A: BREAD Productivity Framework

Mike Seckler is a serial entrepreneur who has built and scaled multiple companies over the past two decades. Before joining Justworks, he co-founded Employease, an HR outsourcing firm that was eventually acquired by ADP, and later co-founded Euclidean Technologies, a company applying machine learning to public market investing. Today, as CEO of Justworks, Mike leads a platform serving thousands of small businesses and helping founders navigate the complexities of building and scaling their teams.

Connect with Mike:

Mike’s LinkedIn: linkedin.com/in/mikeseckler 

Resources Mentioned:

Justworks Website: https://www.justworks.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

When Bill Gurley wanted to break into Wall Street, there were no job postings waiting for him. So he flew to New York, knocked on doors, and asked strangers for meetings. That hustle launched a career that would eventually take him to Silicon Valley, where he became one of the most respected venture capitalists in tech. In this episode, Bill joins Ilana to reveal the unconventional lessons that shaped his journey. From chasing curiosity to designing your own career path, he explains how anyone can create opportunities, stand out in a crowded field, and build a career that actually excites them.

Bill Gurley is a Silicon Valley venture capitalist and a longtime partner at Benchmark Capital, a Silicon Valley venture capital firm. He has invested in and served on the boards of major companies, including Uber, OpenTable, Zillow, Nextdoor, and Stitch Fix.

In this episode, Ilana and Bill will discuss:

(00:00) Introduction 

(03:14) Where Bill Gurley’s Tech Curiosity Began

(05:09) Transitioning from Engineering to Finance

(08:25) Breaking Into Wall Street Without a Job Posting

(14:24) The Question That Made Him Quit Wall Street

(19:59) Making a Pivot to Venture Capital

(24:41) The Best Way to Get Into Venture Capital

(26:50) How to Know If You’re in the Right Career

(30:30) The Role of Experimentation in Career Growth

(33:20) How to Stand Out in a Competitive Job Market

(37:29) Why Location Can Make or Break Your Career

(40:50) Breaking Free From the “Safe Career” Pressure

(48:30) The 5–5–5 Rule for Career Experiments

Bill Gurley is a venture capitalist, technology investor, and general partner at Benchmark Capital, best known for his early investment in companies like Uber. Before venture capital, he worked as an engineer at Compaq and later as a Wall Street technology analyst. Throughout his career, Bill has been known for identifying transformative companies early and for his widely read blog Above the Cloud. His new book, Running Down a Dream, offers a practical guide to building a fulfilling career

Connect with Bill:

Bill’s X (Twitter): x.com/bgurley 

Bill’s Website: abovethecrowd.com 

Resources Mentioned:

Bill’s Book, Runnin' Down a Dream: How to Thrive in a Career You Actually Love: https://www.amazon.com/dp/0593799666 

One Up On Wall Street: How to Use What You Already Know to Make Money in the Market by Peter Lynch: https://www.amazon.com/dp/0743200403 

Range: Why Generalists Triumph in a Specialized World by David Epstein: https://www.amazon.com/dp/0735214484 

Greenlights by Matthew McConaughey: https://www.amazon.com/dp/0593139135 

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