Leap Academy with Ilana Golan

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

Nir Eyal grew up clinically obese, ashamed of his body, and convinced that food controlled him. He tried every diet: low-fat, keto, vegetarian, and intermittent fasting. Each one worked until it didn’t. What finally changed his life wasn’t a meal plan; it was his belief. When he believed a plan would work, it worked. When that belief cracked, the weight returned. And he realized this pattern doesn’t just apply to weight; it shows up in every area of life. In this episode, Nir joins Ilana to reveal the hidden force behind your success or stagnation. He unpacks the science of belief, how it shapes what you see, feel, and do, and the practical framework to break limiting beliefs before they break you.

Nir Eyal is a bestselling author, behavioral design expert, and former Stanford lecturer known for his work on habit formation, psychology, and human behavior. As an entrepreneur and angel investor, Nir has backed multi-billion-dollar companies including Canva and Kahoot!.

In this episode, Ilana and Nir will discuss:

(00:00) Introduction 

(03:14) Childhood and Weight Loss Struggles

(07:34) Why Affirmations and Vision Boards Don’t Work

(09:18) Facts vs Faith vs Beliefs

(10:59) His Journey from Founder to Bestselling Author

(16:01) The Power of Belief in Success and Failure 

(24:49) The ‘Messy Middle’: Knowing When to Persist vs Quit

(32:06) Skills Gap vs Belief Gap in Leaders and Teams

(34:0) The Four Questions to Rewire a Limiting Belief

(46:51) Q&A: Crafting a Memorable Pitch Story

Nir Eyal is a bestselling author, behavioral design expert, and former Stanford lecturer. He is the author of Hooked and Indistractable, which have sold over one million copies worldwide and been translated into more than 30 languages. His latest book, Beyond Belief, explores how hidden beliefs shape our limitations and how to replace them to unlock personal and professional growth. An entrepreneur and angel investor, Nir has backed multi-billion-dollar companies including Canva and Kahoot!.

Connect with Nir:

Nir’s Website: http://nirandfar.com

Nir’s Instagram: instagram.com/neyal99

Nir’s LinkedIn: linkedin.com/in/nireyal

Resources Mentioned:

Nir’s Books:

Beyond Belief: The Science-Backed Way to Stop Limiting Yourself and Achieve Breakthrough Results: https://www.amazon.com/dp/0593852036

Indistractable: How to Control Your Attention and Choose Your Life: https://www.amazon.com/dp/194883653X

Hooked: How to Build Habit-Forming Products: https://www.amazon.com/dp/1591847788

Nir’s 30-Day Belief Transformation Journal: nirandfar.com/beyond-belief

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

Dr. Amy Shah did everything she was supposed to do. Ivy League education. Elite medical training. Multiple board certifications. On paper, her life looked like a success. But behind the accolades, she was exhausted, disconnected, and running on stress. Then a near-fatal car accident forced her to confront a hard truth. The life she built was slowly breaking her body and mind. In this episode, Amy joins Ilana to share how a personal health crisis became the catalyst for a complete reinvention. She opens up about leaving the traditional medical path without burning the boats, building a science-backed wellness platform, and why women are being failed by modern healthcare.

Dr. Amy Shah is a double board-certified physician and nutrition specialist. Through her books and wellness platform, Dr. Amy empowers millions to optimize their health with evidence-based strategies rooted in nutrition, gut health, exercise, and lifestyle medicine.

In this episode, Ilana and Dr. Amy will discuss:

(00:00) Introduction 

(03:30) How a Near-Fatal Accident Became a Wake-Up Call

(09:51) From Traditional Medical Path to a Wellness Brand

(13:08) Building a Personal Brand Despite Pushback

(17:13) The Power of Having a Supportive Network

(21:47) How Dr. Amy Built a Powerful Portfolio Career

(23:51) Understanding Women's Health: The 30-30-3 Framework

(26:41) The Science of Probiotics and Gut Health

(30:24) The 4-3-2-1 Movement Framework for Peak Health

(37:32) Managing Stress and Cortisol Levels

(43:42) Building a Personal Brand and Finding Your Path

(47:17) Her Immigrant Roots and Its Impact

(51:44) Review and Q&A: Beating Ageism in Your Career Journey

Dr. Amy Shah is a double board-certified physician and nutrition specialist. She is the bestselling author of I’m So Effing Hungry and I’m So Effing Tired. Her latest book, Hormone Havoc, offers a science-backed guide to navigating the complexities of perimenopause and menopause. Through her books and wellness platform, Dr. Amy empowers millions to optimize their health with evidence-based strategies rooted in nutrition, gut health, exercise, and lifestyle medicine.

Connect with Dr. Amy:

Dr. Amy’s Website: https://amymdwellness.com 

Dr. Amy’s Instagram: instagram.com/dramyshah 

Resources Mentioned:

Dr. Amy’s Books, 

Hormone Havoc: A Science-Backed Protocol for Perimenopause and Menopause: Sleep Better. Think Better. Feel Better: https://www.amazon.com/dp/0063420856 

I'm So Effing Hungry: Why We Crave What We Crave – and What to Do About It: https://www.amazon.com/dp/0063285118 

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

The world tells leaders they must be everything: visionary, innovator, operator, executor. Patrick Lencioni tried, but it nearly crushed him. He wasn’t exhausted from effort; he was exhausted from misalignment. He discovered what most high performers never admit: trying to be everything is the fastest path to burnout. That insight became The Six Types of Working Genius, a simple framework reshaping how teams work by aligning people with the work that gives them energy. In this episode, Patrick joins Ilana to break down the Six Types of Working Genius and show how aligning your strengths can transform your career, your team, and your fulfillment at work.

Patrick Lencioni is a bestselling author and organizational health expert, and the founder of The Table Group. Named by Fortune as “one of the new gurus you should know,” Patrick helps leaders build healthy, high-performing organizations grounded in trust and clarity.

In this episode, Ilana and Patrick will discuss:

(00:00) Introduction 

(02:46) Patrick’s Early Life and Career Beginnings

(08:31) Joining Oracle and Pitching Ideas

(12:36) Turning Down a Job Offer from Steve Jobs

(15:40) The Decision to Start the Table Group

(20:18) Navigating the Hard Moments in Entrepreneurship

(23:30) Short Attention Spans as a Bestselling Author 

(28:06) The Birth and Impact of Working Genius 

(34:48) Applying Working Genius to Career Choices

(41:05) W-I-D-G-E-T: The Six Types of Working Genius

(54:57) Healing Childhood Scars and Understanding Self

(59:15) Q&A: The Keys to Building a Portfolio Career

Patrick Lencioni is a bestselling author and organizational health expert, and the founder of The Table Group. He has written 13 books with over 7 million copies sold worldwide, including The Five Dysfunctions of a Team. He is also the creator of The 6 Types of Working Genius, a framework that helps teams identify the work that energizes them and improves performance. Named by Fortune as “one of the new gurus you should know,” Patrick helps leaders build healthy, high-performing organizations grounded in trust and clarity.

Connect with Patrick:

Patrick’s LinkedIn: linkedin.com/in/patrick-lencioni-orghealth

Patrick’s Instagram: instagram.com/patricklencioniofficial

Resources Mentioned:

Patrick’s Books: 

The Five Temptations of a CEO: https://www.amazon.com/dp/B0062OAEWM

The Five Dysfunctions of a Team: https://www.amazon.com/dp/0787960756

The 6 Types of Working Genius: A Better Way to Understand Your Gifts, Your Frustrations, and Your Team: https://www.amazon.com/dp/B09XGPCM36

Working Genius Website: https://www.workinggenius.com

Take the Working Genius Assessment: https://www.workinggenius.com/about/assessment 

Leap Academy:

LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life.

📍 San Jose, CA

📅 Feb 26–28, 2025

If you’re ready to step into clarity, confidence, and bold action, this is your moment.

👉 Grab your ticket before doors close at leapacademy.com/leapcon

Before Damian Maldonado was negotiating billion-dollar valuations or building businesses across Puerto Rico, he was a kid living in poverty and sharing bunk beds in a homeless shelter with his brothers. But those early years didn’t break him. They led him to become the co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S. In this episode, Damian joins Ilana to share how growing up in poverty shaped his relationship with risk, money, and resilience, and what it really takes to bootstrap a company through market crashes, massive layoffs, and billion-dollar decisions.

Damian Maldonado is a serial entrepreneur, investor, and co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S., which he helped grow from a small startup into a national brand.

In this episode, Ilana and Damian will discuss:

(00:00) Introduction 

(02:57) Growing Up in Poverty and a Homeless Shelter

(08:42) Key Lessons from Early Jobs

(11:42) Pitching to a CEO at 21 Without Fear of Rejection

(14:38) Damian’s Journey into the Mortgage Industry

(19:14) Starting America Financing With No Safety Net

(22:30) Leading Through Layoffs and Downturns

(27:07) Why He Turned Down a Billion-Dollar Offer

(30:57) Leadership Lessons from Richard Branson

(34:25) Building a Portfolio Career with Adventure

(42:53) Q&A: Crafting a Response to ‘Tell Me About Yourself’

Damian Maldonado is the co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S., which he helped grow from a small startup into a national brand. He also co-founded American Home Agents and has expanded his business interests into hospitality and lifestyle ventures in Puerto Rico, including a boutique beachfront hotel, restaurant, and kiteboarding school, creating jobs and adding value to the local community.

Connect with Damian:

Damian’s Website: https://damianmaldonado.com 

Damian’s Instagram: instagram.com/damiankitepr 

Resources Mentioned:

American Financing Website: americanfinancing.net 

Numero Uno Website: numerounopr.com

Awaken the Giant Within by Tony Robbins: https://www.amazon.com/Awaken-Giant-Within-Immediate-Emotional/dp/0671791540

Think And Grow Rich by Napoleon Hill: https://www.amazon.com/Think-Grow-Rich-Landmark-Bestseller/dp/1585424331 

Rich Dad Poor Dad by Robert Kiyosaki: https://www.amazon.com/Rich-Dad-Poor-Teach-Middle/dp/1612681131/ 

The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Tim Ferriss: https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357

Leap Academy:

LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life.

📍 San Jose, CA

📅 Feb 26–28, 2025

If you’re ready to step into clarity, confidence, and bold action, this is your moment.

👉 Grab your ticket before doors close at leapacademy.com/leapcon