It seemed like all was lost after Nicholas “Nick” Stone was cut from three different teams during his sports career. However, he used this setback to transition into finance, eventually founding Bluestone Lane, a successful coffee shop chain. Despite having never made coffee before, his love for the premium coffee culture of his home country, Australia, inspired him to transform the U.S. coffee experience into a more personalized one. In this episode, Nick joins Ilana to share how he transformed an 87% revenue loss into an opportunity for innovation and reinvention, emphasizing his commitment to community, human connection, and exceptional quality.

Nicholas Stone is an Australian businessman, former professional athlete, and banker. He is also the founder and CEO of Bluestone Lane, a premium coffee and café brand inspired by Australia’s rich coffee culture.

In this episode, Ilana and Nick will discuss:

(00:00) Introduction 

(01:50) The Resilience That Took Him from Sports to Finance

(07:13) Moving from Australia to Chase a New York Dream

(09:15) Building Connections and Networks in New York

(12:23) Founding Bluestone to Fix U.S. Coffee Culture

(14:59) Keeping His Day Job to Launch Bluestone Lane

(20:35) Creating a People-First Café Experience

(23:09) Tough Lessons on Expanding Too Soon

(25:52) Filtering Advice in the Early Stages of Business

(27:33) The Hidden Challenges of Running a Café Chain

(32:33) How Nick Manages Founder Stress with Support

(37:35) Surviving the Pandemic After Losing 87% of Revenue

(45:02) Why Bluestone Sticks to Quality Over Shortcuts

(48:40) Nick's Focus on Values and Promoting Internally

(50:21) The Power of Celebrating Small Wins in Business

Nicholas Stone is an Australian businessman, former professional athlete, and banker. He is also the founder and CEO of Bluestone Lane, a premium coffee and café brand inspired by Australia’s rich coffee culture. Under his leadership, Bluestone Lane has become the fastest-growing premium café brand in the U.S., raising $70 million in venture capital and expanding to over 65 locations. Nick has been featured in The New York Times, CNBC, Bloomberg, the Wall Street Journal, and more.

Connect with Nick:

Nick’s Website: https://bluestonelane.com/ 

Nick’s LinkedIn: linkedin.com/in/nicholas-stone-49465767  

Leap Academy:

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After losing seven elections in college, Bill George realized that leadership is about building relationships and helping others grow. Personal losses, including the deaths of his mother and fiancée, taught him resilience and the value of purpose. Though on track to become CEO at Honeywell, Bill chose a more fulfilling path at Medtronic, focusing on the company’s mission to restore lives. In this episode, Bill takes Ilana through his leadership philosophies and shares lessons on building relationships, leading with values, and prioritizing purpose over profits, which were pivotal in driving Medtronic's success.

Bill George is a renowned thought leader, educator, and bestselling author, best known for his transformative leadership as CEO of Medtronic. A strong advocate for values-driven leadership, Bill emphasizes leading with purpose, values, relationships, and heart. 

In this episode, Ilana and Bill will discuss:

(00:00) Introduction 

(04:30) Learning Leadership Lessons Through Early Failures

(06:50) Losing His Mother and Fiancée Suddenly

(09:22) Turning Tough Moments Into Learning Opportunities

(11:37) The Value of Building Relationships

(13:16) Choosing Purpose Over the CEO Path at Honeywell

(16:18) Measuring Impact by Lives Restored at Medtronic

(21:42) Mentoring Across Different Generations for Free

(24:20) Making a Risky Move to Challenge the FDA

(26:47) Leadership Beyond Just Making Profits

(33:18) Using Data and Intuition to Make Bold Decisions

(35:48) Remarkable Leaders Who Followed Their ‘True North’

(44:21) Balancing Leadership, Family, and Self-Care

(48:56) Bill's Advice for Emerging Leaders

Bill George is a renowned thought leader, educator, and bestselling author, best known for his transformative leadership as CEO of Medtronic. A strong advocate for values-driven leadership, Bill emphasizes leading with purpose, values, relationships, and heart. Earlier in his career, he held senior executive roles at Honeywell and Litton Industries. He is the author of True North and serves as an Executive Fellow at Harvard Business School, where he taught for nearly 20 years, shaping the next generation of leaders

Connect with Bill:

Bill’s Website: http://www.billgeorge.org/ 

Bill’s LinkedIn: linkedin.com/in/williamwgeorge/ 

Resources Mentioned:

Bill’s Book, True North: Discover Your Authentic Leadership: https://www.amazon.com/True-North-Discover-Authentic-Leadership/dp/0787987514 

Bill’s Book, True North, Emerging Leader Edition: Leading Authentically in Today's Workplace:

https://www.amazon.com/True-North-Emerging-Leader-Authentically-ebook/dp/B0BBSWCVT4 

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

Kirthiga Reddy’s legacy is built on bold decisions and breaking barriers. Defying cultural norms, she became a top engineering graduate in a society where her mother was denied an education. After moving to the U.S., her career soared, until she took a 40% pay cut to join a startup. That gamble led her to become Facebook’s first employee in India, scaling revenues to millions. She later made history as SoftBank Investment Advisers’ first female partner. Now, as CEO of web3 startup Virtualness, she proves that reinvention and boldness drive transformative growth. In this episode, Kirthiga joins Ilana to reflect on her career transitions and the power of embracing challenging ventures.

Kirthiga Reddy is a technology leader and growth-stage investor with over 20 years of experience. She was the first female Investing Partner at SoftBank Investment Advisers and served as Managing Director of Facebook India.

In this episode, Ilana and Kirthiga will discuss:

(00:00) Introduction 

(02:01) Excelling Academically Despite Limited College Options

(03:37) Turning Gender Bias Into a Drive for Tech Empowerment

(05:37) Moving from India to the US to Further Her Education

(07:58) Landing a Job in Silicon Valley

(10:24) Choosing a 40% Pay Cut for the Big Picture

(15:21) Joining Facebook India as Its First Employee

(18:40) How Kirthiga Helped Drive Facebook’s Global Expansion

(23:13) The Transition from Facebook Exec to Venture Capitalist

(30:33) Transforming WeWork Into a Profitable Business

(32:12) Redefining Digital Verifications with Verix

(35:57) Living by a “No Regrets” Policy

(38:15) Kirthiga’s Relentless Drive for Growth

(40:16) Why Bold Career Moves Are Worth the Risk

(42:20) How to Get 100 Free Verix-Verified Certifications

(44:11) The Power of Lifting Others as You Rise

Kirthiga Reddy is a technology leader and growth-stage investor with over 20 years of experience. She is the CEO of Virtualness, an AI-powered blockchain platform, and served on the Board of Directors for WeWork. Kirthiga was the first female Investing Partner at SoftBank Investment Advisers, managing a portfolio of over $5 billion. She also served as Managing Director of Facebook India, scaling operations across South Asia and emerging markets.

Connect with Kirthiga:

Kirthiga’s Website: https://kirthigareddy.com/ 

Kirthiga’s LinkedIn: https://www.linkedin.com/in/kirthiga 

Resources Mentioned:

Verix’s Website: www.verix.io 

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

Despite her background in financial services, Lacy Garcia faced significant financial challenges after her marriage ended. She struggled with imposter syndrome, advising clients on finances while dealing with her own financial issues. Too embarrassed to seek help and unable to find the right advisors, Lacy turned her fear and discomfort into a drive for financial education and empowerment. She founded Willow, a fintech company focused on making financial advice more accessible, especially for those overlooked by traditional services. In this episode, Lacy joins Ilana to share insights on financial literacy, achieving stability and independence, and Willow’s approach to matching clients with the right advisors.

Lacy Garcia is the founder and CEO of Willow, an award-winning platform that connects clients with certified financial advisors using an AI-powered matching system based on their financial goals and preferences. 

In this episode, Ilana and Lacy will discuss:

(00:00) Introduction 

(01:44) How Divorce Shaped Her Passion for Financial Education

(04:02) Finding Clarity Amid Financial Fears and Uncertainties

(09:52) From Financial Ignorance to a Career in Finance

(13:14) Letting Go of Shame to Achieve Financial Health

(16:13) Why You Don’t Need More Money to Start Investing

(20:01) Creating Willow to Make Financial Advice Accessible

(24:29) How Personal Experience Shaped Willow's Mission

(29:07) Navigating the Weight of Decision-Making in Startups

(34:31) The Role of Investment in Startup Growth

(39:56) Ways to Avoid Common Financial Mistakes

(42:55) Getting Personalized Financial Advice for Free

(43:55) The Importance of Financial Literacy

Lacy Garcia is the founder and CEO of Willow, an award-winning platform that connects clients with certified financial advisors using an AI-powered matching system based on their financial goals and preferences. She is passionate about empowering advisors to better serve the next generation of clients through tailored training programs. Lacy has been featured in top media outlets like The TODAY Show, Business Insider, and Yahoo Finance, and was named Hispanic Empowering Executive of the Year in 2023 by Wealth Solutions Report.

Connect with Lacy:

Lacy’s Website: https://www.trustwillow.com/ 

Lacy’s LinkedIn: https://www.linkedin.com/in/lacy-garcia/ 

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

Neil Patel’s story shows how hard work, persistence, and learning from failure lead to success. As a teenager, he started businesses, including building websites, but struggled with ineffective marketing agencies. This pushed him to learn digital marketing, and by 16, he helped a client make $20M, marking the start of his career. After facing challenges with his earlier ventures, he shifted from starting businesses to acquiring and turning underperforming ones into successes. Now, as the founder of NP Digital, he runs a global marketing company that helps businesses grow. In this episode, Neil talks with Ilana about his journey, the strategies behind his success, and how businesses can overcome challenges and scale in today’s competitive market.

Neil Patel is a New York Times bestselling author, digital marketing expert, and the founder of one of the top 100 most brilliant companies, according to Entrepreneur Magazine. With over 15 years of experience, Neil has been instrumental in helping businesses grow their online presence and revenue.

In this episode, Ilana and Neil will discuss:

(00:00) Introduction 

(01:11) The Power of Hard Work Over Privilege

(01:39) From Teenage Hustle to Launching His First Website

(08:01) Learning Digital Marketing After Agency Failures 

(08:55) Helping a Client Reach $20M in Revenue at Age 16

(10:17) Attending College Due to Family Expectations

(11:55) How Experimentation Reveals Your True Strengths

(14:26) Lessons from Surviving Legal Battles at Kissmetrics

(19:53) Businesses That Found Success Despite Their Flaws

(22:35) Balancing Personal and Corporate Branding for Success

(25:24) Shifting from Building to Acquiring Businesses

(27:10) Neil’s Strategy for Improving Acquired Businesses

(31:15) Why “Renting Your Dreams” Can Lead to Future Success

(33:29) How Consistency and Networking Create Opportunities

(35:48) Empowering and Trusting Your Team for Results

(37:44) Hiring Experts to Reduce Risk and Drive Growth

(40:57) Neil Patel's Digital Marketing Services

Neil Patel is a New York Times bestselling author, digital marketing expert, and the founder of one of the top 100 most brilliant companies, according to Entrepreneur Magazine. Recognized as a top influencer by The Wall Street Journal and one of Forbes' top marketers, Neil has helped companies like Amazon, Microsoft, and Google grow through marketing. He is also the co-founder of NP Digital, a leading marketing agency. With over 15 years of experience, Neil has been instrumental in helping businesses grow their online presence and revenue.

Connect with Neil:

Neil’s Website: https://neilpatel.com/ 

Neil’s LinkedIn: https://www.linkedin.com/in/neilkpatel/ 

Neil’s YouTube: https://www.youtube.com/neilpatel 

Resources Mentioned:

NP Digital: https://npdigital.com/ 

Neil’s Book, Hustle: The Power to Charge Your Life with Money, Meaning, and Momentum: https://www.amazon.com/Hustle-Power-Charge-Meaning-Momentum/dp/1623367166 

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

A former lawyer turned fitness powerhouse, Robin Arzón’s journey is one of resilience and inspiration. After surviving a traumatic hostage situation in college, she turned to running as a way to heal and challenge herself. She went from casual runs to completing marathons and ultra-marathons. Despite being diagnosed with Type 1 diabetes, Robin refused to let it define her. She embraced the mantra, "Why not me?" and continued challenging herself to achieve more. In this episode, Robin shares with Ilana how she transformed a traumatic experience into a driving force for her life’s purpose, made a bold leap into the fitness world, and built a global brand that empowers millions.

Robin Arzón is a renowned fitness expert, former lawyer, author, and motivational speaker. She is best known as the VP and Head Instructor at Peloton, where she inspires millions with her high-energy cycling and strength classes.

In this episode, Ilana and Robin will discuss:

(00:00) Introduction 

(01:24) Surviving a Hostage Situation and Finding Inner Strength

(05:34) Discovering Running as a Healing Tool

(08:38) From Casual Runs to Completing Ultra-Marathons

(11:16) Transitioning from a Law Career to Fitness

(13:06) How Robin Landed a Job at Peloton with a Cold Email

(15:36) Living and Thriving with Type 1 Diabetes

(18:21) Juggling a Career, Motherhood, and Life’s Demands

(21:26) Pushing Past Her Limits at Richard Branson’s StriveX Challenge

(24:41) Building a Global Brand Through Grit and Consistency

(28:05) Launching Swagger Society, a Community for Growth

(29:49) Upcoming Cookbook and Plant-Based Lifestyle

(31:34) Learning to Trust Life’s Redirections 

(33:27) Robin’s Career Pivots and Life-Changing Lessons

(36:46) How Everyday Actions Define Your Life and Career

Robin Arzón is a renowned fitness expert, former lawyer, author, and motivational speaker. She is best known as the VP and Head Instructor at Peloton, where she inspires millions with her high-energy cycling and strength classes. After overcoming a life-changing traumatic event, she pivoted from a law career to focus on health and wellness. Robin is also a New York Times bestselling author of Shut Up and Run and Strong Mama, sharing her personal stories and fitness philosophies. She advocates for mental and physical strength, promoting the power of movement and mindset to achieve personal transformation.

Connect with Robin:

Robin’s Website: https://www.robinarzon.com/ 

Robin’s Instagram: https://www.instagram.com/robinnyc 

Resources Mentioned:

Robin’s Book, Shut Up and Run: How to Get Up, Lace Up, and Sweat with Swagger: https://www.amazon.com/Shut-Up-Run-Sweat-Swagger/dp/0062445685 

Robin’s Journal, Welcome, Hustler: An Empowerment Journal: https://www.amazon.com/Welcome-Hustler-Empowering-Motivational-Self-Care/dp/1454946342 

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

Naveen Jain believes that no idea is too crazy to pursue. With the right questions and focus, you can turn big ideas into life-changing solutions. After his father's battle with stage 4 pancreatic cancer, Naveen wondered why early cancer detection wasn’t possible. This led him to apply his 'Why me? Why this? Why now?' framework, sparking innovation in early cancer detection and chronic disease management. In this episode, Naveen talks with Ilana about the mindset that drives him to solve the world’s toughest problems. He emphasizes the importance of staying focused, persistent, overcoming failure, and obsessing over solutions.

Naveen Jain is a serial entrepreneur, author, and philanthropist dedicated to solving the world’s biggest challenges through life-changing solutions. Driven by a relentless passion for innovation, he has built several successful companies in diverse fields. 

In this episode, Ilana and Naveen will discuss:

(00:00) Introduction 

(01:29) How Life’s Experiences Shape Who We Are

(04:50) The Three Questions You Must Ask Before Starting Any Project

(11:20) Overcoming Fear and Embracing ‘Moonshot’ Thinking

(13:16) Turning Personal Loss into a Health Revolution

(18:33) Why Microbiomes are the Key to Preventing Disease

(22:50) Using Cutting-Edge Tech for Early Cancer Detection

(30:07) How Obsession, Not Passion Helps Entrepreneurs Succeed

(33:00) The Power of Persistence in Overcoming Challenges

(39:41) Parenting Future Entrepreneurs

(42:41) Teaching Kids to Question Everything and Drive Innovation

(50:26) Embracing Crazy Ideas and Never Giving Up

(51:34) How Viewing Failure as an Experiment Fuels Growth

Naveen Jain is a serial entrepreneur, author, and philanthropist dedicated to solving the world’s biggest challenges with life-changing solutions. Driven by a relentless passion for innovation, he has built several successful companies in diverse fields. He founded Viome, a health-tech company specializing in personalized medicine through microbiome and gene expression analysis. He also co-founded Moon Express, a company focused on mining resources from the Moon. Naveen is the author of Moonshots, and his mission is to help humanity realize its fullest potential on Earth and beyond.

Connect with Naveen:

Naveen’s Website: https://naveenjain.com/ 

Naveen’s LinkedIn: linkedin.com/in/naveenjainintelius/ 

Naveen’s Instagram: www.instagram.com/naveenjainceo 

Resources Mentioned:

Evvy Website: https://www.evvy.com/ 

Naveen’s Book, Moonshots: Creating a World of Abundance: https://www.amazon.com/Moonshots-Creating-Abundance-Naveen-Jain/dp/099973640X  

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

Jeff Krauss went from being a shy kid with no prior experience in event planning to a trusted name in celebrity event management. Despite facing setbacks, including financial struggles and failed ventures in nightlife, Jeff learned the ropes of event planning and built a reputation for trust and hospitality. Over time, he expanded his network by forging key relationships and organizing high-profile events for celebrities like George Clooney and Saturday Night Live. In this episode, Jeff shares how he navigated career challenges, the importance of networking and perseverance, and his pivot to creating impactful projects like Fan Room Live, a virtual event series that blends entertainment with charitable impact.

Jeff Krauss is a renowned celebrity event producer, entrepreneur, and influencer marketer. He is the President of IE Group, an event management and production company specializing in high-profile events.

In this episode, Ilana and Jeff will discuss:

(00:00) Introduction 

(01:41) How a Shy Kid Leaped Into Event Promotion

(05:24) Finding Mentors Who Shaped His Promotion Skills

(07:20) Transitioning to Larger Events Through Strategic Networking

(12:50) Navigating Financial Struggles in the Lounge Business

(15:20) Tips for Breaking Into Celebrity Circles

(19:21) The Long Road to Working with Saturday Night Live

(25:17) Moving Past Rejection Without Overthinking It

(29:18) Pivoting During the Pandemic to Launch FanRoom Live

(32:34) How FanRoom Live is Positively Impacting Lives

(36:00) Jeff’s Shift from Nightlife to Other Ventures

(38:37) Why Ignoring the Noise Is Key to Thriving in Business

(40:09) Balancing Humility and Confidence in Business

(41:38) Why a Strong Social Media Presence is Crucial for Success

(43:23) Creating Quote Notes, a Platform for Spreading Positivity

Jeff Krauss is a renowned celebrity event producer, entrepreneur, and influencer marketer. He is the President of IE Group, an event management and production company specializing in high-profile events. Jeff is also the co-founder of FanRoom Live, a virtual event series that connects celebrities with fans while supporting charitable causes. In addition, he serves as the Chief Inspiration Officer at QuoteNotes, a platform dedicated to sharing positivity and inspiration. Today, Jeff continues to innovate within the events industry, focusing on impactful projects and creating memorable experiences for audiences and clients.

Connect with Jeff:

Jeff’s Website: https://www.iegny.com/

Jeff’s LinkedIn: https://www.linkedin.com/in/jeff-krauss-86745353

Jeff’s Instagram: https://www.instagram.com/iegroupnyc 

Resources Mentioned:

Quote Notes’ Instagram: https://www.instagram.com/quotenotesofficial/ 

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

Jessica Jackley grew up with values of generosity and compassion, which inspired her passion for helping others. Initially uninterested in business, she had a life-changing moment after hearing Dr. Muhammad Yunus speak about microfinance. This led her to East Africa, where she saw firsthand how small loans helped entrepreneurs escape poverty. In 2005, Jessica co-founded Kiva, a groundbreaking platform that enables individuals to lend small amounts directly to entrepreneurs worldwide. In this episode, Jessica talks to Ilana about how Kiva redefines the way people think about giving and social impact, the challenges of growing a social impact platform, and the importance of living a purposeful life focused on creating lasting change.

Jessica Jackley is a social entrepreneur and investor dedicated to empowering entrepreneurs with the resources they need to succeed. As co-founder of Kiva, the world’s first microfinance crowdfunding platform, she has helped facilitate over $2B in loans since 2005, redefining traditional charity through partnerships built on equality.

In this episode, Ilana and Jessica will discuss:

(00:00) Introduction 

(01:44) Early Childhood and Core Values

(02:18) From Poetry Student to Landing a Temp Job at Stanford

(04:04) Discovering Social Entrepreneurship 

(05:22) The “What If” Questions That Led to the Birth of Kiva

(08:03) Navigating Kiva’s Startup Struggles

(11:39) Jessica’s Approach to Decision-Making

(13:20) How Kiva Builds Partnerships with Real Stories, Not Guilt

(18:56) Patrick’s Inspiring Story of Resilience

(22:00) Building a Life of Purpose, Impact, and Growth

(26:34) How Jessica Learned to Dream Beyond Limits

(28:08) The Real Value of Impact in Every Decision

Jessica Jackley is a social entrepreneur and investor dedicated to empowering entrepreneurs with the resources they need to succeed. As co-founder of Kiva, the world’s first microfinance crowdfunding platform, she has helped facilitate over $2B in loans since 2005, redefining traditional charity through partnerships built on equality. A venture capitalist, educator, and advocate for impact-driven entrepreneurship, Jessica inspires others to create meaningful solutions. She is the author of Clay Water Brick, a TIME "100 Most Influential People" honoree, and currently serves as a Professor of Entrepreneurship at USC’s Marshall School of Business.

Connect with Jessica:

Jessica’s Website: https://www.jessicajackley.com/

Jessica’s LinkedIn: linkedin.com/in/jessicajackley/ 

Resources Mentioned:

Kiva Website: https://www.kiva.org/ 

Jessica’s Book, Clay Water Brick: Finding Inspiration from Entrepreneurs Who Do the Most with the Least: https://www.amazon.com/Clay-Water-Brick-Inspiration-Entrepreneurs/dp/0679643761 

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

Spencer Rascoff’s career is a masterclass in navigating crises. After co-founding the travel site Hotwire, the 9/11 tragedy devastated the travel industry. Spencer helped steer the company through this crisis, leading to its $685 million sale to Expedia. He then co-founded Zillow, guiding it through the 2008 housing crash and growing it to a $20 billion market cap. His third venture, Pacaso, a luxury vacation home co-ownership platform, launched just before the pandemic. Despite initial fears about shared spaces, the crisis increased demand for second homes, helping Pacaso achieve unicorn status. In this episode, Spencer shares with Ilana his hard-earned insights on navigating the highs and lows of startup life and turning crises into opportunities.

Spencer Rascoff is a serial entrepreneur, investor, and business executive best known for co-founding Hotwire, Zillow, and Pacaso. As the founder of 75 & Sunny Ventures, he mentors and invests in startups, aiming to democratize access to business opportunities and innovation.

In this episode, Ilana and Spencer will discuss:

(00:00) Introduction 

(02:03) His Early Exposure to Entrepreneurship

(04:13) Building Strong Work Ethic in High School

(06:07) Spencer’s Path from Banking to Startups

(07:21) Founding Hotwire and the Impact of 9/11

(09:47) The Hard Truths of Building Startups

(11:47) What It Takes to Keep Going During a Startup Crisis

(13:58) How Zillow’s ‘Zestimate’ Led to Its Explosive Launch

(17:52) Balancing Speed and Quality in Product Launches

(20:50) Zillow’s Mobile-First Strategy That Won the Market

(25:35) How Zillow Thrived During the 2008 Mortgage Crisis

(28:40) Leading Zillow with Empathy and Teamwork

(32:49) Why Spencer Left Zillow at Its Peak

(33:58) The Fast Rise of Pacaso Amid Pandemic Fears

(37:29) How Pacaso Is Opening Up to Retail Investors

(38:20) Spencer’s Mission to Build Accessible Ventures

(41:53) The Secret to His Success

Spencer Rascoff is a serial entrepreneur, investor, and business executive best known for co-founding Hotwire, Zillow, and Pacaso. He served as CEO of Zillow, leading the company through the 2008 housing crisis and growing it to 4,500 employees and $3 billion in revenue. In 2015, Spencer co-wrote and published his first book, Zillow Talk: Rewriting the Rules of Real Estate, and in 2017, he was named the Most Powerful Person in Residential Real Estate by the Swanepoel Power 200. As the founder of 75 & Sunny Ventures, he mentors and invests in startups, aiming to democratize access to business opportunities and innovation.

Connect with Spencer:

Spencer’s Website: www.heylibby.ai/spencerrascoff 

Spencer’s LinkedIn: linkedin.com/in/spencerrascoff 

Spencer’s Twitter: x.com/spencerrascoff 

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