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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
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Tom Bilyeu’s journey is a powerful story of transformation, from self-doubt to self-mastery. His early years were shaped by fear of failure, a lack of direction, and doubts from those around him. After struggling to break into the film industry, he joined a startup with the goal of getting rich, but found himself unhappy and in a strained marriage. Taking a leap of faith, Tom walked away from millions to pursue something more meaningful. This gave rise to Quest Nutrition, a billion-dollar company creating nutritious, great-tasting products. Yet, for Tom, wealth was never the endgame. He launched Impact Theory, a media company designed to impact lives positively. In this episode, Tom shares with Ilana the key moments that shaped his career, the philosophies that drive him, and how he defines true success.
Tom Bilyeu is a billion-dollar entrepreneur, motivational speaker, co-founder of Quest Nutrition, and founder of Impact Theory. Through his content, he inspires millions by sharing tips on overcoming self-doubt, developing the right mindset, and building resilience for success.
In this episode, Ilana and Tom will discuss:
(00:00) Introduction
(01:43) Facing Doubts and Rejection
(04:21) How Neuroscience Changed His Mindset
(06:28) Why People Struggle to Make Progress
(07:59) Learning the Power of Discipline in Film School
(12:46) Tom’s Guide to Finding Your Next Step
(15:25) Walking Away from $2 Million to Save His Marriage
(17:14) Building Quest Nutrition with the Right Team
(22:00) Why Tom Launched Quest Nutrition
(24:37) The Key to Surviving Entrepreneurship
(26:19) Strategies for Thriving in Competitive Markets
(30:20) Solving What Others Say Can't Be Done
(31:16) Conquering Fear Through Hardwork
(36:20) The Journey from Quest to Impact Theory
(40:15) Using Entertainment to Inspire Young Minds
(45:24) Lessons from Childhood that Built Tom’s Resilience
(48:06) Two Beliefs to Unlock Your Potential
(49:44) Letting Go of Ego to Grow
Tom Bilyeu is a billion-dollar entrepreneur, motivational speaker, and co-founder of Quest Nutrition, a company that revolutionized the health and fitness industry with its protein bars. After selling Quest Nutrition, he founded Impact Theory, a media company focused on empowering people through storytelling. Through his podcasts, interviews, and online content, Tom inspires millions by sharing tips on overcoming self-doubt, developing the right mindset, and building resilience.
Connect with Tom:
Tom’s Website: https://tombilyeu.com
Tom’s YouTube: youtube.com/c/TomBilyeu
Tom’s Twitch: www.twitch.tv/tombilyeu
Leap Academy:
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Chris Savage is a master at pivoting. He co-founded Wistia with his best friend in his living room, originally aiming to create an online filmmaking competition platform. When that didn’t work, they shifted to portfolio tools and later to secure video hosting for businesses, which became Wistia’s core offering. Chris wasn’t afraid to turn down major clients like HBO when their goals didn’t align. Despite running a $300k monthly loss and receiving multiple life-changing acquisition offers, he rejected them and took on $17.3M in debt to continue growing the business. In this episode, Chris opens up to Ilana about the highs and lows of building Wistia, how he made tough decisions, and what it takes to build a lasting business.
Chris Savage is the CEO and co-founder of Wistia, a leading video-hosting platform designed to help businesses create, host, and analyze video content in a way that maximizes engagement and drives growth.
In this episode, Ilana and Chris will discuss:
(00:00) Introduction
(00:19) The Twists and Turns of Launching Wistia
(05:02) Pivoting and Finding Success in the Unexpected
(08:22) From Zero to Paying Customers
(10:14) Rejecting an HBO Deal and Searching for Investors
(14:51) How Focus and Authenticity Drive Success
(18:02) Building a Serious Business with Fun Marketing
(20:33) Learning to Make Tough, Risky Decisions
(23:11) Chris’s Secret to Balancing Creativity and Speed
(26:34) The Struggle to Close Deals and Break Even
(30:31) How He Pushes Through Hard Moments
(31:05) Turning Down Life-Changing Offers
(35:23) What Chris Learned from Taking Time Off
(38:24) The Power of Building a Personal Brand
(43:05) Why Wistia is the Top Choice for Video Marketing
(46:17) Chris’s Top Business Lessons
Chris Savage is the CEO and co-founder of Wistia, a leading video-hosting platform designed to help businesses create, host, and analyze video content in a way that maximizes engagement and drives growth. A strong advocate for the Boston startup ecosystem, Chris is passionate about exploring unconventional paths in tech, entrepreneurship, marketing, video, company-building, and behavioral economics. Before founding Wistia, he contributed to an Emmy Award-winning documentary and, in 2009, earned recognition as a Top Young Entrepreneur by BusinessWeek.
Connect with Chris:
Chris’s LinkedIn: www.linkedin.com/in/cjsavage
Chris’s Twitter: https://x.com/csavage
Resources Mentioned:
Webinar Wizard: https://wistia.com/webinarwizard
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.
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At age 12, Russell Brunson was inspired to become an entrepreneur after watching an infomercial about making money. Over the years, he faced massive personal and professional setbacks, from losing 60% of his staff to battling infertility, financial struggles, and nearly going to jail. But instead of giving up, he turned each failure into a lesson, tweaking his approach and ultimately co-founding the multi-billion-dollar company, ClickFunnels. In this episode, Russell shares with Ilana how he transformed his toughest setbacks into the foundation of his thriving business, offering powerful lessons on resilience, success, and the impact of authentic relationships.
Russell Brunson is a serial entrepreneur, bestselling author, and digital marketing expert. He is widely recognized as the co-founder of ClickFunnels, a leading marketing software company that helps businesses worldwide boost conversions and drive sales.
In this episode, Ilana and Russell will discuss:
(00:00) Introduction
(01:54) The Infomercial That Turned Him Into a Young Entrepreneur
(05:29) What Wrestling Taught Him About Overcoming Failure in Business
(07:55) Launching His First Business, The Potato Gun
(09:52) Russell’s Rollercoaster Journey to His First Million
(14:25) Key Lessons from His Toughest Year
(21:27) The Birth of ClickFunnels
(26:61) Finding Fulfillment in Helping Others Succeed
(28:58) Leading ClickFunnels Through Its First Major Crisis
(34:18) How Serving Tony Robbins Led to Lifelong Mentorship
(37:32) Building Lasting Relationships with the Dream 100 Strategy
(42:45) The Emotional Story of Russell’s Fertility Journey
(44:38) Why Vulnerability in Business Can Lead to Unlikely Success
(46:51) Tips for Building a Winning Team That Drives Your Success
(49:58) Turning Your Pain into an Asset
Russell Brunson is a serial entrepreneur, bestselling author, and digital marketing expert. He is widely recognized as the co-founder of ClickFunnels, a leading marketing software company that helps businesses worldwide boost conversions and drive sales. Over the past 19 years, he has built a community of over a million entrepreneurs and authored New York Times bestsellers, including DotCom Secrets and Expert Secrets.
Connect with Russell:
Russell’s Website: www.russellbrunson.com
Russell’s LinkedIn: https://www.linkedin.com/in/russellbrunson/
Russell’s Instagram: www.instagram.com/russellbrunson
Resources Mentioned:
Russell’s YouTube: www.youtube.com/@russellbrunson
The 12 month millionaire Droplets: Vincent James's Unmissable Revelations by Vincent James: https://www.amazon.com/month-millionaire-Droplets-Unmissable-Revelations/dp/B0CXJGPXNN
Dig Your Well Before You're Thirsty: The Only Networking Book You'll Ever Need by Harvey Mackay: https://www.amazon.com/Your-Well-Before-Youre-Thirsty/dp/0385485468
Leap Academy:
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Known for seizing “big, scary opportunities,” Bryan Power has defined his career by embracing risk, adapting to change, and staying focused under pressure. After turning down a promotion at Google for a new challenge at Square, he quickly realized he was in over his head. But it was in facing that discomfort head-on, that he experienced his most significant growth moments. In this episode, Bryan joins Ilana to discuss the importance of tackling challenging opportunities, the practices that lead to career growth, and his unique approach to leadership.
Bryan Power is a certified executive coach with over 20 years of experience in human resources management. Having worked with top companies like Google, Yahoo!, Square, and Nextdoor, he specializes in guiding leaders through growth, high-stakes transitions, and fast-paced environments.
In this episode, Ilana and Bryan will discuss:
(00:00) Introduction
(00:22) His Journey to Silicon Valley
(01:31) Big, Scary Opportunities that Drove His Growth
(03:45) Bryan’s Annual Growth Reflection Ritual
(05:29) Transitioning from Google to Square
(08:40) The Weight of Leadership in Today’s World
(10:18) How COVID-19 Impacted the Way We Work
(12:37) The Pros and Cons of Remote Work
(16:52) Why Adversity Makes the Best Leaders
(20:05) How Bryan’s Background Influenced His Success
(22:46) Bryan’s Secret to Landing Your Dream Job
(25:57) Key Skills Every New Leader Must Master
(29:54) Building Trust in Your First 90 Days at a New Job
(34:41) Nextdoor’s Success in Digital Community Building
(39:37) Career Lessons Bryan Wishes He Had Learned Sooner
Bryan Power is a certified executive coach with over 20 years of experience in human resources management. Having worked with top companies like Google, Yahoo!, Square, and Nextdoor, he specializes in guiding leaders through growth, high-stakes transitions, and fast-paced environments. Bryan has a proven track record of building and leading high-performing teams across North and South America, Europe, the Middle East, Australia, and Asia. His expertise extends to board-level work, where he has developed executive compensation strategies, company-wide cash/equity incentives, and benefits programs.
Connect with Bryan:
Bryan’s LinkedIn: www.linkedin.com/in/bryanpower
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.
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Andrew Lacy stumbled into entrepreneurship after failing to land a tech job. His first company did so well that he eventually sold it to Disney. Believing he had business all figured out, he launched another company, only to realize that success wasn’t guaranteed. For his next venture, Prenuvo, Andrew took a more thoughtful approach, but investors repeatedly rejected the idea. Determined to make it work, he bootstrapped and secured loans to launch a clinic in Silicon Valley. Today, Prenuvo is revolutionizing preventive healthcare. In this episode, Andrew shares valuable insights on reinventing yourself, making bold career changes, and pushing through setbacks to bring innovative ideas to life.
Andrew Lacy is an Australian serial entrepreneur, angel investor, and the founder/CEO of Prenuvo, a pioneering health tech company using whole-body imaging for early disease detection, including cancer.
In this episode, Ilana and Andrew will discuss:
(00:00) Introduction
(00:35) From Lawyer to Accidental Tech Entrepreneur
(06:44) Lessons from His First Business
(13:19) The Pains and Gains of Having a Co-founder
(14:59) Starting a Company, Again?
(17:24) Cultural Differences in Entrepreneurship
(19:57) Tough Truths About Building a Startup
(22:44) The Health Scan That Birthed Prenuvo
(28:33) Dealing with Investor Rejection
(35:11) The Future of Healthcare with Prenuvo
(36:35) A Surprising Fact About Andrew
(37:56) His Hack for Aspiring Entrepreneurs
Andrew Lacy is an Australian serial entrepreneur, angel investor, and founder/CEO of Prenuvo, a pioneering health tech company using whole-body imaging for early disease detection, including cancer. He envisions a future where healthcare is more affordable and accessible, and where people embrace health screenings as tools for long-term wellness. Andrew also co-founded Tapulous, a key player in the early iPhone app ecosystem, later acquired by Disney. He has held leadership roles at McKinsey and Disney.
Connect with Andrew:
Andrew’s Website: https://andrewlacy.com/
Andrew’s LinkedIn: https://www.linkedin.com/in/andrewllacy/
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.
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Dan Ariely didn’t just accept the hand life dealt him. He turned it into something powerful. After a traumatic burn accident that scarred 70% of his body, he struggled to find his place in the world. This journey led him to study human psychology and behavior, focusing on how people cope with pain and trauma. Later, when false rumors spread about him on social media, Dan chose to understand and empathize with the “misbelievers.” In this episode, Dan joins Ilana to share his journey from personal trauma to professional triumph, exploring how lies, rumors, and "misbelief" take root and affect lives, and what he’s learned by going through it all firsthand.
Dan Ariely is a three-time New York Times bestselling author and Professor of Psychology & Behavioral Economics at Duke University. His personal experience as a burn survivor has influenced his approach to understanding human behavior. His latest book, Misbelief, explores how false beliefs form and how to challenge them.
In this episode, Ilana and Dan will discuss:
(00:00) Introduction
(00:28) The Story Behind the Iconic Half Beard
(04:46) Turning Personal Pain into Professional Purpose
(09:07) From Burn Victim to Social Scientist
(14:49) Confronting Death Threats and Conspiracy Theorists
(17:54) How Stress Fuels Misbelief
(25:05) How Online Hate Turns to Moral Outrage
(31:50) Navigating Trust, Risk, and Failure in Leadership
(37:51) How Technology Is Making Us Worse
(41:07) Dan’s 45-Minute Work Ritual for Better Productivity
(43:43) Life Lessons on Finding Your True Strengths
Dan Ariely is a three-time New York Times bestselling author and Professor of Psychology & Behavioral Economics at Duke University. Known for his research on irrational behavior and decision-making, he’s advised companies like Google, Apple, and governments worldwide. His books Predictably Irrational, The Upside of Irrationality, and The Honest Truth About Dishonesty, have been translated into 30+ languages, and his work inspired NBC’s The Irrational. As a burn survivor, Dan’s personal experience has influenced his approach to understanding human behavior. His latest book, Misbelief, explores how false beliefs form and how to challenge them.
Connect with Dan:
Dan’s Website: https://danariely.com
Dan’s LinkedIn: https://www.linkedin.com/in/danariely
Resources Mentioned:
Dan’s Book, Misbelief: What Makes Rational People Believe Irrational Things: https://www.amazon.com/Misbelief-Rational-People-Believe-Irrational/dp/0063280426
Dan’s Book, The Honest Truth About Dishonesty: How We Lie to Everyone--Especially Ourselves: https://www.amazon.com/Honest-Truth-About-Dishonesty-Everyone-Especially/dp/0062183613
NBC Show: The Irrational: https://www.imdb.com/title/tt16288838/
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.
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Howard Behar went from making $300,000 a year to working at Starbucks for a third of that. Driven by his passion for the business, he rose to become president of Starbucks North America and later the founding president of Starbucks International, helping grow the company from 28 to over 15,000 stores worldwide. Despite these achievements, Howard faced a deep depression after retiring, prompting him to reevaluate his life’s purpose. He realized that his true calling is to serve and uplift others, with or without a formal title. In this episode, Howard chats with Ilana about redefining purpose after retirement, finding identity beyond titles, and why he believes in putting people before profits.
Howard Behar is a speaker, advisor, mentor, bestselling author, former president of Starbucks North America, and founding president of Starbucks International. He champions the philosophy that businesses should focus on people rather than products.
In this episode, Ilana and Howard will discuss:
(00:00) Introduction to Howard Behar
(01:12) Howard's Rock Bottom Moment
(02:31) Rediscovering Life's Work
(06:29) Childhood and Family Background
(08:27) Lessons from the Family Grocery Store
(09:40) Joining Starbucks
(14:25) The People-Centric Philosophy
(17:39) Reviving the 'We' Culture at Starbucks
(25:51) The Four Rules of Leadership
(26:06) Listening to Your Team
(26:43) The Birth of the Frappuccino
(30:15) Overcoming Challenges as a Leader
(37:29) The Importance of Core Values
(43:11) The Six P's of Success
Howard Behar is a speaker, advisor, mentor, bestselling author, former president of Starbucks North America, and founding president of Starbucks International. He champions the philosophy that businesses should focus on people rather than products. His impactful leadership principles include memorable lessons like, “The person who sweeps the floor should choose the broom.” He is the author of It’s Not About the Coffee and The Magic Cup, and he continues to share his insights globally with leaders and students.
Connect with Howard:
Howard’s Website: http://howardbehar.com/
Howard’s LinkedIn: https://www.linkedin.com/in/howard-behar
Howard’s Email: [email protected]
Howard’s Phone: 206-972-7776
Resources Mentioned:
Servant Leadership: A Journey into the Nature of Legitimate Power and Greatness by Robert K. Greenleaf: https://www.amazon.com/Servant-Leadership-Legitimate-Greatness-Anniversary/dp/0809105543
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.
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In a world that imposes expectations, Lisa Bilyeu is all about defying them. Raised in a traditional Greek Orthodox family, her path was set: get married and raise a family. But after eight years as a stay-at-home wife, she could no longer ignore the inner voice telling her she was meant for more. So, she co-founded Quest Nutrition with her husband and built a billion-dollar business. In this episode, Lisa talks to Ilana about setting ambitious goals, trusting your decisions, and finding self-worth without needing external validation.
Lisa Bilyeu is a renowned entrepreneur, bestselling author, and co-founder of Quest Nutrition, a multi-billion-dollar company. Her mission is to use content creation to empower women to break free from limiting beliefs and unlock their full potential.
In this episode, Ilana and Lisa will discuss:
(00:00) Introduction
(01:56) The Drip Effect: How Beliefs Shape Us
(04:54) Breaking Free from the “Velvet Handcuffs”
(06:26) The Trap of People-Pleasing and Toxic Gratitude
(09:08) Learning Leadership Through Trial, Error, and Rap Music
(10:00) From Housewife to Entrepreneur
(17:30) Handling Your Emotions in Business
(24:30) How Lisa Tackles Online Hate with Grace
(31:40) Crafting a Clear Mission Using the “Who, What, Why” Method
(37:30) Lisa’s No-BS Guide to Success
(40:03) The Importance of Practice
(44:45) Why I Chose My Mission Over Motherhood
(01:01:23) The Tough Moment That Empowered Her
(01:06:49) The Reality of Happiness
Lisa Bilyeu is a renowned entrepreneur, best-selling author, and co-founder of Quest Nutrition, a multi-billion-dollar company that transformed the health and wellness industry. She is also the founder and host of Women of Impact, co-founder of Impact Theory, and bestselling author of Radical Confidence. Lisa’s mission is to use content creation to empower women to break free from limiting beliefs and embrace their full potential.
Connect with Lisa:
Lisa’s Website: https://lisabilyeu.com/
Lisa’s YouTube: www.youtube.com/@LisaBilyeu
Lisa’s Instagram: https://www.instagram.com/lisabilyeu
Resources Mentioned:
Lisa’s Book, Radical Confidence: 11 Lessons on How to Get the Relationship, Career, and Life You Want: https://www.amazon.com/Radical-Confidence-No-BS-Lessons-Becoming-ebook/dp/B09JPHK9C3
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 -
Convinced that technology was the future of advertising, David Jones set out to build Brandtech. But again and again, investors rejected his model, doubting the potential of AI and digital technology in an industry where traditional models worked so well. Despite countless ‘no’s,’ David pressed on, believing he could redefine the industry. And that's exactly what he did. Today, he leads a billion-dollar company that blends tech and creativity to reshape advertising. In this episode, David shares actionable advice on staying resilient in the face of doubt, innovating in a traditional industry, and building a brand that stands out.
David Jones is a serial entrepreneur, bestselling author, and founder of The Brandtech Group, a pioneering digital and Gen AI marketing company. He is also the co-founder of One Young World, a global organization empowering young leaders to drive social and environmental change.
In this episode, Ilana and David will discuss:
- His 180° shift from sports to advertising
- The audacious cold call that got his foot in the door
- Climbing to the top by breaking every rule
- Finding courage by imagining the worst
- Stepping back to leap forward
- Taking Australia’s digital ad scene by storm
- Defying naysayers to bring AI to ads
- Going from countless ‘no’s’ to billions in revenue
- Why he’s all-in on empowering young leaders
- How Brandtech is using AI to reinvent ads
- The business case for ‘doing good’ in the world
- Using your privilege to make an impact
- Turning vision into action
- How excellent storytelling creates opportunities
- And other topics…
David Jones is a serial entrepreneur, bestselling author, and founder of The Brandtech Group, a pioneering digital and Gen AI marketing company. Previously, he became the youngest global CEO in advertising history, leading Havas and Havas Worldwide, and was the only British CEO of a publicly traded French company. In 2009, he co-founded One Young World, a global organization empowering young leaders to drive social and environmental change. He also collaborated on Kofi Annan's TckTckTck Campaign for climate justice and has advised numerous high-profile leaders.
Connect with David:
David’s Website: https://thebrandtechgroup.com/
David’s LinkedIn: https://www.linkedin.com/in/davidjonesoyw/
David’s Twitter: https://x.com/davidjonesOYW
Resources Mentioned:
David’s Book, Who Cares Wins: Why Good Business is Better Business: https://www.amazon.com/Who-Cares-Wins-business-Financial/dp/0273762532
One Young World: https://www.oneyoungworld.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 -
Harley Finkelstein didn’t set out to be an entrepreneur. He had no choice. With his father out of the picture, he had to pay for university and support his mother and sisters. So, he turned to his go-to problem-solving tool: entrepreneurship. Starting a t-shirt business changed his life, eventually leading him to Shopify, where he became one of their first merchants and later, its president. In this episode, Harley shares his incredible journey, highlighting key lessons on how entrepreneurship can solve real-life problems and the power of adapting quickly in a fast-changing world.
Harley Finkelstein is the President of Shopify. He is also an entrepreneur, lawyer, and investor. He is one of the “Dragons” on CBC’s Next Gen Den and has been recognized among Canada’s Top 40 Under 40 and Fortune’s 40 Under 40.
In this episode, Ilana and Harley will discuss:
- His early roots in entrepreneurship
- The t-shirt business that changed his life
- How he set himself apart by overdelivering
- Entrepreneurship as a tool for problem-solving
- Why you must thrive in rapid change to stay relevant
- Embracing ‘founder mode’ by focusing on the details
- Why the future of entrepreneurship is limitless
- How he became one of the first Shopify users
- How Shopify built a mission-aligned culture
- Finding your life’s work
- And other topics…
Harley Finkelstein is an entrepreneur, lawyer, and President of Shopify. He is an advisor to Felicis Ventures and a notable investor. He has been recognized as Canadian Angel Investor of the Year and among Canada's Top 40 Under 40. As one of the "Dragons" on CBC's Next Gen Den, Harley brings his wealth of knowledge and experience to the forefront. His leadership extends beyond Shopify, having been on the Board of Directors for the C100 and the CBC. He’s also a proud member of the Order of Ottawa and currently serves on the board of Operation Hope, focusing on financial literacy empowerment.
Connect with Harley:
Harley’s Website: http://harleyf.com/about/
Harley’s LinkedIn: https://www.linkedin.com/in/harleyf/?originalSubdomain=ca
Harley’s Twitter: https://twitter.com/harleyF
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 -
From struggling in school because of his dyslexia to starting a magazine at just 15, Richard Branson has always found ways to turn his challenges into unique opportunities. Even his iconic airline started as a joke when he was stranded in Puerto Rico after his canceled flight. He hired a plane, wrote "Virgin Airlines" on a blackboard, and offered seats to other stranded passengers. Soon enough, Virgin Atlantic was born. In this episode, Richard shares his incredible journey with Ilana, highlighting key lessons on embracing risk, staying resilient, and using challenges to fuel growth and innovation.
Sir Richard Branson is the founder of Virgin Group, spanning airlines, cruises, hotels, health, entertainment, and space travel. Known for his adventurous spirit and bold pursuits, he has not only transformed industries but also used his influence to champion global humanitarian causes.
In this episode, Ilana and Richard will discuss:
- Surviving British boarding school
- Quitting school at 15 to launch a magazine
- Partnering with people who share his vision
- The joke that led to the creation of Virgin Airlines
- Building the world’s largest independent record label
- Facing risk with excitement, not fear
- Tackling world problems as an entrepreneur
- Saving hostages from Saddam Hussein's regime
- Forming a peacekeeping council of global elders
- Pushing through the toughest days
- Dyslexia as a superpower for thinking differently
- And other topics…
Sir Richard Branson is a serial entrepreneur and founder of the Virgin Group, which includes more than 40 Virgin companies operating in 35 countries. At just 15, he dropped out of school and started Student magazine, which focused on youth culture. He went on to launch Virgin Records, signing iconic artists like Mike Oldfield and the Sex Pistols. Known for his bold ventures, Branson started Virgin Atlantic in 1984 and Virgin Galactic in 2004. Through Virgin Unite, he leads philanthropic efforts by using business to drive positive change globally.
Connect with Richard:
Richard’s Website: https://www.virgin.com/branson-family/richard-branson
Richard’s LinkedIn: https://www.linkedin.com/in/rbranson/
Richard’s Twitter: https://x.com/richardbranson
Resources Mentioned:
Richard’s Audiobook: Losing and Finding My Virginity: The Full Story: https://www.amazon.com/Losing-Finding-My-Virginity-Story/dp/B0CW8BS7W7
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 Dudan started his first business in college, painting apartments to pay the bills. The business grew beyond his expectations, allowing him to support his younger brother and create jobs for other college athletes. Years later, he moved to South Florida to help with disaster recovery after Hurricane Andrew struck. Having learned to see opportunity in adversity, he started AdvantaClean, which eventually grew into a national franchise. In this episode, Jeff talks to Ilana about spotting hidden opportunities in crises and the mindset shifts that helped him build a successful franchise business to empower others.
Jeff Dudan is a franchise executive and the CEO of Homefront Brands. He brings decades of experience in funding, building, and scaling franchises to help others succeed in the industry. As a published author and host of The Homefront Podcast, Jeff also appeared on CBS’s Undercover Boss.
In this episode, Ilana and Jeff will discuss:
- Starting a business in college
- Pushing past your limitations
- Grabbing opportunities as they come
- Building Homefront to help franchise owners
- Lessons from his father’s business challenges
- Setting clear roles to make partnerships work
- Creating a unique franchise model
- Figuring out the right time to start franchising
- Leading franchisees with patience
- Why businesses are high-class assets
- Using real estate to fund his business
- The CEO’s role in setting standards
- Saying “yes” to chances for visibility
- Aligning your values with your business
- And other topics…
Jeff Dudan is the CEO of Homefront Brands, a published author, and a franchise executive with 25 years of experience building and scaling franchise businesses. He founded AdvantaClean in the aftermath of Hurricane Andrew, growing it from a disaster recovery business to a franchise with over 240 locations before it was acquired. Jeff is a Forbes contributor and host of The Homefront Podcast, where he explores the world of franchising and leadership. He has also appeared on CBS’s Undercover Boss. He has worked with organizations like Novant Health, the IFA Franchisor Forum, and St. Jude Children's Research Hospital.
Connect with Jeff:
Jeff’s Website: https://jeffdudan.com/
Jeff’s LinkedIn: https://www.linkedin.com/in/jeffdudan/
Resources Mentioned:
Jeff’s Episode on Undercover Boss: https://www.imdb.com/title/tt6432766/
Jeff’s Books:
Discernment: The Business Athlete's Regimen for a Great Life through Better Decisions: https://www.amazon.com/Discernment-Business-Athletes-Regimen-Decisions/dp/1544508506
Hey, Coach! https://www.amazon.com/Hey-Coach-Jeff-Dudan/dp/1511990570
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 -
One day, while watching her baby somersault, Katrina Spade thought about how quickly time flies. Then it hit her like a ton of bricks that she would be in her 70s by the time he turned 40. This reflection sparked an interest in the funeral industry, ultimately leading her to design a new death experience. Despite facing legal hurdles and industry challenges, she founded the world’s first human composting company. In this episode, Katrina shares how she turned a simple grad school project into a groundbreaking business. She also highlights the key lessons she learned, from challenging norms to embracing big ideas.
Katrina Spade is the founder and CEO of Recompose, the world’s first human composting company. Combining her background in architecture with a deep respect for nature, she created an eco-friendly alternative to traditional funerals.
In this episode, Ilana and Katrina will discuss:
- How a grad school project sparked a revolutionary idea
- Balancing big ideas with practical execution
- Translating design skills into business
- Telling your story to test your ideas
- Why ‘perfect’ is the enemy of ‘good’
- How she quit her job and funded her dream
- Attracting investors who believe in your vision
- Building a reputation with intention and strategy
- Breaking legal barriers to disrupt death care
- And other topics…
Katrina Spade is the founder and CEO of Recompose, the world’s first human composting company, which offers an eco-friendly alternative to traditional burials and cremation. With a background in architecture and sustainable design, she created a groundbreaking method to transform human bodies into soil. In 2019, she successfully advocated for the legalization of human composting in Washington, and by 2020, Recompose had opened its first facility. Katrina has been featured in major outlets like NPR, Fast Company, and The New York Times. She is also a recipient of prestigious fellowships from Echoing Green and Ashoka.
Connect with Katrina:
Katrina’s LinkedIn: https://www.linkedin.com/in/katrina-spade-37047439/
Katrina’s Instagram: https://www.instagram.com/katrinaspade/
Resources Mentioned:
Recompose: https://recompose.life/
Big Magic: Creative Living Beyond Fear by Elizabeth Gilbert: https://www.amazon.com/Big-Magic-Creative-Living-Beyond/dp/1594634726
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 -
Russ Ruffino spent his 30th birthday sobbing into his bourbon because he felt like a failure. He had spent the last decade bartending while clinging to his dream of becoming a movie star. So, how did he go from bartender to CEO of a $100 million business? He took his first step by applying his acting skills to writing persuasive sales copy. In this episode, Russ shares his incredible journey, offering lessons on leveraging unique skills, taking bold risks, and building a values-driven team to build a thriving business.
Russ Ruffino is the founder and CEO of Clients on Demand, a company that has generated over $100 million in revenue. He helps entrepreneurs, coaches, and consultants attract their ideal clients at the right price, anytime they want.
In this episode, Ilana and Russ will discuss:
- Translating his acting skills into compelling sales copy
- Taking the plunge into entrepreneurship
- Going from zero to $250K
- Scaling from small offers to a $100M empire
- The problem with scaling too quickly
- Why marrying the right person is a superpower
- Building a solid team by focusing on mission
- Why your company needs a "no jerks" policy
- Accepting that obstacles will come
- His rule of thumb for firing people
- Why entrepreneurs need acting classes
- Celebrating wins and enjoying the journey
- And other topics…
Russ Ruffino is the founder and CEO of Clients on Demand, a high-ticket sales company that has generated over $100 million in revenue by helping entrepreneurs scale their businesses. After struggling as an actor and bartender for a decade, Russ discovered online marketing. He took the plunge into entrepreneurship and today, he helps coaches, consultants, and service providers attract the right clients, at the right price, anytime they want.
Connect with Russ:
Russ’s Website: https://russruffino.com/
Russ’s LinkedIn: https://www.linkedin.com/in/russruffino/
Resources Mentioned:
The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Timothy Ferriss: https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357
The Ultimate Sales Letter: Attract New Customers. Boost your Sales. by Dan S Kennedy: https://www.amazon.com/Ultimate-Sales-Letter-Attract-Customers/dp/1440511411
How to Get Rich: One of the World's Greatest Entrepreneurs Shares His Secrets by Felix Dennis: https://www.amazon.com/How-Get-Rich-Greatest-Entrepreneurs/dp/1591842719 -
Chris Voss excelled as a lead FBI international kidnapping negotiator. At the start of his career, he thought it was all about being tough and direct. But over time, he discovered the secret to cracking negotiations—tactical empathy. Today, he teaches business leaders how to read emotions, build trust, and avoid leaving money on the table. In this episode, Chris explains why empathy is a world-changing skill and shares tactics for getting what you want in business and life.
Chris Voss is a former FBI hostage negotiator with over two decades of experience in high-stakes crisis negotiations. He's the CEO of Black Swan Group and author of Never Split the Difference.
In this episode, Ilana and Chris will discuss:
- How Chris became an FBI hostage negotiator
- Why empathy is the secret weapon in business and life
- Turning a “no” into a powerful negotiation tool
- Why decision-making is emotional
- The surprising power of vulnerability in negotiations
- “It's not what you say, it's how you say it”
- Why a positive frame of mind makes you 31% smarter
- How to get your boss to pay you more
- And other topics…
Chris Voss is a former FBI lead international kidnapping negotiator and expert in high-stakes negotiations. He is also the CEO of Black Swan Group and author of Never Split the Difference. With over 24 years of experience at the FBI, Chris negotiated some of the most challenging hostage situations. He represented the U.S. at G8-sponsored international conferences on kidnapping. Chris has received prestigious awards, including the Attorney General’s Award for Excellence in Law Enforcement. He has also taught negotiation in top MBA programs at USC, Georgetown, and Harvard, as well as lecturing globally.
Connect with Chris:
Chris’s LinkedIn: https://www.linkedin.com/in/christophervoss/
Chris’s Twitter: https://twitter.com/fbinegotiator
Resources Mentioned:
Chris’s Book, Never Split the Difference: Negotiating As If Your Life Depended On It: https://www.amazon.com/Never-Split-Difference-Negotiating-Depended/dp/0062407805
Chris’s Documentary, Tactical Empathy: https://www.imdb.com/title/tt21383310/
Chris’s YouTube: https://www.youtube.com/channel/UCk7jHqdlFFDBhC1QIFqi54w
Negotiation Mastery Newsletter: https://www.linkedin.com/newsletters/negotiation-mastery-6998634991547006976/
Shawn Achor’s TED Talk, “The Happy Secret to Better Work”: https://www.youtube.com/watch?v=fLJsdqxnZb0
The Talent Code: Greatness Isn't Born. It's Grown. Here's How. by Daniel Coyle: https://www.amazon.com/Talent-Code-Greatness-Born-Grown/dp/055380684X
In the Presence of My Enemies by Gracia Burnham and Dean Merrill: https://www.amazon.com/Presence-My-Enemies-Gracia-Burnham/dp/0842381392 -
Before building a global snack empire, Anne Beiler’s dream was to have her own family like the loving one she grew up in. Like a fairytale, she met the man of her dreams. But years later, she found herself stuck in a place of darkness after tragically losing her daughter and enduring years of abuse. Through this pain, however, Anne found a new purpose. With no money, no formal education, and no business plan, she started the iconic pretzel brand, Auntie Anne’s. In this episode, Anne shares powerful lessons on resilience, leadership, and embracing life’s obstacles.
Anne Beiler is the founder of Auntie Anne's, the world's largest pretzel franchise, with over 2,000 locations in more than 25 countries. She now dedicates her time to speaking and writing, teaching others how to overcome tough times, be strong leaders, and find purpose in life, even through pain.
In this episode, Ilana and Anne will discuss:
- How Anne’s background shaped her work ethic and values
- Scaling her pretzel stand into a global brand
- Balancing personal pain with building a business
- Staying grounded under pressure
- Why your people are your greatest asset
- Lessons Anne learned while growing her franchise
- How vulnerability became her strength
- Anne’s advice for thriving through tough times
- Building a lasting legacy through business
- The power of purpose in achieving success
- Why authentic leadership matters
- And other topics…
Anne Beiler is a self-made entrepreneur and the founder of Auntie Anne’s, the globally recognized pretzel franchise. Raised in an Amish-Mennonite family, Anne faced devastating personal challenges, like losing her daughter and enduring years of abuse. She started her business to support her husband’s vision of providing free family counseling. Despite having no business plan or formal education, she scaled Auntie Anne’s into a multimillion-dollar business. Her franchise now spans over 25 countries with over 2,000 locations. Today, Anne speaks globally on overcoming adversity, leadership, and the role of faith in business.
Connect with Anne:
Anne’s Website: https://auntieannebeiler.com/
Anne’s Facebook: https://www.facebook.com/auntieannebeiler/ -
Early in his career, Scot was told that he wasn’t “tough enough” for the media industry. He didn’t fit the traditional image of a hard-nosed executive. But instead of changing who he was, Scot embraced his own authentic style of leadership, ultimately proving that enthusiasm and a focus on collaboration are just as powerful for success. He went on to lead groundbreaking marketing campaigns for major networks like CNN and HLN. In this episode, Scot shares his leadership lessons from building a successful career by staying true to himself.
Scot Safon is a seasoned media executive who led marketing and branding efforts for major networks like CNN, HLN, and The Weather Channel. Known for overseeing award-winning marketing campaigns, he now consults for top brands, helping to shape their marketing strategies.
In this episode, Ilana and Scot will discuss:
- Turning passion into a career advantage
- Embracing your true self in a tough industry
- Scot’s rise to leading CNN’s marketing
- Building a career without industry connections
- Staying resilient when facing setbacks
- The importance of collaborative leadership
- How to empower teams and inspire creativity
- Turning failures into growth opportunities
- How Scot controls panic attacks while speaking publicly
- Balancing creativity with business demands
- Building a career that aligns with your passion
- Finding fulfillment in a competitive industry
- And other topics…
Scot Safon is a seasoned media executive known for his leadership roles at major networks like CNN, HLN, and The Weather Channel. As Chief Marketing Officer of CNN, he oversaw award-winning campaigns for programs like Anderson Cooper 360 and Larry King Live. Under his leadership, CNN's marketing efforts during major events such as the 2008 Presidential Elections and Hurricane Katrina received critical acclaim. Later, as the President of HLN, Scot revamped the network, leading to its growth through shows like Morning Express with Robin Meade. He also served as EVP and CMO of The Weather Channel, where he further honed his expertise in media branding. Today, he consults for major brands, helping companies shape their marketing strategies through his extensive experience in media and branding.
Connect with Scot:
Scot’s LinkedIn: https://www.linkedin.com/in/scotsafon/ -
Fascinated with science as a young child, Kira Radinsky was driven to make a meaningful impact on the world through technology. She faced rejection after rejection while building her first startup, but her resilience paid off when eBay acquired the company. Kira didn’t stop there—she developed AI models that successfully predicted cholera outbreaks in Cuba and today, she continues to push the boundaries of AI and healthcare. As inspiring as her journey is, it’s been far from easy. In this episode, Kira shares the lessons she’s learned about resilience, pushing past rejection, and scaling startups.
Kira Radinsky is the CEO and CTO of Diagnostic Robotics, known for her pioneering work in AI and predictive analytics. She gained global recognition for developing models that forecast major events, earning her recognition on Forbes’ 30 Under 30 and MIT Technology Review's 35 Innovators Under 35.
In this episode, Ilana and Kira will discuss:
- How Kira built her first company despite major challenges
- How AI is transforming global healthcare
- The mindset shifts that fuel entrepreneurial success
- Turning failures into career-defining moments
- How to push forward when no one believes in your vision
- Making bold leaps in a male-dominated industry
- Staying committed when the path gets tough
- Lessons from selling a startup to eBay
- The power of persistence in scaling a business
- Finding opportunity in uncertainty
- Leveraging data to predict and prevent crises
- Navigating risk and uncertainty with confidence
- And other topics…
Kira Radinsky is the CEO and CTO of Diagnostic Robotics, an AI-driven healthcare company. Known for her groundbreaking work in data mining and predictive analytics, she gained international recognition for developing predictive models that forecast global events like disease outbreaks and political unrest, including predicting a cholera outbreak in Cuba. Kira began her studies at the Technion-Israel Institute of Technology at just 15 years old, later earning her PhD. She co-founded SalesPredict, an AI-driven company that was acquired by eBay in 2016, where she served as Chief Scientist and Director of Data Science. She has been honored in Forbes' 30 Under 30 and has been named one of MIT Technology Review's 35 Innovators Under 35.
Connect with Kira:
Kira’s LinkedIn: https://www.linkedin.com/in/kira-radinsky/
Resources Mentioned:
Diagnostic Robotics Website: https://www.diagnosticrobotics.com -
Frustrated by how women’s voices were being ignored in the corporate world, Sally Helgesen started documenting the leadership styles of successful women. Her efforts culminated in the groundbreaking book, The Female Advantage, which changed the course of her career. Despite the uncertainty, Sally left her dream job for the male-dominated space of leadership coaching and speaking. Today, she is recognized as the world’s premier women’s leadership expert. In this episode, Sally shares powerful leadership lessons and offers actionable advice on pushing past fear, dealing with pushback, and staying committed to your mission.
Sally Helgesen is an internationally recognized expert in women’s leadership. She has authored several books, including her latest, Rising Together. Sally has been inducted into the Thinkers50 Hall of Fame and her work has appeared in The New York Times and Fortune, among others.
In this episode, Ilana and Sally will discuss:
- Why you must act before you feel ready
- How women’s leadership styles differ and why they matter
- How Sally’s frustration became a career-changing mission
- Navigating pushback while staying focused
- Discomfort as a catalyst for growth
- The evolving definition of good leadership
- Why success hinges on staying mission-focused
- Sally’s tips for building a tough skin
- Following your gut when making big decisions
- Strategies for building credibility in new, uncertain environments
- Why inclusive leadership benefits everyone, not just women
- Pushing past fear to seize golden opportunities
- And other topics…
Sally Helgesen is a speaker, coach, bestselling author, and internationally recognized expert in women’s leadership. She has authored several books, including her latest, Rising Together, and the bestseller, How Women Rise, co-authored with Marshall Goldsmith. She has worked with organizations worldwide, from Microsoft to The World Bank Group, to cultivate inclusive cultures. Sally’s groundbreaking work has appeared in The New York Times, Fortune, and Harvard Business Review, among others. She has also been inducted into the Thinkers50 Hall of Fame, honoring her significant contributions to the field of leadership and management worldwide.
Connect with Sally:
Sally’s Website: https://sallyhelgesen.com/
Sally’s LinkedIn: https://www.linkedin.com/in/sallyhelgesen/
Resources Mentioned:
The Female Advantage: Women’s Ways of Leadership: https://www.amazon.com/Female-Advantage-Womens-Ways-Leadership/dp/0385419112
How Women Rise: Break the 12 Habits Holding You Back from Your Next Raise, Promotion, or Job: https://www.amazon.com/How-Women-Rise-Breaking-Behaviors/dp/0316440124
Rising Together: How We Can Bridge Divides and Create a More Inclusive Workplace: https://www.amazon.com/Rising-Together-Divides-Inclusive-Workplace/dp/0306828308
The Female Vision: Women's Real Power at Work: https://www.amazon.com/Female-Vision-Womens-Real-Power/dp/1576753824
The Web of Inclusion: Architecture for Building Great Organizations: https://www.amazon.com/Web-Inclusion-Architecture-Building-Organizations/dp/1587982773 - もっと表示する
