Jim McKelvey did the impossible. He beat Amazon. The tech giant launched a product similar to Square’s, undercut their pricing, and leveraged its massive brand. Everyone thought Square was doomed. But a year later, Amazon quit and even mailed Square readers to their customers. That left Jim with a bigger question: “How did we survive when no one else ever has?” The search for that answer inspired his book The Innovation Stack, a blueprint for building a business that cannot be copied. In this episode, Jim joins Ilana to reveal the secret to creating an unbeatable business, why ignorance can be a superpower, and how to survive the impossible as an entrepreneur. Jim McKelvey is the co-founder of Square (now Block), a billionaire entrepreneur, and author of The Innovation Stack. He also founded LaunchCode, a nonprofit providing free tech education and job placement. In this episode, Ilana and Jim will discuss: (00:00) Introduction  (02:04) Growing Up as an ‘Uncool’ Kid in St. Louis (04:01) The Early Hustle That Jumpstarted His Career (07:47) Launching a Business with 15-Year-Old Jack Dorsey (13:50) The Birth of Square: From Glass Blowing to FinTech (20:09) The Art of Selling and Capturing Attention (26:48) How a Single Demo Won Over MasterCard (31:04) Amazon's Failed Attempt to Crush Square (32:17) The Innovation Stack: Building an Unbeatable Business (35:55) Why Most Entrepreneurs Give Up Too Soon (41:32) Why the Best Innovators Are Always “Unqualified” Jim McKelvey is a serial entrepreneur, inventor, and philanthropist best known as the co-founder of Square (now Block), the fintech company that redefined digital payments. He is the author of The Innovation Stack, which explores how companies can survive by creating solutions that can’t be copied. Jim also founded LaunchCode, a nonprofit that provides free tech education and job placement for aspiring coders.  Connect with Jim Jim’s LinkedIn: linkedin.com/in/mckelveyjim Resources Mentioned Jim’s Book, The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time: https://www.amazon.com/Innovation-Stack-Building-Unbeatable-Business/dp/0593086732 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

At a 2015 World Cup match in Vancouver, Kara searched nine stores for her daughters’ jerseys and found none. That spark of “joyful irritation” became a movement to build teams, build community, and build an industry. In this episode, Kara joins Ilana to share how that moment ignited Angel City FC, how she, along with her partners, managed to create one of the most valuable women’s soccer teams in the world, and why she embraces rejection as a growth strategy. She breaks down the tension between patience and urgency, the power of finding joy in pursuing one’s passions, and how to choose partners who amplify your mission. Kara Nortman is the co-founder of Angel City FC and managing partner of Monarch Collective, a $250M investment platform driving the growth of women’s sports. A former investor at Upfront Ventures and operator at IAC, Kara brings decades of experience turning bold ideas into lasting movements. In this episode, Ilana and Kara will discuss: (00:00) Introduction (02:03) Realizing the Market Gap in Women’s Sports (04:16) Turning Inspiration into Action (06:44) Finding Joy Through Volunteering and Community (11:54) The Birth of Angel City FC (17:23) Turning Rejection into Fuel (30:48) Breaking into the World of Venture Capital (31:42) Game-Changing Mentorship and Early Career Lessons (33:47) Discovering a Passion for Tech at Battery Ventures (44:19) Building Angel City and Redefining the Playbook (50:04) Launching Monarch and Scaling the Movement Kara Nortman is an investor, founder, and sports operator focused on advancing the women’s sports economy. As a co-founder of the professional women's soccer team, Angel City FC, she pioneered a community-first 10% sponsorship model that drove significant commercial success. Kara co-leads Monarch Collective, investing in women’s sports teams and related businesses across the U.S. and Europe. Previously, she was a managing partner at Upfront Ventures and an executive at IAC, where she helped incubate Tinder through Hatch Labs. Connect with Kara: Kara’s LinkedIn: linkedin.com/in/karanortman Resources Mentioned: Monarch Collective: https://monarchcoll.com Angel City FC: https://angelcity.com   Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

Robert Glazer collapsed in his kitchen in front of his son, convinced he was having a heart attack. In reality, it was a massive panic attack triggered by grinding too hard while starting a business, building a house, raising kids, and weathering the 2008 recession. That wake-up call forced him to reevaluate everything: his health, his leadership, and the values that guided his life. In this episode, Robert returns to the show to share how childhood struggles shaped his values, why passion is developed, not discovered, and how to know if you’re climbing the wrong mountain in life. He also reveals the frameworks from his new book to help you align your career, relationships, and purpose with your deepest values. Robert Glazer is a serial entrepreneur, bestselling author, and global keynote speaker. He founded Acceleration Partners, a 300-person marketing agency, and is the author of eight books, including Elevate and his newest release, The Compass Within. In this episode, Ilana and Robert discuss: (00:00) Introduction (02:09) Growing Up as the “Underachiever” Kid (05:20) Discovering a Love for Learning in College (09:00) How Helping One Company Sparked an Agency (10:30) The Health Scare That Sparked a Wake-Up Call (14:18) Leading with Transparency During COVID (16:56) Choosing to Step Aside as CEO (19:29) Writing The Compass Within as a Story (22:00) Understanding Core Values (26:09) The Three Climbs of Success for High Achievers (29:12) Six Questions to Identify Your Core Values Robert Glazer is an entrepreneur, bestselling author, and thought leader on business and personal growth. He founded Acceleration Partners, scaling it into a 300-person agency recognized for its values-driven culture. Robert is the author of eight books, including Elevate and The Compass Within, and the Friday Forward newsletter. Known for his insights on leadership, capacity building, and core values, he speaks on stages around the globe and helps individuals and organizations align success with authenticity. Connect with Robert Robert’s Website: robertglazer.com  Robert’s LinkedIn: linkedin.com/in/glazer   The Compass Within Website: compass-within.com Resources Mentioned LEAP Episode 32 with Robert Glazer: https://podcasts.apple.com/us/podcast/the-art-of-reinvention-how-to-elevate-your-career/id1701718200?i=1000660153819 The Six Core Values Questions: robertglazer.com/six Robert’s Book, The Compass Within: A Little Story About the Values That Guide Us: https://geni.us/values Free Course: robertglazer.com/compass-leap Robert’s Book, Elevate: Push Beyond Your Limits and Unlock Success in Yourself and Others: https://www.amazon.com/Elevate-Beyond-Limits-Success-Yourself/dp/1492691488  The Freak Factor: Discovering Uniqueness by Flaunting Weakness by David Rendall: https://www.amazon.com/Freak-Factor-Discovering-Uniqueness-Flaunting/dp/1599326698  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

Most people would assume that raising capital for a celebrity-backed business would be a cakewalk, but Thai Randolph knew that was far from the truth. Securing $100 million in investment for Kevin Hart's Hartbeat Productions required more than just a famous name; it took proving real value, building trust, and navigating rejection. Her success led to one of the largest private-equity rounds ever led by a Black woman in the U.S. In this episode, Thai joins Ilana to share the lessons she’s learned throughout her career, from her time at Sony, Facebook, and Lionsgate. She also opens up about her personal struggles with fertility while building a successful career and the pivotal moments that shaped her leadership style. Thai Randolph is an award-winning entrepreneur and marketer, and the former CEO of Hartbeat, where she led the company’s growth and secured a $100M investment, one of the largest private-equity rounds led by a Black woman in the U.S. In this episode, Ilana and Thai discuss: (00:00) Introduction (01:51) How Thai’s Small-Town Roots Shaped Her Path (04:58) Pivoting from Marketing Missiles to Storytelling (09:36) Breaking into Big Tech: From Sony to Facebook (14:14) Balancing Fertility Struggles and Career Moves (22:11) Joining Lionsgate and Meeting Kevin Hart (26:34) Challenges of Carving Out a New Business (28:20) Raising $100M for Hartbeat Against All Odds (32:40) Transitioning to CEO and Leadership Lessons (37:49) Balancing Work, Life, and Avoiding Burnout (41:57) Redefining Your Identity Beyond the Job Title (49:28) Thai’s Next Big Ventures and Future Plans Thai Randolph is an entrepreneur and marketer, and the former CEO of Hartbeat, where she led the company’s growth and secured a $100M investment, one of the largest private-equity rounds led by a Black woman in the U.S. As President and COO of Laugh Out Loud, she oversees the strategy and operations for Kevin Hart’s comedy network. Thai has driven digital transformation at companies like Facebook and Sony, and provided media strategy for top brands like Verizon, Dell, and more. Connect with Thai:  Thai’s LinkedIn: linkedin.com/in/thairandolph Thai’s Instagram: instagram.com/thairandolph Resources Mentioned: Thai’s Podcast, The Suga: podcasts.apple.com/us/podcast/the-suga/id1502324399  LOL Network: youtube.com/@lolnetwork  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 

For eight years, Lisa Bilyeu lived the life others expected: a traditional Greek wife focused on supporting her husband and running the home. But deep down, she knew she was meant for more. With no business background, zero confidence, and no clear roadmap, she decided to rewrite her story. She co-founded Quest Nutrition with her husband and built a billion-dollar business. In this LEAP Replay, Lisa opens up to Ilana about breaking free from cultural expectations, showing up authentically in the face of criticism, and how you can build radical confidence without needing external validation. Lisa Bilyeu is an 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 build extraordinary lives. In this episode, Ilana and Lisa will discuss: (00:00) Introduction  (02:22) Her Upbringing and the Weight of Expectations (06:44) Velvet Handcuffs: The Trap of People Pleasing (10:55) Transitioning from Housewife to Co-Founder (19:13) Handling Your Emotions in Business  (24:25) How Lisa Tackles Online Hate and Criticism (33:12) The Three Keys to Mission-Driven Content Creation (37:25) Lisa’s No-BS Guide to Success  (44:40) Why She Chose Her Mission Over Motherhood  (1:03:06) Building Radical Confidence Through Self-Reliance Lisa Bilyeu is an entrepreneur, 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/dp/B09JPHK9C3 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

As a teenager, Sir Richard Branson had already mastered the art of taking bold leaps to pursue opportunities. Dyslexic and struggling in school, he quit at age 15 to launch a youth magazine, a move that eventually led to Virgin Records, Virgin Atlantic, and the Virgin Group empire. In this LEAP Replay, Richard joins Ilana to share how he turned obstacles into opportunities, embraced fearless risk-taking, and uses his influence for international peace initiatives, all while showing that dyslexia can be a superpower. 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: (00:00) Introduction (02:10) Quitting School at 15 to Run a Magazine (05:26) Launching Virgin Records with a Bold Move (09:20) The Funny Moment That Birthed Virgin Atlantic (11:37) Using His Influence to Negotiate with Saddam Hussein (15:54) The “Reserve Tank” Mindset for Mental Toughness (18:17) Why Dyslexic Thinking Is a Superpower in Business Sir Richard Branson is a serial entrepreneur and founder of the Virgin Group, a global conglomerate of more than 40 companies spanning industries from entertainment to aviation and space travel. Known for his adventurous spirit and bold approach to business, Richard built Virgin into one of the world’s most recognized brands. Beyond entrepreneurship, he is a philanthropist, author of multiple bestsellers, and a passionate advocate for social and environmental causes. Connect with Richard: Richard’s Website: https://www.virgin.com/branson-family/richard-branson  Richard’s LinkedIn: linkedin.com/in/rbranson 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 fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

Ilana Golan knows what it feels like to lose everything. After climbing from the Air Force to Intel to VP in a Silicon Valley startup, she thought she had made it. But when a trusted co-founder cut her out of their new business overnight, she was left with nothing. No job, no company, no income, and a shattered ego. That collapse became the turning point, forcing Ilana to ask who she was without the titles and what kind of life she truly wanted to build. In this episode, Ilana breaks down the five shifts you need to reinvent your career and the blueprint she used to bounce back from failure, build one of the fastest-growing startups, and land opportunities with leaders like Richard Branson and GaryVee. Ilana Golan is a serial entrepreneur, keynote speaker, investor, and host of the LEAP Academy podcast. As the founder of LEAP Academy, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom.  In this episode, Ilana discusses: (00:00) Introduction (01:11) The Startup Collapse That Changed Everything (04:24) Losing Her Identity and Rebuilding From Scratch (06:22) Launching LEAP Academy and Reaching Startup of the Year (09:10) Reinvention as the Must-Have Skill of Our Era (10:09) The Power of Adaptability: IQ vs. EQ vs. AQ (11:29) The Five Shifts to Fast-Track Your Career (18:30) Commanding Authority: The Three Types of Branding  (23:17) Creating a Portfolio Career for Freedom and Wealth Ilana Golan is a serial entrepreneur, board director, global keynote speaker, and investor in over 100 companies. As the founder of Leap Academy, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom. Ilana has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Under her leadership, LEAP Academy was named one of Inc. 500’s Fastest Growing Companies. Connect with Ilana:  Ilana’s Website: leapacademy.com  Ilana’s LinkedIn: linkedin.com/in/ilanagolan  Ilana’s Email: ilana@leapacademy.com  Resources Mentioned: LEAP Academy Free Training: leapacademy.com/training  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

Despite outward success, Brad Feld struggled with depression, exhaustion, and feelings of emptiness. For years, he hid these challenges while relentlessly pushing forward as an entrepreneur. It wasn’t until his 40s, after seeking therapy and confronting his mental health, that Brad realized success wasn’t just about building companies, but about managing the emotional toll of entrepreneurship. Today, as the co-founder of Techstars and Foundry Group, he leads with a harmonious approach to work and life. In this episode, Brad joins Ilana to share the lessons he learned from early failures, why every successful founder faces ‘near-death moments’, and the mental health practices that helped him find joy again. Brad Feld is a venture capitalist, entrepreneur, and co-founder of Techstars, one of the world’s leading startup accelerators. He is also the co-founder of two venture capital firms, Foundry Group and Mobius Venture Capital. In this episode, Ilana and Brad discuss: (00:00) Introduction (01:07) Growing Up in Dallas and Discovering Computers (07:29) MIT Years and Early Startup Failures (14:17) Why Every Startup Faces a Near-Death Experience (16:54) Battling Fear, Shame, and Depression in His Twenties (26:52) Breaking Down at 47 Despite “Having It All” (29:05) Brad’s Practical Steps for Rediscovering Joy (41:54) The Random Day Experiment and Birth of Techstars (52:47) Writing Venture Deals, Startup Communities, and Give First (59:26) Coming Out of “Hibernation” to Write His Last Non-Fiction (1:13:39) Work-Life Balance vs. Work-Life Harmony Brad Feld is a venture capitalist, entrepreneur, and co-founder of Techstars, one of the world’s leading startup accelerators. He is also the co-founder of two venture capital firms, Foundry Group and Mobius Venture Capital. Brad is the author of nine books, including Venture Deals, Startup Communities, and Give First. Through his books, investments, and philosophy of “give first,” Brad has become a mentor to thousands of entrepreneurs navigating the brutal highs and lows of building a business. Connect with Brad:  Brad’s Website: feld.com Brad’s LinkedIn: linkedin.com/in/bfeld  Resources Mentioned Brad’s Book, Give First: The Power of Mentorship: https://www.amazon.com/dp/1646871324  Brad’s Book, Startup Communities: Building an Entrepreneurial Ecosystem in Your City: https://www.amazon.com/dp/1118441540  Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist by Brad Feld and Jason Mendelson: https://www.amazon.com/dp/1118443616  Reboot: Leadership and the Art of Growing Up by Jerry Colonna: https://www.amazon.com/dp/0062749536 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

Brendan Kane didn’t break into Hollywood through connections. He started out making coffee on film sets. Spotting the untapped power of MySpace and YouTube, he launched one of the first influencer campaigns, catching the attention of studio executives and A-list actors like Jason Statham. That bold move launched his journey from Hollywood to advising global icons such as Taylor Swift and Rihanna on social media strategy. In this episode, Brendan joins Ilana to reveal how he built one million followers in just 30 days, the formula for going viral, and the psychology behind grabbing and holding attention. Brendan Kane is a digital marketing expert who has helped top celebrities, Fortune 500 companies, and entrepreneurs dominate social media and generate millions in revenue. He specializes in data-driven strategies that drive massive social media engagement. In this episode, Ilana and Brendan will discuss: (00:00) Introduction  (02:07) His Childhood Love for Movies and Storytelling (03:17) Breaking into Hollywood Without Connections (08:16) The Bold Move That Led to Working With A-List Actors (10:37) Diving into Tech and Working with Taylor Swift, Rihanna, etc (17:51) Lessons from Managing $100M in YouTube Ad Spend (22:06) Uncovering the Secrets to Social Media Success (27:40) How Brendan Hit a Million Followers in 30 Days (34:51) Strategies for Marketing Bestselling Books (39:10) How to Adapt to Ever-Changing Platforms (44:01) Low-Cost Strategies to Stand Out on Social Media (45:35) Navigating the Challenges of Entrepreneurship Brendan Kane is a digital marketing expert who has helped top celebrities, Fortune 500 companies, and entrepreneurs dominate social media and generate millions in revenue. Known for building a following of over 1 million in just 30 days, Brendan specializes in data-driven strategies that drive massive social media engagement. He is the bestselling author of One Million Followers, Hook Point, and The Guide to Going Viral, where he reveals proven methods for scaling influence in today’s noisy digital world. Connect with Brendan: Brendan’s Website: brendanjkane.com  Brendan’s Instagram: instagram.com/brendankane  Resources Mentioned: Get Brendan’s Book, The Guide to Going Viral, for FREE: hookpoint.com/leap  Download Brendan’s Book, Hook Point for Free: hookpoint.com  Brendan’s Book, One Million Followers: How I Built a Massive Social Following in 30 Days: https://www.amazon.com/One-Million-Followers-Updated-Following/dp/195066547X  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  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

George Kurian’s journey from a modest upbringing in Kerala, India, to becoming CEO of NetApp is an extraordinary story. George worked cafeteria shifts and construction jobs to pay his way through Princeton before climbing the ranks at Oracle, McKinsey, and Cisco. In this episode, George opens up about the weight of being a “rookie CEO” responsible for 12,000 people, the discipline of saying no to 97% of ideas, and the humility it takes to lead through uncertainty. He and Ilana explore resilience, focus, and the future of AI, while revealing how diverse experiences and family values shaped his leadership philosophy. George Kurian is CEO of NetApp, a Fortune 500 data infrastructure and cloud services company. Under his leadership, NetApp has strengthened its cloud-first and data services strategy, growing into a $20 billion company. In this episode, Ilana and George will discuss: (00:00) Introduction (02:20) Family Role Models and Upbringing (06:00) Landing a Princeton Scholarship and Learning to Survive (09:20) Lessons from Oracle and McKinsey (13:50) Why George Left Cisco to Join NetApp (16:45) How Cafeteria Work Inspired NetApp’s Engineering Process (19:40) The ‘30-30-30’ Rule for Driving Organizational Change (22:40) George’s Journey to Becoming CEO Overnight (26:30) First-Time CEO Challenges and Leadership Struggles (30:40) Why a CEO Should Say “No” to 97% of Ideas (33:10) Betting on Cloud Partnerships Instead of Competing (37:15) The Power of Choosing Your Path and Tackling Hard Problems George Kurian is CEO of NetApp, a Fortune 500 data infrastructure and cloud services company. Before joining NetApp in 2011, he had built a diverse tech career that included leadership roles at Oracle, McKinsey, Cisco, and Akamai. Under his leadership, NetApp has strengthened its cloud-first and data services strategy, growing into a $20 billion company. Connect with George: George’s LinkedIn: linkedin.com/in/georgekuriannetapp 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

Klaus Kleinfeld’s journey from a difficult childhood in Germany to leading two Fortune 500 companies, Siemens and Alcoa, was anything but easy. He experienced  the true cost of leadership: the loneliness of making impossible decisions and the grit to push forward when every alternative seems bleak. In this episode, Klaus joins Ilana to share how resilience and freedom shaped his leadership philosophy. They dive into his shift from time management to energy management, exploring lessons from sports, breathing techniques, and mindset practices that helped him lead various multi-billion dollar businesses without burnout.  Dr. Klaus Kleinfeld is a German entrepreneur, investor, and former CEO of Siemens AG, Alcoa Inc., and ARconic. He is also the founder and CEO of the investment firm K2Elevation and was named director of Saudi Arabia's Neom initiative, later becoming an advisor to the Crown Prince. In this episode, Ilana and Klaus will discuss: (00:00) Introduction (02:01) Early Life and Family Tragedy (07:31) East vs. West Germany and Freedom (12:01) His Love for Problem-Solving (18:01) Creating a Strong Feedback Culture (23:31) Becoming the CEO of Siemens (30:01) The Loneliness of Leadership (35:31) Letting People Go with Respect (40:01) Facing Fear and Regret (45:31) Energy Over Time Management (50:01) Building a Passionate and High-Performance Team Dr. Klaus Kleinfeld is a German entrepreneur, investor, and former CEO of Siemens AG, Alcoa Inc., and ARconic. He is also the founder and CEO of the investment firm K2Elevation and was named director of Saudi Arabia's Neom initiative, later becoming an advisor to the Crown Prince. As the author of Leading to Thrive, Klaus offers a framework for blending personal well-being with strategic leadership.  Connect with Klaus: Klaus’s LinkedIn: linkedin.com/in/klauskleinfeld Resources Mentioned: Klaus’s Book, Leading to Thrive: Mastering Strategies for Sustainable Success in Business and Life: https://www.amazon.com/Leading-Thrive-Mastering-Strategies-Sustainable/dp/1544546718 The Power of Regret: How Looking Backward Moves Us Forward by Daniel Pink: https://www.amazon.com/Power-Regret-Looking-Backward-Forward/dp/0735210659 Open: An Autobiography by Andre Agassi: https://www.amazon.com/Open-Autobiography-Andre-Agassi/dp/0307388409 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

Nathan Blecharczyk, co-founder of Airbnb, built his first software business as a teenager, earning nearly a million dollars before shutting it down to attend Harvard. Years later, Nathan and his roommates turned an air mattress idea into Airbnb, facing investor rejection, financial hardship, and moments when quitting seemed inevitable. From creating satirical cereal boxes to joining Y Combinator after a near-failed interview, Nathan’s story is one of perseverance and resilience. He shares how Airbnb overcame early struggles, scaled globally, and survived COVID-19 to go public successfully. Nathan Blecharczyk is the co-founder and Chief Strategy Officer of Airbnb, where he helped grow the platform from a spare air mattress idea to a $75 billion global travel company. According to Forbes, he is one of the richest people in the world, with a net worth of $9 billion. In this episode, Ilana and Nathan will discuss: (00:00) Introduction (01:36) Building a Software Business as a Teen (05:28) Harvard, First Job, and the Decision to Move West (11:58) The Birth of AirBed & Breakfast (15:07) Landing Their  First Guests and Gaining Early Validation (18:03) Investor Rejection and the Obama O’s Cereal Stunt (30:45) Applying to Y Combinator and Getting In (36:29) Finding Evangelists and Meeting Hosts in New York (42:34) From $200 a Week to $4,200: Airbnb’s First Growth Curve (44:59) Global Expansion, Competitors, and Building Teams Abroad (52:22) The 2020 Crisis: COVID, Collapse, and Reinvention (59:21) The Future of Travel  Nathan Blecharczyk is the co-founder and Chief Strategy Officer of Airbnb, where he helped grow the platform from a spare air mattress idea to a $75 billion global travel company. A Harvard graduate and self-taught programmer, Nathan has been instrumental in Airbnb’s international expansion and strategy, navigating challenges from investor rejection to the COVID-19 crisis. According to Forbes, he is one of the richest people in the world, with a net worth of $9 billion. Connect with Nathan: Nathan’s LinkedIn: ⁠https://www.linkedin.com/in/blecharczyk⁠ Airbnb’s Website: ⁠https://www.airbnb.com⁠ Resources Mentioned: Y Combinator: ⁠https://www.ycombinator.com⁠Only the Paranoid Survive by Andy Grove: ⁠https://www.amazon.com/Only-Paranoid-Survive-Exploit-Challenge/dp/0385483821⁠ 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

After 12 years of working in corporate advertising, Case Kenny launched a podcast, New Mindset, Who Dis? as a personal experiment. In its first month, the show drew 57,000 downloads, yet Case kept it hidden, afraid it didn’t fit his professional image. Over time, he embraced his vulnerability, created bestselling guided journals, and built a brand helping millions live more optimistic and mindful lives. In this episode, Case joins Ilana to share how a side project turned into a multi-million-dollar portfolio career, why regret is his decision-making compass, and how choosing the right words can change the way you live. Case Kenny is an author, entrepreneur, and host of the globally recognized podcast, New Mindset, Who Dis?. Known for his work in mindfulness and personal growth, he has built a multi-million-dollar brand through writing, guided journals, and speaking engagements. In this episode, Ilana and Case will discuss: (00:00) Introduction (01:42) From Language Studies to Corporate Advertising (05:07) Starting the Podcast Without Clarity (07:43) Overcoming the Fear of Vulnerability (09:04) Stepping Fully into a New Identity (14:14) When Passion Becomes a Business (16:53) COVID, Journals, and a Turning Point in Sales (18:10) Why Journaling Works and How to Start (25:01) Building a Connected Portfolio Career (27:40) Business Challenges and Six-Figure Losses (33:09) Battling Expectations, Regret, and Trust as a Default (42:10) Defining Mindfulness and Advice to Case’s Younger Self Case Kenny is an author, entrepreneur, and host of the globally recognized podcast, New Mindset, Who Dis?, a podcast with tens of millions of downloads. Known for his work in mindfulness and personal growth, he has built a multi-million-dollar brand through writing, guided journals, and speaking engagements. His work has been featured on The Today Show, Good Morning America, Forbes, and NBC. Connect with Case: Case’s Website: casekenny.com Case’s LinkedIn: linkedin.com/in/casekenny/ Case’s Instagram: instagram.com/case.kenny Case’s YouTube: youtube.com/c/CaseKenny Resources Mentioned: Case’s Podcast, New Mindset, Who Dis?:  pod.link/1383599078 The Opposite of Settling by Case Kenny: https://www.amazon.com/Opposite-Settling-Everything-Without-Losing/dp/1401995918 The Soul’s Code by James Hillman: https://www.amazon.com/Souls-Code-James-Hillman/dp/0517271036 That’s Bold of You by Case Kenny: https://www.amazon.com/Thats-Bold-You-Thrive-Vibrant/dp/B0BRDFLJNZ 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

What do you do when the dream you've chased no longer fits? For Julia Hartz, it meant walking away from a promising career in Hollywood to dive into the unknown world of startups. As an intern on the set of Friends, she learned the value of kindness, clarity, and high standards. But the real test came in tech, where she bootstrapped through a downturn, faced 27 VC rejections, and ultimately co-founded Eventbrite, one of the world’s leading event ticketing platforms. In this episode, Julia joins Ilana to discuss her leap from TV to tech, how she led Eventbrite through a crisis, and how she continues to reinvent herself and her business.  Julia Hartz is the co-founder and CEO of Eventbrite, a global ticketing and event technology platform that empowers creators to bring people together through live experiences. In 2018, she took the company public on the New York Stock Exchange, making her one of the few female founders to lead a tech IPO. In this episode, Ilana and Julia will discuss: (00:00) Introduction (01:02) Julia’s Leap from Performance to Broadcasting (04:28) Her Internship on the Set of Friends (07:15) Discovering Her Path in TV Development at MTV (10:59) The Original Jackass Pilot and Startup-Like Creativity (14:55) Transitioning from MTV to FX and Facing Uncertainty (18:47) Leaving Hollywood to Build a Startup (26:43) The Product Strategy That Transformed Their Business (32:29) Getting 27 Rejections from VCs and Refusing to Quit (35:50) How the Financial Crisis Created Their Breakthrough (40:03) Reinventing Herself to Become CEO (46:05) How COVID Nearly Took Down Eventbrite (51:09) The One Rule She Always Comes Back To Julia Hartz is the co-founder and CEO of Eventbrite, a global ticketing and event technology platform that empowers creators to bring people together through live experiences. In 2018, she took the company public on the New York Stock Exchange, making her one of the few female founders to lead a tech IPO. Today, Eventbrite has powered millions of events and facilitated billions in ticket sales in 180 countries. Connect with Julia: Julia’s Website: eventbrite.com Julia’s LinkedIn: linkedin.com/in/juliahartz Julia’s Instagram: instagram.com/juliahartz 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

After getting laid off from his corporate job, Dan Shapiro launched his first startup, Photobucket Inc. (formerly Ontela), but faced nine months of rejection from investors and no funding. Despite these setbacks, his persistence led to a successful partnership, which later turned sour due to a managerial dispute. He took these lessons and went on to build multiple successful startups, including Glowforge, a $100M company revolutionizing 3D laser printing. In this episode, Dan joins Ilana to share the secrets to startup success, how to navigate entrepreneurial challenges, and what it takes to build a company that not only thrives but also transforms industries. Dan Shapiro is a serial entrepreneur, innovator, and CEO of Glowforge, a company that pioneered desktop laser technology, enabling creators to produce millions of custom products. He previously created Robot Turtles, the most successful board game in Kickstarter history, and founded Photobucket Inc. In this episode, Ilana and Dan will discuss: (00:00) Introduction  (01:56) Early Upbringing and Entrepreneurial Drive (04:47) Corporate Experience at Microsoft (08:14) The "Poop Umbrella" Leadership Principle (11:42) The Darkest Nine Months of Dan's Career (16:39) Securing Funding Against All Odds (20:35) The Brutal Truth About Entrepreneurship (24:32) The PhotoBucket Merger: What Went Wrong? (27:56) From 67 Rejections to a Google Acquisition (31:38) CEO Strategy: Delegate vs. Lead (36:24) The Bold Strategy Behind Robot Turtles' Success (45:16) Building Glowforge: From Idea to $100M Business (51:47) Leadership Challenges and Ethical Dilemmas Dan Shapiro is a serial entrepreneur, innovator, and CEO of Glowforge, a company that pioneered desktop laser technology, enabling creators to produce millions of custom products. He previously created Robot Turtles, the most successful board game in Kickstarter history, and founded Photobucket Inc. Dan also served as CEO of Google Comparison Inc. after Google acquired his startup, Sparkbuy. He is the author of Hot Seat and a prolific innovator with over 60 patents to his name.  Connect with Dan: Dan’s Website: danshapiro.com  Dan’s LinkedIn: linkedin.com/in/danshapiro  Resources Mentioned: Dan’s Book, Hot Seat: The Startup CEO Guidebook: https://www.amazon.com/Hot-Seat-Startup-CEO-Guidebook/dp/1449360734  Glowforge: https://glowforge.com  From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109: bit.ly/tim-oreilly-leap-academy  Bad Blood: Secrets and Lies in a Silicon Valley Startup by John Carreyrou: https://www.amazon.com/Bad-Blood-Secrets-Silicon-Startup/dp/152473165X  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

Dr. Josh Axe’s passion for health and wellness began when his mother’s breast cancer diagnosis led to chronic health issues after chemotherapy. Inspired by this, Josh pursued natural medicine, which helped her make a remarkable recovery when cancer returned. Years later, Josh faced a spinal infection that left him unable to walk. Doctors predicted permanent disability, but using the same healing mindset and natural methods that saved his mom, he defied the odds. In this episode, Josh joins Ilana to discuss the transformative power of belief, the keys to true health and success, and the secrets behind building a powerful personal brand. Dr. Josh Axe is a physician, entrepreneur, and leadership expert passionate about helping individuals use food and natural remedies to achieve optimal health and wellness. He is the founder of DrAxe.com and The Health Institute and the co-founder of Ancient Nutrition. In this episode, Ilana and Josh will discuss: (00:00) Introduction  (02:06) The Cancer Battle That Sparked His Health Mission (05:29) The Role of Belief in Healing, Growth, and Success (14:34) Building DrAxe.com into a Digital Health Powerhouse (20:55) The Scary Moment He Almost Lost Everything (24:05) Overcoming the Fear of Charging What You’re Worth (26:06) Josh’s Strategies for Building a Scalable Brand (31:12) Simple Habits for Total Health Transformation (34:37) From Bedridden to Healed: The Power of Belief (42:38) Why Character Beats Accomplishments Dr. Josh Axe is a physician, entrepreneur, and leadership expert passionate about helping individuals use food and natural remedies to achieve optimal health and wellness. He is the founder of DrAxe.com and The Health Institute and the co-founder of Ancient Nutrition. His businesses have ranked among the Inc. 500’s fastest-growing companies. Josh is the host of The Dr. Josh Axe Show and the bestselling author of Eat Dirt, The Keto Diet, and Think This, Not That. Connect with Josh: Josh’s Website: draxe.com  Josh’s LinkedIn: linkedin.com/in/joshaxe  Resources Mentioned: Josh’s Book, Think This, Not That: 12 Mindshifts to Breakthrough Limiting Beliefs and Become Who You Were Born to Be: https://www.amazon.com/Think-This-Not-That-Breakthrough/dp/1400337844  Josh’s Podcast, The Dr. Josh Axe Show: https://podcasts.apple.com/us/podcast/the-dr-josh-axe-show/id1700689487  The Health Institute: thehealthinstitute.com  Good to Great: Why Some Companies Make the Leap...And Others Don't by Jim Collins: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996  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

Sahil Bloom was living the "dream" life, climbing the corporate ladder, earning well, and hitting all the career milestones. Yet, he felt unfulfilled. During a conversation with an old friend, he mentioned how he only saw his parents once a year. His friend's blunt remark, "You're going to see your parents 15 more times before they die," hit him hard, forcing him to reevaluate his priorities and reassess his idea of success. In this episode, Sahil joins Ilana to share how to overcome the fear of career transitions, build a life that aligns with your values, and find fulfillment beyond a paycheck. Sahil Bloom is an entrepreneur, investor, and writer focused on redefining wealth beyond money. Through his newsletter, The Curiosity Chronicle, Sahil offers actionable ideas for building a high-performing, healthy, and wealthy life. In this episode, Ilana and Sahil will discuss: (00:00) Introduction  (01:46) The Cost of Chasing Traditional Success (04:33) Family Background and the Pressure to Succeed (08:41) What Baseball Taught Him About Life and Business (13:17) Unfulfillment Despite Corporate Success (18:50) Overcoming the Fear of Career Transition (23:35) Why Personal Growth and Change Can Feel Lonely (26:51) Turning Criticism into Fuel for Growth (29:34) Embracing Life’s Different Seasons (31:55) Writing The Five Types of Wealth (36:55) The Real Challenges in Entrepreneurship (41:24) How to Break Free When You’re Feeling Stuck Sahil Bloom is an entrepreneur, investor, and writer focused on redefining wealth beyond money. He is the author of the New York Times bestselling book The 5 Types of Wealth and the founder of SRB Ventures, an early-stage investment firm. Through his newsletter, The Curiosity Chronicle, Sahil offers actionable ideas for building a high-performing, healthy, and wealthy life. Connect with Sahil: Website: https://www.sahilbloom.com/#Hero  LinkedIn: linkedin.com/in/sahilbloom  Resources Mentioned: Sahil’s Book, The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life: https://www.amazon.com/Types-Wealth-Transformative-Guide-Design/dp/059372318X  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

When Christiana Figueres was a young mother, she longed to share her love of nature with her daughters, a love sparked by watching golden toads shimmer like coins under the moonlight in a Costa Rican forest. Hoping to show them this rare beauty, she returned to the same park, only to learn that the species had gone extinct due to rising temperatures. That moment ignited her mission to leave a better planet for her children. In this episode, Christiana joins Ilana to share her journey to becoming a United Nations Climate Change Executive Secretary and leading global climate efforts, including the historic 2015 Paris Agreement. Christiana Figueres is a Costa Rican diplomat and former Executive Secretary of the United Nations Framework Convention on Climate Change (UNFCCC). She is best known for her role in securing the Paris Agreement, a landmark international climate treaty.  In this episode, Ilana and Christiana will discuss: (00:00) Introduction  (01:53) Growing Up as Costa Rica’s President’s Daughter (06:24) The Life-Changing Experience in Rural Costa Rica (15:28) The Journey to Climate Change Advocacy (24:40) Key Lessons from the COP15 Climate Failure (30:45) Becoming UNFCCC Executive Secretary (35:50) Leading the Paris Agreement Negotiations (41:06) Building Trust in Global Climate Negotiations (47:39) Taking the Climate Mission Beyond the UN (51:03) Advice for Aspiring Change-Makers (54:05) Upcoming Projects and Digital Initiatives Christiana Figueres is a Costa Rican diplomat and former Executive Secretary of the United Nations Framework Convention on Climate Change (UNFCCC). She is best known for her role in securing the Paris Agreement, a landmark international climate treaty. With decades of experience in climate diplomacy, Christiana is a passionate global advocate for climate action and sustainable development. She is also the co-founder of Global Optimism, co-host of the Outrage + Optimism podcast, and co-author of The Future We Choose. Connect with Christiana: Christiana’s Website: christianafigueres.com  Christiana’s LinkedIn: linkedin.com/in/christianafigueres  Resources Mentioned: Christiana’s Book, The Future We Choose: Surviving the Climate Crisis: https://www.amazon.com/Future-We-Choose-Surviving-Climate/dp/0525658351  Christiana’s Podcast, Outrage + Optimism: outrageandoptimism.org Global Optimism: globaloptimism.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

Being scrappy wasn’t just a choice for Gary ‘Vee’ Vaynerchuk; it was his only way forward. After years of growing his family’s wine business, he was left with nothing of his own. With no money to rent an office or hire employees, Gary leveraged his grit, relationships, and opportunities to launch VaynerMedia. Overcoming the financial, mental, and emotional hurdles of entrepreneurship, he built his company into a multi-million-dollar media empire. In this episode, Gary joins Ilana to reveal the mindset and strategies you need to overcome obstacles and build your own multi-million-dollar business. Gary Vaynerchuk, famously known as GaryVee, is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early. In this episode, Ilana and Gary will discuss: (00:00) Introduction  (01:40) VaynerMedia's Scrappy Beginnings (06:56) Why Businesses Fail Financially (10:01) Navigating Tough Business Days (17:21) The Risk of Over-Transparency in Leadership (19:44) Dealing with Failure and Public Ridicule (22:10) GaryVee’s Dream of Owning the New York Jets (26:06) The Role of DNA and Accountability in Success (28:35) Finding Joy in Entrepreneurship (31:02) How to Build a Personal Brand as an Employee (32:30) Empowering Employees with Honest Feedback (34:27) Embracing Change and Executing Relentlessly Gary Vaynerchuk, famously known as GaryVee, is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. He is a prolific angel investor with early investments in companies like Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase, and Uber. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early. Connect with Gary: Gary’s Website: garyvaynerchuk.com  Gary’s LinkedIn: linkedin.com/in/garyvaynerchuk  Resources Mentioned: Gary’s Book, Day Trading Attention: How to Actually Build Brand and Sales in the New Social Media World: https://www.amazon.com/Day-Trading-Attention-Actually-Social/dp/0063317591  GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire: https://podcasts.apple.com/us/podcast/garyvee-from-earning-%242-an-hour-to-running-a/id1701718200?i=1000689595539  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

Matt Abrahams's passion for communication was shaped by his parents during his childhood. In the corporate world, he noticed that great ideas often went unheard because people were too anxious to speak up, particularly in high-pressure situations. Realizing that fear, not a lack of ideas, was the barrier to success, Matt made it his mission to help individuals overcome anxiety and communicate with confidence. In this episode, Matt joins Ilana to share his top techniques for managing public speaking anxiety and how you can transition from rambling to speaking with clarity, confidence, and impact. Matt Abrahams is a bestselling author, communication coach, and lecturer at the Stanford Graduate School of Business. He has helped individuals deliver impactful presentations, from IPO roadshows to Nobel Prize speeches, TED Talks, and World Economic Forum sessions. In this episode, Ilana and Matt will discuss: (00:00) Introduction  (01:50) His Path to Becoming a Communication Expert (05:50) Corporate Lessons and the Transition to Teaching (09:36) Mastering Communication as a Teacher (12:54) Understanding and Managing Anxiety (18:19) Matt’s Top Anxiety Management Techniques (23:15) The Keys to His Career Growth and Success (25:11) Turning Mistakes into Business Opportunities (28:49) Navigating Social Media and Feedback (33:29) How to Stop Rambling and Speak with Confidence (36:30) How to Understand and Connect with Your Audience Matt Abrahams is a bestselling author, communication coach, and lecturer at the Stanford Graduate School of Business. He is the author of Speaking Up Without Freaking Out and Think Faster, Talk Smarter, and host of the award-winning Think Fast, Talk Smart podcast. Matt has helped individuals deliver impactful presentations, from IPO roadshows to Nobel Prize speeches, TED Talks, and World Economic Forum sessions. Connect with Matt: Website: fastersmarter.io  LinkedIn: linkedin.com/in/maabrahams  Resources Mentioned: Matt’s Book, Think Faster, Talk Smarter: How to Speak Successfully When You're Put on the Spot: https://www.amazon.com/Think-Faster-Talk-Smarter-Successfully/dp/1668010305  Matt’s Book, Speaking Up without Freaking Out: 50 Techniques for Confident and Compelling Presenting: https://www.amazon.com/Speaking-without-Freaking-Out-Techniques/dp/1465290478  Matt’s Podcast, Think Fast Talk Smart: https://podcasts.apple.com/us/podcast/think-fast-talk-smart-communication-techniques/id1494989268  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