The Leap Academy Podcast with Ilana Golan is all about honest and inspiring conversations about what it really takes to leap to bigger things, amazing careers, and craft the life you want.
Stories and tips you won't find anywhere else.
Ilana speaks with some of the world's most influential people, experts, and thinkers who created incredible careers, massive impact, built a reputation, and an extraordinary life.
Together we discover the untold truths, the emotions, and important lessons that enabled them to reinvent themselves & leap.
We take our audience on a journey that will not only inspire but also teach concrete lessons on how to leap careers: fast-track to leadership, jump to entrepreneurship, build a personal brand, portfolio career, and much more.
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In this episode, Guy Kawasaki interviews Ilana Golan about her remarkable career reinventions, from the Israeli Air Force to tech executive and investor. Ilana defines reinvention, outlines a systematic process, and offers tactical advice for women facing systemic barriers. The conversation also delves into the importance of personal branding, the role of timing, and case studies of public figures, providing practical insights for anyone looking to leap to their full potential.
This episode features Vick Tipnes, founder of Blackstone Medical Services, detailing his remarkable rise from financial ruin to a multi-million dollar healthcare empire. He discusses the sacrifices, the power of an unyielding mindset, and the tenacious drive required to overcome significant personal and business challenges, ultimately transforming a small $500 office into an industry leader in sleep testing. Vick also shares insights on continuous personal growth and the importance of never quitting, despite years of losing money.
John Demsey didn’t become a powerhouse in the beauty industry by a mere stroke of luck; he built that influence on retail floors, taking on scrappy roles while learning the business in ways no MBA could ever teach. This helped him scale MAC Cosmetics into a global cultural movement, shape some of the most iconic beauty brands of our time, and ultimately rise to Group President of Estée Lauder Companies. In this episode, John joins Ilana to reveal how to build a career from the ground up, reinven...
When 19-year-old Anna-Sophie Hartvigsen walked into a bank hoping to secure a loan to buy a property, she was denied on the spot. That “no” pushed her into investing and ultimately led her to co-found Female Invest, a global platform empowering women to take control of their financial futures. In this episode, Anna joins Ilana for a raw, honest conversation about the reality of fundraising as a female founder, from enduring 107 rejections to breaking global crowdfunding records and facing the ba...
In this Leap Replay, personal development legend Brian Tracy reveals his journey from being broke to becoming a global authority on success. He outlines concrete strategies like the 80/20 rule, the power of written goals using a simple notebook, and a 7-step compounding principle to significantly increase income and productivity. The episode delves into financial wisdom from business giants, leadership principles, effective hiring, and overcoming excuses, offering actionable insights for achieving immense personal and financial success.
Sharon Price John, CEO of Build-A-Bear Workshop, recounts her extraordinary career, from overcoming a failed startup to masterfully turning around major brands like Nerf and Build-A-Bear. She discusses her "stop doing stupid stuff" strategy, leading through crises like COVID-19 with clarity and courage, and the importance of empowering personal stories. Her insights offer a compelling blueprint for career transformation and effective leadership in challenging environments.
He could have built a billion-dollar company, but instead, Jimmy Wales built a movement. When the dotcom crash hit and funding vanished, he didn’t sell out or add ads. He doubled down on values, creating Wikipedia, a global temple for the mind that made knowledge free to billions. In this episode, Jimmy joins Ilana to share the story behind that decision, the failures that shaped him, and the community that built the impossible. He breaks down why the best ideas come from doing something interes...
Ben Weiss set out to create the future of footwear. With nothing but conviction and a radical idea to merge AI with design, he reached out to Reebok co-founder Joe Foster, the man who turned a small factory dream into a global empire. What began as a cold message became a collaboration between two builders chasing the next revolution in shoes. In this episode, Ben and Joe join Ilana to unpack what it takes to see opportunity before the world does and how to keep building, no matter the odds or t...
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 e...
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 ...
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 de...
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...
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...
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 ...
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 fi...
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 an...
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 fol...
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...
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 sport...
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 Ai...
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-dol...
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...
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 shar...
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...
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...
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...
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 m...
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 speak...
As a teenager performing on New York’s streets and parks, Adam Met never imagined selling out arenas nationwide. Alongside his brothers Jack and Ryan, he formed the band AJR, playing for hours each summer while learning to capture the attention of indifferent passersby. A single tweet to Sia changed everything, launching their breakthrough. Balancing music with demanding academic work and nonprofit leadership, Adam mastered the art of building an engaged fan base that is driven to action. In thi...
Kass and Mike Lazerow’s entrepreneurial journey began with a leap of faith and a lot of grit. They started Golf.com with funding from friends and family, only to be acquired by a company that later went bankrupt. Forced to raise capital and revive their business against all odds, they quickly learned that entrepreneurship means facing setbacks every day and building the resilience to keep going when it feels impossible. In this episode, Kass and Mike join Ilana to dive into their new book, Shove...
