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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:
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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 -
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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 -
Brian Tracy went from struggling with a series of menial jobs to achieving remarkable sales success. A relentless self-learner, he transformed his life by mastering the science of sales. Then, he dedicated himself to studying, researching, writing, and speaking in the fields of economics, history, business, philosophy, and psychology. Today, he is a legendary self-development expert and world-renowned bestselling author. In this episode, Brian shares his top principles and strategies for unlocking your full potential in both life and business.
Brian Tracy is the Chairman and CEO of Brian Tracy International. He is a prolific businessman, renowned speaker, and bestselling author of over 80 books, including his latest, The 32 Unbreakable Laws of Money and Success.
In this episode, Ilana and Brian will discuss:
- Brian’s journey to sales mastery
- The skill that transformed Brian’s career
- The power of sticking to goals
- How to crush “excusitis” and start achieving your dreams
- Small daily actions that double your income over time
- The 3x3x3 hiring method for building your dream team
- Brian’s guaranteed method to 10x your productivity
- How he developed a $3M shopping center from nothing
- The secret to fast-tracking your career
- Why there’s no shortage of money
- And other topics…
Brian Tracy is a speaker, bestselling author, and the Chairman and CEO of Brian Tracy International. He trains and develops individuals and organizations to achieve their personal and business goals faster and easier. Before founding his company, Brian was the Chief Operating Officer of a $265 million development company. He has had successful careers in sales and marketing, investments, real estate development and syndication, importation, distribution, and management consulting. Brian has spoken and delivered seminars to millions of people across the world. He has authored over 80 books, including bestsellers, Eat That Frog and The Success Secrets of Self-Made Millionaires. His latest book, The 32 Unbreakable Laws of Money and Success was released in June 2024.
Connect with Brian:
Brian’s Website: https://www.briantracy.com/
Brian’s LinkedIn: https://www.linkedin.com/company/brian-tracy-international/
Resources Mentioned:
Brian’s Books:
The 32 Unbreakable Laws of Money and Success: Transform Your Life and Unlock Your Unlimited Potential: https://www.amazon.com/Unbreakable-Laws-Money-Success-Transform/dp/1523007001
Eat That Frog!: 21 Great Ways to Stop Procrastinating and Get More Done in Less Time: https://www.amazon.com/Eat-That-Frog-Great-Procrastinating/dp/162656941X
The 21 Success Secrets of Self-Made Millionaires: How to Achieve Financial Independence Faster and Easier than You Ever Thought Possible: https://www.amazon.com/Success-Secrets-Self-Made-Millionaires-Independence/dp/0369307534
Think and Grow Rich by Napoleon Hill: https://www.amazon.com/Think-Grow-Rich-Landmark-Bestseller/dp/1585424331 -
Kelly Roach built a seven-figure side hustle before leaving her corporate role. How did she do it despite an intense workload and failed product launches? Strategic planning, smart time management, and an unyielding drive fueled by a childhood embarrassment on the free lunch line. In this episode, Kelly shares her inspiring journey, emphasizing the importance of patience, persistence, and the willingness to take imperfect action.
Kelly Roach is a business coach, CEO, podcast host, and bestselling author. Before launching her multimillion-dollar business, she worked at a Fortune 500 company, rising to become its youngest VP.
In this episode, Ilana and Kelly will discuss:
- The defining moment that fueled her ambition
- Juggling multiple jobs in college
- Her transition from NFL cheerleader to corporate leader
- Why entrepreneurs must embrace imperfect action
- The importance of mental toughness
- Her transition from corporate to entrepreneurship
- Staying motivated through failures
- The importance of investing in coaching
- Effective time management for side hustlers
- Financial strategies for entrepreneurs
- And other topics…
Kelly Roach is a business coach, CEO, podcast host, and bestselling author of Conviction Marketing and The Live Launch Method. She rose from an entry-level sales position at a Fortune 500 company to become its youngest VP. While working full-time, she started her multimillion-dollar company, Kelly Roach Coaching. Kelly is also the creator of the Live Launch Method, a simple launch strategy that leverages timeless business principles to help entrepreneurs consistently generate six-figure results. She is regularly sought after as a coaching expert by several news outlets.
Connect with Kelly:
Kelly’s Website: https://kellyroachcoaching.com/
Kelly’s LinkedIn: https://www.linkedin.com/company/kellyroachinternational/
Resources Mentioned:
Kelly’s Podcast, The Kelly Roach Show: https://podcasts.apple.com/us/podcast/the-kelly-roach-show/id -
Even when met with skepticism, Geoff Smart pushed forward with his vision to transform hiring through powerful data-driven methods. He created the WHO Method through his leadership consulting firm, emphasizing drive and cultural fit over skills. This approach not only brought success to his clients but also propelled his firm to global success. In this episode, Geoff reveals the key strategies behind the WHO Method, including how to prioritize drive over skills and ensure cultural alignment in hiring.
Dr. Geoff Smart is the Chairman and Founder of ghSMART, a top leadership consulting firm serving Fortune 500 CEOs, boards, and entrepreneurs. He is a New York Times bestselling author and renowned expert on hiring and leadership, dedicated to helping leaders achieve extraordinary results through smart team building.
In this episode, Ilana and Geoff will discuss:
- Cracking the code to hiring superstar talent
- Why drive outshines talent in every scenario
- How to build a culture that accelerates growth
- Interview techniques that reveal true potential
- Success predictors most leaders overlook
- Leadership secrets that cultivate a winning culture
- How consistency can skyrocket your career
- Emotional intelligence as a leadership superpower
- Setting boundaries that fuel success
- The WHO method for flawless hiring
- And other topics…
Dr. Geoff Smart is the Chairman and Founder of ghSMART, a leadership consulting firm serving Fortune 500 CEOs, boards, billionaire entrepreneurs, and heads of state worldwide. A sought-after expert in hiring and leadership, he co-authored the New York Times bestselling books Who, Leadocracy, and Power Score. Under his leadership, ghSMART has earned recognition as a top consulting firm, known for its client impact and employee satisfaction.
Connect with Geoff:
Geoff’s LinkedIn: https://www.linkedin.com/in/drgeoffsmart/
Resources Mentioned:
SMARTtools for Leaders: https://geoffsmart.com/smarttools/
ghSMART: www.ghsmart.com
Geoff’s Books:
Who: https://www.amazon.com/Who-Geoff-Smart/dp/0345504194
Power Score: Your Formula for Leadership Success: https://www.amazon.com/Power-Score-Formula-Leadership-Success/dp/0345547357
Leadocracy: Hiring More Great Leaders (Like You) into Government: https://www.amazon.com/Leadocracy-Hiring-Great-Leaders-Government/dp/1608322882 -
Eynat Guez leaped from a comfortable corporate job to co-founding Papaya Global. Despite numerous investor rejections, she stayed true to her vision, proving the market need for her innovative solutions. Balancing motherhood and entrepreneurship, she turned her startup into a global payroll and HR solutions powerhouse valued at $3.7 billion. In this episode, Eynat reveals the highs and lows of her entrepreneurial journey, underscoring the importance of resilience and adaptability in achieving success.
Eynat Guez is the co-founder and CEO of Papaya Global, a leading global payroll platform. She has been recognized among Forbes Israel's Power Women and Fortune’s most powerful women in startups.
In this episode, Ilana and Eynat will discuss:
- The hardest parts of being an entrepreneur
- The best way to deal with negative feedback
- The loneliness of the CEO role
- Eynat’s struggle to raise capital while pregnant
- Strategies for dealing with rejection
- The importance of client-centricity
- Balancing motherhood with a demanding career
- The differences between building and scaling a company
- How to stay motivated through setbacks
- The significance of humility in leadership
- The importance of a supportive network
- And other topics…
Eynat Guez is the co-founder and CEO of Papaya Global, a global payroll and workforce management platform valued at $3.7 billion. Raised in Israel, she started her career in HR and technology, holding key roles in Africa and China before founding Papaya Global in 2016. Eynat champions diversity, maintaining a 50% female workforce and advocating for Israeli-Palestinian economic cooperation. She has been recognized among Forbes Israel's Power Women and Fortune’s most powerful women in startups. Eynat holds a BA in Political Science and Business Administration from the Open University of Israel.
Connect with Eynat:
Eynat’s LinkedIn: https://www.linkedin.com/in/eynatguez/
Resources Mentioned:
Papaya Global: https://www.papayaglobal.com/ -
As Charlie Engle's teenage sons dropped him off at the gates of federal prison, he faced his lowest point. Sentenced to 21 months for mail fraud, he had lost his career, reputation, and freedom. Despite his history of overcoming addiction and running across the Sahara, this challenge was the hardest. Initially consumed by anger and fear, Charlie turned to running daily. He inspired fellow inmates, earning the nickname "Running Man" and forming a running group. In this episode, Charlie reveals the mindset shifts that turned his lowest point into triumph, rebuilding his life post-incarceration into one of influence.
Charlie Engle is an ultramarathon runner, author, and motivational speaker. He is also known as the “Running Man” who ran 4,600 miles across the Sahara. He is also known for co-founding H2O Africa with Matt Damon, which later became Water.org.
In this episode, Ilana and Charlie will discuss:
- The pivotal moment that sparked his journey to sobriety
- Embracing extreme ownership for personal growth
- The incredible story behind the Sahara expedition
- Staying motivated against all odds
- Managing team dynamics in extreme situations
- Life lessons from his time in federal prison
- Leveraging vulnerability and resilience for success
- Obsession as the key to success
- Why passion trumps knowledge
- The danger of staying in your bubble
- Achieving big goals through consistent small steps
- How to build unshakeable confidence
- And other topics…
Charlie Engle is an accomplished ultramarathon runner, author of Running Man, and motivational speaker known for his extraordinary endurance feats and inspiring life story. His remarkable journey of running across the Sahara Desert and overcoming addiction has been documented in the film, Running the Sahara, narrated and produced by Matt Damon. Besides his athletic achievements, Charlie co-founded H2O Africa, which later became Water.org, raising millions for clean water initiatives. He continues to inspire audiences worldwide through his speaking engagements, focusing on resilience, overcoming adversity, and the power of perseverance.
Connect with Charlie:
Charlie’s Website: https://www.charlieengle.com/
Charlie’s LinkedIn: https://www.linkedin.com/in/charlie-engle-3644676/
Resources Mentioned:
Water.org: https://water.org/
Running the Sahara narrated by Matt Damon: https://www.imdb.com/title/tt0481222/
Running Man: A Memoir: https://www.amazon.com/Running-Man-Memoir-Charlie-Engle/dp/1476785783 -
Feeling creatively stifled in his stable but unfulfilling job, Adam Cheyer pursued entrepreneurship, even with his limited business knowledge. He co-founded Siri to realize his dream of a voice-activated assistant and the project was so promising that Steve Jobs called out of the blue. Despite initially turning down his offer, Jobs persisted. Today, Siri is integrated into billions of Apple devices. In this episode, Adam shares the key moments and mindset shifts that turned his vision into reality.
Adam Cheyer is an inventor, entrepreneur, and VP of AI Experience at Airbnb. He has founded multiple successful startups, including Siri and Change.org.
In this episode, Ilana and Adam will discuss:
- The emotional drive behind leaving a stable job
- Challenges of starting a business in his forties
- The exciting story behind creating Siri
- The unexpected call from Steve Jobs
- Adam’s process for timing new innovations
- How visualizing success boosts motivation
- The power of being first in new markets
- Maintaining perseverance as an entrepreneur
- The evolution of AI
- And other topics…
Adam Cheyer is an inventor, entrepreneur, and engineering executive, recognized for his pioneering work in AI and human-computer interfaces. Throughout his career, Adam has co-founded or been a founding member of multiple successful startups, including Siri, Change.org, GamePlanner.AI, Sentient, and Viv Labs. Currently, he serves as the VP of AI Experience at Airbnb, leveraging generative AI to transform the platform into an intuitive travel concierge. In addition to his technology work, he is also an award-winning magician and a member of the prestigious Magic Castle in Los Angeles.
Connect with Adam:
Adam’s Website: http://adam.cheyer.com/site/home
Adam’s LinkedIn: https://www.linkedin.com/in/adamcheyer/
Resources Mentioned:
Change.org: https://www.change.org/ -
Immersed in her privileged life in apartheid South Africa, Ronni Kahn never imagined she would become a leader in the fight against food waste and hunger. She went from one bold leap to the next—leaving a kibbutz in Israel to start from scratch in a new country, then building a successful business only to leave it to start a nonprofit. In this episode, Ronni shares the pivotal moments and challenges that led her to find her true calling, the importance of taking risks, and the powerful impact of small acts of kindness.
Ronni Kahn is a South African-born Australian social entrepreneur, passionate activist, and the founder of OzHarvest, Australia’s leading food rescue charity. In 2020, she co-authored her memoir, A Repurposed Life, which was nominated for an ABIA award for Biography Book of the Year.
In this episode, Ilana and Ronni will discuss:
- Ronni's upbringing in apartheid South Africa
- The values of resilience from her parents
- Adapting from a kibbutz in Israel to life in Australia
- The value of experimentation for entrepreneurs
- Going from zero to a successful event planning business
- The food waste revelation that led to OzHarvest
- Overcoming doubts and finding purpose
- The jump from business to nonprofit
- Why you must seize opportunities
- The value of small acts of kindness
- Taking risks and following your passion
- And other topics…
Ronni Kahn is the founder and Visionary In Residence at OzHarvest, Australia’s leading food rescue charity. After witnessing significant food waste in her successful events management business, she founded the organization in 2004 to combat hunger and reduce waste. A passionate advocate and activist, she has earned numerous awards, including being named Australia’s Local Hero in 2010. She has also been appointed Officer of the Order of Australia (AO) and named in Boss Magazine's Top 21 True Leaders. In 2020, she co-authored her memoir, A Repurposed Life, which was nominated for an ABIA award for Biography Book of the Year.
Connect with Ronni:
Ronni’s Website: https://ronnikahn.com/
Ronni’s LinkedIn: https://www.linkedin.com/in/ronni-kahn/
Ronni’s Email: [email protected]
Resources Mentioned:
Ronni’s Book, A Repurposed Life: https://www.amazon.com/Repurposed-Life-Ronni-Kahn/dp/1911632949
Write to Ilana: [email protected] -
From nearly failing out of college to becoming the number one executive coach, Marshall Goldsmith embodies the power of relentless self-improvement. Shaped by harrowing experiences, influential mentors, and Buddhism, he has gained unique perspectives on gratitude, resilience, and purpose, inspiring leaders worldwide to achieve their full potential. In this episode, Marshall Goldsmith shares the importance of finding fulfillment, enjoying the process of life, and avoiding achievement addiction.
Marshall Goldsmith is a renowned authority on leadership and coaching for behavioral change. He is also the bestselling author of multiple books, including The Earned Life. He has worked with leaders of major organizations such as Forbes, Pfizer, Walmart, and the World Bank.
In this episode, Ilana and Marshall will discuss:
- Why successful people need coaches
- The value of finding happiness in the present
- The three ingredients for happiness
- Why you must avoid achievement addiction
- The problem with delayed gratification
- Why you must have a higher purpose
- The importance of translating goals into daily actions
- Why you can’t achieve your way to happiness
- His AI bot and excitement about technology
- The challenges of living up to one's values
- How to live without regret
- And other topics…
Marshall Goldsmith is a foremost expert in leadership and behavioral change coaching. Since 2011, he has been consistently recognized as one of the top ten business thinkers globally and has earned the distinction of top-rated executive coach at the Thinkers50 awards in London. Marshall has penned several #1 bestsellers on the Wall Street Journal and New York Times lists, including Triggers and The Earned Life. He has worked with leaders of major organizations such as Forbes, Pfizer, Walmart, and the World Bank.
Connect with Marshall:
Marshall’s Website: https://marshallgoldsmith.com/
Marshall’s LinkedIn: https://www.linkedin.com/in/marshallgoldsmith/
Resources Mentioned:
Marshall’s Book, The Earned Life: Lose Regret, Choose Fulfillment: https://www.amazon.com/Earned-Life-Regret-Choose-Fulfillment/dp/0593237277
Marshall’s AI Tool: https://marshallgoldsmith.ai/ -
Dave Liniger went from pinching pennies while saving for his first property to owning 21 single-family homes at age 21. Despite fierce opposition and financial turmoil, he implemented an innovative commission system that empowered agents to maximize their earnings. His unique model not only transformed his company into a global real estate powerhouse but also revolutionized the entire industry. In this episode, Dave shares his incredible journey of perseverance, highlighting the principles and mindset shifts that drove him to success.
Dave Liniger is the co-founder of RE/MAX, a real estate empire that spans over 115 countries with more than 142,000 sales agents. He is also a decorated Air Force veteran and serial entrepreneur.
In this episode, Ilana and Dave will discuss:
- Dave's journey from military service to real estate
- Disrupting real estate with RE/MAX
- Financial struggles and industry resistance in the early days
- Building confidence through small wins
- The importance of humility in leadership
- How the military prepared Dave for business challenges
- Turning personal adversity into a motivational force
- Dave’s unyielding determination to recover from paralysis
- The power of selling hope as a leader
- And other topics…
Dave Liniger is a legendary figure in the real estate industry, renowned for co-founding RE/MAX with his wife, Gail. He revolutionized the real estate business by introducing a model that significantly increased agent commissions. RE/MAX has now expanded into a real estate empire that spans over 115 countries with more than 142,000 sales agents. Dave is also a decorated Air Force veteran, serial entrepreneur, philanthropist, adventurer, and a passionate advocate for perseverance and leadership. He is the bestselling author of The Perfect 10 and the host of the Ambition and Grit podcast. After retiring as CEO in 2018, Dave continues to serve as Chairman of the Board at RE/MAX Holdings.
Connect with Dave:
Dave’s Website: https://daveliniger.com/
Dave’s LinkedIn: https://www.linkedin.com/in/dave-liniger/
Resources Mentioned:
Dave’s Podcast, Ambition and Grit: https://podcasts.apple.com/us/podcast/ambition-and-grit/id1674022837
Dave’s Book, The Perfect 10: 10 Leadership Principles to Achieve True Independence, Extreme Wealth, and Huge Success: https://www.amazon.com/Perfect-10-Leadership-Principles-Independence/dp/1637631839
How I Turned $1,000 into a Million in Real Estate in My Spare Time by William Nickerson: https://www.amazon.com/Turned-into-Million-Estate-Spare/dp/1607964244 -
John Lee Dumas went from leading his seniors in the military at 23 to failing at different careers for six years. Although the fear of failure almost held him back, he pushed through and started his podcast at 32. Today, he generates over a million dollars in annual revenue. In this episode, John shares lessons from his journey, actionable insights on overcoming fear, and strategies for entrepreneurial success.
John Lee Dumas is the founder and host of the award-winning podcast Entrepreneurs on Fire, with over 160 million total listens. He is also the author of The Common Path to Uncommon Success.
In this episode, Ilana and John will discuss:
- His battle with PTSD
- How he reinvented himself after military service
- His six years of entrepreneurial struggles
- Why failure is so scary
- Why you must launch before you’re ready
- Moving from "pre-launch mode" to decisive action
- How high barriers eliminate the competition
- Why he publishes monthly income reports
- Providing value by solving real problems effectively
- Patience and relaxation for long-term success
- And other topics…
John Lee Dumas is the founder and host of the award-winning podcast Entrepreneurs On Fire, which has over 4,000 episodes and more than 160 million total listens. He began his entrepreneurial journey in 2012 after serving in the US Army and working in corporate finance and real estate. His podcast, known for its daily interviews with inspiring entrepreneurs, generates over $1 million in annual revenue. John is also the author of The Common Path to Uncommon Success, a guide to achieving financial freedom and fulfillment.
Connect with John:
John’s Website: https://www.eofire.com/
John’s LinkedIn: https://www.linkedin.com/in/eofire/
Resources Mentioned:
John’s Book, The Common Path to Uncommon Success: A Roadmap to Financial Freedom and Fulfillment: https://www.amazon.com/Common-Path-Uncommon-Success-Fulfillment/dp/1400221099
Think and Grow Rich by Napoleon Hill: https://www.amazon.com/Think-Grow-Rich-Landmark-Bestseller/dp/1585424331 - もっと表示する
