

Leap Academy with Ilana Golan
Ilana Golan
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.
Episodes
Mentioned books

Aug 19, 2025 • 52min
How Case Kenny Turned His Podcast into a Multi-Million Dollar Brand | E121
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.
Reserve your 24-HOUR PASS today at https://webinar.leapacademy.com/24hr-pass1

Aug 12, 2025 • 1h 5min
How Julia Hartz Built Eventbrite from a Startup to a Billion-Dollar IPO | E120
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.comJulia’s LinkedIn: linkedin.com/in/juliahartzJulia’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

Aug 5, 2025 • 1h 6min
68 Rejections, One Yes: How I Built a $100M Startup Against All Odds | Dan Shapiro | E119
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

Jul 29, 2025 • 50min
Dr. Josh Axe: From Healing My Mom of Cancer to Building a Multi-Million-Dollar Health Brand | E118
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

Jul 22, 2025 • 46min
Sahil Bloom: The 5 Types of Wealth, How to Find True Success and Fulfillment Beyond Money | E117
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

Jul 15, 2025 • 57min
Christiana Figueres: Building a Lasting Legacy in Global Climate Action at the UN and Beyond | E116
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

Jul 8, 2025 • 40min
GaryVee: The Mindset That Took Me from Zero to Multi-Million-Dollar Success | E115
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

Jul 1, 2025 • 43min
Matt Abrahams: How to Conquer Anxiety and Lead Powerful Conversations Under Pressure | E114
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

Jun 24, 2025 • 49min
From Singing in Parks to Selling Out Arenas: AJR’s Adam Met on Building Success from Scratch | E113
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 this episode, Adam joins Ilana to share insights from his new book, Amplify, which blends his experiences in music and climate advocacy to inspire community building across various fields.
Adam Met is a musician, climate advocate, educator, and member of the multiplatinum band AJR. He is the Executive Director of Planet Reimagined, a nonprofit leveraging media and strategic advocacy to mobilize climate action.
In this episode, Ilana and Adam will discuss:
(00:00) Introduction
(01:51) Early Musical Influences and Street Performances
(04:04) Coping with Rejection as a Child Performer
(05:52) Attracting an Audience While Embracing Nerves
(09:30) How One Tweet to Sia Changed AJR’s Career
(13:01) Why “I’m Ready” Became a Smash Hit
(16:58) Overcoming the Fear of Being a One-Hit Wonder
(21:29) The Innovative Strategies Behind AJR’s Success
(26:56) Two Key Tactics to Build an Engaged Fan Base
(28:48) The Birth of Adam’s Debut Book, Amplify
(31:28) How Adam Merges Music and Climate Advocacy
(34:21) Adapting Quickly: The Drive-In Concert Pivot
(39:21) Funding Climate Action Through Bipartisan Support
Adam Met is a musician, climate advocate, educator, and member of the multiplatinum band AJR. He is the Executive Director of Planet Reimagined, a nonprofit using media and strategic advocacy to mobilize climate action. Adam works closely with Congress and the White House to promote renewable energy and serves as a sustainability advocate for the United Nations Development Programme. In recognition of his efforts, Adam received the 2024 TIME Earth Award and was named a New York Times Changemaker.
Connect with Adam:
Adam’s Website: adammet.net
Adam’s LinkedIn: linkedin.com/in/adam-met-38274379
Resources Mentioned:
Adam’s Book, Amplify: How to Use the Power of Connection to Engage, Take Action, and Build a Better World: https://www.amazon.com/Amplify-Connection-Engage-Action-Better/dp/0593735900
Planet Reimagined: planetreimagined.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

Jun 17, 2025 • 58min
From Near Bankruptcy to a $745M Exit: The Raw Truth Behind Kass & Mike’s Entrepreneurship Journey | E112
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, Shoveling $h!t, sharing the struggles behind their wins, the fears they confronted, and how they built successful businesses while balancing parenthood, marriage, and health challenges.
Kass and Mike Lazerow are serial entrepreneurs, investors, and co-founders of Golf.com and Buddy Media. After selling Golf.com to Time Warner, they co-founded Buddy Media, a leading social media marketing platform that was acquired by Salesforce for $745 million.
In this episode, Ilana, Kass, and Mike will discuss:
(00:00) Introduction
(00:35) Meeting and Collaborating with GaryVee
(03:20) Childhood Challenges and Family Struggles
(09:43) Early Ventures and the Birth of Golf.com
(13:40) Kass and Mike’s Relationship Journey
(18:20) Facing Near Bankruptcy After Acquisition Offers
(23:02) Leading with Transparency in Crisis
(26:08) Fundraising Success and Tiger Woods's Influence
(28:44) Navigating Parenthood While Building a Business
(35:33) Prioritizing Health Amid Career Demands
(39:38) Breaking Gender Bias in Entrepreneurship
(43:57) Building a Thick Skin as an Entrepreneur
(47:31) Overcoming Fear and Taking Action
Kass and Mike Lazerow are serial entrepreneurs, investors, and co-founders of Golf.com and Buddy Media. After selling Golf.com to Time Warner, they co-founded Buddy Media, a leading social media marketing platform that was acquired by Salesforce for $745 million. Together, Mike and Kass have supported nearly 100 early-stage startup founders and have received multiple awards recognizing their leadership and impact in entrepreneurship and philanthropy.
Connect with Kass and Mike:
Kass and Mike’s Website: www.kassandmike.com
Kass and Mike’s Email: info@kassandmike.com
Resources Mentioned:
Kass and Mike Book, Shoveling $H!t: A Love Story about the Entrepreneur's Messy Path to Success: https://www.amazon.in/Shoveling-Story-about-Entrepreneurs-Success/dp/B0DY21NS7W
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