The Jen Gottlieb Show

Ever felt like you're the only one drowning in the chaos of entrepreneurship while everyone else is thriving? You're not alone. I sat down with power couple Kass and Mike Lazerow to talk about what it really takes to build businesses, survive failure, and stay married through all the messy middle.  They share how they lost everything, clawed their way back, and built multiple companies—together—without pretending everything was fine when it wasn’t. We talk about what it means to “shovel the sh*t,” how to lead through crisis without faking it, and why transparency and uncomfortable conversations are your greatest leadership tools.  So, if you’ve ever felt like you're hustling in the dark and wondering if you’re doing it wrong, this episode is for you. Remember to grab your copy of Kass and Mike’s book, Shoveling $h!t, to join their founder community. You don’t have to shovel alone! "People want to be led, and what that means is getting the right people in the right positions." ~Mike Lazerow In this Episode: - Meet Kass and Mike Lazerow - The story behind ‘Shoveling $h!t’ - Real stories of entrepreneurial challenges - Lessons learned in transparency and leadership - How to hold tough conversations with employees - Balancing life and entrepreneurship as a couple - A proven system of prioritizing tasks and making decisions - Navigating business partnerships  - The value of personal branding - Entrepreneurship lessons from 'Shoveling $hit' - Final thoughts on entrepreneurship  About Kass & Mike Lazerow: Kass and Mike Lazerow are serial entrepreneurs, investors, and authors renowned for co-founding Golf.com and Buddy Media, the latter of which was sold to Salesforce for $745 million. As partners in both business and life, they've built and scaled multiple ventures while raising a family. Through their firm, Velvet Sea Ventures, they have invested in over 100 startups, including Scopely and Liquid Death. Their book, Shoveling $h!t: A Love Story offers an unfiltered glimpse into the entrepreneurial journey. Website: https://www.kassandmike.com/  Instagram: https://www.instagram.com/kassandmike   Facebook: https://www.facebook.com/kassandmike YouTube: https://www.youtube.com/@KassandMike  Where to find me: IG: https://www.instagram.com/jen_gottlieb/    TikTok: https://www.tiktok.com/@jen_gottlieb     Facebook: https://www.facebook.com/Jenleahgottlieb    Website: https://jengottlieb.com/    My business: https://www.superconnectormedia.com/     YouTube: https://www.youtube.com/@jen_gottlieb

Ever hit record and suddenly feel like a cringey version of yourself takes over? I’ve been there. So, today, I’m sharing the mindset shifts and quick hacks I use to stop overthinking, sound natural, and actually enjoy being on camera. You’ll learn how to switch from “taking” to “giving” energy, why speaking to one person changes everything, and how knowing a secret brings your real self forward. These tips aren’t just fluff—they’re what I rely on every time I film.  So, if you struggle to show up confidently on video, this is for you. Tune in now and learn how to be confident on camera effortlessly. "You're not talking to this little black circle. You are talking to an individual on the other side that hopefully you can help with your words." ~ Jen Gottlieb In this Episode: - Introduction: Overcoming camera shyness - Mindset shift from seeking approval to giving value - Help One Person Every Day (HOPE) - Know your objective and believe in it - The power of knowing a secret Where to find me: IG: https://www.instagram.com/jen_gottlieb/    TikTok: https://www.tiktok.com/@jen_gottlieb     Facebook: https://www.facebook.com/Jenleahgottlieb    Website: https://jengottlieb.com/    My business: https://www.superconnectormedia.com/     YouTube: https://www.youtube.com/@jen_gottlieb

Have you ever thought about how practicing under pressure could actually make the real thing feel effortless? In this solo episode, I share a story that still gives me chills—a moment when everything went sideways right before I stepped on stage. The experience made me realize the magic of training at a “higher altitude.” You’ll learn what it means to build your stage off the stage and why challenging yourself in small ways every day leads to unstoppable confidence. This episode is a love letter to every rep you’re putting in behind the scenes. Tune in now, and remember to DM me what you want me to talk about on my next solo. "It's the little extra mile things that we do every day that build up our capacity to withstand greater discomforts later when they arise." ~ Jen Gottlieb In this Episode: - The analogy of training at a higher altitude - My journey to mastering public speaking - Practical tips for effective practice - The unexpected keynote experience Where to find me: IG: https://www.instagram.com/jen_gottlieb/    TikTok: https://www.tiktok.com/@jen_gottlieb     Facebook: https://www.facebook.com/Jenleahgottlieb    Website: https://jengottlieb.com/    My business: https://www.superconnectormedia.com/    YouTube: https://www.youtube.com/@jen_gottlieb

Are you feeling stuck in your current career or business, unsure if it’s the right fit for your future? I had the chance to speak with John Coco, a former music educator turned catastrophic injury attorney. John’s story is a powerful example of how the right mindset, faith, and the willingness to pivot can completely transform your career and life.  John shares his journey of shifting from a thriving music business to pursuing law, despite the doubts and opposition from others. He explains how his entrepreneurial spirit and unwavering belief in his ability to succeed led him to law school while balancing family life and financial strain.   If you’re feeling uncertain about making a big leap or struggling to take action, John's story will inspire you to keep moving forward. Tune in to learn how embracing change, trusting yourself, and taking calculated risks can lead to incredible success.  "You don't need to extract from everyone with every situation. Sometimes, just bless people. Be generous to them, and things will work out for you." ~ John Coco In this Episode: - John's career pivot from music to law - The challenges and rewards of law school  - How to overcome doubts and naysayers - Choosing injury law and entrepreneurial insights - Mindset hacks for dealing with uncertainty in entrepreneurship - Legal tips for entrepreneurs - Leveraging AI tools in the legal industry - The power of generosity and faith - How to connect with John Coco About John Coco: John Coco is a New York-based catastrophic injury attorney and law firm owner. His firm recovers millions each year on behalf of individuals who have been wrongfully injured. An entrepreneur since his teenage years, John’s first career was in music. He earned both a degree in music education and a Master’s in Jazz Guitar Performance before pivoting to law.  At age 30, while running a business, raising one child, and with his wife eight months pregnant, John made the bold decision to enter law school. Today, he’s a father of five and a relentless advocate for those navigating a legal system stacked against them. John is passionate not only about fighting for clients with life-altering injuries but also about empowering the public to better advocate for themselves in any situation. Website: https://johncocolaw.com/  Instagram: https://www.instagram.com/johncocolaw/  Facebook: https://www.facebook.com/johncocolaw/  Where to find me: IG: https://www.instagram.com/jen_gottlieb/    TikTok: https://www.tiktok.com/@jen_gottlieb     Facebook: https://www.facebook.com/Jenleahgottlieb    Website: https://jengottlieb.com/    My business: https://www.superconnectormedia.com/     YouTube: https://www.youtube.com/@jen_gottlieb

Do you need to fake it till you make it to build a successful personal brand? The truth is, you don't! In today’s episode, we dive into the concept of "faking it" and why you don't need it to create meaningful content or grow a personal brand. You don’t have to be perfect, and you certainly don’t have to pretend to be an expert.  You’ll discover that you can build a connection with your audience by showing them the real you—your enthusiasm, your growth, and even your mistakes. And guess what? People will resonate with you more when you're real, not when you're pretending to have all the answers. So, stop waiting for the perfect moment. Start creating and sharing content today, even if you're not an expert yet. It's time to embrace your authenticity, document your journey, and let your audience come along for the ride. Tune in now and take the first step to building your authentic personal brand. "It's okay to be an enthusiast before you are an expert." ~ Jen Gottlieb In this Episode: - Building a personal brand without faking it  - Be an enthusiast before an expert - Start teaching what you know - Collect and display social proof - Leverage other people's audiences (OPA) - Build a personal brand feedback loop - The power of consistency in content creation - Final thoughts on creating an authentic personal brand Looking for a smarter way to manage your inbox? Get Notion right now at notion.com/jeng and experience an inbox that actually thinks like you. Where to find me: IG: https://www.instagram.com/jen_gottlieb/    TikTok: https://www.tiktok.com/@jen_gottlieb     Facebook: https://www.facebook.com/Jenleahgottlieb    Website: https://jengottlieb.com/    My business: https://www.superconnectormedia.com/     YouTube: https://www.youtube.com/@jen_gottlieb

Are you feeling the weight of perfectionism and the constant need to achieve? Dr. Tiffany Moon’s journey is a testament to how the pressure to be perfect can hinder personal fulfillment. As a successful physician, reality TV star, and author, she realized that her life was driven by external accomplishments rather than internal joy.  In this episode, Dr. Tiffany shares how she stopped living for external validation and began to align her actions with her authentic self. From moving away from toxic friendships to learning the art of saying no, she highlights the importance of setting boundaries and prioritizing well-being over societal expectations.  Her book, Joy Prescriptions, explores this journey and how Dr. Tiffany applied her doctor’s mindset to prescribe joy in everyday life. It’s not just about removing the negative but creating space for what truly brings happiness.  Ready to start your own journey of self-rediscovery? Join us as we explore how you can overcome perfectionism, prioritize joy, and live a life that feels as good on the inside as it looks on the outside.  "To stop filling your bucket with the wrong things is a mindset shift. First, you change your mindset, and then you start doing things that fall in line with the new mindset." ~ Dr. Tiffany Moon In this Episode: - Meet Dr. Tiffany Moon - Behind the scenes of the Real Housewives of Dallas - Jen's Real Housewives experience - Dr. Tiffany's upbringing, academic achievements, and career - Escaping the trap of perfectionism and reconstructing Life - Finding healing: therapy, self-help books, and a "friends" audit - Tiffany's Real Housewives experience  - Dr. Tiffany’s life and career after her awakening - How to pre-order the Joy Prescriptions book  About Dr. Tiffany Moon: Dr. Tiffany Moon is a board-certified anesthesiologist, entrepreneur, and author. She is a proud mother of twins and a dynamic television and social media personality. Dr. Tiffany graduated from Cornell University at 19, earned her medical degree with Alpha Omega Alpha Honors from UT Southwestern, and completed her anesthesiology residency at UCSF. She has been named one of D Magazine’s Best Doctors, authored over 50 peer-reviewed publications, been recognized as a Distinguished Educator by the American Society of Anesthesiologists, and serves as an Oral Board Examiner for the American Board of Anesthesiology. She is the founder and CEO of Aromasthesia Candle Company, Three Moons Wine, and LeadHer Summit. Her debut book, Joy Prescriptions—a powerful exploration of overcoming perfectionism and finding joy through gratitude, self-compassion, and connection—will be published in May 2025. Pre-order Joy Prescriptions: https://www.joyprescriptions.com/  Website: https://www.tiffanymoonmd.com/  Instagram: https://www.instagram.com/tiffanymoonmd/  Facebook: https://www.facebook.com/tiffanymoonmd  Where to find me: IG: https://www.instagram.com/jen_gottlieb/    TikTok: https://www.tiktok.com/@jen_gottlieb     Facebook: https://www.facebook.com/Jenleahgottlieb    Website: https://jengottlieb.com/    My business: https://www.superconnectormedia.com/     YouTube: https://www.youtube.com/@jen_gottlieb

Have you ever considered that your negative emotions about change could be your greatest superpower instead of your biggest obstacle? Well, today, I sit down with keynote speaker Cassandra Worthy to explore how we can transform our emotional response to change into fuel for growth and innovation. After years as a chemical engineer in corporate America, Cassandra discovered her calling was helping others navigate change by harnessing their emotions rather than suppressing them. Cassandra breaks down her "Change Enthusiasm" framework, explaining how we can move from simply feeling emotions to transforming them into productive energy. We also discuss the misconception of resilience - it's not about pushing through exhaustion, but rather about strategic recovery and reflection. If you are ready to transform how you approach change management, listen to the full episode and download a free chapter of Cassandra’s book so you can begin your journey to becoming a Change Enthusiast!"You can make a conscious choice to start changing your emotional signature. It's not about emotional suppression. It's emotional regulation." ~ Cassandra WorthyIn this Episode:- Meet Cassandra Worthy- Cassandra’s journey to becoming a keynote speaker- Navigating change in the era of generative AI- Harnessing emotional intelligence- Transforming emotional energy into your superpower- How to influence others with positive energy- Leveraging AI tools in business operations- Navigating AI integration in corporations- The psychology behind human resistance to change- The importance of recovery and self-care during changeThe 'Unfair Advantage' Method: Use AI to Double Revenue and Work LessGet insider access as entrepreneur and business expert Chris Winfield reveals his 5-day AI client-attraction system: https://bit.ly/JenGottliebShowAbout Cassandra Worthy:Cassandra Worthy is the founder and CEO of Change Enthusiasm Global, a dynamic keynote speaker, author, and consultant specializing in guiding organizations through significant transformations. Drawing from nearly two decades of experience in the consumer packaged goods industry, including navigating a $5 billion acquisition, she developed the Change Enthusiasm framework. The framework empowers individuals to harness their emotions, fostering resilience and adaptability during periods of change. Cassandra has collaborated with Fortune 500 companies such as Procter & Gamble, Allstate, and WeWork, helping them cultivate cultures that not only survive but thrive through change.Website: https://cassandraworthy.com/ Instagram: https://www.instagram.com/cassandra_worthy_speaker/Facebook: https://www.facebook.com/wearechangeenthusiasts/ LinkedIn: https://www.linkedin.com/in/cassandra-worthy-802ab623/ Where to find me:IG: https://www.instagram.com/jen_gottlieb/   TikTok: https://www.tiktok.com/@jen_gottlieb    Facebook: https://www.facebook.com/Jenleahgottlieb   Website: https://jengottlieb.com/   My business: https://www.superconnectormedia.com/    YouTube: https://www.youtube.com/@jen_gottlieb

The tools that could 10x your business growth are already at your fingertips—you just haven’t explored them yet! Today, I am hosting my husband, Chris Winfield, who's gone deep down the AI rabbit hole, to share the latest tools and strategies that every entrepreneur needs to know. From better content creation and client engagement to building smarter systems, we cover the exact ways AI can help you grow without burning out. We explore platforms like Claude, Grok, ChatGPT, and HoneyBook, an all-in-one business manager that’s integrating AI in a way that saves time and streamlines operations.So, if you've been overwhelmed by AI or unsure where to start, this conversation will flip the switch. Join us and discover how to embrace the shift and make AI your most valuable team member. Want to see these tools in action? Be sure to join our upcoming free training with HoneyBook."You don't need AI to get it perfect, and you don't want to just take the first output and go with it. You want to always review everything that AI is creating for you." ~ Chris WinfieldIn this Episode:- Meet Chris Winfield- Exploring initial AI tools and the introduction of ChatGPT- Mastering AI Tools and their impact on business - Practical AI applications for entrepreneurs- How to create prompts and avatars for writing GPTs- Advanced AI tools and techniques for business- Future of AI and its implications- Why it is critical to explore AI tools daily- Conclusion and upcoming webinar with HoneyBookJoin Our Free Webinar With HoneyBook: https://bit.ly/FreeWebinarWithHoneyBook About Chris Winfield:Chris Winfield is a renowned entrepreneur, writer, and coach dedicated to helping individuals build authentic relationships to achieve their goals. As the founder of Super Connector Media, he emphasizes the power of genuine connections over traditional networking tactics. Chris has contributed to publications like Inc., Entrepreneur, Business Insider, and TIME, and has been featured in over 200 media outlets, including The Wall Street Journal, The New York Times, and NBC’s Today Show. He has assisted clients from companies such as Disney, Virgin, and Intuit in leveraging media and influencer relationships to enhance credibility and drive profit.Website: https://www.chriswinfield.com/ Instagram: https://www.instagram.com/chriswinfield/ Facebook: https://www.facebook.com/thechriswinfield LinkedIn: https://www.linkedin.com/in/chriswinfield/ Where to find me:IG: https://www.instagram.com/jen_gottlieb/   TikTok: https://www.tiktok.com/@jen_gottlieb    Facebook: https://www.facebook.com/Jenleahgottlieb   Website: https://jengottlieb.com/   My business: https://www.superconnectormedia.com/    YouTube: https://www.youtube.com/@jen_gottlieb

Have you ever desperately clung to a relationship out of fear or the sunk cost fallacy? What if the relationships that come into your life aren't always meant to stay forever but instead are there to guide you through specific seasons?In this episode, I share a personal story from my vacation in Greece that came back to me at exactly the moment I needed to remember it. I was too afraid to take a six-hour hike without a professional guide, and then the universe sent me three stray dogs who led the way. But this isn't just about a magical experience with some adorable pups. It's about recognizing when we're holding onto relationships past their purpose and how to find the courage to let go when the journey is complete. So, if you're struggling to release someone who's clearly meant to move on, this episode is for you! And when you identify your own "guiding dogs" that you need to release, DM me—I want to hear your story!"Sometimes relationships come into our lives for a season or a reason, and it's unbelievably important that we give ourselves permission to let go." ~ Jen GottliebIn this Episode:- Creating content with minimal technology- Lessons from Jen’s hiking adventure in Greece- Learning when to let go of relationshipsWhere to find me:IG: https://www.instagram.com/jen_gottlieb/   TikTok: https://www.tiktok.com/@jen_gottlieb    Facebook: https://www.facebook.com/Jenleahgottlieb   Website: https://jengottlieb.com/   My business: https://www.superconnectormedia.com/    YouTube: https://www.youtube.com/@jen_gottlieb

Have you ever tried taking a walk with intention? What if every step of your next walk could lead you closer to manifesting your dreams, reconnecting with your authentic self, or preparing for your next big opportunity? In this unique solo episode, I’m sharing one of my most powerful tools for personal growth: Wonder Walks. I invite you to join me on one of my walks along the beach as we explore how you can use this simple yet profound practice to tap into your inner power and manifest your dreams. From visualization techniques to a self-reflection guide that reconnects you with your true self, you’ll learn how to adopt this practice for personal development.  If you enjoy this episode and want more of this impromptu walking podcast style, I’d love to hear from you. Send me a DM with your thoughts on Wonder Walks and let me know how you’re incorporating them into your life. "The important part is to feel the way you would feel if you already had that thing—as if you were the person in the future that has done the thing that you want to do." ~ Jen GottliebIn this Episode:- Introducing the concept of Wonder Walks- How Jen uses Wonder Walks- How to start your Wonder Walk- Using Wonder Walks for manifestation- Reconnecting with your authentic self through Wonder Walks- Using Wonder Walks to prepare for keynote speeches- Conclusion and feedback requestWhere to find me:IG: https://www.instagram.com/jen_gottlieb/   TikTok: https://www.tiktok.com/@jen_gottlieb    Facebook: https://www.facebook.com/Jenleahgottlieb   Website: https://jengottlieb.com/   My business: https://www.superconnectormedia.com/    YouTube: https://www.youtube.com/@jen_gottlieb