Podcast
The Jen Gottlieb Show
Hosted by Cloud10 · EN
What if today was the day you dared yourself to do what you've always wanted? Welcome to the Jen Gottlieb Show! Each week, join your host, Jen Gottlieb, for powerful, punchy episodes that will leave you inspired to dream big and live boldly. If you are ready to create change in your life, this podcast is a must-listen. Be ready to laugh, learn and take action to become who you were always meant to be. It's time to step out of your comfort zone and into your best life...one dare at a time.
17episodes
Episodes
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Jen’s Favorite Episode: It Is Never Too Late to Answer Your Calling with Steven Pressfield
3d ago00:14:25Tap to summarizeI'm revisiting one of my favorite conversations with bestselling author Steven Pressfield, whose wisdom on fear, resistance, and creativity has inspired millions. If you've been sitting on an idea, delaying your next move, or wondering why the work that matters most feels the hardest to begin, this episode will give you the perspective—and the push—you need.When Steven Pressfield published The Legend of Bagger Vance, many called him an overnight success. What they didn't see were the 30 years of failed novels, unproduced screenplays, and stretches of homelessness that came before it.Few conversations left an impact on me as this one did. Steven is now in his eighties and still creating, doing what he loves, and showing no signs of stopping. I never thought about fear the same after this podcast, thanks to Steven's words. Watch the full episode here: https://youtu.be/K3Z8bcnvNlU "It's like the old story of an overnight success that only takes you 30 years." ~ Steven PressfieldIn This Episode:- Finding your authentic creative voice- How to work with the muse- A simple process for developing great ideas- Why resistance means you're on the right path- Self-doubt as a sign of growth- What a shadow career really isAbout Steven PressfieldSteven Pressfield is the author of The War of Art, which has sold over a million copies worldwide and has become essential reading for writers, artists, and entrepreneurs. His debut novel, The Legend of Bagger Vance, was made into a film starring Matt Damon and Will Smith. His other novel, Gates of Fire, is required reading at West Point. Before his breakthrough at 52, he spent decades failing as a novelist and screenwriter, at times living out of his car. His latest novel, The Arcadian, was released in May 2026.IG: https://www.instagram.com/steven_pressfield/ X: https://x.com/SPressfield Website: https://stevenpressfield.com/ 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
Transcribe →From Selling $35 Tickets Door to Door to Million Dollar in a Month with Leanne Lopez Mosley
1w ago00:53:57Tap to summarizeLeanne Lopez Mosley once stood at the bottom of her neighbors' driveways, talking herself out of knocking on their doors to sell $35 event tickets. A toddler at home, a corporate job she was desperate to leave, and zero customers to speak of. Who knew just a few years later she would be making a million per month?Well, Leanne did. She made $500,000 in her first full year, then had a baby, quit live launching, and crossed a million dollars in the same year. The secret was not working harder. It was getting obsessively specific about who she was talking to and what she was selling them.Leanne walked me through Freedom Funnels, the system behind her consistent million-dollar months with no sales calls and under 16,000 followers.If you enjoyed our conversation, you should definitely check out Leanne's Soft Girl Millions Show at https://www.richqueen.com/the-soft-girl-millions-show, and if you want to see her live, grab your spot at Soft Girl Millions LIVE at https://www.richqueen.com/rq25-soft-girl-millions-the-mastermind-live-organic-26."It's not courage if you're not taking the action." ~ Leanne Lopez MosleyIn This Episode:- Quitting corporate and selling tickets door to door- How free calls built Leanne's first $500,000 year- Hitting a million dollars while on maternity leave- The offers that got her to her first million- Running her own ads and launching She Makes Bank- Why messaging to one person changes everything- What Soft Girl Millions actually means- If you could call your younger and older selfAbout Leanne Lopez MosleyLeanne Lopez Mosley is a Forbes-featured business strategist and creator of Freedom Funnels, the methodology behind consistent million-dollar months with under 16,000 followers, no live launching, and no sales calls. Known as the Trailblazer of the online coaching space, she teaches female entrepreneurs how to build evergreen sales ecosystems that sell without them. After 11 years in corporate, Leanne built a multi-million dollar business from scratch and is also the host of the Soft Girl Millions Show.IG: https://www.instagram.com/theleannelopezmosley/Facebook: https://www.facebook.com/GROW.withleanne/Website: https://www.richqueen.com/Where to find me:IG: https://www.instagram.com/jen_gottlieb/TikTok: https://www.tiktok.com/@jen_gottliebFacebook: https://www.facebook.com/JenleahgottliebWebsite: https://jengottlieb.com/My business: https://www.superconnectormedia.com/YouTube: https://www.youtube.com/@jen_gottlieb
Transcribe →From Making $63 in the First Year to Being Worth $20M with Maria Wendt
2w ago00:33:00Tap to summarizeAbout 1 in 5 businesses fail within their first year. So when you make $63 in year one and $350 in year two, most people would have quit. Maria Wendt didn't.She now runs an eight-figure business with over 150,000 customers, a million-dollar month, and an average of $2,500 per reel, selling products that cost around $85. She has a team of eight, no company meetings, and launches roughly one new product every single week.I brought her on to understand how she got there, and why she walked away from making $1M a year in high-ticket coaching to build something completely different. "I made $63 in my first year and $350 in my second year, and yet I've made over $20 million now." ~ Maria WendtIn This Episode:- How Maria started and went from $63 to $20 million- The million-dollar business she walked away from- Eight figures, a team of eight, and zero meetings- How Maria tracks exactly how much each reel makes her- Saying your biggest goals out loud without apology- The answer to growth is almost always more volume- Maria Wendt's advice on the best way to begin your business journeyAbout Maria WendtMaria Wendt is an eight-figure online business educator based in Orange County, California. She started as a freelance graphic designer before pivoting into teaching marketing and eventually building one of the most recognized low-ticket course businesses in the online space. She has over 150,000 customers, a catalog of 300 products, and runs a lean team of eight out of an in-person office. Her mission is to help millions of people make a few extra thousand dollars a month rather than help a few people make millions.Where to find Maria Wendt:IG: https://www.instagram.com/maria.wendt/?hl=en Facebook: https://www.facebook.com/p/Maria-Wendt-Official-100090621002736/ Website: https://www.mariawendt.com/ 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
Transcribe →How to Break Free From Burnout with CEO of Boss Babe Natalie Ellis
3w ago00:50:48Tap to summarizeNatalie Ellis had millions of followers, a full team, and a fancy LA office by the time she was 25. Then one day, she got on a regular Zoom call and said, "I quit. I no longer wish to be CEO of this company."How do you build a female entrepreneurship platform? How do you make it one of the biggest of its kind in the world? And how do you walk away from something like that? Those were some of the questions I had in mind before sitting down with today's guest.During our conversation, she breaks down what makes content actually convert. Why audience growth and revenue growth are two completely different things. And most importantly, how she went from burning out to making over $2.2 million while completely offline for 12 weeks. "Audience growth does not equal business growth, and audience growth does not equal revenue." ~ Natalie EllisIn This Episode:- Introduction: how Natalie built Bossbabe- Seeing Instagram's potential before anyone else- The type of content that makes people buy- Why follower count and revenue have nothing to do with each other- The Zoom call where she quit and what came after- Mindset before systems, and the discipline of staying simple- How Jen and Natalie each use AI for content- Why right now is the time to build- Where to find Natalie and get her book About Natalie EllisNatalie Ellis is the founder and CEO of Bossbabe, one of the largest online communities and education platforms for female entrepreneurs, with over 4 million followers and more than $20 million in course and membership revenue. She is also the co-founder of glōci, host of the Bossbabe Podcast, and an angel investor in women-led businesses. Her work has reached thousands of students through her online courses, all built through organic social media with no paid ads. Natalie wrote the Freedom-Based Business Method, her playbook for building a business that generates revenue without requiring you to run every part of it yourself.IG: https://www.instagram.com/iamnatalie/ Website: https://www.natalie-ellis.com/ Get Natalie's Book: https://bossbabe.com/buythebook 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
Transcribe →Jen’s Favorite Episode: Sahil Bloom Reveals Why Everything You Know About Success Is Wrong
May 2900:15:38Tap to summarizeAt just 30, Sahil Bloom had everything society told him he needed. The house, the job, the salary, and everything else on the list. And yet, he was miserable.This episode is a replay of one of my favorite conversations on this show. Sahil's story had a pretty normal beginning. He set goals, worked hard, and hit his goals. Except when he got there, something felt off.He was living 3,000 miles away from his family, drinking seven days a week, all while pretending everything was fine. So he stopped and asked himself a question most people are too afraid to ask. Am I even playing the right game? What follows in our conversation is everything he found on the other side of that question.Watch the full episode here: https://youtu.be/cgJ-NpUmGSE "Unless you create your own definition of success, you will never feel successful." ~ Sahil BloomIn This Episode:- When you feel empty despite hitting every goal- Why money became the way we measure success- Why “later” is just another word for “never”- How investing in the right things compounds over time- The “Life Razor” and why everyone needs one- How the stories we tell ourselves shape our futureAbout Sahil BloomSahil Bloom is a New York Times bestselling author, entrepreneur, and investor on a mission to positively impact one billion lives. A Stanford graduate, he spent seven years in high finance before walking away from the traditional path to redesign life on his own terms. His debut book, The 5 Types of Wealth, redefines what it means to live a wealthy life, making the case that true fulfillment goes far beyond money. Over 800,000 people read his newsletter, The Curiosity Chronicle, every week. He is also the owner of SRB Holdings and the managing partner of SRB Ventures, an early-stage investment fund.IG: https://www.instagram.com/sahilbloom X: https://x.com/SahilBloom Website: https://www.sahilbloom.com/ 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
Transcribe →How Jen Gottlieb Built a Speaking Career From Scratch with Lisa Johnson
May 2200:42:08Tap to summarizeToday's episode is a throwback to a keynote Q&A I did with Lisa Johnson at one of her live events. We get into building a speaking career from nothing, the daily habits that got me there, what changed when my Instagram started blowing up, and how Stage Leaders came to life during one of the hardest times of my life. Hope you enjoy!"Confidence comes from consistently sticking with the commitments you make with yourself." ~ Jen GottliebIn This Episode:- Why Jen went from actress to entrepreneur- How Instagram led to Jen's first speaking opportunity- How doing events with Chris became her speaker boot camp- Why imposter syndrome is actually a sign of growth- The mindset shift behind Jen's Instagram explosion- The story behind Stage Leaders- The four pillars of Influence- Jen and Chris’ working relationshipAbout Lisa JohnsonLisa Johnson is a multi-seven-figure business strategist who makes 90% of her income through passive and semi-passive income streams. Her debut book, Make Money Online, made the Sunday Times bestseller list, and her podcast has been downloaded over 500,000 times, reaching number one in the business podcast charts. She has been featured on the BBC's Women's Hour, The Telegraph, The Guardian, Psychologies, Fast Company, and Forbes, where one of her articles garnered over 250,000 views in a week.IG: https://www.instagram.com/lisajohnsonstrategist/Website: https://lisajohnson.com/Where to find me:IG: https://www.instagram.com/jen_gottlieb/TikTok: https://www.tiktok.com/@jen_gottliebFacebook: https://www.facebook.com/JenleahgottliebWebsite: https://jengottlieb.com/My business: https://www.superconnectormedia.com/YouTube: https://www.youtube.com/@jen_gottlieb
Transcribe →From Zero to Half a Million Subscribers with Amy Landino
May 1500:43:49Tap to summarizePersonal branding looks easy from the outside. Just be yourself, show up, and let your personality do the work. Then the camera turns on, and suddenly it's not so simple anymore.Amy Landino never set out to become a personal branding expert. Back in 2007, she just wanted to make a nice wedding video for a friend. But something about that experience stuck with her.That one video turned into a YouTube channel. The channel turned into a business. And the business eventually became two seven-figure media companies and a global audience in over 100 countries.In about 40 minutes, Amy walks us through what she learned from every pivot in her journey and the strategies she uses today to turn content into clients. "If I believe in it first, everybody else will get on board." ~ Amy LandinoIn This Episode:- How a wedding video started it all- Pivoting your brand without losing your audience- Why the best content strategy is meeting people where they are- Talking to your audience like they are already your clients- How to use Instagram Stories to test content before going all in- The BREAK formula for hooking viewers in the first 30 seconds- How to market a book by borrowing other people's audiencesAbout Amy LandinoAmy Landino is a three-time bestselling author, keynote speaker, and the award-winning creator behind AmyTV. She has built two seven-figure media companies, amassed nearly half a million subscribers and 37 million views, and grown a readership spanning more than 100 countries. She has spoken on stages for Adobe, Oracle, LinkedIn, and YouTube, and has been featured on The Tamron Hall Show, Fortune, CNBC Make It, and Business Insider. Her latest book, Good Morning, Good Life, is available in bookstores everywhere.IG: https://www.instagram.com/schmittastic/ YouTube: https://www.youtube.com/amytv LinkedIn: https://www.linkedin.com/in/amytv Website: https://amylandino.com/ Get Amy's Book: https://goodmorninggoodlife.com 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
Transcribe →How to Get Booked and Paid as a Speaker with Zach Nadler
May 800:45:34Tap to summarizeMost people have stood up and spoken in front of a crowd at least once. But turning that into a career, or even a paycheck, is something most speakers never figure out.I brought in Zach Nadler, Co-Founder and CEO of VaynerSpeakers, because he knows exactly how this industry works, and he held nothing back.We got into what event planners actually look for, how to build a reel that opens doors, what your speaking fee should really be, and why LinkedIn might be the most underrated tool speakers are not using. If you want to get on stages and get paid to be there, this one is for you." You have to start small. You have to be willing. You also have to put the work in. Nobody's gonna come knocking at your door (with opportunities)." ~ Zach NadlerIn This Episode:- How Zach went from CAA to co-founding VaynerSpeakers- What makes a great speaker- The assets every speaker needs to get booked- Why event planners are now requesting full speech footage- How to set your speaking fee- How to negotiate without losing your value- Why value exchange matters more than money- How to book your first stages- Why LinkedIn is the most underrated tool for speakersAbout Zach NadlerZach Nadler is the Co-Founder and CEO of VaynerSpeakers, which he launched in 2018 alongside Gary Vaynerchuk. Before that, he was a top sales agent at CAA, representing talent including Al Pacino, Malala Yousafzai, President Joe Biden, and Arnold Schwarzenegger. He also spent three years as Head of Programming for VeeCon, the first NFT-ticketed super conference. Over the course of his career, Zach has driven nearly $100M in sales and booked keynote speakers at close to 4,000 events.Connect with Zach IG: https://www.instagram.com/zachnadler/His business: https://www.instagram.com/vaynerspeakers/Website: https://vaynerspeakers.com/Book a 1:1 with Zach: https://intro.co/ZachNadlerWhere to find me:IG: https://www.instagram.com/jen_gottlieb/TikTok: https://www.tiktok.com/@jen_gottliebFacebook: https://www.facebook.com/JenleahgottliebWebsite: https://jengottlieb.com/My business: https://www.superconnectormedia.com/YouTube: https://www.youtube.com/@jen_gottlieb
Transcribe →The Book Strategy That Made Chandler Bolt $7 Million in 12 Months With Chandler Bolt
May 100:35:17Tap to summarizeIf writing a book has been on your someday list forever, this one's for you.I brought in Chandler Bolt, CEO of selfpublishing.com and author of 7 bestselling books, because honestly, I had questions. I traditionally published my own book, and I still wasn't sure I made the right call. So we got into all of it, the real difference between self-publishing and traditional publishing, why the bestseller list obsession might be costing you more than you think, and how a book can become your best client-generating tool.And I'll be honest, by the end of this conversation, I felt like I'd just paid for a private coaching session. Chandler has built an eight-figure business almost entirely off books, with zero social media until five months ago. So if you've ever thought about writing a book, or you have one and you're not squeezing everything out of it, you're going to want to stick around for this one. "Give away all of your best stuff for free, and people will pay you to tell it to them again." ~ Chandler BoltIn This Episode:- Self-publishing vs traditional publishing- How to have a successful book launch in 2026- Why chasing bestseller lists is the wrong goal- How to use a book to bring in clients- How Chandler's team speaks at 100 events a year- Deciding on audiobooks, hybrid publishing, and book stores- How to work with Chandler and write your bookAbout Chandler Bolt Chandler Bolt is a Forbes 30 Under 30 honoree, college dropout, and CEO of selfpublishing.com. He built the company into a $75M business and an INC 5000 company four years running, almost entirely off books and with zero social media presence until recently. He is the author of 7 bestselling books, including "Published," and his mission is to help 100,000 people publish a book by 2035.Free Book Publishing Consultation: http://selfpublishing.com/jenInstagram: https://www.instagram.com/realchandlerbolt/ YouTube: https://www.youtube.com/@ChandlerBoltOfficial Website: https://selfpublishing.com/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
Transcribe →How to Use AI to Get 3 Hours of Work Done in 15 Minutes With Chris Winfield
Apr 2400:21:12Tap to summarizeAre you using AI in your business, or are you still just asking ChatGPT to write your captions and then calling it a day?I'll be completely honest with you. AI overwhelms me too! Every day, something new drops, and keeping up feels impossible. So I brought in my husband and business partner, Chris Winfield, who has gone fully all in on this, to break it all down for us.Chris explains the difference between the AI tools you already know and AI agents, the kind that actually go out and execute tasks for you. We get into what it looks like to have your own AI employee handling the work that's been sitting on your to-do list for months, and why the people who move on this now will be way ahead."You just need the skills. The skills are transferable. It doesn't matter what the technology is or what the product is, even if it goes away or a better one comes along." ~ Chris WinfieldIn This Episode:- Why everyone in AI feels overwhelmed and why that's okay- AI agents vs. AI chatbots and the difference that matters- Real examples of what an AI agent can do for your business- Why AI employees are changing the way small businesses operate- How Chris compressed a 3-hour content workflow into 15 minutes- What AI will look like in 5 years and how it will impact business- How to get your own AI employee and get ahead right nowAbout Chris Winfield:Chris Winfield is an entrepreneur, co-founder of Super Connector Media, and a contributor to Inc. and Entrepreneur Magazine. His work has been featured in the Wall Street Journal, the New York Times, Forbes, Fast Company, NBC's Today Show, USA Today, and over 200 other outlets. He has worked with clients from companies including Disney, Virgin, and Intuit, helping entrepreneurs build credibility, grow their media presence, and make the right connections.Connect with Chris:IG: https://www.instagram.com/chriswinfield/LinkedIn: https://www.linkedin.com/in/chriswinfield/Website: https://www.chriswinfield.com/Where to find me:IG: https://www.instagram.com/jen_gottlieb/TikTok: https://www.tiktok.com/@jen_gottliebFacebook: https://www.facebook.com/JenleahgottliebWebsite: https://jengottlieb.com/My business: https://www.superconnectormedia.com/YouTube: https://www.youtube.com/@jen_gottlieb
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