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    Business

    the bossbabe podcast

    Bossbabe is one of the world’s largest communities of ambitious women, with over 4.2 million followers and the top online membership for women entrepreneurs. We’re passionate about helping you build a Freedom-Based Business™ to make more money + live a lifestyle you love. Every week, the bossbabe podcast brings you the real behind-the-scenes of building a wildly successful, profitable + reliable business, plus tools and strategies to make sales on repeat, grow an audience on social media, + create the life you truly want.

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    Copyright: © e4d410a0-90cb-11f1-83a6-4b34022a930e

    • Apple Podcasts
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    Latest Episodes:
    Founder of Kit Reveals How to Make 7 Figures Off a Small Email List Oct 13, 2026
    Show notes

    If you think your email list is too small to monetize or convert, today's guest will prove you wrong.


    In this episode, founder of Kit Nathan Barry reveals the secrets behind million-dollar email lists. He breaks down how to clean your email list, what to sell in your newsletters, and how to target high-value subscribers to convert. He also walks through his process for building flywheels that compound newsletter growth and revenue over time.


    In this episode, Natalie and Nathan discuss:

    (01:02) Why Every Email List Should Make $1 Per Subscriber

    (05:34) The Best Cadence for Sending Emails

    (13:42) The Right Way to Clean Your Email List in 2026

    (21:57) How Kit Enables You to Identify High-Value Subscribers

    (24:48) Creating Low-Friction, High-Conversion Flywheels

    (30:20) The 30-Day Test for Growing Your Email List From Nothing

    (38:06) Is AI Killing Lead Magnets?

    (43:19) What the Most Profitable Email Lists Are Doing

    (50:02) Why a Big Audience Isn't Always Beneficial

    (55:29) Big List, Low Revenue? Fix This

    (1:03:46) How to Learn the Skill of Making Money


    Nathan Barry is a creator, author, speaker, designer, and the founder of Kit, an email marketing platform built for creators. He began as a designer and author, using self-published books and email marketing to generate creator income before building Kit as a broader platform for creator businesses. He advocates audience ownership, teaching what you know, sustainable monetization, and building products rather than relying only on personal brand attention.


    Sponsored By:

    FreshBooks - Get FreshBooks for less than $3 a month for your first four months at ⁠FreshBooks.com/podcast⁠.

    Faire - Sign up today and get 50% off your first wholesale order, up to $100 at ⁠faire.com/bossbabe⁠.

    AG1 - Save 20% on your first subscription order of AG1 Next Gen or AG1 Pro at ⁠drinkAG1.com/bossbabe.

    ⁠Hostinger - Go to ⁠Hostinger.com/bossbabe⁠ and use code BOSSBABE for 10% off.


    Resources Mentioned:

    Kit

    Try Subscriber Signals on Kit

    Preorder Nathan’s Book, The Ladders of Wealth


    Connect with Nathan:

    Website

    LinkedIn

    Instagram

    X

    Podcast


    Connect with Natalie:

    Instagram

    LinkedIn

    Website

    YouTube

    Natalie’s Book, The Freedom-Based Business Method


    email marketing, email marketing strategy, Nathan Barry, Natalie Ellis, Kit, creator economy, audience growth, email list building, newsletter growth, digital products, entrepreneurship, business growth, AI for business, creator business, email automation, sales funnels, online business, monetize your audience, make money online, revenue per subscriber, creator flywheel, content marketing, personal brand, build an audience, business systems


    Inside Create & Cultivate's $3M Festival With CEO Marina Middleton Oct 06, 2026
    Show notes

    How do you sell 3,800 tickets to an industry-leading business event with zero ad spend and a team of only seven people?


    In this episode, Create & Cultivate CEO and Partner Marina Middleton explains the fully organic growth strategy that has scaled Create & Cultivate into the biggest festival for women entrepreneurs and business leaders, from user-generated content to placing a strong focus on value in every asset. She reveals why she doesn't pay Martha Stewart, the Kardashians, or other A-list celebrities to speak at the event and her outreach framework for speakers, guests, and brands. Finally, she and Natalie break down the unique challenges women entrepreneurs face in friendships, marriage, and public perception.


    In this episode, Natalie and Marina discuss:

    (01:24) How We're Building a Tentpole Event for Women Entrepreneurs

    (05:04) Are Paid Ads The Best Way to Grow From Scratch?

    (09:08) Year-Round Organic Promotion for Create & Cultivate

    (12:04) Putting On a $3 Million Event With a Seven-Person Team

    (16:54) How to Provide Clear Value to Event Sponsors and Investors

    (20:50) The Balancing Act in High-Achieving Marriages

    (27:14) Identifying Fake Friendships as a Woman Entrepreneur

    (31:47) How to Rebuild Your Relationship with Work and Success

    (35:38) Is Social Media Killing Your Ambition and Burning You Out?

    (40:31) The Unique Challenges of Running a VC-Backed Business


    Marina Middleton is the CEO and Partner of Create & Cultivate, the largest events and media platform advancing women through access to resources, connections, and opportunities. A former corporate strategist turned bootstrapped founder and now VC-backed CEO, Marina has led the launch of the world’s largest festival for women in business and developed CONNECT, the largest AI-powered matchmaking platform for women, transforming how women network and collaborate. She has been featured in Forbes, Inc., and Business Insider, and regularly speaks on entrepreneurship, venture capital, business growth, and building inclusive communities.


    Sponsored By:

    Quince - Get free shipping on your order and 365-day returns at quince.com.

    FreshBooks - Get FreshBooks for less than $3 a month for your first four months at ⁠FreshBooks.com/podcast⁠.

    Faire - Sign up today and get 50% off your first wholesale order, up to $100 at ⁠faire.com/bossbabe⁠.

    AG1 - Save 20% on your first subscription order of AG1 Next Gen or AG1 Pro at ⁠drinkAG1.com/bossbabe.

    ⁠Hostinger - Go to ⁠Hostinger.com/bossbabe⁠ and use code BOSSBABE for 10% off.


    Resources Mentioned:

    This December’s Supper Club in Miami


    Connect with Marina:

    Website

    LinkedIn

    Instagram

    YouTube

    Create & Cultivate


    Connect with Natalie:

    Instagram

    LinkedIn

    Website

    YouTube

    Natalie’s Book, The Freedom-Based Business Method


    event planning, entrepreneurship, women in business, organic marketing, event marketing, event sponsorship, Marina Middleton, Natalie Ellis, Create & Cultivate, event planning tips, event marketing strategy, event sponsorship strategy, event business, event promotion, organic marketing strategy, women entrepreneurs, female entrepreneurs, sell event tickets, event sponsorships, business events, conference marketing, event management, experiential marketing, brand partnerships


    The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 Sep 29, 2026
    Show notes

    Entrepreneurs are rushing to incorporate AI into their workflow and marketing. But modern research warns us against this.


    In this episode, digital entrepreneur and bestselling author Ryan Levesque joins Natalie to break down why audiences are rejecting automation. He also explains why mid-tier offers are losing their profitability, which channels to build your audience on in 2026, and why constantly pursuing business growth comes at a cost.


    In this episode, Natalie and Ryan discuss:

    (01:37) Are $3K Offers Dead?

    (07:49) The Key Driver of Digital Marketing Success in 2026

    (11:38) Why Storytelling and In-Person Events Are So Impactful

    (17:33) Outsourcing Copywriting to AI is a HUGE Mistake!

    (23:46) Where AI Actually Belongs in Your Workflow

    (26:04) Understanding the Right Size for Your Business

    (33:55) The Lifestyle Changes Startup Founders Need to Make

    (39:25) The #1 Platform For Building an Audience That Converts

    (45:33) Why Evergreen Content is Losing Potential for Virality

    (48:55) The Last Competitive Advantage in the Age of AI

    (52:39) When to Resist the Temptation to Scale


    Ryan Levesque is a 7-time Inc. 5000 CEO & Founder and two-time #1 national bestselling author. He’s generated over $100M in revenue and has successfully sold two of his companies. His work has been featured in the Wall Street Journal, Harvard Business Review, Forbes, Entrepreneur, and NBC News. Today, he serves as a Strategic Advisor to multiple businesses and writes a weekly email newsletter, The Digital Contrarian, offering unconventional business wisdom to 100,000+ subscribers.


    Sponsored By:

    Fora Travel - Visit⁠⁠⁠ foratravel.com/bossbabe⁠⁠⁠⁠ to learn how to turn your love of trip planning into a business.

    FreshBooks - Get FreshBooks for less than $3 a month for your first four months at⁠ ⁠FreshBooks.com/podcast⁠⁠.

    Faire - Sign up today and get 50% off your first wholesale order, up to $100 at⁠ ⁠faire.com/bossbabe⁠⁠.

    AG1 - Save 20% on your first subscription order of AG1 Next Gen or AG1 Pro at⁠ ⁠⁠⁠drinkAG1.com/bossbabe⁠⁠.⁠

    ⁠⁠⁠Hostinger - Go to⁠ ⁠Hostinger.com/bossbabe⁠⁠ and use code BOSSBABE for 10% off.


    Resources Mentioned:

    ⁠Ryan’s Article, “The Shape of Enshittification”⁠

    ⁠Ryan's Book, Return to Real⁠

    ⁠Ryan's Newsletter, The Digital Contrarian⁠


    Connect with Ryan:

    ⁠Website⁠

    ⁠LinkedIn⁠

    ⁠Instagram⁠

    ⁠YouTube⁠


    Connect with Natalie:

    ⁠Instagram⁠

    ⁠LinkedIn⁠

    ⁠Website⁠

    ⁠YouTube⁠

    ⁠Natalie’s Book, The Freedom-Based Business Method⁠


    digital marketing, AI marketing, social media marketing, email marketing, AI for business, content marketing, Ryan Levesque, Natalie Ellis, Return to Real, digital marketing strategy, email marketing strategy, marketing trends 2026, AI marketing strategy, content strategy, social media strategy, personal branding, storytelling marketing, marketing automation, online business, audience growth, email list building, creator marketing, human marketing, business growth, digital marketing podcast


    The Five Success Wounds: The Mental Roadblocks Holding You and Your Business Back Sep 22, 2026
    Show notes

    Burnout, imposter syndrome, and people-pleasing may not be the real problem. Today’s episode reveals the hidden success wounds underneath them.


    In this episode, executive coach Brooke Taylor and Natalie discuss why so many high-achieving women tie their self-worth to success and how that pattern can lead to burnout, imposter syndrome, perfectionism, and people-pleasing. Brooke breaks down the five “success wound” archetypes, why ambitious women often over-function in business and relationships, and how personal development can help separate achievement from identity. They also explore success addiction, firstborn-daughter patterns, fulfillment, and how women in business can pursue big goals without constantly feeling like they are not enough.


    In this episode, Natalie and Brooke will discuss:

    (00:00) The Success Wound in Small Business Owners

    (03:58) Why Eldest Daughters Are More Likely to Burn Out

    (07:16) The Drastic Effect of Over-Performing in Every Area of Life

    (10:36) The Five Types of Success Wounds and How They Show Up

    (15:55) How Our Different Parts Show Up in Business

    (20:17) Discovering Who Your True Self Is and Learning to Trust Her

    (24:46) Addressing the Fear of Losing Your Drive While Healing

    (27:51) Imposter Syndrome and Burnout Are Symptoms, Not Causes

    (35:37) Navigating Addictions to Alcohol vs. Success

    (44:38) Tips to Step Into Your True Self as a Business Leader Today


    Brooke Taylor is a keynote speaker, former marketing lead at Google, and executive coach for women in tech, finance, healthcare, and consulting. She’s also the author of Healing the Success Wound, the go-to guide for separating your self-worth from your productivity so you can build a career that actually feels fulfilling.


    Sponsored By:

    Fora Travel - Visit⁠⁠ foratravel.com/bossbabe⁠⁠⁠ to learn how to turn your love of trip planning into a business.

    FreshBooks - Get FreshBooks for less than $3 a month for your first four months at ⁠FreshBooks.com/podcast⁠.

    Faire - Sign up today and get 50% off your first wholesale order, up to $100 at ⁠faire.com/bossbabe⁠.

    AG1 - Save 20% on your first subscription order of AG1 Next Gen or AG1 Pro at ⁠drinkAG1.com/bossbabe.

    ⁠Hostinger - Go to ⁠Hostinger.com/bossbabe⁠ and use code BOSSBABE for 10% off.


    Resources Mentioned:

    Steve Jobs's 2005 Commencement Speech

    Brooke's Book, Healing the Success Wound

    Brooke's Coaching Program, Finally Fulfilled


    Connect with Brooke:

    Website

    LinkedIn

    Instagram


    Connect with Natalie:

    Instagram

    LinkedIn

    Website

    YouTube

    Natalie’s Book, The Freedom-Based Business Method


    burnout, imposter syndrome, people-pleasing, personal development, women in business, Brooke Taylor, Natalie Ellis, success wound, burnout recovery, women entrepreneurs, female entrepreneurs, entrepreneur burnout, overcome imposter syndrome, stop people-pleasing, perfectionism, self-worth, personal growth, success addiction, high-achieving women, women in leadership, business mindset, work-life balance, career burnout, ambitious women, healing burnout, business coaching


    Running a Business, Household, and Brand—Can You Really Do It All? Sep 15, 2026
    Show notes

    As high-achieving women, we often pressure ourselves to be perfect in every area of our lives, including motherhood. But what if being the perfect parent isn’t the goal?


    In this episode, conscious parenting founder Dr. Shefali joins Natalie to discuss her two new books, Raising Conscious Daughters and Raising Conscious Sons. She dives into the value of maternal energy in early childhood and how to balance career growth with focused, present parenting. She also explains why you should welcome your child’s boredom, anger, and urge to control others during play. Finally, she and Natalie break down the trauma and self-limiting beliefs quietly fueling high performers and how to unlearn them.


    In this episode, Natalie and Dr. Shefali will discuss:

    (01:10) The Cost of Taking on Masculine Energy to Scale

    (05:15) Identifying Underlying Trauma Responses in Our Ambition

    (11:14) The Priceless Value of Maternal Energy for Young Children

    (15:49) Why Your Child's Anger Toward You is a Green Flag

    (20:03) Controlling Your Child's Conditions Instead of Behavior

    (23:16) Balancing Ego and Mindfulness as High Performers

    (27:02) Understanding Why Children Play and How to Engage

    (32:25) Teaching Your Children to Be Bored

    (40:54) Antidotes to Common Problems of High-Performing Women

    (49:49) How to Teach Your Children to Prioritize Their Needs

    (53:38) Advice for Women Trying to Do It All


    Dr. Shefali is a New York Times bestselling author and the founder of the revolutionary Conscious Parenting movement, which has transformed the ways in which the world parents their children. She integrates Western psychology and Eastern philosophy to help you heal your past, release your insecurities, and step into your most authentic and empowered self. She is the CEO of the Conscious Parenting and Life Coaching Institute, a globally recognized certification program training coaches in conscious parenting, emotional intelligence, and mindful living that has impacted thousands of families across more than 50 countries.


    Sponsored By:

    Fora Travel - Visit⁠ foratravel.com/bossbabe⁠⁠ to learn how to turn your love of trip planning into a business.

    FreshBooks - Get FreshBooks for less than $3 a month for your first four months at FreshBooks.com/podcast.

    Faire - Sign up today and get 50% off your first wholesale order, up to $100 at faire.com/bossbabe.

    AG1 - Save 20% on your first subscription order of AG1 Next Gen or AG1 Pro at drinkAG1.com/bossbabe.

    Hostinger - Go to Hostinger.com/bossbabe and use code BOSSBABE for 10% off.

    Resources Mentioned:

    ⁠Dr. Shefali’s Book, Raising Conscious Sons⁠

    ⁠Dr. Shefali’s Book, Raising Conscious Daughters⁠

    ⁠Dr. Shefali and her daughter, Maia, on the Parenting & You podcast⁠


    Connect with Dr. Shefali:

    ⁠Website⁠

    ⁠TikTok⁠

    ⁠Instagram⁠

    ⁠YouTube⁠


    Connect with Natalie:

    ⁠Instagram⁠

    ⁠LinkedIn⁠

    ⁠Website⁠

    ⁠YouTube⁠

    ⁠Natalie’s Book, The Freedom-Based Business Method⁠

    conscious parenting, gentle parenting, parenting advice, mom burnout, work life balance, Dr. Shefali, Natalie Ellis, parenting tips, motherhood, working moms, parenting boundaries, conscious motherhood, gentle parenting tips, parenting burnout, parenting mindset, raising children, child development, mom guilt, work life balance for moms, parenting podcast, conscious parent, parenting expert, emotional regulation, healthy boundaries, modern parenting, parenting help


    Advice for High-Achieving Women Facing Burnout Sep 08, 2026
    Show notes

    Most entrepreneurs think we are destined to live a life of stress, burnout, and a busy calendar. Today, we’re proving that wrong and revealing how your business can give you the emotional, financial, and spiritual freedom you’ve always dreamed of.


    In this episode, Natalie Ellis and Lori Harder are joined by a panel of prolific female entrepreneurs to talk about how they overcame intense burnout and found purpose, fulfillment, and freedom in their businesses. They break down how to balance seasons of growth with emotional hardships, how breathwork and intentional presence can make waves in your business, and why authenticity matters to both you and your audience.


    In this episode, the panel will discuss:

    (01:28) The Power of Authenticity in Podcasting

    (06:11) Building Non-Negotiable Social Media Habits

    (09:21) The IG Account That Got 800K Followers After Three Videos

    (13:13) Running a Business From Intuition Over Strategy

    (20:48) Finding Wisdom in Your Deepest Wounds

    (25:30) When Living Your Dreams Leaves You Lonely

    (30:20) How Breathwork Reveals What You Need to Find Fulfillment

    (34:52) How Entrepreneurs Can Balance Massive Growth With Personal Instability

    (38:40) Advice for High-Performing Women Struggling With Vulnerability

    (45:58) A Practical Guide to Abandoning Labels that No Longer Serve You

    (57:03) Why Not Following Your Purpose Hurts the People You Love


    Sponsored By:

    Fora Travel - Visit ⁠https://www.foratravel.com/bossbabe⁠ to learn how to turn your love of trip planning into a business.


    Resources Mentioned:

    Instagram: The Kumar Method

    Lori Harder’s Podcast, Earn Your Happy

     Sacred Woman by Queen Afua

    Powerhouse Women with Lindsey Schwartz

    The CHBT Method in Wellbeing Rituals: Science-Backed Practices for Sustainable Healing and Living by Michael B. Beckwith and Koya Webb

     Get Loved Up Embodied Leadership Academy with Koya Webb


    Connect with Natalie:

    Instagram

    LinkedIn

    Website

    YouTube

    Natalie’s Book, The Freedom-Based Business Method


    Debunking Myths About Social Media, AI, and Hustle Culture Sep 01, 2026
    Show notes

    If you’re struggling to gain traction on social media for your business, this episode will give you the blueprint on how to revitalize your digital marketing strategy and scale your business without burning out.


    In this special interview at the iconic Godmothers bookstore, Jamie Kern Lima interviews Natalie Ellis about her step-by-step formula for creating viral content and building a loyal audience on social media. She also breaks down how she uses Wispr Flow, Claude Code, and Replit to automate mundane tasks and provide a more personalized experience for her community, along with her advice on how entrepreneurs can better regulate their nervous systems to increase performance, productivity, and fulfillment, even in their busiest seasons.


    In this episode, Natalie and Jamie will discuss:

    (00:00) Celebrating BossBabe's Impact on Women Globally

    (09:18) The Cost of Never Being Satisfied

    (17:33) The Myth of Having One Purpose in Life

    (26:07) The Value of Hustle Culture

    (30:56) Nervous System Regulation 101 for Entrepreneurs

    (36:24) My Tested Formula for Creating Content that Goes Viral

    (47:48) Easy Ways You Can Use AI Today to Grow Your Business

    (1:03:30) How to Inspire the Next Generation of Female Entrepreneurs

    (1:08:04) Maintaining Relationships While Healing Generational Trauma

    (01:13:10) When to Seek Investors


    Jamie Kern Lima is an entrepreneur, 2x New York Times bestselling author, and host of the #1 self-improvement podcast in the US, The Jamie Kern Lima Show. She co-founded IT Cosmetics, which she sold to L'Oréal for $1.2 billion in 2016, becoming the first female chief executive officer of a L'Oréal brand. Jamie has been included on Forbes’ list of "America's Richest Self-Made Women" since 2017. She's also an active philanthropist who has funded leadership training in more than 100 prisons and shelters across the US and has donated over $40 million in product and funds to help women face the effects of cancer with confidence.

    Sponsored By:

    Fora Travel - Visit https://www.foratravel.com/bossbabe to learn how to turn your love of trip planning into a business.


    Resources Mentioned:

    Godmothers

    Natalie’s Book, The Freedom-Based Business Method

    Wispr Flow

    Claude Code

    Replit


    Connect with Jamie Kern Lima:

    Instagram

    LinkedIn

    Website

    YouTube

    Jamie’s Podcast, The Jamie Kern Lima Show


    Connect with Natalie:

    Instagram

    LinkedIn

    Website

    YouTube

    Natalie’s Book, The Freedom-Based Business Method


    artificial intelligence, AI tools, AI for business, social media marketing, personal branding, entrepreneurship, content creation, Natalie Ellis, Jamie Kern Lima, BossBabe, Claude Code, Replit, Wispr Flow, AI automation, AI marketing, business automation, social media growth, build a personal brand, audience growth, content strategy, viral content, creator economy, digital marketing, AI for entrepreneurs, business growth, online business, community building


    The #1 Way to Scale Your Brand and Business in the Age of AI Aug 25, 2026
    Show notes

    Want to build an audience that AI can’t replace? Natalie Ellis and Lori Harder reveal the personal branding strategy behind real business growth.


    In this episode, Lori and Natalie discuss how entrepreneurship can create more freedom when it’s built around focus, systems, and community. They break down personal branding, business growth, social media marketing, how to build an audience you actually own, and why that audience can become a powerful advantage in the age of AI. Natalie shares her one-product, one-client, one-funnel, one-platform approach to growth, while Lori explains how podcasting and strategic guest appearances can expand your reach, relationships, and revenue.


    In this episode, Natalie and Lori will discuss:

    (03:47) How Entrepreneurship Creates Freedom

    (07:27) Path to Growth: Hustle Culture or Soft-Life CEO?

    (10:41) Abandoning People’s Expectations of You

    (16:50) How Trauma Can Create Freedom

    (18:01) Future-Proofing Your Business in the Age of AI

    (21:27) Want to Build a Loyal Audience? Do THIS

    (25:47) The Ugly Truth About Launching New Ventures

    (29:39) Podcasting as a Vehicle for Building Online Communities

    (33:49) Replacing Jealousy With Collaboration

    (37:33) The Podcast Industry’s Most Gatekept Rules


    Lori Harder is a serial entrepreneur, author, and founder of beauty and wellness brand Glōci. She has built and scaled multiple million-dollar businesses and hosts the Earn Your Happy podcast, which has surpassed 65 million downloads. Lori also invests in more than 10 companies and helps entrepreneurs grow their brands, businesses, and networks.


    Resources Mentioned:

    Natalie’s Book, The Freedom-Based Business Method

    Mel Robbins’s Podcast, The Mel Robbins Podcast


    Connect with Lori:

    Lori’s Podcast, Earn Your Happy

    YouTube

    Instagram

    LinkedIn

    Website

    Lori’s Book, A Tribe Called Bliss


    Connect with Natalie:

    Instagram

    LinkedIn

    Website

    YouTube

    Natalie’s Book, The Freedom-Based Business Method


    Entrepreneurship, personal branding, business growth, social media marketing, how to build an audience, AI for business, Natalie Ellis, Lori Harder, bossbabe, build a personal brand, audience growth, grow on social media, online business, business systems, business strategy, content marketing, community building, podcast marketing, podcast guesting, entrepreneur mindset, brand building, grow your business, social media growth, AI marketing, freedom based business


    She Built a Million-Dollar Business and Called It a Pretty Prison (the Truth About Revenue, Grief, and Starting Over) Jun 23, 2026
    Show notes

    This is the conversation about the part most founders don't say out loud: the moment you hit the revenue number and feel nothing.

    Natalie sits down with Jenna Wright — a Pilates studio owner who built a 7-figure business from $1,000 and an air mattress. From the outside, she'd made it. From the inside, she was running at 9% profit, paying herself $80K a year, and calling it — in her own words — a pretty prison. So she did what most founders won't: she dismantled it on purpose. They go inside the math (she was running $1.2M at 9% profit, paying herself $80K/year), the team mutiny that finally broke the model, and the deliberate revenue cut from $1.2M to $650K that tripled her margin to 30%.

    If you've ever hit the revenue numbers and felt nothing, this episode is the operating system for what comes next.

    Time Stamps:

    07:40 "Tired at a soul level" — the burnout most founders hide

    10:00 $1,000 and an air mattress: the rebuild from zero

    14:05 $250K to $875K in one year (and the cost it hid)

    19:10 The misery beneath success

    25:15 The team mutiny that broke the business model

    28:33 The math: cutting 4 studios to 2, profit triples

    31:50 "Your business will expose every wound you have"

    33:00 The 7-day retreat that reorganized everything

    40:05 The lessons Jenna is rewriting today

    Resources + Links:

    Pre-Order The Freedom-Based Business Method.

    Follow Jenna: @iam_jennawright

    Learn more about Jenna's Teacher Training

    Follow Jenna Wright + Read Her Substack "The Shift" Where She Documents The Scale-Down Publicly

    Sign Up For Our Free Weekly Newsletter & Get Insights From Natalie Every Single Week On All Things Strategy, Motherhood, Business Growth + More.

    Drop Us A Review On The Podcast + Send Us A Screenshot & We’ll Send You Natalie’s 7-Figure Operating System Completely FREE (value $1,997).


    Are you addicted to work and achievement? Exploring the concept of “never enough” and how to finally unlock alignment. Jun 16, 2026
    Show notes

    In this episode, Natalie sits down with Keren Eldad — coach to some of the world's highest achievers and author of Gilded and the new Gilt Free — to unpack why external success never delivers the safety it promises. Keren shares the three core wounds beneath achievement addiction, the "gilded cage" so many high-achieving women are trapped in, and the surprising income threshold where what you want out of life finally starts to change.

    You'll learn how to recognize the wound driving your hustle, why "assume everyone likes you" became her most viral piece of advice, and the riptide rule for holding onto success without letting it consume you.

    If you've ever achieved everything you set out to and quietly wondered why it's still not enough, this episode is the reframe and the way out.

    Time Stamps:

    03:50 The gilded cage: when the shiny life is the trap

    07:50 "Yes, we're addicts" — achievement as addiction

    15:30 The 3 core wounds behind every overachiever

    18:18 The success coach who still spirals when business slows

    21:34 The $500K line that changes what you actually want

    27:50 "Assume everyone likes you" — the rule that went viral

    38:11 The riptide rule for holding onto success

    48:28 Why scaling might be the wrong goal entirely

    53:46 What real credibility in coaching actually looks like

    Links & Resources:

    Pre-Order The Freedom-Based Business Method.

    Follow Keren: @coachkeren

    Grab a copy of Keren’s book - Gilded: Breaking Free from the Cage of Ambition, Perfectionism, and the Relentless Pursuit of More

    Listen to Natalie on COACHED by Keren Eldad

    Sign Up For Our Free Weekly Newsletter & Get Insights From Natalie Every Single Week On All Things Strategy, Motherhood, Business Growth + More.

    Drop Us A Review On The Podcast + Send Us A Screenshot & We’ll Send You Natalie’s 7-Figure Operating System Completely FREE (value $1,997).



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