433: CEO Mama: Real Talk About the Taboo Topic of Childcare as an Ambitious Mama

In this episode, Natalie and Alex share their own experiences of identity shifts, friendship dynamics, and releasing relationships that were no longer serving them. They talk through the sometimes uncomfortable—but ultimately freeing—process of letting go of the need to be liked by everyone. From shedding layers of societal expectations to cultivating meaningful relationships rooted in authenticity, this episode unpacks how embracing discomfort and setting boundaries can lead to deeper connections and more aligned friendships.  If you’ve ever felt like you’re walking on eggshells, holding back your truth to keep the peace, or struggling to navigate the grief of losing friendships, this episode will leave you feeling seen, understood, and empowered to put yourself first. TIMESTAMPS 00:00 – Introduction: Nashville trips, the joy of spontaneous plans, and finding Gilmore Girls energy in Franklin. 09:30 – The appeal of Franklin: Reflecting on the lifestyle, climate, and the idea of a long-term home. 13:30 – Shedding the “shoulds”: How motherhood shakes up identity and helps you rediscover your core. 19:15 – Commitment-phobes unite: Natalie’s surprising journey from non-committal to rooted. 24:10 – Speaking your truth: Breaking free from people-pleasing and embracing discomfort in relationships. 29:50 – Losing friendships: The grief, growth, and reframing what success looks like in relationships. 35:20 – Walking on eggshells: Why it’s okay to let go of dynamics that drain you and the liberation of saying no. 41:10 – Cultivating meaningful relationships: Identifying who energizes you versus who depletes you. 46:30 – The power of intention: How to set boundaries in friendships and create a close-knit, supportive circle. 52:00 – Productivity myths: Why slowing down and doing less can fuel creativity and alignment. 58:45 – Navigating friendships post-motherhood: Why texting back doesn’t define your relationships. 1:05:30 – The importance of presence: How to enjoy small moments and release the pressure of “habit stacking.” 1:12:00 – Final reflections: Raise your standards, stop settling, and step into 2025 with intention and clarity. RESOURCES + LINKS Join The Société: Our Exclusive Membership To Help You Build A Freedom-Based Business. Sign Up For Our Weekly Newsletter & Get Insights From Natalie Every Single Week On All Things Strategy, Motherhood, Business Growth + More.  Learn Natalie’s Proven Method for Building a Profitable, Predictable, Freedom-Based Business and Get Back to WHY you Became an Entrepreneur in this FREE 90-Minute Training. 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)  FOLLOW bossbabe: @bossbabe.inc Natalie Ellis: @iamnatalie Alex Wombwell-Povey: @iamalexandriamaria

Natalie and Lindsay dive into surprising data about modern parenting, revealing how working mothers today spend MORE time with their kids as stay-at-home moms did in the 1970s. They explore how societal shifts, multitasking, and parenting expectations shape modern family life and what this means for entrepreneurs balancing business and motherhood. The conversation also uncovers the importance of nervous system regulation for business owners, how to build calm companies, and predictions about the impact of AI on the influencer world and mental health. TIMESTAMPS 0:13 - Unpacking a tweet that sparked the conversation: Why working mothers today spend more time with their kids than stay-at-home mothers in past decades. 2:08 - The cultural shift in parenting expectations and the rise of “helicopter parenting.” Why unstructured playtime matters for mental resilience in children. 6:22 - How changes in safety, living environments, and social norms have impacted modern parenting styles. 8:45 - Finding balance on weekends: How to create space for both personal fulfillment and family connection. 10:14 - Setting boundaries around technology: Modeling healthy phone use and managing screen time for kids. 13:47 - Breaking the comparison trap: The impact of social media on parenting guilt and societal expectations. 16:03 - Multitasking as a modern mother: Navigating the overlap of work, parenting, and personal time. 19:49 - Recharging as a parent and entrepreneur: The value of unstructured “void time” and building it into your life. 25:47 - Reclaiming community: What we can learn from past generations about building support systems. 33:14 - The practice of nervous system regulation: Why calm leadership is a superpower for entrepreneurs. 39:40 - Lessons from experience: Natalie shares how to stay steady under pressure and manage stress effectively as a leader. 48:04 - The concept of “good enough”: Knowing your limits in parenting and business to avoid burnout. 55:38 - The future of AI influencers: Predictions on how AI could shape the creator economy, parenting comparisons, and mental health. 1:05:04 - Protecting mental health in the age of AI and preparing kids for the challenges of an increasingly digital world. 1:09:15 - Introducing the CEO Mama Membership: A supportive space for entrepreneurial moms to find tools, resources, and community for balancing business and motherhood. RESOURCES + LINKS Join the free CEO Mama Newsletter “Unfiltered” here. Fill out the CEO Mama Membership founding member application here. Resources mentioned in this episode: https://www.nytimes.com/2018/12/25/upshot/the-relentlessness-of-modern-parenting.html  https://www.nytimes.com/2023/01/29/upshot/parenting-survey-research.html  https://www.russellsage.org/publications/changing-rhythms-american-family-life-1 https://youtu.be/5nMOfdH7MlA?feature=shared It’s Black Friday at Bossbabe! Join The Société for 50% OFF Now Through Dec 2nd! Lock In The LOWEST RATE To Our Exclusive Membership + Build Your Freedom-Based Business. Get Our Weekly Newsletter & Get Insights From Natalie Every Single Week On All Things Strategy, Motherhood, Business Growth + More.  Learn Natalie’s Proven Method for Building a Profitable, Predictable, Freedom-Based Business and Get Back to WHY you Became an Entrepreneur in this FREE 90-Minute Training. 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)  FOLLOW ceomama: @ceomama Natalie Ellis: @iamnatalie Lindsay Roselle: @lindsayroselle 

Get ready to experience what it feels like to be in The Société membership as you listen to this episode. We’re dropping the recording from this month’s membership Q&A Call where Natalie and Lindsay answer relatable entrepreneurship questions from our members, and provide actionable advice on social media growth, maternity leave planning, hiring and managing your team, and so much more. Some of the questions covered are:  "What’s the balance between posting frequently (on Instagram) and prioritizing meaningful content that aligns with my values?" "I have two team members but no clearly defined roles or job descriptions. How do I create clarity and avoid confusion?" "How do you determine how long cart open periods should be, and what are the advantages of short versus long windows?" Whether you're looking to build a sustainable business, make key pivots, or balance entrepreneurship with motherhood, this episode embraces it all + gives strategies to take your next steps confidently. You’ll also hear about the incredible milestone of Bossbabe hitting $10 million in membership revenue and why Natalie didn’t listen to the advice she was given when she started the membership 7 years ago.  TIMESTAMPS 03:10 – Celebrating $10M in membership revenue: reflections on one year of the revamped Société 07:00 – How to transition your ideal customer and say no to non-aligned clients 09:50 – Starting small: creating job roles and managing priorities for your first hires 15:45 – Social media growth: balancing aesthetics, content volume, and authentic storytelling 25:30 – Planning for maternity leave: cash flow forecasting, dialing back operations, and maintaining profitability 32:40 – Choosing a personal brand vs. business brand: lessons from Natalie and other top entrepreneurs 45:00 – Building predictability in sales for product-based businesses: bundling, seasonality, and subscriptions 54:45 – Freedom in business: why scaling isn’t always the answer and how to align your business with your current season of life RESOURCES + LINKS It’s Black Friday at Bossbabe! Join The Société for 50% OFF Now Through Dec 2nd! Lock In The LOWEST RATE To Our Exclusive Membership + Build Your Freedom-Based Business. Get Our Weekly Newsletter & Get Insights From Natalie Every Single Week On All Things Strategy, Motherhood, Business Growth + More.  Learn Natalie’s Proven Method for Building a Profitable, Predictable, Freedom-Based Business and Get Back to WHY you Became an Entrepreneur in this FREE 90-Minute Training. 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)  FOLLOW bossbabe: @bossbabe.inc Natalie Ellis: @iamnatalie Lindsay Roselle: @lindsayroselle

In this episode, Lindsay introduces the topic of reparenting—a powerful piece of motherhood for ambitious moms to be aware of. Inspired by a conversation between Natalie Ellis and Nakea Homer, Lindsay reflects on how childhood patterns like people-pleasing and overachieving show up in our parenting, relationships, and even our businesses. If you’re feeling like you’re on the verge of burn out or are misaligned doing the juggle of business and motherhood, this episode will help you explore how reparenting your inner child can transform your approach to motherhood and business. Lindsay also shares her personal journey and simple ways to get started with this inner work. What we cover: Nakea’s daughter’s surprising advice on selflessness. How inner child patterns can lead to burnout in business and motherhood. Simple tips for starting your own reparenting practice. TIMESTAMPS 00:44 – The pivotal question Nakea asked her daughter and the surprising answer 01:41 – How ambitious mothers often approach parenting like business goals 02:34 – The wake-up call: Are we self-abandoning in our efforts to “do it all”? 03:03 – What is reparenting, and why it is crucial for ambitious mothers 04:30 – Childhood patterns that impact business and personal relationships 06:08 – Burnout in business: Is it the business—or inner child wounds? 08:46 – Lindsay’s personal story of achieving for validation in childhood 10:42 – How to begin reparenting: Gentle steps to guide your inner child 12:53 – Why this work is foundational to success as an ambitious mama 16:26 – Closing thoughts: Inner work transforms every layer of your life 17:17 – CEO Mama Membership announcement RESOURCES + LINKS Fill out the CEO Mama Membership founding member application here. Listen to the full episode with Nakeia Homer here. Black Friday at Bossbabe is coming! Join the Waitlist Here to be the First to Know What Our Secret Offer is.  Learn Natalie’s Proven Method for Building a Profitable, Predictable, Freedom-Based Business and Get Back to WHY you Became an Entrepreneur in this FREE 90-Minute Training. Join The Société: Our Exclusive Membership Where You Can Access All of Natalie’s Keynotes & Unlock The Best Systems + Tools To Help You Build A Freedom-Based Business. Get Our 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)  FOLLOW bossbabe: @bossbabe.inc Natalie Ellis: @iamnatalie

Ever wondered what it’s really like to build a business in your twenties, ride the rollercoaster of entrepreneurship, and come out the other side? In this episode, Natalie sits down with Teachable founder Ankur Nagpal to spill all the tea on the evolution of online education and the booming creator economy. Together, they take a trip down memory lane, sharing the highs and lows of startup life (spoiler: it’s not always pretty). Ankur also dives into the juicy details of navigating market saturation, using AI to shake up course creation, what happens to your identity after a big business exit, and how he really spends his money after the $250M buy out. If you’re obsessed with entrepreneurship, creating impact, or staying ahead of the trends in online learning, this episode is packed with value— plus, you’ll learn what his second venture is, why he couldn’t just “live the travel life” + what he’s doing differently in business this time around.  TIMESTAMPS 00:00 The Journey Begins: From Teachable to New Ventures 03:13 The Evolution of Online Courses and the Creator Economy 05:51 Navigating Identity and Growth in Entrepreneurship 08:53 The Decision to Sell: Reflections on Success and Freedom 11:49 Financial Freedom: The Shift After Selling Teachable 14:53 Building Again: Lessons from the First Venture 17:58 Hiring and Team Dynamics: The Balancing Act 21:00 The Challenges of Industry and Team Management 24:03 Personal Finance for Business Owners: Key Insights 27:09 The Importance of Mindset in Business Ownership 30:12 Maximizing Financial Benefits: Tax Strategies for Entrepreneurs 32:53 The Psychology of Spending: Balancing Wealth and Humility 35:54 The Impact of Upbringing on Mindset 39:08 Understanding Financial Management for Business Owners 43:47 The Importance of Recurring Revenue 46:53 Navigating the Challenges of Building a Fintech Company 49:57 Marketing Strategies and Audience Engagement 52:17 Getting Started with Financial Tools 54:37 Balancing Personal Life and Work 01:06:04 Redefining Success Beyond Money RESOURCES + LINKS Use this link to grab your special offer from Ankur on carry.com  Black Friday at Bossbabe is coming! Join the Waitlist Here to be the First to Know What Our Secret Offer is.  Learn Natalie’s Proven Method for Building a Profitable, Predictable, Freedom-Based Business and Get Back to WHY you Became an Entrepreneur in this FREE 90-Minute Training. Join The Société: Our Exclusive Membership Where You Can Access All of Natalie’s Keynotes & Unlock The Best Systems + Tools To Help You Build A Freedom-Based Business. Get Our 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)  FOLLOW bossbabe: @bossbabe.inc Natalie Ellis: @iamnatalie Ankur Nagpal: @ankurna