437: CEO Mama: Healing Generational Patterns, Reparenting + How Our Kids Impact Our Inner Work

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

In this inevitably relatable episode, Lindsay dives deep into the concept of the mental load that mothers carry, especially entrepreneurial + working moms. She discusses the importance of recognizing each piece of the mental load that mothers carry and teaches on how to lighten this load, which is essential to preventing burnout. Lindsay introduces her framework of the "seven buckets" that encompass various aspects of a mother’s life, offering practical strategies to manage and share responsibilities effectively. TIMESTAMPS 00:00 Introduction to Lightening the Mental Load 01:55 Understanding the Mental Load of Motherhood 08:35 The Seven Buckets of Mental Load 14:29 Evaluating Capacity vs. Load 18:44 Tools for Lightening the Load 28:11 Taking Action to Lighten the Load 35:31 Conclusion and Reflection on Motherhood The Seven Buckets Outlined: Work Money Fun Health Love/Relationships  Kids/Parenting Purpose/Meaning RESOURCES + LINKS Fill out the CEO Mama Membership founding member application 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 Lindsay Roselle: @lindsayroselle

In this episode, Natalie Ellis sits down with psychotherapist and digital health strategist Israa Nasir to tackle the trending issue of toxic productivity. They explore how high-achieving entrepreneurs can break free from the addiction of “doing more” and redefine success to match their balancing point. Whether you’re constantly chasing the next goal, feeling chronically behind, or struggling to balance your personal life and business, this episode offers practical steps to help you prioritize mental health and find your “enough” point. TIMESTAMPS 04:24 Navigating the Mental Health System 07:10 The Illusion of an Optimized Life 15:40 Breaking Free from Societal Timelines 21:30 The Paradox of Achievement and Fulfillment 27:40 Finding Balance as an Entrepreneur 30:05 Intentional Living and Life Audits 31:40 The Importance of Unplugging and Self-Care 41:45 Overcoming Over-Functioning and Toxic Productivity 47:30 Creating Healthy Routines for Balance RESOURCES + LINKS 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)  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. Get Our Weekly Newsletter & Get Insights From Natalie Every Single Week On All Things Strategy, Motherhood, Business Growth + More.  Join The Société: Our Exclusive Membership To Help You Build A Freedom-Based Business. FOLLOW bossbabe: @bossbabe.inc Natalie Ellis: @iamnatalie Israa Nasir: @well.guide

In this episode of CEO Mama, Lindsay dives deep into the complexities of childcare, discussing its challenges, costs, and the various opinions surrounding it. She shares what she’s found to be the most important aspects when it comes to finding the right childcare for your family. The conversation also touches on handling disruptions in arrangements and the significance of alone time for mental health. We also reached out to our amazing CEO Mamas and asked how they navigate this as mothers and entrepreneurs. Tune in for an insightful episode that will not only offer you guidance but also leave you feeling less alone when trying to find the best solution for you and your family.  TIMESTAMPS 00:20 - The Childcare Conundrum 03:00 - Best Practices for Finding Childcare 10:30 - Onboarding and Setting Expectations 14:00 - Handling Disruptions and Inconsistencies 20:30 - Personal Childcare Arrangements and Insights 31:00 - Reflections on Childcare From Our CEO Mamas 31:55 - Anna Powers: Founder of Clickworthy Copywriting Certification (mom of 1 toddler with full-time childcare) 37:45 - Megan Van Noy - Myofunctional Therapist: (single mom to 1 toddler with part-time daycare + grandparents help) 40:35 - Anna Konchar - Digital Ads Expert + Coach (3 kids 5 years + under with past nanny experience + part-time preschool currently) 48:05 - Lacey Sites - Business Coach (1 toddler with full-time nanny support) RESOURCES + LINKS Join The Société: Our Exclusive Membership 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)  Fill out the CEO Mama application here: bossbabe.com/ceomama FOLLOW bossbabe: @bossbabe.inc Natalie Ellis: @iamnatalie Anna Powers Website Anna Konchar Website Megan Van Noy Instagram Lacey Sites Website

In this conversation, Nakeia Homer joins Natalie to explore the profound connections between personal healing and entrepreneurship. They discuss the impact of childhood experiences on adult life, the importance of intuition in career choices, and the journey of self-discovery. From healing relationships to the dynamics of reparenting + parenting, Nakeia and Natalie cover it all. Tune in for an empowering + uplifting conversation.  TIMESTAMPS 03:30 - The Healing Journey of Entrepreneurship 09:00 - Defining Moments and Career Aspirations 16:30 - Identity and Self-Discovery 22:45 - Overcoming Fear and Limiting Beliefs 29:30 - Lowering Expectations for Acceptance 35:00 - Reparenting and Parenting Dynamics 44:00 - Setting Boundaries in Relationships 55:22 - Navigating Fear and Embracing Possibility RESOURCES + LINKS Join The Société: Our Exclusive Membership 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 Nakeia Homer: @nakeiahomer