436: I Exited My Company for $250M, Here’s The Mistakes I Won’t Repeat Again with Ankur Nagpal

In this deeply moving episode, Natalie sits down with her friend + Founder of National Angels, Susan Ramirez. National Angels is a non-profit organization dedicated to transforming the foster care experience for children, youth, and families across the United States. Bossbabe has been a supporter of National Angels for years, deeply moved by the organization’s mission and Susan’s dedication to creating change in the lives of our most vulnerable population - children. Ahead of the holidays, Natalie and Susan share stories of hope, resilience, and transformation that will leave you inspired + maybe a bit emotional. Susan shares her journey of leaving corporate America to pursue this calling, how National Angels is rewriting the future for foster children, and the life-changing power of mentorship and community. Whether you're looking for inspiration, ways to give back this season, or a reminder of the impact we can create when we come together, this is an episode you can’t miss. TIMESTAMPS 00:00 – Welcome + Introduction of Susan Ramirez. 00:29 – Why Natalie has been supporting National Angels for years and why this cause is so close to her heart. 01:55 – Susan’s story: From climbing the corporate ladder to discovering her life’s purpose. 03:36 – The devastating realities of foster care and the ripple effects across society. 07:06 – How Susan piloted her first program and transformed one family’s life. 10:05 – Jonathan’s story: From failing grades to football stardom through mentorship. 13:05 – How National Angels grew from a local initiative to a national movement. 15:34 – The business of non-profits: Running National Angels with strategy, leadership, and purpose. 17:34 – Susan’s faith-driven decision to leave corporate America and lead National Angels. 19:34 – Burnout, leadership struggles, and Susan’s transformative soul adventure in Sedona. 24:46 – Reclaiming her purpose and creating healthier boundaries as a leader. 27:19 – Teaching self-efficacy: Susan’s powerful lessons on intentional parenting and mentorship. 29:15 – Balancing the emotional weight of foster care work with hope and resilience.  32:03 – Abel’s story: A marathon, mentorship, and a life-changing surprise. 35:40 – The power of words: How encouragement changed one foster youth’s life forever. 37:10 – How you can get involved: Donate, volunteer, or mentor a child through National Angels. 39:22 – The tangible impact of donations and the ripple effects of supporting this mission. 41:22 – How the Bossbabe community can step up and support National Angels. 42:29 – Volunteer and mentorship opportunities: How you can make a lasting difference. 45:13 – Susan’s advice to her younger self: “Keep going—every hard moment is worth it.” RESOURCES + LINKS Use this link to donate to National Angels + participate in Bossbabe’s Matching Campaign. Learn more about the National Angels Non-Profit + learn how to volunteer in your area. Learn more about Austin Angels, the Founding Chapter of National Angels Documentaries mentioned in the episode: Transforming Foster Care + Abel’s Surprise at the Finish Line 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 National Angels: @nationalangels Austin Angels: @austinangelsnonprofit Susan Ramirez: @mrs.susanramirez

In this long-overdue and first-ever public conversation, Natalie sits down with Alex Wolf, the original creator of Bossbabe, to unpack the untold story of the brand that changed everything. For the first time, they share the raw truth behind the creation of Bossbabe, its explosive rise, and how a simple idea became a global movement that inspired millions of women. Together, they reveal what it took to build this iconic brand, the challenges they faced along the way, and why Alex decided to step away from the spotlight while Natalie scaled the business. This episode is packed with candid confessions, deep reflections, and insights into what really happened behind the scenes. If you think you know the story of Bossbabe, think again. This is the episode you didn’t know you were waiting for.  TIMESTAMPS 00:00 Introduction: The first conversation in seven years—why it took so long 00:43 The Bossbabe Origin Story: From dropout to visionary—how Alex turned an idea into a movement 03:13 The Birth of Bossbabe: The moment Alex realized “Bossbabe” was the next big thing 07:06 Making Money at 22: Babysitting, coding, and building digital subscriptions before it was trendy 11:32 Passing the Baton: How Natalie stepped in as CEO and took the brand global 18:23 The Acquisition Drama: Clearing the air on rumors and the truth behind Natalie taking ownership 25:19 Identity Crisis: The emotional toll of early success and stepping away from the spotlight 29:33 Cultural Impact: How Bossbabe sparked a global movement for ambitious women 41:34 Predictions for the Future: What’s next for branding, tech, and social media 54:35 Avoiding Burnout: Why selling views is a trap and building a brand is the ultimate strategy 01:01:46 Healing and Transformation: Turning pain into power—how Bossbabe became a lifeline for so many 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 Wolf: @alexwolf

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

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