the bossbabe podcast

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

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

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

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

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