Plenty with Kate Northrup

What actually makes an online business work today?

And why are so many entrepreneurs still struggling—even with more tools, AI, content, and strategies than ever before?

In this expansive and deeply honest conversation, Kate sits down with longtime entrepreneur and business educator James Wedmore to unpack the timeless principles behind sustainable online business growth, why most people overspend while under-learning, and what truly creates transformation in both business and life.

James shares the behind-the-scenes reality of spending five years building his business before seeing meaningful traction, the mindset shifts that helped him survive those early years, and why he believes the future belongs to entrepreneurs who understand human psychology, messaging, embodiment, and emotional resilience—not just tactics.

Together, Kate and James explore the dangerous obsession with shortcuts, why most people misunderstand marketing, and the deeper emotional patterns underneath entrepreneurship, money, and self-worth. They also dive into the changing landscape of online education, AI, and digital products—and why transformation-based businesses are far from dead.

James breaks down the core business principles he believes will still work 200 years from now: understanding people deeply, creating real value, learning how to communicate clearly, and building a business from stewardship instead of constant reinvention.

This episode is part business masterclass, part emotional recalibration, and part wake-up call for anyone who wants to create meaningful work without getting lost in the noise of the online industry.

If you’re a coach, creator, entrepreneur, or someone trying to build a business that actually lasts, this conversation will completely change the way you think about marketing, messaging, profit, and personal growth.

“The future belongs to the people who understand transformation—not just information.” — James Wedmore 
“The level of stewardship required for the level of life you want is the work.” — Kate Northrup
🎤 Let’s Dive into the Good Stuff on Plenty 🎤
00:00 The Entrepreneurial Struggle
03:45 The 50% Profit Rule
11:08 Common Money Mistakes
19:58 Building Real Wealth
29:12 Timeless Marketing Principles
35:13 Are Online Courses Dead?
36:34 Transformation vs. Information
52:47 AI & Human Connection
1:21:14 Letting Go of Control
1:43:30 The Power of Replication 

Links and Resources:
Kate's Instagram
The Business Breakthrough Experience
The Digital CEO Dashboard

Connect with James Wedmore:
Website
Instagram 
✨   What If the Breakthrough in Your Business Isn’t More Hustle?

Created by my friend and 7-figure launch mentor, James Wedmore, The Business Breakthrough Experience is a free 3-part live training designed to help entrepreneurs identify the gaps, bottlenecks, and blind spots keeping their business stuck.

Because most people don’t need more information.

They need clarity on what actually moves the needle.

Inside the experience, you’ll explore:
🔹 What’s slowing your business growth
🔹 The mindset + strategy shifts that create momentum
🔹 How to build a more scalable digital business
🔹 What’s actually working right now in online business

This isn’t about doing more.

It’s about finally seeing what needs to change.

👉 Register for The Business Breakthrough Experience and start creating real momentum in your business. ✨

Are online courses actually dead?

Or are most people simply building them in ways that no longer work?

In this solo episode, Kate pulls back the curtain on the behind-the-scenes numbers, strategy, emotional reality, and nervous system dynamics of her latest Relaxed Money launch—which crossed the $2 million mark at a time when many online business owners are panicking about the future of digital education.

But this episode is about far more than launch metrics.

Kate shares the real emotional experience of navigating fear, pressure, uncertainty, and expansion while leading a multi-seven-figure launch in a rapidly changing online landscape. She opens up about the nervous system spiral she experienced when early registration numbers came in lower than expected, and how using the exact tools taught inside Relaxed Money helped her regulate, recalibrate, and ultimately make clearer strategic decisions.

She also walks through the specific shifts that dramatically improved their results, including simplifying messaging, prioritizing human connection over automation, strengthening affiliate partnerships, improving retention, and creating higher-quality experiences for students instead of chasing bigger audience numbers.

Along the way, Kate explores why recurring customers matter more than vanity metrics, why over-delivering free content can actually hurt conversions, and why building a freedom-based business requires structure, boundaries, and enough spaciousness to sustain creativity and service long term.

This episode is part launch debrief, part business masterclass, and part emotional transparency around what it actually takes to build sustainable success online today.

If you’re an entrepreneur, coach, course creator, or anyone trying to create meaningful work in an increasingly automated world, this conversation will completely change the way you think about growth, connection, and freedom.

“The more structure you have in your business, the more freedom you will have in your life.” — Kate Northrup 
🎤 Let’s Dive into the Good Stuff on Plenty 🎤
00:00 Online Courses Are Dead? Kate Says They’re Wrong
00:58 The $2M Relaxed Money Launch Breakdown
02:57 Fear, Nervous System Spirals & Launch Anxiety
07:41 Using Relaxed Money Tools in Real Time
13:52 The Landing Page Shift That Increased Conversions
19:35 Why Human Connection Beat Automation
28:44 Retention, Re-Enrollments & Repeat Customers
40:12 The Power of Affiliate Relationships
49:03 The AI Tool That Made People Cry
1:05:02 The Future of Online Business & Sustainable Growth

Links and Resources:
Kate's Instagram
The Business Breakthrough Experience
The Digital CEO Dashboard

✨   What If the Breakthrough in Your Business Isn’t More Hustle?

Created by my friend and 7-figure launch mentor, James Wedmore, The Business Breakthrough Experience is a free 3-part live training designed to help entrepreneurs identify the gaps, bottlenecks, and blind spots keeping their business stuck.

Because most people don’t need more information.

They need clarity on what actually moves the needle.

Inside the experience, you’ll explore:
🔹 What’s slowing your business growth
🔹 The mindset + strategy shifts that create momentum
🔹 How to build a more scalable digital business
🔹 What’s actually working right now in online business

This isn’t about doing more.

It’s about finally seeing what needs to change.

👉 Register for The Business Breakthrough Experience and start creating real momentum in your business. ✨

What if success isn’t actually freedom?

And what if the business you built to give you more life slowly became the thing consuming it?

In this deeply honest conversation, Kate sits down with entrepreneur, author, and BossBabe founder Natalie Ellis to talk about ambition, motherhood, nervous system healing, identity, and what it really means to build a freedom-based business.

Natalie opens up about the hidden cost of chasing external validation, the pressure of maintaining a personal brand, and the surprising realization that even after “making it,” she still found herself craving permission to feel chosen. She shares how becoming a mother reshaped her relationship with ambition, success, and even her own identity—and why she no longer believes in building a business that demands everything from the person behind it.

Together, Kate and Natalie explore the tension so many ambitious women feel between growth and presence, career and motherhood, expansion and enoughness. They talk about the emotional reality of entrepreneurship, the influence of social media on our desires, and the subtle ways status and validation can quietly become the thing running the show.

Natalie also shares the behind-the-scenes story of stepping away from BossBabe, buying the company back, and rebuilding it in a way that aligned with the actual life she wanted to live. The conversation moves into nervous system regulation, healing from chaos and functional freeze, navigating marriage and partnership while building a company, and learning how to create success without abandoning yourself in the process.

This episode is a powerful reminder that freedom is not just financial. It’s emotional. It’s relational. It’s nervous system deep. And ultimately, it comes from building a life and business that genuinely supports the person you are—not just the image you project to the world.

“A freedom-based business is a lifestyle business that is a vehicle to the lifestyle you want to live.” — Natalie Ellis
🎤 Let’s Dive into the Good Stuff on Plenty 🎤
00:00 Freedom-Based Business + Redefining Success
04:09 The Pressure of Building a Personal Brand
07:30 Realizing Outer Freedom Wasn’t Enough
10:37 Motherhood, Identity Shifts & Partnership
11:53 Women, Ambition & Work-Life Balance
27:52 Growing Up Feeling Different + Chasing Success
36:11 Nervous System Healing + Functional Freeze
40:00 Rebuilding Success from a More Aligned Model
44:42 Relationships, Vulnerability & Emotional Safety
52:00 Final Reflections + Freedom Beyond Money

Links and Resources:
Kate's Instagram
Recalibration Field Guide

Connect with Natalie Ellis:
Boss Babe
Website
Freedom-based Business Book
Facebook
Instagram
Facebook
✨ Ready for Income That Actually Builds Something?

If you're capable, ambitious, and earning well — but your financial life still feels like something you have to hold together — this one's for you.

The free Recalibration Field Guide is a diagnostic companion to the Recalibration Series here on Plenty. It's built to take what you're hearing in the series and locate it precisely in your money ecosystem — so you can see exactly where to go next.

Most people recognize themselves within the first five minutes.

Inside the Field Guide, you'll explore:
🔹 The Four Hidden Money Ecosystem States — Overdrive, Constriction, Diffusion, and Stewarded — and which one your money is actually running in right now
🔹 The Wealth Stewardship Pyramid — the sequence wealth actually builds through, and how to reorient your ambition toward architecture instead of urgency
🔹 The Four-Leaks Diagnostic — where money and energy are escaping your system, not hypothetically, but in your specific income pattern and situation
🔹 The Energetics → Engineering → Expression Map — why surface-level financial fixes haven't worked, and what to do instead
🔹 Deep Reflection Prompts — built around the central question the series raises: Why do I still feel like I'm the one who has to make everything happen, even when things are going well?

This isn't a budgeting tool. It's not a workbook. It's a diagnostic instrument for self-led leaders who are ready to stop being the sole infrastructure of their own financial life — and build something that actually holds.

👉 Download the free Recalibration Field Guide at katenorthrup.com/fieldguide

Because making more money is powerful.

But building the architecture that makes what you earn actually stay, compound, and support your life?

That's the upgrade. ✨

What if an investment could be both financially irrational… and deeply worth it?

In this episode, Mike Watts returns to Plenty for part two of our behind-the-scenes Airbnb series, where we pull back the curtain on the actual numbers behind our Maine short-term rental project.

And yes — technically, we’re currently underwater on it.

But this conversation isn’t just about profit margins or renovation budgets. It’s about the bigger picture of building freedom-based wealth, creating long-term assets, and making financial decisions that align with your values, your family, and the life you actually want to live.

Mike shares exactly what we paid for the property, how much we spent on renovations, what surprised us most during the process, and the lessons we’ve already learned that we’ll absolutely apply differently next time.

This episode is part real estate breakdown, part wealth philosophy, and part honest conversation about what it actually looks like to build something long-term — even when the math doesn’t immediately “make sense.”

Whether you’re curious about investing in real estate, building multiple income streams, or simply thinking differently about money and freedom, this conversation will expand the way you think about wealth.

“It’s impossible to separate financial decisions from emotions.” - Kate Northrup 

“Real estate allows this kind of fun thing where you can create equity, leverage it, and build again.” - Mike Watts
🎤 Let’s Dive into the Good Stuff on Plenty 🎤
00:00 Airbnb renovation sticker shock
02:22 Why we started an Airbnb business
05:59 Real estate investing + Airbnb metrics
11:08 Why money decisions are emotional
14:13 Property analysis + resale potential
21:20 Estimating Airbnb revenue with AirDNA
27:22 Renovation chaos + unexpected repairs
31:00 Full Airbnb financial breakdown
51:11 Airbnb ethics, taxes + community impact
59:52 Final reflections + future plans

Links and Resources:
Kate's Instagram
Mike's Instagram
Katenorthrup.com
AirDNA
BNBCalc
Airbnb listing for our property
Mel Dorman IG
The Real Estate Investor Goddess Handbook
The Big Money Decision Matrix

✨ What If You Trusted Yourself With Money Decisions?

The free Big Money Decision Matrix is the exact framework Kate uses for major financial decisions — from investments to business moves to buying property.

Because second-guessing is expensive.
And hesitation compounds fast.

Inside, you’ll explore:
🔹 How to regulate your body before making money decisions
🔹 The difference between desire and proving something
🔹 How to get clear on the real numbers
🔹 Whether your wealth systems can actually sustain the win

This is body first, bank account second.

And it’s designed to help you become the kind of person who can say:

“I don’t make bad decisions.”

Not from arrogance.
From self-trust.

👉 Download The Big Money Decision Matrix and use it on a decision you’ve been circling. ✨

Related Episode:
How We Launched Our First Airbnb for Tax Savings, Passive Income & Long-Term Wealth (157)

What if the thing keeping you from receiving more money, love, or support isn't strategy — but how safe it feels to open your heart?

And what if worthiness isn't something you earn… but something you decide?

In this episode, I sit down with Suzy Ashworth for a conversation about receiving — money, love, visibility, support — and the courage it takes to stay openhearted in a world that can feel painful at times.

Suzy shares the winding path from creating the world's first online hypnobirthing program to becoming a leader in the conversation around abundance, audacity, and infinite receiving. We move through identity, motherhood, business evolution, relationships, body-based safety, and the vulnerable process of letting ourselves be fully seen.

What stays with me about Suzy is her willingness to speak honestly about both her gifts and her growth edges. This conversation moves from business and money into heartbreak, self-worth, intimacy, race, and parenting — woven through the lifelong work of opening more fully.

We also explore something many women quietly carry: the tension between wanting more and feeling safe enough to receive it. Because receiving isn't only about money. It's about visibility. Pleasure. Support. Love. Being willing to take up space. Being willing to believe you're worthy before external proof arrives.

Suzy shares how she rewired her body to believe in outcomes before they happened — from becoming a bestselling author to building an eight-figure business — and how worthiness became less about waiting to feel ready and more about making a decision.

This conversation is expansive, honest, funny, and tender. There may be something here for anyone who's been holding back from what they truly desire because receiving it feels vulnerable.

“In order to be able to receive infinitely, you have to be willing to go all in.” –Suzy Ashworth
🎤 Let’s Dive into the Good Stuff on Plenty 🎤
00:32 Susie Ashworth: Background & Achievements
01:23 Episode Themes: Vulnerability, Receiving, Love & Money
03:52 Hypnobirthing & Building the Calm Birth School
07:12 Personal Life, Motherhood & Identity Shift
15:42 Audacity, Authenticity & Self-Expression
22:23 Race, Foster Upbringing & Navigating BLM
26:51 Healing Work & Opening the Heart
36:32 Receiving Money, Worthiness & Keeping Wealth
42:14 Quantum Transformation Method: Coaching Framework
47:03 Desires, Love & Future Intentions
51:42 Resources, Call to Action & Closing

Links and Resources:
Unlocking Financial Abundance with Hypnotherapy with Grace Smith (050)
The Calm Birth School 

Connect with Suzy Ashworth:
Website
Podcast
Instagram
Facebook
Infinite Receiving Free Book
Quantum Transformation Method

✨ Ready for Income That Actually Builds Something?

If you're capable, ambitious, and earning well — but your financial life still feels like something you have to hold together — this one's for you.

The free Recalibration Field Guide is a diagnostic companion to the Recalibration Series here on Plenty. It's built to take what you're hearing in the series and locate it precisely in your money ecosystem — so you can see exactly where to go next.

Most people recognize themselves within the first five minutes.

Inside the Field Guide, you'll explore:
🔹 The Four Hidden Money Ecosystem States — Overdrive, Constriction, Diffusion, and Stewarded — and which one your money is actually running in right now
🔹 The Wealth Stewardship Pyramid — the sequence wealth actually builds through, and how to reorient your ambition toward architecture instead of urgency
🔹 The Four-Leaks Diagnostic — where money and energy are escaping your system, not hypothetically, but in your specific income pattern and situation
🔹 The Energetics → Engineering → Expression Map — why surface-level financial fixes haven't worked, and what to do instead
🔹 Deep Reflection Prompts — built around the central question the series raises: Why do I still feel like I'm the one who has to make everything happen, even when things are going well?

This isn't a budgeting tool. It's not a workbook. It's a diagnostic instrument for self-led leaders who are ready to stop being the sole infrastructure of their own financial life — and build something that actually holds.

👉 Download the free Recalibration Field Guide at katenorthrup.com/fieldguide

Because making more money is powerful.

But building the architecture that makes what you earn actually stay, compound, and support your life?

That's the upgrade. ✨