the bossbabe podcast

This is the conversation about the part most founders don't say out loud: the moment you hit the revenue number and feel nothing.

Natalie sits down with Jenna Wright — a Pilates studio owner who built a 7-figure business from $1,000 and an air mattress. From the outside, she'd made it. From the inside, she was running at 9% profit, paying herself $80K a year, and calling it — in her own words — a pretty prison. So she did what most founders won't: she dismantled it on purpose. They go inside the math (she was running $1.2M at 9% profit, paying herself $80K/year), the team mutiny that finally broke the model, and the deliberate revenue cut from $1.2M to $650K that tripled her margin to 30%.

If you've ever hit the revenue numbers and felt nothing, this episode is the operating system for what comes next.

Time Stamps:

07:40 "Tired at a soul level" — the burnout most founders hide

10:00 $1,000 and an air mattress: the rebuild from zero

14:05 $250K to $875K in one year (and the cost it hid)

19:10 The misery beneath success

25:15 The team mutiny that broke the business model

28:33 The math: cutting 4 studios to 2, profit triples

31:50 "Your business will expose every wound you have"

33:00 The 7-day retreat that reorganized everything 

40:05 The lessons Jenna is rewriting today

Resources + Links:

Pre-Order The Freedom-Based Business Method.

Follow Jenna: @iam_jennawright

Learn more about Jenna's Teacher Training

Follow Jenna Wright + Read Her Substack "The Shift" Where She Documents The Scale-Down Publicly

Sign Up For Our Free 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).

In this episode, Natalie sits down with Keren Eldad — coach to some of the world's highest achievers and author of Gilded and the new Gilt Free — to unpack why external success never delivers the safety it promises. Keren shares the three core wounds beneath achievement addiction, the "gilded cage" so many high-achieving women are trapped in, and the surprising income threshold where what you want out of life finally starts to change.

You'll learn how to recognize the wound driving your hustle, why "assume everyone likes you" became her most viral piece of advice, and the riptide rule for holding onto success without letting it consume you.

If you've ever achieved everything you set out to and quietly wondered why it's still not enough, this episode is the reframe and the way out.

Time Stamps: 

03:50 The gilded cage: when the shiny life is the trap

07:50 "Yes, we're addicts" — achievement as addiction

15:30 The 3 core wounds behind every overachiever

18:18 The success coach who still spirals when business slows

21:34 The $500K line that changes what you actually want

27:50 "Assume everyone likes you" — the rule that went viral

38:11 The riptide rule for holding onto success

48:28 Why scaling might be the wrong goal entirely

53:46 What real credibility in coaching actually looks like

Links & Resources: 

Pre-Order The Freedom-Based Business Method.

Follow Keren: @coachkeren 

Grab a copy of Keren’s book - Gilded: Breaking Free from the Cage of Ambition, Perfectionism, and the Relentless Pursuit of More

Listen to Natalie on COACHED by Keren Eldad

Sign Up For Our Free 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).

Most course creators add more channels to scale. Anna Konchar did the opposite and now runs a 7-figure business on 2 days a week.

Natalie sits down with Anna Konchar — the funnel strategist behind a 7-figure evergreen course business that runs on 2 days a week while she's home with her three kids. Anna shares the exact mechanics of the evergreen funnel + paid ads engine she's used for eight years, why she cut her podcast and YouTube last year to focus on ONE offer, and how she rebuilt after her payment processor shut down her account overnight. Expect specific numbers, uncomfortable honesty about AI in funnels, and a framework you can test against your own course business this quarter.

If you've ever wondered how a course creator can scale to seven figures without launching live, this episode is the operating system.

Time Stamps:

03:11 From laid-off to full-time entrepreneur in 30 minutes

07:33 The funnel that sells while she sleeps

16:55 When the offer stops converting, fix THIS first

21:30 The pricing test most course creators never run

24:00 The webinar mistake 99% of course creators make

32:13 The day her recurring revenue disappeared overnight

39:10 How a 7-figure founder preps for maternity leave

Resources + Links

Annakonchar.com/bossbabe

Find Anna on IG: https://www.instagram.com/annakonchar/

Pre-Order The Freedom-Based Business Method.

Sign Up For Our Free 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).

Ever wondered why every time you reach a new revenue level, the same exhaustion shows up — just dressed differently?

In this conversation, Natalie sits down with Julie Santiago — founder of We Are The Women, former Wall Street operator, and one of the rare guests who can break down what high-functioning burnout actually looks like at the 7- and 8-figure mark. Julie walks through the three burnouts that shaped her career: the Wall Street year that put tumors on her ovary at 28, the coaching practice she rebuilt in a San Francisco apartment, and the post-motherhood collapse that brought her to her knees again. The takeaway isn't grit. It isn't quitting. It's something Julie calls evolution and it's the framework most high-achieving women never get taught.

This isn't about hustle, balance, or finding your why. It's a brutally honest breakdown of what high-functioning burnout actually looks like at the 7- and 8-figure mark, why the same pattern that builds your success eventually breaks you, and how to evolve past the cycle so you stop ending up in the same place at every new level.

Time Stamps:

00:59 The childhood imprint that built an 8-figure business and broke it

05:45 Wall Street, tumors at 28, and the body's verdict

13:10 The 2-path trap: why pushing through OR quitting both fail

20:45 Why clunkiness is a season change, not a failure to optimize

28:40 The match-my-salary moment her therapist shut down

33:22 Safety, surrender, and a new relationship to money

38:18 The metaphor that broke her thinking about money's source

43:30 Going all-in vs. knowing when to evolve

Resources + Links:

Pre-Order The Freedom-Based Business Method.

Follow Julie on Instagram

Learn more about We Are the Women

Sign Up For Our Free 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).

Organic content builds your brand. But ads? Ads build your bank.

In this episode, Natalie sits down with Brooke Shelton — a former Meta insider who helped train the platform's ad AI and advised advertisers spending hundreds of millions of dollars on Meta. Brooke delivers a full tactical masterclass on running Meta ads with AI: the strategy most founders get wrong, how to build AI agents that create and manage your campaigns, and why the next 9 to 12 months are a rare window to master this before Meta automates it all away.

You'll learn the one-campaign, one-ad-set rule that stops you competing against yourself in the ad auction, why creative (not audience targeting) is your only real advantage in 2026, and how Brooke runs her entire business on AI with zero team after 6X-ing her revenue. She also breaks down the difference between an assistant, an agent, and agentic AI, then gives a step-by-step walkthrough for building your very first AI agent today.

If you've ever felt like ads are too technical, too expensive, or too overwhelming to touch, this episode is the reframe — and the operating system behind it.

And if this conversation lights you up, Natalie and Brooke are taking it live and hands-on at their AI hackathon in New York City on June 10th. All the details are linked below.

Time Stamps:

00:00 - From Meta's ads AI team to building her own business

06:30 - Why organic builds brand, but ads build bank

09:49 - The 9-month AI window before Meta does it all for you

14:27 - The one-campaign, one-ad-set rule most founders get wrong

18:14 - How to let AI run your entire ad account

21:58 - Why creative is your only real bid in 2026

26:11 - Can AI really build hundreds of ads? The 10/80/10 reality

29:32 - Assistant vs agent vs agentic AI, finally explained

34:19 - The full AI tool stack behind a zero-team business

41:53 - How to build your first AI agent today

46:53 - Inside the June hackathon with Natalie + Brooke

Resources + Links:

Join Natalie + Brooke At The Freedom AI Hackathon In NYC On June 10th: Spend One Day Building Your Entire AI-Powered Sales + Marketing Engine, Done With You In The Room

Get Inside Brooke's AI Ads Coaching Membership At Atelier AI

Natalie + Jamie Kern Lima At GodMothers: An Evening Of Connection, Wisdom + Community For Ambitious Women

Join The Earn Your Happy Live Podcast Taping With Lori Harder: Be In The Room For A Live Recording With Natalie + Lori Harder (plus a Q&A session with Powerhouse Female Entrepreneurs)

Pre-Order The Freedom-Based Business Method.