466: We Sold a Company for $745M - Here’s the Reality Behind The Scenes: A Raw Conversation with Kass + Mike Lazerow

What if the “dream job” you worked so hard to earn… wasn’t your dream anymore? In this episode, Natalie sits down with Lindsay MacMillan - a former VP at Goldman Sachs who walked away from a prestigious Wall Street career to follow a lifelong dream of becoming a published author. Since leaving Wall Street, Lindsay has signed major book deals with Penguin Random House, taken the TEDx stage four times, and created a multi-faceted creative business aligned with her values. Together, they unpack what it really takes to leave a good job, why the “Plan B” trap keeps so many women stuck, and how to navigate the financial, emotional, and identity shifts that come with choosing the creative path.  This conversation is an honest, vulnerable, and deeply empowering look at what happens when you stop settling for a life that looks good on paper, and start creating one that actually feels good. TIMESTAMPS 00:00 - Why Natalie cut her trip short + the power of honoring your season 01:03 - From Wall Street to writing: How Lindsay made the leap from VP to published author 02:32 - The real reason people are quitting corporate (hint: it’s not burnout) 04:47 - Walking away from a “good on paper” job to follow your dream 06:58 - How Lindsay earned a VP promotion, and still knew it was time to go 09:05 - The simple shift that helped her unlock work-life balance (and still get promoted) 10:32 - Why prioritizing creativity made her better at her corporate job 12:31 - A realistic financial game plan for leaving a high-paying job 17:00 - How to build a portfolio career that funds your creativity and freedom 21:00 - The mindset shift that helped Lindsay stop working like she was still in corporate 23:01 - How to say no to misaligned money (and trust you’ll be okay) 26:17 - Why “pretty good” is the most dangerous place to be 29:21 - What it really looks like to build a creative career on your own terms RESOURCES + LINKS Get Lindsay’s New Novel: Summer On Lilac Island Build Your Freedom-Based Business Operating System™ This Summer At Our First-Ever Freedom High Summer School: A Live Challenge Designed To Help You Grow Your Audience, Make More Sales + Use AI Without Losing Your Voice. Save Your Seat Here. 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).

The golden era of online business is over, and no one’s saying it loud enough.  In this episode, Natalie breaks down the real reason your launches feel quieter, your content isn’t converting like it used to, and what AI is actually doing to the course, coaching, and creator economy. Spoiler: It’s not about doom and gloom - it’s about evolution. You’ll learn why buyers are savvier than ever, what AI can and can’t replace, and how to future-proof your business by building depth, clarity, and trust. Whether you're a coach, consultant, course creator, or service provider, this episode is your roadmap to staying relevant and wildly in demand over the next 5–10 years. If you've felt like you're working harder for half the results, this conversation will make everything click.  TIMESTAMPS 00:00 - The golden era of “easy online business” is over, here’s why 01:24 - Why so many mid-level creators are quietly burning out 03:03 - What AI is actually replacing (and what still matters) 05:48 - The offers that are collapsing and the ones still converting 07:13 - What AI can’t replace and why that’s your edge 10:07 - 5 examples of deep specialization that cut through the noise 14:51 - Why brand trust and transformation are your new currency 17:44 - Funnel vs. ecosystem: what you actually need to build now 22:49 - The 5 systems every future-proof business needs 24:13 - Stop asking how to grow + start asking how to build smarter 28:24 - How to protect your relevance and stay essential RESOURCES + LINKS Get Your FREE Future Proof Guide Here. Build Your Freedom-Based Business Operating System™ This Summer At Our First-Ever Freedom High Summer School: A Live Challenge Designed To Help You Grow Your Audience, Make More Sales + Use AI Without Losing Your Voice. Save Your Seat Here. 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).

The online business landscape is shifting, and fast. What worked even three years ago is now dangerously outdated, and most entrepreneurs haven’t caught up. In this episode, Natalie unpacks five non-obvious shifts that founders must make to survive (and thrive) in a rapidly evolving market. You’ll learn why visibility and volume are no longer enough, how AI is commoditizing surface-level content, and what it really takes to build a business that lasts through 2030 and beyond. This episode is your roadmap to the next era of online business: one built on infrastructure, IP, thought leadership, and CEO-level clarity. If you want to stop surviving and start architecting a business designed for longevity, this is a must-listen. TIMESTAMPS 00:00 - Why the old online business playbook is collapsing (and no one’s talking about it) 01:04 - The rise of the Architect Founder + why clarity beats charisma 02:47 - AI, audience evolution + the death of surface-level offers 04:38 - Why your launches are getting flatter, even if you’re doing everything “right” 05:25 - The new goal: sustainability, structure + long-term trust 06:17 - Shift 1: From growth to infrastructure - what actually makes a business scalable 10:08 - Shift 2: From funnels to brand experiences - how to make your funnel unforgettable 15:17 - Shift 3: From content to thought leadership - what will actually cut through the noise 19:00 - Shift 4: From personal brand to proprietary IP - why visibility isn’t enough 22:36 - Shift 5: From doer to architect - how to build a business that runs without you 28:55 - The founder who thrives in 2030 will be the clearest, not the loudest RESOURCES + LINKS Follow Along On Instagram For More Content Specific To The 2030 Founder: @bossbabe.inc @iamnatalie + Subscribe On YouTube Build Your Freedom-Based Business Operating System™ This Summer At Our First-Ever Freedom High Summer School: A Live Challenge Designed To Help You Grow Your Audience, Make More Sales + Use AI Without Losing Your Voice. Save Your Seat Here. 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 wonder what it would take to build a $100K/month business with one offer - even if you had no audience, no email list, and no brand name? In this episode, Natalie breaks down exactly what she would do if she were starting from scratch today. You’ll learn the strategy to grow from zero to consistent $100K months without chasing trends, overcomplicating your funnel, or trying to go viral. This is the blueprint for building a high-profit, high-impact business by solving one real problem for one ideal client and doing it in a way that scales with clarity and simplicity. Whether your goal is $10K/month or $100K/month, this episode will show you how to start strong, stay focused, and sell with confidence, even if you're building from scratch. TIMESTAMPS 00:00 - If Natalie had to start from scratch - here’s what she’d do 01:30 - The common mistake keeping people stuck at $0-$10K/month 04:40 - Why your income goals need to align with your life 07:03 - The most urgent, high-value problem to solve 10:14 - One person, one problem, one promise = the clarity formula 12:01 - How to price and package a premium offer 16:14 - Natalie’s simple, no-fluff funnel strategy (built backwards) 19:39 - The truth about visibility and what actually brings leads 22:36 - Organic vs paid vs borrowed traffic: how to know where to start 24:42 - Weekly sales rhythm for consistent revenue 28:27 - The mindset shift that changes how you sell 30:25 - 5 questions to ask before scaling 31:44 - Why Natalie uses Kajabi to build her entire business (and how to start your free 30-day trial) RESOURCES + LINKS Get Your FREE 30-Day Trial with Kajabi Right Here. Build Your Freedom-Based Business Operating System™ This Summer At Our First-Ever Freedom High Summer School: A Live Challenge Designed To Help You Simplify, Systemize + Scale. Save Your Seat Here. 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).

If you’ve ever felt like the “best-kept secret” in your industry, this episode will change that. Natalie is joined by Rory Vaden, bestselling author and co-founder of Brand Builders Group, to talk about what it really takes to clarify your personal brand and scale your business around your unique story. You’ll learn Rory’s proven method for finding your true uniqueness, how to become the go-to name in your niche, and why AI makes your humanity more important than ever. This isn’t about going viral, it’s about becoming wealthy and well-known through emotional connection, storytelling, and serving the person you once were. Plus, Rory is giving away his entire audiobook for free and you don’t want to miss it!  TIMESTAMPS 00:00 - The #1 unlock to building a scalable personal brand 02:00 - Why you don’t start with what, you start with who 05:00 - The shortcut to clarifying your personal brand 08:30 - Why copy-paste brands fail (and what to do instead) 13:00 - Rory’s take on being copied + how to stay original 16:00 - How to future-proof your brand in the age of AI 21:00 - Personal branding vs. information: what still matters 24:45 - Why story > data (especially in saturated markets) 30:00 - The storytelling formula that makes you unforgettable 38:00 - The secret to getting invited onto stages and podcasts 43:00 - How to become known for your original frameworks 47:00 - Grab Rory’s full audiobook FREE while it’s live! RESOURCES + LINKS Get A FREE Early Release Of Rory’s Audiobook: Wealthy And Well-Known Here. 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).