Natalie built a wildly recognizable beauty brand, raised $13 million, got it into major retail, and still came away with the same uncomfortable realization a lot of founders quietly have: the number in the headline and the money you actually feel are not the same thing.

This isn’t a Cinderella story. It’s what happens when a smart founder tells the truth about money, control, and what an exit actually feels like after the applause stops.

01:09 Meet Natalie Mackey

02:44 The Pivot That Changed Everything

05:15 Why Beauty Breaks E-Commerce Rules

07:25 The Product That Took Off Overnight

08:09 Fundraising Is Timing, Not Talent

13:06 The Decision to Sell Instead

18:22 The Truth About “Winning” an Exit

19:07 Why the Second Time Feels Different

20:38 AI Is Giving New Founders an Edge

21:30 Losing the “Founder” Identity

24:45 The Pressure to Do It Again

26:33 Why You Just Have to Start

28:00 Money, Risk, and Never Feeling Safe

30:18 The Traits That Actually Matter

In this episode of The Exit Whisperer, Carrie sits down with Andrea Johnston, founder of Pure Communications, to unpack what most founders never say out loud: sometimes the business is thriving, the numbers are strong, the offers are real, and you still know it’s time to sell.

They get into building with intention, why niche agencies scale faster than scattered ones, what private equity actually wants, and how to know whether you’re growing a business… or just feeding a machine that no longer fits your life. Andrea also opens up about what she would do differently, why succession planning matters more than founders think, and the hard truth that reacting emotionally will cost you more than almost any bad strategy.

00:54 Meet Andrea Johnston

02:48 Why She Left Corporate to Start Her Agency

04:51 The Gap Between “Starting” and Building a Real Business

05:23 How She Scaled Using Only Her Network

07:27 The Decision to Niche Down

10:31 The Real Growth Engine: Existing Clients

12:15 How Private Equity Entered the Picture

17:38 Inside the Sale Process

18:14 What Actually Changes After You Sell

19:28 How Acquisitions Create Opportunities for Your Team

20:15 The Second Exit: Moving Fast in Private Equity

21:35 Burnout at the Top

25:22 Taking 2 Years Off

28:41 Building “Fuel for Female Founders”

32:24 Final Lessons on Exits, Growth, and Letting Go

In this episode of The Exit Whisperer, Carrie sits down with Lana Powers (founder of Powers PR) to unpack a truth most founders ignore until it’s too late: success can still be the wrong path if it’s killing you to sustain it.

They get into rebuilding a company just to make it sellable, why hitting a peak can be more dangerous than failing, and how founders confuse “being needed” with “being healthy.” Lana also opens up about the aftermath of selling, the second-guessing, the “what if I kept going,” and redefining success beyond revenue, status, or control.

00:56 Meet Lana Powers

02:57 Hitting Rock Bottom As A Founder

03:57 Starting Powers PR From Scratch

05:17 Growing Slowly Into Real Momentum

06:15 Scaling While Pregnant With Twins

10:53 The Reality Of Running A PR Agency

14:58 Burnout In The Wellness Industry

15:54 Rebuilding The Business The Right Way

17:10 The Client That Changed Everything

18:50 Learning To Detach As A Leader

19:37 When Your Body Starts Breaking Down

22:35 How She Chose The Right Buyer

23:58 Life After Selling The Business

27:00 What Success Looks Like Now

In this episode of The Exit Whisperer, Carrie sits down with Caren Sinclair — a serial founder, operator, and dealmaker who has sold multiple businesses and is honest enough to say the quiet part out loud.

Caren breaks down what founders rarely admit in public, how early investor pressure can push you into deals you wouldn’t choose in a stronger position, why equity-only exits often sound better than they feel, and how financial stress doesn’t just hurt your business… it distorts your judgment. They also get into choosing the right co-founder, raising from the right people, and why safety (not comfort) is the real prerequisite for smart entrepreneurship.

03:31 The Moment She Walked Away From Safety

06:01 Why Most Founders Make Bad Bets

07:54 The 2-Year Exit That Wasn’t What It Seemed

16:05 The Truth About “No Cash” Exits

20:43 Starting Again After Selling Too Soon

24:01 Why Salary Can Save Your Startup

24:36 The Partnership That Changed Everything

26:08 Raising Money Without Losing Control

26:55 Why Big Funding Can Kill Discipline

29:10 When Competition Turns Into Survival

32:24 The Lesson Most Founders Learn Too Late

33:41 How To Actually Pick A Co-Founder

36:08 The Mindset That Makes You Unbreakable

Rachel Sklar built the most powerful women-in-tech network before “women’s communities” were trendy. In this episode of The Exit Whisperer, Carrie Kerpen sits down with Rachel, founder of The Li.st, to unpack the kind of exit founders never brag about — because it’s not a flashy SaaS story.

They get into the messy parts people skip: charging for community (hello, “pay to be her friend” headlines), why “perfect-fit” acquisitions die when you wait too long, what happens when the buyer’s lawyer kills the vibe, and why sometimes the smartest deal is the one that lets you sleep at night — even if it’s not the biggest number.

02:25 Meet Rachel Sklar: The Original Community Builder

03:05 Building The Li.st Before “Women’s Networks” Were Cool

06:09 Protecting Trust While Scaling

09:34 The Controversy

23:10 The Lessons Nobody Tells You

32:23 The “Perfect CEO” Idea (And The Plot Twist)

32:41 Startup Institute33:01 What The Li.st Could’ve Become

35:12 Pregnancy Changes The Timeline

36:30 COVID-19 Proves The Li.st’s Real Value

37:46 Handing Over The House You Built

52:30 Rachel’s Next Chapter After The Exit

58:54 What She’d Do Differently Now

Kristine Tokonow bootstrapped her way into major retailers and global brands, survived COVID, supply chain chaos, labor shortages, pregnancy, and a year that pushed her to the edge. She knew she was burned out in 2021 — but she didn’t sell then. Instead, she rebuilt, stabilized, and intentionally positioned the company to be worth walking away from.

In this episode of The Exit Whisperer, Carrie sits down with Kristine, founder of The Conery, just days after selling the company she spent 12 years building from scratch. What started as a simple question — why are ice cream cones still terrible? — turned into a bootstrapped manufacturing business supplying major brands, theme parks, and retailers.

00:50 Meet Kristine Tokonow

01:17 The Idea That Didn’t Exist Yet

02:19 From Side Hustle to Real Business

04:03 Scaling, Scrappiness, and Early Growing Pains

10:19 When COVID Hit the Business

11:21 Burnout, Pregnancy, and Pressure

13:30 Knowing It Was Time to Sell

14:15 Rebuilding Energy Before an Exit

15:27 Why 2021 Nearly Broke Everything

16:53 The Advisor Who Changed the Outcome

18:57 The Emotional Reality of Selling

20:04 The Day After It Was No Longer Hers

21:39 Letting Go and Walking Away

23:16 What Comes After the Exit

Selling your company isn’t always a flex. Sometimes the bravest exit is walking away. If you’re “fine” but your body is screaming, this episode is for you. In this episode of The Exit Whisperer, Carrie sits down with Roslyn McLarty, co-founder of The GIST, who left a fast-growing, funded company when burnout stopped being a vibe and started being a warning sign.

We get into the unsexy truth founders don’t post: the eye twitch, the dread, the “take a long weekend” advice that solves nothing, and the moment you realize it’s not just hard — it’s misaligned. Roslyn breaks down what burnout actually is (a chronically activated nervous system), how to tell “push through” from “get out,” and why chasing outcomes (revenue, valuation, the headline) is the fastest route to losing yourself.

02:19 Meet Roslyn McLarty

04:18 Building The GIST From Scratch

05:08 Why Fundraising Was an Uphill Battle

07:24 Role Misalignment: The Silent Burnout Trigger

12:41 Hitting Burnout — And Finally Stopping

19:56 The Inner Critic That Won’t Shut Up

20:16 How Burnout Warps Business Decisions

21:22 The Emotional Whiplash of Leaving Your Company

22:19 Processing Grief, Relief, and Identity Loss

24:25 Finding Alignment After the Exit

26:16 Rebuilding Without Burning Out Again

29:50 How to Recognize and Regulate Burnout

33:44 What Every Founder Needs to Hear

Meghan built exactly the kind of business founders are told to want: flexible, profitable, and “lifestyle-friendly.” Then her 10-year-old assumed she’d be working at hockey practice — and she realized the business had quietly taken more than it ever gave back.

In this episode of The Exit Whisperer, Carrie sits down with Meghan Block, founder of Wicked Good Mom Media to unpack how a single local domain turned into a multi-market media company — and why scaling it further would’ve required giving up the one thing she wasn’t willing to lose: presence with her kids.

01:31 Meet Meghan Block: From Domain To Media Company

03:06 Building Wicked Good Mom Media

05:45 Scaling A Hyperlocal Business

10:06 The “Summer Of Mama” Reset

12:08 The Moment She Decided To Sell

12:59 Getting The Business Exit-Ready

15:01 Why Private Equity Wasn’t The Answer

15:27 Defining The Right Buyer

16:03 Protecting Financial Security After The Sale

16:17 Why She Refused A Long-Term Earnout

16:57 Finding The Buyer By Accident

18:15 When Family Becomes The Real KPI

21:35 The Boundary That Changed Everything

27:35 What’s Next After The Exit

Most acquisitions fail because founders obsess over the price — not the people. Monica Kocher built and exited two companies by doing the opposite. In this episode, Carrie sits down with Monica, a rare founder who bootstrapped and sold twice — once through a strategic partnership that became an acquisition, and once through an advisory relationship that turned into a buyer.

This is a masterclass in what most founders get wrong: thinking exits are transactions, not long-term relationships. Monica breaks down why partnering before you sell can be the difference between a smooth exit and a cultural disaster, and why letting a potential acquirer see your company up close is not weakness, it’s leverage.

01:00 Meet Monica Kocher

02:15 First Exit: Building And Selling Gugu Chew

04:08 How The Acquisition Came Together

07:15 Looking Back On The Gugu Chew Exit

08:56 Second Company: The Smart Gift Idea

11:04 Partnering With 1-800-FLOWERS

13:16 Why Advisory Boards Matter More Than You Think

13:57 Aligning Vision With Advisors Early

14:47 How COVID Changed Corporate Gifting Forever

15:15 Scaling Fast Without Losing Control

16:08 Inside The Acquisition Process

16:44 When Advisors Become Acquirers

20:34 Advice For Women Building Toward An Exit

23:43 Final Takeaways + How To Find Monica

In this episode of The Exit Whisperer, Carrie sits down with Amanda Goetz, founder of House of Wise and author of Toxic Grit, to unpack one of the most dangerous deal structures founders don’t talk about: the equity sale with no cash.

Amanda shares the full, unfiltered story of selling her fast-growing brand in an equity deal that looked “perfect” on paper — and how it quietly turned into a nightmare. We get into the emotional state founders are in when they sell, the paperwork everyone assumes gets handled, and the brutal reality of what happens when it doesn’t.

00:47 Meet Amanda Goetz

02:13 The Rise Of House Of Wise

02:42 Challenges In Fundraising

04:30 The Equity Deal (No Cash, High Risk)

04:43 When The Deal Started To Go Wrong

07:15 The Personal And Financial Fallout

10:28 Lessons Learned And Hard Advice

12:46 Decisions Made Under Pressure

13:39 Letting Go: Identity, Trauma, And Loss

14:38 When New Management Took Over

15:57 Starting Over: 2025 And Beyond

16:19 Finding New Roles And Creative Energy

16:57 From Newsletter To Book Deal

20:25 What “Toxic Grit” Really Means

23:17 The 10 Characters That Shape A Life