The Exit Whisperer

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 Johnston02:48 Why She Left Corporate to Start Her Agency04:51 The Gap Between “Starting” and Building a Real Business05:23 How She Scaled Using Only Her Network07:27 The Decision to Niche Down 10:31 The Real Growth Engine: Existing Clients12:15 How Private Equity Entered the Picture17:38 Inside the Sale Process18:14 What Actually Changes After You Sell19:28 How Acquisitions Create Opportunities for Your Team20:15 The Second Exit: Moving Fast in Private Equity21:35 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 Powers02:57 Hitting Rock Bottom As A Founder03:57 Starting Powers PR From Scratch05:17 Growing Slowly Into Real Momentum06:15 Scaling While Pregnant With Twins10:53 The Reality Of Running A PR Agency14:58 Burnout In The Wellness Industry15:54 Rebuilding The Business The Right Way17:10 The Client That Changed Everything18:50 Learning To Detach As A Leader19:37 When Your Body Starts Breaking Down22:35 How She Chose The Right Buyer23:58 Life After Selling The Business27:00 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 Safety06:01 Why Most Founders Make Bad Bets07:54 The 2-Year Exit That Wasn’t What It Seemed16:05 The Truth About “No Cash” Exits20:43 Starting Again After Selling Too Soon24:01 Why Salary Can Save Your Startup24:36 The Partnership That Changed Everything26:08 Raising Money Without Losing Control26:55 Why Big Funding Can Kill Discipline29:10 When Competition Turns Into Survival32:24 The Lesson Most Founders Learn Too Late33:41 How To Actually Pick A Co-Founder36:08 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 Builder03:05 Building The Li.st Before “Women’s Networks” Were Cool06:09 Protecting Trust While Scaling09:34 The Controversy23:10 The Lessons Nobody Tells You32:23 The “Perfect CEO” Idea (And The Plot Twist)32:41 Startup Institute33:01 What The Li.st Could’ve Become35:12 Pregnancy Changes The Timeline36:30 COVID-19 Proves The Li.st’s Real Value37:46 Handing Over The House You Built52:30 Rachel’s Next Chapter After The Exit58:54 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 Tokonow01:17 The Idea That Didn’t Exist Yet02:19 From Side Hustle to Real Business04:03 Scaling, Scrappiness, and Early Growing Pains10:19 When COVID Hit the Business11:21 Burnout, Pregnancy, and Pressure13:30 Knowing It Was Time to Sell14:15 Rebuilding Energy Before an Exit15:27 Why 2021 Nearly Broke Everything16:53 The Advisor Who Changed the Outcome18:57 The Emotional Reality of Selling20:04 The Day After It Was No Longer Hers21:39 Letting Go and Walking Away23:16 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 McLarty04:18 Building The GIST From Scratch05:08 Why Fundraising Was an Uphill Battle07:24 Role Misalignment: The Silent Burnout Trigger12:41 Hitting Burnout — And Finally Stopping19:56 The Inner Critic That Won’t Shut Up20:16 How Burnout Warps Business Decisions21:22 The Emotional Whiplash of Leaving Your Company22:19 Processing Grief, Relief, and Identity Loss24:25 Finding Alignment After the Exit26:16 Rebuilding Without Burning Out Again29:50 How to Recognize and Regulate Burnout33:44 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 Company03:06 Building Wicked Good Mom Media05:45 Scaling A Hyperlocal Business10:06 The “Summer Of Mama” Reset12:08 The Moment She Decided To Sell12:59 Getting The Business Exit-Ready15:01 Why Private Equity Wasn’t The Answer15:27 Defining The Right Buyer 16:03 Protecting Financial Security After The Sale16:17 Why She Refused A Long-Term Earnout16:57 Finding The Buyer By Accident18:15 When Family Becomes The Real KPI21:35 The Boundary That Changed Everything27:35 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 Kocher02:15 First Exit: Building And Selling Gugu Chew04:08 How The Acquisition Came Together07:15 Looking Back On The Gugu Chew Exit08:56 Second Company: The Smart Gift Idea11:04 Partnering With 1-800-FLOWERS13:16 Why Advisory Boards Matter More Than You Think13:57 Aligning Vision With Advisors Early14:47 How COVID Changed Corporate Gifting Forever15:15 Scaling Fast Without Losing Control16:08 Inside The Acquisition Process16:44 When Advisors Become Acquirers20:34 Advice For Women Building Toward An Exit23:43 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 Goetz02:13 The Rise Of House Of Wise02:42 Challenges In Fundraising04:30 The Equity Deal (No Cash, High Risk)04:43 When The Deal Started To Go Wrong07:15 The Personal And Financial Fallout10:28 Lessons Learned And Hard Advice12:46 Decisions Made Under Pressure13:39 Letting Go: Identity, Trauma, And Loss14:38 When New Management Took Over15:57 Starting Over: 2025 And Beyond16:19 Finding New Roles And Creative Energy16:57 From Newsletter To Book Deal20:25 What “Toxic Grit” Really Means23:17 The 10 Characters That Shape A Life

Your “dream exit” is probably a math problem you haven’t done yet. Gigi Lee Chang built Plum Organics to a reported nine-figure exit to Campbell Soup Company — then tells the part founders don’t talk about: dilution, losing control, and why the headline is rarely what hits your bank account.In this episode, Carrie Kerpen sits down with Gigi Lee Chang to unpack the real trade: raising money to go faster… and watching the cap table quietly decide what you “walk away with.” We talk about the pouch pivot that changed the category, the behind-the-scenes reality of board power, and the uncomfortable truth that “entrepreneur” became a status badge — not a job description.02:52 Meet Gigi Lee Chang04:17 The Idea Behind Plum Organics07:26 Early Challenges Building The Brand10:39 The Pouch That Changed The Category22:07 The Shift To Plum As The Core Brand22:55 Looking Back On The Decision25:01 When Gigi Lost Control Of The Company25:48 How Investors Actually Think28:15 Selling Plum Organics To Campbell’s29:20 Life After The Acquisition30:32 Entrepreneur Vs Small Business Owner41:18 What Gigi Is Building Now

The first offer was three times too low — and Stacy Stahl almost walked away. Instead, she did something most founders never do, and it changed the entire deal. In this episode, Carrie sits down with Stacy Stahl (founder of How He Asked — yes, the “Gossip Girl of proposals” — acquired by The Knot) to break down the part founders don’t post: the lowball, the power move, and the moment you realize your business is only worth what you’re willing to sell it for.01:09 Meet Stacy Stahl02:37 The Idea That Started How He Asked03:34 Going Viral Before “Going Viral” Was A Thing05:32 How The Knot Came Into The Picture09:38 The Lowball Offer, The Counter, And The Power Shift16:04 Why She Started Her Second Company Anyway20:06 When The Easy Path Disappears20:45 Jumping From Digital To Product — On Purpose22:57 Building A Business During COVID23:49 The Pivot That Changed Everything24:57 Breaking Into The Promotional Products World26:59 Running A Business Without Burning Out29:31 Why Simple, Profitable Businesses Win32:01 Building Success And Bringing Others With Her

Kendra Bracken Ferguson built companies that invented the creator economy before Instagram and TikTok — and she tells the part founders unusually hide: when the shiny acquisition stops working, the earn-out math gets ugly, and you have to choose between protecting your title or protecting your team…We get into trust as a system (including her very controversial co-founder test), buying a company back, building BrainTrust into a studio + fund backing Black beauty & wellness founders, and why corporate partners suddenly got nervous about “Black founder” the second it became inconvenient.01:36 Meet Kendra Bracken Ferguson: Builder, Operator, Dealmaker02:22 The Thanksgiving Idea That Sparked Digital Brand Architects04:03 How DBA Helped Invent The Creator Economy Before Instagram07:04 Knowing When To Walk Away—And Start Over08:10 Why “Trust” Became The Non-Negotiable Business Principle14:20 Inside The CAA Acquisition18:36 When The Deal Looks Good—But The Reality Doesn’t20:52 The Moment Everything Had To Change21:20 Redefining Failure: Pivots, Pressure, And Perspective22:41 Journaling, Self-Awareness, And Founder Survival Tools24:32 Rebuilding With Intention: The Real BrainTrust Vision25:12 From Agency To Studio To Fund26:39 Corporate Partnerships, Power Dynamics, And Hard Truths29:57 New Ventures, New Partners, And Building With Exit In Mind35:39 From Hustle To Harmony: Success, Sleep, And The Next Chapter

In this solo episode, Carrie pulls back the curtain on what it actually takes to build an exit strategy for women founders—from choosing the right co-founder to expanding into brokerage without chasing growth for growth’s sake. She explains why so many women struggle with confidence during the exit process and how mindset, timing, and preparation directly impact business valuation.You’ll also hear how the Whisper Group is evolving—from advisory to brokerage—and why selectivity is a competitive advantage when helping women navigate how to sell a company. If you’re building with an exit in mind or questioning whether you’re truly prepared for selling a business, this conversation will reshape how you think about female entrepreneurship and women founders exits.00:00 Season 6 begins: why this chapter is different00:43 The rise of women-owned businesses and the movement behind it01:28 A major announcement: bringing on a co-founder01:56 What actually matters when choosing the right co-founder03:06 New upgrades, merch, and what’s evolving this season03:23 Why we’re prioritizing in-person podcast conversations03:43 Expanding into brokerage — with intention and restraint05:12 The hidden cost of growth: expenses and pressure05:41 Letting go of scarcity thinking while scaling06:56 Why I’m genuinely excited about what’s ahead

In this episode, Nicole opens up about the hardest year of her life, balancing motherhood, money, and a messy business breakup, and how she found the strength to start over and build something entirely her own. 2:02 Nicole’s Journey Into Wealth Management   5:37 Transitioning Into An Independent Advisory Firm   6:27 Stepping Fully Into The Independent World   7:34 Building A Niche Focused On Professional Athletes   8:10 Supporting Exonerees With Their Financial Needs   10:50 Considering Leaving The Firm For Personal Reasons   12:33 Learning To Parent A Special Needs Child   14:00 Concerns Over A Partner’s Financial Decisions   17:40 Realizing It Was Time To Leave The Partnership   18:40 Embracing Full Independence In Her Business   20:00 Clients Rallying Behind Her During The Transition   21:40 Negotiating Exit Terms With Her Business Partner   24:28 Selling A Portion Of The Business   25:07 Acquiring Additional Wealth Management Firms   27:54 Lessons Learned From Business Partnerships   29:50 The Importance Of Strong Financial Planning  

In this episode, Molly Nutt shares how she pulled off two very different exits, what she learned about selling potential vs. profit, and how to protect your relationships when business gets personal. If you’ve ever wondered how founders actually navigate the messy, emotional side of selling, this is the one to listen to.    2:34 Starting The CEO Society   4:44 Creating A Friendship Clause In A Business Deal   5:38 How Acorn Grew During The CEO Society Era   6:24 Launching Oak’s Email Studio   8:14 Splitting Brands To Stay Focused   10:40 The Unexpected Offer To Buy Oaks   11:20 Why Agencies Want To Acquire Email Agencies   12:01 Trusting Your Gut During Negotiations   12:44 The Challenge Of Untangling Finances   15:30 Evaluating The True Value Of A New Brand   16:45 Wrestling With Seller’s Remorse   17:38 Selling Potential Versus Selling Historical Data   19:12 Transitioning Into Life After The Sale   20:25 Launching A Mentorship Program   22:36 Advice For Women Building Their Businesses   24:00 Why The Right Hire Changes Everything   27:03 Details On The Growth Season Mentorship Program  

In this raw and unfiltered interview, Sharmin Ali shares how a chance encounter on a flight changed her life forever. From joining a startup that became a unicorn to surviving a cardiac arrest at 32, she reveals what founders never talk about: burnout, bad investor deals, and the price of ambition. 2:10 Choosing To Stop Chasing A Career At Google   6:25 An Unexpected Job Offer Mid-Flight   8:14 Learning The Basics Of Venture Capital   10:05 Building Powerful Relationships In Pharma   11:49 Closing Her First Million-Dollar Pilot Deal   14:32 Launching Her YouTube Channel Back In 2014   17:00 Why Timing And Vision Matter In Startup Success   18:52 The Power Of Emotion In Marketing   21:49 Facing Cardiac Arrest Again At Age 32   24:14 Realizing Health Must Come First   27:10 Why You Should “Date” Your Investor   30:10 Learning To Let Go So The Business Can Grow   32:44 What She Learned From Acquiring A Company   34:41 Launching A Foundation To Support Entrepreneurs   37:43 Honest Reflections On The Entrepreneurial Journey   40:02 Key Advice For Aspiring Entrepreneurs   42:04 Why Every Founder Needs A Therapist  

Angela Pointon opens up about what it’s really like to buy out your partners, take on debt, and bet on yourself when everything’s on the line. From the hardest conversations to the relief of letting go, this episode is about courage, burnout, and knowing when to walk away—on your own terms.   2:32 How 11Outof11 was born from freelancing burnout   4:42 Leaving the commute and daycare guilt to go all-in on freelance   7:13 Designing an agency with a future sale in mind   9:50 The hardest step — deciding to buy out her partners   13:06 Third-party valuation, bank loans, and emotional fallout   15:32 Relief, confidence, and revenue skyrocketing post-buyout   18:51 Why she chose to sell just one year later   22:23 Choosing the right buyer and securing a 90-day transition   24:45 No regrets and closing the deal during her son’s graduation week   27:04 Fractional CMO life, building a mountain home, and family time   30:18 Learning to slow down after witnessing friends survive cancer   32:00 Why Angela’s real-world exit story matters  

Ever felt stuck running a business you no longer love—but you’re scared to let go? Meet Laura Roos, who sold her company without a broker, while pregnant, and turned the proceeds into her next seven-figure startup. This episode is messy, honest, and full of real talk about what it actually takes to walk away. 5:48 Why Selling the Business Felt Like a Dream Come True   8:01 How the Company Grew Rapidly During the Pandemic   9:59 Knowing It Was the Right Time to Sell   11:30 Shifting Her Focus Into a New Business Venture   14:10 Her Deep Obsession With Cannabis Dosing   16:11 Making the Final Decision to Sell   19:02 The First Meeting With a Business Broker   21:19 The Game-Changing Email From a Potential Buyer   22:57 The Hidden Challenges of Planning an Exit   26:04 Why You Always Need Multiple Interested Buyers   27:53 Mastering the Art of Negotiating Deal Terms   30:22 Renegotiating Terms Even After the Deal Is Struck   32:54 How She Created Predictability in Her Payments   34:32 The Current Success of Mary and Jane   37:25 The Hard Realities of Growing a Business  

What happens when the person running your company with you ends up buying it from you? Carey Linderman shares how she went from senior care to creating an entirely new category: the postpartum doula. And how she built a business that supported moms when no one else did, and why she ultimately decided to sell her company to her own #2.   2:10 Introducing Carey Linderman   4:44 Moving From Senior Care Into Postpartum Doula Work   7:01 Strengthening Family Bonding Through Postpartum Care   8:11 Why Postpartum Support Matters More Than Ever   9:45 Educating Families About True Postpartum Needs   12:56 Creating a Comprehensive Doula Certification Course   13:57 Building a Credible and Trusted Certification   14:29 Bringing Experts Together to Elevate the Program   15:12 Marketing the Doula Certification to the Right People   16:03 Preparing Emotionally and Strategically to Sell the Business   20:46 How an Employee Ended Up Buying the Business   23:16 Financing the Business Purchase the Smart Way   24:20 Carey’s Advice on Letting Go When It’s Time to Exit

What do you do when you raise venture money… and then realize it’s not the right path? For Elle Hempen, co-founder of The Atlas, the answer was bold: sell just one year later.   In this episode, we talk about how a Google spreadsheet turned into a tech company, why she decided to skip the long VC grind, and how she negotiated an exit during the chaos of COVID. From pitching at Y Combinator while 8 months pregnant to getting a cold email from the exact company she dreamed of selling to, Elle’s story is packed with twists, hard choices, and the kind of honesty you rarely hear in startup land. 2:11 Why Valuing Early-Stage Tech Companies Is So Critical   5:00 Building the Atlas Platform From a Real-World Problem   6:34 Launching the First Version Back in 2016   9:06 Creating a Strong, Scalable Data Infrastructure   10:54 Deciding It Was Time to Fundraise for Growth   12:29 Applying to Y Combinator to Fuel Expansion   15:06 Fundraising in the Middle of a Market Crash   17:01 Finding the Right Strategic Investor   20:41 Soul-Searching to Determine the Company’s Direction   23:12 Valuing the Business Based on Future Potential   25:47 Celebrating a Rare and Remarkable Tech Achievement   29:02 Reflecting on Five Years of Building and Learning   30:40 Exploring What’s Next After the Exit   32:23 The Unique Energy of Being an Entrepreneur   34:40 Is an MBA Worth It for Founders?   36:57 Aligning Education With Real Business Needs